WO2024058001A1 - Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound - Google Patents
Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound Download PDFInfo
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- WO2024058001A1 WO2024058001A1 PCT/JP2023/032326 JP2023032326W WO2024058001A1 WO 2024058001 A1 WO2024058001 A1 WO 2024058001A1 JP 2023032326 W JP2023032326 W JP 2023032326W WO 2024058001 A1 WO2024058001 A1 WO 2024058001A1
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- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical class [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 1
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- JGFLAAWSLCPCDY-UHFFFAOYSA-N benzene;cyclopenta-1,3-diene;iron Chemical class [Fe].C1C=CC=C1.C1=CC=CC=C1 JGFLAAWSLCPCDY-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 125000005620 boronic acid group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229940125368 controlled substance Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- GUOJYIXWHMJFDM-UHFFFAOYSA-N decan-2-yl prop-2-enoate Chemical compound CCCCCCCCC(C)OC(=O)C=C GUOJYIXWHMJFDM-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- YDMWUMUNUXUYKT-UHFFFAOYSA-N ethyl [(1-oxo-1-phenylpropan-2-ylidene)amino] carbonate Chemical compound CCOC(=O)ON=C(C)C(=O)C1=CC=CC=C1 YDMWUMUNUXUYKT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000011416 infrared curing Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- GZTPJDLYPMPRDF-UHFFFAOYSA-N pyrrolo[3,2-c]pyrazole Chemical compound N1=NC2=CC=NC2=C1 GZTPJDLYPMPRDF-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
Definitions
- the present invention relates to a colored composition containing an isoindoline pigment.
- the present invention also relates to a film, an optical filter, a solid-state image sensor, an image display device, and a compound.
- a color filter is used as key devices for displays and optical elements.
- a color filter usually includes pixels of three primary colors, red, green, and blue, and serves to separate transmitted light into the three primary colors.
- the colored pixels of each color of the color filter are manufactured using a colored composition containing a coloring agent.
- Patent Document 1 discloses that a color filter or the like can be manufactured using a coloring composition containing an isoindoline pigment such as Color Index Pigment Yellow 185, an isoindoline derivative having a barbituric acid structure, a resin, and a solvent. Are listed.
- Equipment such as solid-state image sensors equipped with optical filters may be used in environments with large temperature fluctuations. For this reason, it is desired that the performance of films used in optical filters and the like is less likely to fluctuate even in environments with large temperature fluctuations.
- an object of the present invention is to provide a colored composition that can produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Further, an object of the present invention is to provide a film, an optical filter, a solid-state image sensor, an image display device, and a compound.
- the present invention provides the following.
- X 1 represents N or CR 8
- R 1 to R 9 each independently represent a hydrogen atom or a substituent, At least one of R 1 to R 9 has an acid group or a basic group, Two or more of R 1 to R 8 may be combined to form a ring.
- R 7 is an electron-withdrawing group
- X 1 is CR 8
- R 8 contains an acid group or a basic group.
- R 1 and R 2 are each independently an alkyl group or an aryl group, or R 1 and R 2 are combined to form a ring, ⁇ 1 > or the colored composition described in ⁇ 2>.
- ⁇ 5> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 4>.
- ⁇ 6> An optical filter having the film according to ⁇ 5>.
- ⁇ 7> A solid-state imaging device having the film according to ⁇ 5>.
- ⁇ 8> An image display device having the film according to ⁇ 5>.
- X 1 represents N or CR 8
- R 1 to R 9 each independently represent a hydrogen atom or a substituent
- At least one of R 1 to R 9 has an acid group or a basic group
- Two or more of R 1 to R 8 may be combined to form a ring.
- the present invention can provide a colored composition that can produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Further, the present invention can provide a film, an optical filter, a solid-state imaging device, an image display device, and a compound.
- ⁇ is used to include the numerical values described before and after it as a lower limit and an upper limit.
- the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the term "alkyl group” includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
- the light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
- EUV light extreme ultraviolet rays
- (meth)acrylate” represents acrylate and/or methacrylate
- (meth)acrylic represents both acrylic and/or methacrylic
- (meth)acrylate” represents acrylic and/or methacrylate.
- Acryloyl refers to either or both of acryloyl and methacryloyl.
- Me in the structural formula represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- Ph represents a phenyl group
- Bn represents a benzyl group.
- the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
- the total solid content refers to the total mass of all components of the composition excluding the solvent.
- pigment means a compound that is difficult to dissolve in a solvent.
- the term "process” is used not only to refer to an independent process, but also to include a process in which the intended effect of the process is achieved even if the process cannot be clearly distinguished from other processes. .
- the colored composition of the present invention is characterized by containing a coloring agent containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent.
- the colored composition of the present invention it is possible to produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations.
- the compound represented by formula (1) contained in the coloring composition of the present invention interacts with the isoindoline pigment and is adsorbed to the isoindoline pigment.
- the acid group or basic group contained in the compound represented by formula (1) interacts with the resin and is adsorbed to the resin.
- the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters, and more preferably used as a coloring composition for color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and more preferably used as a coloring composition for forming pixels of a color filter.
- Types of pixels in the color filter include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc., and preferably red pixels, green pixels, or yellow pixels; It is more preferable that the pixel is a green pixel, and even more preferable that it is a green pixel.
- the wavelength at which the light transmittance of the film becomes 50% is preferably in the wavelength range of 470 to 520 nm, and preferably 475 to 520 nm. It is more preferable that it exists in the wavelength range of 520 nm, and even more preferably that it exists in the wavelength range of 480 to 520 nm. Among these, it is preferable that the wavelength at which the light transmittance is 50% exists in the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm.
- the short wavelength at which the light transmittance is 50% is preferably in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- the wavelength on the long wavelength side at which the light transmittance is 50% is preferably in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm.
- a colored composition capable of forming a film having such spectral characteristics is preferably used as a colored composition for forming green pixels of a color filter.
- the colored composition of the present invention contains a coloring agent.
- the coloring agent used includes a pigment. More specifically, the coloring agent used includes an isoindoline pigment.
- the average primary particle diameter of the pigment is preferably 1 to 200 nm.
- the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
- the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
- the primary particle diameter of a pigment can be calculated
- the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 pigment primary particles.
- the primary particles of pigment refer to independent particles without agglomeration.
- the crystallite size determined from the half-value width of the peak derived from any crystal plane in the X-ray diffraction spectrum of the pigment when CuK ⁇ rays are used as the X-ray source is preferably 0.1 to 100 nm, and 0. It is more preferably .5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
- the specific surface area of the pigment is preferably 1 to 300 m 2 /g.
- the lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more.
- the upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less.
- the value of the specific surface area is determined according to DIN 66131: determination of the specific surface area of solids by gas adsorption according to the BET (Brunauer, Emmett and Teller) method. (Measurement of specific surface area of solids).
- the coloring composition of the present invention contains an isoindoline pigment.
- the isoindoline pigment is a yellow pigment.
- the isoindoline pigment is preferably an isoindoline pigment having a pyrazolidinedione structure.
- Examples of the isoindoline pigment having a pyrazolidinedione structure include a compound represented by formula (PI-1). Note that the bond of the wavy line between X P1 and R P7 in formula (PI-1) may be such that R P7 is on the lower side (R P6 side) as in formula (PI-1), or R P7 may be on the lower side (R P6 side). This means that it may be on the upper side ( RP9 side).
- X P1 represents N or CR P8
- R P1 to R P9 each independently represent a hydrogen atom or a substituent
- Two or more of R P1 to R P8 may be bonded to form a ring.
- Substituents represented by R P1 to R P9 in formula (PI-1) include a halogen atom, a hydroxy group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, and an alkoxycarbonyl group. , an alkylthio group, an arylthio group and a morpholino group. These groups may further have a substituent when the group is a substitutable group.
- Additional substituents include halogen atoms, hydroxy groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. It will be done.
- R P1 and R P2 in formula (PI-1) are each independently preferably a hydrogen atom, an alkyl group or an aryl group, more preferably an alkyl group or an aryl group, and are an alkyl group. is even more preferable. Moreover, it is preferable that R P1 and R P2 are the same group.
- the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2.
- the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent.
- substituents examples include a halogen atom, a hydroxy group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
- the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
- the aryl group may have a substituent.
- substituents examples include a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
- R P1 and R P2 are each independently preferably a hydrogen atom, a methyl group, a phenyl group, or a benzyl group, and more preferably a methyl group, a phenyl group, or a benzyl group.
- R P1 and R P2 in formula (PI-1) may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the ring formed may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
- R P3 to R P6 in formula (PI-1) each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, It is preferably a carbamoyl group or an alkoxycarbonyl group, more preferably a hydrogen atom, an alkyl group or an alkoxy group, and even more preferably a hydrogen atom.
- alkyl group, aryl group, alkoxy group, heteroaryl group, acyl group, carbamoyl group, alkoxycarbonyl group, alkylthio group, arylthio group and morpholino group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
- R P3 to R P6 of formula (PI-1) may be bonded to form a ring.
- the ring formed is preferably an aromatic ring, more preferably a benzene ring.
- R P4 and R P5 are preferably combined to form a ring, more preferably an aromatic ring, and even more preferably a benzene ring.
- the formed ring may have a substituent.
- substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
- R P7 in formula (PI-1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and is an electron-withdrawing group. It is more preferable that there be.
- the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
- the above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent.
- Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
- X P1 in formula (PI-1) is preferably CR P8 .
- R P8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and more preferably an electron-withdrawing group.
- the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
- the above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent.
- Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
- R P7 and R P8 may be combined to form a ring.
- the ring formed is preferably a pyrazolidinedione ring.
- the ring formed may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
- X P1 is CR P8 , and at least one of R P7 and R P8 is preferably an electron-withdrawing group, and R P7 and R P8 are both electron-withdrawing groups. It is more preferable that
- R P9 in formula (PI-1) is preferably a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, or an aryl group; It is more preferable that The above alkyl group, aryl group, and heteroaryl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
- the compound represented by formula (PI-1) is preferably a compound represented by formula (PI-2) or formula (PI-3), and is preferably a compound represented by formula (PI-2). It is more preferable.
- the bond of the wavy line connecting R P17 and R P18 in formula (PI-2) is that R P17 is on the lower side (R P16 side) and R P18 is on the upper side (R P19 side). ), or it means that R P18 may be on the lower side (R P16 side) and R P17 may be on the upper side (R P19 side).
- R P11 to R P19 each independently represent a hydrogen atom or a substituent, and two or more of R P11 to R P16 may be bonded to form a ring
- R P21 to R P29 each independently represent a hydrogen atom or a substituent, and two or more of R P21 to R P28 may be bonded to form a ring
- R P11 to R P16 of formula (PI-2) and R P21 to R P26 of formula (PI-3) have the same meaning as R P1 to R P6 of formula (PI-1), and their preferred ranges are also the same.
- R P19 in formula (PI-2) and R P29 in formula (PI-3) have the same meaning as R P9 in formula (PI-1), and the preferred ranges are also the same.
- R P17 and R P18 in formula (PI-2) are each independently an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group. , more preferably an electron-withdrawing group.
- the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
- R P27 and R P28 in formula (PI-3) are the same as preferred embodiments of R P1 and R P2 in formula (PI-1).
- R P27 and R P28 in formula (PI-3) may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the formed ring may have a substituent.
- substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
- R P21 , R P22 , R P27 and R P28 are preferably all the same group.
- the compound represented by formula (PI-1) is preferably a compound having maximum absorption in the wavelength range of 400 nm to 700 nm, more preferably a compound having maximum absorption in the wavelength range of 400 nm to 600 nm, Particularly preferred is a compound having maximum absorption in the wavelength range of 400 nm to 500 nm.
- Specific examples of the compound represented by formula (PI-1) include compounds (Y-1) to (Y-7) used in the examples described below.
- the isoindoline pigment contains C. I. Pigment Yellow 139, 185, etc. can also be used.
- the colored composition of the present invention can further contain a coloring agent other than the isoindoline pigment.
- Other colorants include yellow colorants, orange colorants, red colorants, green colorants, purple colorants, blue colorants, and the like.
- Other colorants may be pigments or dyes.
- the pigment may be either an inorganic pigment or an organic pigment, but organic pigments are preferable from the viewpoint of wide color variations, ease of dispersion, safety, and the like.
- the other coloring agent preferably includes at least one selected from a yellow pigment, an orange pigment, a red pigment, a green pigment, a purple pigment, and a blue pigment, and at least one selected from a green pigment, a yellow pigment, and a red pigment. It is more preferable that it contains, and it is especially preferable that it contains at least a green pigment.
- red colorants examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, etc. It is preferably a compound, and more preferably a diketopyrrolopyrrole compound. Moreover, it is preferable that the red colorant is a red pigment. Moreover, it is preferable that the red pigment is a diketopyrrolopyrrole pigment.
- red colorants include C.I. I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, Examples include red pigments such as 279, 291, 294, 295, 296, 297, and the like
- C. I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272 are preferred, and C.I. I. Pigment Red 254, 264, and 272 are more preferred, and C.I. I. Pigment Red 254 and 264 are more preferred.
- the green coloring agent examples include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. Moreover, it is preferable that the green coloring agent is a green pigment. Moreover, it is preferable that the green pigment is a phthalocyanine pigment.
- green colorants include C.I. I.
- examples include green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66.
- halogenated zinc phthalocyanine has an average number of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule.
- Pigments can also be used.
- Specific examples include compounds described in International Publication No. 2015/118720.
- C. I. Pigment Green 7, 36, 58, 62, and 63 are preferred.
- orange colorants include C.I. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. orange pigments.
- yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds.
- the yellow colorant is a yellow pigment.
- Specific examples of yellow colorants include C.I. I.
- Examples include yellow pigments such as 194, 199, 213, 214, 215, 228, 231,
- an azobarbituric acid nickel complex having the following structure can also be used.
- purple colorants include C.I. I.
- Examples include purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
- blue colorants include C.I. I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc.
- examples include pigments.
- an aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant.
- Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A No. 2012-247591 and paragraph number 0047 of JP-A No. 2011-157478.
- Dyes can also be used as other colorants.
- dyes There are no particular restrictions on the dye, and known dyes can be used.
- pyrazole azo series, anilinoazo series, triarylmethane series, anthraquinone series, anthrapyridone series, benzylidene series, oxonol series, pyrazolotriazole azo series, pyridone azo series, cyanine series, phenothiazine series, pyrrolopyrazole azomethine series, xanthene series Examples include phthalocyanine-based, benzopyran-based, indigo-based, and pyrromethene-based dyes.
- colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP2020-117638, and International Publication No. 2020/174991.
- halogenated zinc phthalocyanine pigment described in Patent No. 6809649, JP 2020-180176 Isoindoline compounds described in JP-A No. 2021-187913, phenothiazine compounds described in JP-A No. 2021-187913, halogenated zinc phthalocyanine described in International Publication No. 2022/004261, and halogenated compounds described in International Publication No. 2021/250883.
- Zinc phthalocyanine can be used.
- the other colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, in the rod-like structure, or in both structures.
- colorants include a quinophthalone compound represented by formula 1 in Korean Patent Publication No. 10-2020-0030759, a polymer dye described in Korean Publication Patent No. 10-2020-0061793, and JP-A No. 2022-029701.
- the coloring agent described in WO 2022/014635, the aluminum phthalocyanine compound described in WO 2022/024926, the compound described in JP 2022-045895, WO Compounds described in No. 2022/050051 can also be used.
- the coloring composition of the present invention contains a green colorant such as a green pigment as another colorant
- the coloring composition of the present invention is preferably used as a coloring composition for forming green pixels of a color filter.
- the coloring composition of the present invention contains a red colorant such as a red pigment as another colorant
- the coloring composition of the present invention is preferably used as a coloring composition for forming red pixels of a color filter.
- the coloring agent contained in the coloring composition may include two or more types of chromatic coloring agents, and black may be formed by a combination of two or more types of chromatic coloring agents.
- a colored composition is preferably used as a colored composition for forming an infrared transmission filter.
- combinations of chromatic colorants in the case where black color is formed by a combination of two or more chromatic colorants include the following. (1) Embodiment containing a red colorant, a blue colorant, and a yellow colorant. (2) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
- the content of the coloring agent in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and even more preferably 65% by mass or less. Only one type of colorant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the content of the isoindoline pigment in the total solid content of the coloring composition is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 5% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and even more preferably 65% by mass or less. Only one type of isoindoline pigment may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the content of the isoindoline pigment in the colorant is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more.
- the upper limit can be 100% by mass, 70% by mass or less, and 50% by mass or less.
- the content of yellow pigment in the colorant is preferably 30% by mass or more, and preferably 40% by mass or more.
- the content is more preferably 50% by mass or more.
- the yellow pigment contains an isoindoline pigment.
- the content of the isoindoline pigment in the yellow pigment is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, and 90% by mass or less.
- the colored composition of the present invention contains a compound represented by formula (1) (hereinafter also referred to as a specific compound).
- a compound represented by formula (1) hereinafter also referred to as a specific compound.
- Specific compounds are also compounds of the invention.
- the specific compound is used as a dispersion aid for pigments (preferably isoindoline pigments).
- a dispersion aid is a material for improving the dispersibility of pigments in a coloring composition. Note that the bond of the wavy line between X 1 and R 7 in formula (1) may be such that R 7 is on the lower side (R 6 side) as in formula (1), or R 7 is on the upper side (R 6 side). 9 side).
- X 1 represents N or CR 8
- R 1 to R 9 each independently represent a hydrogen atom or a substituent
- At least one of R 1 to R 9 has an acid group or a basic group
- Two or more of R 1 to R 8 may be combined to form a ring.
- Examples of the substituents represented by R 1 to R 9 in formula (1) include the groups listed below for substituent T, acid groups, and basic groups.
- Examples of the acid group include a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, an imide acid group, and salts thereof.
- Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions, imidazolium ions, pyridinium ions, Examples include phosphonium ions.
- the imidic acid group is preferably a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 ; or -SO 2 NHCOR X4 is more preferred, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 is even more preferred.
- R X1 to R X4 each independently represent an alkyl group or an aryl group.
- the alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
- the substituent is preferably a halogen atom, more preferably a fluorine atom.
- R X1 to R X4 are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, and more preferably an alkyl group containing a fluorine atom.
- the number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.
- the acid group is preferably a carboxy group, a sulfo group, a phosphoric acid group, a group represented by -SO 2 NHSO 2 Rf 1 , or a salt thereof.
- Rf 1 in the group represented by -SO 2 NHSO 2 Rf 1 represents an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom.
- Examples of the basic group include an amino group, a pyridinyl group and its salts, an ammonium group salt, and a phthalimidomethyl group.
- Examples of atoms or atomic groups constituting the salt include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
- the basic group is preferably an amino group.
- Examples of the amino group include a group represented by -NR x11 R x12 and a cyclic amino group.
- R x11 and R x12 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
- the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
- the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent. Examples of the substituent include the substituent T described below.
- the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
- the aryl group may have a substituent. Examples of the substituent include the substituent T described below.
- R 1 and R in formula (1) are each independently preferably a hydrogen atom, an alkyl group, an aryl group, an acid group, or a basic group, and more preferably a hydrogen atom, an alkyl group, or an aryl group.
- an alkyl group is more preferable.
- R 1 and R 2 are the same group.
- the number of carbon atoms in the alkyl group represented by R 1 and R 2 is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2.
- the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
- the alkyl group may have a substituent. Substituents include halogen atoms, hydroxy groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and bases. Examples include sexual groups.
- the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
- the aryl group may have a substituent.
- Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and bases. Examples include sexual groups.
- R 1 and R 2 in formula (1) are each independently preferably a hydrogen atom, a methyl group, a phenyl group, or a benzyl group, and more preferably a methyl group, a phenyl group, or a benzyl group.
- R 1 and R 2 in formula (1) may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the formed ring may have a substituent.
- Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
- R 3 to R 6 in formula (1) each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, or a carbamoyl group.
- an alkoxycarbonyl group, an acid group, or a basic group including a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, and a carbamoyl group.
- an alkoxycarbonyl group more preferably a hydrogen atom, an alkyl group or an alkoxy group, and particularly preferably a hydrogen atom.
- R 3 to R 6 in formula (1) may be combined to form a ring.
- the ring formed is preferably an aromatic ring, more preferably a benzene ring.
- R 4 and R 5 are preferably combined to form a ring, more preferably an aromatic ring, and even more preferably a benzene ring.
- the ring formed may have a substituent.
- Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
- R7 in formula (1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group, and an alkyl group, It is more preferably an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group or an alkoxycarbonyl group, and even more preferably an electron-withdrawing group.
- the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
- the above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent.
- Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc.
- the group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
- R 8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group; It is more preferably a group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and even more preferably a cyano group, a carbamoyl group, or an acyl group.
- the above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent.
- Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc.
- the group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
- R 8 is preferably a group having an acid group or a basic group, and is an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent. is more preferred, an acyl group or carbamoyl group having an acid group or a basic group as a substituent is even more preferred, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferred.
- R 7 and R 8 may be combined to form a ring.
- the ring formed is preferably a pyrazolidinedione ring.
- the formed ring may have a substituent.
- Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
- R9 in formula (1) is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an acid group, or a basic group, more preferably a hydrogen atom, an alkyl group, or an aryl group; More preferably, it is an atom.
- the above alkyl group, aryl group and heteroaryl group may further have a substituent. Further substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and basic groups. Examples include groups.
- At least one of R 1 to R 9 in formula (1) has an acid group or a basic group.
- at least one of R 7 and R 8 in formula (1) preferably has an acid group or a basic group.
- the acid group and basic group include the groups mentioned above. Among these, it is particularly preferable that R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains an acid group or a basic group.
- R 8 is preferably an aryl group, heteroaryl group, acyl group, carbamoyl group, or alkoxycarbonyl group having an acid group or basic group as a substituent; It is more preferably an acyl group or a carbamoyl group, and particularly preferably a carbamoyl group having an acid group or a basic group as a substituent.
- R 1 to R 9 in formula (1) has a basic group
- at least one of R 7 and R 8 has a basic group, since the generation of defects can be further suppressed. It is more preferable to have a functional group.
- R 7 is an electron-withdrawing group
- X 1 is CR 8
- R 8 contains a basic group.
- R 8 is preferably an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having a basic group as a substituent, and an acyl group or a carbamoyl group having a basic group as a substituent. More preferably, it is a carbamoyl group having a basic group as a substituent.
- substituent T examples include the following groups.
- Halogen atom e.g. fluorine atom, chlorine atom, bromine atom, iodine atom
- alkyl group preferably an alkyl group having 1 to 30 carbon atoms
- alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
- alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
- an aryl group preferably an aryl group having 6 to 30 carbon atoms
- a heteroaryl group preferably a heteroaryl group having 1 to 30 carbon atoms
- an alkoxy group preferably (alkoxy group having 1 to 30 carbon atoms)
- aryloxy group preferably aryloxy group having 6 to 30 carbon atoms
- heteroaryloxy group preferably heteroaryloxy group having 1 to 30 carbon atoms
- acyl group preferably is an acyl group having 2 to 30 carbon atoms
- the specific compound is preferably a compound represented by formula (2) or formula (3), and more preferably a compound represented by formula (2).
- the bond of the wavy line connecting R 17 and R 18 in formula (2) is that R 17 is on the lower side (R 16 side) and R 18 is on the upper side (R 19 side) as in formula (2).
- R 18 may be on the lower side (R 16 side) and R 17 may be on the upper side (R 19 side).
- R 11 to R 19 each independently represent a hydrogen atom or a substituent, At least one of R 11 to R 19 has an acid group or a basic group, Two or more of R 11 to R 16 may be combined to form a ring;
- R 21 to R 29 each independently represent a hydrogen atom or a substituent, At least one of R 21 to R 29 has an acid group or a basic group, Two or more of R 21 to R 28 may be combined to form a ring;
- R 11 to R 16 in formula (2) and R 21 to R 26 in formula (3) have the same meanings as R 1 to R 6 in formula (1), and their preferred ranges are also the same.
- R 19 in formula (2) and R 29 in formula (3) have the same meaning as R 9 in formula (1), and the preferred ranges are also the same.
- R 17 and R 18 in formula (2) are each independently an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group or a basic group. It is preferable that there be.
- R 17 and R 18 is an electron-withdrawing group.
- the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
- One of R 17 and R 18 is preferably an electron-withdrawing group, and the other is preferably a group having an acid group or a basic group, more preferably a group having a basic group.
- the group having an acid group or a basic group is preferably an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent;
- An acyl group or a carbamoyl group having a basic group as a substituent is more preferable, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferable.
- R 27 and R 28 in formula (3) are the same as the preferred embodiments of R 1 and R 2 in formula (1).
- R 27 and R 28 in formula (3) may be combined to form a ring.
- the ring formed is preferably a 5-membered ring or a 6-membered ring.
- the formed ring may have a substituent.
- Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
- R 21 , R 22 , R 27 and R 28 are all the same group.
- Specific examples of the specific compound include compounds (YY-1) to (YY-13) used in Examples described below.
- the content of the specific compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass.
- the lower limit is preferably 1% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
- the content of the specific compound is preferably 1 to 100 parts by weight based on 100 parts by weight of the isoindoline pigment.
- the lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more.
- the upper limit is preferably 70 parts by mass or less, more preferably 50 parts by mass or less. Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the colored composition of the present invention can contain pigment derivatives (hereinafter also referred to as other pigment derivatives) other than the above-mentioned specific compounds.
- Pigment derivatives are used, for example, as pigment dispersion aids.
- a dispersion aid is a material for improving the dispersibility of pigments in a coloring composition.
- pigment derivatives examples include compounds having at least one structure selected from a pigment structure and a triazine structure, and an acid group or a basic group.
- the above dye structures include quinoline dye structure, benzimidazolone dye structure, benzisoindole dye structure, benzothiazole dye structure, iminium dye structure, squarylium dye structure, croconium dye structure, oxonol dye structure, pyrrolopyrrole dye structure, diketo Pyrrolopyrrole dye structure, azo dye structure, azomethine dye structure, phthalocyanine dye structure, naphthalocyanine dye structure, anthraquinone dye structure, quinacridone dye structure, dioxazine dye structure, perinone dye structure, perylene dye structure, thiazine indigo dye structure, thioindigo dye structure, isoindoline dye structure, isoindolinone dye structure, quinophthalone dye structure, dithiol dye structure, triarylmethane dye structure, pyrromethene dye structure, etc.
- Examples of the acid groups and basic groups that other pigment derivatives have include the groups listed above as the acid groups and basic groups that the specific compounds mentioned above can have.
- pigment derivatives having excellent visible transparency can also be used.
- the maximum molar extinction coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength range of 400 to 700 nm is preferably 3000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less, and preferably 1000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less. is more preferable, and even more preferably 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more, and may be 10 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or more.
- pigment derivatives include the compound described in paragraph 0124 of International Publication No. 2022/085485, the benzimidazolone compound described in JP 2018-168244, or a salt thereof, and Patent No. 6996282.
- examples include compounds having an isoindoline skeleton represented by the general formula (1).
- the content of other pigment derivatives is preferably 100 parts by mass or less, more preferably 80 parts by mass or less, based on 100 parts by mass of the above-mentioned specific compound.
- the lower limit can be 1 part by mass or more, and can also be 3 parts by mass or more.
- the colored composition of the present invention contains a resin.
- the resin is blended, for example, for dispersing pigments in a coloring composition or for use as a binder.
- a resin used mainly for dispersing pigments and the like in a coloring composition is also referred to as a dispersant.
- this use of the resin is just one example, and the resin can also be used for purposes other than this use.
- the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
- the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
- the lower limit is preferably 4000 or more, more preferably 5000 or more.
- the resin examples include (meth)acrylic resin, epoxy resin, (meth)acrylamide resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and siloxane resin.
- the resin examples include the resin described in paragraphs 0091 to 0099 of International Publication No.
- the resin it is preferable to use a resin having acid groups.
- the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group.
- the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
- the lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more.
- the upper limit is more preferably 400 mgKOH/g or less, even more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
- the weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, more preferably 5,000 to 50,000. Further, the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
- the resin having an acid group preferably contains a repeating unit having an acid group in its side chain, and more preferably contains 5 to 70 mol% of repeating units having an acid group in its side chain based on the total repeating units of the resin.
- the upper limit of the content of repeating units having acid groups in their side chains is preferably 50 mol% or less, more preferably 30 mol% or less.
- the lower limit of the content of repeating units having acid groups in their side chains is preferably 10 mol% or more, more preferably 20 mol% or more.
- the colored composition of the present invention contains a resin having a basic group.
- the resin having a basic group is preferably a resin containing a repeating unit having a basic group in its side chain, and a resin having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group.
- a polymer is more preferable, and a block copolymer having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group is even more preferable.
- a resin having a basic group can also be used as a dispersant.
- the amine value of the resin having a basic group is preferably 5 to 300 mgKOH/g.
- the lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more.
- the upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
- resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK Chemie), Solsperse 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 385 00, 39000, 53095, 56000, 7100 (all manufactured by Japan Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
- the resin having a basic group is the block copolymer (B) described in paragraph numbers 0063 to 0112 of JP2014-219665A, and the block copolymer (B) described in paragraphs 0046 to 0076 of JP2018-156021A. It is also possible to use block copolymer A1, a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP-A No. 2019-184763, the contents of which are incorporated herein.
- the colored composition of the present invention contains a resin having an acid group and a resin having a basic group. According to this aspect, the storage stability of the colored composition can be further improved.
- the content of the resin having a basic group is preferably 20 to 500 parts by mass per 100 parts by mass of the resin having an acid group.
- the amount is preferably 30 to 300 parts by weight, more preferably 50 to 200 parts by weight.
- the resin it is also preferable to use a resin having an aromatic carboxy group (hereinafter also referred to as resin Ac).
- the aromatic carboxy group may be included in the main chain of the repeating unit, or may be included in the side chain of the repeating unit.
- the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
- an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
- the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2.
- the resin Ac is preferably a resin containing at least one type of repeating unit selected from a repeating unit represented by formula (Ac-1) and a repeating unit represented by formula (Ac-2).
- Ar 1 represents a group containing an aromatic carboxy group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- Ar 10 represents a group containing an aromatic carboxy group
- L 11 represents -COO- or -CONH-
- L 12 represents a trivalent linking group
- P 10 represents a polymer Represents a chain.
- Examples of the group containing an aromatic carboxy group represented by Ar 1 in formula (Ac-1) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like.
- Examples of the aromatic tricarboxylic anhydride and aromatic tetracarboxylic anhydride include compounds having the following structures.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1). or a group represented by the following formula (Q-2).
- the aromatic carboxy group-containing group represented by Ar 1 may have a crosslinkable group.
- the crosslinkable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group.
- Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). Examples include groups such as
- n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
- n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
- n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- Represents a group represented by 1) or a group represented by the above formula (Q-2).
- *1 represents the bonding position with L 1 .
- L 1 represents -COO- or -CONH-, and preferably represents -COO-.
- the divalent linking group represented by L 2 includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these. Examples include groups combining two or more of the following.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched, or cyclic.
- the number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
- the alkylene group and arylene group may have a substituent.
- the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
- L 2a is an alkylene group; an arylene group; a group combining an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group, and -O-, -CO-, -COO-, -OCO-, Examples include a group combining at least one selected from -NH- and -S-, and an alkylene group is preferred.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched, or cyclic.
- the alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxy group.
- the aromatic carboxy group-containing group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
- L 11 represents -COO- or -CONH-, preferably -COO-.
- the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these two groups. Examples include groups that combine more than one species.
- Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
- the aliphatic hydrocarbon group may be linear, branched, or cyclic.
- the aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 10 carbon atoms.
- the hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group.
- the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula
- L 12b represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents formula ( It represents the bonding position of Ac-2) with P10 .
- the trivalent linking group represented by L 12b is a hydrocarbon group; a hydrocarbon group, and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-.
- a hydrocarbon group or a group consisting of a hydrocarbon group and -O- is preferable.
- L 12c represents a trivalent linking group
- X 1 represents S
- *1 represents the bonding position with L 11 of formula (Ac-2)
- *2 represents the bonding position of formula (Ac-2). It represents the bonding position of Ac-2) with P10 .
- the trivalent linking group represented by L 12c is a hydrocarbon group; a hydrocarbon group and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-.
- a hydrocarbon group is preferable.
- P 10 represents a polymer chain.
- the polymer chain represented by P 10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units, and polyol repeating units.
- the weight average molecular weight of the polymer chain P 10 is preferably 500 to 20,000.
- the lower limit is preferably 1000 or more.
- the upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less. If the weight average molecular weight of P 10 is within the above range, the pigment will have good dispersibility in the composition.
- the resin having an aromatic carboxyl group is a resin having a repeating unit represented by formula (Ac-2), this resin is preferably used as a dispersant.
- the polymer chain represented by P 10 may contain a crosslinkable group.
- the crosslinkable group include ethylenically unsaturated bond-containing groups and cyclic ether groups.
- the colored composition of the present invention preferably contains a resin as a dispersant.
- the dispersant include acidic dispersants (acidic resins) and basic dispersants (basic resins).
- the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
- the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol % or more when the total amount of acid groups and basic groups is 100 mol %.
- the acid group that the acidic dispersant (acidic resin) has is preferably a carboxy group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g.
- the basic dispersant refers to a resin in which the amount of basic groups is greater than the amount of acid groups.
- the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of acid groups and basic groups is 100 mol%.
- the basic group that the basic dispersant has is preferably an amino group.
- the resin used as a dispersant is a graft resin.
- the descriptions in paragraphs 0025 to 0094 of JP-A No. 2012-255128 can be referred to, the contents of which are incorporated herein.
- the resin used as the dispersant is a resin having an aromatic carboxy group (resin Ac).
- resin Ac resin having an aromatic carboxy group
- examples of the resin having an aromatic carboxy group include those mentioned above.
- the resin used as a dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin has The basic nitrogen atom is not particularly limited as long as it exhibits basicity.
- the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
- the resin used as the dispersant has a structure in which a plurality of polymer chains are bonded to the core portion.
- resins include dendrimers (including star-shaped polymers).
- specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraph numbers 0196 to 0209 of JP-A No. 2013-043962.
- the resin used as a dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain.
- the content of the repeating unit having an ethylenically unsaturated bond-containing group in its side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and more preferably 20 to 70 mol% of the total repeating units of the resin. More preferably, it is mol%.
- resins described in JP 2018-087939, block copolymers (EB-1) to (EB-9) described in paragraph numbers 0219 to 0221 of Patent No. 6432077, and international publication Polyethyleneimine having a polyester side chain described in No. 2016/104803, block copolymer described in International Publication No. 2019/125940, block polymer having an acrylamide structural unit described in JP 2020-066687, A block polymer having an acrylamide structural unit described in JP-A No. 2020-066688, a dispersant described in International Publication No. 2016/104803, etc. can also be used.
- Dispersants are also available as commercial products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Japan Lubrizol, the Efka series manufactured by BASF, and Ajinomoto Fine Techno Co., Ltd. Examples include the Ajisper series manufactured by Manufacturer. Further, the product described in paragraph number 0129 of JP 2012-137564A and the product described in paragraph number 0235 of JP 2017-194662A can also be used as a dispersant.
- the content of resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the resin having acid groups in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the content of the dispersant is preferably 10 to 100 parts by weight per 100 parts by weight of the pigment.
- the lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more.
- the upper limit is preferably 80 parts by mass or less, more preferably 60 parts by mass or less.
- the colored composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more types of resin are included, the total amount thereof is preferably within the above range.
- the colored composition of the present invention contains a solvent.
- the solvent include organic solvents.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents.
- paragraph number 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein.
- Ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used.
- organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
- aromatic hydrocarbons benzene, toluene, xylene, ethylbenzene, etc.
- organic solvents for environmental reasons (for example, 50 mass ppm (parts) based on the total amount of organic solvents). per million), 10 mass ppm or less, and 1 mass ppm or less).
- an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content. It is preferable that the metal content of the organic solvent is, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by Toyo Gosei Co., Ltd. (Kagaku Kogyo Nippo, November 13, 2015). .
- Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon.
- the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one type of isomer may be included, or multiple types may be included.
- the content of peroxide in the organic solvent is 0.8 mmol/L or less, and it is more preferable that the organic solvent contains substantially no peroxide.
- the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the colored composition of the present invention does not substantially contain environmentally regulated substances.
- "not substantially containing environmentally controlled substances” means that the content of environmentally controlled substances in the coloring composition is 50 mass ppm or less, preferably 30 mass ppm or less. , more preferably 10 mass ppm or less, particularly preferably 1 mass ppm or less.
- environmentally controlled substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- REACH Registration Evaluation Authorization and Restriction of CHemicals
- PRTR Policy Release and It is registered as an environmentally regulated substance under the Transfer Register Act
- VOC Volatile Organic Compounds
- VOC Volatile Organic Compounds
- methods for reducing environmentally controlled substances include a method of heating or reducing pressure in the system to raise the temperature above the boiling point of the environmentally controlled substance to distill off the environmentally controlled substances from the system.
- distillation methods can be used at the stage of raw materials, at the stage of products obtained by reacting raw materials (for example, resin solution or polyfunctional monomer solution after polymerization), or at the stage of colored compositions prepared by mixing these compounds. This is possible at any stage.
- the colored composition of the present invention preferably contains a polymerizable compound.
- the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and the like.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- the polymerizable compound may be in any chemical form such as a monomer, prepolymer, or oligomer, but monomers are preferred.
- the molecular weight of the polymerizable compound is preferably 100 to 3,000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, and even more preferably 250 or more.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, More preferably, it is a compound containing 3 to 6 containing groups. Further, the polymerizable compound is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound. Specific examples of polymerizable compounds include compounds described in paragraph numbers 0075 to 0083 of International Publication No. 2022/065215.
- polymerizable compounds examples include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product: KAYARAD D-320) ; made by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (as a commercial product KAYARAD D-310; made by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (as a commercial product KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.; NK ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), and these (meth)acryloyl groups via ethylene glycol and/or propylene glycol residues.
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 35% by mass.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more.
- the colored composition of the present invention may contain only one kind of polymerizable compound, or may contain two or more kinds of polymerizable compounds. When two or more types of polymerizable compounds are included, it is preferable that the total amount thereof falls within the above range.
- the colored composition of the present invention can contain a photopolymerization initiator.
- the colored composition of the present invention contains a polymerizable compound, it is preferable that the colored composition of the present invention further contains a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet to visible range are preferred.
- the photopolymerization initiator is preferably a radical photopolymerization initiator.
- photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
- halogenated hydrocarbon derivatives e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.
- acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
- photopolymerization initiators include trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, and hexaarylbylene compounds.
- imidazole compounds onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones
- the compound is more preferably a compound selected from a compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
- photopolymerization initiators compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37 to 60p, vol. 19, No.
- hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc. can be mentioned.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, and Irgacure 117. 3, Irgacure 2959, Irgacure 127 (all BASF (manufactured by a company).
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, and Irgacure 36.
- Irgacure 369E Irgacure 379EG (all manufactured by BASF) (manufactured by).
- Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (manufactured by BASF), and the like.
- Examples of oxime compounds include the compound described in paragraph number 0142 of International Publication No. 2022/085485, the compound described in Patent No. 5430746, the compound described in Patent No. 5647738, and the general formula ( Examples include the compound represented by 1), the compound described in paragraphs 0022 to 0024, the compound represented by general formula (1) and the compound described in paragraphs 0117 to 0120 of JP-A-2021-170089.
- oxime compounds include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like.
- photopolymerization initiators include oxime compounds having a fluorene ring, oxime compounds having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring, oxime compounds having a fluorine atom, oxime compounds having a nitro group, and benzofuran skeleton.
- An oxime compound having a carbazole skeleton bonded with a substituent having a hydroxy group, and compounds described in paragraph numbers 0143 to 0149 of International Publication No. 2022/085485 can also be used.
- oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
- the oxime compound is preferably a compound having a maximum absorption wavelength in a wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in a wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably from 1000 to 300,000, even more preferably from 2000 to 300,000, and even more preferably from 5000 to 200,000. It is particularly preferable that there be.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g/L.
- a difunctional, trifunctional or more functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so that good sensitivity can be obtained.
- the crystallinity decreases and the solubility in solvents improves, making it difficult to precipitate over time, thereby improving the stability of the coloring composition over time.
- Specific examples of bifunctional or trifunctional or more functional photoradical polymerization initiators include compounds described in paragraph 0148 of International Publication No. 2022/065215.
- the content of the photopolymerization initiator in the total solid content of the colored composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount falls within the above range.
- the colored composition of the present invention can further contain an infrared absorber.
- an infrared absorber For example, when forming an infrared transmitting filter using the colored composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorber in the colored composition is shifted to the longer wavelength side. can be done.
- the infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorber is preferably a compound having a maximum absorption wavelength in a range of more than 700 nm and less than 1800 nm.
- the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less. .
- Infrared absorbers include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like. Specific examples of these include compounds described in paragraph numbers 0114 to 0121 of International Publication No. 2022/065215.
- the compound described in paragraph number 0121 of International Publication No. 2022/065215, the squarylium compound described in JP-A No. 2020-075959, and the squarylium compound described in Korean Patent Publication No. 10-2019-0135217 The copper complexes described above can also be used.
- the croconic acid compound described in JP 2021-195515, the infrared absorber described in JP 2022-022070, and the croconium compound described in WO 2019/021767 can also be used.
- tungsten oxide represented by the following formula described in paragraph number 0025 of European Patent No. 3,628,645 can also be used.
- M 1 and M 2 represent ammonium cations or metal cations, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, and d is 2.5 to 3.
- e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent. represent.
- the content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the colored composition of the present invention may contain only one type of infrared absorber, or may contain two or more types of infrared absorbers. When two or more types of infrared absorbers are included, the total amount thereof is preferably within the above range.
- the colored composition of the present invention can contain a compound having a cyclic ether group.
- the cyclic ether group include an epoxy group and an oxetanyl group.
- the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
- the epoxy compound include compounds having one or more epoxy groups in one molecule, and preferably compounds having two or more epoxy groups.
- the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
- the upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less.
- the lower limit of the epoxy groups contained in the epoxy compound is preferably two or more.
- epoxy compounds include those described in paragraph numbers 0034 to 0036 of JP2013-011869, paragraphs 0147 to 0156 of JP2014-043556, and paragraphs 0085 to 0092 of JP2014-089408.
- Compounds, compounds described in JP 2017-179172, xanthene type epoxy resins described in JP 2021-195421, and xanthene epoxy resins described in JP 2021-195422 can also be used.
- the epoxy compound may be a low-molecular compound (for example, molecular weight less than 2000, or even less than 1000), or a macromolecule (for example, molecular weight 1000 or more; in the case of a polymer, the weight average molecular weight is 1000 or more). But that's fine.
- the weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and even more preferably 3,000 or less.
- EHPE3150 manufactured by Daicel Corporation
- EPICLON N-695 manufactured by DIC Corporation
- Marproof G-0150M G-0105SA, G-0130SP, and G-0130SP.
- -0250SP G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all of which are epoxy group-containing polymers manufactured by NOF Corporation).
- the content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass.
- the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
- the upper limit is preferably 15% by mass or less, more preferably 10% by mass or less. Only one kind of compound having a cyclic ether group may be used, or two or more kinds thereof may be used. When two or more types are used, it is preferable that their total amount falls within the above range.
- the colored composition of the present invention can also contain polyalkyleneimine.
- Polyalkyleneimines are used, for example, as dispersion aids for pigments.
- a dispersion aid is a material for improving the dispersibility of pigments in a coloring composition.
- Polyalkyleneimine is a polymer obtained by ring-opening polymerization of alkyleneimine.
- Polyalkyleneimine is a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group, respectively.
- the alkylene imine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, even more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
- the molecular weight of the polyalkylene imine is preferably 200 or more, more preferably 250 or more.
- the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
- the molecular weight of the polyalkylene imine if the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkylene imine is the value calculated from the structural formula.
- the molecular weight of a specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used.
- the value of the number average molecular weight measured by the viscosity method is used. If the viscosity method cannot be used or it is difficult to measure, the number average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography) is used.
- the amine value of the polyalkylene imine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
- alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine, etc. Ethyleneimine or propyleneimine is preferable, and ethyleneimine is more preferable. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. Further, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more of primary amino groups based on the total of primary amino groups, secondary amino groups, and tertiary amino groups. , more preferably 30 mol% or more.
- Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
- the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass.
- the lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
- the upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less.
- the content of polyalkyleneimine is preferably 0.5 to 20 parts by weight per 100 parts by weight of the pigment.
- the lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more.
- the upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one type of polyalkylene imine may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
- the colored composition of the present invention may also contain a curing accelerator.
- the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds, and the like.
- Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485, the compound described in JP 2021-181406, and the like.
- the content of the curing accelerator in the total solid content of the colored composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
- the colored composition of the present invention can contain an ultraviolet absorber.
- the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, dibenzoyl compounds, and the like. Specific examples of such compounds include the compound described in paragraph number 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorber described in JP 2021-178918, and JP 2022-007884. It is also possible to use the ultraviolet absorbers described in .
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the colored composition of the present invention can contain a polymerization inhibitor.
- Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), Examples include 2,2'-methylenebis(4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
- the number of polymerization inhibitors may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
- the colored composition of the present invention can contain a silane coupling agent.
- the silane coupling agent include silane compounds having a hydrolyzable group, and preferably silane compounds having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction.
- the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, and an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, ureido groups, sulfide groups, and isocyanate groups. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferable.
- Specific examples of the silane coupling agent include compounds described in paragraph 0177 of International Publication No. 2022/085485.
- the content of the silane coupling agent in the total solid content of the colored composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. Only one type of silane coupling agent may be used, or two or more types may be used. In the case of two or more types, it is preferable that the total amount falls within the above range.
- the colored composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used.
- the surfactant is preferably a silicone surfactant or a fluorine surfactant.
- fluorosurfactant compounds described in paragraph numbers 0167 to 0173 of International Publication No. 2022/085485 can be used.
- nonionic surfactants examples include compounds described in paragraph 0174 of International Publication No. 2022/085485.
- silicone surfactants examples include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), and TSF- 4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK Chemie), and the like.
- a compound having the following structure can also be used as the silicone surfactant.
- the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% to 3.0% by mass.
- the number of surfactants may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
- the colored composition of the present invention can contain an antioxidant.
- antioxidants include phenol compounds, phosphite compounds, thioether compounds, and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenol compounds include hindered phenol compounds.
- a compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred.
- the above-mentioned substituents are preferably substituted or unsubstituted alkyl groups having 1 to 22 carbon atoms.
- a compound having a phenol group and a phosphorous acid ester group in the same molecule is also preferable.
- phosphorus-based antioxidants can also be suitably used.
- a phosphorus antioxidant tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepine-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl )oxy]ethyl]amine, ethylbis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like.
- antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Co., Ltd.).
- antioxidants include compounds described in paragraph numbers 0023 to 0048 of Patent No. 6268967, compounds described in International Publication No. 2017/006600, compounds described in International Publication No. 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used.
- the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
- the coloring composition of the present invention may optionally contain sensitizers, plasticizers, and other auxiliary agents (e.g., conductive particles, fillers, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances). , surface tension adjusting agent, chain transfer agent, etc.).
- sensitizers plasticizers
- other auxiliary agents e.g., conductive particles, fillers, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances.
- surface tension adjusting agent e.g., chain transfer agent, etc.
- the colored composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
- metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 , and SiO 2 .
- the primary particle diameter of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, even more preferably 5 to 50 nm.
- the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
- the colored composition of the present invention may also contain a lightfastness improver.
- a lightfastness improver examples include compounds described in paragraph number 0183 of International Publication No. 2022/085485.
- the colored composition of the present invention is substantially free of terephthalic acid ester.
- substantially not containing means that the content of terephthalic acid ester is 1000 mass ppb or less in the total amount of the coloring composition, more preferably 100 mass ppb or less, Particularly preferred is zero.
- the colored composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less.
- the type of metal is not particularly limited, but examples include alkali metals, alkaline earth metals, transition metals, Al, Sn, Pb, Bi, and the like.
- the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less. Examples of methods for reducing free metals and halogens in the colored composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification using ion-exchange resins.
- perfluoroalkyl sulfonic acids and their salts may be regulated.
- perfluoroalkylsulfonic acids particularly perfluoroalkylsulfonic acids whose perfluoroalkyl group has 6 to 8 carbon atoms
- salts thereof and perfluoroalkylsulfonic acids
- the content of fluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid whose perfluoroalkyl group has 6 to 8 carbon atoms) and its salt is 0.01 ppb to 1,000 ppb based on the total solid content of the coloring composition.
- the coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt.
- a coloring composition that is substantially free of and salts thereof.
- Compounds that can be substituted for regulated compounds include, for example, compounds that are excluded from regulated targets due to differences in the number of carbon atoms in perfluoroalkyl groups.
- the colored compositions of the present invention may include perfluoroalkyl sulfonic acids and salts thereof, and perfluoroalkyl carboxylic acids and salts thereof, to the maximum extent permissible.
- the water content of the colored composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the colored composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface condition (flatness, etc.), adjusting the film thickness, etc.
- the value of viscosity can be appropriately selected as required, but for example, at 25° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
- the viscosity can be measured using, for example, a cone plate type viscometer with the temperature adjusted to 25°C.
- the container for storing the coloring composition is not particularly limited, and any known container can be used. Further, as the storage container, the container described in paragraph 0187 of International Publication No. 2022/085485 can be used.
- the colored composition of the present invention can be prepared by mixing the above-mentioned components.
- the colored composition may be prepared by dissolving and/or dispersing all components in a solvent at the same time, or, if necessary, each component may be prepared as two or more solutions or dispersions as appropriate.
- a colored composition may be prepared by mixing these at the time of use (at the time of application).
- a process of dispersing pigments when preparing the colored composition.
- mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like.
- JP 2015-157893 A "Practical Application Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be suitably used.
- the particles may be made finer in a salt milling step.
- the descriptions in JP-A No. 2015-194521 and JP-A No. 2012-046629 can be referred to, for example.
- the colored composition In preparing the colored composition, it is preferable to filter the colored composition with a filter for the purpose of removing foreign substances and reducing defects.
- a filter for the purpose of removing foreign substances and reducing defects.
- Examples of the type of filter and filtration method used for filtration include the filters and filtration methods described in paragraph numbers 0196 to 0199 of International Publication No. 2022/085485.
- the film of the present invention is a film obtained from the colored composition of the present invention described above.
- the film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
- the film thickness of the film of the present invention can be adjusted as appropriate depending on the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
- the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta, or yellow hue, more preferably a green, red, or yellow hue. preferable. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc., and preferably red pixels, green pixels, and yellow pixels, and red pixels or green pixels. More preferably, it is a green pixel, and even more preferably a green pixel.
- the wavelength at which the light transmittance is 50% is preferably in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. More preferably, it exists within the wavelength range. Among these, it is preferable that the wavelength at which the light transmittance is 50% exists in the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the short wavelength at which the light transmittance is 50% is preferably in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm.
- the wavelength on the long wavelength side at which the light transmittance is 50% is preferably in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm.
- a film having such spectral characteristics is preferably used as a green pixel.
- the film of the present invention preferably has, for example, any one of the following spectral properties (1) to (4).
- the maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is
- the minimum value of the ratio in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light with wavelengths exceeding 700 nm.
- the maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength exceeding 850 nm.
- the maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength exceeding 940 nm.
- the maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1040 nm.
- the film of the present invention can be manufactured through a step of applying the colored composition of the present invention.
- the film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of methods for forming patterns (pixels) include photolithography and dry etching, with photolithography being preferred.
- Pattern formation by the photolithography method includes a step of forming a colored composition layer on a support using the colored composition of the present invention, a step of exposing the colored composition layer to light in a pattern, and a step of exposing the colored composition layer to light. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the colored composition layer (pre-bake step) and a step of baking the developed pattern (pixel) (post-bake step) may be provided.
- a colored composition layer is formed on a support using the colored composition of the present invention.
- the support is not particularly limited and can be appropriately selected depending on the application.
- a glass substrate, a silicon substrate, etc. may be mentioned, and a silicon substrate is preferable.
- a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix that isolates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with an underlayer for improving adhesion with the upper layer, preventing substance diffusion, or flattening the substrate surface.
- the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferable that the angle is 30 to 80° when measured with water.
- a known method can be used to apply the coloring composition.
- the coating method described in paragraph number 0207 of International Publication No. 2022/085485 can be used.
- the colored composition layer formed on the support may be dried (prebaked). If the film is manufactured by a low-temperature process, prebaking may not be performed.
- the prebaking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower.
- the lower limit can be, for example, 50°C or higher, or 80°C or higher.
- the prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Prebaking can be performed on a hot plate, oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing it to light through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. This allows the exposed portion to be cured.
- Radiation (light) that can be used during exposure includes g-line, i-line, etc. Furthermore, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm). Furthermore, a long-wave light source of 300 nm or more can also be used. As a light source, an electrodeless ultraviolet lamp system, a hybrid ultraviolet and infrared curing can be used.
- pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and pauses in short cycles (for example, on the millisecond level or less).
- the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
- the oxygen concentration during exposure can be appropriately selected, and in addition to being carried out in the atmosphere, for example, in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially
- the exposure may be performed in an oxygen-free atmosphere (without oxygen), or in a high oxygen atmosphere where the oxygen concentration exceeds 21 volume % (for example, 22 volume %, 30 volume %, or 50 volume %).
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000W/m 2 to 100000W/m 2 (for example, 5000W/m 2 , 15000W/m 2 , or 35000W/m 2 ). Can be done.
- the oxygen concentration and the exposure illuminance may be appropriately combined.
- the illuminance may be 10,000 W/m 2 when the oxygen concentration is 10% by volume, and 20,000 W/m 2 when the oxygen concentration is 35% by volume.
- the unexposed portions of the colored composition layer are developed and removed to form a pattern (pixel).
- the unexposed areas of the colored composition layer can be removed by development using a developer.
- the unexposed portions of the colored composition layer in the exposure step are eluted into the developer, leaving only the photocured portions.
- the temperature of the developer is preferably, for example, 20 to 30°C.
- the development time is preferably 20 to 180 seconds. Furthermore, in order to improve the ability to remove residues, the process of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
- Examples of the developer include organic solvents, alkaline developers, and alkaline developers are preferably used.
- the developer and cleaning method after development the developer and cleaning method described in paragraph number 0214 of International Publication No. 2022/085485 can be used.
- Additional exposure processing and post-bake are post-development curing processing to complete curing.
- the heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C.
- Post-baking can be carried out in a continuous or batch manner using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to maintain the developed film under the above conditions.
- the light used for exposure is preferably light with a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, and curing the entire colored composition layer to form a cured product layer; A step of forming a photoresist layer on this cured material layer, a step of exposing the photoresist layer in a pattern and then developing it to form a resist pattern, and etching the cured material layer using this resist pattern as a mask. It is preferable to include a step of dry etching using gas. In forming the photoresist layer, it is preferable to further perform a prebaking process.
- optical filter of the present invention has the film of the present invention described above.
- Types of optical filters include color filters and infrared transmission filters, and color filters are preferred.
- As a color filter it is preferable to have the film of the present invention as a colored pixel of the color filter.
- a protective layer may be provided on the surface of the film of the present invention.
- various functions such as oxygen blocking, low reflection, hydrophilic and hydrophobic properties, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m. Examples of methods for forming the protective layer include a method of coating a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of pasting a molded resin with an adhesive.
- Components constituting the protective layer include (meth)acrylic resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples include resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4 and the like, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 and Si 2 N 4 .
- the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
- a protective layer by applying a resin composition known methods such as a spin coating method, a casting method, a screen printing method, an inkjet method, etc. can be used as a method for applying the resin composition.
- organic solvent contained in the resin composition known organic solvents (eg, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used.
- chemical vapor deposition methods thermal chemical vapor deposition, plasma enhanced chemical vapor deposition, photochemical vapor deposition
- photochemical vapor deposition can be used as the chemical vapor deposition method.
- the protective layer may contain organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, and other additives, as necessary. It may contain.
- organic/inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride. , magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, and the like.
- the absorber for light of a specific wavelength a known absorber can be used.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by weight, more preferably 1 to 60% by weight, based on the total weight of the protective layer.
- the protective layer the protective layers described in paragraph numbers 0073 to 0092 of JP-A No. 2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned into a lattice shape by partition walls, for example.
- the solid-state imaging device of the present invention has the film of the present invention described above.
- the structure of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, but examples include the following structure.
- the substrate has a plurality of photodiodes that constitute the light receiving area of a solid-state image sensor (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and a transfer electrode made of polysilicon or the like.
- a device protective film made of silicon nitride or the like is formed on the light-shielding film to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. It has a configuration in which a color filter is provided on the device protective film.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include devices described in Japanese Patent Application Publication No. 2012-227478, Japanese Patent Application Publication No. 2014-179577, and International Publication No.
- an ultraviolet absorbing layer may be provided within the structure of the solid-state image sensor to improve light resistance.
- An imaging device equipped with the solid-state imaging device of the present invention can be used not only as a digital camera or an electronic device having an imaging function (such as a mobile phone), but also as an in-vehicle camera or a surveillance camera.
- the image display device of the present invention has the film of the present invention described above.
- Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device.
- Examples of an image display device and details of each image display device see, for example, “Electronic Display Devices (written by Akio Sasaki, Kogyo Chosenkai Co., Ltd., published in 1990)” and “Display Devices (written by Junaki Ibuki, published by Sangyo Tosho)”. Co., Ltd., issued in 1989).
- liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Chosenkai Co., Ltd., 1994)".
- Next Generation Liquid Crystal Display Technology edited by Tatsuo Uchida, published by Kogyo Chosenkai Co., Ltd., 1994.
- the present invention can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology.”
- the resulting solid was blown dry at 50°C to obtain 12.9 parts by mass of compound (Y-1).
- the (M+H)(posi) value in the mass spectrum of compound (Y-1) was 462.
- the maximum absorption wavelength of compound (Y-1) was in the wavelength range of 400 to 600 nm.
- Y-1 to Y-7 Compounds (Y-1) to (Y-7) with the following structure
- YY-1 to YY-13 Compounds (YY-1) to (YY-13) with the following structure
- S-1 to S-13 Compounds (S-1) to (S-13) with the following structure a-1 to a-13: Compounds (a-1) to (a-13) with the following structure b-1: Compound (b-1) with the following structure c-1 to c-4: Compounds (c-1) to (c-4) with the following structure
- (colorant) Y-1 to Y-7 Compounds (Y-1) to (Y-7) described above (isoindoline pigments having a pyrazolidinedione group) PY185:C.
- Pigment Green 63 green pigment, phthalocyanine pigment PR254:C.
- Pigment Red 254 red pigment, diketopyrrolopyrrole pigment
- Pigment Red 264 red pigment, diketopyrrolopyrrole pigment
- PR272 C.
- Pigment Red 272 red pigment, diketopyrrolopyrrole pigment
- Pigment Yellow 129 yellow pigment, azomethine pigment
- Pigment Yellow 150 yellow pigment, azo pigment
- I. Pigment Orange 71 range pigment, diketopyrrolopyrrole pigment
- PB15:6 C.
- I. Pigment Blue 15:6 blue pigment, phthalocyanine pigment
- B-1 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- B-2 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- B-3 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- Weight average molecular weight 20,000) B-4 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- B-5 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- Weight average molecular weight 20,000) B-6 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
- Weight average molecular weight 7000) B-7 Resin synthesized by the following method Flow an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and add 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA). and heated to 80°C while stirring.
- PGMEA propylene glycol monomethyl ether acetate
- a colored composition was produced by mixing the raw materials listed in the table below.
- Dispersions 1 to 67 Dispersions 1 to 67, comparative dispersions: Dispersions 1 to 67, comparative dispersions described above
- B-1 Resin shown as the above-mentioned dispersant B-1
- B-4 Resin shown as the above-mentioned dispersant B-4
- C-1 Resin with the following structure (the numerical value appended to the main chain is the molar ratio .
- C-2 Resin with the following structure (the numerical value appended to the main chain is the molar ratio.
- C-3 Resin with the following structure (the numerical value appended to the main chain is the mass ratio.
- C-4 Resin with the following structure (the numerical value appended to the main chain is the mass ratio.
- Weight average molecular weight 10600) C-5 Resin synthesized by the following method. Pour an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and add 371 parts by mass of 1-methoxy-2-propyl acetate. , and heated to 85° C. with stirring. Next, 54 parts by mass of acrylic acid, 225 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8 and 9-yl acrylate, and 81 parts by mass of vinyltoluene (isomer mixture).
- a mixed solution of 80 parts by weight of 1-methoxy-2-propyl acetate was added dropwise over 4 hours.
- a solution of 30 parts by mass of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 160 parts by mass of 1-methoxy-2-propyl acetate was added dropwise over 5 hours.
- the temperature was maintained at 85° C. for 4 hours and then cooled to room temperature to obtain a resin.
- the weight average molecular weight of the obtained resin was 10,600, the degree of dispersion was 2.01, and the acid value was 43 mgKOH/g.
- D-1 Compound with the following structure
- D-2 A mixture of compounds with the following structure (a mixture in which the molar ratio of the compound on the left (a hexafunctional (meth)acrylate compound) and the compound on the right (a pentafunctional (meth)acrylate compound) is 7:3)
- D-3 Compound with the following structure
- D-4 Trimethylolpropane ethylene oxide modified triacrylate (manufactured by Toagosei Co., Ltd., Aronix M-350)
- D-5 EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
- D-6 Ethoxylated dipentaerythritol hexamethacrylate
- E-1 to E-4 Compounds with the following structure E-5: 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-biimidazole
- F-1 KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxyl value 62 mgKOH/g)
- F-2 Compound with the following structure (weight average molecular weight 14,000). In the formula below, % indicating the proportion of repeating units is mol%.
- F-3 Ftergent 208G (manufactured by NEOS, fluorine-based surfactant)
- F-4 BYK-330 (manufactured by BYK Chemie, silicone surfactant)
- F-5 DOWSIL SH8400 FLUID (manufactured by Dow Toray Industries, Inc., silicone surfactant)
- G-1 Compound with the following structure (ultraviolet absorber)
- G-2 Compound with the following structure (compound having an epoxy group, weight average molecular weight 3500)
- G-3 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2'-bis(hydroxymethyl)-1-butanol)
- G-4 Compound with the following structure (silane coupling agent)
- G-5 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
- G-6 p-methoxyphenol (polymerization inhibitor)
- G-7 ADEKA STAB AO-80 (manufactured by ADEKA Co., Ltd., antioxidant)
- the colored compositions of Examples were excellent in the evaluation of the temperature cycle test. Similar results were obtained in Example 1 even when the surfactant was replaced with a solvent. Films formed from the colored compositions of Examples can be suitably used for optical filters, solid-state imaging devices, and image display devices.
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Abstract
Provided is a coloring composition that contains: a coloring agent containing an isoindolin pigment; a compound represented by formula (1); a resin; and a solvent. Also provided are: a film using the coloring composition; an optical filter; a solid-state imaging element; and an image display device. The compound is represented by formula (1). In formula (1), X1 denotes N or CR8, and R1 to R9 each independently denote a hydrogen atom or a substituent group. At least one of R1 to R9 has an acidic group or a basic group. Two or more of R1 to R8 may bond to each other to form a ring.
Description
本発明は、イソインドリン顔料を含む着色組成物に関する。また、本発明は、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物に関する。
The present invention relates to a colored composition containing an isoindoline pigment. The present invention also relates to a film, an optical filter, a solid-state image sensor, an image display device, and a compound.
近年、デジタルカメラ、カメラ付き携帯電話等の普及から、電荷結合素子(CCD)イメージセンサなどの固体撮像素子の需要が大きく伸びている。ディスプレイや光学素子のキーデバイスとしてカラーフィルタが使用されている。カラーフィルタは、通常、赤、緑及び青の3原色の画素を備えており、透過光を3原色へ分解する役割を果たしている。
In recent years, with the spread of digital cameras, camera-equipped mobile phones, etc., demand for solid-state image sensors such as charge-coupled device (CCD) image sensors has increased significantly. Color filters are used as key devices for displays and optical elements. A color filter usually includes pixels of three primary colors, red, green, and blue, and serves to separate transmitted light into the three primary colors.
カラーフィルタの各色の着色画素は、着色剤を含む着色組成物を用いて製造されている。
The colored pixels of each color of the color filter are manufactured using a colored composition containing a coloring agent.
特許文献1には、カラーインデックスピグメントイエロー185などのイソインドリン顔料と、バルビツール酸構造を有するイソインドリン誘導体と、樹脂と、溶剤とを含む着色組成物を用いてカラーフィルタなどを製造することが記載されている。
Patent Document 1 discloses that a color filter or the like can be manufactured using a coloring composition containing an isoindoline pigment such as Color Index Pigment Yellow 185, an isoindoline derivative having a barbituric acid structure, a resin, and a solvent. Are listed.
光学フィルタを備えた固体撮像素子などの機器について、温度変動の大きい環境下で使用されることがある。このため、光学フィルタなどに用いられる膜について、温度変動の大きい環境下でも、性能が変動しにくいことが望まれている。
Equipment such as solid-state image sensors equipped with optical filters may be used in environments with large temperature fluctuations. For this reason, it is desired that the performance of films used in optical filters and the like is less likely to fluctuate even in environments with large temperature fluctuations.
本発明者がイソインドリン顔料を含む着色組成物について検討を行ったところ、着色組成物を用いて得られる膜を温度変動のある環境下で保管した場合、膜中に欠陥が生じやすいことが分かった。
When the present inventor investigated a coloring composition containing an isoindoline pigment, it was found that defects are likely to occur in the film when the film obtained using the coloring composition is stored in an environment with temperature fluctuations. Ta.
よって、本発明の目的は、温度変動のある環境下でも欠陥の発生が抑制された膜を製造可能な着色組成物を提供することにある。また、本発明の目的は、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物を提供することにある。
Therefore, an object of the present invention is to provide a colored composition that can produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Further, an object of the present invention is to provide a film, an optical filter, a solid-state image sensor, an image display device, and a compound.
本発明者の検討によれば、後述する着色組成物により上記目的を達成できることを見出し、本発明を完成するに至った。よって、本発明は以下を提供する。
According to the studies of the present inventors, it was discovered that the above object can be achieved by the coloring composition described below, and the present invention was completed. Accordingly, the present invention provides the following.
<1> イソインドリン顔料を含む着色剤と、式(1)で表される化合物と、樹脂と、溶剤と、を含む着色組成物;
式(1)中、X1は、NまたはCR8を表し、
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。
<2> 上記式(1)において、R7が電子求引性基であり、X1がCR8であり、R8が酸基または塩基性基を含む、<1>に記載の着色組成物。
<3> 上記式(1)において、R1およびR2は、それぞれ独立してアルキル基もしくはアリール基であるか、または、R1とR2が結合して環を形成している、<1>または<2>に記載の着色組成物。
<4> 上記着色剤は、更に、緑色顔料を含む、<1>~<3>のいずれか1つに記載の着色組成物。
<5> <1>~<4>のいずれか1つに記載の着色組成物から得られる膜。
<6> <5>に記載の膜を有する光学フィルタ。
<7> <5>に記載の膜を有する固体撮像素子。
<8> <5>に記載の膜を有する画像表示装置。
<9> 式(1)で表される化合物;
式(1)中、X1は、NまたはCR8を表し、
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。 <1> A coloring composition containing a coloring agent containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent;
In formula (1), X 1 represents N or CR 8 ,
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
<2> The colored composition according to <1>, wherein in the formula (1), R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains an acid group or a basic group. .
<3> In the above formula (1), R 1 and R 2 are each independently an alkyl group or an aryl group, or R 1 and R 2 are combined to form a ring, <1 > or the colored composition described in <2>.
<4> The colored composition according to any one of <1> to <3>, wherein the coloring agent further contains a green pigment.
<5> A film obtained from the colored composition according to any one of <1> to <4>.
<6> An optical filter having the film according to <5>.
<7> A solid-state imaging device having the film according to <5>.
<8> An image display device having the film according to <5>.
<9> Compound represented by formula (1);
In formula (1), X 1 represents N or CR 8 ,
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。
<2> 上記式(1)において、R7が電子求引性基であり、X1がCR8であり、R8が酸基または塩基性基を含む、<1>に記載の着色組成物。
<3> 上記式(1)において、R1およびR2は、それぞれ独立してアルキル基もしくはアリール基であるか、または、R1とR2が結合して環を形成している、<1>または<2>に記載の着色組成物。
<4> 上記着色剤は、更に、緑色顔料を含む、<1>~<3>のいずれか1つに記載の着色組成物。
<5> <1>~<4>のいずれか1つに記載の着色組成物から得られる膜。
<6> <5>に記載の膜を有する光学フィルタ。
<7> <5>に記載の膜を有する固体撮像素子。
<8> <5>に記載の膜を有する画像表示装置。
<9> 式(1)で表される化合物;
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。 <1> A coloring composition containing a coloring agent containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent;
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
<2> The colored composition according to <1>, wherein in the formula (1), R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains an acid group or a basic group. .
<3> In the above formula (1), R 1 and R 2 are each independently an alkyl group or an aryl group, or R 1 and R 2 are combined to form a ring, <1 > or the colored composition described in <2>.
<4> The colored composition according to any one of <1> to <3>, wherein the coloring agent further contains a green pigment.
<5> A film obtained from the colored composition according to any one of <1> to <4>.
<6> An optical filter having the film according to <5>.
<7> A solid-state imaging device having the film according to <5>.
<8> An image display device having the film according to <5>.
<9> Compound represented by formula (1);
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
本発明は、温度変動のある環境下でも欠陥の発生が抑制された膜を製造可能な着色組成物を提供することができる。また、本発明は、膜、光学フィルタ、固体撮像素子、画像表示装置および化合物を提供することができる。
The present invention can provide a colored composition that can produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Further, the present invention can provide a film, an optical filter, a solid-state imaging device, an image display device, and a compound.
以下において、本発明の内容について詳細に説明する。
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表し、Bnはベンジル基を表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。 The content of the present invention will be explained in detail below.
In this specification, "~" is used to include the numerical values described before and after it as a lower limit and an upper limit.
In the description of a group (atomic group) in this specification, the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group). For example, the term "alkyl group" includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In this specification, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified. Examples of the light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
In the present specification, "(meth)acrylate" represents acrylate and/or methacrylate, "(meth)acrylic" represents both acrylic and/or methacrylic, and "(meth)acrylate" represents acrylic and/or methacrylate. ) "Acryloyl" refers to either or both of acryloyl and methacryloyl.
In this specification, Me in the structural formula represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, Ph represents a phenyl group, and Bn represents a benzyl group.
In this specification, the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
In this specification, the total solid content refers to the total mass of all components of the composition excluding the solvent.
In this specification, pigment means a compound that is difficult to dissolve in a solvent.
In this specification, the term "process" is used not only to refer to an independent process, but also to include a process in which the intended effect of the process is achieved even if the process cannot be clearly distinguished from other processes. .
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表し、Bnはベンジル基を表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。 The content of the present invention will be explained in detail below.
In this specification, "~" is used to include the numerical values described before and after it as a lower limit and an upper limit.
In the description of a group (atomic group) in this specification, the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group). For example, the term "alkyl group" includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In this specification, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified. Examples of the light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
In the present specification, "(meth)acrylate" represents acrylate and/or methacrylate, "(meth)acrylic" represents both acrylic and/or methacrylic, and "(meth)acrylate" represents acrylic and/or methacrylate. ) "Acryloyl" refers to either or both of acryloyl and methacryloyl.
In this specification, Me in the structural formula represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, Ph represents a phenyl group, and Bn represents a benzyl group.
In this specification, the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
In this specification, the total solid content refers to the total mass of all components of the composition excluding the solvent.
In this specification, pigment means a compound that is difficult to dissolve in a solvent.
In this specification, the term "process" is used not only to refer to an independent process, but also to include a process in which the intended effect of the process is achieved even if the process cannot be clearly distinguished from other processes. .
<着色組成物>
本発明の着色組成物は、イソインドリン顔料を含む着色剤と、式(1)で表される化合物と、樹脂と、溶剤と、を含むことを特徴とする。 <Colored composition>
The colored composition of the present invention is characterized by containing a coloring agent containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent.
本発明の着色組成物は、イソインドリン顔料を含む着色剤と、式(1)で表される化合物と、樹脂と、溶剤と、を含むことを特徴とする。 <Colored composition>
The colored composition of the present invention is characterized by containing a coloring agent containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent.
本発明の着色組成物によれば、温度変動のある環境下でも欠陥の発生が抑制された膜を製造することができる。このような効果が得られる詳細な理由は不明であるが、以下によるものであると推測される。
本発明の着色組成物に含まれる式(1)で表される化合物は、イソインドリン顔料と相互作用してイソインドリン顔料に吸着すると推測される。また、式(1)で表される化合物に含まれる酸基または塩基性基は、樹脂と相互作用して樹脂に吸着すると推測される。このため、膜中において、イソインドリン顔料-式(1)で表される化合物-樹脂のネットワークが形成され易くなって、膜中でのイソインドリン顔料の凝集や、結晶成長を抑制することができると推測される。このため、本発明の着色組成物は、温度変動のある環境下でも欠陥の発生が抑制された膜を製造することができたと推測される。 According to the colored composition of the present invention, it is possible to produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Although the detailed reason for obtaining such an effect is unknown, it is presumed to be due to the following.
It is presumed that the compound represented by formula (1) contained in the coloring composition of the present invention interacts with the isoindoline pigment and is adsorbed to the isoindoline pigment. Further, it is assumed that the acid group or basic group contained in the compound represented by formula (1) interacts with the resin and is adsorbed to the resin. Therefore, a network of the isoindoline pigment, the compound represented by formula (1), and the resin is easily formed in the film, making it possible to suppress aggregation and crystal growth of the isoindoline pigment in the film. It is assumed that. Therefore, it is presumed that the colored composition of the present invention was able to produce a film in which the occurrence of defects was suppressed even in an environment with temperature fluctuations.
本発明の着色組成物に含まれる式(1)で表される化合物は、イソインドリン顔料と相互作用してイソインドリン顔料に吸着すると推測される。また、式(1)で表される化合物に含まれる酸基または塩基性基は、樹脂と相互作用して樹脂に吸着すると推測される。このため、膜中において、イソインドリン顔料-式(1)で表される化合物-樹脂のネットワークが形成され易くなって、膜中でのイソインドリン顔料の凝集や、結晶成長を抑制することができると推測される。このため、本発明の着色組成物は、温度変動のある環境下でも欠陥の発生が抑制された膜を製造することができたと推測される。 According to the colored composition of the present invention, it is possible to produce a film in which the occurrence of defects is suppressed even in an environment with temperature fluctuations. Although the detailed reason for obtaining such an effect is unknown, it is presumed to be due to the following.
It is presumed that the compound represented by formula (1) contained in the coloring composition of the present invention interacts with the isoindoline pigment and is adsorbed to the isoindoline pigment. Further, it is assumed that the acid group or basic group contained in the compound represented by formula (1) interacts with the resin and is adsorbed to the resin. Therefore, a network of the isoindoline pigment, the compound represented by formula (1), and the resin is easily formed in the film, making it possible to suppress aggregation and crystal growth of the isoindoline pigment in the film. It is assumed that. Therefore, it is presumed that the colored composition of the present invention was able to produce a film in which the occurrence of defects was suppressed even in an environment with temperature fluctuations.
本発明の着色組成物は、カラーフィルタ用または赤外線透過フィルタ用の着色組成物として好ましく用いられ、カラーフィルタ用の着色組成物としてより好ましく用いられる。より詳しくは、カラーフィルタの画素形成用の着色組成物や、赤外線透過フィルタ形成用の着色組成物として好ましく用いることができ、カラーフィルタの画素形成用の着色組成物としてより好ましく用いられる。カラーフィルタにおける画素の種類としては、赤色画素、緑色画素、青色画素、マゼンタ色画素、シアン色画素、黄色画素などが挙げられ、赤色画素、緑色画素または黄色画素であることが好ましく、赤色画素または緑色画素であることがより好ましく、緑色画素であることが更に好ましい。
The coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters, and more preferably used as a coloring composition for color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and more preferably used as a coloring composition for forming pixels of a color filter. Types of pixels in the color filter include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc., and preferably red pixels, green pixels, or yellow pixels; It is more preferable that the pixel is a green pixel, and even more preferable that it is a green pixel.
本発明の着色組成物を用いて厚さ0.65μmの膜を形成した際に、膜の光透過率が50%となる波長が、470~520nmの波長範囲に存在することが好ましく、475~520nmの波長範囲に存在することがより好ましく、480~520nmの波長範囲に存在することが更に好ましい。なかでも、光透過率が50%となる波長が、470~520nmの波長範囲と、575~625nmの波長範囲のそれぞれに存在することが好ましい。この態様において、光透過率が50%となる短波長側の波長は、475~520nmの波長範囲に存在することが好ましく、480~520nmの波長範囲に存在することがより好ましい。また、光透過率が50%となる長波長側の波長は、580~620nmの波長範囲に存在することが好ましく、585~615nmの波長範囲に存在することがより好ましい。このような分光特性を有する膜を形成できる着色組成物は、カラーフィルタの緑色画素形成用の着色組成物として好ましく用いられる。
When a film with a thickness of 0.65 μm is formed using the colored composition of the present invention, the wavelength at which the light transmittance of the film becomes 50% is preferably in the wavelength range of 470 to 520 nm, and preferably 475 to 520 nm. It is more preferable that it exists in the wavelength range of 520 nm, and even more preferably that it exists in the wavelength range of 480 to 520 nm. Among these, it is preferable that the wavelength at which the light transmittance is 50% exists in the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the short wavelength at which the light transmittance is 50% is preferably in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side at which the light transmittance is 50% is preferably in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm. A colored composition capable of forming a film having such spectral characteristics is preferably used as a colored composition for forming green pixels of a color filter.
以下、本発明の着色組成物に用いられる各成分について説明する。
Hereinafter, each component used in the colored composition of the present invention will be explained.
<<着色剤>>
本発明の着色組成物は着色剤を含有する。着色剤には、顔料を含むものが用いられる。より具体的には着色剤には、イソインドリン顔料を含むものが用いられる。 <<Colorant>>
The colored composition of the present invention contains a coloring agent. The coloring agent used includes a pigment. More specifically, the coloring agent used includes an isoindoline pigment.
本発明の着色組成物は着色剤を含有する。着色剤には、顔料を含むものが用いられる。より具体的には着色剤には、イソインドリン顔料を含むものが用いられる。 <<Colorant>>
The colored composition of the present invention contains a coloring agent. The coloring agent used includes a pigment. More specifically, the coloring agent used includes an isoindoline pigment.
顔料の平均一次粒子径は、1~200nmが好ましい。下限は5nm以上が好ましく、10nm以上がより好ましい。上限は、180nm以下が好ましく、150nm以下がより好ましく、100nm以下が更に好ましい。なお、本明細書において、顔料の一次粒子径は、顔料の一次粒子を透過型電子顕微鏡により観察し、得られた写真から求めることができる。具体的には、顔料の一次粒子の投影面積を求め、それに対応する円相当径を顔料の一次粒子径として算出する。また、本発明における平均一次粒子径は、400個の顔料の一次粒子についての一次粒子径の算術平均値とする。また、顔料の一次粒子とは、凝集のない独立した粒子をいう。
The average primary particle diameter of the pigment is preferably 1 to 200 nm. The lower limit is preferably 5 nm or more, more preferably 10 nm or more. The upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less. In addition, in this specification, the primary particle diameter of a pigment can be calculated|required from the photograph obtained by observing the primary particle of a pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circular equivalent diameter is calculated as the primary particle diameter of the pigment. Further, the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 pigment primary particles. Moreover, the primary particles of pigment refer to independent particles without agglomeration.
顔料の、CuKα線をX線源としたときのX線回折スペクトルにおけるいずれかの結晶面に由来するピークの半値幅より求めた結晶子サイズは、0.1~100nmであることが好ましく、0.5~50nmであることがより好ましく、1~30nmであることが更に好ましく、5~25nmであることが特に好ましい。
The crystallite size determined from the half-value width of the peak derived from any crystal plane in the X-ray diffraction spectrum of the pigment when CuKα rays are used as the X-ray source is preferably 0.1 to 100 nm, and 0. It is more preferably .5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
顔料の比表面積は1~300m2/gであることが好ましい。下限は10m2/g以上であることが好ましく、30m2/g以上であることがより好ましい。上限は、250m2/g以下であることが好ましく、200m2/g以下であることがより好ましい。比表面積の値は、BET(Brunauer、EmmettおよびTeller)法に準じてDIN 66131:determination of the specific surface area of solids by gas adsorption(ガス吸着による固体の比表面積の測定)に従って測定することができる。
The specific surface area of the pigment is preferably 1 to 300 m 2 /g. The lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more. The upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less. The value of the specific surface area is determined according to DIN 66131: determination of the specific surface area of solids by gas adsorption according to the BET (Brunauer, Emmett and Teller) method. (Measurement of specific surface area of solids).
(イソインドリン顔料)
本発明の着色組成物はイソインドリン顔料を含む。イソインドリン顔料は黄色顔料であることが好ましい。イソインドリン顔料は、ピラゾリジンジオン構造を有するイソインドリン顔料であることが好ましい。ピラゾリジンジオン構造を有するイソインドリン顔料としては、式(PI-1)で表される化合物が挙げられる。なお、式(PI-1)におけるXP1とRP7との波線の結合は、式(PI-1)のようにRP7が下側(RP6側)にあってもよく、あるいは、RP7が上側(RP9側)にあってもよいことを意味する。
(isoindoline pigment)
The coloring composition of the present invention contains an isoindoline pigment. Preferably, the isoindoline pigment is a yellow pigment. The isoindoline pigment is preferably an isoindoline pigment having a pyrazolidinedione structure. Examples of the isoindoline pigment having a pyrazolidinedione structure include a compound represented by formula (PI-1). Note that the bond of the wavy line between X P1 and R P7 in formula (PI-1) may be such that R P7 is on the lower side (R P6 side) as in formula (PI-1), or R P7 may be on the lower side (R P6 side). This means that it may be on the upper side ( RP9 side).
本発明の着色組成物はイソインドリン顔料を含む。イソインドリン顔料は黄色顔料であることが好ましい。イソインドリン顔料は、ピラゾリジンジオン構造を有するイソインドリン顔料であることが好ましい。ピラゾリジンジオン構造を有するイソインドリン顔料としては、式(PI-1)で表される化合物が挙げられる。なお、式(PI-1)におけるXP1とRP7との波線の結合は、式(PI-1)のようにRP7が下側(RP6側)にあってもよく、あるいは、RP7が上側(RP9側)にあってもよいことを意味する。
The coloring composition of the present invention contains an isoindoline pigment. Preferably, the isoindoline pigment is a yellow pigment. The isoindoline pigment is preferably an isoindoline pigment having a pyrazolidinedione structure. Examples of the isoindoline pigment having a pyrazolidinedione structure include a compound represented by formula (PI-1). Note that the bond of the wavy line between X P1 and R P7 in formula (PI-1) may be such that R P7 is on the lower side (R P6 side) as in formula (PI-1), or R P7 may be on the lower side (R P6 side). This means that it may be on the upper side ( RP9 side).
式(PI-1)中、XP1は、NまたはCRP8を表し、
RP1~RP9はそれぞれ独立して、水素原子または置換基を表し、
RP1~RP8の2以上が結合して環を形成していてもよい。 In formula (PI-1), X P1 represents N or CR P8 ,
R P1 to R P9 each independently represent a hydrogen atom or a substituent,
Two or more of R P1 to R P8 may be bonded to form a ring.
RP1~RP9はそれぞれ独立して、水素原子または置換基を表し、
RP1~RP8の2以上が結合して環を形成していてもよい。 In formula (PI-1), X P1 represents N or CR P8 ,
R P1 to R P9 each independently represent a hydrogen atom or a substituent,
Two or more of R P1 to R P8 may be bonded to form a ring.
式(PI-1)のRP1~RP9が表す置換基としては、ハロゲン原子、ヒドロキシ基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。更なる置換基としては、ハロゲン原子、ヒドロキシ基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。
Substituents represented by R P1 to R P9 in formula (PI-1) include a halogen atom, a hydroxy group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, and an alkoxycarbonyl group. , an alkylthio group, an arylthio group and a morpholino group. These groups may further have a substituent when the group is a substitutable group. Additional substituents include halogen atoms, hydroxy groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. It will be done.
式(PI-1)のRP1およびRP2は、それぞれ独立して、水素原子、アルキル基またはアリール基であることが好ましく、アルキル基またはアリール基であることがより好ましく、アルキル基であることが更に好ましい。また、RP1およびRP2は、同じ基であることが好ましい。
アルキル基の炭素数は、1~10が好ましく、1~4がより好ましく、1または2が更に好ましい。アルキル基は、直鎖状、分岐状、環状のいずれでもよいが、直鎖状または分岐状が好ましく、直鎖状がより好ましい。アルキル基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基等が挙げられる。
アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基等が挙げられる。 R P1 and R P2 in formula (PI-1) are each independently preferably a hydrogen atom, an alkyl group or an aryl group, more preferably an alkyl group or an aryl group, and are an alkyl group. is even more preferable. Moreover, it is preferable that R P1 and R P2 are the same group.
The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2. The alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, a hydroxy group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent. Examples of the substituent include a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
アルキル基の炭素数は、1~10が好ましく、1~4がより好ましく、1または2が更に好ましい。アルキル基は、直鎖状、分岐状、環状のいずれでもよいが、直鎖状または分岐状が好ましく、直鎖状がより好ましい。アルキル基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基等が挙げられる。
アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基等が挙げられる。 R P1 and R P2 in formula (PI-1) are each independently preferably a hydrogen atom, an alkyl group or an aryl group, more preferably an alkyl group or an aryl group, and are an alkyl group. is even more preferable. Moreover, it is preferable that R P1 and R P2 are the same group.
The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2. The alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, a hydroxy group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent. Examples of the substituent include a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an alkylthio group, an arylthio group, and a morpholino group.
RP1およびRP2は、それぞれ独立して、水素原子、メチル基、フェニル基またはベンジル基であることが好ましく、メチル基、フェニル基またはベンジル基であることがより好ましい。
R P1 and R P2 are each independently preferably a hydrogen atom, a methyl group, a phenyl group, or a benzyl group, and more preferably a methyl group, a phenyl group, or a benzyl group.
式(PI-1)のRP1とRP2は結合して環を形成していてもよい。形成される環は、5員環または6員環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基等が挙げられる。
R P1 and R P2 in formula (PI-1) may be combined to form a ring. The ring formed is preferably a 5-membered ring or a 6-membered ring. The ring formed may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
式(PI-1)のRP3~RP6は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基またはアルコキシカルボニル基であることが好ましく、水素原子、アルキル基またはアルコキシ基であることがより好ましく、水素原子であることが更に好ましい。
上記のアルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P3 to R P6 in formula (PI-1) each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, It is preferably a carbamoyl group or an alkoxycarbonyl group, more preferably a hydrogen atom, an alkyl group or an alkoxy group, and even more preferably a hydrogen atom.
The above alkyl group, aryl group, alkoxy group, heteroaryl group, acyl group, carbamoyl group, alkoxycarbonyl group, alkylthio group, arylthio group and morpholino group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
上記のアルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P3 to R P6 in formula (PI-1) each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, It is preferably a carbamoyl group or an alkoxycarbonyl group, more preferably a hydrogen atom, an alkyl group or an alkoxy group, and even more preferably a hydrogen atom.
The above alkyl group, aryl group, alkoxy group, heteroaryl group, acyl group, carbamoyl group, alkoxycarbonyl group, alkylthio group, arylthio group and morpholino group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
式(PI-1)のRP3~RP6の2以上が結合して環を形成していてもよい。形成される環は、芳香族環であることが好ましく、ベンゼン環であることがより好ましい。環を形成する場合は、RP4とRP5が結合して環を形成していることが好ましく、芳香族環を形成していることがより好ましく、ベンゼン環を形成していることが更に好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基等が挙げられる。
Two or more of R P3 to R P6 of formula (PI-1) may be bonded to form a ring. The ring formed is preferably an aromatic ring, more preferably a benzene ring. When forming a ring, R P4 and R P5 are preferably combined to form a ring, more preferably an aromatic ring, and even more preferably a benzene ring. . The formed ring may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
式(PI-1)のRP7は、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、電子求引性基であることがより好ましい。電子求引性基としては、シアノ基、カルバモイル基、およびアシル基が挙げられ、シアノ基であることが好ましい。
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基およびアルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P7 in formula (PI-1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and is an electron-withdrawing group. It is more preferable that there be. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基およびアルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P7 in formula (PI-1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and is an electron-withdrawing group. It is more preferable that there be. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
式(PI-1)のXP1は、CRP8であることが好ましい。また、RP8は、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、電子求引性基であることがより好ましい。電子求引性基としては、シアノ基、カルバモイル基、およびアシル基が挙げられ、シアノ基であることが好ましい。
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基およびアルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 X P1 in formula (PI-1) is preferably CR P8 . Further, R P8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and more preferably an electron-withdrawing group. . Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基およびアルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 X P1 in formula (PI-1) is preferably CR P8 . Further, R P8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and more preferably an electron-withdrawing group. . Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group and alkoxycarbonyl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
式(PI-1)のXP1がCRP8である場合、RP7とRP8は結合して環を形成していてもよい。形成される環は、ピラゾリジンジオン環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基等が挙げられる。
When X P1 in formula (PI-1) is CR P8 , R P7 and R P8 may be combined to form a ring. The ring formed is preferably a pyrazolidinedione ring. The ring formed may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
式(PI-1)は、XP1がCRP8であり、かつ、RP7およびRP8の少なくとも1つが電子求引性基であることが好ましく、RP7およびRP8がともに電子求引性基であることがより好ましい。
In formula (PI-1), X P1 is CR P8 , and at least one of R P7 and R P8 is preferably an electron-withdrawing group, and R P7 and R P8 are both electron-withdrawing groups. It is more preferable that
式(PI-1)のRP9は、水素原子、アルキル基、アリール基、または、ヘテロアリール基であることが好ましく、水素原子、アルキル基、または、アリール基であることがより好ましく、水素原子であることが更に好ましい。
上記のアルキル基、アリール基、および、ヘテロアリール基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P9 in formula (PI-1) is preferably a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, or an aryl group; It is more preferable that
The above alkyl group, aryl group, and heteroaryl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
上記のアルキル基、アリール基、および、ヘテロアリール基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基などが挙げられる。 R P9 in formula (PI-1) is preferably a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, or an aryl group; It is more preferable that
The above alkyl group, aryl group, and heteroaryl group may further have a substituent. Additional substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups.
式(PI-1)で表される化合物は、式(PI-2)または式(PI-3)で表される化合物であることが好ましく、式(PI-2)で表される化合物であることがより好ましい。なお、式(PI-2)におけるRP17およびRP18をつなぐ波線の結合は、式(PI-2)のようにRP17が下側(RP16側)で、RP18が上側(RP19側)であってもよく、あるいは、RP18が下側(RP16側)で、RP17が上側(RP19側)であってもよいことを意味する。
The compound represented by formula (PI-1) is preferably a compound represented by formula (PI-2) or formula (PI-3), and is preferably a compound represented by formula (PI-2). It is more preferable. Note that the bond of the wavy line connecting R P17 and R P18 in formula (PI-2) is that R P17 is on the lower side (R P16 side) and R P18 is on the upper side (R P19 side). ), or it means that R P18 may be on the lower side (R P16 side) and R P17 may be on the upper side (R P19 side).
式(PI-2)中、RP11~RP19はそれぞれ独立して、水素原子または置換基を表し、RP11~RP16の2以上が結合して環を形成していてもよい;
式(PI-3)中、RP21~RP29はそれぞれ独立して、水素原子または置換基を表し、RP21~RP28の2以上が結合して環を形成していてもよい; In formula (PI-2), R P11 to R P19 each independently represent a hydrogen atom or a substituent, and two or more of R P11 to R P16 may be bonded to form a ring;
In formula (PI-3), R P21 to R P29 each independently represent a hydrogen atom or a substituent, and two or more of R P21 to R P28 may be bonded to form a ring;
式(PI-3)中、RP21~RP29はそれぞれ独立して、水素原子または置換基を表し、RP21~RP28の2以上が結合して環を形成していてもよい; In formula (PI-2), R P11 to R P19 each independently represent a hydrogen atom or a substituent, and two or more of R P11 to R P16 may be bonded to form a ring;
In formula (PI-3), R P21 to R P29 each independently represent a hydrogen atom or a substituent, and two or more of R P21 to R P28 may be bonded to form a ring;
式(PI-2)のRP11~RP16および式(PI-3)のRP21~RP26は、式(PI-1)のRP1~RP6と同義であり、好ましい範囲も同様である。
式(PI-2)のRP19および式(PI-3)のRP29は、式(PI-1)のRP9と同義であり、好ましい範囲も同様である。 R P11 to R P16 of formula (PI-2) and R P21 to R P26 of formula (PI-3) have the same meaning as R P1 to R P6 of formula (PI-1), and their preferred ranges are also the same. .
R P19 in formula (PI-2) and R P29 in formula (PI-3) have the same meaning as R P9 in formula (PI-1), and the preferred ranges are also the same.
式(PI-2)のRP19および式(PI-3)のRP29は、式(PI-1)のRP9と同義であり、好ましい範囲も同様である。 R P11 to R P16 of formula (PI-2) and R P21 to R P26 of formula (PI-3) have the same meaning as R P1 to R P6 of formula (PI-1), and their preferred ranges are also the same. .
R P19 in formula (PI-2) and R P29 in formula (PI-3) have the same meaning as R P9 in formula (PI-1), and the preferred ranges are also the same.
式(PI-2)のRP17およびRP18は、それぞれ独立してアルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、電子求引性基であることがより好ましい。電子求引性基としては、シアノ基、カルバモイル基およびアシル基が挙げられ、シアノ基であることが好ましい。
Preferably, R P17 and R P18 in formula (PI-2) are each independently an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group. , more preferably an electron-withdrawing group. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group, with a cyano group being preferred.
式(PI-3)のRP27およびRP28の好ましい態様は、式(PI-1)のRP1およびRP2の好ましい態様と同様である。
Preferred embodiments of R P27 and R P28 in formula (PI-3) are the same as preferred embodiments of R P1 and R P2 in formula (PI-1).
式(PI-3)のRP27とRP28は結合して環を形成していてもよい。形成される環は、5員環または6員環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基およびモルフォリノ基等が挙げられる。
R P27 and R P28 in formula (PI-3) may be combined to form a ring. The ring formed is preferably a 5-membered ring or a 6-membered ring. The formed ring may have a substituent. Examples of substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, and morpholino groups. Can be mentioned.
式(PI-3)において、RP21、RP22、RP27およびRP28はいずれも同じ基であることが好ましい。
In formula (PI-3), R P21 , R P22 , R P27 and R P28 are preferably all the same group.
式(PI-1)で表される化合物は、波長400nm~700nmの範囲に極大吸収を有する化合物であることが好ましく、波長400nm~600nmの範囲に極大吸収を有する化合物であることがより好ましく、波長400nm~500nmの範囲に極大吸収を有する化合物であることが特に好ましい。
The compound represented by formula (PI-1) is preferably a compound having maximum absorption in the wavelength range of 400 nm to 700 nm, more preferably a compound having maximum absorption in the wavelength range of 400 nm to 600 nm, Particularly preferred is a compound having maximum absorption in the wavelength range of 400 nm to 500 nm.
式(PI-1)で表される化合物の具体例としては、後述する実施例において用いられる化合物(Y-1)~(Y-7)が挙げられる。
Specific examples of the compound represented by formula (PI-1) include compounds (Y-1) to (Y-7) used in the examples described below.
本発明において、イソインドリン顔料には、C.I.ピグメントイエロー139、185などを用いることもできる。
In the present invention, the isoindoline pigment contains C. I. Pigment Yellow 139, 185, etc. can also be used.
(他の着色剤)
本発明の着色組成物は、イソインドリン顔料以外の着色剤を更に含有することができる。他の着色剤としては、黄色着色剤、オレンジ色着色剤、赤色着色剤、緑色着色剤、紫色着色剤および青色着色剤などが挙げられる。他の着色剤は、顔料であってもよく、染料であってもよい。顔料は、無機顔料または有機顔料のいずれでもよいが、カラーバリエーションの多さ、分散の容易性、安全性等の観点から有機顔料であることが好ましい。 (Other colorants)
The colored composition of the present invention can further contain a coloring agent other than the isoindoline pigment. Other colorants include yellow colorants, orange colorants, red colorants, green colorants, purple colorants, blue colorants, and the like. Other colorants may be pigments or dyes. The pigment may be either an inorganic pigment or an organic pigment, but organic pigments are preferable from the viewpoint of wide color variations, ease of dispersion, safety, and the like.
本発明の着色組成物は、イソインドリン顔料以外の着色剤を更に含有することができる。他の着色剤としては、黄色着色剤、オレンジ色着色剤、赤色着色剤、緑色着色剤、紫色着色剤および青色着色剤などが挙げられる。他の着色剤は、顔料であってもよく、染料であってもよい。顔料は、無機顔料または有機顔料のいずれでもよいが、カラーバリエーションの多さ、分散の容易性、安全性等の観点から有機顔料であることが好ましい。 (Other colorants)
The colored composition of the present invention can further contain a coloring agent other than the isoindoline pigment. Other colorants include yellow colorants, orange colorants, red colorants, green colorants, purple colorants, blue colorants, and the like. Other colorants may be pigments or dyes. The pigment may be either an inorganic pigment or an organic pigment, but organic pigments are preferable from the viewpoint of wide color variations, ease of dispersion, safety, and the like.
他の着色剤は、黄色顔料、オレンジ色顔料、赤色顔料、緑色顔料、紫色顔料および青色顔料から選ばれる少なくとも1種を含むことが好ましく、緑色顔料、黄色顔料および赤色顔料から選ばれる少なくとも1種を含むことがより好ましく、緑色顔料を少なくとも含むことが特に好ましい。
The other coloring agent preferably includes at least one selected from a yellow pigment, an orange pigment, a red pigment, a green pigment, a purple pigment, and a blue pigment, and at least one selected from a green pigment, a yellow pigment, and a red pigment. It is more preferable that it contains, and it is especially preferable that it contains at least a green pigment.
赤色着色剤としては、ジケトピロロピロール化合物、アントラキノン化合物、アゾ化合物、ナフトール化合物、アゾメチン化合物、キサンテン化合物、キナクリドン化合物、ペリレン化合物、チオインジゴ化合物などが挙げられ、ジケトピロロピロール化合物、アントラキノン化合物、アゾ化合物であることが好ましく、ジケトピロロピロール化合物であることがより好ましい。また、赤色着色剤は赤色顔料であることが好ましい。また、赤色顔料は、ジケトピロロピロール顔料であることが好ましい。
Examples of red colorants include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, etc. It is preferably a compound, and more preferably a diketopyrrolopyrrole compound. Moreover, it is preferable that the red colorant is a red pigment. Moreover, it is preferable that the red pigment is a diketopyrrolopyrrole pigment.
赤色着色剤の具体例としては、C.I.(カラーインデックス)ピグメントレッド1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294,295,296,297等の赤色顔料が挙げられる。また、赤色着色剤として、国際公開第2022/085485号の段落番号0034に記載の化合物、特開2020-085947号公報に記載の臭素化ジケトピロロピロール化合物を用いることもできる。
Specific examples of red colorants include C.I. I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, Examples include red pigments such as 279, 291, 294, 295, 296, 297, and the like. Further, as a red colorant, a compound described in paragraph number 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP 2020-085947 can also be used.
赤色着色剤としては、C.I.ピグメントレッド122,177,224,254,255,264,269,272が好ましく、C.I.ピグメントレッド254,264,272がより好ましく、C.I.ピグメントレッド254,264が更に好ましい。
As the red colorant, C. I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272 are preferred, and C.I. I. Pigment Red 254, 264, and 272 are more preferred, and C.I. I. Pigment Red 254 and 264 are more preferred.
緑色着色剤としては、フタロシアニン化合物、スクアリリウム化合物などが挙げられ、フタロシアニン化合物であることが好ましい。また、緑色着色剤は緑色顔料であることが好ましい。また、緑色顔料は、フタロシアニン顔料であることが好ましい。
Examples of the green coloring agent include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. Moreover, it is preferable that the green coloring agent is a green pigment. Moreover, it is preferable that the green pigment is a phthalocyanine pigment.
緑色着色剤の具体例としては、C.I.ピグメントグリーン7,10,36,37,58,59,62,63,64,65,66等の緑色顔料が挙げられる。また、緑色着色剤として、1分子中のハロゲン原子数が平均10~14個であり、臭素原子数が平均8~12個であり、塩素原子数が平均2~5個であるハロゲン化亜鉛フタロシアニン顔料を用いることもできる。具体例としては、国際公開第2015/118720号に記載の化合物が挙げられる。また、緑色着色剤として国際公開第2022/085485号の段落番号0029に記載の化合物、特開2020-070426号公報に記載のアルミニウムフタロシアニン化合物、特表2020-504758号公報に記載のジアリールメタン化合物などを用いることもできる。
Specific examples of green colorants include C.I. I. Examples include green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66. In addition, as a green coloring agent, halogenated zinc phthalocyanine has an average number of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720. In addition, as green colorants, compounds described in paragraph number 0029 of International Publication No. 2022/085485, aluminum phthalocyanine compounds described in JP-A-2020-070426, diarylmethane compounds described in Japanese Patent Publication No. 2020-504758, etc. You can also use
緑色着色剤としては、C.I.ピグメントグリーン7,36,58,62,63が好ましい。
As the green colorant, C. I. Pigment Green 7, 36, 58, 62, and 63 are preferred.
オレンジ色着色剤の具体例としては、C.I.ピグメントオレンジ2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73等のオレンジ色顔料が挙げられる。
Specific examples of orange colorants include C.I. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. orange pigments.
黄色着色剤としては、アゾ化合物、アゾメチン化合物、イソインドリン化合物、プテリジン化合物、キノフタロン化合物およびペリレン化合物が挙げられる。黄色着色剤は黄色顔料であることが好ましい。黄色着色剤の具体例としては、C.I.ピグメントイエロー1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97,98,100,101,104,106,108,113,114,115,116,117,118,119,120,123,125,126,127,128,129,137,138,147,148,150,151,152,153,154,155,156,161,162,164,166,168,169,170,171,172,174,175,176,177,180,181,182,187,188,193,194,199,213,214,215,228,231,232,233,234,235,236等の黄色顔料が挙げられる。
Examples of yellow colorants include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds. Preferably, the yellow colorant is a yellow pigment. Specific examples of yellow colorants include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 168, 169, 170, 171, 172, 174, 175, 176, 177, 180, 181, 182, 187, 188, 193, Examples include yellow pigments such as 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236.
また、黄色着色剤としては、下記構造のアゾバルビツール酸ニッケル錯体を用いることもできる。
Further, as the yellow coloring agent, an azobarbituric acid nickel complex having the following structure can also be used.
また、黄色着色剤として、国際公開第2022/085485号の段落番号0031~0033に記載の化合物、特開2019-073695号公報に記載のメチン染料、特開2019-073696号公報に記載のメチン染料を用いることができる。
In addition, as a yellow coloring agent, compounds described in paragraph numbers 0031 to 0033 of International Publication No. 2022/085485, methine dyes described in JP 2019-073695, methine dyes described in JP 2019-073696, can be used.
紫色着色剤の具体例としては、C.I.ピグメントバイオレット1,19,23,27,32,37,42,60,61等の紫色顔料が挙げられる。
Specific examples of purple colorants include C.I. I. Examples include purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
青色着色剤の具体例としては、C.I.ピグメントブルー1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87,88等の青色顔料が挙げられる。また、青色着色剤として、リン原子を有するアルミニウムフタロシアニン化合物を用いることもできる。具体例としては、特開2012-247591号公報の段落番号0022~0030、特開2011-157478号公報の段落番号0047に記載の化合物が挙げられる。
Specific examples of blue colorants include C.I. I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. Examples include pigments. Moreover, an aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant. Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A No. 2012-247591 and paragraph number 0047 of JP-A No. 2011-157478.
他の着色剤には染料を用いることもできる。染料としては特に制限はなく、公知の染料が使用できる。例えば、ピラゾールアゾ系、アニリノアゾ系、トリアリールメタン系、アントラキノン系、アントラピリドン系、ベンジリデン系、オキソノール系、ピラゾロトリアゾールアゾ系、ピリドンアゾ系、シアニン系、フェノチアジン系、ピロロピラゾールアゾメチン系、キサンテン系、フタロシアニン系、ベンゾピラン系、インジゴ系、ピロメテン系等の染料が挙げられる。
Dyes can also be used as other colorants. There are no particular restrictions on the dye, and known dyes can be used. For example, pyrazole azo series, anilinoazo series, triarylmethane series, anthraquinone series, anthrapyridone series, benzylidene series, oxonol series, pyrazolotriazole azo series, pyridone azo series, cyanine series, phenothiazine series, pyrrolopyrazole azomethine series, xanthene series, Examples include phthalocyanine-based, benzopyran-based, indigo-based, and pyrromethene-based dyes.
他の着色剤には、韓国公開特許第10-2020-0028160号公報に記載されたトリアリールメタン染料ポリマー、特開2020-117638号公報に記載のキサンテン化合物、国際公開第2020/174991号に記載のフタロシアニン化合物、特開2020-160279号公報に記載のイソインドリン化合物又はそれらの塩、韓国公開特許第10-2020-0069442号公報に記載の式1で表される化合物、韓国公開特許第10-2020-0069730号公報に記載の式1で表される化合物、韓国公開特許第10-2020-0069070号公報に記載の式1で表される化合物、韓国公開特許第10-2020-0069067号公報に記載の式1で表される化合物、韓国公開特許第10-2020-0069062号公報に記載の式1で表される化合物、特許第6809649号に記載のハロゲン化亜鉛フタロシアニン顔料、特開2020-180176号公報に記載のイソインドリン化合物、特開2021-187913号公報に記載のフェノチアジン系化合物、国際公開第2022/004261号に記載のハロゲン化亜鉛フタロシアニン、国際公開第2021/250883号に記載のハロゲン化亜鉛フタロシアニンを用いることができる。他の着色剤は、ロタキサンであってもよく、色素骨格はロタキサンの環状構造に使用されていてもよく、棒状構造に使用されていてもよく、両方の構造に使用されていてもよい。他の着色剤として、韓国公開特許第10-2020-0030759号公報の式1で表されるキノフタロン化合物、韓国公開特許第10-2020-0061793号公報に記載の高分子染料、特開2022-029701号公報に記載の着色剤、国際公開第2022/014635号に記載のイソインドリン化合物、国際公開第2022/024926号に記載のアルミニウムフタロシアニン化合物、特開2022-045895号公報に記載の化合物、国際公開第2022/050051号に記載の化合物を用いることもできる。
Other colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP2020-117638, and International Publication No. 2020/174991. phthalocyanine compounds, isoindoline compounds or their salts described in JP-A No. 2020-160279, compounds represented by formula 1 described in Korean Published Patent No. 10-2020-0069442, Korean Published Patent No. 10- Compounds represented by formula 1 described in Korean Publication No. 2020-0069730, compounds represented by formula 1 described in Korean Publication Patent No. 10-2020-0069070, and compounds represented by formula 1 described in Korean Publication Patent No. 10-2020-0069067. Compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigment described in Patent No. 6809649, JP 2020-180176 Isoindoline compounds described in JP-A No. 2021-187913, phenothiazine compounds described in JP-A No. 2021-187913, halogenated zinc phthalocyanine described in International Publication No. 2022/004261, and halogenated compounds described in International Publication No. 2021/250883. Zinc phthalocyanine can be used. The other colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, in the rod-like structure, or in both structures. Other colorants include a quinophthalone compound represented by formula 1 in Korean Patent Publication No. 10-2020-0030759, a polymer dye described in Korean Publication Patent No. 10-2020-0061793, and JP-A No. 2022-029701. The coloring agent described in WO 2022/014635, the aluminum phthalocyanine compound described in WO 2022/024926, the compound described in JP 2022-045895, WO Compounds described in No. 2022/050051 can also be used.
本発明の着色組成物が他の着色剤として緑色顔料などの緑色着色剤を含む場合は、本発明の着色組成物はカラーフィルタの緑色画素形成用の着色組成物として好ましく用いられる。また、本発明の着色組成物が他の着色剤として赤色顔料などの赤色着色剤を含む場合は、本発明の着色組成物はカラーフィルタの赤色画素形成用の着色組成物として好ましく用いられる。
When the coloring composition of the present invention contains a green colorant such as a green pigment as another colorant, the coloring composition of the present invention is preferably used as a coloring composition for forming green pixels of a color filter. Furthermore, when the coloring composition of the present invention contains a red colorant such as a red pigment as another colorant, the coloring composition of the present invention is preferably used as a coloring composition for forming red pixels of a color filter.
また、着色組成物に含まれる着色剤は、2種以上の有彩色着色剤を含み、かつ、2種以上の有彩色着色剤の組み合わせで黒色を形成していてもよい。このような着色組成物は、赤外線透過フィルタ形成用の着色組成物として好ましく用いられる。2種以上の有彩色着色剤の組み合わせで黒色を形成する場合の有彩色着色剤の組み合わせとしては以下が挙げられる。
(1)赤色着色剤と青色着色剤と黄色着色剤とを含有する態様。
(2)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤とを含有する態様。
(3)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤と緑色着色剤とを含有する態様。
(4)赤色着色剤と青色着色剤と黄色着色剤と緑色着色剤とを含有する態様。
(5)黄色着色剤と紫色着色剤とを含有する態様。 Moreover, the coloring agent contained in the coloring composition may include two or more types of chromatic coloring agents, and black may be formed by a combination of two or more types of chromatic coloring agents. Such a colored composition is preferably used as a colored composition for forming an infrared transmission filter. Examples of combinations of chromatic colorants in the case where black color is formed by a combination of two or more chromatic colorants include the following.
(1) Embodiment containing a red colorant, a blue colorant, and a yellow colorant.
(2) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
(3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant.
(4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
(5) Embodiment containing a yellow colorant and a purple colorant.
(1)赤色着色剤と青色着色剤と黄色着色剤とを含有する態様。
(2)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤とを含有する態様。
(3)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤と緑色着色剤とを含有する態様。
(4)赤色着色剤と青色着色剤と黄色着色剤と緑色着色剤とを含有する態様。
(5)黄色着色剤と紫色着色剤とを含有する態様。 Moreover, the coloring agent contained in the coloring composition may include two or more types of chromatic coloring agents, and black may be formed by a combination of two or more types of chromatic coloring agents. Such a colored composition is preferably used as a colored composition for forming an infrared transmission filter. Examples of combinations of chromatic colorants in the case where black color is formed by a combination of two or more chromatic colorants include the following.
(1) Embodiment containing a red colorant, a blue colorant, and a yellow colorant.
(2) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
(3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant.
(4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
(5) Embodiment containing a yellow colorant and a purple colorant.
着色組成物の全固形分中における着色剤の含有量は、40質量%以上であることが好ましく、50質量%以上であることがより好ましく、55質量%以上であることが更に好ましい。上限は、80質量%以下であることが好ましく、75質量%以下であることがより好ましく、70質量%以下であることが更に好ましく、65質量%以下であることがより一層好ましい。着色剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
The content of the coloring agent in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 55% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and even more preferably 65% by mass or less. Only one type of colorant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
着色組成物の全固形分中におけるイソインドリン顔料の含有量は、1質量%以上であることが好ましく、2質量%以上であることがより好ましく、5質量%以上であることが更に好ましい。上限は、80質量%以下であることが好ましく、75質量%以下であることがより好ましく、70質量%以下であることが更に好ましく、65質量%以下であることがより一層好ましい。イソインドリン顔料は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
The content of the isoindoline pigment in the total solid content of the coloring composition is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and even more preferably 65% by mass or less. Only one type of isoindoline pigment may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
着色剤中におけるイソインドリン顔料の含有量は、1質量%以上であることが好ましく、3質量%以上であることがより好ましく、5質量%以上であることが更に好ましい。上限は100質量%とすることができ、70質量%以下とすることもでき、50質量%以下とすることもできる。
The content of the isoindoline pigment in the colorant is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. The upper limit can be 100% by mass, 70% by mass or less, and 50% by mass or less.
本発明の着色組成物をカラーフィルタの緑色画素形成用の着色組成物として用いる場合、着色剤には黄色顔料と緑色顔料を含むものを用いることが好ましい。また、黄色顔料はイソインドリン顔料を含むものであることが好ましい。また、黄色顔料中におけるイソインドリン顔料の含有量は、20質量%以上であることが好ましく、25質量%以上であることがより好ましく、30質量%以上であることが更に好ましい。上限は100質量%とすることができ、95質量%以下とすることもでき、90質量%以下とすることもできる。また、黄色顔料と緑色顔料との質量比は、黄色顔料:緑色顔料=30:70~70:30であることが好ましく、30:70~60:40であることがより好ましく、30:70~50:50であることが更に好ましい。
When using the colored composition of the present invention as a colored composition for forming green pixels of a color filter, it is preferable to use a coloring agent containing a yellow pigment and a green pigment. Moreover, it is preferable that the yellow pigment contains an isoindoline pigment. Further, the content of the isoindoline pigment in the yellow pigment is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more. The upper limit can be 100% by mass, 95% by mass or less, and 90% by mass or less. Further, the mass ratio of the yellow pigment to the green pigment is preferably yellow pigment: green pigment = 30:70 to 70:30, more preferably 30:70 to 60:40, and 30:70 to More preferably, the ratio is 50:50.
本発明の着色組成物をカラーフィルタの赤色画素形成用の着色組成物として用いる場合、着色剤には黄色顔料と赤色顔料を含むものを用いることが好ましい。また、黄色顔料はイソインドリン顔料を含むものであることが好ましい。また、黄色顔料中におけるイソインドリン顔料の含有量は、20質量%以上であることが好ましく、25質量%以上であることがより好ましく、30質量%以上であることが更に好ましい。上限は100質量%とすることができ、95質量%以下とすることもでき、90質量%以下とすることもできる。また、黄色顔料と赤色顔料との質量比は、黄色顔料:赤色顔料=30:70~70:30であることが好ましく、30:70~60:40であることがより好ましく、30:70~50:50であることが更に好ましい。
When using the colored composition of the present invention as a colored composition for forming red pixels of a color filter, it is preferable to use a coloring agent containing a yellow pigment and a red pigment. Moreover, it is preferable that the yellow pigment contains an isoindoline pigment. Further, the content of the isoindoline pigment in the yellow pigment is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more. The upper limit can be 100% by mass, 95% by mass or less, and 90% by mass or less. Further, the mass ratio of the yellow pigment to the red pigment is preferably yellow pigment: red pigment = 30:70 to 70:30, more preferably 30:70 to 60:40, and 30:70 to More preferably, the ratio is 50:50.
本発明の着色組成物をカラーフィルタの黄色画素形成用の着色組成物として用いる場合、着色剤中における黄色顔料の含有量は30質量%以上であることが好ましく、40質量%以上であることがより好ましく、50質量%以上であることが更に好ましい。また、黄色顔料はイソインドリン顔料を含むものであることが好ましい。また、黄色顔料中におけるイソインドリン顔料の含有量は、20質量%以上であることが好ましく、25質量%以上であることがより好ましく、30質量%以上であることが更に好ましい。上限は100質量%とすることができ、95質量%以下とすることもでき、90質量%以下とすることもできる。
When the coloring composition of the present invention is used as a coloring composition for forming yellow pixels of a color filter, the content of yellow pigment in the colorant is preferably 30% by mass or more, and preferably 40% by mass or more. The content is more preferably 50% by mass or more. Moreover, it is preferable that the yellow pigment contains an isoindoline pigment. Further, the content of the isoindoline pigment in the yellow pigment is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more. The upper limit can be 100% by mass, 95% by mass or less, and 90% by mass or less.
<<式(1)で表される化合物(特定化合物)>>
本発明の着色組成物は、式(1)で表される化合物(以下、特定化合物ともいう)を含有する。特定化合物は、本発明の化合物でもある。特定化合物は、顔料(好ましくはイソインドリン顔料)の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。なお、式(1)におけるX1とR7との波線の結合は、式(1)のようにR7が下側(R6側)にあってもよく、あるいは、R7が上側(R9側)にあってもよいことを意味する。 <<Compound represented by formula (1) (specific compound)>>
The colored composition of the present invention contains a compound represented by formula (1) (hereinafter also referred to as a specific compound). Specific compounds are also compounds of the invention. The specific compound is used as a dispersion aid for pigments (preferably isoindoline pigments). A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition. Note that the bond of the wavy line between X 1 and R 7 in formula (1) may be such that R 7 is on the lower side (R 6 side) as in formula (1), or R 7 is on the upper side (R 6 side). 9 side).
本発明の着色組成物は、式(1)で表される化合物(以下、特定化合物ともいう)を含有する。特定化合物は、本発明の化合物でもある。特定化合物は、顔料(好ましくはイソインドリン顔料)の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。なお、式(1)におけるX1とR7との波線の結合は、式(1)のようにR7が下側(R6側)にあってもよく、あるいは、R7が上側(R9側)にあってもよいことを意味する。 <<Compound represented by formula (1) (specific compound)>>
The colored composition of the present invention contains a compound represented by formula (1) (hereinafter also referred to as a specific compound). Specific compounds are also compounds of the invention. The specific compound is used as a dispersion aid for pigments (preferably isoindoline pigments). A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition. Note that the bond of the wavy line between X 1 and R 7 in formula (1) may be such that R 7 is on the lower side (R 6 side) as in formula (1), or R 7 is on the upper side (R 6 side). 9 side).
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
式(1)のR1~R9が表す置換基としては、後述する置換基Tで挙げた基、酸基および塩基性基が挙げられる。
Examples of the substituents represented by R 1 to R 9 in formula (1) include the groups listed below for substituent T, acid groups, and basic groups.
酸基としては、カルボキシ基、スルホ基、リン酸基、ボロン酸基、イミド酸基およびこれらの塩等が挙げられる。塩を構成する原子または原子団としては、アルカリ金属イオン(Li+、Na+、K+など)、アルカリ土類金属イオン(Ca2+、Mg2+など)、アンモニウムイオン、イミダゾリウムイオン、ピリジニウムイオン、ホスホニウムイオンなどが挙げられる。イミド酸基は、-SO2NHSO2RX1、-CONHSO2RX2、-CONHCORX3または-SO2NHCORX4で表される基が好ましく、-SO2NHSO2RX1、-CONHSO2RX2、または-SO2NHCORX4で表される基がより好ましく、-SO2NHSO2RX1または-CONHSO2RX2が更に好ましい。RX1~RX4は、それぞれ独立に、アルキル基またはアリール基を表す。RX1~RX4が表すアルキル基およびアリール基は、置換基を有してもよい。置換基としてはハロゲン原子であることが好ましく、フッ素原子であることがより好ましい。RX1~RX4は、それぞれ独立に、フッ素原子を含むアルキル基またはフッ素原子を含むアリール基であることが好ましく、フッ素原子を含むアルキル基であることがより好ましい。フッ素原子を含むアルキル基の炭素数は1~10が好ましく、1~5がより好ましく、1~3が更に好ましい。フッ素原子を含むアリール基の炭素数は6~20が好ましく、6~12がより好ましく、6が更に好ましい。 酸基は、カルボキシ基、スルホ基、リン酸基、-SO2NHSO2Rf1で表される基、または、それらの塩であることが好ましい。-SO2NHSO2Rf1で表される基におけるRf1はフッ素原子を含むアルキル基またはフッ素原子を含むアリール基を表す。
Examples of the acid group include a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, an imide acid group, and salts thereof. Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions, imidazolium ions, pyridinium ions, Examples include phosphonium ions. The imidic acid group is preferably a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 ; or -SO 2 NHCOR X4 is more preferred, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 is even more preferred. R X1 to R X4 each independently represent an alkyl group or an aryl group. The alkyl group and aryl group represented by R X1 to R X4 may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom. R X1 to R X4 are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, and more preferably an alkyl group containing a fluorine atom. The number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6. The acid group is preferably a carboxy group, a sulfo group, a phosphoric acid group, a group represented by -SO 2 NHSO 2 Rf 1 , or a salt thereof. Rf 1 in the group represented by -SO 2 NHSO 2 Rf 1 represents an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom.
塩基性基としては、アミノ基、ピリジニル基およびその塩、アンモニウム基の塩、並びにフタルイミドメチル基が挙げられる。塩を構成する原子または原子団としては、水酸化物イオン、ハロゲンイオン、カルボン酸イオン、スルホン酸イオン、フェノキシドイオンなどが挙げられる。塩基性基は、アミノ基であることが好ましい。
Examples of the basic group include an amino group, a pyridinyl group and its salts, an ammonium group salt, and a phthalimidomethyl group. Examples of atoms or atomic groups constituting the salt include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions. The basic group is preferably an amino group.
アミノ基としては、-NRx11Rx12で表される基、および、環状アミノ基が挙げられる。
Examples of the amino group include a group represented by -NR x11 R x12 and a cyclic amino group.
-NRx11Rx12で表される基において、Rx11およびRx12は、それぞれ独立して、水素原子、アルキル基またはアリール基を表し、アルキル基であることが好ましい。すなわち、アミノ基は、ジアルキルアミノ基であることが好ましい。アルキル基の炭素数は、1~10が好ましく、1~5がより好ましく、1~3が更に好ましい。アルキル基は、直鎖状、分岐状、環状のいずれでもよいが、直鎖状または分岐状が好ましく、直鎖がより好ましい。アルキル基は、置換基を有していてもよい。置換基としては後述する置換基Tが挙げられる。アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては後述する置換基Tが挙げられる。
In the group represented by -NR x11 R x12 , R x11 and R x12 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and preferably an alkyl group. That is, the amino group is preferably a dialkylamino group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include the substituent T described below. The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent. Examples of the substituent include the substituent T described below.
式(1)のR1およびRは、それぞれ独立して、水素原子、アルキル基、アリール基、酸基または塩基性基であることが好ましく、水素原子、アルキル基またはアリール基であることがより好ましく、アルキル基であることが更に好ましい。また、R1およびR2は、同じ基であることが好ましい。
R 1 and R in formula (1) are each independently preferably a hydrogen atom, an alkyl group, an aryl group, an acid group, or a basic group, and more preferably a hydrogen atom, an alkyl group, or an aryl group. Preferably, an alkyl group is more preferable. Moreover, it is preferable that R 1 and R 2 are the same group.
R1およびR2が表すアルキル基の炭素数は、1~10が好ましく、1~4がより好ましく、1または2が更に好ましい。アルキル基は、直鎖状、分岐状、環状のいずれでもよいが、直鎖状または分岐状が好ましく、直鎖状がより好ましい。アルキル基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
The number of carbon atoms in the alkyl group represented by R 1 and R 2 is preferably 1 to 10, more preferably 1 to 4, and even more preferably 1 or 2. The alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Substituents include halogen atoms, hydroxy groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and bases. Examples include sexual groups.
アリール基の炭素数は、6~30が好ましく、6~20がより好ましく、6~12が更に好ましい。アリール基は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent. Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and bases. Examples include sexual groups.
式(1)のR1およびR2は、それぞれ独立して、水素原子、メチル基、フェニル基またはベンジル基であることが好ましく、メチル基、フェニル基またはベンジル基であることがより好ましい。
R 1 and R 2 in formula (1) are each independently preferably a hydrogen atom, a methyl group, a phenyl group, or a benzyl group, and more preferably a methyl group, a phenyl group, or a benzyl group.
式(1)のR1とR2は結合して環を形成していてもよい。形成される環は、5員環または6員環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
R 1 and R 2 in formula (1) may be combined to form a ring. The ring formed is preferably a 5-membered ring or a 6-membered ring. The formed ring may have a substituent. Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
式(1)のR3~R6は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、酸基または塩基性基であることが好ましく、水素原子、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基またはアルコキシカルボニル基であることがより好ましく、水素原子、アルキル基またはアルコキシ基であることが更に好ましく、水素原子であることが特に好ましい。
R 3 to R 6 in formula (1) each independently represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, or a carbamoyl group. , an alkoxycarbonyl group, an acid group, or a basic group, including a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, and a carbamoyl group. or an alkoxycarbonyl group, more preferably a hydrogen atom, an alkyl group or an alkoxy group, and particularly preferably a hydrogen atom.
式(1)のR3~R6の2以上が結合して環を形成していてもよい。形成される環は、芳香族環であることが好ましく、ベンゼン環であることがより好ましい。環を形成する場合は、R4とR5が結合して環を形成していることが好ましく、芳香族環を形成していることがより好ましく、ベンゼン環を形成していることが更に好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
Two or more of R 3 to R 6 in formula (1) may be combined to form a ring. The ring formed is preferably an aromatic ring, more preferably a benzene ring. When forming a ring, R 4 and R 5 are preferably combined to form a ring, more preferably an aromatic ring, and even more preferably a benzene ring. . The ring formed may have a substituent. Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
式(1)のR7は、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、酸基または塩基性基であることが好ましく、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基またはアルコキシカルボニル基であることがより好ましく、電子求引性基であることが更に好ましい。電子求引性基としては、シアノ基、カルバモイル基、および、アシル基が挙げられる。
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基、および、アルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、後述する置換基Tで挙げた基、酸基および塩基性基が挙げられ、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基または塩基性基であることが好ましく、酸基または塩基性基であることが更に好ましい。 R7 in formula (1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group, and an alkyl group, It is more preferably an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group or an alkoxycarbonyl group, and even more preferably an electron-withdrawing group. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent. Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc. The group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基、および、アルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、後述する置換基Tで挙げた基、酸基および塩基性基が挙げられ、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基または塩基性基であることが好ましく、酸基または塩基性基であることが更に好ましい。 R7 in formula (1) is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group, and an alkyl group, It is more preferably an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group or an alkoxycarbonyl group, and even more preferably an electron-withdrawing group. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent. Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc. The group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
式(1)のX1は、CR8であることが好ましい。R8は、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、酸基または塩基性基であることが好ましく、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基またはアルコキシカルボニル基であることがより好ましく、シアノ基、カルバモイル基、または、アシル基であることが更に好ましい。
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基、および、アルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、後述する置換基Tで挙げた基、酸基および塩基性基が挙げられ、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基または塩基性基であることが好ましく、酸基または塩基性基であることが更に好ましい。
R8は、酸基または塩基性基を有する基であることが好ましく、酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることがより好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることが更に好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 It is preferable that X 1 in formula (1) is CR 8 . R 8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group; It is more preferably a group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and even more preferably a cyano group, a carbamoyl group, or an acyl group.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent. Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc. The group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
R 8 is preferably a group having an acid group or a basic group, and is an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent. is more preferred, an acyl group or carbamoyl group having an acid group or a basic group as a substituent is even more preferred, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferred.
上記のアルキル基、アリール基、ヘテロアリール基、アシル基、カルバモイル基、および、アルコキシカルボニル基は更に置換基を有していてもよい。更なる置換基としては、後述する置換基Tで挙げた基、酸基および塩基性基が挙げられ、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基または塩基性基であることが好ましく、酸基または塩基性基であることが更に好ましい。
R8は、酸基または塩基性基を有する基であることが好ましく、酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることがより好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることが更に好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 It is preferable that X 1 in formula (1) is CR 8 . R 8 is preferably an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group, or a basic group; It is more preferably a group, an acyl group, a nitro group, a cyano group, a carbamoyl group, or an alkoxycarbonyl group, and even more preferably a cyano group, a carbamoyl group, or an acyl group.
The above alkyl group, aryl group, heteroaryl group, acyl group, carbamoyl group, and alkoxycarbonyl group may further have a substituent. Further substituents include the groups listed below for substituent T, acid groups and basic groups, such as alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, etc. The group is preferably an alkoxycarbonyl group, an alkylthio group, an arylthio group, a morpholino group, an acid group or a basic group, and more preferably an acid group or a basic group.
R 8 is preferably a group having an acid group or a basic group, and is an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent. is more preferred, an acyl group or carbamoyl group having an acid group or a basic group as a substituent is even more preferred, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferred.
式(1)のX1がCR8である場合、R7とR8は結合して環を形成していてもよい。形成される環は、ピラゾリジンジオン環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
When X 1 in formula (1) is CR 8 , R 7 and R 8 may be combined to form a ring. The ring formed is preferably a pyrazolidinedione ring. The formed ring may have a substituent. Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
式(1)のR9は、水素原子、アルキル基、アリール基、ヘテロアリール基、酸基または塩基性基であることが好ましく、水素原子、アルキル基またはアリール基であることがより好ましく、水素原子であることが更に好ましい。
上記のアルキル基、アリール基およびヘテロアリール基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基などが挙げられる。 R9 in formula (1) is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an acid group, or a basic group, more preferably a hydrogen atom, an alkyl group, or an aryl group; More preferably, it is an atom.
The above alkyl group, aryl group and heteroaryl group may further have a substituent. Further substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and basic groups. Examples include groups.
上記のアルキル基、アリール基およびヘテロアリール基は更に置換基を有していてもよい。更なる置換基としては、アルキル基、アリール基、アルコキシ基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基などが挙げられる。 R9 in formula (1) is preferably a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an acid group, or a basic group, more preferably a hydrogen atom, an alkyl group, or an aryl group; More preferably, it is an atom.
The above alkyl group, aryl group and heteroaryl group may further have a substituent. Further substituents include alkyl groups, aryl groups, alkoxy groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, acid groups and basic groups. Examples include groups.
特定化合物は、式(1)のR1~R9の少なくとも1つが酸基または塩基性基を有する。特定化合物は、式(1)のR7およびR8の少なくとも1つが酸基または塩基性基を有することが好ましい。酸基および塩基性基は上述した基が挙げられる。
なかでも、R7が電子求引性基であり、X1がCR8であり、R8が酸基または塩基性基を含むことが特に好ましい。また、R8は酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることがより好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 In the specific compound, at least one of R 1 to R 9 in formula (1) has an acid group or a basic group. In the specific compound, at least one of R 7 and R 8 in formula (1) preferably has an acid group or a basic group. Examples of the acid group and basic group include the groups mentioned above.
Among these, it is particularly preferable that R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains an acid group or a basic group. Furthermore, R 8 is preferably an aryl group, heteroaryl group, acyl group, carbamoyl group, or alkoxycarbonyl group having an acid group or basic group as a substituent; It is more preferably an acyl group or a carbamoyl group, and particularly preferably a carbamoyl group having an acid group or a basic group as a substituent.
なかでも、R7が電子求引性基であり、X1がCR8であり、R8が酸基または塩基性基を含むことが特に好ましい。また、R8は酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることがより好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 In the specific compound, at least one of R 1 to R 9 in formula (1) has an acid group or a basic group. In the specific compound, at least one of R 7 and R 8 in formula (1) preferably has an acid group or a basic group. Examples of the acid group and basic group include the groups mentioned above.
Among these, it is particularly preferable that R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains an acid group or a basic group. Furthermore, R 8 is preferably an aryl group, heteroaryl group, acyl group, carbamoyl group, or alkoxycarbonyl group having an acid group or basic group as a substituent; It is more preferably an acyl group or a carbamoyl group, and particularly preferably a carbamoyl group having an acid group or a basic group as a substituent.
また、特定化合物は、欠陥の発生をより抑制できるという理由から、式(1)のR1~R9の少なくとも1つが塩基性基を有することが好ましく、R7およびR8の少なくとも1つが塩基性基を有することがより好ましい。なかでも、R7が電子求引性基であり、X1がCR8であり、R8が塩基性基を含むことが特に好ましい。また、R8は塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、塩基性基を置換基として有するアシル基またはカルバモイル基であることがより好ましく、塩基性基を置換基として有するカルバモイル基であることが特に好ましい。
Further, in the specific compound, it is preferable that at least one of R 1 to R 9 in formula (1) has a basic group, and at least one of R 7 and R 8 has a basic group, since the generation of defects can be further suppressed. It is more preferable to have a functional group. Among these, it is particularly preferable that R 7 is an electron-withdrawing group, X 1 is CR 8 , and R 8 contains a basic group. Further, R 8 is preferably an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having a basic group as a substituent, and an acyl group or a carbamoyl group having a basic group as a substituent. More preferably, it is a carbamoyl group having a basic group as a substituent.
(置換基T)
置換基Tとしては、次の基が挙げられる。ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、ヘテロアリール基(好ましくは炭素数1~30のヘテロアリール基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基(好ましくは炭素数1~30のヘテロアリールオキシ基)、アシル基(好ましくは炭素数2~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロアリールオキシカルボニル基(好ましくは炭素数2~30のヘテロアリールオキシカルボニル基)、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アミノカルボニルアミノ基(好ましくは炭素数2~30のアミノカルボニルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、スルファモイルアミノ基(好ましくは炭素数0~30のスルファモイルアミノ基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30のヘテロアリールチオ基)、アルキルスルホニル基(好ましくは炭素数1~30のアルキルスルホニル基)、アルキルスルホニルアミノ基(好ましくは炭素数1~30のアルキルスルホニルアミノ基)、アリールスルホニル基(好ましくは炭素数6~30のアリールスルホニル基)、アリールスルホニルアミノ基(好ましくは炭素数6~30のアリールスルホニルアミノ基)、ヘテロアリールスルホニル基(好ましくは炭素数1~30のヘテロアリールスルホニル基)、ヘテロアリールスルホニルアミノ基(好ましくは炭素数1~30のヘテロアリールスルホニルアミノ基)、アルキルスルフィニル基(好ましくは炭素数1~30のアルキルスルフィニル基)、アリールスルフィニル基(好ましくは炭素数6~30のアリールスルフィニル基)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30のヘテロアリールスルフィニル基)、ウレイド基(好ましくは炭素数1~30のウレイド基)、ヒドロキシ基、ニトロ基、イミド基、メルカプト基、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、アリールアゾ基、ヘテロアリールアゾ基、シリル基、ヒドラジノ基、イミノ基。これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。置換基としては、上述した置換基Tで説明した基が挙げられる。 (Substituent T)
Examples of the substituent T include the following groups. Halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (preferably an alkyl group having 1 to 30 carbon atoms), alkenyl group (preferably an alkenyl group having 2 to 30 carbon atoms), alkynyl group (preferably an alkynyl group having 2 to 30 carbon atoms), an aryl group (preferably an aryl group having 6 to 30 carbon atoms), a heteroaryl group (preferably a heteroaryl group having 1 to 30 carbon atoms), an alkoxy group (preferably (alkoxy group having 1 to 30 carbon atoms), aryloxy group (preferably aryloxy group having 6 to 30 carbon atoms), heteroaryloxy group (preferably heteroaryloxy group having 1 to 30 carbon atoms), acyl group (preferably is an acyl group having 2 to 30 carbon atoms), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), heteroaryloxy Carbonyl group (preferably heteroaryloxycarbonyl group having 2 to 30 carbon atoms), acyloxy group (preferably acyloxy group having 2 to 30 carbon atoms), acylamino group (preferably acylamino group having 2 to 30 carbon atoms), aminocarbonyl An amino group (preferably an aminocarbonylamino group having 2 to 30 carbon atoms), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms), an aryloxycarbonylamino group (preferably an aminocarbonylamino group having 7 to 30 carbon atoms) aryloxycarbonylamino group), sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms), sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group having 1 to 30 carbon atoms), alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms), arylthio group (preferably an arylthio group having 6 to 30 carbon atoms), heteroarylthio group (preferably an arylthio group having 1 to 30 carbon atoms) a heteroarylthio group), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms), an alkylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), an arylsulfonyl group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), arylsulfonyl group having 6 to 30 carbon atoms), arylsulfonylamino group (preferably an arylsulfonylamino group having 6 to 30 carbon atoms), heteroarylsulfonyl group (preferably a heteroarylsulfonyl group having 1 to 30 carbon atoms), heteroaryl A sulfonylamino group (preferably a heteroarylsulfonylamino group having 1 to 30 carbon atoms), an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms), an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 30 carbon atoms) group), heteroarylsulfinyl group (preferably a heteroarylsulfinyl group having 1 to 30 carbon atoms), ureido group (preferably a ureido group having 1 to 30 carbon atoms), hydroxy group, nitro group, imido group, mercapto group, cyano group group, alkylsulfino group, arylsulfino group, arylazo group, heteroarylazo group, silyl group, hydrazino group, imino group. These groups may further have a substituent when the group is a substitutable group. Examples of the substituent include the groups described above for the substituent T.
置換基Tとしては、次の基が挙げられる。ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アルキル基(好ましくは炭素数1~30のアルキル基)、アルケニル基(好ましくは炭素数2~30のアルケニル基)、アルキニル基(好ましくは炭素数2~30のアルキニル基)、アリール基(好ましくは炭素数6~30のアリール基)、ヘテロアリール基(好ましくは炭素数1~30のヘテロアリール基)、アルコキシ基(好ましくは炭素数1~30のアルコキシ基)、アリールオキシ基(好ましくは炭素数6~30のアリールオキシ基)、ヘテロアリールオキシ基(好ましくは炭素数1~30のヘテロアリールオキシ基)、アシル基(好ましくは炭素数2~30のアシル基)、アルコキシカルボニル基(好ましくは炭素数2~30のアルコキシカルボニル基)、アリールオキシカルボニル基(好ましくは炭素数7~30のアリールオキシカルボニル基)、ヘテロアリールオキシカルボニル基(好ましくは炭素数2~30のヘテロアリールオキシカルボニル基)、アシルオキシ基(好ましくは炭素数2~30のアシルオキシ基)、アシルアミノ基(好ましくは炭素数2~30のアシルアミノ基)、アミノカルボニルアミノ基(好ましくは炭素数2~30のアミノカルボニルアミノ基)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30のアルコキシカルボニルアミノ基)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30のアリールオキシカルボニルアミノ基)、スルファモイル基(好ましくは炭素数0~30のスルファモイル基)、スルファモイルアミノ基(好ましくは炭素数0~30のスルファモイルアミノ基)、カルバモイル基(好ましくは炭素数1~30のカルバモイル基)、アルキルチオ基(好ましくは炭素数1~30のアルキルチオ基)、アリールチオ基(好ましくは炭素数6~30のアリールチオ基)、ヘテロアリールチオ基(好ましくは炭素数1~30のヘテロアリールチオ基)、アルキルスルホニル基(好ましくは炭素数1~30のアルキルスルホニル基)、アルキルスルホニルアミノ基(好ましくは炭素数1~30のアルキルスルホニルアミノ基)、アリールスルホニル基(好ましくは炭素数6~30のアリールスルホニル基)、アリールスルホニルアミノ基(好ましくは炭素数6~30のアリールスルホニルアミノ基)、ヘテロアリールスルホニル基(好ましくは炭素数1~30のヘテロアリールスルホニル基)、ヘテロアリールスルホニルアミノ基(好ましくは炭素数1~30のヘテロアリールスルホニルアミノ基)、アルキルスルフィニル基(好ましくは炭素数1~30のアルキルスルフィニル基)、アリールスルフィニル基(好ましくは炭素数6~30のアリールスルフィニル基)、ヘテロアリールスルフィニル基(好ましくは炭素数1~30のヘテロアリールスルフィニル基)、ウレイド基(好ましくは炭素数1~30のウレイド基)、ヒドロキシ基、ニトロ基、イミド基、メルカプト基、シアノ基、アルキルスルフィノ基、アリールスルフィノ基、アリールアゾ基、ヘテロアリールアゾ基、シリル基、ヒドラジノ基、イミノ基。これらの基は、さらに置換可能な基である場合、さらに置換基を有してもよい。置換基としては、上述した置換基Tで説明した基が挙げられる。 (Substituent T)
Examples of the substituent T include the following groups. Halogen atom (e.g. fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (preferably an alkyl group having 1 to 30 carbon atoms), alkenyl group (preferably an alkenyl group having 2 to 30 carbon atoms), alkynyl group (preferably an alkynyl group having 2 to 30 carbon atoms), an aryl group (preferably an aryl group having 6 to 30 carbon atoms), a heteroaryl group (preferably a heteroaryl group having 1 to 30 carbon atoms), an alkoxy group (preferably (alkoxy group having 1 to 30 carbon atoms), aryloxy group (preferably aryloxy group having 6 to 30 carbon atoms), heteroaryloxy group (preferably heteroaryloxy group having 1 to 30 carbon atoms), acyl group (preferably is an acyl group having 2 to 30 carbon atoms), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), heteroaryloxy Carbonyl group (preferably heteroaryloxycarbonyl group having 2 to 30 carbon atoms), acyloxy group (preferably acyloxy group having 2 to 30 carbon atoms), acylamino group (preferably acylamino group having 2 to 30 carbon atoms), aminocarbonyl An amino group (preferably an aminocarbonylamino group having 2 to 30 carbon atoms), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms), an aryloxycarbonylamino group (preferably an aminocarbonylamino group having 7 to 30 carbon atoms) aryloxycarbonylamino group), sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms), sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group having 1 to 30 carbon atoms), alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms), arylthio group (preferably an arylthio group having 6 to 30 carbon atoms), heteroarylthio group (preferably an arylthio group having 1 to 30 carbon atoms) a heteroarylthio group), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms), an alkylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), an arylsulfonyl group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), arylsulfonyl group having 6 to 30 carbon atoms), arylsulfonylamino group (preferably an arylsulfonylamino group having 6 to 30 carbon atoms), heteroarylsulfonyl group (preferably a heteroarylsulfonyl group having 1 to 30 carbon atoms), heteroaryl A sulfonylamino group (preferably a heteroarylsulfonylamino group having 1 to 30 carbon atoms), an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms), an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 30 carbon atoms) group), heteroarylsulfinyl group (preferably a heteroarylsulfinyl group having 1 to 30 carbon atoms), ureido group (preferably a ureido group having 1 to 30 carbon atoms), hydroxy group, nitro group, imido group, mercapto group, cyano group group, alkylsulfino group, arylsulfino group, arylazo group, heteroarylazo group, silyl group, hydrazino group, imino group. These groups may further have a substituent when the group is a substitutable group. Examples of the substituent include the groups described above for the substituent T.
特定化合物は、式(2)または式(3)で表される化合物であることが好ましく、式(2)で表される化合物であることがより好ましい。なお、式(2)におけるR17およびR18をつなぐ波線の結合は、式(2)のようにR17が下側(R16側)で、R18が上側(R19側)であってもよく、あるいは、R18が下側(R16側)で、R17が上側(R19側)であってもよいことを意味する。
The specific compound is preferably a compound represented by formula (2) or formula (3), and more preferably a compound represented by formula (2). Note that the bond of the wavy line connecting R 17 and R 18 in formula (2) is that R 17 is on the lower side (R 16 side) and R 18 is on the upper side (R 19 side) as in formula (2). Alternatively, R 18 may be on the lower side (R 16 side) and R 17 may be on the upper side (R 19 side).
式(2)中、R11~R19はそれぞれ独立して、水素原子または置換基を表し、
R11~R19の少なくとも1つは酸基または塩基性基を有し、
R11~R16の2以上が結合して環を形成していてもよい;
式(3)中、R21~R29はそれぞれ独立して、水素原子または置換基を表し、
R21~R29の少なくとも1つは酸基または塩基性基を有し、
R21~R28の2以上が結合して環を形成していてもよい; In formula (2), R 11 to R 19 each independently represent a hydrogen atom or a substituent,
At least one of R 11 to R 19 has an acid group or a basic group,
Two or more of R 11 to R 16 may be combined to form a ring;
In formula (3), R 21 to R 29 each independently represent a hydrogen atom or a substituent,
At least one of R 21 to R 29 has an acid group or a basic group,
Two or more of R 21 to R 28 may be combined to form a ring;
R11~R19の少なくとも1つは酸基または塩基性基を有し、
R11~R16の2以上が結合して環を形成していてもよい;
式(3)中、R21~R29はそれぞれ独立して、水素原子または置換基を表し、
R21~R29の少なくとも1つは酸基または塩基性基を有し、
R21~R28の2以上が結合して環を形成していてもよい; In formula (2), R 11 to R 19 each independently represent a hydrogen atom or a substituent,
At least one of R 11 to R 19 has an acid group or a basic group,
Two or more of R 11 to R 16 may be combined to form a ring;
In formula (3), R 21 to R 29 each independently represent a hydrogen atom or a substituent,
At least one of R 21 to R 29 has an acid group or a basic group,
Two or more of R 21 to R 28 may be combined to form a ring;
式(2)のR11~R16および式(3)のR21~R26は、式(1)のR1~R6と同義であり、好ましい範囲も同様である。
式(2)のR19および式(3)のR29は、式(1)のR9と同義であり、好ましい範囲も同様である。 R 11 to R 16 in formula (2) and R 21 to R 26 in formula (3) have the same meanings as R 1 to R 6 in formula (1), and their preferred ranges are also the same.
R 19 in formula (2) and R 29 in formula (3) have the same meaning as R 9 in formula (1), and the preferred ranges are also the same.
式(2)のR19および式(3)のR29は、式(1)のR9と同義であり、好ましい範囲も同様である。 R 11 to R 16 in formula (2) and R 21 to R 26 in formula (3) have the same meanings as R 1 to R 6 in formula (1), and their preferred ranges are also the same.
R 19 in formula (2) and R 29 in formula (3) have the same meaning as R 9 in formula (1), and the preferred ranges are also the same.
式(2)のR17およびR18は、それぞれ独立して、アルキル基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、酸基または塩基性基であることが好ましい。
R 17 and R 18 in formula (2) are each independently an alkyl group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano group, a carbamoyl group, an alkoxycarbonyl group, an acid group or a basic group. It is preferable that there be.
また、R17およびR18の少なくとも1つは電子求引性基であることが好ましい。電子求引性基としては、シアノ基、カルバモイル基、および、アシル基が挙げられる。
R17およびR18のいずれか一方は電子求引性基で、他方は、酸基または塩基性基を有する基であることが好ましく、塩基性基を有する基であることがより好ましい。酸基または塩基性基を有する基は、酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることがより好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 Moreover, it is preferable that at least one of R 17 and R 18 is an electron-withdrawing group. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
One of R 17 and R 18 is preferably an electron-withdrawing group, and the other is preferably a group having an acid group or a basic group, more preferably a group having a basic group. The group having an acid group or a basic group is preferably an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent; An acyl group or a carbamoyl group having a basic group as a substituent is more preferable, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferable.
R17およびR18のいずれか一方は電子求引性基で、他方は、酸基または塩基性基を有する基であることが好ましく、塩基性基を有する基であることがより好ましい。酸基または塩基性基を有する基は、酸基または塩基性基を置換基として有するアリール基、ヘテロアリール基、アシル基、カルバモイル基、または、アルコキシカルボニル基であることが好ましく、酸基または塩基性基を置換基として有するアシル基またはカルバモイル基であることがより好ましく、酸基または塩基性基を置換基として有するカルバモイル基であることが特に好ましい。 Moreover, it is preferable that at least one of R 17 and R 18 is an electron-withdrawing group. Examples of the electron-withdrawing group include a cyano group, a carbamoyl group, and an acyl group.
One of R 17 and R 18 is preferably an electron-withdrawing group, and the other is preferably a group having an acid group or a basic group, more preferably a group having a basic group. The group having an acid group or a basic group is preferably an aryl group, a heteroaryl group, an acyl group, a carbamoyl group, or an alkoxycarbonyl group having an acid group or a basic group as a substituent; An acyl group or a carbamoyl group having a basic group as a substituent is more preferable, and a carbamoyl group having an acid group or a basic group as a substituent is particularly preferable.
式(3)のR27およびR28の好ましい態様は、式(1)のR1およびR2の好ましい態様と同様である。
The preferred embodiments of R 27 and R 28 in formula (3) are the same as the preferred embodiments of R 1 and R 2 in formula (1).
式(3)のR27とR28は結合して環を形成していてもよい。形成される環は、5員環または6員環であることが好ましい。形成される環は、置換基を有していてもよい。置換基としては、ハロゲン原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、ヘテロアリール基、アシル基、ニトロ基、シアノ基、カルバモイル基、アルコキシカルボニル基、アルキルチオ基、アリールチオ基、モルフォリノ基、酸基および塩基性基等が挙げられる。
R 27 and R 28 in formula (3) may be combined to form a ring. The ring formed is preferably a 5-membered ring or a 6-membered ring. The formed ring may have a substituent. Substituents include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, heteroaryl groups, acyl groups, nitro groups, cyano groups, carbamoyl groups, alkoxycarbonyl groups, alkylthio groups, arylthio groups, morpholino groups, and acids. and basic groups.
式(3)において、R21、R22、R27およびR28はいずれも同じ基であることが好ましい。
In formula (3), it is preferable that R 21 , R 22 , R 27 and R 28 are all the same group.
特定化合物の具体例としては、後述する実施例において用いられる化合物(YY-1)~(YY-13)が挙げられる。
Specific examples of the specific compound include compounds (YY-1) to (YY-13) used in Examples described below.
着色組成物の全固形分中における特定化合物の含有量は、0.1~50質量%であることが好ましい。下限は、1質量%以上であることが好ましく、1質量%以上であることがより好ましい。上限は、30質量%以下であることが好ましく、20質量%以下であることがより好ましい。
特定化合物の含有量は、イソインドリン顔料100質量部に対して1~100質量部であることが好ましい。下限は、3質量部以上であることが好ましく、5質量部以上であることがより好ましい。上限は、70質量部以下であることが好ましく、50質量部以下であることがより好ましい。
特定化合物は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 The content of the specific compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass. The lower limit is preferably 1% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
The content of the specific compound is preferably 1 to 100 parts by weight based on 100 parts by weight of the isoindoline pigment. The lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more. The upper limit is preferably 70 parts by mass or less, more preferably 50 parts by mass or less.
Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
特定化合物の含有量は、イソインドリン顔料100質量部に対して1~100質量部であることが好ましい。下限は、3質量部以上であることが好ましく、5質量部以上であることがより好ましい。上限は、70質量部以下であることが好ましく、50質量部以下であることがより好ましい。
特定化合物は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 The content of the specific compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass. The lower limit is preferably 1% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
The content of the specific compound is preferably 1 to 100 parts by weight based on 100 parts by weight of the isoindoline pigment. The lower limit is preferably 3 parts by mass or more, more preferably 5 parts by mass or more. The upper limit is preferably 70 parts by mass or less, more preferably 50 parts by mass or less.
Only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
<<他の顔料誘導体>>
本発明の着色組成物は、上述した特定化合物以外の顔料誘導体(以下、他の顔料誘導体ともいう)を含有することができる。顔料誘導体は例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。 <<Other pigment derivatives>>
The colored composition of the present invention can contain pigment derivatives (hereinafter also referred to as other pigment derivatives) other than the above-mentioned specific compounds. Pigment derivatives are used, for example, as pigment dispersion aids. A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition.
本発明の着色組成物は、上述した特定化合物以外の顔料誘導体(以下、他の顔料誘導体ともいう)を含有することができる。顔料誘導体は例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。 <<Other pigment derivatives>>
The colored composition of the present invention can contain pigment derivatives (hereinafter also referred to as other pigment derivatives) other than the above-mentioned specific compounds. Pigment derivatives are used, for example, as pigment dispersion aids. A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition.
他の顔料誘導体としては、色素構造およびトリアジン構造から選ばれる少なくとも1種の構造と、酸基または塩基性基とを有する化合物が挙げられる。
Examples of other pigment derivatives include compounds having at least one structure selected from a pigment structure and a triazine structure, and an acid group or a basic group.
上記色素構造としては、キノリン色素構造、ベンゾイミダゾロン色素構造、ベンゾイソインドール色素構造、ベンゾチアゾール色素構造、イミニウム色素構造、スクアリリウム色素構造、クロコニウム色素構造、オキソノール色素構造、ピロロピロール色素構造、ジケトピロロピロール色素構造、アゾ色素構造、アゾメチン色素構造、フタロシアニン色素構造、ナフタロシアニン色素構造、アントラキノン色素構造、キナクリドン色素構造、ジオキサジン色素構造、ペリノン色素構造、ペリレン色素構造、チアジンインジゴ色素構造、チオインジゴ色素構造、イソインドリン色素構造、イソインドリノン色素構造、キノフタロン色素構造、ジチオール色素構造、トリアリールメタン色素構造、ピロメテン色素構造等が挙げられる。
The above dye structures include quinoline dye structure, benzimidazolone dye structure, benzisoindole dye structure, benzothiazole dye structure, iminium dye structure, squarylium dye structure, croconium dye structure, oxonol dye structure, pyrrolopyrrole dye structure, diketo Pyrrolopyrrole dye structure, azo dye structure, azomethine dye structure, phthalocyanine dye structure, naphthalocyanine dye structure, anthraquinone dye structure, quinacridone dye structure, dioxazine dye structure, perinone dye structure, perylene dye structure, thiazine indigo dye structure, thioindigo dye structure, isoindoline dye structure, isoindolinone dye structure, quinophthalone dye structure, dithiol dye structure, triarylmethane dye structure, pyrromethene dye structure, etc.
他の顔料誘導体が有する酸基および塩基性基としては、上述した特定化合物が有することのできる酸基および塩基性基として挙げた基が挙げられる。
Examples of the acid groups and basic groups that other pigment derivatives have include the groups listed above as the acid groups and basic groups that the specific compounds mentioned above can have.
他の顔料誘導体は、可視透明性に優れた顔料誘導体(以下、透明顔料誘導体ともいう)を用いることもできる。透明顔料誘導体の400~700nmの波長領域におけるモル吸光係数の最大値(εmax)は3000L・mol-1・cm-1以下であることが好ましく、1000L・mol-1・cm-1以下であることがより好ましく、100L・mol-1・cm-1以下であることがさらに好ましい。εmaxの下限は、例えば1L・mol-1・cm-1以上であり、10L・mol-1・cm-1以上でもよい。
As other pigment derivatives, pigment derivatives having excellent visible transparency (hereinafter also referred to as transparent pigment derivatives) can also be used. The maximum molar extinction coefficient (εmax) of the transparent pigment derivative in the wavelength range of 400 to 700 nm is preferably 3000 L·mol −1 ·cm −1 or less, and preferably 1000 L·mol −1 ·cm −1 or less. is more preferable, and even more preferably 100 L·mol −1 ·cm −1 or less. The lower limit of εmax is, for example, 1 L·mol −1 ·cm −1 or more, and may be 10 L·mol −1 ·cm −1 or more.
他の顔料誘導体の具体例としては、国際公開第2022/085485号の段落0124に記載の化合物、特開2018-168244号公報に記載のベンゾイミダゾロン化合物、または、それらの塩、特許第6996282号の一般式(1)に記載のイソインドリン骨格を有する化合物などが挙げられる。
Specific examples of other pigment derivatives include the compound described in paragraph 0124 of International Publication No. 2022/085485, the benzimidazolone compound described in JP 2018-168244, or a salt thereof, and Patent No. 6996282. Examples include compounds having an isoindoline skeleton represented by the general formula (1).
他の顔料誘導体の含有量は、上述した特定化合物の100質量部に対して100質量部以下であることが好ましく、80質量部以下であることがより好ましい。下限は1質量部以上とすることができ、3質量部以上とすることもできる。
The content of other pigment derivatives is preferably 100 parts by mass or less, more preferably 80 parts by mass or less, based on 100 parts by mass of the above-mentioned specific compound. The lower limit can be 1 part by mass or more, and can also be 3 parts by mass or more.
<<樹脂>>
本発明の着色組成物は樹脂を含む。樹脂は、例えば、顔料などを着色組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料などを着色組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。 <<Resin>>
The colored composition of the present invention contains a resin. The resin is blended, for example, for dispersing pigments in a coloring composition or for use as a binder. Note that a resin used mainly for dispersing pigments and the like in a coloring composition is also referred to as a dispersant. However, this use of the resin is just one example, and the resin can also be used for purposes other than this use.
本発明の着色組成物は樹脂を含む。樹脂は、例えば、顔料などを着色組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料などを着色組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。 <<Resin>>
The colored composition of the present invention contains a resin. The resin is blended, for example, for dispersing pigments in a coloring composition or for use as a binder. Note that a resin used mainly for dispersing pigments and the like in a coloring composition is also referred to as a dispersant. However, this use of the resin is just one example, and the resin can also be used for purposes other than this use.
樹脂の重量平均分子量(Mw)は、3000~2000000が好ましい。上限は、1000000以下が好ましく、500000以下がより好ましい。下限は、4000以上が好ましく、5000以上がより好ましい。
The weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less. The lower limit is preferably 4000 or more, more preferably 5000 or more.
樹脂としては、例えば、(メタ)アクリル樹脂、エポキシ樹脂、(メタ)アクリルアミド樹脂、エン・チオール樹脂、ポリカーボネート樹脂、ポリエーテル樹脂、ポリアリレート樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリフェニレン樹脂、ポリアリーレンエーテルホスフィンオキシド樹脂、ポリイミド樹脂、ポリアミドイミド樹脂、ポリオレフィン樹脂、環状オレフィン樹脂、ポリエステル樹脂、スチレン樹脂、シロキサン樹脂などが挙げられる。また、樹脂としては、国際公開第2022/065215号の段落番号0091~0099に記載の樹脂、特開2016-222891号公報に記載されたブロックポリイソシアネート樹脂、特開2020-122052号公報に記載された樹脂、特開2020-111656号公報に記載された樹脂、特開2020-139021号公報に記載された樹脂、特開2017-138503号公報に記載の主鎖に環構造を有する構成単位と側鎖にビフェニル基を有する構成単位とを含む樹脂、特開2020-186373号公報の段落0199~0233に記載の樹脂、特開2020-186325号公報に記載のアルカリ可溶性樹脂、韓国公開特許第10-2020-0078339号公報に記載の式1で表される樹脂、国際公開第2022/030445号に記載のエポキシ基と酸基を含む共重合体を用いることもできる。
Examples of the resin include (meth)acrylic resin, epoxy resin, (meth)acrylamide resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and siloxane resin. Examples of the resin include the resin described in paragraphs 0091 to 0099 of International Publication No. 2022/065215, the blocked polyisocyanate resin described in JP 2016-222891 A, the resin described in JP 2020-122052 A, the resin described in JP 2020-111656 A, the resin described in JP 2020-139021 A, and the resin having a ring structure in the main chain described in JP 2017-138503 A. Resins containing a structural unit having a structure and a structural unit having a biphenyl group in a side chain, resins described in paragraphs 0199 to 0233 of JP 2020-186373 A, alkali-soluble resins described in JP 2020-186325 A, resins represented by formula 1 described in Korean Patent Publication No. 10-2020-0078339 A, and copolymers containing epoxy groups and acid groups described in WO 2022/030445 A can also be used.
樹脂としては、酸基を有する樹脂を用いることが好ましい。酸基としては、例えば、カルボキシ基、リン酸基、スルホ基、フェノール性ヒドロキシ基などが挙げられる。
As the resin, it is preferable to use a resin having acid groups. Examples of the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group.
酸基を有する樹脂の酸価は、30~500mgKOH/gが好ましい。下限は、40mgKOH/g以上がより好ましく、50mgKOH/g以上が特に好ましい。上限は、400mgKOH/g以下がより好ましく、300mgKOH/g以下が更に好ましく、200mgKOH/g以下が特に好ましい。酸基を有する樹脂の重量平均分子量(Mw)は、5000~100000が好ましく、5000~50000がより好ましい。また、酸基を有する樹脂の数平均分子量(Mn)は、1000~20000が好ましい。
The acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g. The lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more. The upper limit is more preferably 400 mgKOH/g or less, even more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less. The weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, more preferably 5,000 to 50,000. Further, the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
酸基を有する樹脂は、酸基を側鎖に有する繰り返し単位を含むことが好ましく、酸基を側鎖に有する繰り返し単位を樹脂の全繰り返し単位中5~70モル%含むことがより好ましい。酸基を側鎖に有する繰り返し単位の含有量の上限は、50モル%以下であることが好ましく、30モル%以下であることがより好ましい。酸基を側鎖に有する繰り返し単位の含有量の下限は、10モル%以上であることが好ましく、20モル%以上であることがより好ましい。
The resin having an acid group preferably contains a repeating unit having an acid group in its side chain, and more preferably contains 5 to 70 mol% of repeating units having an acid group in its side chain based on the total repeating units of the resin. The upper limit of the content of repeating units having acid groups in their side chains is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of repeating units having acid groups in their side chains is preferably 10 mol% or more, more preferably 20 mol% or more.
酸基を有する樹脂については、特開2012-208494号公報の段落番号0558~0571(対応する米国特許出願公開第2012/0235099号明細書の段落番号0685~0700)の記載、特開2012-198408号公報の段落番号0076~0099の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、酸基を有する樹脂は市販品を用いることもできる。また、樹脂への酸基の導入方法としては、特に制限はないが、例えば、特許第6349629号公報に記載の方法が挙げられる。更に、樹脂への酸基の導入方法としては、エポキシ基の開環反応で生じたヒドロキシ基に酸無水物を反応させて酸基を導入する方法も挙げられる。
Regarding resins having acid groups, the descriptions in paragraph numbers 0558 to 0571 of JP 2012-208494 (corresponding paragraph numbers 0685 to 0700 of US Patent Application Publication No. 2012/0235099), JP 2012-198408 The descriptions in paragraph numbers 0076 to 0099 of the publication can be referred to, and the contents thereof are incorporated into the present specification. Furthermore, commercially available resins having acid groups can also be used. Furthermore, there are no particular limitations on the method for introducing acid groups into the resin, but examples include the method described in Japanese Patent No. 6,349,629. Furthermore, as a method for introducing acid groups into the resin, there is also a method of reacting an acid anhydride with a hydroxy group generated by a ring-opening reaction of an epoxy group to introduce an acid group.
本発明の着色組成物は、塩基性基を有する樹脂を含むことも好ましい。塩基性基を有する樹脂は、塩基性基を側鎖に有する繰り返し単位を含む樹脂であることが好ましく、塩基性基を側鎖に有する繰り返し単位と塩基性基を含まない繰り返し単位とを有する共重合体であることがより好ましく、塩基性基を側鎖に有する繰り返し単位と、塩基性基を含まない繰り返し単位とを有するブロック共重合体であることが更に好ましい。塩基性基を有する樹脂は分散剤として用いることもできる。塩基性基を有する樹脂のアミン価は、5~300mgKOH/gが好ましい。下限は、10mgKOH/g以上が好ましく、20mgKOH/g以上がより好ましい。上限は、200mgKOH/g以下が好ましく、100mgKOH/g以下がより好ましい。
It is also preferable that the colored composition of the present invention contains a resin having a basic group. The resin having a basic group is preferably a resin containing a repeating unit having a basic group in its side chain, and a resin having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group. A polymer is more preferable, and a block copolymer having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group is even more preferable. A resin having a basic group can also be used as a dispersant. The amine value of the resin having a basic group is preferably 5 to 300 mgKOH/g. The lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more. The upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
塩基性基を有する樹脂の市販品としては、DISPERBYK-161、162、163、164、166、167、168、174、182、183、184、185、2000、2001、2050、2150、2163、2164、BYK-LPN6919(以上、ビックケミー社製)、ソルスパース11200、13240、13650、13940、24000、26000、28000、32000、32500、32550、32600、33000、34750、35100、35200、37500、38500、39000、53095、56000、7100(以上、日本ルーブリゾール社製)、Efka PX 4300、4330、4046、4060、4080(以上、BASF社製)等が挙げられる。また、塩基性基を有する樹脂は、特開2014-219665号公報の段落番号0063~0112に記載されたブロック共重合体(B)、特開2018-156021号公報の段落番号0046~0076に記載されたブロック共重合体A1、特開2019-184763号公報の段落番号0150~0153に記載された塩基性基を有するビニル樹脂を用いることもでき、これらの内容は本明細書に組み込まれる。
Commercially available resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK Chemie), Solsperse 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 385 00, 39000, 53095, 56000, 7100 (all manufactured by Japan Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like. In addition, the resin having a basic group is the block copolymer (B) described in paragraph numbers 0063 to 0112 of JP2014-219665A, and the block copolymer (B) described in paragraphs 0046 to 0076 of JP2018-156021A. It is also possible to use block copolymer A1, a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP-A No. 2019-184763, the contents of which are incorporated herein.
本発明の着色組成物は、酸基を有する樹脂と塩基性基を有する樹脂とをそれぞれ含むことも好ましい。この態様によれば、着色組成物の保存安定性をより向上できる。酸基を有する樹脂と塩基性基を有する樹脂とを併用する場合、塩基性基を有する樹脂の含有量は、酸基を有する樹脂の100質量部に対して20~500質量部であることが好ましく、30~300質量部であることがより好ましく、50~200質量部であることが更に好ましい。
It is also preferable that the colored composition of the present invention contains a resin having an acid group and a resin having a basic group. According to this aspect, the storage stability of the colored composition can be further improved. When a resin having an acid group and a resin having a basic group are used together, the content of the resin having a basic group is preferably 20 to 500 parts by mass per 100 parts by mass of the resin having an acid group. The amount is preferably 30 to 300 parts by weight, more preferably 50 to 200 parts by weight.
樹脂としては、芳香族カルボキシ基を有する樹脂(以下、樹脂Acともいう)を用いることも好ましい。樹脂Acにおいて、芳香族カルボキシ基は繰り返し単位の主鎖に含まれていてもよく、繰り返し単位の側鎖に含まれていてもよい。芳香族カルボキシ基は繰り返し単位の主鎖に含まれていることが好ましい。なお、本明細書において、芳香族カルボキシ基とは、芳香族環にカルボキシ基が1個以上結合した構造の基のことである。芳香族カルボキシ基において、芳香族環に結合したカルボキシ基の数は、1~4個であることが好ましく、1~2個であることがより好ましい。
As the resin, it is also preferable to use a resin having an aromatic carboxy group (hereinafter also referred to as resin Ac). In the resin Ac, the aromatic carboxy group may be included in the main chain of the repeating unit, or may be included in the side chain of the repeating unit. The aromatic carboxy group is preferably contained in the main chain of the repeating unit. In addition, in this specification, an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring. In the aromatic carboxy group, the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2.
樹脂Acは、式(Ac-1)で表される繰り返し単位および式(Ac-2)で表される繰り返し単位から選ばれる少なくとも1種の繰り返し単位を含む樹脂であることが好ましい。
式(Ac-1)中、Ar1は芳香族カルボキシ基を含む基を表し、L1は、-COO-または-CONH-を表し、L2は、2価の連結基を表す。
式(Ac-2)中、Ar10は芳香族カルボキシ基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。 The resin Ac is preferably a resin containing at least one type of repeating unit selected from a repeating unit represented by formula (Ac-1) and a repeating unit represented by formula (Ac-2).
In formula (Ac-1), Ar 1 represents a group containing an aromatic carboxy group, L 1 represents -COO- or -CONH-, and L 2 represents a divalent linking group.
In formula (Ac-2), Ar 10 represents a group containing an aromatic carboxy group, L 11 represents -COO- or -CONH-, L 12 represents a trivalent linking group, and P 10 represents a polymer Represents a chain.
式(Ac-2)中、Ar10は芳香族カルボキシ基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。 The resin Ac is preferably a resin containing at least one type of repeating unit selected from a repeating unit represented by formula (Ac-1) and a repeating unit represented by formula (Ac-2).
In formula (Ac-2), Ar 10 represents a group containing an aromatic carboxy group, L 11 represents -COO- or -CONH-, L 12 represents a trivalent linking group, and P 10 represents a polymer Represents a chain.
式(Ac-1)においてAr1が表す芳香族カルボキシ基を含む基としては、芳香族トリカルボン酸無水物から由来する構造、芳香族テトラカルボン酸無水物から由来する構造などが挙げられる。芳香族トリカルボン酸無水物および芳香族テトラカルボン酸無水物としては、下記構造の化合物が挙げられる。
Examples of the group containing an aromatic carboxy group represented by Ar 1 in formula (Ac-1) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like. Examples of the aromatic tricarboxylic anhydride and aromatic tetracarboxylic anhydride include compounds having the following structures.
上記式中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、下記式(Q-1)で表される基または下記式(Q-2)で表される基を表す。
In the above formula, Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1). or a group represented by the following formula (Q-2).
Ar1が表す芳香族カルボキシ基を含む基は、架橋性基を有していてもよい。架橋性基は、エチレン性不飽和結合含有基および環状エーテル基であることが好ましく、エチレン性不飽和結合含有基であることがより好ましい。Ar1が表す芳香族カルボキシ基を含む基の具体例としては、式(Ar-11)で表される基、式(Ar-12)で表される基、式(Ar-13)で表される基などが挙げられる。
The aromatic carboxy group-containing group represented by Ar 1 may have a crosslinkable group. The crosslinkable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group. Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). Examples include groups such as
式(Ar-11)中、n1は1~4の整数を表し、1または2であることが好ましく、2であることがより好ましい。
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
式(Ar-11)~(Ar-13)中、*1はL1との結合位置を表す。 In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
In formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
In formula (Ar-13), Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- Represents a group represented by 1) or a group represented by the above formula (Q-2).
In formulas (Ar-11) to (Ar-13), *1 represents the bonding position with L 1 .
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
式(Ar-11)~(Ar-13)中、*1はL1との結合位置を表す。 In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
In formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
In formula (Ar-13), Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- Represents a group represented by 1) or a group represented by the above formula (Q-2).
In formulas (Ar-11) to (Ar-13), *1 represents the bonding position with L 1 .
式(Ac-1)においてL1は、-COO-または-CONH-を表し、-COO-を表すことが好ましい。
In formula (Ac-1), L 1 represents -COO- or -CONH-, and preferably represents -COO-.
式(Ac-1)においてL2が表す2価の連結基としては、アルキレン基、アリーレン基、-O-、-CO-、-COO-、-OCO-、-NH-、-S-およびこれらの2種以上を組み合わせた基が挙げられる。アルキレン基の炭素数は、1~30が好ましく、1~20がより好ましく、1~15が更に好ましい。アルキレン基は、直鎖、分岐、環状のいずれでもよい。アリーレン基の炭素数は、6~30が好ましく、6~20がより好ましく、6~10が更に好ましい。アルキレン基およびアリーレン基は置換基を有していてもよい。置換基としては、ヒドロキシ基などが挙げられる。L2が表す2価の連結基は、-L2a-O-で表される基であることが好ましい。L2aは、アルキレン基;アリーレン基;アルキレン基とアリーレン基とを組み合わせた基;アルキレン基およびアリーレン基から選ばれる少なくとも1種と、-O-、-CO-、-COO-、-OCO-、-NH-および-S-から選ばれる少なくとも1種とを組み合わせた基などが挙げられ、アルキレン基であることが好ましい。アルキレン基の炭素数は、1~30が好ましく、1~20がより好ましく、1~15が更に好ましい。アルキレン基は、直鎖、分岐、環状のいずれでもよい。アルキレン基およびアリーレン基は置換基を有していてもよい。置換基としては、ヒドロキシ基などが挙げられる。
In formula (Ac-1), the divalent linking group represented by L 2 includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these. Examples include groups combining two or more of the following. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxy group. The divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-. L 2a is an alkylene group; an arylene group; a group combining an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group, and -O-, -CO-, -COO-, -OCO-, Examples include a group combining at least one selected from -NH- and -S-, and an alkylene group is preferred. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxy group.
式(Ac-2)においてAr10が表す芳香族カルボキシ基を含む基としては、式(Ac-1)のAr1と同義であり、好ましい範囲も同様である。
The aromatic carboxy group-containing group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
式(Ac-2)においてL11は、-COO-または-CONH-を表し、-COO-を表すことが好ましい。
In formula (Ac-2), L 11 represents -COO- or -CONH-, preferably -COO-.
式(Ac-2)においてL12が表す3価の連結基としては、炭化水素基、-O-、-CO-、-COO-、-OCO-、-NH-、-S-およびこれらの2種以上を組み合わせた基が挙げられる。炭化水素基は、脂肪族炭化水素基、芳香族炭化水素基が挙げられる。脂肪族炭化水素基の炭素数は、1~30が好ましく、1~20がより好ましく、1~15が更に好ましい。脂肪族炭化水素基は、直鎖、分岐、環状のいずれでもよい。芳香族炭化水素基の炭素数は、6~30が好ましく、6~20がより好ましく、6~10が更に好ましい。炭化水素基は置換基を有していてもよい。置換基としては、ヒドロキシ基などが挙げられる。L12が表す3価の連結基は、式(L12-1)で表される基であることが好ましく、式(L12-2)で表される基であることがより好ましい。
The trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these two groups. Examples include groups that combine more than one species. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 10 carbon atoms. The hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group. The trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula (L12-2).
式(L12-1)中、L12bは3価の連結基を表し、X1はSを表し、*1は式(Ac-2)のL11との結合位置を表し、*2は式(Ac-2)のP10との結合位置を表す。L12bが表す3価の連結基としては、炭化水素基;炭化水素基と、-O-、-CO-、-COO-、-OCO-、-NH-および-S-から選ばれる少なくとも1種とを組み合わせた基などが挙げられ、炭化水素基または炭化水素基と-O-とを組み合わせた基であることが好ましい。
In formula (L12-1), L 12b represents a trivalent linking group, X 1 represents S, *1 represents the bonding position with L 11 of formula (Ac-2), and *2 represents formula ( It represents the bonding position of Ac-2) with P10 . The trivalent linking group represented by L 12b is a hydrocarbon group; a hydrocarbon group, and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-. A hydrocarbon group or a group consisting of a hydrocarbon group and -O- is preferable.
式(L12-2)中、L12cは3価の連結基を表し、X1はSを表し、*1は式(Ac-2)のL11との結合位置を表し、*2は式(Ac-2)のP10との結合位置を表す。L12cが表す3価の連結基としては、炭化水素基;炭化水素基と、-O-、-CO-、-COO-、-OCO-、-NH-および-S-から選ばれる少なくとも1種とを組み合わせた基などが挙げられ、炭化水素基であることが好ましい。
In formula (L12-2), L 12c represents a trivalent linking group, X 1 represents S, *1 represents the bonding position with L 11 of formula (Ac-2), and *2 represents the bonding position of formula (Ac-2). It represents the bonding position of Ac-2) with P10 . The trivalent linking group represented by L 12c is a hydrocarbon group; a hydrocarbon group and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-. A hydrocarbon group is preferable.
式(Ac-2)においてP10はポリマー鎖を表す。P10が表すポリマー鎖は、ポリ(メタ)アクリル繰り返し単位、ポリエーテル繰り返し単位、ポリエステル繰り返し単位およびポリオール繰り返し単位から選ばれる少なくとも1種の繰り返し単位を有することが好ましい。ポリマー鎖P10の重量平均分子量は500~20000が好ましい。下限は1000以上が好ましい。上限は10000以下が好ましく、5000以下がより好ましく、3000以下が更に好ましい。P10の重量平均分子量が上記範囲であれば組成物中における顔料の分散性が良好である。芳香族カルボキシ基を有する樹脂が式(Ac-2)で表される繰り返し単位を有する樹脂である場合は、この樹脂は分散剤として好ましく用いられる。
In formula (Ac-2), P 10 represents a polymer chain. The polymer chain represented by P 10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units, and polyol repeating units. The weight average molecular weight of the polymer chain P 10 is preferably 500 to 20,000. The lower limit is preferably 1000 or more. The upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less. If the weight average molecular weight of P 10 is within the above range, the pigment will have good dispersibility in the composition. When the resin having an aromatic carboxyl group is a resin having a repeating unit represented by formula (Ac-2), this resin is preferably used as a dispersant.
P10が表すポリマー鎖は、架橋性基を含んでいてもよい。架橋性基としては、エチレン性不飽和結合含有基および環状エーテル基が挙げられる。
The polymer chain represented by P 10 may contain a crosslinkable group. Examples of the crosslinkable group include ethylenically unsaturated bond-containing groups and cyclic ether groups.
本発明の着色組成物は、分散剤としての樹脂を含有することが好ましい。分散剤としては、酸性分散剤(酸性樹脂)、塩基性分散剤(塩基性樹脂)が挙げられる。ここで、酸性分散剤(酸性樹脂)とは、酸基の量が塩基性基の量よりも多い樹脂を表す。酸性分散剤(酸性樹脂)としては、酸基の量と塩基性基の量の合計量を100モル%としたときに、酸基の量が70モル%以上である樹脂が好ましい。酸性分散剤(酸性樹脂)が有する酸基は、カルボキシ基が好ましい。酸性分散剤(酸性樹脂)の酸価は、10~105mgKOH/gが好ましい。また、塩基性分散剤(塩基性樹脂)とは、塩基性基の量が酸基の量よりも多い樹脂を表す。塩基性分散剤(塩基性樹脂)としては、酸基の量と塩基性基の量の合計量を100モル%としたときに、塩基性基の量が50モル%を超える樹脂が好ましい。塩基性分散剤が有する塩基性基は、アミノ基が好ましい。
The colored composition of the present invention preferably contains a resin as a dispersant. Examples of the dispersant include acidic dispersants (acidic resins) and basic dispersants (basic resins). Here, the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups. The acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol % or more when the total amount of acid groups and basic groups is 100 mol %. The acid group that the acidic dispersant (acidic resin) has is preferably a carboxy group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g. Moreover, the basic dispersant (basic resin) refers to a resin in which the amount of basic groups is greater than the amount of acid groups. The basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of acid groups and basic groups is 100 mol%. The basic group that the basic dispersant has is preferably an amino group.
分散剤として用いる樹脂は、グラフト樹脂であることも好ましい。グラフト樹脂の詳細については、特開2012-255128号公報の段落番号0025~0094の記載を参酌でき、この内容は本明細書に組み込まれる。
It is also preferable that the resin used as a dispersant is a graft resin. For details of the graft resin, the descriptions in paragraphs 0025 to 0094 of JP-A No. 2012-255128 can be referred to, the contents of which are incorporated herein.
分散剤として用いる樹脂は、芳香族カルボキシ基を有する樹脂(樹脂Ac)であることも好ましい。芳香族カルボキシ基を有する樹脂としては上述したものが挙げられる。
It is also preferable that the resin used as the dispersant is a resin having an aromatic carboxy group (resin Ac). Examples of the resin having an aromatic carboxy group include those mentioned above.
分散剤として用いる樹脂は、主鎖及び側鎖の少なくとも一方に窒素原子を含むポリイミン系分散剤であることも好ましい。ポリイミン系分散剤としては、pKa14以下の官能基を有する部分構造を有する主鎖と、原子数40~10000の側鎖とを有し、かつ主鎖及び側鎖の少なくとも一方に塩基性窒素原子を有する樹脂が好ましい。塩基性窒素原子は、塩基性を呈する窒素原子であれば特に制限はない。ポリイミン系分散剤については、特開2012-255128号公報の段落番号0102~0166の記載を参酌でき、この内容は本明細書に組み込まれる。
It is also preferable that the resin used as a dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. The polyimine dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain. Preferably, the resin has The basic nitrogen atom is not particularly limited as long as it exhibits basicity. Regarding the polyimine dispersant, the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
分散剤として用いる樹脂は、コア部に複数個のポリマー鎖が結合した構造の樹脂であることも好ましい。このような樹脂としては、例えば、デンドリマー(星型ポリマーを含む)が挙げられる。また、デンドリマーの具体例としては、特開2013-043962号公報の段落番号0196~0209に記載された高分子化合物C-1~C-31などが挙げられる。
It is also preferable that the resin used as the dispersant has a structure in which a plurality of polymer chains are bonded to the core portion. Examples of such resins include dendrimers (including star-shaped polymers). Further, specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraph numbers 0196 to 0209 of JP-A No. 2013-043962.
分散剤として用いる樹脂は、エチレン性不飽和結合含有基を側鎖に有する繰り返し単位を含む樹脂であることも好ましい。エチレン性不飽和結合含有基を側鎖に有する繰り返し単位の含有量は、樹脂の全繰り返し単位中10モル%以上であることが好ましく、10~80モル%であることがより好ましく、20~70モル%であることが更に好ましい。
The resin used as a dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in its side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in its side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and more preferably 20 to 70 mol% of the total repeating units of the resin. More preferably, it is mol%.
分散剤として、特開2018-087939号公報に記載された樹脂、特許第6432077号公報の段落番号0219~0221に記載されたブロック共重合体(EB-1)~(EB-9)、国際公開第2016/104803号に記載のポリエステル側鎖を有するポリエチレンイミン、国際公開第2019/125940号に記載のブロック共重合体、特開2020-066687号公報に記載のアクリルアミド構造単位を有するブロックポリマー、特開2020-066688号公報に記載のアクリルアミド構造単位を有するブロックポリマー、国際公開第2016/104803号に記載の分散剤などを用いることもできる。
As a dispersant, resins described in JP 2018-087939, block copolymers (EB-1) to (EB-9) described in paragraph numbers 0219 to 0221 of Patent No. 6432077, and international publication Polyethyleneimine having a polyester side chain described in No. 2016/104803, block copolymer described in International Publication No. 2019/125940, block polymer having an acrylamide structural unit described in JP 2020-066687, A block polymer having an acrylamide structural unit described in JP-A No. 2020-066688, a dispersant described in International Publication No. 2016/104803, etc. can also be used.
分散剤は、市販品としても入手可能であり、そのような具体例としては、BYKChemie社製のDISPERBYKシリーズ、日本ルーブリゾール社製のSOLSPERSEシリーズ、BASF社製のEfkaシリーズ、味の素ファインテクノ(株)製のアジスパーシリーズ等が挙げられる。また、特開2012-137564号公報の段落番号0129に記載された製品、特開2017-194662号公報の段落番号0235に記載された製品を分散剤として用いることもできる。
Dispersants are also available as commercial products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Japan Lubrizol, the Efka series manufactured by BASF, and Ajinomoto Fine Techno Co., Ltd. Examples include the Ajisper series manufactured by Manufacturer. Further, the product described in paragraph number 0129 of JP 2012-137564A and the product described in paragraph number 0235 of JP 2017-194662A can also be used as a dispersant.
着色組成物の全固形分中における樹脂の含有量は、1~60質量%であることが好ましい。下限は5質量%以上が好ましく、10質量%以上がより好ましく、15質量%以上が更に好ましく、20質量%以上が特に好ましい。上限は50質量%以下が好ましく、40質量%以下がより好ましい。
また、着色組成物の全固形分中における酸基を有する樹脂の含有量は、1~60質量%であることが好ましい。下限は5質量%以上が好ましく、10質量%以上がより好ましく、15質量%以上が更に好ましく、20質量%以上が特に好ましい。上限は50質量%以下が好ましく、40質量%以下がより好ましい。 The content of resin in the total solid content of the coloring composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
Further, the content of the resin having acid groups in the total solid content of the coloring composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
また、着色組成物の全固形分中における酸基を有する樹脂の含有量は、1~60質量%であることが好ましい。下限は5質量%以上が好ましく、10質量%以上がより好ましく、15質量%以上が更に好ましく、20質量%以上が特に好ましい。上限は50質量%以下が好ましく、40質量%以下がより好ましい。 The content of resin in the total solid content of the coloring composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
Further, the content of the resin having acid groups in the total solid content of the coloring composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
分散剤の含有量は、顔料100質量部に対して10~100質量部であることが好ましい。下限は15質量部以上が好ましく、20質量部以上がより好ましい。上限は80質量部以下が好ましく、60質量部以下がより好ましい。
本発明の着色組成物は、樹脂を1種のみ含んでいてもよいし、2種以上含んでいてもよい。樹脂を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。 The content of the dispersant is preferably 10 to 100 parts by weight per 100 parts by weight of the pigment. The lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more. The upper limit is preferably 80 parts by mass or less, more preferably 60 parts by mass or less.
The colored composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more types of resin are included, the total amount thereof is preferably within the above range.
本発明の着色組成物は、樹脂を1種のみ含んでいてもよいし、2種以上含んでいてもよい。樹脂を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。 The content of the dispersant is preferably 10 to 100 parts by weight per 100 parts by weight of the pigment. The lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more. The upper limit is preferably 80 parts by mass or less, more preferably 60 parts by mass or less.
The colored composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more types of resin are included, the total amount thereof is preferably within the above range.
<<溶剤>>
本発明の着色組成物は、溶剤を含有する。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。 <<Solvent>>
The colored composition of the present invention contains a solvent. Examples of the solvent include organic solvents. The type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For these details, paragraph number 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein. Ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxy Butanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as Examples include diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol. However, it may be better to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons (for example, 50 mass ppm (parts) based on the total amount of organic solvents). per million), 10 mass ppm or less, and 1 mass ppm or less).
本発明の着色組成物は、溶剤を含有する。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、2-ペンタノン、3-ペンタノン、4-ヘプタノン、シクロヘキサノン、2-メチルシクロヘキサノン、3-メチルシクロヘキサノン、4-メチルシクロヘキサノン、シクロヘプタノン、シクロオクタノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミド、プロピレングリコールジアセテート、3-メトキシブタノール、メチルエチルケトン、ガンマブチロラクトン、スルホラン、アニソール、1,4-ジアセトキシブタン、ジエチレングリコールモノエチルエーテルアセタート、二酢酸ブタン-1,3-ジイル、ジプロピレングリコールメチルエーテルアセタート、ジアセトンアルコール(別名としてダイアセトンアルコール、4-ヒドロキシ-4-メチル-2-ペンタノン)、2-メトキシプロピルアセテート、2-メトキシ-1-プロパノール、イソプロピルアルコールなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。 <<Solvent>>
The colored composition of the present invention contains a solvent. Examples of the solvent include organic solvents. The type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For these details, paragraph number 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein. Ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxy Butanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as Examples include diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol. However, it may be better to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons (for example, 50 mass ppm (parts) based on the total amount of organic solvents). per million), 10 mass ppm or less, and 1 mass ppm or less).
本発明においては、金属含有量の少ない有機溶剤を用いることが好ましい。有機溶剤の金属含有量は、例えば、10質量ppb(parts per billion)以下であることが好ましい。必要に応じて質量ppt(parts per trillion)レベルの有機溶剤を用いてもよく、そのような有機溶剤は,例えば、東洋合成社が提供している(化学工業日報、2015年11月13日)。
In the present invention, it is preferable to use an organic solvent with a low metal content. It is preferable that the metal content of the organic solvent is, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by Toyo Gosei Co., Ltd. (Kagaku Kogyo Nippo, November 13, 2015). .
有機溶剤から金属等の不純物を除去する方法としては、例えば、蒸留(分子蒸留や薄膜蒸留等)やフィルタを用いたろ過を挙げることができる。ろ過に用いるフィルタのフィルタ孔径としては、10μm以下が好ましく、5μm以下がより好ましく、3μm以下が更に好ましい。フィルタの材質は、ポリテトラフロロエチレン、ポリエチレンまたはナイロンが好ましい。
Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter. The filter pore diameter of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon.
有機溶剤は、異性体(原子数が同じであるが構造が異なる化合物)が含まれていてもよい。また、異性体は、1種のみが含まれていてもよいし、複数種含まれていてもよい。
The organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one type of isomer may be included, or multiple types may be included.
有機溶剤中の過酸化物の含有率が0.8mmol/L以下であることが好ましく、過酸化物を実質的に含まないことがより好ましい。
It is preferable that the content of peroxide in the organic solvent is 0.8 mmol/L or less, and it is more preferable that the organic solvent contains substantially no peroxide.
着色組成物中における溶剤の含有量は、10~95質量%であることが好ましく、20~90質量%であることがより好ましく、30~90質量%であることが更に好ましい。
The content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
また、本発明の着色組成物は、環境規制の観点から環境規制物質を実質的に含有しないことが好ましい。なお、本発明において、環境規制物質を実質的に含有しないとは、着色組成物中における環境規制物質の含有量が50質量ppm以下であることを意味し、30質量ppm以下であることが好ましく、10質量ppm以下であることが更に好ましく、1質量ppm以下であることが特に好ましい。環境規制物質は、例えば、ベンゼン;トルエン、キシレン等のアルキルベンゼン類;クロロベンゼン等のハロゲン化ベンゼン類等が挙げられる。これらは、REACH(Registration Evaluation Authorization and Restriction of CHemicals)規則、PRTR(Pollutant Release and Transfer Register)法、VOC(Volatile Organic Compounds)規制等のもとに環境規制物質として登録されており、使用量や取り扱い方法が厳しく規制されている。これらの化合物は、着色組成物に用いられる各成分などを製造する際に溶媒として用いられることがあり、残留溶媒として着色組成物中に混入することがある。人への安全性、環境への配慮の観点よりこれらの物質は可能な限り低減することが好ましい。環境規制物質を低減する方法としては、系中を加熱や減圧して環境規制物質の沸点以上にして系中から環境規制物質を留去して低減する方法が挙げられる。また、少量の環境規制物質を留去する場合においては、効率を上げる為に該当溶媒と同等の沸点を有する溶媒と共沸させることも有用である。また、ラジカル重合性を有する化合物を含有する場合、減圧留去中にラジカル重合反応が進行して分子間で架橋してしまうことを抑制するために重合禁止剤等を添加して減圧留去してもよい。これらの留去方法は、原料の段階、原料を反応させた生成物(例えば、重合した後の樹脂溶液や多官能モノマー溶液)の段階、またはこれらの化合物を混ぜて作製した着色組成物の段階などのいずれの段階でも可能である。
Furthermore, from the viewpoint of environmental regulations, it is preferable that the colored composition of the present invention does not substantially contain environmentally regulated substances. In the present invention, "not substantially containing environmentally controlled substances" means that the content of environmentally controlled substances in the coloring composition is 50 mass ppm or less, preferably 30 mass ppm or less. , more preferably 10 mass ppm or less, particularly preferably 1 mass ppm or less. Examples of environmentally controlled substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are REACH (Registration Evaluation Authorization and Restriction of CHemicals) rules, PRTR (Pollutant Release and It is registered as an environmentally regulated substance under the Transfer Register Act, VOC (Volatile Organic Compounds) regulations, etc., and its usage and handling are The methods are strictly regulated. These compounds may be used as a solvent when producing each component used in the coloring composition, and may be mixed into the coloring composition as a residual solvent. From the viewpoint of human safety and environmental considerations, it is preferable to reduce the amount of these substances as much as possible. Examples of methods for reducing environmentally controlled substances include a method of heating or reducing pressure in the system to raise the temperature above the boiling point of the environmentally controlled substance to distill off the environmentally controlled substances from the system. Furthermore, when distilling off a small amount of environmentally regulated substances, it is also useful to carry out azeotropy with a solvent having the same boiling point as the relevant solvent in order to increase efficiency. In addition, if a compound that has radical polymerizability is contained, a polymerization inhibitor or the like may be added to prevent the radical polymerization reaction from proceeding during vacuum distillation and crosslinking between molecules. You can. These distillation methods can be used at the stage of raw materials, at the stage of products obtained by reacting raw materials (for example, resin solution or polyfunctional monomer solution after polymerization), or at the stage of colored compositions prepared by mixing these compounds. This is possible at any stage.
<<重合性化合物>>
本発明の着色組成物は、重合性化合物を含有することが好ましい。重合性化合物としては、エチレン性不飽和結合含有基を有する化合物などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。 <<Polymerizable compound>>
The colored composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and the like. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.
本発明の着色組成物は、重合性化合物を含有することが好ましい。重合性化合物としては、エチレン性不飽和結合含有基を有する化合物などが挙げられる。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。 <<Polymerizable compound>>
The colored composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and the like. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.
重合性化合物としては、モノマー、プレポリマー、オリゴマーなどの化学的形態のいずれであってもよいが、モノマーが好ましい。重合性化合物の分子量は、100~3000が好ましい。上限は、2000以下がより好ましく、1500以下が更に好ましい。下限は、150以上がより好ましく、250以上が更に好ましい。
The polymerizable compound may be in any chemical form such as a monomer, prepolymer, or oligomer, but monomers are preferred. The molecular weight of the polymerizable compound is preferably 100 to 3,000. The upper limit is more preferably 2000 or less, and even more preferably 1500 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.
重合性化合物は、エチレン性不飽和結合含有基を3個以上含む化合物であることが好ましく、エチレン性不飽和結合含有基を3~15個含む化合物であることがより好ましく、エチレン性不飽和結合含有基を3~6個含む化合物であることが更に好ましい。また、重合性化合物は、3~15官能の(メタ)アクリレート化合物であることが好ましく、3~6官能の(メタ)アクリレート化合物であることがより好ましい。重合性化合物の具体例としては、国際公開第2022/065215号の段落番号0075~0083に記載の化合物が挙げられる。
The polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, More preferably, it is a compound containing 3 to 6 containing groups. Further, the polymerizable compound is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound. Specific examples of polymerizable compounds include compounds described in paragraph numbers 0075 to 0083 of International Publication No. 2022/065215.
重合性化合物としては、ジペンタエリスリトールトリ(メタ)アクリレート(市販品としてはKAYARAD D-330;日本化薬(株)製)、ジペンタエリスリトールテトラ(メタ)アクリレート(市販品としてはKAYARAD D-320;日本化薬(株)製)、ジペンタエリスリトールペンタ(メタ)アクリレート(市販品としてはKAYARAD D-310;日本化薬(株)製)、ジペンタエリスリトールヘキサ(メタ)アクリレート(市販品としてはKAYARAD DPHA;日本化薬(株)製、NKエステルA-DPH-12E;新中村化学工業(株)製)、およびこれらの(メタ)アクリロイル基がエチレングリコールおよび/またはプロピレングリコール残基を介して結合している構造の化合物(例えば、サートマー社から市販されている、SR454、SR499)が好ましい。また、重合性化合物としては、ジグリセリンEO(エチレンオキシド)変性(メタ)アクリレート(市販品としてはM-460;東亞合成製)、ペンタエリスリトールテトラアクリレート(新中村化学工業(株)製、NKエステルA-TMMT)、1,6-ヘキサンジオールジアクリレート(日本化薬(株)製、KAYARAD HDDA)、RP-1040(日本化薬(株)製)、アロニックスTO-2349(東亞合成(株)製)、NKオリゴUA-7200(新中村化学工業(株)製)、DPHA-40H(日本化薬(株)製)、UA-306H、UA-306T、UA-306I、AH-600、T-600、AI-600、LINC-202UA(共栄社化学(株)製)、8UH-1006、8UH-1012(以上、大成ファインケミカル(株)製)、ライトアクリレートPOB-A0(共栄社化学(株)製)などを用いることもできる。
Examples of polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product: KAYARAD D-320) ; made by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (as a commercial product KAYARAD D-310; made by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (as a commercial product KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.; NK ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), and these (meth)acryloyl groups via ethylene glycol and/or propylene glycol residues. Compounds with a bonded structure (eg, SR454, SR499, commercially available from Sartomer) are preferred. In addition, as polymerizable compounds, diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (manufactured by Shin Nakamura Chemical Co., Ltd., NK Ester A), -TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.) , NK Oligo UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), etc. are used. You can also do that.
着色組成物の全固形分中における重合性化合物の含有量は1~35質量%であることが好ましい。上限は、30質量%以下であることが好ましく、25質量%以下であることがより好ましい。下限は、2質量%以上であることが好ましく、5質量%以上であることがより好ましい。本発明の着色組成物は、重合性化合物を、1種のみ含んでいてもよいし、2種以上含んでいてもよい。重合性化合物を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
The content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 35% by mass. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more. The colored composition of the present invention may contain only one kind of polymerizable compound, or may contain two or more kinds of polymerizable compounds. When two or more types of polymerizable compounds are included, it is preferable that the total amount thereof falls within the above range.
<<光重合開始剤>>
本発明の着色組成物は光重合開始剤を含有することができる。本発明の着色組成物が重合性化合物を含む場合、本発明の着色組成物は更に光重合開始剤を含有することが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。 <<Photopolymerization initiator>>
The colored composition of the present invention can contain a photopolymerization initiator. When the colored composition of the present invention contains a polymerizable compound, it is preferable that the colored composition of the present invention further contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet to visible range are preferred. The photopolymerization initiator is preferably a radical photopolymerization initiator.
本発明の着色組成物は光重合開始剤を含有することができる。本発明の着色組成物が重合性化合物を含む場合、本発明の着色組成物は更に光重合開始剤を含有することが好ましい。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。 <<Photopolymerization initiator>>
The colored composition of the present invention can contain a photopolymerization initiator. When the colored composition of the present invention contains a polymerizable compound, it is preferable that the colored composition of the present invention further contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet to visible range are preferred. The photopolymerization initiator is preferably a radical photopolymerization initiator.
光重合開始剤としては、ハロゲン化炭化水素誘導体(例えば、トリアジン骨格を有する化合物、オキサジアゾール骨格を有する化合物など)、アシルホスフィン化合物、ヘキサアリールビイミダゾール化合物、オキシム化合物、有機過酸化物、チオ化合物、ケトン化合物、芳香族オニウム塩、α-ヒドロキシケトン化合物、α-アミノケトン化合物などが挙げられる。光重合開始剤は、露光感度の観点から、トリハロメチルトリアジン化合物、ベンジルジメチルケタール化合物、α-ヒドロキシケトン化合物、α-アミノケトン化合物、アシルホスフィン化合物、ホスフィンオキサイド化合物、メタロセン化合物、オキシム化合物、ヘキサアリールビイミダゾール化合物、オニウム化合物、ベンゾチアゾール化合物、ベンゾフェノン化合物、アセトフェノン化合物、シクロペンタジエン-ベンゼン-鉄錯体、ハロメチルオキサジアゾール化合物および3-アリール置換クマリン化合物であることが好ましく、オキシム化合物、α-ヒドロキシケトン化合物、α-アミノケトン化合物、および、アシルホスフィン化合物から選ばれる化合物であることがより好ましく、オキシム化合物であることが更に好ましい。また、光重合開始剤としては、特開2014-130173号公報の段落0065~0111に記載された化合物、特許第6301489号公報に記載された化合物、MATERIAL STAGE 37~60p,vol.19,No.3,2019に記載されたパーオキサイド系光重合開始剤、国際公開第2018/221177号に記載の光重合開始剤、国際公開第2018/110179号に記載の光重合開始剤、特開2019-043864号公報に記載の光重合開始剤、特開2019-044030号公報に記載の光重合開始剤、特開2019-167313号公報に記載の過酸化物系開始剤、特開2020-055992号公報に記載のオキサゾリジン基を有するアミノアセトフェノン系開始剤、特開2013-190459号公報に記載のオキシム系光重合開始剤、特開2020-172619号公報に記載の重合体、国際公開第2020/152120号に記載の式1で表される化合物、特開2021-181406号公報に記載の化合物、特開2022-013379号公報に記載の光重合開始剤、特開2022-015747号公報に記載の式(1)で表される化合物、特表2021-507058号公報に記載のフッ素含有フルオレンオキシムエステル系光開始剤、中国特許出願公開第110764367号明細書に記載の開始剤、特表2022-518535号公報に記載の開始剤、国際公開第2021/175855号に記載の開始剤などが挙げられる。
Examples of photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, and the like. From the viewpoint of exposure sensitivity, photopolymerization initiators include trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, and hexaarylbylene compounds. Preferred are imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl substituted coumarin compounds, oxime compounds, α-hydroxyketones The compound is more preferably a compound selected from a compound, an α-aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound. In addition, as photopolymerization initiators, compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37 to 60p, vol. 19, No. 3,2019, the photopolymerization initiator described in International Publication No. 2018/221177, the photopolymerization initiator described in International Publication No. 2018/110179, JP 2019-043864 The photopolymerization initiator described in JP-A No. 2019-044030, the peroxide-based initiator described in JP-A No. 2019-167313, the photopolymerization initiator described in JP-A No. 2020-055992 The aminoacetophenone initiator having an oxazolidine group as described, the oxime photopolymerization initiator described in JP 2013-190459, the polymer described in JP 2020-172619, the WO 2020/152120 The compound represented by the formula 1 described in JP-A No. 2021-181406, the photopolymerization initiator described in JP-A No. 2022-013379, the formula (1) described in JP-A No. 2022-015747 ), the fluorine-containing fluorene oxime ester photoinitiator described in Japanese Patent Publication No. 2021-507058, the initiator described in China Patent Application Publication No. 110764367, the initiator described in Japanese Patent Publication No. 2022-518535 Examples include the initiator described in WO 2021/175855, and the like.
ヘキサアリールビイミダゾール化合物の具体例としては、2,2’,4-トリス(2-クロロフェニル)-5-(3,4-ジメトキシフェニル)-4,5-ジフェニル-1,1’-ビイミダゾールなどが挙げられる。
Specific examples of hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc. can be mentioned.
α-ヒドロキシケトン化合物の市販品としては、Omnirad 184、Omnirad 1173、Omnirad 2959、Omnirad 127(以上、IGM Resins B.V.社製)、Irgacure 184、Irgacure 1173、Irgacure 2959、Irgacure 127(以上、BASF社製)などが挙げられる。α-アミノケトン化合物の市販品としては、Omnirad 907、Omnirad 369、Omnirad 369E、Omnirad 379EG(以上、IGM Resins B.V.社製)、Irgacure 907、Irgacure 369、Irgacure 369E、Irgacure 379EG(以上、BASF社製)などが挙げられる。アシルホスフィン化合物の市販品としては、Omnirad 819、Omnirad TPO(以上、IGM Resins B.V.社製)、Irgacure 819、Irgacure TPO(以上、BASF社製)などが挙げられる。
Commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, and Irgacure 117. 3, Irgacure 2959, Irgacure 127 (all BASF (manufactured by a company). Commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, and Irgacure 36. 9, Irgacure 369E, Irgacure 379EG (all manufactured by BASF) (manufactured by). Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (manufactured by BASF), and the like.
オキシム化合物としては、国際公開第2022/085485号の段落番号0142に記載の化合物、特許第5430746号に記載の化合物、特許第5647738号に記載の化合物、特開2021-173858号公報の一般式(1)で表される化合物や段落0022から0024に記載の化合物、特開2021-170089号公報の一般式(1)で表される化合物や段落0117から0120に記載の化合物などが挙げられる。オキシム化合物の具体例としては、3-ベンゾイルオキシイミノブタン-2-オン、3-アセトキシイミノブタン-2-オン、3-プロピオニルオキシイミノブタン-2-オン、2-アセトキシイミノペンタン-3-オン、2-アセトキシイミノ-1-フェニルプロパン-1-オン、2-ベンゾイルオキシイミノ-1-フェニルプロパン-1-オン、3-(4-トルエンスルホニルオキシ)イミノブタン-2-オン、2-エトキシカルボニルオキシイミノ-1-フェニルプロパン-1-オン、1-[4-(フェニルチオ)フェニル]-3-シクロヘキシル-プロパン-1,2-ジオン-2-(O-アセチルオキシム)などが挙げられる。市販品としては、Irgacure OXE01、Irgacure OXE02、Irgacure OXE03、Irgacure OXE04(以上、BASF社製)、TR-PBG-301、TR-PBG-304、TR-PBG-327(TRONLY社製)、アデカオプトマーN-1919((株)ADEKA製、特開2012-014052号公報に記載の光重合開始剤2)が挙げられる。また、オキシム化合物としては、着色性が無い化合物や、透明性が高く変色し難い化合物を用いることも好ましい。市販品としては、アデカアークルズNCI-730、NCI-831、NCI-930(以上、(株)ADEKA製)などが挙げられる。
Examples of oxime compounds include the compound described in paragraph number 0142 of International Publication No. 2022/085485, the compound described in Patent No. 5430746, the compound described in Patent No. 5647738, and the general formula ( Examples include the compound represented by 1), the compound described in paragraphs 0022 to 0024, the compound represented by general formula (1) and the compound described in paragraphs 0117 to 0120 of JP-A-2021-170089. Specific examples of oxime compounds include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04 (manufactured by BASF), TR-PBG-301, TR-PBG-304, TR-PBG-327 (manufactured by TRONLY). ), Adeka Optomer N-1919 (manufactured by ADEKA Co., Ltd., photopolymerization initiator 2) described in JP-A-2012-014052 can be mentioned. Further, as the oxime compound, it is also preferable to use a compound without coloring property or a compound with high transparency and resistance to discoloration. Commercially available products include ADEKA Arkles NCI-730, NCI-831, and NCI-930 (manufactured by ADEKA Co., Ltd.).
光重合開始剤としては、フルオレン環を有するオキシム化合物、カルバゾール環の少なくとも1つのベンゼン環がナフタレン環となった骨格を有するオキシム化合物、フッ素原子を有するオキシム化合物、ニトロ基を有するオキシム化合物、ベンゾフラン骨格を有するオキシム化合物、カルバゾール骨格にヒドロキシ基を有する置換基が結合したオキシム化合物、国際公開第2022/085485号の段落番号0143~0149に記載の化合物を用いることもできる。
Examples of photopolymerization initiators include oxime compounds having a fluorene ring, oxime compounds having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring, oxime compounds having a fluorine atom, oxime compounds having a nitro group, and benzofuran skeleton. An oxime compound having a carbazole skeleton bonded with a substituent having a hydroxy group, and compounds described in paragraph numbers 0143 to 0149 of International Publication No. 2022/085485 can also be used.
本発明において好ましく使用されるオキシム化合物の具体例を以下に示すが、本発明はこれらに限定されるものではない。
Specific examples of oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
オキシム化合物は、波長350~500nmの範囲に極大吸収波長を有する化合物が好ましく、波長360~480nmの範囲に極大吸収波長を有する化合物がより好ましい。また、オキシム化合物の波長365nm又は波長405nmにおけるモル吸光係数は、感度の観点から、高いことが好ましく、1000~300000であることがより好ましく、2000~300000であることが更に好ましく、5000~200000であることが特に好ましい。化合物のモル吸光係数は、公知の方法を用いて測定することができる。例えば、分光光度計(Varian社製Cary-5 spectrophotometer)にて、酢酸エチル溶媒を用い、0.01g/Lの濃度で測定することが好ましい。
The oxime compound is preferably a compound having a maximum absorption wavelength in a wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in a wavelength range of 360 to 480 nm. In addition, from the viewpoint of sensitivity, the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably from 1000 to 300,000, even more preferably from 2000 to 300,000, and even more preferably from 5000 to 200,000. It is particularly preferable that there be. The molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g/L.
光重合開始剤としては、2官能あるいは3官能以上の光ラジカル重合開始剤を用いてもよい。そのような光ラジカル重合開始剤を用いることにより、光ラジカル重合開始剤の1分子から2つ以上のラジカルが発生するため、良好な感度が得られる。また、非対称構造の化合物を用いた場合においては、結晶性が低下して溶剤などへの溶解性が向上して、経時で析出しにくくなり、着色組成物の経時安定性を向上させることができる。2官能あるいは3官能以上の光ラジカル重合開始剤の具体例としては、国際公開第2022/065215号の段落0148に記載の化合物が挙げられる。
As the photopolymerization initiator, a difunctional, trifunctional or more functional photoradical polymerization initiator may be used. By using such a radical photopolymerization initiator, two or more radicals are generated from one molecule of the radical photopolymerization initiator, so that good sensitivity can be obtained. In addition, when a compound with an asymmetric structure is used, the crystallinity decreases and the solubility in solvents improves, making it difficult to precipitate over time, thereby improving the stability of the coloring composition over time. . Specific examples of bifunctional or trifunctional or more functional photoradical polymerization initiators include compounds described in paragraph 0148 of International Publication No. 2022/065215.
着色組成物の全固形分中における光重合開始剤の含有量は0.1~30質量%が好ましい。下限は、0.5質量%以上が好ましく、1質量%以上がより好ましい。上限は、20質量%以下が好ましく、15質量%以下がより好ましい。本発明の着色組成物において、光重合開始剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
The content of the photopolymerization initiator in the total solid content of the colored composition is preferably 0.1 to 30% by mass. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. In the colored composition of the present invention, only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount falls within the above range.
<<赤外線吸収剤>>
本発明の着色組成物は、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。 <<Infrared absorber>>
The colored composition of the present invention can further contain an infrared absorber. For example, when forming an infrared transmitting filter using the colored composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorber in the colored composition is shifted to the longer wavelength side. can be done. The infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm. The infrared absorber is preferably a compound having a maximum absorption wavelength in a range of more than 700 nm and less than 1800 nm. Further, the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less. .
本発明の着色組成物は、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。 <<Infrared absorber>>
The colored composition of the present invention can further contain an infrared absorber. For example, when forming an infrared transmitting filter using the colored composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorber in the colored composition is shifted to the longer wavelength side. can be done. The infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm. The infrared absorber is preferably a compound having a maximum absorption wavelength in a range of more than 700 nm and less than 1800 nm. Further, the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less. .
赤外線吸収剤としては、ピロロピロール化合物、シアニン化合物、スクアリリウム化合物、フタロシアニン化合物、ナフタロシアニン化合物、クアテリレン化合物、メロシアニン化合物、クロコニウム化合物、オキソノール化合物、イミニウム化合物、ジチオール化合物、トリアリールメタン化合物、ピロメテン化合物、アゾメチン化合物、アントラキノン化合物、ジベンゾフラノン化合物、ジチオレン金属錯体、金属酸化物、金属ホウ化物等が挙げられる。これらの具体例としては、国際公開第2022/065215号の段落番号0114~0121に記載の化合が挙げられる。また、赤外線吸収剤としては、国際公開第2022/065215号の段落番号0121に記載の化合物、特開2020-075959号公報に記載されたスクアリリウム化合物、韓国公開特許第10-2019-0135217号公報に記載の銅錯体などを用いることもできる。また、特開2021-195515号公報に記載のクロコン酸化合物、特開2022-022070号公報に記載の赤外線吸収剤、国際公開第2019/021767号に記載のクロコニウム化合物を用いることもできる。
Infrared absorbers include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like. Specific examples of these include compounds described in paragraph numbers 0114 to 0121 of International Publication No. 2022/065215. In addition, as an infrared absorber, the compound described in paragraph number 0121 of International Publication No. 2022/065215, the squarylium compound described in JP-A No. 2020-075959, and the squarylium compound described in Korean Patent Publication No. 10-2019-0135217 The copper complexes described above can also be used. In addition, the croconic acid compound described in JP 2021-195515, the infrared absorber described in JP 2022-022070, and the croconium compound described in WO 2019/021767 can also be used.
赤外線吸収剤として、欧州特許第3628645号明細書の段落番号0025に記載の下記式で表される酸化タングステンを用いることもできる。
M1 aM2 bWcOd(P(O)nRm)e
M1、M2はアンモニウムカチオンまたは金属カチオンを表し、aは0.01~0.5であり、bは0~0.5であり、cは1であり、dは2.5~3であり、eは0.01~0.75であり、nは1、2または3であり、mは1、2または3であり、Rは、置換基を有していてもよい炭化水素基を表す。 As the infrared absorber, tungsten oxide represented by the following formula described in paragraph number 0025 of European Patent No. 3,628,645 can also be used.
M 1 a M 2 b W c O d (P(O) n R m ) e
M 1 and M 2 represent ammonium cations or metal cations, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, and d is 2.5 to 3. , e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent. represent.
M1 aM2 bWcOd(P(O)nRm)e
M1、M2はアンモニウムカチオンまたは金属カチオンを表し、aは0.01~0.5であり、bは0~0.5であり、cは1であり、dは2.5~3であり、eは0.01~0.75であり、nは1、2または3であり、mは1、2または3であり、Rは、置換基を有していてもよい炭化水素基を表す。 As the infrared absorber, tungsten oxide represented by the following formula described in paragraph number 0025 of European Patent No. 3,628,645 can also be used.
M 1 a M 2 b W c O d (P(O) n R m ) e
M 1 and M 2 represent ammonium cations or metal cations, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, and d is 2.5 to 3. , e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent. represent.
着色組成物の全固形分中における赤外線吸収剤の含有量は、1~40質量%であることが好ましい。下限は2質量%以上が好ましく、5質量%以上がより好ましく、10質量%以上であることが更に好ましい。上限は30質量%以下が好ましく、25質量%以下がより好ましい。本発明の着色組成物は、赤外線吸収剤を1種のみ含んでいてもよいし、2種以上含んでいてもよい。赤外線吸収剤を2種以上含む場合は、それらの合計量が上記範囲となることが好ましい。
The content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40% by mass. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less. The colored composition of the present invention may contain only one type of infrared absorber, or may contain two or more types of infrared absorbers. When two or more types of infrared absorbers are included, the total amount thereof is preferably within the above range.
<<環状エーテル基を有する化合物>>
本発明の着色組成物は、環状エーテル基を有する化合物を含有することができる。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられる。環状エーテル基を有する化合物は、エポキシ基を有する化合物(以下、エポキシ化合物ともいう)であることが好ましい。エポキシ化合物としては、1分子内にエポキシ基を1つ以上有する化合物が挙げられ、エポキシ基を2つ以上有する化合物が好ましい。エポキシ化合物はエポキシ基を1分子内に1~100個有する化合物であることが好ましい。エポキシ化合物に含まれるエポキシ基の上限は、例えば、10個以下とすることもでき、5個以下とすることもできる。エポキシ化合物に含まれるエポキシ基の下限は、2個以上が好ましい。エポキシ化合物としては、特開2013-011869号公報の段落番号0034~0036、特開2014-043556号公報の段落番号0147~0156、特開2014-089408号公報の段落番号0085~0092に記載された化合物、特開2017-179172号公報に記載された化合物、特開2021-195421号公報に記載のキサンテン型エポキシ樹脂、特開2021-195422号公報に記載のキサンテン型エポキシ樹脂を用いることもできる。 <<Compound having a cyclic ether group>>
The colored composition of the present invention can contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound). Examples of the epoxy compound include compounds having one or more epoxy groups in one molecule, and preferably compounds having two or more epoxy groups. The epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule. The upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less. The lower limit of the epoxy groups contained in the epoxy compound is preferably two or more. Examples of epoxy compounds include those described in paragraph numbers 0034 to 0036 of JP2013-011869, paragraphs 0147 to 0156 of JP2014-043556, and paragraphs 0085 to 0092 of JP2014-089408. Compounds, compounds described in JP 2017-179172, xanthene type epoxy resins described in JP 2021-195421, and xanthene epoxy resins described in JP 2021-195422 can also be used.
本発明の着色組成物は、環状エーテル基を有する化合物を含有することができる。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられる。環状エーテル基を有する化合物は、エポキシ基を有する化合物(以下、エポキシ化合物ともいう)であることが好ましい。エポキシ化合物としては、1分子内にエポキシ基を1つ以上有する化合物が挙げられ、エポキシ基を2つ以上有する化合物が好ましい。エポキシ化合物はエポキシ基を1分子内に1~100個有する化合物であることが好ましい。エポキシ化合物に含まれるエポキシ基の上限は、例えば、10個以下とすることもでき、5個以下とすることもできる。エポキシ化合物に含まれるエポキシ基の下限は、2個以上が好ましい。エポキシ化合物としては、特開2013-011869号公報の段落番号0034~0036、特開2014-043556号公報の段落番号0147~0156、特開2014-089408号公報の段落番号0085~0092に記載された化合物、特開2017-179172号公報に記載された化合物、特開2021-195421号公報に記載のキサンテン型エポキシ樹脂、特開2021-195422号公報に記載のキサンテン型エポキシ樹脂を用いることもできる。 <<Compound having a cyclic ether group>>
The colored composition of the present invention can contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound). Examples of the epoxy compound include compounds having one or more epoxy groups in one molecule, and preferably compounds having two or more epoxy groups. The epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule. The upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less. The lower limit of the epoxy groups contained in the epoxy compound is preferably two or more. Examples of epoxy compounds include those described in paragraph numbers 0034 to 0036 of JP2013-011869, paragraphs 0147 to 0156 of JP2014-043556, and paragraphs 0085 to 0092 of JP2014-089408. Compounds, compounds described in JP 2017-179172, xanthene type epoxy resins described in JP 2021-195421, and xanthene epoxy resins described in JP 2021-195422 can also be used.
エポキシ化合物は、低分子化合物(例えば、分子量2000未満、さらには、分子量1000未満)でもよいし、高分子化合物(macromolecule)(例えば、分子量1000以上、ポリマーの場合は、重量平均分子量が1000以上)でもよい。エポキシ基を有する化合物の重量平均分子量は、200~100000が好ましく、500~50000がより好ましい。重量平均分子量の上限は、10000以下がさらに好ましく、5000以下が特に好ましく、3000以下が一層好ましい。
The epoxy compound may be a low-molecular compound (for example, molecular weight less than 2000, or even less than 1000), or a macromolecule (for example, molecular weight 1000 or more; in the case of a polymer, the weight average molecular weight is 1000 or more). But that's fine. The weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000. The upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and even more preferably 3,000 or less.
環状エーテル基を有する化合物の市販品としては、例えば、EHPE3150((株)ダイセル製)、EPICLON N-695(DIC(株)製)、マープルーフG-0150M、G-0105SA、G-0130SP、G-0250SP、G-1005S、G-1005SA、G-1010S、G-2050M、G-01100、G-01758(以上、日油(株)製、エポキシ基含有ポリマー)等が挙げられる。
Commercially available compounds having a cyclic ether group include, for example, EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, and G-0130SP. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all of which are epoxy group-containing polymers manufactured by NOF Corporation).
着色組成物の全固形分中における環状エーテル基を有する化合物の含有量は、0.1~20質量%が好ましい。下限は、0.5質量%以上が好ましく、1質量%以上がより好ましい。上限は、15質量%以下が好ましく、10質量%以下がより好ましい。環状エーテル基を有する化合物は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、それらの合計量が上記範囲となることが好ましい。
The content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 10% by mass or less. Only one kind of compound having a cyclic ether group may be used, or two or more kinds thereof may be used. When two or more types are used, it is preferable that their total amount falls within the above range.
<<ポリアルキレンイミン>>
本発明の着色組成物は、ポリアルキレンイミンを含有することもできる。ポリアルキレンイミンは例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。ポリアルキレンイミンとは、アルキレンイミンを開環重合したポリマーのことである。ポリアルキレンイミンは、1級アミノ基と、2級アミノ基と、3級アミノ基とをそれぞれ含む分岐構造を有するポリマーである。アルキレンイミンの炭素数は2~6が好ましく、2~4がより好ましく、2または3であることが更に好ましく、2であることが特に好ましい。 <<Polyalkyleneimine>>
The colored composition of the present invention can also contain polyalkyleneimine. Polyalkyleneimines are used, for example, as dispersion aids for pigments. A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition. Polyalkyleneimine is a polymer obtained by ring-opening polymerization of alkyleneimine. Polyalkyleneimine is a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group, respectively. The alkylene imine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, even more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
本発明の着色組成物は、ポリアルキレンイミンを含有することもできる。ポリアルキレンイミンは例えば顔料の分散助剤として用いられる。分散助剤とは、着色組成物中において顔料の分散性を高めるための素材のことである。ポリアルキレンイミンとは、アルキレンイミンを開環重合したポリマーのことである。ポリアルキレンイミンは、1級アミノ基と、2級アミノ基と、3級アミノ基とをそれぞれ含む分岐構造を有するポリマーである。アルキレンイミンの炭素数は2~6が好ましく、2~4がより好ましく、2または3であることが更に好ましく、2であることが特に好ましい。 <<Polyalkyleneimine>>
The colored composition of the present invention can also contain polyalkyleneimine. Polyalkyleneimines are used, for example, as dispersion aids for pigments. A dispersion aid is a material for improving the dispersibility of pigments in a coloring composition. Polyalkyleneimine is a polymer obtained by ring-opening polymerization of alkyleneimine. Polyalkyleneimine is a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group, respectively. The alkylene imine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, even more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.
ポリアルキレンイミンの分子量は、200以上であることが好ましく、250以上であることがより好ましい。上限は、100000以下であることが好ましく、50000以下であることがより好ましく、10000以下であることが更に好ましく、2000以下であることが特に好ましい。なお、ポリアルキレンイミンの分子量の値について、構造式から分子量が計算できる場合は、ポリアルキレンイミンの分子量は構造式から計算した値である。一方、特定アミン化合物の分子量が構造式から計算できない、あるいは、計算が困難な場合には、沸点上昇法で測定した数平均分子量の値を用いる。また、沸点上昇法でも測定できない、あるいは、測定が困難な場合は、粘度法で測定した数平均分子量の値を用いる。また、粘度法でも測定できない、あるいは、粘度法での測定が困難な場合は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値での数平均分子量の値を用いる。
The molecular weight of the polyalkylene imine is preferably 200 or more, more preferably 250 or more. The upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less. Regarding the value of the molecular weight of polyalkylene imine, if the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkylene imine is the value calculated from the structural formula. On the other hand, if the molecular weight of a specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used. In addition, if measurement cannot be performed by the boiling point elevation method or is difficult to measure, the value of the number average molecular weight measured by the viscosity method is used. If the viscosity method cannot be used or it is difficult to measure, the number average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography) is used.
ポリアルキレンイミンのアミン価は5mmol/g以上であることが好ましく、10mmol/g以上であることがより好ましく、15mmol/g以上であることが更に好ましい。
The amine value of the polyalkylene imine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
アルキレンイミンの具体例としては、エチレンイミン、プロピレンイミン、1,2-ブチレンイミン、2,3-ブチレンイミンなどが挙げられ、エチレンイミンまたはプロピレンイミンであることが好ましく、エチレンイミンであることがより好ましい。ポリアルキレンイミンは、ポリエチレンイミンであることが特に好ましい。また、ポリエチレンイミンは、1級アミノ基を、1級アミノ基と2級アミノ基と3級アミノ基との合計に対して10モル%以上含むことが好ましく、20モル%以上含むことがより好ましく、30モル%以上含むことが更に好ましい。ポリエチレンイミンの市販品としては、エポミンSP-003、SP-006、SP-012、SP-018、SP-200、P-1000(以上、(株)日本触媒製)などが挙げられる。
Specific examples of alkyleneimine include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine, etc. Ethyleneimine or propyleneimine is preferable, and ethyleneimine is more preferable. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. Further, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more of primary amino groups based on the total of primary amino groups, secondary amino groups, and tertiary amino groups. , more preferably 30 mol% or more. Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
着色組成物の全固形分中におけるポリアルキレンイミンの含有量は0.1~5質量%であることが好ましい。下限は0.2質量%以上であることが好ましく、0.5質量%以上であることがより好ましく、1質量%以上であることが更に好ましい。上限は4.5質量%以下であることが好ましく、4質量%以下であることがより好ましく、3質量%以下であることが更に好ましい。また、ポリアルキレンイミンの含有量は、顔料100質量部に対して0.5~20質量部であることが好ましい。下限は0.6質量部以上であることが好ましく、1質量部以上であることがより好ましく、2質量部以上であることが更に好ましい。上限は10質量部以下であることが好ましく、8質量部以下であることがより好ましい。ポリアルキレンイミンは、1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合はそれらの合計量が上記範囲であることが好ましい。
The content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass. The lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less. Further, the content of polyalkyleneimine is preferably 0.5 to 20 parts by weight per 100 parts by weight of the pigment. The lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. The upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one type of polyalkylene imine may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
<<硬化促進剤>>
本発明の着色組成物は、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2022/085485号の段落0164に記載の化合物、特開2021-181406号公報に記載の化合物などが挙げられる。着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%が好ましく、0.8~6.4質量%がより好ましい。 <<Curing accelerator>>
The colored composition of the present invention may also contain a curing accelerator. Examples of the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds, and the like. Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485, the compound described in JP 2021-181406, and the like. The content of the curing accelerator in the total solid content of the colored composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
本発明の着色組成物は、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2022/085485号の段落0164に記載の化合物、特開2021-181406号公報に記載の化合物などが挙げられる。着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%が好ましく、0.8~6.4質量%がより好ましい。 <<Curing accelerator>>
The colored composition of the present invention may also contain a curing accelerator. Examples of the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds, and the like. Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485, the compound described in JP 2021-181406, and the like. The content of the curing accelerator in the total solid content of the colored composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
<<紫外線吸収剤>>
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物、ジベンゾイル化合物などが挙げられる。このような化合物の具体例としては、国際公開第2022/085485号の段落番号0179に記載の化合物、特開2021-178918号公報に記載の反応性トリアジン紫外線吸収剤、特開2022-007884号公報に記載の紫外線吸収剤を用いることもできる。着色組成物の全固形分中における紫外線吸収剤の含有量は、0.01~10質量%が好ましく、0.01~5質量%がより好ましい。本発明において、紫外線吸収剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 <<Ultraviolet absorber>>
The colored composition of the present invention can contain an ultraviolet absorber. Examples of the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, dibenzoyl compounds, and the like. Specific examples of such compounds include the compound described in paragraph number 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorber described in JP 2021-178918, and JP 2022-007884. It is also possible to use the ultraviolet absorbers described in . The content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. In the present invention, only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤としては、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物、ジベンゾイル化合物などが挙げられる。このような化合物の具体例としては、国際公開第2022/085485号の段落番号0179に記載の化合物、特開2021-178918号公報に記載の反応性トリアジン紫外線吸収剤、特開2022-007884号公報に記載の紫外線吸収剤を用いることもできる。着色組成物の全固形分中における紫外線吸収剤の含有量は、0.01~10質量%が好ましく、0.01~5質量%がより好ましい。本発明において、紫外線吸収剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 <<Ultraviolet absorber>>
The colored composition of the present invention can contain an ultraviolet absorber. Examples of the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, dibenzoyl compounds, and the like. Specific examples of such compounds include the compound described in paragraph number 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorber described in JP 2021-178918, and JP 2022-007884. It is also possible to use the ultraviolet absorbers described in . The content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. In the present invention, only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
<<重合禁止剤>>
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<Polymerization inhibitor>>
The colored composition of the present invention can contain a polymerization inhibitor. Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), Examples include 2,2'-methylenebis(4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. The number of polymerization inhibitors may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<Polymerization inhibitor>>
The colored composition of the present invention can contain a polymerization inhibitor. Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), Examples include 2,2'-methylenebis(4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. The number of polymerization inhibitors may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
<<シランカップリング剤>>
本発明の着色組成物は、シランカップリング剤を含有することができる。シランカップリング剤としては、加水分解性基を有するシラン化合物が挙げられ、加水分解性基とそれ以外の官能基とを有するシラン化合物であることが好ましい。加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、国際公開第2022/085485号の段落0177に記載の化合物が挙げられる。着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%が好ましく、0.05~10.0質量%がより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<Silane coupling agent>>
The colored composition of the present invention can contain a silane coupling agent. Examples of the silane coupling agent include silane compounds having a hydrolyzable group, and preferably silane compounds having a hydrolyzable group and other functional groups. The hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, and an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, ureido groups, sulfide groups, and isocyanate groups. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferable. Specific examples of the silane coupling agent include compounds described in paragraph 0177 of International Publication No. 2022/085485. The content of the silane coupling agent in the total solid content of the colored composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. Only one type of silane coupling agent may be used, or two or more types may be used. In the case of two or more types, it is preferable that the total amount falls within the above range.
本発明の着色組成物は、シランカップリング剤を含有することができる。シランカップリング剤としては、加水分解性基を有するシラン化合物が挙げられ、加水分解性基とそれ以外の官能基とを有するシラン化合物であることが好ましい。加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、国際公開第2022/085485号の段落0177に記載の化合物が挙げられる。着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%が好ましく、0.05~10.0質量%がより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。 <<Silane coupling agent>>
The colored composition of the present invention can contain a silane coupling agent. Examples of the silane coupling agent include silane compounds having a hydrolyzable group, and preferably silane compounds having a hydrolyzable group and other functional groups. The hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, and an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, ureido groups, sulfide groups, and isocyanate groups. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferable. Specific examples of the silane coupling agent include compounds described in paragraph 0177 of International Publication No. 2022/085485. The content of the silane coupling agent in the total solid content of the colored composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. Only one type of silane coupling agent may be used, or two or more types may be used. In the case of two or more types, it is preferable that the total amount falls within the above range.
<<界面活性剤>>
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤を参照することができ、この内容は本明細書に組み込まれる。 <<Surfactant>>
The colored composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used. The surfactant is preferably a silicone surfactant or a fluorine surfactant. Regarding the surfactant, reference can be made to the surfactants described in paragraph numbers 0238 to 0245 of International Publication No. 2015/166779, the contents of which are incorporated herein.
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤はシリコーン系界面活性剤またはフッ素系界面活性剤であることが好ましい。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤を参照することができ、この内容は本明細書に組み込まれる。 <<Surfactant>>
The colored composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used. The surfactant is preferably a silicone surfactant or a fluorine surfactant. Regarding the surfactant, reference can be made to the surfactants described in paragraph numbers 0238 to 0245 of International Publication No. 2015/166779, the contents of which are incorporated herein.
フッ素系界面活性剤としては、国際公開第2022/085485号の段落番号0167~0173に記載の化合物を用いることができる。
As the fluorosurfactant, compounds described in paragraph numbers 0167 to 0173 of International Publication No. 2022/085485 can be used.
ノニオン系界面活性剤としては、国際公開第2022/085485号の段落0174に記載の化合物が挙げられる。
Examples of nonionic surfactants include compounds described in paragraph 0174 of International Publication No. 2022/085485.
シリコーン系界面活性剤としては、DOWSIL SH8400、SH8400 FLUID、FZ-2122、67 Additive、74 Additive、M Additive、SF 8419 OIL(以上、ダウ・東レ(株)製)、TSF-4300、TSF-4445、TSF-4460、TSF-4452(以上、モメンティブ・パフォーマンス・マテリアルズ社製)、KP-341、KF-6000、KF-6001、KF-6002、KF-6003(以上、信越化学工業(株)製)、BYK-307、BYK-322、BYK-323、BYK-330、BYK-333、BYK-3760、BYK-UV3510(以上、ビックケミー社製)等が挙げられる。
Examples of silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), and TSF- 4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK Chemie), and the like.
また、シリコーン系界面活性剤には下記構造の化合物を用いることもできる。
Moreover, a compound having the following structure can also be used as the silicone surfactant.
着色組成物の全固形分中における界面活性剤の含有量は、0.001質量%~5.0質量%が好ましく、0.005~3.0質量%がより好ましい。界面活性剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。
The content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% to 3.0% by mass. The number of surfactants may be one, or two or more. In the case of two or more types, it is preferable that the total amount falls within the above range.
<<酸化防止剤>>
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物、韓国公開特許第10-2019-0059371号公報に記載された化合物を使用することもできる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 <<Antioxidant>>
The colored composition of the present invention can contain an antioxidant. Examples of antioxidants include phenol compounds, phosphite compounds, thioether compounds, and the like. As the phenol compound, any phenol compound known as a phenolic antioxidant can be used. Preferred phenol compounds include hindered phenol compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. The above-mentioned substituents are preferably substituted or unsubstituted alkyl groups having 1 to 22 carbon atoms. Further, as the antioxidant, a compound having a phenol group and a phosphorous acid ester group in the same molecule is also preferable. Further, as the antioxidant, phosphorus-based antioxidants can also be suitably used. As a phosphorus antioxidant, tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepine-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl )oxy]ethyl]amine, ethylbis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like. Commercially available antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Co., Ltd.). In addition, antioxidants include compounds described in paragraph numbers 0023 to 0048 of Patent No. 6268967, compounds described in International Publication No. 2017/006600, compounds described in International Publication No. 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used. The content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落番号0023~0048に記載された化合物、国際公開第2017/006600号に記載された化合物、国際公開第2017/164024号に記載された化合物、韓国公開特許第10-2019-0059371号公報に記載された化合物を使用することもできる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。 <<Antioxidant>>
The colored composition of the present invention can contain an antioxidant. Examples of antioxidants include phenol compounds, phosphite compounds, thioether compounds, and the like. As the phenol compound, any phenol compound known as a phenolic antioxidant can be used. Preferred phenol compounds include hindered phenol compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. The above-mentioned substituents are preferably substituted or unsubstituted alkyl groups having 1 to 22 carbon atoms. Further, as the antioxidant, a compound having a phenol group and a phosphorous acid ester group in the same molecule is also preferable. Further, as the antioxidant, phosphorus-based antioxidants can also be suitably used. As a phosphorus antioxidant, tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepine-6 -yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl )oxy]ethyl]amine, ethylbis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like. Commercially available antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Co., Ltd.). In addition, antioxidants include compounds described in paragraph numbers 0023 to 0048 of Patent No. 6268967, compounds described in International Publication No. 2017/006600, compounds described in International Publication No. 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used. The content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount falls within the above range.
<<その他成分>>
本発明の着色組成物は、必要に応じて、増感剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、国際公開第2022/085485号の段落0182に記載の化合物を用いることができる。 <<Other ingredients>>
The coloring composition of the present invention may optionally contain sensitizers, plasticizers, and other auxiliary agents (e.g., conductive particles, fillers, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances). , surface tension adjusting agent, chain transfer agent, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. As these components, the compounds described in paragraph 0182 of International Publication No. 2022/085485 can be used.
本発明の着色組成物は、必要に応じて、増感剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、国際公開第2022/085485号の段落0182に記載の化合物を用いることができる。 <<Other ingredients>>
The coloring composition of the present invention may optionally contain sensitizers, plasticizers, and other auxiliary agents (e.g., conductive particles, fillers, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances). , surface tension adjusting agent, chain transfer agent, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. As these components, the compounds described in paragraph 0182 of International Publication No. 2022/085485 can be used.
本発明の着色組成物は、得られる膜の屈折率を調整するために金属酸化物を含有させてもよい。金属酸化物としては、TiO2、ZrO2、Al2O3、SiO2等が挙げられる。金属酸化物の一次粒子径は1~100nmが好ましく、3~70nmがより好ましく、5~50nmが更に好ましい。金属酸化物はコア-シェル構造を有していてもよい。また、この場合、コア部は中空状であってもよい。
The colored composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film. Examples of metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 , and SiO 2 . The primary particle diameter of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, even more preferably 5 to 50 nm. The metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
本発明の着色組成物は、耐光性改良剤を含んでもよい。耐光性改良剤としては、国際公開第2022/085485号の段落番号0183に記載の化合物が挙げられる。
The colored composition of the present invention may also contain a lightfastness improver. Examples of the light resistance improver include compounds described in paragraph number 0183 of International Publication No. 2022/085485.
本発明の着色組成物は、テレフタル酸エステルを実質的に含まないことも好ましい。ここで、「実質的に含まない」とは、テレフタル酸エステルの含有量が、着色組成物の全量中、1000質量ppb以下であることを意味し、100質量ppb以下であることがより好ましく、ゼロであることが特に好ましい。
It is also preferable that the colored composition of the present invention is substantially free of terephthalic acid ester. Here, "substantially not containing" means that the content of terephthalic acid ester is 1000 mass ppb or less in the total amount of the coloring composition, more preferably 100 mass ppb or less, Particularly preferred is zero.
本発明の着色組成物は、遊離の金属含有量が100ppm以下であることが好ましく、50ppm以下であることがより好ましい。金属の種類は特に限定されないが、アルカリ金属、アルカリ土類金属、遷移金属、Al、Sn、Pb、Biなどが挙げられる。また、遊離のハロゲン含有量は100ppm以下であることが好ましく、50ppm以下であることがより好ましい。着色組成物中の遊離の金属やハロゲンの低減方法としては、イオン交換水による洗浄、ろ過、限外ろ過、イオン交換樹脂による精製等の方法が挙げられる。
The colored composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less. The type of metal is not particularly limited, but examples include alkali metals, alkaline earth metals, transition metals, Al, Sn, Pb, Bi, and the like. Further, the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less. Examples of methods for reducing free metals and halogens in the colored composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification using ion-exchange resins.
環境規制の観点から、パーフルオロアルキルスルホン酸及びその塩、並びにパーフルオロアルキルカルボン酸及びその塩の使用が規制されることがある。本発明の着色組成物において、上記した化合物の含有率を小さくする場合、パーフルオロアルキルスルホン酸(特にパーフルオロアルキル基の炭素数が6~8のパーフルオロアルキルスルホン酸)及びその塩、並びにパーフルオロアルキルカルボン酸(特にパーフルオロアルキル基の炭素数が6~8のパーフルオロアルキルカルボン酸)及びその塩の含有率は、着色組成物の全固形分に対して、0.01ppb~1,000ppbの範囲であることが好ましく、0.05ppb~500ppbの範囲であることがより好ましく、0.1ppb~300ppbの範囲であることが更に好ましい。本発明の着色組成物は、パーフルオロアルキルスルホン酸及びその塩、並びにパーフルオロアルキルカルボン酸及びその塩を実質的に含まなくてもよい。例えば、パーフルオロアルキルスルホン酸及びその塩の代替となりうる化合物、並びにパーフルオロアルキルカルボン酸及びその塩の代替となりうる化合物を用いることで、パーフルオロアルキルスルホン酸及びその塩、並びにパーフルオロアルキルカルボン酸及びその塩を実質的に含まない着色組成物を選択してもよい。規制化合物の代替となりうる化合物としては、例えば、パーフルオロアルキル基の炭素数の違いによって規制対象から除外された化合物が挙げられる。ただし、上記した内容は、パーフルオロアルキルスルホン酸及びその塩、並びにパーフルオロアルキルカルボン酸及びその塩の使用を妨げるものではない。本発明の着色組成物は、許容される最大の範囲内で、パーフルオロアルキルスルホン酸及びその塩、並びにパーフルオロアルキルカルボン酸及びその塩を含んでもよい。
From the perspective of environmental regulations, the use of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts may be regulated. In the coloring composition of the present invention, when reducing the content of the above-mentioned compounds, perfluoroalkylsulfonic acids (particularly perfluoroalkylsulfonic acids whose perfluoroalkyl group has 6 to 8 carbon atoms), salts thereof, and perfluoroalkylsulfonic acids, The content of fluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid whose perfluoroalkyl group has 6 to 8 carbon atoms) and its salt is 0.01 ppb to 1,000 ppb based on the total solid content of the coloring composition. It is preferably in the range of , more preferably in the range of 0.05 ppb to 500 ppb, even more preferably in the range of 0.1 ppb to 300 ppb. The coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt. For example, by using a compound that can be substituted for perfluoroalkylsulfonic acid and its salt, and a compound that can be substituted for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid You may select a coloring composition that is substantially free of and salts thereof. Compounds that can be substituted for regulated compounds include, for example, compounds that are excluded from regulated targets due to differences in the number of carbon atoms in perfluoroalkyl groups. However, the above content does not preclude the use of perfluoroalkylsulfonic acids and salts thereof, and perfluoroalkylcarboxylic acids and salts thereof. The colored compositions of the present invention may include perfluoroalkyl sulfonic acids and salts thereof, and perfluoroalkyl carboxylic acids and salts thereof, to the maximum extent permissible.
本発明の着色組成物の含水率は、通常3質量%以下であり、0.01~1.5質量%が好ましく、0.1~1.0質量%の範囲であることがより好ましい。含水率は、カールフィッシャー法にて測定することができる。
The water content of the colored composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.
本発明の着色組成物は、膜面状(平坦性など)の調整、膜厚の調整などを目的として粘度を調整して用いることができる。粘度の値は必要に応じて適宜選択することができるが、例えば、25℃において0.3mPa・s~50mPa・sが好ましく、0.5mPa・s~20mPa・sがより好ましい。粘度の測定方法としては、例えば、コーンプレートタイプの粘度計を使用し、25℃に温度調整を施した状態で測定することができる。
The colored composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface condition (flatness, etc.), adjusting the film thickness, etc. The value of viscosity can be appropriately selected as required, but for example, at 25° C., 0.3 mPa·s to 50 mPa·s is preferable, and 0.5 mPa·s to 20 mPa·s is more preferable. The viscosity can be measured using, for example, a cone plate type viscometer with the temperature adjusted to 25°C.
<<収容容器>>
着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、国際公開第2022/085485号の段落0187に記載の容器を用いることができる。 <<Storage container>>
The container for storing the coloring composition is not particularly limited, and any known container can be used. Further, as the storage container, the container described in paragraph 0187 of International Publication No. 2022/085485 can be used.
着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、国際公開第2022/085485号の段落0187に記載の容器を用いることができる。 <<Storage container>>
The container for storing the coloring composition is not particularly limited, and any known container can be used. Further, as the storage container, the container described in paragraph 0187 of International Publication No. 2022/085485 can be used.
<着色組成物の調製方法>
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。 <Method for preparing colored composition>
The colored composition of the present invention can be prepared by mixing the above-mentioned components. When preparing a colored composition, the colored composition may be prepared by dissolving and/or dispersing all components in a solvent at the same time, or, if necessary, each component may be prepared as two or more solutions or dispersions as appropriate. A colored composition may be prepared by mixing these at the time of use (at the time of application).
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。 <Method for preparing colored composition>
The colored composition of the present invention can be prepared by mixing the above-mentioned components. When preparing a colored composition, the colored composition may be prepared by dissolving and/or dispersing all components in a solvent at the same time, or, if necessary, each component may be prepared as two or more solutions or dispersions as appropriate. A colored composition may be prepared by mixing these at the time of use (at the time of application).
また、着色組成物の調製に際して、顔料を分散させるプロセスを含むことが好ましい。顔料を分散させるプロセスにおいて、顔料の分散に用いる機械力としては、圧縮、圧搾、衝撃、剪断、キャビテーションなどが挙げられる。これらプロセスの具体例としては、ビーズミル、サンドミル、ロールミル、ボールミル、ペイントシェーカー、マイクロフルイダイザー、高速インペラー、サンドグラインダー、フロージェットミキサー、高圧湿式微粒化、超音波分散などが挙げられる。またサンドミル(ビーズミル)における顔料の粉砕においては、径の小さいビーズを使用する、ビーズの充填率を大きくする事等により粉砕効率を高めた条件で処理することが好ましい。また、粉砕処理後にろ過、遠心分離などで粗粒子を除去することが好ましい。また、顔料を分散させるプロセスおよび分散機は、「分散技術大全集、株式会社情報機構発行、2005年7月15日」や「サスペンション(固/液分散系)を中心とした分散技術と工業的応用の実際 総合資料集、経営開発センター出版部発行、1978年10月10日」、特開2015-157893号公報の段落番号0022に記載のプロセス及び分散機を好適に使用出来る。また顔料を分散させるプロセスにおいては、ソルトミリング工程にて粒子の微細化処理を行ってもよい。ソルトミリング工程に用いられる素材、機器、処理条件等は、例えば、特開2015-194521号公報、特開2012-046629号公報の記載を参酌できる。
Furthermore, it is preferable to include a process of dispersing pigments when preparing the colored composition. In the process of dispersing pigments, mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like. Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like. In addition, when pulverizing pigments in a sand mill (bead mill), it is preferable to use small-diameter beads or increase the filling rate of the beads, thereby increasing the pulverizing efficiency. Further, it is preferable to remove coarse particles by filtration, centrifugation, etc. after the pulverization treatment. In addition, the process and dispersion machine for dispersing pigments are described in ``Complete Works of Dispersion Technology, Published by Information Technology Corporation, July 15, 2005'' and ``Dispersion technology centered on suspension (solid/liquid dispersion system) and industrial The process and dispersion machine described in Paragraph No. 0022 of JP 2015-157893 A, "Practical Application Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be suitably used. Further, in the process of dispersing the pigment, the particles may be made finer in a salt milling step. For the materials, equipment, processing conditions, etc. used in the salt milling process, the descriptions in JP-A No. 2015-194521 and JP-A No. 2012-046629 can be referred to, for example.
着色組成物の調製にあたり、異物の除去や欠陥の低減などの目的で、着色組成物をフィルタでろ過することが好ましい。ろ過に用いるフィルタの種類およびろ過方法としては、国際公開第2022/085485号の段落番号0196~0199に記載のフィルタおよびろ過方法が挙げられる。
In preparing the colored composition, it is preferable to filter the colored composition with a filter for the purpose of removing foreign substances and reducing defects. Examples of the type of filter and filtration method used for filtration include the filters and filtration methods described in paragraph numbers 0196 to 0199 of International Publication No. 2022/085485.
<膜>
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタや赤外線透過フィルタなどの光学フィルタに用いることができる。 <Membrane>
The film of the present invention is a film obtained from the colored composition of the present invention described above. The film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタや赤外線透過フィルタなどの光学フィルタに用いることができる。 <Membrane>
The film of the present invention is a film obtained from the colored composition of the present invention described above. The film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
本発明の膜の膜厚は、目的に応じて適宜調整できる。例えば、膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下がさらに好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上がさらに好ましい。
The film thickness of the film of the present invention can be adjusted as appropriate depending on the purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.
本発明の膜をカラーフィルタとして用いる場合、本発明の膜は、緑色、赤色、青色、シアン色、マゼンタ色または黄色の色相を有することが好ましく、緑色、赤色または黄色の色相を有することがより好ましい。また、本発明の膜は、カラーフィルタの着色画素として好ましく用いることができる。着色画素としては、赤色画素、緑色画素、青色画素、マゼンタ色画素、シアン色画素、黄色画素などが挙げられ、赤色画素、緑色画素および黄色画素であることが好ましく、赤色画素または緑色画素であることがより好ましく、緑色画素であることが更に好ましい。
When the film of the present invention is used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta, or yellow hue, more preferably a green, red, or yellow hue. preferable. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc., and preferably red pixels, green pixels, and yellow pixels, and red pixels or green pixels. More preferably, it is a green pixel, and even more preferably a green pixel.
また、本発明の膜は、光透過率が50%となる波長が、470~520nmの波長範囲に存在することが好ましく、475~520nmの波長範囲に存在することがより好ましく、480~520nmの波長範囲に存在することが更に好ましい。なかでも、光透過率が50%となる波長が、470~520nmの波長範囲と、575~625nmの波長範囲のそれぞれに存在することが好ましい。この態様において、光透過率が50%となる短波長側の波長は、475~520nmの波長範囲に存在することが好ましく、480~520nmの波長範囲に存在することがより好ましい。また、光透過率が50%となる長波長側の波長は、580~620nmの波長範囲に存在することが好ましく、585~615nmの波長範囲に存在することがより好ましい。このような分光特性を有する膜は、緑色画素として好ましく用いられる。
Further, in the film of the present invention, the wavelength at which the light transmittance is 50% is preferably in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. More preferably, it exists within the wavelength range. Among these, it is preferable that the wavelength at which the light transmittance is 50% exists in the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the short wavelength at which the light transmittance is 50% is preferably in the wavelength range of 475 to 520 nm, more preferably in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side at which the light transmittance is 50% is preferably in the wavelength range of 580 to 620 nm, more preferably in the wavelength range of 585 to 615 nm. A film having such spectral characteristics is preferably used as a green pixel.
本発明の膜を赤外線透過フィルタとして用いる場合、本発明の膜は、例えば、以下の(1)~(4)のいずれかの分光特性を有することが好ましい。
(1):膜の厚み方向における光透過率の、波長400~640nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長800~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である。このような分光特性を有する膜は、波長400~640nmの範囲の光を遮光して、波長700nmを超える光を透過させることができる。
(2):膜の厚み方向における光透過率の、波長400~750nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長900~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる。
(3):膜の厚み方向における光透過率の、波長400~830nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1000~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~830nmの範囲の光を遮光して、波長940nmを超える光を透過させることができる。
(4):膜の厚み方向における光透過率の、波長400~950nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1100~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1040nmを超える光を透過させることができる。 When the film of the present invention is used as an infrared transmission filter, the film of the present invention preferably has, for example, any one of the following spectral properties (1) to (4).
(1): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is The minimum value of the ratio in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light with wavelengths exceeding 700 nm.
(2): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength exceeding 850 nm.
(3): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength exceeding 940 nm.
(4): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1040 nm.
(1):膜の厚み方向における光透過率の、波長400~640nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長800~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である。このような分光特性を有する膜は、波長400~640nmの範囲の光を遮光して、波長700nmを超える光を透過させることができる。
(2):膜の厚み方向における光透過率の、波長400~750nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長900~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる。
(3):膜の厚み方向における光透過率の、波長400~830nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1000~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~830nmの範囲の光を遮光して、波長940nmを超える光を透過させることができる。
(4):膜の厚み方向における光透過率の、波長400~950nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1100~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1040nmを超える光を透過させることができる。 When the film of the present invention is used as an infrared transmission filter, the film of the present invention preferably has, for example, any one of the following spectral properties (1) to (4).
(1): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is The minimum value of the ratio in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light with wavelengths exceeding 700 nm.
(2): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength exceeding 850 nm.
(3): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength exceeding 940 nm.
(4): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmission in the thickness direction of the film is A film having a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1040 nm.
<膜の製造方法>
次に、本発明の膜の製造方法について説明する。本発明の膜は、本発明の着色組成物を塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。 <Membrane manufacturing method>
Next, a method for manufacturing the membrane of the present invention will be explained. The film of the present invention can be manufactured through a step of applying the colored composition of the present invention. The film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of methods for forming patterns (pixels) include photolithography and dry etching, with photolithography being preferred.
次に、本発明の膜の製造方法について説明する。本発明の膜は、本発明の着色組成物を塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。 <Membrane manufacturing method>
Next, a method for manufacturing the membrane of the present invention will be explained. The film of the present invention can be manufactured through a step of applying the colored composition of the present invention. The film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of methods for forming patterns (pixels) include photolithography and dry etching, with photolithography being preferred.
フォトリソグラフィ法によるパターン形成は、本発明の着色組成物を用いて支持体上に着色組成物層を形成する工程と、着色組成物層をパターン状に露光する工程と、着色組成物層の未露光部を現像除去してパターン(画素)を形成する工程と、を含むことが好ましい。必要に応じて、着色組成物層をベークする工程(プリベーク工程)、および、現像されたパターン(画素)をベークする工程(ポストベーク工程)を設けてもよい。
Pattern formation by the photolithography method includes a step of forming a colored composition layer on a support using the colored composition of the present invention, a step of exposing the colored composition layer to light in a pattern, and a step of exposing the colored composition layer to light. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the colored composition layer (pre-bake step) and a step of baking the developed pattern (pixel) (post-bake step) may be provided.
着色組成物層を形成する工程では、本発明の着色組成物を用いて、支持体上に着色組成物層を形成する。支持体としては、特に限定は無く、用途に応じて適宜選択できる。例えば、ガラス基板、シリコン基板などが挙げられ、シリコン基板であることが好ましい。また、シリコン基板には、電荷結合素子(CCD)、相補型金属酸化膜半導体(CMOS)、透明導電膜などが形成されていてもよい。また、シリコン基板には、各画素を隔離するブラックマトリクスが形成されている場合もある。また、シリコン基板には、上部の層との密着性改良、物質の拡散防止或いは基板表面の平坦化のために下地層が設けられていてもよい。下地層の表面接触角は、ジヨードメタンで測定した際に20~70°であることが好ましい。また、水で測定した際に30~80°であることが好ましい。
In the step of forming a colored composition layer, a colored composition layer is formed on a support using the colored composition of the present invention. The support is not particularly limited and can be appropriately selected depending on the application. For example, a glass substrate, a silicon substrate, etc. may be mentioned, and a silicon substrate is preferable. Further, a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate. Further, a black matrix that isolates each pixel may be formed on the silicon substrate. Further, the silicon substrate may be provided with an underlayer for improving adhesion with the upper layer, preventing substance diffusion, or flattening the substrate surface. The surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferable that the angle is 30 to 80° when measured with water.
着色組成物の塗布方法としては、公知の方法を用いることができる。例えば、国際公開第2022/085485号の段落番号0207に記載の塗布方法を用いることができる。
A known method can be used to apply the coloring composition. For example, the coating method described in paragraph number 0207 of International Publication No. 2022/085485 can be used.
支持体上に形成した着色組成物層は、乾燥(プリベーク)してもよい。低温プロセスにより膜を製造する場合は、プリベークを行わなくてもよい。プリベークを行う場合、プリベーク温度は、150℃以下が好ましく、120℃以下がより好ましく、110℃以下が更に好ましい。下限は、例えば、50℃以上とすることができ、80℃以上とすることもできる。プリベーク時間は、10~300秒が好ましく、40~250秒がより好ましく、80~220秒がさらに好ましい。プリベークは、ホットプレート、オーブン等で行うことができる。
The colored composition layer formed on the support may be dried (prebaked). If the film is manufactured by a low-temperature process, prebaking may not be performed. When prebaking is performed, the prebaking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower. The lower limit can be, for example, 50°C or higher, or 80°C or higher. The prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Prebaking can be performed on a hot plate, oven, or the like.
次に、着色組成物層をパターン状に露光する(露光工程)。例えば、着色組成物層に対し、ステッパー露光機やスキャナ露光機などを用いて、所定のマスクパターンを有するマスクを介して露光することで、パターン状に露光することができる。これにより、露光部分を硬化することができる。
Next, the colored composition layer is exposed in a pattern (exposure step). For example, the colored composition layer can be exposed in a pattern by exposing it to light through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. This allows the exposed portion to be cured.
露光に際して用いることができる放射線(光)としては、g線、i線等が挙げられる。また、波長300nm以下の光(好ましくは波長180~300nmの光)を用いることもできる。波長300nm以下の光としては、KrF線(波長248nm)、ArF線(波長193nm)などが挙げられ、KrF線(波長248nm)が好ましい。また、300nm以上の長波な光源も利用できる。光源としては、無電極紫外線ランプシステム、紫外線と赤外線のハイブリッド硬化を使用することができる。
Radiation (light) that can be used during exposure includes g-line, i-line, etc. Furthermore, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm). Furthermore, a long-wave light source of 300 nm or more can also be used. As a light source, an electrodeless ultraviolet lamp system, a hybrid ultraviolet and infrared curing can be used.
また、露光に際して、光を連続的に照射して露光してもよく、パルス的に照射して露光(パルス露光)してもよい。なお、パルス露光とは、短時間(例えば、ミリ秒レベル以下)のサイクルで光の照射と休止を繰り返して露光する方式の露光方法のことである。
Furthermore, during exposure, light may be exposed by continuous irradiation, or exposure may be performed by irradiation in pulses (pulse exposure). Note that pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and pauses in short cycles (for example, on the millisecond level or less).
照射量(露光量)は、例えば、0.03~2.5J/cm2が好ましく、0.05~1.0J/cm2がより好ましい。露光時における酸素濃度については適宜選択することができ、大気下で行う他に、例えば、酸素濃度が19体積%以下の低酸素雰囲気下(例えば、15体積%、5体積%、または、実質的に無酸素)で露光してもよく、酸素濃度が21体積%を超える高酸素雰囲気下(例えば、22体積%、30体積%、または、50体積%)で露光してもよい。また、露光照度は適宜設定することが可能であり、通常1000W/m2~100000W/m2(例えば、5000W/m2、15000W/m2、または、35000W/m2)の範囲から選択することができる。酸素濃度と露光照度は適宜条件を組み合わせてよく、例えば、酸素濃度10体積%で照度10000W/m2、酸素濃度35体積%で照度20000W/m2などとすることができる。
The irradiation amount (exposure amount) is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 . The oxygen concentration during exposure can be appropriately selected, and in addition to being carried out in the atmosphere, for example, in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially The exposure may be performed in an oxygen-free atmosphere (without oxygen), or in a high oxygen atmosphere where the oxygen concentration exceeds 21 volume % (for example, 22 volume %, 30 volume %, or 50 volume %). Further, the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000W/m 2 to 100000W/m 2 (for example, 5000W/m 2 , 15000W/m 2 , or 35000W/m 2 ). Can be done. The oxygen concentration and the exposure illuminance may be appropriately combined. For example, the illuminance may be 10,000 W/m 2 when the oxygen concentration is 10% by volume, and 20,000 W/m 2 when the oxygen concentration is 35% by volume.
次に、着色組成物層の未露光部を現像除去してパターン(画素)を形成する。着色組成物層の未露光部の現像除去は、現像液を用いて行うことができる。これにより、露光工程における未露光部の着色組成物層が現像液に溶出し、光硬化した部分だけが残る。現像液の温度は、例えば、20~30℃が好ましい。現像時間は、20~180秒が好ましい。また、残渣除去性を向上するため、現像液を60秒ごとに振り切り、さらに新たに現像液を供給する工程を数回繰り返してもよい。
Next, the unexposed portions of the colored composition layer are developed and removed to form a pattern (pixel). The unexposed areas of the colored composition layer can be removed by development using a developer. As a result, the unexposed portions of the colored composition layer in the exposure step are eluted into the developer, leaving only the photocured portions. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. Furthermore, in order to improve the ability to remove residues, the process of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
現像液は、有機溶剤、アルカリ現像液などが挙げられ、アルカリ現像液が好ましく用いられる。現像液、および、現像後の洗浄(リンス)方法については、国際公開第2022/085485号の段落番号0214に記載の現像液や洗浄方法を用いることができる。
Examples of the developer include organic solvents, alkaline developers, and alkaline developers are preferably used. Regarding the developer and the cleaning (rinsing) method after development, the developer and cleaning method described in paragraph number 0214 of International Publication No. 2022/085485 can be used.
現像後、乾燥を施した後に追加露光処理や加熱処理(ポストベーク)を行うことが好ましい。追加露光処理やポストベークは、硬化を完全なものとするための現像後の硬化処理である。ポストベークにおける加熱温度は、例えば、100~300℃が好ましく、200~270℃がより好ましい。ポストベークは、現像後の膜を、上記条件になるようにホットプレートやコンベクションオーブン(熱風循環式乾燥機)、高周波加熱機等の加熱手段を用いて、連続式あるいはバッチ式で行うことができる。追加露光処理を行う場合、露光に用いられる光は、波長400nm以下の光であることが好ましい。また、追加露光処理は、韓国公開特許第10-2017-0122130号公報に記載された方法で行ってもよい。
After development, it is preferable to perform additional exposure treatment or heat treatment (post-bake) after drying. Additional exposure processing and post-bake are post-development curing processing to complete curing. The heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C. Post-baking can be carried out in a continuous or batch manner using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to maintain the developed film under the above conditions. . When performing additional exposure processing, the light used for exposure is preferably light with a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
ドライエッチング法でのパターン形成は、本発明の着色組成物を用いて支持体上に着色組成物層を形成し、この着色組成物層の全体を硬化させて硬化物層を形成する工程と、この硬化物層上にフォトレジスト層を形成する工程と、フォトレジスト層をパターン状に露光したのち、現像してレジストパターンを形成する工程と、このレジストパターンをマスクとして硬化物層に対してエッチングガスを用いてドライエッチングする工程と、を含むことが好ましい。フォトレジスト層の形成においては、更にプリベーク処理を施すことが好ましい。特に、フォトレジスト層の形成プロセスとしては、露光後の加熱処理、現像後の加熱処理(ポストベーク処理)を実施する形態が望ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落番号0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。
Pattern formation by the dry etching method includes the steps of forming a colored composition layer on a support using the colored composition of the present invention, and curing the entire colored composition layer to form a cured product layer; A step of forming a photoresist layer on this cured material layer, a step of exposing the photoresist layer in a pattern and then developing it to form a resist pattern, and etching the cured material layer using this resist pattern as a mask. It is preferable to include a step of dry etching using gas. In forming the photoresist layer, it is preferable to further perform a prebaking process. In particular, as a process for forming the photoresist layer, it is desirable to perform a heat treatment after exposure and a heat treatment after development (post-bake treatment). Regarding pattern formation by the dry etching method, the descriptions in paragraphs 0010 to 0067 of JP-A No. 2013-064993 can be referred to, and the contents thereof are incorporated into the present specification.
<光学フィルタ>
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタが挙げられ、カラーフィルタであることが好ましい。カラーフィルタとしては、カラーフィルタの着色画素として本発明の膜を有することが好ましい。 <Optical filter>
The optical filter of the present invention has the film of the present invention described above. Types of optical filters include color filters and infrared transmission filters, and color filters are preferred. As a color filter, it is preferable to have the film of the present invention as a colored pixel of the color filter.
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタが挙げられ、カラーフィルタであることが好ましい。カラーフィルタとしては、カラーフィルタの着色画素として本発明の膜を有することが好ましい。 <Optical filter>
The optical filter of the present invention has the film of the present invention described above. Types of optical filters include color filters and infrared transmission filters, and color filters are preferred. As a color filter, it is preferable to have the film of the present invention as a colored pixel of the color filter.
光学フィルタは、本発明の膜の表面に保護層が設けられていてもよい。保護層を設けることで、酸素遮断化、低反射化、親疎水化、特定波長の光(紫外線、近赤外線等)の遮蔽等の種々の機能を付与することができる。保護層の厚さとしては、0.01~10μmが好ましく、0.1~5μmがより好ましい。保護層の形成方法としては、有機溶剤に溶解した樹脂組成物を塗布して形成する方法、化学気相蒸着法、成型した樹脂を接着剤で貼りつける方法等が挙げられる。保護層を構成する成分としては、(メタ)アクリル樹脂、エン・チオール樹脂、ポリカーボネート樹脂、ポリエーテル樹脂、ポリアリレート樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリフェニレン樹脂、ポリアリーレンエーテルホスフィンオキシド樹脂、ポリイミド樹脂、ポリアミドイミド樹脂、ポリオレフィン樹脂、環状オレフィン樹脂、ポリエステル樹脂、スチレン樹脂、ポリオール樹脂、ポリ塩化ビニリデン樹脂、メラミン樹脂、ウレタン樹脂、アラミド樹脂、ポリアミド樹脂、アルキド樹脂、エポキシ樹脂、変性シリコーン樹脂、フッ素樹脂、ポリアクリロニトリル樹脂、セルロース樹脂、Si、C、W、Al2O3、Mo、SiO2、Si2N4などが挙げられ、これらの成分を二種以上含有しても良い。例えば、酸素遮断化を目的とした保護層の場合、保護層はポリオール樹脂と、SiO2と、Si2N4を含むことが好ましい。また、低反射化を目的とした保護層の場合、保護層は(メタ)アクリル樹脂とフッ素樹脂を含むことが好ましい。
In the optical filter, a protective layer may be provided on the surface of the film of the present invention. By providing a protective layer, various functions such as oxygen blocking, low reflection, hydrophilic and hydrophobic properties, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted. The thickness of the protective layer is preferably 0.01 to 10 μm, more preferably 0.1 to 5 μm. Examples of methods for forming the protective layer include a method of coating a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of pasting a molded resin with an adhesive. Components constituting the protective layer include (meth)acrylic resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide. Resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples include resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4 and the like, and two or more of these components may be contained. For example, in the case of a protective layer intended for oxygen blocking, the protective layer preferably contains a polyol resin, SiO 2 and Si 2 N 4 . Furthermore, in the case of a protective layer intended for low reflection, the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
樹脂組成物を塗布して保護層を形成する場合、樹脂組成物の塗布方法としては、スピンコート法、キャスト法、スクリーン印刷法、インクジェット法等の公知の方法を用いることができる。樹脂組成物に含まれる有機溶剤は、公知の有機溶剤(例えば、プロピレングリコール1-モノメチルエーテル2-アセテート、シクロペンタノン、乳酸エチル等)を用いることが出来る。保護層を化学気相蒸着法にて形成する場合、化学気相蒸着法としては、公知の化学気相蒸着法(熱化学気相蒸着法、プラズマ化学気相蒸着法、光化学気相蒸着法)を用いることができる。
When forming a protective layer by applying a resin composition, known methods such as a spin coating method, a casting method, a screen printing method, an inkjet method, etc. can be used as a method for applying the resin composition. As the organic solvent contained in the resin composition, known organic solvents (eg, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used. When forming the protective layer by chemical vapor deposition, known chemical vapor deposition methods (thermal chemical vapor deposition, plasma enhanced chemical vapor deposition, photochemical vapor deposition) can be used as the chemical vapor deposition method. can be used.
保護層は、必要に応じて、有機・無機微粒子、特定波長の光(例えば、紫外線、近赤外線等)の吸収剤、屈折率調整剤、酸化防止剤、密着剤、界面活性剤等の添加剤を含有しても良い。有機・無機微粒子の例としては、例えば、高分子微粒子(例えば、シリコーン樹脂微粒子、ポリスチレン微粒子、メラミン樹脂微粒子)、酸化チタン、酸化亜鉛、酸化ジルコニウム、酸化インジウム、酸化アルミニウム、窒化チタン、酸窒化チタン、フッ化マグネシウム、中空シリカ、シリカ、炭酸カルシウム、硫酸バリウム等が挙げられる。特定波長の光の吸収剤は公知の吸収剤を用いることができる。これらの添加剤の含有量は適宜調整できるが、保護層の全質量に対して0.1~70質量%が好ましく、1~60質量%がさらに好ましい。
The protective layer may contain organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, and other additives, as necessary. It may contain. Examples of organic/inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride. , magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, and the like. As the absorber for light of a specific wavelength, a known absorber can be used. The content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by weight, more preferably 1 to 60% by weight, based on the total weight of the protective layer.
また、保護層としては、特開2017-151176号公報の段落番号0073~0092に記載の保護層を用いることもできる。
Furthermore, as the protective layer, the protective layers described in paragraph numbers 0073 to 0092 of JP-A No. 2017-151176 can also be used.
光学フィルタは、隔壁により例えば格子状に仕切られた空間に、各画素が埋め込まれた構造を有していてもよい。
The optical filter may have a structure in which each pixel is embedded in a space partitioned into a lattice shape by partition walls, for example.
<固体撮像素子>
本発明の固体撮像素子は、上述した本発明の膜を有する。固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。 <Solid-state imaging device>
The solid-state imaging device of the present invention has the film of the present invention described above. The structure of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, but examples include the following structure.
本発明の固体撮像素子は、上述した本発明の膜を有する。固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。 <Solid-state imaging device>
The solid-state imaging device of the present invention has the film of the present invention described above. The structure of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, but examples include the following structure.
基板上に、固体撮像素子(CCD(電荷結合素子)イメージセンサ、CMOS(相補型金属酸化膜半導体)イメージセンサ等)の受光エリアを構成する複数のフォトダイオードおよびポリシリコン等からなる転送電極を有し、フォトダイオードおよび転送電極上にフォトダイオードの受光部のみ開口した遮光膜を有し、遮光膜上に遮光膜全面およびフォトダイオード受光部を覆うように形成された窒化シリコン等からなるデバイス保護膜を有し、デバイス保護膜上に、カラーフィルタを有する構成である。更に、デバイス保護膜上であってカラーフィルタの下(基板に近い側)に集光手段(例えば、マイクロレンズ等。以下同じ)を有する構成や、カラーフィルタ上に集光手段を有する構成等であってもよい。また、カラーフィルタは、隔壁により例えば格子状に仕切られた空間に、各着色画素が埋め込まれた構造を有していてもよい。この場合の隔壁は各着色画素よりも低屈折率であることが好ましい。このような構造を有する撮像装置の例としては、特開2012-227478号公報、特開2014-179577号公報、国際公開第2018/043654号に記載の装置が挙げられる。また、特開2019-211559号公報の中で示しているように固体撮像素子の構造内に紫外線吸収層を設けて耐光性を改良してもよい。本発明の固体撮像素子を備えた撮像装置は、デジタルカメラや、撮像機能を有する電子機器(携帯電話等)の他、車載カメラや監視カメラ用としても用いることができる。
The substrate has a plurality of photodiodes that constitute the light receiving area of a solid-state image sensor (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and a transfer electrode made of polysilicon or the like. A device protective film made of silicon nitride or the like is formed on the light-shielding film to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. It has a configuration in which a color filter is provided on the device protective film. Furthermore, a configuration in which a light condensing means (for example, a microlens, etc., the same applies hereinafter) is provided on the device protective film and below the color filter (on the side closer to the substrate), or a configuration in which the condensing means is provided on the color filter, etc. There may be. Further, the color filter may have a structure in which each colored pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls. In this case, the partition wall preferably has a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include devices described in Japanese Patent Application Publication No. 2012-227478, Japanese Patent Application Publication No. 2014-179577, and International Publication No. 2018/043654. Furthermore, as shown in Japanese Patent Application Laid-open No. 2019-211559, an ultraviolet absorbing layer may be provided within the structure of the solid-state image sensor to improve light resistance. An imaging device equipped with the solid-state imaging device of the present invention can be used not only as a digital camera or an electronic device having an imaging function (such as a mobile phone), but also as an in-vehicle camera or a surveillance camera.
<画像表示装置>
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。 <Image display device>
The image display device of the present invention has the film of the present invention described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. For the definition of an image display device and details of each image display device, see, for example, “Electronic Display Devices (written by Akio Sasaki, Kogyo Chosenkai Co., Ltd., published in 1990)” and “Display Devices (written by Junaki Ibuki, published by Sangyo Tosho)”. Co., Ltd., issued in 1989). Further, liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Chosenkai Co., Ltd., 1994)". There is no particular restriction on the liquid crystal display device to which the present invention can be applied, and for example, the present invention can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology."
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。 <Image display device>
The image display device of the present invention has the film of the present invention described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. For the definition of an image display device and details of each image display device, see, for example, “Electronic Display Devices (written by Akio Sasaki, Kogyo Chosenkai Co., Ltd., published in 1990)” and “Display Devices (written by Junaki Ibuki, published by Sangyo Tosho)”. Co., Ltd., issued in 1989). Further, liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Chosenkai Co., Ltd., 1994)". There is no particular restriction on the liquid crystal display device to which the present invention can be applied, and for example, the present invention can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology."
以下に実施例を挙げて本発明をさらに具体的に説明する。以下の実施例に示す材料、使用量、割合、処理内容、処理手順等は、本発明の趣旨を逸脱しない限り、適宜、変更することができる。従って、本発明の範囲は以下に示す具体例に限定されるものではない。なお、以下に示す構造式中のPhはフェニル基を表し、Meはメチル基を表し、Bnはベンジル基を表す。
The present invention will be explained in more detail with reference to Examples below. The materials, usage amounts, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In addition, Ph in the structural formula shown below represents a phenyl group, Me represents a methyl group, and Bn represents a benzyl group.
<化合物の合成例>
(合成例1) 化合物(Y-1)の合成
<Example of compound synthesis>
(Synthesis Example 1) Synthesis of compound (Y-1)
(合成例1) 化合物(Y-1)の合成
(Synthesis Example 1) Synthesis of compound (Y-1)
化合物(a-1)の15質量部に、1当量の化合物(b-1)と30質量部のジメチルホルムアミド(DMF)を添加し、窒素気流下外温45℃で2時間加熱攪拌した。生成した固体を熱時濾別した後に30質量部の水で洗浄した。得られた固体を50℃で送風乾燥し、化合物(S-1)を15.05質量部得た。続いて、化合物(S-1)の11質量部に1当量の化合物(C-1)と20質量部の酢酸を混合して窒素気流下、外温115℃で2時間加熱攪拌した。生成した固体を熱時濾別した後に30v/wのメタノールで洗浄した。得られた固体を50℃で送風乾燥し、化合物(Y-1)を12.9質量部得た。化合物(Y-1)の質量スペクトルにおける(M+H)(posi)の値は462であった。化合物(Y-1)の極大吸収波長は波長400~600nmの範囲に存在していた。
15 parts by mass of compound (a-1) was added with 1 equivalent of compound (b-1) and 30 parts by mass of dimethylformamide (DMF), and the mixture was heated and stirred under a nitrogen stream at an external temperature of 45°C for 2 hours. The resulting solid was filtered off while hot and washed with 30 parts by mass of water. The resulting solid was blown dry at 50°C to obtain 15.05 parts by mass of compound (S-1). Next, 11 parts by mass of compound (S-1) was mixed with 1 equivalent of compound (C-1) and 20 parts by mass of acetic acid, and the mixture was heated and stirred under a nitrogen stream at an external temperature of 115°C for 2 hours. The resulting solid was filtered off while hot and washed with 30 v/w of methanol. The resulting solid was blown dry at 50°C to obtain 12.9 parts by mass of compound (Y-1). The (M+H)(posi) value in the mass spectrum of compound (Y-1) was 462. The maximum absorption wavelength of compound (Y-1) was in the wavelength range of 400 to 600 nm.
(合成例2~20) 化合物(Y-2)~(Y-7)、化合物(YY-1)~化合物(YY-13)の合成
合成例1における化合物(a-1)、化合物(b-1)、化合物(c-1)および化合物(S-1)を、それぞれ下記表の化合物(a)の欄、化合物(b)の欄、化合物(c)および化合物(S)の欄に記載の化合物に変更する以外は合成例1と同様の操作を行い、化合物(Y-2)~(Y-7)、化合物(YY-1)~化合物(YY-13)を合成した。これらの化合物の極大吸収波長は波長400~600nmの範囲に存在していた。なお、化合物Sがアミノ基を有する化合物である場合には、使用している酢酸と塩を形成していることもある。 (Synthesis Examples 2 to 20) Synthesis of Compounds (Y-2) to (Y-7) and Compounds (YY-1) to Compounds (YY-13) Compound (a-1) and Compound (b- 1), compound (c-1) and compound (S-1) as described in the compound (a) column, compound (b) column, compound (c) and compound (S) column of the table below, respectively. Compounds (Y-2) to (Y-7) and compounds (YY-1) to (YY-13) were synthesized by performing the same operation as in Synthesis Example 1 except for changing the compound. The maximum absorption wavelength of these compounds existed in the wavelength range of 400 to 600 nm. In addition, when the compound S is a compound having an amino group, it may form a salt with the acetic acid used.
合成例1における化合物(a-1)、化合物(b-1)、化合物(c-1)および化合物(S-1)を、それぞれ下記表の化合物(a)の欄、化合物(b)の欄、化合物(c)および化合物(S)の欄に記載の化合物に変更する以外は合成例1と同様の操作を行い、化合物(Y-2)~(Y-7)、化合物(YY-1)~化合物(YY-13)を合成した。これらの化合物の極大吸収波長は波長400~600nmの範囲に存在していた。なお、化合物Sがアミノ基を有する化合物である場合には、使用している酢酸と塩を形成していることもある。 (Synthesis Examples 2 to 20) Synthesis of Compounds (Y-2) to (Y-7) and Compounds (YY-1) to Compounds (YY-13) Compound (a-1) and Compound (b- 1), compound (c-1) and compound (S-1) as described in the compound (a) column, compound (b) column, compound (c) and compound (S) column of the table below, respectively. Compounds (Y-2) to (Y-7) and compounds (YY-1) to (YY-13) were synthesized by performing the same operation as in Synthesis Example 1 except for changing the compound. The maximum absorption wavelength of these compounds existed in the wavelength range of 400 to 600 nm. In addition, when the compound S is a compound having an amino group, it may form a salt with the acetic acid used.
上記表に記載の略語で示した化合物は以下の通りである。
The compounds indicated by the abbreviations in the table above are as follows.
Y-1~Y-7:下記構造の化合物(Y-1)~(Y-7)
YY-1~YY-13:下記構造の化合物(YY-1)~(YY-13)
Y-1 to Y-7: Compounds (Y-1) to (Y-7) with the following structure
YY-1 to YY-13: Compounds (YY-1) to (YY-13) with the following structure
YY-1~YY-13:下記構造の化合物(YY-1)~(YY-13)
YY-1 to YY-13: Compounds (YY-1) to (YY-13) with the following structure
S-1~S-13:下記構造の化合物(S-1)~(S-13)
a-1~a-13:下記構造の化合物(a-1)~(a-13)
b-1:下記構造の化合物(b-1)
c-1~c-4:下記構造の化合物(c-1)~(c-4)
S-1 to S-13: Compounds (S-1) to (S-13) with the following structure
a-1 to a-13: Compounds (a-1) to (a-13) with the following structure
b-1: Compound (b-1) with the following structure
c-1 to c-4: Compounds (c-1) to (c-4) with the following structure
a-1~a-13:下記構造の化合物(a-1)~(a-13)
b-1:下記構造の化合物(b-1)
c-1~c-4:下記構造の化合物(c-1)~(c-4)
a-1 to a-13: Compounds (a-1) to (a-13) with the following structure
b-1: Compound (b-1) with the following structure
c-1 to c-4: Compounds (c-1) to (c-4) with the following structure
<分散液の製造>
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm2および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。なお、以下の表において、着色剤1~3、赤外線吸収剤、顔料誘導体1、2および分散剤の配合量の値は固形分換算での値である。 <Production of dispersion>
A mixture of the raw materials listed in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.1 mm in diameter). Next, dispersion treatment was carried out using a high-pressure dispersion machine NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a pressure reduction mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersion treatment was repeated a total of 10 times to obtain a dispersion liquid. In the table below, the amounts of colorants 1 to 3, infrared absorbers, pigment derivatives 1 and 2, and dispersants are calculated in terms of solid content.
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm2および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。なお、以下の表において、着色剤1~3、赤外線吸収剤、顔料誘導体1、2および分散剤の配合量の値は固形分換算での値である。 <Production of dispersion>
A mixture of the raw materials listed in the table below was mixed and dispersed for 3 hours using a bead mill (zirconia beads 0.1 mm in diameter). Next, dispersion treatment was carried out using a high-pressure dispersion machine NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a pressure reduction mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersion treatment was repeated a total of 10 times to obtain a dispersion liquid. In the table below, the amounts of colorants 1 to 3, infrared absorbers, pigment derivatives 1 and 2, and dispersants are calculated in terms of solid content.
上記表に記載の略語で示した素材の詳細は以下の通りである。
The details of the materials indicated by the abbreviations in the table above are as follows.
(着色剤)
Y-1~Y-7:上述した化合物(Y-1)~(Y-7)(ピラゾリジンジオン基を有するイソインドリン顔料)
PY185:C.I.ピグメントイエロー185(黄色顔料、イソインドリン顔料)
PG36:C.I.ピグメントグリーン36(緑色顔料、フタロシアニン顔料)
PG58:C.I.ピグメントグリーン58(緑色顔料、フタロシアニン顔料)
PG59:C.I.ピグメントグリーン59(緑色顔料、フタロシアニン顔料)
PG63:C.I.ピグメントグリーン63(緑色顔料、フタロシアニン顔料)
PR254:C.I.ピグメントレッド254(赤色顔料、ジケトピロロピロール顔料)
PR264:C.I.ピグメントレッド264(赤色顔料、ジケトピロロピロール顔料)
PR272:C.I.ピグメントレッド272(赤色顔料、ジケトピロロピロール顔料)
PY129:C.I.ピグメントイエロー129(黄色顔料、アゾメチン顔料)
PY150:C.I.ピグメントイエロー150(黄色顔料、アゾ顔料)
PO71:C.I.ピグメントオレンジ71(オレンジ色顔料、ジケトピロロピロール顔料)
PB15:6 : C.I.ピグメントブルー15:6(青色顔料、フタロシアニン顔料) (colorant)
Y-1 to Y-7: Compounds (Y-1) to (Y-7) described above (isoindoline pigments having a pyrazolidinedione group)
PY185:C. I. Pigment Yellow 185 (yellow pigment, isoindoline pigment)
PG36:C. I. Pigment Green 36 (green pigment, phthalocyanine pigment)
PG58:C. I. Pigment Green 58 (green pigment, phthalocyanine pigment)
PG59:C. I. Pigment Green 59 (green pigment, phthalocyanine pigment)
PG63:C. I. Pigment Green 63 (green pigment, phthalocyanine pigment)
PR254:C. I. Pigment Red 254 (red pigment, diketopyrrolopyrrole pigment)
PR264:C. I. Pigment Red 264 (red pigment, diketopyrrolopyrrole pigment)
PR272:C. I. Pigment Red 272 (red pigment, diketopyrrolopyrrole pigment)
PY129:C. I. Pigment Yellow 129 (yellow pigment, azomethine pigment)
PY150:C. I. Pigment Yellow 150 (yellow pigment, azo pigment)
PO71:C. I. Pigment Orange 71 (orange pigment, diketopyrrolopyrrole pigment)
PB15:6: C. I. Pigment Blue 15:6 (blue pigment, phthalocyanine pigment)
Y-1~Y-7:上述した化合物(Y-1)~(Y-7)(ピラゾリジンジオン基を有するイソインドリン顔料)
PY185:C.I.ピグメントイエロー185(黄色顔料、イソインドリン顔料)
PG36:C.I.ピグメントグリーン36(緑色顔料、フタロシアニン顔料)
PG58:C.I.ピグメントグリーン58(緑色顔料、フタロシアニン顔料)
PG59:C.I.ピグメントグリーン59(緑色顔料、フタロシアニン顔料)
PG63:C.I.ピグメントグリーン63(緑色顔料、フタロシアニン顔料)
PR254:C.I.ピグメントレッド254(赤色顔料、ジケトピロロピロール顔料)
PR264:C.I.ピグメントレッド264(赤色顔料、ジケトピロロピロール顔料)
PR272:C.I.ピグメントレッド272(赤色顔料、ジケトピロロピロール顔料)
PY129:C.I.ピグメントイエロー129(黄色顔料、アゾメチン顔料)
PY150:C.I.ピグメントイエロー150(黄色顔料、アゾ顔料)
PO71:C.I.ピグメントオレンジ71(オレンジ色顔料、ジケトピロロピロール顔料)
PB15:6 : C.I.ピグメントブルー15:6(青色顔料、フタロシアニン顔料) (colorant)
Y-1 to Y-7: Compounds (Y-1) to (Y-7) described above (isoindoline pigments having a pyrazolidinedione group)
PY185:C. I. Pigment Yellow 185 (yellow pigment, isoindoline pigment)
PG36:C. I. Pigment Green 36 (green pigment, phthalocyanine pigment)
PG58:C. I. Pigment Green 58 (green pigment, phthalocyanine pigment)
PG59:C. I. Pigment Green 59 (green pigment, phthalocyanine pigment)
PG63:C. I. Pigment Green 63 (green pigment, phthalocyanine pigment)
PR254:C. I. Pigment Red 254 (red pigment, diketopyrrolopyrrole pigment)
PR264:C. I. Pigment Red 264 (red pigment, diketopyrrolopyrrole pigment)
PR272:C. I. Pigment Red 272 (red pigment, diketopyrrolopyrrole pigment)
PY129:C. I. Pigment Yellow 129 (yellow pigment, azomethine pigment)
PY150:C. I. Pigment Yellow 150 (yellow pigment, azo pigment)
PO71:C. I. Pigment Orange 71 (orange pigment, diketopyrrolopyrrole pigment)
PB15:6: C. I. Pigment Blue 15:6 (blue pigment, phthalocyanine pigment)
(赤外線吸収剤)
IR-1:下記構造の化合物
(Infrared absorber)
IR-1: Compound with the following structure
IR-1:下記構造の化合物
IR-1: Compound with the following structure
(顔料誘導体)
YY-1~YY-13:上述した化合物(YY-1)~(YY-13)
yyr-1:下記構造の化合物(比較誘導体)
A-1~A-6:下記構造の化合物
(pigment derivative)
YY-1 to YY-13: the above-mentioned compounds (YY-1) to (YY-13)
yyr-1: Compound with the following structure (comparative derivative)
A-1 to A-6: Compounds with the following structure
YY-1~YY-13:上述した化合物(YY-1)~(YY-13)
yyr-1:下記構造の化合物(比較誘導体)
YY-1 to YY-13: the above-mentioned compounds (YY-1) to (YY-13)
yyr-1: Compound with the following structure (comparative derivative)
(分散剤)
B-1:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量24000)
B-2:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量10000)
B-3:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量20000)
B-4:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量16000)
B-5:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量20000)
B-6:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量7000)
B-7:以下の方法で合成した樹脂
還流冷却器、滴下ロートおよび撹拌機を備えたフラスコ内に窒素を適量流し、窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の340質量部を入れ、撹拌しながら80℃まで加熱した。次いで、アクリル酸の57質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレートおよび3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)の54質量部、ベンジルメタクリレートの239質量部、PGMEAの73質量部の混合溶液を5時間かけて滴下した。次いで、重合開始剤(2,2-アゾビス(2,4-ジメチルバレロニトリル))の40質量部をPGMEAの197質量部に溶解した溶液を6時間かけて滴下した。重合開始剤溶液の滴下終了後、80℃で3時間保持した後、室温まで冷却して下記構造の樹脂を得た。得られた樹脂の重量平均分子量は9400、分散度は1.89、酸価は114mgKOH/gであった。
B-8:下記構造の樹脂(ブロック共重合体、主鎖に付記した数値は質量比である。アミン価71mgKOH/g、重量平均分子量9000)
(dispersant)
B-1: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 24,000)
B-2: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 10,000)
B-3: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 20,000)
B-4: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 16,000)
B-5: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 20,000)
B-6: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 7000)
B-7: Resin synthesized by the following method Flow an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and add 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA). and heated to 80°C while stirring. Then, 57 parts by weight of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 A mixed solution of 54 parts by mass of a mixture of decane-9-yl acrylate (content ratio is 1:1 in molar ratio), 239 parts by mass of benzyl methacrylate , and 73 parts by mass of PGMEA was added dropwise over 5 hours. . Next, a solution of 40 parts by mass of a polymerization initiator (2,2-azobis(2,4-dimethylvaleronitrile)) dissolved in 197 parts by mass of PGMEA was added dropwise over 6 hours. After the dropwise addition of the polymerization initiator solution was completed, the temperature was maintained at 80° C. for 3 hours, and then cooled to room temperature to obtain a resin having the following structure. The weight average molecular weight of the obtained resin was 9400, the dispersity was 1.89, and the acid value was 114 mgKOH/g.
B-8: Resin with the following structure (block copolymer, the numbers appended to the main chain are mass ratios. Amine value 71 mgKOH/g, weight average molecular weight 9000)
B-1:下記構造の樹脂(主鎖に付記した数値はモル比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量24000)
還流冷却器、滴下ロートおよび撹拌機を備えたフラスコ内に窒素を適量流し、窒素雰囲気に置換し、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の340質量部を入れ、撹拌しながら80℃まで加熱した。次いで、アクリル酸の57質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレートおよび3,4-エポキシトリシクロ[5.2.1.02,6]デカン-9-イルアクリレートの混合物(含有比はモル比で1:1)の54質量部、ベンジルメタクリレートの239質量部、PGMEAの73質量部の混合溶液を5時間かけて滴下した。次いで、重合開始剤(2,2-アゾビス(2,4-ジメチルバレロニトリル))の40質量部をPGMEAの197質量部に溶解した溶液を6時間かけて滴下した。重合開始剤溶液の滴下終了後、80℃で3時間保持した後、室温まで冷却して下記構造の樹脂を得た。得られた樹脂の重量平均分子量は9400、分散度は1.89、酸価は114mgKOH/gであった。
B-1: Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 24,000)
(溶剤)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA) (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA) (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
<着色組成物の製造>
下記の表に記載の原料を混合して、着色組成物を製造した。
<Manufacture of colored composition>
A colored composition was produced by mixing the raw materials listed in the table below.
下記の表に記載の原料を混合して、着色組成物を製造した。
A colored composition was produced by mixing the raw materials listed in the table below.
上記表の略語で記載の原料は以下の通りである。
The raw materials listed with abbreviations in the table above are as follows.
(分散液)
分散液1~67、比較例分散液:上述した分散液1~67、比較例分散液 (Dispersion liquid)
Dispersions 1 to 67, comparative dispersions: Dispersions 1 to 67, comparative dispersions described above
分散液1~67、比較例分散液:上述した分散液1~67、比較例分散液 (Dispersion liquid)
Dispersions 1 to 67, comparative dispersions: Dispersions 1 to 67, comparative dispersions described above
(バインダー)
B-1:上述した分散剤B-1で示した樹脂
B-4:上述した分散剤B-4で示した樹脂
C-1:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量11000)
C-2:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量30000)
C-3:下記構造の樹脂(主鎖に付記した数値は質量比である。重量平均分子量14600)
C-4:下記構造の樹脂(主鎖に付記した数値は質量比である。重量平均分子量10600)
C-5:以下の方法で合成した樹脂
還流冷却器、滴下ロートおよび攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、1-メトキシ-2-プロピルアセテ-ト371質量部を入れ、攪拌しながら85℃まで加熱した。次いで、アクリル酸54質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8と9-イルアクリレートの混合物225質量部、ビニルトルエン(異性体混合物)81質量部、1-メトキシ-2-プロピルアセテ-ト80質量部の混合溶液を4時間かけて滴下した。一方、重合開始剤2,2-アゾビス(2,4-ジメチルバレロニトリル)30質量部を1-メトキシ-2-プロピルアセテ-ト160質量部に溶解した溶液を5時間かけて滴下した。開始剤溶液の滴下終了後、4時間85℃で保持した後、室温まで冷却して樹脂を得た。得られた樹脂の重量平均分子量は10600、分散度は2.01、酸価は43mgKOH/gであった。 (binder)
B-1: Resin shown as the above-mentioned dispersant B-1 B-4: Resin shown as the above-mentioned dispersant B-4 C-1: Resin with the following structure (the numerical value appended to the main chain is the molar ratio .Weight average molecular weight 11000)
C-2: Resin with the following structure (the numerical value appended to the main chain is the molar ratio. Weight average molecular weight 30,000)
C-3: Resin with the following structure (the numerical value appended to the main chain is the mass ratio. Weight average molecular weight 14600)
C-4: Resin with the following structure (the numerical value appended to the main chain is the mass ratio. Weight average molecular weight 10600)
C-5: Resin synthesized by the following method. Pour an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and add 371 parts by mass of 1-methoxy-2-propyl acetate. , and heated to 85° C. with stirring. Next, 54 parts by mass of acrylic acid, 225 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8 and 9-yl acrylate, and 81 parts by mass of vinyltoluene (isomer mixture). A mixed solution of 80 parts by weight of 1-methoxy-2-propyl acetate was added dropwise over 4 hours. On the other hand, a solution of 30 parts by mass of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 160 parts by mass of 1-methoxy-2-propyl acetate was added dropwise over 5 hours. After the initiator solution was added dropwise, the temperature was maintained at 85° C. for 4 hours and then cooled to room temperature to obtain a resin. The weight average molecular weight of the obtained resin was 10,600, the degree of dispersion was 2.01, and the acid value was 43 mgKOH/g.
B-1:上述した分散剤B-1で示した樹脂
B-4:上述した分散剤B-4で示した樹脂
C-1:下記構造の樹脂(主鎖に付記した数値はモル比である。重量平均分子量11000)
還流冷却器、滴下ロートおよび攪拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、1-メトキシ-2-プロピルアセテ-ト371質量部を入れ、攪拌しながら85℃まで加熱した。次いで、アクリル酸54質量部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8と9-イルアクリレートの混合物225質量部、ビニルトルエン(異性体混合物)81質量部、1-メトキシ-2-プロピルアセテ-ト80質量部の混合溶液を4時間かけて滴下した。一方、重合開始剤2,2-アゾビス(2,4-ジメチルバレロニトリル)30質量部を1-メトキシ-2-プロピルアセテ-ト160質量部に溶解した溶液を5時間かけて滴下した。開始剤溶液の滴下終了後、4時間85℃で保持した後、室温まで冷却して樹脂を得た。得られた樹脂の重量平均分子量は10600、分散度は2.01、酸価は43mgKOH/gであった。 (binder)
B-1: Resin shown as the above-mentioned dispersant B-1 B-4: Resin shown as the above-mentioned dispersant B-4 C-1: Resin with the following structure (the numerical value appended to the main chain is the molar ratio .Weight average molecular weight 11000)
(モノマー)
D-1:下記構造の化合物
D-2:下記構造の化合物の混合物(左側化合物(6官能の(メタ)アクリレート化合物)と右側化合物(5官能の(メタ)アクリレート化合物)とのモル比が7:3の混合物)
D-3:下記構造の化合物
D-4:トリメチロールプロパンエチレンオキシド変性トリアクリレート(東亞合成(株)製、アロニックスM-350)
D-5:EBECRYL80(ダイセル・オルネクス社製、アミン含有4官能アクリレート)
D-6:エトキシ化ジペンタエリスリトールヘキサメタクリレート (monomer)
D-1: Compound with the following structure
D-2: A mixture of compounds with the following structure (a mixture in which the molar ratio of the compound on the left (a hexafunctional (meth)acrylate compound) and the compound on the right (a pentafunctional (meth)acrylate compound) is 7:3)
D-3: Compound with the following structure
D-4: Trimethylolpropane ethylene oxide modified triacrylate (manufactured by Toagosei Co., Ltd., Aronix M-350)
D-5: EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
D-6: Ethoxylated dipentaerythritol hexamethacrylate
D-1:下記構造の化合物
D-5:EBECRYL80(ダイセル・オルネクス社製、アミン含有4官能アクリレート)
D-6:エトキシ化ジペンタエリスリトールヘキサメタクリレート (monomer)
D-1: Compound with the following structure
D-5: EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
D-6: Ethoxylated dipentaerythritol hexamethacrylate
(光重合開始剤)
E-1~E-4:下記構造の化合物
E-5:2,2’,4-トリス(2-クロロフェニル)-5-(3,4-ジメトキシフェニル)-4,5-ジフェニル-1,1’-ビイミダゾール
(Photopolymerization initiator)
E-1 to E-4: Compounds with the following structure E-5: 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-biimidazole
E-1~E-4:下記構造の化合物
E-5:2,2’,4-トリス(2-クロロフェニル)-5-(3,4-ジメトキシフェニル)-4,5-ジフェニル-1,1’-ビイミダゾール
E-1 to E-4: Compounds with the following structure E-5: 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-biimidazole
(界面活性剤)
F-1:KF-6001(信越化学工業(株)製、シリコーン系界面活性剤、両末端カルビノール変性ポリジメチルシロキサン、ヒドロキシ基価62mgKOH/g)
F-2:下記構造の化合物(重量平均分子量14000)。下記の式中、繰り返し単位の割合を示す%はモル%である。(フッ素系界面活性剤)
F-3:フタージェント208G(NEOS製、フッ素系界面活性剤)
F-4:BYK-330(ビックケミー社製、シリコーン系界面活性剤)
F-5:DOWSIL SH8400 FLUID(ダウ・東レ(株)製、シリコーン系界面活性剤) (surfactant)
F-1: KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxyl value 62 mgKOH/g)
F-2: Compound with the following structure (weight average molecular weight 14,000). In the formula below, % indicating the proportion of repeating units is mol%. (Fluorine surfactant)
F-3: Ftergent 208G (manufactured by NEOS, fluorine-based surfactant)
F-4: BYK-330 (manufactured by BYK Chemie, silicone surfactant)
F-5: DOWSIL SH8400 FLUID (manufactured by Dow Toray Industries, Inc., silicone surfactant)
F-1:KF-6001(信越化学工業(株)製、シリコーン系界面活性剤、両末端カルビノール変性ポリジメチルシロキサン、ヒドロキシ基価62mgKOH/g)
F-2:下記構造の化合物(重量平均分子量14000)。下記の式中、繰り返し単位の割合を示す%はモル%である。(フッ素系界面活性剤)
F-4:BYK-330(ビックケミー社製、シリコーン系界面活性剤)
F-5:DOWSIL SH8400 FLUID(ダウ・東レ(株)製、シリコーン系界面活性剤) (surfactant)
F-1: KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxyl value 62 mgKOH/g)
F-2: Compound with the following structure (weight average molecular weight 14,000). In the formula below, % indicating the proportion of repeating units is mol%. (Fluorine surfactant)
F-4: BYK-330 (manufactured by BYK Chemie, silicone surfactant)
F-5: DOWSIL SH8400 FLUID (manufactured by Dow Toray Industries, Inc., silicone surfactant)
(添加剤)
G-1:下記構造の化合物(紫外線吸収剤)
G-2:下記構造の化合物(エポキシ基を有する化合物、重量平均分子量3500)
G-3:EHPE3150((株)ダイセル製、2,2’-ビス(ヒドロキシメチル)-1-ブタノールの1,2-エポキシ-4-(2-オキシラニル)シクロヘキサン付加物)
G-4:下記構造の化合物(シランカップリング剤)
G-5:3-メタクリロキシプロピルトリメトキシシラン(KBM-503、信越化学工業(株)製、シランカップリング剤)
G-6:p-メトキシフェノール(重合禁止剤)
G-7:アデカスタブ AO-80((株)ADEKA製、酸化防止剤) (Additive)
G-1: Compound with the following structure (ultraviolet absorber)
G-2: Compound with the following structure (compound having an epoxy group, weight average molecular weight 3500)
G-3: EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2'-bis(hydroxymethyl)-1-butanol)
G-4: Compound with the following structure (silane coupling agent)
G-5: 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
G-6: p-methoxyphenol (polymerization inhibitor)
G-7: ADEKA STAB AO-80 (manufactured by ADEKA Co., Ltd., antioxidant)
G-1:下記構造の化合物(紫外線吸収剤)
G-4:下記構造の化合物(シランカップリング剤)
G-6:p-メトキシフェノール(重合禁止剤)
G-7:アデカスタブ AO-80((株)ADEKA製、酸化防止剤) (Additive)
G-1: Compound with the following structure (ultraviolet absorber)
G-4: Compound with the following structure (silane coupling agent)
G-6: p-methoxyphenol (polymerization inhibitor)
G-7: ADEKA STAB AO-80 (manufactured by ADEKA Co., Ltd., antioxidant)
(溶剤)
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
Z-2:プロピレングリコールモノメチルエーテル(PGME)
Z-3:シクロペンタノン
Z-4:シクロヘキサノン
Z-5:アニソール
Z-6:ジアセトンアルコール (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
Z-2: Propylene glycol monomethyl ether (PGME)
Z-3: Cyclopentanone Z-4: Cyclohexanone Z-5: Anisole Z-6: Diacetone alcohol
Z-1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
Z-2:プロピレングリコールモノメチルエーテル(PGME)
Z-3:シクロペンタノン
Z-4:シクロヘキサノン
Z-5:アニソール
Z-6:ジアセトンアルコール (solvent)
Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
Z-2: Propylene glycol monomethyl ether (PGME)
Z-3: Cyclopentanone Z-4: Cyclohexanone Z-5: Anisole Z-6: Diacetone alcohol
<温度サイクル試験の評価>
製造後1時間以内の各着色組成物を、下塗り層付ガラス基板上にプリベーク後の膜厚が1.0μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って膜を形成した。得られた膜を、150℃で1時間保持した後、-15℃で1時間保持するサイクルを500サイクル繰り返して温度サイクル試験を行った。温度サイクル試験後の膜について、1cm四方の部分を光学顕微鏡で観察し、0.5μm以上のサイズの結晶状の欠陥の数をカウントして評価した。
A:欠陥の数が0個
B:欠陥の数が1~4個
C:欠陥の数が5~9個
D:欠陥の数が10個以上 <Evaluation of temperature cycle test>
Each coloring composition within 1 hour after production was applied onto a glass substrate with an undercoat layer using a spin coater so that the film thickness after prebaking was 1.0 μm, and then coated on a hot plate at 100°C for 120 seconds. A film was formed by pre-baking. The obtained film was held at 150°C for 1 hour and then held at -15°C for 1 hour, which was repeated 500 times to perform a temperature cycle test. After the temperature cycle test, a 1 cm square part of the film was observed with an optical microscope, and the number of crystal defects with a size of 0.5 μm or more was counted and evaluated.
A: Number of defects is 0 B: Number of defects is 1 to 4 C: Number of defects is 5 to 9 D: Number of defects is 10 or more
製造後1時間以内の各着色組成物を、下塗り層付ガラス基板上にプリベーク後の膜厚が1.0μmになるようにスピンコーターを用いて塗布し、100℃のホットプレートを用いて120秒間プリベークを行って膜を形成した。得られた膜を、150℃で1時間保持した後、-15℃で1時間保持するサイクルを500サイクル繰り返して温度サイクル試験を行った。温度サイクル試験後の膜について、1cm四方の部分を光学顕微鏡で観察し、0.5μm以上のサイズの結晶状の欠陥の数をカウントして評価した。
A:欠陥の数が0個
B:欠陥の数が1~4個
C:欠陥の数が5~9個
D:欠陥の数が10個以上 <Evaluation of temperature cycle test>
Each coloring composition within 1 hour after production was applied onto a glass substrate with an undercoat layer using a spin coater so that the film thickness after prebaking was 1.0 μm, and then coated on a hot plate at 100°C for 120 seconds. A film was formed by pre-baking. The obtained film was held at 150°C for 1 hour and then held at -15°C for 1 hour, which was repeated 500 times to perform a temperature cycle test. After the temperature cycle test, a 1 cm square part of the film was observed with an optical microscope, and the number of crystal defects with a size of 0.5 μm or more was counted and evaluated.
A: Number of defects is 0 B: Number of defects is 1 to 4 C: Number of defects is 5 to 9 D: Number of defects is 10 or more
上記表に示すように、実施例の着色組成物は、温度サイクル試験の評価に優れていた。
実施例1において、界面活性剤を溶剤に変更しても同様の結果が得られた。
実施例の着色組成物から形成した膜は、光学フィルタ、固体撮像素子、画像表示装置に好適に使用できる。 As shown in the table above, the colored compositions of Examples were excellent in the evaluation of the temperature cycle test.
Similar results were obtained in Example 1 even when the surfactant was replaced with a solvent.
Films formed from the colored compositions of Examples can be suitably used for optical filters, solid-state imaging devices, and image display devices.
実施例1において、界面活性剤を溶剤に変更しても同様の結果が得られた。
実施例の着色組成物から形成した膜は、光学フィルタ、固体撮像素子、画像表示装置に好適に使用できる。 As shown in the table above, the colored compositions of Examples were excellent in the evaluation of the temperature cycle test.
Similar results were obtained in Example 1 even when the surfactant was replaced with a solvent.
Films formed from the colored compositions of Examples can be suitably used for optical filters, solid-state imaging devices, and image display devices.
Claims (9)
- イソインドリン顔料を含む着色剤と、式(1)で表される化合物と、樹脂と、溶剤と、を含む着色組成物;
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。 A coloring composition containing a colorant containing an isoindoline pigment, a compound represented by formula (1), a resin, and a solvent;
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring. - 前記式(1)において、R7が電子求引性基であり、X1がCR8であり、R8が酸基または塩基性基を含む、請求項1に記載の着色組成物。 The colored composition according to claim 1, wherein in the formula (1), R7 is an electron-withdrawing group, X1 is CR8 , and R8 contains an acid group or a basic group.
- 前記式(1)において、R1およびR2は、それぞれ独立してアルキル基もしくはアリール基であるか、または、R1とR2が結合して環を形成している、請求項1または2に記載の着色組成物。 2. In the formula (1), R 1 and R 2 are each independently an alkyl group or an aryl group, or R 1 and R 2 are combined to form a ring. The coloring composition described in .
- 前記着色剤は、更に、緑色顔料を含む、請求項1または2に記載の着色組成物。 The colored composition according to claim 1 or 2, wherein the coloring agent further contains a green pigment.
- 請求項1または2に記載の着色組成物から得られる膜。 A film obtained from the colored composition according to claim 1 or 2.
- 請求項5に記載の膜を有する光学フィルタ。 An optical filter comprising the film according to claim 5.
- 請求項5に記載の膜を有する固体撮像素子。 A solid-state imaging device comprising the film according to claim 5.
- 請求項5に記載の膜を有する画像表示装置。 An image display device comprising the film according to claim 5.
- 式(1)で表される化合物;
R1~R9はそれぞれ独立して、水素原子または置換基を表し、
R1~R9の少なくとも1つは酸基または塩基性基を有し、
R1~R8の2以上が結合して環を形成していてもよい。 A compound represented by formula (1);
R 1 to R 9 each independently represent a hydrogen atom or a substituent,
At least one of R 1 to R 9 has an acid group or a basic group,
Two or more of R 1 to R 8 may be combined to form a ring.
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PCT/JP2023/032326 WO2024058001A1 (en) | 2022-09-16 | 2023-09-05 | Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound |
Country Status (2)
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TW (1) | TW202413539A (en) |
WO (1) | WO2024058001A1 (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007112919A (en) * | 2005-10-21 | 2007-05-10 | Toray Ind Inc | Pigment dispersion, colorant composition and color filter |
JP2018169505A (en) * | 2017-03-30 | 2018-11-01 | 東洋インキScホールディングス株式会社 | Color filter coloring composition |
JP2019157119A (en) * | 2018-03-06 | 2019-09-19 | 住友化学株式会社 | Colorant dispersion, colored curable resin composition, color filter and display device |
JP2020160279A (en) * | 2019-03-22 | 2020-10-01 | 日本化薬株式会社 | Pigment composition |
WO2021063999A1 (en) * | 2019-09-30 | 2021-04-08 | Basf Colors & Effects Gmbh | Isoindoline derivatives |
-
2023
- 2023-09-05 WO PCT/JP2023/032326 patent/WO2024058001A1/en unknown
- 2023-09-12 TW TW112134730A patent/TW202413539A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007112919A (en) * | 2005-10-21 | 2007-05-10 | Toray Ind Inc | Pigment dispersion, colorant composition and color filter |
JP2018169505A (en) * | 2017-03-30 | 2018-11-01 | 東洋インキScホールディングス株式会社 | Color filter coloring composition |
JP2019157119A (en) * | 2018-03-06 | 2019-09-19 | 住友化学株式会社 | Colorant dispersion, colored curable resin composition, color filter and display device |
JP2020160279A (en) * | 2019-03-22 | 2020-10-01 | 日本化薬株式会社 | Pigment composition |
WO2021063999A1 (en) * | 2019-09-30 | 2021-04-08 | Basf Colors & Effects Gmbh | Isoindoline derivatives |
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TW202413539A (en) | 2024-04-01 |
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