WO2022234775A1 - 化合物 - Google Patents
化合物 Download PDFInfo
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- WO2022234775A1 WO2022234775A1 PCT/JP2022/018224 JP2022018224W WO2022234775A1 WO 2022234775 A1 WO2022234775 A1 WO 2022234775A1 JP 2022018224 W JP2022018224 W JP 2022018224W WO 2022234775 A1 WO2022234775 A1 WO 2022234775A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 300
- 125000001424 substituent group Chemical group 0.000 claims abstract description 80
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 39
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 38
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 34
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 20
- 150000001450 anions Chemical class 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 239000011347 resin Substances 0.000 claims description 79
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011342 resin composition Substances 0.000 claims description 59
- 239000003086 colorant Substances 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 239000003505 polymerization initiator Substances 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- -1 n-octyl group Chemical group 0.000 description 145
- 230000015572 biosynthetic process Effects 0.000 description 102
- 238000003786 synthesis reaction Methods 0.000 description 100
- 239000000975 dye Substances 0.000 description 84
- 239000002904 solvent Substances 0.000 description 80
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 78
- 150000002430 hydrocarbons Chemical group 0.000 description 77
- 229920006395 saturated elastomer Polymers 0.000 description 48
- 239000000126 substance Substances 0.000 description 48
- 239000007787 solid Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 32
- 239000000178 monomer Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000004949 mass spectrometry Methods 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000001816 cooling Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 20
- 239000000049 pigment Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 125000002723 alicyclic group Chemical group 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- 239000004094 surface-active agent Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 10
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 9
- 150000004292 cyclic ethers Chemical group 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 9
- 229910052721 tungsten Inorganic materials 0.000 description 9
- 239000010937 tungsten Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 150000001340 alkali metals Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 235000010724 Wisteria floribunda Nutrition 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229940116333 ethyl lactate Drugs 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001721 carbon Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000003566 oxetanyl group Chemical group 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 150000003613 toluenes Chemical class 0.000 description 4
- 238000000411 transmission spectrum Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WMUWDPLTTLJNPE-UHFFFAOYSA-N 4-bromo-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Br WMUWDPLTTLJNPE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZXXUPZWDQJEEQW-UHFFFAOYSA-N [[3-cyclohexyl-1-oxo-1-(4-phenylsulfanylphenyl)propan-2-ylidene]amino] acetate Chemical compound C(C)(=O)ON=C(C(=O)C1=CC=C(C=C1)SC1=CC=CC=C1)CC1CCCCC1 ZXXUPZWDQJEEQW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000005453 ketone based solvent Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 2
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- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 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
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 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
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- ZHHKVLCBIBQGKO-UHFFFAOYSA-H naphthol green B Chemical compound [Na+].[Na+].[Na+].[Fe+3].[O-]S(=O)(=O)C1=CC=C2C(=N[O-])C(=O)C=CC2=C1.[O-]S(=O)(=O)C1=CC=C2C(=N[O-])C(=O)C=CC2=C1.[O-]S(=O)(=O)C1=CC=C2C(=N[O-])C(=O)C=CC2=C1 ZHHKVLCBIBQGKO-UHFFFAOYSA-H 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQBDLJCYGRGAKP-UHFFFAOYSA-N olsalazine Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=C(C(O)=CC=2)C(O)=O)=C1 QQBDLJCYGRGAKP-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
-
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
Definitions
- the present invention relates to compounds, colored resin compositions, color filters and display devices.
- Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from colored resin compositions.
- Various colorants are used as the colored resin composition for forming the color filter, and examples of using compounds represented by the following formula (x1) and formula (x2) as the colorant are known. (Patent Document 1).
- an object of the present invention is to provide a compound capable of forming a color filter having excellent brightness.
- R 1 to R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
- R 5 to R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent.
- T 1 and T 2 each independently represent an optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group.
- L 1 represents an optionally substituted C 1-12 a-valent aliphatic hydrocarbon group or a group represented by formula (i), and methylene contained in the aliphatic hydrocarbon group At least one of the groups is replaced with -O-.
- a represents an integer of 2 or more.
- b and c independently represent an integer of 1 or more.
- d represents an integer of 0 or more.
- X c- represents a c-valent anion. ]
- T 3 represents an optionally substituted a-valent aromatic hydrocarbon group or an optionally substituted a-valent aromatic heterocyclic group.
- L 2 represents an optionally substituted C 1-5 divalent aliphatic hydrocarbon group, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is —O— has been replaced.
- * represents a bond with T2.
- [2] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains the compound according to [1].
- [3] The colored resin composition according to [2], further comprising a polymerizable compound and a polymerization initiator.
- [5] A display device including the color filter described in [4].
- the compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).
- compound (I) The present invention will be described in detail below using formula (I), and compound (I) also includes tautomers of formula (I).
- R 1 to R 4 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
- R 5 to R 12 each independently represent a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent.
- T 1 and T 2 each independently represent an optionally substituted divalent aromatic hydrocarbon group or an optionally substituted divalent aromatic heterocyclic group.
- L 1 represents an optionally substituted C 1-12 a-valent aliphatic hydrocarbon group or a group represented by formula (i), and methylene contained in the aliphatic hydrocarbon group At least one of the groups is replaced with -O-.
- a represents an integer of 2 or more.
- T 3 represents an optionally substituted a-valent aromatic hydrocarbon group or an optionally substituted a-valent aromatic heterocyclic group.
- L 2 represents an optionally substituted C 1-5 divalent aliphatic hydrocarbon group, and at least one of the methylene groups contained in the aliphatic hydrocarbon group is —O— has been replaced. a has the same meaning as above. * represents a bond with T2. ]
- the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 include aliphatic hydrocarbon groups and aromatic hydrocarbon groups.
- Aliphatic hydrocarbon groups may be saturated or unsaturated and may be linear or alicyclic.
- saturated or unsaturated chain hydrocarbon groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n - nonyl group, linear alkyl group such as n-decyl group; isopropyl group, (1-ethyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl) butyl group, (2 -ethyl) butyl group, (1-propyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, ( 1-propyl)pentyl group, (1
- saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cyclohexenyl groups (eg, cyclohex-2-ene , cyclohex-3-ene), cycloheptenyl group and cyclooctenyl group; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group and the like.
- cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups
- cyclohexenyl groups eg, cyclohex-2-ene , cyclohex-3-ene
- Aromatic hydrocarbon groups include aryl groups such as phenyl, 1-naphthyl and 2-naphthyl groups; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl and 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3, 5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-methyl-6-ethylphenyl group, 2,6-diethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl Alkylaryl groups such as groups, 2-methyl-6-isopropylphenyl groups, 4-butylphenyl
- the hydrocarbon group having 1 to 10 carbon atoms is a combination of two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the carbon number is 10.
- groups include, for example, aralkyl groups such as a benzyl group, a phenethyl group and a 1-methyl-1-phenylethyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); and arylalkynyl groups such as a phenylethynyl group.
- Examples of the substituent that the hydrocarbon group having 1 to 10 carbon atoms may have include a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted and at least one selected from the group consisting of an amino group, a nitro group, a cyano group, --SO 3 ⁇ , and --SO 3 M, where M represents a hydrogen atom or an alkali metal atom.
- the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- alkoxy group include alkoxy groups having 1 to 4 carbon atoms such as methoxy, ethoxy, propoxy and butoxy.
- substituted amino group include amino groups having one or two hydrocarbon groups, and examples of the hydrocarbon group include the groups exemplified above as the hydrocarbon groups having 1 to 10 carbon atoms.
- substituted amino groups include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N- An ethylphenylamino group and the like can be mentioned.
- alkali metal atoms examples include sodium and potassium.
- Halogen atoms represented by R 5 to R 12 include fluorine, chlorine, bromine and iodine atoms.
- Examples of the hydrocarbon groups having 1 to 5 carbon atoms represented by R 5 to R 12 include aliphatic hydrocarbon groups having 1 to 5 carbon atoms.
- groups having 1 to 5 carbon atoms can be mentioned.
- Examples of the substituent that the hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as the substituent A.
- the divalent aromatic hydrocarbon group represented by T 1 and T 2 is a group in which two hydrogen atoms directly bonded to carbon atoms constituting the ring are substituted for bonds in an aromatic hydrocarbon ring.
- the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group may be either a monocyclic ring or a condensed ring, for example, a benzene ring, a naphthalene ring, an anthracene ring, and at least one structure in which one hydrogen atom is replaced with a hydrocarbon group.
- hydrocarbon group examples include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 described above, preferably saturated chain hydrocarbon groups, aryl groups, or an alkylaryl group, more preferably a saturated chain hydrocarbon group having 1 to 4 carbon atoms.
- the number of hydrocarbon groups bonded to the aromatic hydrocarbon ring is preferably 0-4, more preferably 0-3.
- divalent aromatic hydrocarbon group include groups represented by the following formulas (Ta-1) to (Ta-8).
- the bivalent aromatic heterocyclic group represented by T 1 and T 2 is a group in which two hydrogen atoms directly bonded to ring-constituting atoms in an aromatic heterocyclic ring are replaced with bonds.
- the aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group may be either a monocyclic ring or a condensed ring, such as pyrrole ring, oxazole ring, pyrazole ring, imidazole ring, thiazole ring, furan ring, thiophene ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, indole ring, benzimidazole ring, benzothiazole ring, quinoline ring, benzofuran ring, and structures in which at least one hydrogen atom of these aromatic heterocycles is replaced with a hydrocarbon group etc.
- hydrocarbon group examples include the groups exemplified as the hydrocarbon groups having 1 to 10 carbon atoms represented by R 1 to R 4 and R 13 described above, preferably saturated chain hydrocarbon groups, aryl groups, or an alkylaryl group.
- the number of hydrocarbon groups bonded to the aromatic heterocycle is preferably 0-4, more preferably 0-3.
- Examples of the substituent that the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group may have include the groups exemplified as the substituent A.
- the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by L 1 is a group in which a hydrogen atoms constituting an aliphatic hydrocarbon are replaced with bonds. The a bonds are preferably present on different carbon atoms.
- the a-valent aliphatic hydrocarbon group includes an a-valent chain hydrocarbon group, an a-valent alicyclic hydrocarbon group, and an a-valent group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group. etc.
- the a-valent chain hydrocarbon group may be saturated or unsaturated, but is preferably an a-valent saturated chain hydrocarbon group.
- a-valent saturated chain hydrocarbon groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5 -alkanediyl groups such as diyl group and hexane-1,6-diyl group; alkanetriyl groups such as groups represented by formulas (a-1) to (a-2) below; formula (a-3) below An alkanetetrayl group such as a group represented by;
- the a-valent chain hydrocarbon group preferably has 1 to 8 carbon atoms, more preferably 2 to 6 carbon atoms.
- the a-valent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably an a-valent saturated alicyclic hydrocarbon group.
- the a-valent saturated alicyclic hydrocarbon group includes divalent saturated alicyclic hydrocarbons such as cyclohexyl-1,2-diyl group, cyclohexyl-1,4-diyl group and norbornane-2,5-diyl group. group; trivalent saturated alicyclic hydrocarbon group such as cyclohexyl-1,3,5-triyl group; tetravalent saturated alicyclic hydrocarbon group such as cyclohexyl-1,2,4,5-tetrayl group; etc.
- the a-valent alicyclic hydrocarbon group preferably has 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms.
- Examples of the a-valent group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group include groups represented by the following formulas (a-5) to (a-7).
- At least one methylene group contained in the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms represented by L 1 is replaced with —O—.
- both adjacent methylene groups are not replaced with -O-.
- the number of methylene groups substituted for -O- is, for example, 1 to 6, preferably 1 or more and a or less, more preferably a.
- the position of the methylene group to be replaced with -O- is not particularly limited, but at least one of the methylene groups adjacent to the bond possessed by the a-valent aliphatic hydrocarbon group is preferably replaced with -O-, and the a-valent aliphatic It is more preferable that all the methylene groups adjacent to the bond of the group hydrocarbon group are replaced with -O-.
- Examples of the group in which at least one of the methylene groups contained in the a-valent aliphatic hydrocarbon group is replaced with -O- include groups represented by the following formulas (l-1a) to (l-24a). is preferably a group represented by formula (l-1a) ⁇ (l-16a), (l-18a) ⁇ (l-19a), (l-22a) ⁇ (l-24a), formula (l- 1a), (l-10a) to (l-16a), (l-18a) to (l-19a), and (l-22a) to (l-24a) are more preferred, and the groups represented by formula (l Groups represented by -10a) to (l-16a) are more preferred.
- Examples of the substituent that the a-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms may have include the groups exemplified as the substituent A.
- L 1 may be a group represented by formula (i).
- the a-valent aromatic hydrocarbon group represented by T 3 is an aromatic hydrocarbon ring in which a hydrogen atoms directly bonded to carbon atoms constituting the ring are replaced with bonds. It is a base.
- the aromatic hydrocarbon ring constituting the a-valent aromatic hydrocarbon group include the structures explained as the aromatic hydrocarbon ring constituting the above-mentioned divalent aromatic hydrocarbon group.
- the a-valent aromatic heterocyclic group represented by T 3 is an aromatic heterocyclic group in which a hydrogen atoms directly bonded to atoms constituting the ring are replaced with bonds. is.
- the aromatic heterocyclic ring that constitutes the a-valent aromatic heterocyclic group include the structures described as the aromatic heterocyclic ring that constitutes the above-mentioned divalent aromatic heterocyclic group.
- Examples of the substituent that the a-valent aromatic hydrocarbon group and the a-valent aromatic heterocyclic group may have include the groups exemplified as the substituent A.
- the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by L 2 includes a divalent chain hydrocarbon group having 1 to 5 carbon atoms, a chain hydrocarbon group having 1 to 5 carbon atoms, Divalent alicyclic hydrocarbon groups are mentioned.
- the divalent chain hydrocarbon group may be saturated or unsaturated, but is preferably a bivalent saturated chain hydrocarbon group.
- Divalent saturated chain hydrocarbon groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5 alkanediyl groups such as -diyl group.
- the divalent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group.
- divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl group and cyclobutyl-1,3-diyl group.
- At least one methylene group contained in the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by L 2 is replaced with —O—.
- both adjacent methylene groups are not replaced with -O-.
- the number of methylene groups substituted for -O- is, for example, 1-3, preferably 1-2.
- the position of the methylene group to be replaced with -O- is not particularly limited, but the methylene group adjacent to the bond with T2 is preferably replaced with -O-.
- Examples of the substituent that the divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have include the groups exemplified as the substituent A.
- formula (i) examples include groups represented by the following formulas (i1) to (i8).
- L i1 to L i8 each independently represent an alkanediyl group having 1 to 5 carbon atoms, and one of the methylene groups contained in the alkanediyl group is -O-. has been replaced. * represents a bond with T2.
- the position of the methylene group to be replaced with -O- is not particularly limited, but the methylene group adjacent to the bond with T2 is preferably replaced with -O-.
- a plurality of L i1 to L i8 may be the same or different, but are preferably the same.
- the c-valent anion represented by X c- includes known anions, specifically, fluoride ion, chloride ion, bromide ion, halide ion such as iodide ion, boron-containing anion, Examples include aluminum-containing anions, fluorine-containing anions, and anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements.
- Examples of boron-containing anions and aluminum-containing anions include anions represented by the following formula (4).
- W 1 and W 2 each independently represent a group having two substituents formed by releasing protons from a monovalent proton-donating substituent.
- M represents boron or aluminum.
- the group having two substituents formed by releasing protons from a monovalent proton-donating substituent includes compounds having at least two monovalent proton-donating substituents (e.g., hydroxy group, carboxylic acid group, etc.). groups in which protons are released from each of two proton-donating substituents.
- Examples of the compound include catechol optionally having substituents, 2,3-dihydroxynaphthalene optionally having substituents, 2,2'-biphenol optionally having substituents, substituents 3-hydroxy-2-naphthoic acid optionally having a substituent, 2-hydroxy-1-naphthoic acid optionally having a substituent, 1-hydroxy-2-naphthoic acid optionally having a substituent Acid, binaphthol optionally having substituents, salicylic acid optionally having substituents, benzilic acid optionally having substituents or mandelic acid optionally having substituents is preferred.
- substituents include saturated hydrocarbon groups (eg, alkyl groups, cycloalkyl groups, etc.), halogen atoms, haloalkyl groups, hydroxy groups, amino groups, nitro groups, alkoxy groups, and the like.
- Salicylic acids which may have a substituent include salicylic acid, 3-methylsalicylic acid, 3-tert-butylsalicylic acid, 3-methoxysalicylic acid, 3-nitrosalicylic acid, 4-trifluoromethylsalicylic acid, 3,5-di- Monoaminosalicylic acids such as tert-butylsalicylic acid, 3-aminosalicylic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid; 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2 monohydroxysalicylic acids such as 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid); 4,5-dihydroxysalicylic acid, 4, dihydroxysalicylic acid such as 6-dihydroxysalicylic acid; monohalosalicylic acid; dihalosalicylic acid such as 3,5-dich
- Preferred anions among the anions represented by formula (4) include anions represented by the following formulas, anions (BC-1) to anions (BC-24) having substituents listed in the table, and , anions (BC-25) to (BC-28) represented by formulas (BC-25), (BC-26), (BC-27) and (BC-28), respectively.
- the anions represented by formula (4) include anion (BC-1), anion (BC-2), anion (BC-3), anion (BC-25), Anion (BC-26), anion (BC-27) are preferred, anion (BC-1), anion (BC-2), anion (BC-25) are more preferred, anion (BC-1), anion (BC -2) is more preferred.
- fluorine-containing anions examples include groups represented by the following formulas (6), (7), (8), and (9).
- W 3 and W 4 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 and W 4 together represents a fluorinated alkanediyl group of ⁇ 4.
- W 5 to W 7 each independently represent a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms.
- Y 1 represents an alkanediyl fluoride group having 1 to 4 carbon atoms.
- Y 2 represents a fluorinated alkyl group having 1 to 4 carbon atoms.
- a perfluoroalkyl group is preferable as the fluorinated alkyl group having 1 to 4 carbon atoms.
- the perfluoroalkyl groups include -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -CF 2 CF(CF 3 ) 2 , -C(CF 3 ) 3 and the like.
- a perfluoroalkanediyl group is preferable as the alkanediyl fluoride group having 1 to 4 carbon atoms.
- the perfluoroalkanediyl groups include -CF 2 -, -CF 2 CF 2 -, -CF 2 CF 2 CF 2 -, -C(CF 3 ) 2 -, -CF 2 CF 2 CF 2 CF 2 -, and the like. mentioned.
- anion represented by formula (6) includes anions represented by formulas (6-1) to (6-6) (hereinafter, “anion (6 -1)” to “anion (6-6)”).
- anion (7) examples include anion (7-1) represented by the following formula.
- anion represented by formula (8) includes anions represented by formulas (8-1) to (8-4) (hereinafter “anion (8- 1)” to “anion (8-4)”).
- anion represented by formula (9) includes anions represented by formulas (9-1) to (9-4) (hereinafter “anion (9- 1)” to “anion (9-4)”).
- the c-valent anion represented by X c- is at least one anion (that is, a fluorine-containing anion) selected from the group consisting of anion (6), anion (7), anion (8) and anion (9).
- anion (6-1), the anion (6-2) and the anion (7-1) are preferred, and the anion (6-2) is particularly preferred.
- Examples of c-valent anions represented by X c- include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, and oxygen as essential elements, and tungsten as an essential element.
- Anions of contained heteropolyacids or isopolyacids are preferred, and anions of phosphotungstic acids, silicotungstic acids and tungsten isopolyacids are more preferred.
- Examples of such anions of heteropolyacids or isopolyacids containing tungsten as an essential element include Keggin-type phosphotungstate ion ⁇ -[PW 12 O 40 ] 3 ⁇ and Dawson-type phosphotungstate ion ⁇ -[P 2 .
- anions other than the anions of heteropolyacids or isopolyacids containing tungsten as an essential element anions consisting of at least one element selected from the group consisting of silicon and phosphorus and oxygen are preferred.
- Such anions composed of oxygen and at least one element selected from the group consisting of silicon and phosphorus include SiO 3 2- and PO 4 3- .
- heteropolyanions such as Keggin-type phosphotungstate ions, Dawson-type phosphotungstate ions, and Keggin-type silicotungstate ions, and isopolyanions such as [W 10 O 32 ] 4- are preferred because of their ease of synthesis and post-treatment. preferable.
- a plurality of R 1 to R 13 , T 1 , T 2 and L 1 may be the same or different, but are preferably the same.
- a plurality of L 2 may be the same or different, but are preferably the same.
- R 1 to R 4 are each independently an optionally substituted saturated chain hydrocarbon group having 1 to 10 carbon atoms, an optionally substituted aryl having 6 to 10 carbon atoms or an optionally substituted alkylaryl group having 7 to 10 carbon atoms.
- R 1 and R 3 are each independently an optionally substituted C 6-10 aryl group or an optionally substituted C 7-10 alkylaryl and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, preferably R 1 and R 3 are each independently an optionally substituted phenyl group, and R 2 and R 4 are each independently an optionally substituted carbon It is more preferably a saturated chain hydrocarbon group of number 1 to 10, R 1 and R 3 are each independently a phenyl group that may have a substituent, and at least one of the two bonding positions ortho to the N bonded to the phenyl group is a group having an alkyl group having 1 to 4 carbon atoms, and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent; It is even more preferable to have R 1 and R 3 are each independently a phenyl group that may have a substituent, and at least one of
- a group having up to 3 alkyl groups, and R 2 and R 4 are each independently a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may have a substituent.
- the substituents that the phenyl group may have include an alkyl group having 1 to 4 carbon atoms, a halogen atom, a hydroxy group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, at least one or more selected from the group consisting of cyano group, —SO 3 ⁇ , and —SO 3 M (where M is the same as above), among which alkyl groups having 1 to 4 carbon atoms, halogen atoms, and alkoxy groups; , and --SO 3 -- , and at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and --SO 3 -- . More than one is preferred.
- the brightness of the resulting color filter can be further enhanced.
- the substitution position of the alkoxy group (preferably methoxy group) is not particularly limited, but the effect can be further enhanced by bonding to the position para to N bonded to the phenyl group.
- each of R 1 and R 3 independently represents any one of the groups represented by formulas (r1) to (r3).
- One or more hydrogen atoms of the groups represented by formulas (r1) to (r3) may be substituted with --SO 3 -- .
- R r1 to R r4 each independently represent an alkyl group having 1 to 4 carbon atoms. * indicates a bond.
- R r1 to R r4 are preferably methyl groups.
- R 5 to R 12 are preferably hydrogen atoms.
- R 13 is preferably a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an optionally substituted carbon atom of 1 to 6 saturated chain hydrocarbon groups, more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group or an isopropyl group.
- T 1 is preferably a divalent aromatic hydrocarbon group which may have a substituent, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group includes a benzene ring, A naphthalene ring or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) is preferred.
- T 1 is more preferably any one of the groups represented by the above formulas (Ta-1) to (Ta-8), and particularly preferably the group represented by the above formula (Ta-8).
- T 2 is preferably a divalent aromatic hydrocarbon group which may have a substituent
- the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group includes a benzene ring, A naphthalene ring or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4) is preferable, and a benzene ring or a benzene ring has A structure in which at least one hydrogen atom is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms is more preferable.
- T 2 is more preferably any one of the groups represented by the following formulas (Tb-1) to (Tb-10), and the following formulas (Tb-3), (Tb-5), (Tb- 6), (Tb-9), and (Tb-10), more preferably any one of the groups represented by the following formulas (Tb-5), (Tb-6), (Tb-9), Any group represented by (Tb-10) is particularly preferred.
- T 3 is an a-valent aromatic hydrocarbon group which may have a substituent
- L 2 is a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms. is preferably a group in which at least one of the methylene groups contained in the saturated chain hydrocarbon group is replaced with -O-, and more preferably any of the groups represented by the above formulas (i1) to (i8), A group represented by the above formula (i2) or formula (i3) is more preferable, and any one of the groups represented by the following formulas (i-1) to (i-6) is particularly preferable.
- L 1 is an optionally substituted C 1-8 a-valent aliphatic hydrocarbon group, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is —O— or is preferably any of the groups represented by the above formulas (i1) to (i8), optionally substituted a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced with -O- is more preferably a group, or a group represented by the above formula (i2) or formula (i3), optionally substituted a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced with -O- or any one of the groups represented by the above formulas (i-1) to (i-6), Any one of the groups represented by the above formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6) is particularly preferred.
- the c-valent anion represented by X c- is a halide ion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements. is preferably a halide ion, or an anion of a heteropolyacid or isopolyacid containing tungsten as an essential element, more preferably a halide ion, a Keggin-type phosphotungstate ion, or a Dawson-type phosphotungstate ion .
- the substituent (ie, substituent A) possessed by compound (I) is selected from the group consisting of a halogen atom, a hydroxy group, an alkoxy group, a substituted or unsubstituted amino group, —SO 3 ⁇ , and —SO 3 M. and more preferably at least one selected from the group consisting of a halogen atom, an alkoxy group, —SO 3 ⁇ , and —SO 3 M.
- a is preferably an integer of 2 or more and 6 or less, more preferably an integer of 2 or more and 4 or less, and still more preferably 2 or 3.
- c is usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.
- e is an integer of 0 or more, preferably 0 or more and (a+1) or less, more preferably 0 or more and a or less, still more preferably 0 or a.
- d is 1 or more
- X c- is an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen as essential elements, and d is 1 above and e is 0 is preferred.
- Compound (I) is preferably a compound represented by formula (I-1) or formula (I-2).
- R 101 and R 103 are each independently an optionally substituted phenyl group
- R 102 and R 104 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent
- R 105 to R 112 are hydrogen atoms
- R 113 is a hydrogen atom or an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms
- T 101 and T 102 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, A naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms
- L 101 is an optionally substituted a101-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms, wherein at least one methylene group contained in the aliphatic hydrocarbon group is —O— or in the group represented by formula (i), T 3
- R 201 and R 203 are each independently a phenyl group which may have a substituent;
- R 202 and R 204 are each independently a saturated chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent;
- R 205 to R 212 are hydrogen atoms,
- R 213 is a hydrogen atom or an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms,
- T 201 and T 202 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring, A naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms,
- L 201 is an optionally substituted C 1-8 a20 monovalent saturated chain hydrocarbon group, wherein at least one of the methylene groups contained in the aliphatic hydrocarbon group is —O— or in the group represented
- substituents that the phenyl group represented by R 101 , R 103 , R 201 and R 203 may have include alkyl groups having 1 to 4 carbon atoms, halogen atoms, hydroxy groups, alkoxy groups, formyl groups, at least one or more selected from the group consisting of substituted or unsubstituted amino group, nitro group, cyano group, and —SO 3 M (M is a hydrogen atom or an alkali metal atom); is preferably at least one selected from the group consisting of an alkyl group and an alkoxy group having 1 to 4 carbon atoms.
- the halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for the substituent A.
- R 101 , R 103 , R 201 and R 203 are optionally substituted phenyl groups, at least one of the two bonding positions ortho to the N bonded to the phenyl group; A group having an alkyl group having 1 to 4 carbon atoms on (preferably both) is preferred.
- R 101 , R 103 , R 201 and R 203 are each independently preferably any of the groups represented by the above formulas (r1) to (r3).
- R 102 , R 104 , R 202 and R 204 are preferably an optionally substituted saturated chain hydrocarbon group having 1 to 6 carbon atoms, and a saturated chain hydrocarbon group having 2 to 6 carbon atoms.
- a hydrogen group is more preferred.
- Substituents that the saturated chain hydrocarbon groups represented by R 102 , R 104 , R 202 and R 204 may have include halogen atoms, hydroxy groups, alkoxy groups, formyl group, substituted or unsubstituted amino group, nitro group, cyano group, and --SO 3 M (M is a hydrogen atom or an alkali metal atom).
- the halogen atom, alkoxy group, substituted amino group, and alkali metal atom are the same as those described for the substituent A.
- Examples of the substituent which the saturated chain hydrocarbon group having 1 to 6 carbon atoms represented by R 113 and R 213 may have include the groups described as the substituent B.
- T 101 and T 201 examples of the substituent that the divalent aromatic hydrocarbon group represented by T 101 and T 201 may have include the groups described as the substituent B.
- T 101 and T 201 are preferably any of the groups represented by the above formulas (Ta-1) to (Ta-8), and are preferably groups represented by the formula (Ta-8). more preferred.
- substituents that the divalent aromatic hydrocarbon group represented by T 102 and T 202 may have include the groups described as the substituent B, among which a group consisting of a halogen atom and an alkoxy group. At least one or more selected from is preferable.
- T 102 and T 202 are optionally substituted divalent aromatic hydrocarbon groups, wherein the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group is a benzene ring Or it is preferably a structure in which at least one hydrogen atom of the benzene ring is replaced with a saturated chain hydrocarbon group having 1 to 4 carbon atoms, represented by the above formulas (Tb-1) to (Tb-10) Any of the groups is more preferred, and any of the groups represented by the formulas (Tb-5), (Tb-6), (Tb-9) and (Tb-10) is particularly preferred.
- an a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms represented by L 101 and L 201 an a-valent aromatic group represented by T 3
- Examples of the substituent that the hydrocarbon group and L 2 in the formula (i) may have include the groups described as the substituent B.
- L 101 and L 201 are optionally substituted a-valent saturated chain hydrocarbon groups having 1 to 8 carbon atoms and at least one methylene group contained in the aliphatic hydrocarbon group.
- one is a group substituted with -O-, or any of the groups represented by the above formulas (i1) to (i8), optionally substituted a-valent saturated chain hydrocarbon group having 1 to 8 carbon atoms, wherein at least one methylene group contained in the aliphatic hydrocarbon group is replaced with -O- is more preferably a group, or a group represented by the above formula (i2) or formula (i3), Any one of the groups represented by the above formulas (l-10a) to (l-16a) or formulas (i-1) to (i-6) is particularly preferred.
- a201 and e201 are preferably the same.
- the compounds represented by formulas (I-1) and (I-2) preferably have zero charge.
- the compound represented by formula (I-1) is preferable.
- Examples of compound (I) include compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I- 108a-2), and compounds (I-1b) to (I-108b) represented by the following formula (Ib).
- the compound represented by formula (Ib) is a compound in which b is 1 and d is 0 among compounds (I).
- any e2 hydrogen atoms of R 1b to R 13b , T 1b , T 2b and L 1b are substituted with —SO 3 — .
- H is a hydrogen atom
- Et is an ethyl group
- Pr is an n-propyl group
- r-1 to r-3 are represented by the following formulas (r-1) to (r-3).
- Ta-8 represents a group represented by the following formula (Ta-8)
- Tb-5 to Tb-6 and Tb-9 to Tb-10 are represented by the following formulas (Tb-5) to (Tb- 6) and groups represented by (Tb-9) to (Tb-10)
- i-1 and i-4 represent groups represented by the following formulas (i-1) and (i-4)
- l-13a represents a group represented by the following formula (l-13a).
- compounds (I-1a-1) to (I-108a-1) and compounds (I-1a-2) to (I-108a-2) are preferred, and compound (I-1a- 2) to (I-108a-2) are more preferred, compounds (I-1a-2) to (I-36a-2), compound (I-39a-2), compound (I-42a-2), compound (I-45a-2), compound (I-48a-2), compound (I-51a-2) and compound (I-54a-2) are more preferred.
- Compound (I) can be produced, for example, by the following methods (1) to (3).
- Compound (I') is represented by, for example, formula (BI) can be produced by reacting a compound represented by Formula (C-I) with a compound represented by Formula (C-I).
- T 1B represents a group in which a bond different from the bond bonding to the nitrogen atom in T 1 is replaced with a hydrogen atom.
- the amount of the compound represented by formula (C-I) to be used is preferably 0.5 mol or more and 10 mol or less, more preferably 1 mol, per 1 mol of the compound represented by formula (BI). It is mol or more and 4 mol or less.
- the reaction temperature is preferably 30°C to 180°C, more preferably 80°C to 130°C.
- the reaction time is preferably 1 hour to 12 hours, more preferably 1 hour to 8 hours.
- the above reaction may be carried out in the presence of an organic solvent or in the absence of a solvent, but from the standpoint of yield, it is preferably carried out in an organic solvent.
- organic solvents include hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene and chloroform; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as ketones; amide solvents such as 1-methyl-2-pyrrolidone;
- the amount of the organic solvent used is preferably 1 part by mass or more and 20 parts by mass or less, more preferably 2 parts by mass or more and 10 parts by mass or less, relative to 1 part by mass of the compound represented by formula (BI). be.
- Condensing agents include phosphoric acid, polyphosphoric acid, phosphorus oxyhalides such as phosphorus oxychloride, sulfuric acid, and thionyl halides such as thionyl chloride.
- phosphorus oxyhalide, thionyl halide, or the like is used as a condensing agent and the relationship of formula (z1) is satisfied, compound (I′) in which X c ⁇ is a halide ion can be obtained.
- a ⁇ be>0 (z1) [In the above formula, a and b have the same meanings as a and b in formula (I).
- the amount of the condensing agent used is preferably 0.1 parts by mass or more and 20 parts by mass or less, more preferably 0.2 parts by mass or more and 10 parts by mass with respect to 1 part by mass of the compound represented by formula (BI). Part by mass or less.
- the method for obtaining compound (I') from the reaction mixture is not particularly limited, and various known techniques can be employed. After taking out, the resulting residue may be purified by column chromatography, recrystallization, or the like.
- compound (I) (hereinafter sometimes referred to as compound (I'')) wherein X c- is an anion other than a halide ion (hereinafter, anion X 1 )
- compound (I'') can be produced by mixing compound (I′) with an alkali metal salt or protonic acid of anion X 1 .
- Alkali metals include lithium, sodium and potassium.
- the amount of the alkali metal salt or protonic acid of the anion X1 to the compound ( I ') is preferably added in a stoichiometric ratio such that the cation in the compound ( I ') and the charge of the anion X1 are balanced.
- it is preferably 0.5 mol or more and 8 mol or less, more preferably 1 mol or more and 3 mol or less, relative to 1 mol of (I').
- the compound ( I ') and an alkali metal salt or protonic acid of anion X1 may be mixed either by dissolving them in the following solvent or without dissolving them.
- Solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water and chloroform. be done.
- the amount of the solvent to be used is preferably 1 part by mass or more and 30 parts by mass or less, more preferably 2 parts by mass or more and 20 parts by mass or less, relative to 1 part by mass of compound (I').
- an acid such as acetic acid or hydrochloric acid may be added.
- the temperature for mixing compound ( I ') and an alkali metal salt or protonic acid of anion X1 is preferably 0°C to 150°C, more preferably 10°C to 120°C, still more preferably 20°C to 100°C.
- the mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, even more preferably 3 hours to 12 hours.
- compound (I'') can be obtained by mixing the solutions, optionally stirring for 1 to 3 hours, and then removing the solvent. . If necessary, the obtained compound (I'') may be washed with ion-exchanged water, methanol, or the like.
- the reaction mixture is mixed with ion-exchanged water, stirred for 1 to 3 hours if necessary, and then the organic layer is obtained by liquid separation to obtain the compound ( I'') can be obtained. If necessary, the solution may be washed with deionized water.
- Compound (I'') can be obtained by removing the solvent from a solution containing compound (I'').
- the amount of sulfuric acid used relative to compound (I') should be such that the cation in compound (I') and the charge of --SO 3 -- are balanced. is, for example, 0.5 mol or more and 8 mol or less, preferably 1 mol or more and 3 mol or less.
- the sulfuric acid may be used as a reaction solvent, and when sulfuric acid is used as a solvent, the amount of sulfuric acid used is, for example, 20 mol or more, preferably 25 mol or more, relative to 1 mol of compound (I'). be.
- the upper limit of the amount of sulfuric acid to be used is not particularly limited.
- the mixing temperature of compound (I') and sulfuric acid is preferably 0°C to 150°C, more preferably 10°C to 120°C, even more preferably 20°C to 100°C.
- the mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 24 hours, even more preferably 3 hours to 12 hours.
- a mixture obtained by mixing compound (I') and sulfuric acid can be added to ice water to form a suspension, and then filtered to obtain compound (I'''). Further, if necessary, it may be further purified by a known technique such as recrystallization or fractionation by chromatography.
- the colored resin composition of the present invention contains a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)), and the coloring agent is a compound Including (I).
- the colored resin composition of the present invention further contains a polymerizable compound (hereinafter sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D).) is preferred.
- the colored resin composition of the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)).
- the colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)).
- the compounds exemplified as each component can be used singly or in combination unless otherwise specified.
- Colorant (A) contains compound (I).
- the brightness of the color filter to be obtained is improved, and preferably the thickness of the color filter to be obtained can be reduced.
- the heat resistance and/or solvent resistance of the obtained color filter is preferably improved.
- the compound (I) include the compound (I) described above, and preferred embodiments thereof are also the same.
- the coloring agent (A) contains a dye other than compound (I) (hereinafter sometimes referred to as dye (A1-1)) and/or a pigment (hereinafter sometimes referred to as pigment (A1-2)). good too.
- dye (A1-1) a dye other than compound (I)
- pigment (A1-2) a pigment
- colorant (A1) the combination of dye (A1-1) and pigment (A1-2) may be referred to as colorant (A1). These may be used alone or in combination of two or more.
- the dye (A1-1) is not particularly limited as long as it does not include the compound (I), and known dyes can be used. Examples include solvent dyes, acid dyes, direct dyes, mordant dyes, and the like. Dyes include, for example, compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dye Note (Shikisensha).
- azo dyes cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinolines Dyes, nitro dyes, phthalocyanine dyes, and the like.
- organic solvent-soluble dyes are preferred.
- Solvent Orange 2 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C. I. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C. I. solvent blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; I. solvent dyes, C. I.
- the pigment (A1-2) is not particularly limited as long as it does not include the compound (I), and known pigments can be used.
- pigments. Pigments classified as pigments include, for example, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231; C. I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I.
- C. I. Blue pigments such as Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
- C. I. Violet color pigments such as Pigment Violet 1, 19, 23, 32, 36, 38;
- Green pigments such as Pigment Green 7, 36, 58, 59, 62, 63;
- C. I. Brown pigments such as Pigment Brown 23 and 25;
- C. I. black pigments such as Pigment Black 1 and 7;
- the coloring agent (A1) is preferably a yellow, red or green dye and/or pigment.
- the coloring agent (A1) may be subjected, if necessary, to rosin treatment, surface treatment using a derivative into which an acidic group or a basic group is introduced, or the like, graft treatment to the surface of the coloring agent (A1) with a polymer compound or the like, sulfuric acid Atomization treatment by an atomization method or the like, washing treatment with an organic solvent, water, or the like for removing impurities, removal treatment by an ion exchange method or the like for ionic impurities, or the like may be performed.
- the particle size of the colorant (A1) is preferably substantially uniform.
- the content of the compound (I) is, for example, 1% by mass or more, preferably 2% by mass, relative to the total amount of the colorant (A). or more, more preferably 10% by mass or more, still more preferably 25% by mass or more, and particularly preferably 50% by mass or more.
- the content of the compound (I) is, for example, less than 100% by mass with respect to the total amount of the colorant (A).
- the colored resin composition contains the solvent (E)
- the colored resin composition is prepared using the colorant-containing liquid. may be prepared.
- the colorant (A) does not dissolve in the solvent (E)
- the colorant-containing liquid contains the colorant (A) and the solvent (E ) can be prepared by dispersing and mixing.
- the colorant-containing liquid may contain part or all of the solvent (E) contained in the colored resin composition.
- the content of solids in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass, relative to the total amount of the colorant-containing liquid. % by mass or less, more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less.
- the coloring agent (A) may be dispersed uniformly in the solution by incorporating a dispersing agent and performing a dispersion treatment.
- a dispersing agent When two or more types are used in combination as the colorant (A), each of them may be subjected to dispersion treatment alone, or a plurality of types may be mixed and subjected to dispersion treatment.
- Dispersants include, for example, surfactants, and may be cationic, anionic, nonionic or amphoteric surfactants. Specific examples include surfactants such as polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more.
- KP manufactured by Shin-Etsu Chemical Co., Ltd.
- Floren manufactured by Kyoeisha Chemical Co., Ltd.
- Solsperse registered trademark
- EFKA registered trademark
- a resin (B) described later may be used as a dispersant.
- the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10000 parts by mass or less, preferably 5 parts by mass or more and 5000 parts by mass, relative to 100 parts by mass of the colorant (A). parts by mass or less, more preferably 10 parts by mass or more and 1000 parts by mass or less, and still more preferably 15 parts by mass or more and 800 parts by mass or less.
- the amount of the dispersant used is within the above range, there is a tendency to obtain a colorant-containing liquid in a more uniformly dispersed state.
- the content of the coloring agent (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass, based on the total solid content of the colored resin composition. or less, more preferably 1% by mass or more and 30% by mass or less.
- the content of the coloring agent (A) is within the above range, the color density of the color filter is sufficient, and the necessary amount of the resin (B) can be contained in the composition. It is preferable because a pattern with sufficient strength can be formed.
- the "total amount of solid content” in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition.
- the total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.
- Resin [K1] a structural unit derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)”); , a copolymer having structural units derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)”); Resin [K2]; a structural unit derived from (a), a structural unit derived from (b), and a monomer (c) copolymerizable with (a) (where (a) and (b) are different.) (hereinafter sometimes referred to as "(c)”) and
- Examples of monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o-, m-, p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicy
- the monomer (b) has a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond.
- a polymerizable compound having Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
- the monomer (b) for example, a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b2)”), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter referred to as "monomer (b3)” in some cases), etc.
- the monomer (b1) for example, a monomer having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter sometimes referred to as "monomer (b1-1)"), unsaturated alicyclic Examples thereof include monomers having a structure obtained by epoxidizing a hydrocarbon of the formula (hereinafter sometimes referred to as “monomer (b1-2)").
- the monomer (b1-1) a monomer having a glycidyl group and an ethylenically unsaturated bond is preferred.
- Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, ⁇ -ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3 -bis(glycidyloxymethyl)styrene, 2,4-bis
- Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), and 3,4-epoxycyclohexylmethyl.
- (Meth)acrylate eg, Cychromer (registered trademark) A400; manufactured by Daicel Corporation
- 3,4-epoxycyclohexylmethyl (meth)acrylate eg, Cychromer (registered trademark) M100; manufactured by Daicel Corporation
- a compound represented by the formula (BI) a compound represented by the formula (BII), and the like.
- R a and R b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. may be substituted with X a and X b each independently represent a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH-.
- R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond with O.
- alkyl groups having 1 to 4 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.
- Alkyl groups in which a hydrogen atom is substituted with hydroxy include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1 -hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
- R a and R b preferably include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, more preferably a hydrogen atom and a methyl group.
- alkanediyl groups include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, A hexane-1,6-diyl group and the like can be mentioned.
- X a and X b are preferably a single bond, a methylene group, an ethylene group, a *—CH 2 —O— (* represents a bond with O) group, or a *—CH 2 CH 2 —O— group. more preferably a single bond or *--CH 2 CH 2 --O-- group (* represents a bond with O).
- Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among them, formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15) Compounds represented by Formula (BI-1), Formula (BI-7), Formula (BI-9) and Formula (BI-15) are more preferable.
- Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), and among them, formula (BII-1), formula (BII -3), formula (BII-5), formula (BII-7), formula (BII-9) and formulas (BII-11) to formula (BII-15) are preferred compounds represented by formula (BII- 1), Formula (BII-7), Formula (BII-9) and Formula (BII-15) are more preferred.
- the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone, or the compound represented by the formula (BI) and the compound represented by the formula (BII) may be used in combination. You may When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10: on a molar basis. 90 to 90:10, more preferably 20:80 to 80:20.
- the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
- the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyl oxyethyloxetane, 3-ethyl-3-(meth)acryloyloxyethyloxetane and the like.
- the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.
- the monomer (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.
- Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.
- vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; .
- the ratio of the structural units derived from each of the total structural units constituting the resin [K1] is Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (b); 40 to 98 mol% is preferably Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (b); 50 to 90 mol% is more preferable.
- the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent. be.
- the resin [K1] is, for example, the method described in the document "Experimental Methods for Polymer Synthesis” (written by Takayuki Otsu, Published by Kagaku Dojin, 1st Edition, 1st Edition, March 1, 1972) and the document It can be manufactured with reference to the cited document described in .
- a polymerization initiator e.g., a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and, for example, by replacing oxygen with nitrogen, a deoxygenated atmosphere is created, and while stirring, A method of heating and keeping warm can be mentioned.
- the polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the relevant field can be used.
- polymerization initiators include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.).
- the solvent any solvent can be used as long as it dissolves each monomer, and examples thereof include the solvents described later as the solvent (E) for the colored resin composition of the present invention.
- the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. You can use things.
- the solvent contained in the colored resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored resin composition of the present invention.
- the manufacturing process of the colored resin composition of the present invention can be simplified.
- the ratio of the structural units derived from each of the total structural units constituting the resin [K2] is Structural unit derived from (a); 2 to 45 mol% Structural unit derived from (b); 2 to 95 mol% Structural unit derived from (c); 1 to 65 mol% is preferably Structural unit derived from (a); 5 to 40 mol% Structural unit derived from (b); 5 to 80 mol% Structural unit derived from (c); 5 to 60 mol% is more preferable.
- the ratio of the structural units of the resin [K2] is in the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance and heat resistance of the resulting color filter are improved. And tend to be excellent in mechanical strength.
- the resin [K2] can be produced, for example, in the same manner as the method for producing the resin [K1].
- the ratio of the structural units derived from each of the total structural units constituting the resin [K3] is Structural unit derived from (a); 2 to 60 mol% Structural unit derived from (c); 40 to 98 mol% is preferably Structural unit derived from (a); 10 to 50 mol% Structural unit derived from (c); 50 to 90 mol% is more preferable.
- Resin [K3] can be produced, for example, in the same manner as the method for producing resin [K1].
- Resin [K4] is a carboxylic acid and/or carboxylic acid anhydride obtained by obtaining a copolymer of (a) and (c), and having (a) a cyclic ether having 2 to 4 carbon atoms possessed by (b). It can be produced by adding to First, a copolymer of (a) and (c) is produced in the same manner as the method for producing resin [K1]. In this case, the ratio of structural units derived from each is preferably the same ratio as mentioned for resin [K3].
- part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms of (b).
- the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst (e.g., tris ( dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) are placed in a flask and reacted at, for example, 60 to 130° C. for 1 to 10 hours to produce resin [K4].
- a reaction catalyst e.g., tris ( dimethylaminomethyl)phenol, etc.
- a polymerization inhibitor e.g., hydroquinone, etc.
- the amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By setting this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity balance of the resulting pattern tend to be good. be. Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b1) is preferable as (b) used in resin [K4], and (b1-1) is more preferable.
- the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).
- the amount of the polymerization inhibitor to be used is preferably 0.001 to 5 parts by weight per 100 parts by weight of the total amount of (a), (b) and (c).
- Reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by polymerization, and the like.
- the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
- a copolymer of (b) and (c) is obtained in the same manner as in the method for producing resin [K1] described above.
- the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be converted into a solid (powder) by a method such as reprecipitation. You may use what was taken out as.
- the ratio of the structural units derived from (b) and (c) is 5 to 95 moles of the structural units derived from (b) with respect to the total number of moles of all the structural units constituting the copolymer.
- % Structural unit derived from (c); 5 to 95 mol% is preferably Structural unit derived from (b); 10 to 90 mol% Structural unit derived from (c); 10 to 90 mol% is more preferable.
- the cyclic ether derived from (b) in the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic anhydride of (a).
- Resin [K5] can be obtained by reacting substances.
- the amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the cyclic ether has high reactivity and unreacted (b) does not easily remain, (b1) is preferable as (b) used in resin [K5], and (b1-1) is more preferable.
- Resin [K6] is a resin obtained by reacting resin [K5] with a carboxylic acid anhydride. The hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic anhydride is reacted with the carboxylic anhydride.
- Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride and the like.
- the amount of carboxylic acid anhydride to be used is preferably 0.5 to 1 mol per 1 mol of (a).
- Specific resins (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resin [K1] such as decyl acrylate/(meth)acrylic acid copolymer; glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth) Acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[ 5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)
- the resin (B) is more preferably at least one selected from the group consisting of resin [K1] and resin [K2], and particularly preferably resin [K2].
- the polystyrene equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and still more preferably 3,000 or more. 30,000 or less.
- the dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and still more preferably 1.001 or more. 01 or more and 4 or less.
- the acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH/g or more and 300 mg-KOH/g or less, more preferably 20 mg-KOH/g or more and 250 mg-KOH/g or less, More preferably 25 mg-KOH/g or more and 200 mg-KOH/g or less, still more preferably 30 mg-KOH/g or more and 150 mg-KOH/g or less, particularly preferably 60 mg-KOH/g or more and 135 mg-KOH/g g or less.
- the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined by titration with an aqueous potassium hydroxide solution, for example.
- the content of the resin (B) is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and still more preferably 15 to 30% by mass in 100% by mass of the solid content of the colored resin composition. is. When the content of the resin (B) is within the above range, the solubility of the unexposed area in the developer tends to be high.
- the polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D). is a (meth)acrylic acid ester compound.
- polymerizable compounds having one ethylenically unsaturated bond examples include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. etc., as well as monomers (a), (b) and (c) described above.
- Polymerizable compounds having two ethylenically unsaturated bonds include, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate and the like.
- the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds.
- examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl ) isocyanurate, ethylene glycol-modified pent
- the weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, still more preferably 100 or more and 3,000 or less, and even more preferably is 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.
- the content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, relative to the total solid content of the colored resin composition. , more preferably 10% by mass or more and 80% by mass or less, and still more preferably 12% by mass or more and 70% by mass or less.
- the polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat, and known polymerization initiators can be used.
- Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine oxide compounds.
- O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)- 3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl -6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethy
- O-acyl oxime compounds Irgacure (registered trademark) OXE01, OXE02 (manufactured by BASF), N-1919 (manufactured by ADEKA Co., Ltd.), and TR-PBG327 (manufactured by Changzhou Power Electronics New Materials Co., Ltd.), etc. may be used.
- Irgacure registered trademark
- OXE01, OXE02 manufactured by BASF
- N-1919 manufactured by ADEKA Co., Ltd.
- TR-PBG327 manufactured by Changzhou Power Electronics New Materials Co., Ltd.
- O-acyloxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and TR-PBG327 (N-acetoxy-1-(4- phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine), N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one- At least one selected from the group consisting of 2-imine and TR-PBG327 (N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexyl
- Alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1- and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like.
- Commercially available products such as Irgacure (registered trademark) 369, 907, 379 (manufactured by BASF) may be used as the alkylphenone compound.
- alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, Also included are 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxyacetophenone and benzyl dimethyl ketal.
- Biimidazole compounds include, for example, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2,3-dichlorophenyl)-4 ,4′,5,5′-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2′-bis(2-chlorophenyl)-4,4 ',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2' -bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403, JP-A
- Triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis( trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5
- Acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.
- Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
- the polymerization initiator (D) includes benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3′,4,4′-tetra(tert-butylperoxycarbonyl)benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate and titanocene compounds. These are preferably used in combination with a polymerization initiation aid (D1) (particularly an amine),
- the polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds, more preferably It is a polymerization initiator containing an O-acyl oxime compound.
- the content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. or less, more preferably 1 part by mass or more and 20 parts by mass or less.
- the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.
- the colored resin composition of the present invention may contain a polymerization initiation aid (D1).
- the polymerization initiation aid (D1) is a compound or a sensitizer used to accelerate the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D).
- the polymerization initiation aid (D1) is included, it is usually used in combination with the polymerization initiator (D).
- Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.
- amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-ethylhexyl dimethylaminobenzoate, N,N-dimethylp-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis( ethylmethylamino)benzophenone and the like, preferably 4,4'-bis(diethylamino)benzophenone.
- EAB-F manufactured by Hodogaya Chemical Industry Co., Ltd.
- Alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy and anthracene and 2-ethyl-9,10-dibutoxyanthracene.
- Thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone.
- Carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N -phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.
- the content thereof is preferably 0.5 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. It is 1 part by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less.
- the solvent (E) is not particularly limited, and solvents commonly used in the field can be used.
- the solvent (E) is, for example, an ester solvent (a solvent containing -COO- in the molecule but not containing -O-), an ether solvent (a solvent containing -O- in the molecule but not containing -COO-), Ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (containing OH in the molecule , —O—, —CO— and —COO—-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like. These solvents may be used in combination of two or more.
- Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and ⁇ -butyrolactone.
- Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether.
- propylene glycol monopropyl ether propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methylanisole and the like.
- Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether a
- Ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone non, cyclohexanone, isophorone, and the like.
- Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.
- Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
- Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.
- the solvent (E) is preferably a solvent containing at least one selected from propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and cyclohexanone.
- the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass, relative to the total amount of the colored resin composition. % by mass or less, more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less.
- the total solid content of the colored resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less. , more preferably 5% by mass or more and 30% by mass or less, and still more preferably 10% by mass or more and 25% by mass or less.
- Leveling agent (F) examples include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
- silicone-based surfactants include surfactants that have siloxane bonds in their molecules.
- Toray Silicone DC3PA, Toray SH7PA, Toray DC11PA, Toray SH21PA, Toray SH28PA, Toray SH29PA, Toray SH30PA, Toray SH8400 (trade name: Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC), etc. .
- fluorine-based surfactants include surfactants that have a fluorocarbon chain in the molecule.
- Florard registered trademark
- FC430 Florard FC431 (manufactured by Sumitomo 3M Co., Ltd.)
- Megafac registered trademark
- F142D Florado F171, Flora F172, Flora F173, Flora F177, Flora F183, Flora F554 R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemicals Laboratory Co., Ltd.).
- silicone-based surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule.
- Megafac registered trademark
- Megafac BL20 Megafac F475, F477 and F443 (manufactured by DIC Corporation) and the like can be mentioned.
- the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.0005% by mass or more and 1% by mass or less, relative to the total amount of the colored resin composition. 001% by mass or more and 0.5% by mass or less, more preferably 0.005% by mass or more and 0.1% by mass or less. This content does not include the content of the dispersant described above. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
- the colored resin composition if necessary, contains additives known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents, etc. It's okay.
- the colored resin composition contains a colorant (A), a resin (B), and optionally a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), and a solvent (E). , leveling agent (F) and other ingredients. Mixing can be performed by a known or commonly used device and conditions.
- the colorant (A) is mixed in advance with part or all of the solvent (E), and dispersed using a bead mill or the like until the average particle size becomes about 0.2 ⁇ m or less. It may be used, and is preferably used as a colorant-containing liquid.
- the dispersant and resin (B) may be blended.
- the coloring agent (A) may be used as a coloring agent-containing liquid obtained by previously dissolving it in part or all of the solvent (E).
- the desired colored resin composition can be prepared by mixing the colorant-containing liquid thus obtained with the remaining components so as to have a predetermined concentration.
- a color filter which may be a color conversion layer, can be formed from the colored resin composition of the present invention.
- a photolithography method, an inkjet method, a printing method, and the like can be used as a method for forming a colored pattern.
- the photolithographic method is preferred.
- the photolithographic method is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, exposed through a photomask, and developed.
- a colored coating film which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and/or not developing.
- the colored pattern or colored coating film thus formed is the color filter of the present invention.
- the film thickness of the color filter to be produced is not particularly limited, and can be appropriately adjusted according to the purpose and application. It is more preferably 0.5 ⁇ m or more and 6 ⁇ m or less, and still more preferably 0.8 ⁇ m or more and 4.5 ⁇ m or less.
- the substrate examples include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda-lime glass whose surface is coated with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; A thin film of aluminum, silver, silver/copper/palladium alloy, etc., is formed on the substrate. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.
- each color pixel by the photolithographic method can be carried out using a known or commonly used apparatus and conditions. For example, it can be produced as follows. First, a colored resin composition is applied onto a substrate, dried by heating (pre-baking) and/or dried under reduced pressure to remove volatile components such as solvents, and dried to obtain a smooth colored resin composition layer. Examples of coating methods include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
- the temperature for heat drying is preferably 30° C. or higher and 120° C. or lower, more preferably 50° C. or higher and 110° C. or lower.
- the heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less.
- the thickness of the colored resin composition layer is not particularly limited, and may be appropriately selected according to the desired thickness of the color filter.
- the colored resin composition layer is exposed through a photomask to form the desired colored pattern.
- the pattern on the photomask is not particularly limited, and a pattern suitable for the intended use is used.
- the exposure apparatus such as a mask aligner and a stepper can be used. is preferably used.
- exposure may be performed without using a photomask.
- the light source used for exposure is preferably a light source that emits light with a wavelength of 250 nm or more and 450 nm or less. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges.
- a filter that cuts this wavelength range
- light near 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges.
- a colored pattern is formed on the substrate by contacting the exposed colored resin composition layer with a developer for development.
- a developer for development By development, the unexposed portion of the colored resin composition layer is dissolved in the developer and removed.
- the developer for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide are preferred.
- the concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less.
- the developer may contain a surfactant.
- the developing method may be any of a puddle method, a dipping method, a spray method, and the like.
- the substrate may be tilted at any angle during development.
- the substrate after development is preferably washed with water.
- the post-baking temperature is preferably 150° C. or higher and 250° C. or lower, more preferably 160° C. or higher and 240° C. or lower.
- the post-baking time is preferably 1 minute or more and 120 minutes or less, more preferably 10 minutes or more and 60 minutes or less.
- the color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.
- the polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
- Apparatus HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: Tetrahydrofuran Flow rate: 1.0 mL/min Solid content concentration of analysis sample: 0.001 to 0.01% by mass Injection volume: 50 ⁇ L Detector: RI
- Calibration standard material TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
- the ratio (Mw/Mn) of the polystyrene-equivalent weight-average molecular weight and the number-average molecular weight obtained above was defined as the degree of dispersion.
- [Dye Synthesis Example 2 Synthesis of compound (BI-1)] 10 parts of the compound (BI-1a) obtained in Dye Synthesis Example 1, 1-naphthylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.0 parts, palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 0.38 part, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.7 parts, tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.) 6.4 parts, and dehydration 200 parts of 1,2-dimethoxyethane (manufactured by Kanto Kagaku Co., Ltd.) was mixed and stirred at 93° C.
- This reaction solution was stirred for 2 hours while being heated to 80° C. in an oil bath. After cooling the reaction solution in an ice bath, it was filtered to obtain a solid and a filtrate. Let this solid be crude material A1 and let a filtrate be filtrate A1. The obtained crude product A1 was washed with 50 parts of toluene and then washed twice with 250 parts of ion-exchanged water to obtain a solid. Let this solid be rough body B1. Filtrate A1, 50 parts of toluene, 229 parts of ion-exchanged water and 20.8 parts of 35% hydrochloric acid were put into a bottom-exhausted flask, stirred for 1 hour, and separated to obtain an organic layer.
- the resulting organic layer was separated and washed with a mixed liquid of 238 parts of ion-exchanged water and 12.5 parts of sodium carbonate, dried with 150 parts of magnesium sulfate, and filtered to remove solids.
- the organic layer obtained was distilled to obtain a solid. Let this solid be the crude body C1. Crude B1 and C1 were put into a flask equipped with a stirrer, 4 times mass of acetonitrile was added to the total mass of Crude B1 and C1, and the mixture was stirred for 1 hour. The solid obtained by filtering the mixed solution was washed with 1-fold mass of acetonitrile with respect to the total mass of crude B1 and crude C1. The washed solid was dried at 60° C. under reduced pressure to obtain 75.9 parts of the compound represented by the formula (CI-1a). Yield 90.6%.
- the copolymer (resin B-1) solution having a viscosity of 23 mPas and a solid content of 25.6% as measured by a Brookfield viscometer (23° C.) was maintained at 85° C. for 4 hours, then cooled to room temperature. got The resulting copolymer had a weight average molecular weight Mw of 8.0 ⁇ 10 3 , a dispersity of 2.1, and an acid value converted to solid content of 109 mg-KOH/g.
- Resin B-1 has the following structural units.
- Example 1 ⁇ Preparation of colorant dispersion (A-1) containing compound (I-23a-2)> Compound (I-23a-2) 5 parts, acrylic dispersant 3 parts, resin B-1 (solid content conversion) 2 parts, propylene glycol monomethyl ether acetate 79 parts, diacetone alcohol 10 parts, ethyl lactate 1 part, and 0 300 parts of 0.2 mm zirconia beads were mixed and the resulting mixture was shaken for 1 hour using paint conditioner (LAU). After that, the zirconia beads were removed by filtration to obtain a colorant dispersion (A-1).
- LiAU paint conditioner
- Example 2-7 Comparative Examples 1-2
- Colored resin compositions were obtained in the same manner as in Example 1, except that compound (I-23a-2) was changed to the following compounds.
- Example 2 Compound (I-5a-2)
- Example 3 Compound (I-17a-2)
- Example 4 Compound (I-35a-2)
- Example 5 Compound (I-40a-2)
- Example 6 Compound (I-42a-2)
- Example 7 Compound (I-4a-2) Comparative Example 1: Compound (x1) Comparative Example 2: Compound (x2)
- the CIE chromaticity coordinates and brightness Y were obtained when the colored resin compositions of Examples 1-7 or Comparative Examples 1-2 and the red resin composition of Preparation Example 1 were mixed at the ratios shown in Table 10.
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Abstract
Description
[1] 式(I)で表される化合物。
[式(I)中、
R1~R4及びR13は、互いに独立に、水素原子又は置換基を有していてもよい炭素数1~10の炭化水素基を表す。
R5~R12は、互いに独立に、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数1~5の炭化水素基を表す。
T1及びT2は、互いに独立に、置換基を有していてもよい2価の芳香族炭化水素基又は置換基を有していてもよい2価の芳香族複素環基を表す。
L1は、置換基を有していてもよい炭素数1~12のa価の脂肪族炭化水素基又は式(i)で表される基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
aは、2以上の整数を表す。
b及びcは、互いに独立に、1以上の整数を表す。
dは、0以上の整数を表す。
Xc-は、c価のアニオンを表す。]
[式(i)中、
T3は、置換基を有していてもよいa価の芳香族炭化水素基又は置換基を有していてもよいa価の芳香族複素環基を表す。
L2は、置換基を有していてもよい炭素数1~5の2価の脂肪族炭化水素基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
*はT2との結合手を表す。]
[2] 着色剤及び樹脂を含有し、前記着色剤が[1]に記載の化合物を含む着色樹脂組成物。
[3] さらに重合性化合物及び重合開始剤を含有する[2]に記載の着色樹脂組成物。
[4] [2]又は[3]に記載の着色樹脂組成物から形成されるカラーフィルタ。
[5] [4]に記載のカラーフィルタを含む表示装置。
本発明の化合物は、式(I)で表される化合物(以下、化合物(I)という場合がある)である。以下、式(I)を用いて本発明について詳述するが、化合物(I)には、式(I)の互変異性体も含まれる。
[式(I)中、
R1~R4及びR13は、互いに独立に、水素原子又は置換基を有していてもよい炭素数1~10の炭化水素基を表す。
R5~R12は、互いに独立に、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数1~5の炭化水素基を表す。
T1及びT2は、互いに独立に、置換基を有していてもよい2価の芳香族炭化水素基又は置換基を有していてもよい2価の芳香族複素環基を表す。
L1は、置換基を有していてもよい炭素数1~12のa価の脂肪族炭化水素基又は式(i)で表される基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
aは、2以上の整数を表す。
b及びcは、互いに独立に、1以上の整数を表す。
dは、0以上の整数を表す。
Xc-は、c価のアニオンを表す。]
[式(i)中、
T3は、置換基を有していてもよいa価の芳香族炭化水素基又は置換基を有していてもよいa価の芳香族複素環基を表す。
L2は、置換基を有していてもよい炭素数1~5の2価の脂肪族炭化水素基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
aは、上記と同様の意味を表す。
*はT2との結合手を表す。]
前記アルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基等の炭素数1~4のアルコキシ基が挙げられる。
前記置換アミノ基としては、1つ又は2つの炭化水素基を有するアミノ基が挙げられ、前記炭化水素基としては、上述の炭素数1~10の炭化水素基として例示した基が挙げられる。置換アミノ基としては、例えば、N-メチルアミノ基、N,N-ジメチルアミノ基、N-エチルアミノ基、N,N-ジエチルアミノ基、N-プロピルアミノ基、N,N-ジプロピルアミノ基、N-イソプロピルアミノ基、N,N-ジイソプロピルアミノ基、N-フェニルアミノ基、N,N-ジフェニルアミノ基、N,N-エチルメチルアミノ基、N,N-メチルフェニルアミノ基、N,N-エチルフェニルアミノ基等が挙げられる。
[式(i1)~(i8)中、Li1~Li8はそれぞれ独立して、炭素数1~5のアルカンジイル基を表し、該アルカンジイル基に含まれるメチレン基の1つが-O-で置き換わっている。*はT2との結合手を表す。]
この様なケイ素、及びリンからなる群より選ばれる少なくとも1つの元素と、酸素とからなるアニオンとしては、SiO3 2-、PO4 3-が挙げられる。
R1及びR3が、それぞれ独立して、置換基を有していてもよいフェニル基であり、且つ、R2及びR4が、それぞれ独立して、置換基を有していてもよい炭素数1~10の飽和鎖状炭化水素基であることがより好ましく、
R1及びR3が、それぞれ独立して、置換基を有していてもよいフェニル基であって、該フェニル基に結合するNに対してオルト位となる2つの結合位置のうち少なくとも一方に炭素数1~4のアルキル基を有する基であり、且つ、R2及びR4が、それぞれ独立して、置換基を有していてもよい炭素数1~6の飽和鎖状炭化水素基であることが更に好ましく、
R1及びR3が、それぞれ独立して、置換基を有していてもよいフェニル基であって、該フェニル基に結合するNに対してオルト位となる2つの結合位置のうち少なくとも一方に炭素数1~4のアルキル基を有する基であり、且つ、R2及びR4が、それぞれ独立して、置換基を有していてもよい炭素数2~6の飽和鎖状炭化水素基であることがより更に好ましく、
R1及びR3が、それぞれ独立して、置換基を有していてもよいフェニル基であって、該フェニル基に結合するNに対してオルト位となる2つの結合位置にそれぞれ炭素数1~3のアルキル基を有する基であり、且つ、R2及びR4が、それぞれ独立して、置換基を有していてもよい炭素数2~6の飽和鎖状炭化水素基であることが特に好ましい。
ここで、前記フェニル基が有していてもよい置換基としては、炭素数1~4のアルキル基、ハロゲン原子、ヒドロキシ基、アルコキシ基、ホルミル基、置換又は非置換のアミノ基、ニトロ基、シアノ基、-SO3 -、及び-SO3M(Mは前記と同じ)からなる群から選ばれる少なくとも1つ以上が挙げられ、中でも、炭素数1~4のアルキル基、ハロゲン原子、アルコキシ基、及び-SO3 -からなる群から選ばれる少なくとも1つ以上が好ましく、炭素数1~4のアルキル基、炭素数1~4のアルコキシ基、及び-SO3 -からなる群から選ばれる少なくとも1つ以上がより好ましい。
置換基を有していてもよい炭素数1~8のa価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は上記式(i2)又は式(i3)で表される基であることがより好ましく、
置換基を有していてもよい炭素数1~8のa価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は上記式(i-1)~(i-6)で表される基のいずれかであることが更に好ましく、
上記式(l-10a)~(l-16a)又は式(i-1)~(i-6)で表される基のいずれかであることが特に好ましい。
a×b=(c×d)+e ・・・(z)
[上記式中、a~dは前記と同じ意味を示す。eは、化合物(I)が置換基として有する-SO3 -の数を示す。]
[式(I-1)中、
R101及びR103が、それぞれ独立して、置換基を有していてもよいフェニル基であり、
R102及びR104が、それぞれ独立して、置換基を有していてもよい炭素数1~10の飽和鎖状炭化水素基であり、
R105~R112は、水素原子であり、
R113は、水素原子または置換基を有していてもよい炭素数1~6の飽和鎖状炭化水素基であり、
T101及びT102は、置換基を有していてもよい2価の芳香族炭化水素基であって、前記2価の芳香族炭化水素基を構成する芳香族炭化水素環が、ベンゼン環、ナフタレン環、又はそれら環が有する少なくとも1つの水素原子が炭素数1~4の飽和鎖状炭化水素基に置き換わった構造であり、
L101は、置換基を有していてもよい炭素数1~8のa101価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は式(i)で表される基において、T3が置換基を有していてもよいa101価の芳香族炭化水素基であり、L2が炭素数1~5の2価の飽和鎖状炭化水素基であって、該飽和鎖状炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であり、
a101は、2又は3であり、
d101は、1以上の整数を表し、
b、c、及びXc-は前記と同じ意味を示す。]
[式(I-2)中、
R201及びR203が、それぞれ独立して、置換基を有していてもよいフェニル基であり、
R202及びR204が、それぞれ独立して、置換基を有していてもよい炭素数1~10の飽和鎖状炭化水素基であり、
R205~R212は、水素原子であり、
R213は、水素原子または置換基を有していてもよい炭素数1~6の飽和鎖状炭化水素基であり、
T201及びT202は、置換基を有していてもよい2価の芳香族炭化水素基であって、前記2価の芳香族炭化水素基を構成する芳香族炭化水素環が、ベンゼン環、ナフタレン環、又はそれら環が有する少なくとも1つの水素原子が炭素数1~4の飽和鎖状炭化水素基に置き換わった構造であり、
L201は、置換基を有していてもよい炭素数1~8のa201価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は式(i)で表される基において、T3が置換基を有していてもよいa201価の芳香族炭化水素基であり、L2が炭素数1~5の2価の飽和鎖状炭化水素基であって、該飽和鎖状炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であり、
a201及びe201は、2又は3であり、
式(I-2)で表される化合物は、R201~R213、T201、T202、及びL201が有する水素原子のいずれかe201個が、-SO3 -で置換されている。]
L101及びL201としては、置換基を有していてもよい炭素数1~8のa価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は上記式(i1)~(i8)で表される基のいずれかであることが好ましく、
置換基を有していてもよい炭素数1~8のa価の飽和鎖状炭化水素基であって、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つが-O-で置き換わっている基であるか、又は上記式(i2)又は式(i3)で表される基であることがより好ましく、
上記式(l-10a)~(l-16a)又は式(i-1)~(i-6)で表される基のいずれかであることが特に好ましい。
化合物(I’)は、例えば、式(B-I)で表される化合物と、式(C-I)で表される化合物とを、反応させることにより製造することができる。
[式(B-I)及び(C-I)中、R1~R13、T2、L1、及びaは、それぞれ前記と同じ意味を表す。T1Bは、前記T1において窒素原子と結合する結合手とは異なる結合手が水素原子に置き換わった基を表す。]
a×b-e>0 ・・・(z1)
[上記式中、a、bは式(I)のa、bと同じ意味である。eは、化合物(I’)が置換基として有する-SO3 -の数を示す。]
縮合剤の使用量は、式(B-I)で表される化合物1質量部に対して、好ましくは0.1質量部以上20質量部以下であり、より好ましくは0.2質量部以上10質量部以下である。
化合物(I’’)は、化合物(I’)と、アニオンX1のアルカリ金属塩又はプロトン酸とを、混合することで製造することができる。アルカリ金属としては、リチウム、ナトリウム及びカリウム等が挙げられる。
中でも、溶解性の観点から、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、ジメチルスルホキシド、メタノール、エタノール、イソプロパノール及び水からなる群から選択される少なくとも1種の溶媒が好ましい。
溶媒の使用量は、化合物(I’)1質量部に対して、好ましくは1質量部以上30質量部以下であり、より好ましくは2質量部以上20質量部以下である。
溶媒が水である場合、酢酸や塩酸等の酸を加えてもよい。
化合物(I’’’)は、化合物(I’)と、硫酸とを混合することで製造することができる。
本発明の着色樹脂組成物は、着色剤(以下、着色剤(A)という場合がある。)及び樹脂(以下、樹脂(B)という場合がある。)を含有し、前記着色剤が、化合物(I)を含む。
本発明の着色樹脂組成物は、さらに重合性化合物(以下、重合性化合物(C)という場合がある。)及び重合開始剤(以下、重合開始剤(D)という場合がある。)を含むことが好ましい。
本発明の着色樹脂組成物は、さらに溶剤(以下、溶剤(E)という場合がある。)を含むことが好ましい。
本発明の着色樹脂組成物は、さらにレベリング剤(以下、レベリング剤(F)という場合がある。)を含んでもよい。
なお、本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組合せて使用することができる。
着色剤(A)は化合物(I)を含有する。これにより、得られるカラーフィルタの明度が良好となり、好ましくは得られるカラーフィルタの薄膜化も可能となる。また、着色剤(A)が化合物(I)を含有することにより、好ましくは、得られるカラーフィルタの耐熱性及び/又は耐溶剤性も良好となる。化合物(I)としては、上述の化合物(I)が挙げられ、その好ましい態様も同様である。
C.I.ソルベントイエロー4、14、15、23、24、25、38、62、63、68、79、81、82、83、89、94、98、99、117、162、163、167、189;
C.I.ソルベントレッド24、45、49、90,91、111、118、119、122、124、125、127、130、132、143、145、146、150、151、155、160、168、169、172、175、181、207、218、222、227、230、245、247;
C.I.ソルベントオレンジ2、7、11、15、26、41、54、56、77、86、99;
C.I.ソルベントバイオレット11、13、14、26、31、36、37、38、45、47、48、51、59、60;
C.I.ソルベントブルー4、5、14、18、35、36、37、38、44、45、58、59、59:1、63、67、68、69、70、78、79、83、90、94、97、98、100、101、102、104、105、111、112、122、128、132、136、139;
C.I.ソルベントグリーン1、3、4、5、7、28、29、32、33、34、35;等のC.I.ソルベント染料、
C.I.アシッドイエロー1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251;
C.I.アシッドレッド1、4、8、14、17、18、26、27、29、31、33、34、35、37、40、42、44、50、51、52、57、66、73、76、80、87、88、91、92、94、95、97、98、103、106、111、114、129、133、134、138、143、145、150、151、155、158、160、172、176、182、183、195、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、289、308、312、315、316、339、341、345、346、349、382、383、388、394、401、412、417、418、422、426;
C.I.アシッドオレンジ6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、149、162、169、173;
C.I.アシッドバイオレット6B、7、9、15、16、17、19、21、23、24、25、30、34、38、49、72、102;
C.I.アシッドブルー1、3、5、7、9、11、13、15、17、18、22、23、24、25、26、27、29、34、38、40、41、42、43、45、48、51、54、59、60、62、70、72、74、75、78、80、82、83、86、87、88、90、90:1、91、92、93、93:1、96、99、100、102、103、104、108、109、110、112、113、117、119、120、123、126、127、129、130、131、138、140、142、143、147、150、151、154、158、161、166、167、168、170、171、175、182、183、184、187、192、199、203、204、205、210、213、229、234、236、242、243、249、256、259、267、269、278、280、285、290、296、315、324:1、335、340;
C.I.アシッドグリーン1、3、5、6、7、8、9、11、13、14、15、16、22、25、27、28、41、50、50:1、58、63、65、80、104、105、106、109;等のC.I.アシッド染料、
C.I.ダイレクトイエロー2、4、28、33、34、35、38、39、43、44、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、132、136、138、141;
C.I.ダイレクトレッド79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250;
C.I.ダイレクトオレンジ26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107;
C.I.ダイレクトバイオレット47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104;
C.I.ダイレクトブルー1、2、3、6、8、15、22、25、28、29、40、41、42、47、52、55、57、71、76、77、78、80、81、84、85、86、87、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、120、137、149、150、153、155、156、158、159、160、161、162、163、164、165、166、167、168、170、171、172、173、188、189、190、192、193、194、195、196、198、199、200、201、202、203、207、209、210、212、213、214、222、225、226、228、229、236、237、238、242、243、244、245、246、247、248、249、250、251、252、256、257、259、260、268、274、275、293;
C.I.ダイレクトグリーン25、27、31、32、34、37、63、65、66、67、68、69、72、79、82;等のC.I.ダイレクト染料、
C.I.ディスパースイエロー51、54、76;
C.I.ディスパースバイオレット26、27;
C.I.ディスパースブルー1、14、56、60;等のC.I.ディスパース染料、
C.I.ベーシックレッド1、9、10;
C.I.ベーシックブルー1、3、5、7、9、19、21、22、24、25、26、28、29、40、41、45、47、54、58、59、60、64、65、66、67、68、81、83、88、89;
C.I.ベーシックバイオレット2;
C.I.ベーシックグリーン1;等のC.I.ベーシック染料、
C.I.リアクティブイエロー2、76、116;
C.I.リアクティブオレンジ16;
C.I.リアクティブレッド36;等のC.I.リアクティブ染料、
C.I.モーダントイエロー5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;
C.I.モーダントレッド1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、27、29、30、32、33、36、37、38、39、41、42、43、45、46、48、52、53、56、62、63、71、74、76、78、85、86、88、90、94、95;
C.I.モーダントオレンジ3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48;
C.I.モーダントバイオレット1、1:1、2、3、4、5、6、7、8、10、11、14、15、16、17、18、19、21、22、23、24、27、28、30、31、32、33、36、37、39、40、41、44、45、47、48、49、53、58;
C.I.モーダントブルー1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83、84;
C.I.モーダントグリーン1、3、4、5、10、13、15、19、21、23、26、29、31、33、34、35、41、43、53;等のC.I.モーダント染料、
C.I.バットグリーン1;等のC.I.バット染料等のカラーインデックス(C.I.)番号の染料が挙げられる。
ピグメントに分類されている顔料としては、例えば、C.I.ピグメントイエロー1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、129、137、138、139、147、148、150、153、154、166、173、185、194、214、231等の黄色顔料;
C.I.ピグメントオレンジ13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等のオレンジ色顔料;
C.I.ピグメントレッド9、97、105、122、144、166、168、176、177、180、190、192、209、215、216、224、242、254、255、264、265、266、268、269、273等の赤色顔料;
C.I.ピグメントブルー15、15:1、15:2、15:3、15:4、15:6、16、60等の青色顔料;
C.I.ピグメントバイオレット1、19、23、32、36、38等のバイオレット色顔料;
C.I.ピグメントグリーン7、36、58、59、62、63等の緑色顔料;
C.I.ピグメントブラウン23、25等のブラウン色顔料;
C.I.ピグメントブラック1、7等の黒色顔料;が挙げられる。
ここで、本明細書における「固形分の総量」とは、着色樹脂組成物の総量から溶剤の含有量を除いた量のことをいう。固形分の総量及びこれに対する各成分の含有量は、例えば、液体クロマトグラフィー又はガスクロマトグラフィー等の公知の分析手段で測定することができる。
樹脂(B)は、特に限定されないが、アルカリ可溶性樹脂であることが好ましい。樹脂(B)としては、以下の樹脂[K1]~[K6]等が挙げられる。
樹脂[K1];不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種の単量体(a)(以下「(a)」という場合がある)に由来する構造単位と、炭素数2~4の環状エーテル構造とエチレン性不飽和結合とを有する単量体(b)(以下「(b)」という場合がある)に由来する構造単位とを有する共重合体;
樹脂[K2];(a)に由来する構造単位と(b)に由来する構造単位と、(a)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる。)(以下「(c)」という場合がある)に由来する構造単位とを有する共重合体;
樹脂[K3];(a)に由来する構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K4];(a)に由来する構造単位に(b)を付加させた構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K5];(b)に由来する構造単位に(a)を付加させた構造単位と(c)に由来する構造単位とを有する共重合体;
樹脂[K6];(b)に由来する構造単位に(a)を付加させ、カルボン酸無水物をさらに付加させた構造単位と(c)に由来する構造単位とを有する共重合体。
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3-ビニルフタル酸、4-ビニルフタル酸、3,4,5,6-テトラヒドロフタル酸、1,2,3,6-テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸及び1,4-シクロヘキセンジカルボン酸等の不飽和ジカルボン酸;
メチル-5-ノルボルネン-2,3-ジカルボン酸、5-カルボキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-メチルビシクロ[2.2.1]ヘプト-2-エン及び5-カルボキシ-6-エチルビシクロ[2.2.1]ヘプト-2-エン等のカルボキシ基を含有するビシクロ不飽和化合物;
フマル酸及びメサコン酸を除く上記不飽和ジカルボン酸の無水物等のカルボン酸無水物;
こはく酸モノ〔2-(メタ)アクリロイルオキシエチル〕及びフタル酸モノ〔2-(メタ)アクリロイルオキシエチル〕等の2価以上の多価カルボン酸の不飽和モノ〔(メタ)アクリロイルオキシアルキル〕エステル類;
α-(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和アクリレート類;等が挙げられる。
これらのうち、共重合反応性の点や得られる樹脂のアルカリ水溶液への溶解性の点から、アクリル酸、メタクリル酸及び無水マレイン酸等が好ましい。
なお本明細書において、「(メタ)アクリル酸」とは、アクリル酸及びメタクリル酸よりなる群から選ばれる少なくとも1種を表す。「(メタ)アクリロイル」及び「(メタ)アクリレート」等の表記も、同様の意味を有する。
Xa及びXbは、互いに独立に、単結合、*-Rc-、*-Rc-O-、*-Rc-S-又は*-Rc-NH-を表す。
Rcは、炭素数1~6のアルカンジイル基を表す。
*は、Oとの結合手を表す。]
2-ヒドロキシエチル(メタ)アクリレート及び2-ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル;
マレイン酸ジエチル、フマル酸ジエチル及びイタコン酸ジエチル等のジカルボン酸ジエステル;
ビシクロ[2.2.1]ヘプト-2-エン、5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチルビシクロ[2.2.1]ヘプト-2-エン、5-(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5-メトキシビシクロ[2.2.1]ヘプト-2-エン、5-エトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジメトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジエトキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチル-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-tert-ブトキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-フェノキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(tert-ブトキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン及び5,6-ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン等のビシクロ不飽和化合物;
N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、N-スクシンイミジル-3-マレイミドベンゾエート、N-スクシンイミジル-4-マレイミドブチレート、N-スクシンイミジル-6-マレイミドカプロエート、N-スクシンイミジル-3-マレイミドプロピオネート及びN-(9-アクリジニル)マレイミド等のジカルボニルイミド誘導体;
スチレン、o-メチルスチレン、m-メチルスチレン、p-メチルスチレン、ビニルトルエン及びp-メトキシスチレン等のビニル基含有芳香族化合物;(メタ)アクリロニトリル等のビニル基含有ニトリル;塩化ビニル及び塩化ビニリデン等のハロゲン化炭化水素;(メタ)アクリルアミド等のビニル基含有アミド;酢酸ビニル等のエステル;1,3-ブタジエン、イソプレン及び2,3-ジメチル-1,3-ブタジエン等のジエン;等が挙げられる。
これらのうち、共重合反応性及び耐熱性の点から、スチレン、ビニルトルエン、トリシクロ[5.2.1.02,6]デカン-8-イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン-9-イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デセン-8-イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デセン-9-イル(メタ)アクリレート、N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、ビシクロ[2.2.1]ヘプト-2-エン、2-ヒドロキシエチル(メタ)アクリレート、及びベンジル(メタ)アクリレートからなる群から選択される少なくとも1種以上を用いることが好ましい。
(a)に由来する構造単位;2~60モル%
(b)に由来する構造単位;40~98モル%
であることが好ましく、
(a)に由来する構造単位;10~50モル%
(b)に由来する構造単位;50~90モル%
であることがより好ましい。
樹脂[K1]の構造単位の比率が、上記の範囲にあると、着色樹脂組成物の保存安定性、着色パターンを形成する際の現像性、及び得られるカラーフィルタの耐溶剤性に優れる傾向がある。
(a)に由来する構造単位;2~45モル%
(b)に由来する構造単位;2~95モル%
(c)に由来する構造単位;1~65モル%
であることが好ましく、
(a)に由来する構造単位;5~40モル%
(b)に由来する構造単位;5~80モル%
(c)に由来する構造単位;5~60モル%
であることがより好ましい。
樹脂[K2]の構造単位の比率が、上記の範囲にあると、着色樹脂組成物の保存安定性、着色パターンを形成する際の現像性、並びに、得られるカラーフィルタの耐溶剤性、耐熱性及び機械強度に優れる傾向がある。
(a)に由来する構造単位;2~60モル%
(c)に由来する構造単位;40~98モル%
であることが好ましく、
(a)に由来する構造単位;10~50モル%
(c)に由来する構造単位;50~90モル%
であることがより好ましい。
樹脂[K3]は、例えば、樹脂[K1]の製造方法として記載した方法と同様に製造することができる。
まず(a)と(c)との共重合体を、樹脂[K1]の製造方法として記載した方法と同様に製造する。この場合、それぞれに由来する構造単位の比率は、樹脂[K3]で挙げたもの同じ比率であることが好ましい。
(a)と(c)との共重合体の製造に引き続き、フラスコ内雰囲気を窒素から空気に置換し、(b)、カルボン酸又はカルボン酸無水物と環状エーテルとの反応触媒(例えばトリス(ジメチルアミノメチル)フェノール等)及び重合禁止剤(例えばハイドロキノン等)等をフラスコ内に入れて、例えば、60~130℃で、1~10時間反応することにより、樹脂[K4]を製造することができる。
(b)の使用量は、(a)100モルに対して、5~80モルが好ましく、より好ましくは10~75モルである。この範囲にすることにより、着色樹脂組成物の保存安定性、パターンを形成する際の現像性、並びに、得られるパターンの耐溶剤性、耐熱性、機械強度及び感度のバランスが良好になる傾向がある。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K4]に用いる(b)としては(b1)が好ましく、更に(b1-1)が好ましい。
前記反応触媒の使用量は、(a)、(b)及び(c)の合計量100質量部に対して0.001~5質量部が好ましい。前記重合禁止剤の使用量は、(a)、(b)及び(c)の合計量100質量部に対して0.001~5質量部が好ましい。
仕込方法、反応温度及び時間等の反応条件は、製造設備や重合による発熱量等を考慮して適宜調整することができる。なお、重合条件と同様に、製造設備や重合による発熱量等を考慮し、仕込方法や反応温度を適宜調整することができる。
(b)及び(c)に由来する構造単位の比率は、前記の共重合体を構成する全構造単位の合計モル数に対して、それぞれ、(b)に由来する構造単位;5~95モル%
(c)に由来する構造単位;5~95モル%
であることが好ましく、
(b)に由来する構造単位;10~90モル%
(c)に由来する構造単位;10~90モル%
であることがより好ましい。
前記の共重合体に反応させる(a)の使用量は、(b)100モルに対して、5~80モルが好ましい。環状エーテルの反応性が高く、未反応の(b)が残存しにくいことから、樹脂[K5]に用いる(b)としては(b1)が好ましく、更に(b1-1)が好ましい。
カルボン酸無水物としては、無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等が挙げられる。カルボン酸無水物の使用量は、(a)の使用量1モルに対して、0.5~1モルが好ましい。
樹脂(B)の分散度[重量平均分子量(Mw)/数平均分子量(Mn)]は、好ましくは1以上6以下であり、より好ましくは1.001以上4以下であり、更に好ましくは1.01以上4以下である。
重合性化合物(C)は、重合開始剤(D)から発生した活性ラジカル及び/又は酸によって重合しうる化合物であり、例えば、重合性のエチレン性不飽和結合を有する化合物等が挙げられ、好ましくは(メタ)アクリル酸エステル化合物である。
重合開始剤(D)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始しうる化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。
アルキルフェノン化合物としては、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン、2-ヒドロキシ-2-メチル-1-〔4-(2-ヒドロキシエトキシ)フェニル〕プロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、2-ヒドロキシ-2-メチル-1-(4-イソプロペニルフェニル)プロパン-1-オンのオリゴマー、α,α-ジエトキシアセトフェノン及びベンジルジメチルケタールも挙げられる。
これらは、後述の重合開始助剤(D1)(特にアミン化合物)と組み合わせて用いることが好ましい。
本発明の着色樹脂組成物は、重合開始助剤(D1)を含んでいてもよい。重合開始助剤(D1)は、重合開始剤(D)によって重合が開始された重合性化合物(C)の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(D1)を含む場合、通常、重合開始剤(D)と組み合わせて用いられる。
溶剤(E)は、特に限定されず、当該分野で通常使用される溶剤を用いることができる。
溶剤(E)は、例えば、エステル溶剤(分子内に-COO-を含み、-O-を含まない溶剤)、エーテル溶剤(分子内に-O-を含み、-COO-を含まない溶剤)、エーテルエステル溶剤(分子内に-COO-と-O-とを含む溶剤)、ケトン溶剤(分子内に-CO-を含み、-COO-を含まない溶剤)、アルコール溶剤(分子内にOHを含み、-O-、-CO-及び-COO-を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等が挙げられる。これらの溶剤は、2種以上を併用してもよい。
レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
着色樹脂組成物は、必要に応じて、充填剤、他の高分子化合物、密着促進剤、クエンチャー、酸化防止剤、光安定剤、連鎖移動剤等、当該技術分野で公知の添加剤を含んでもよい。
着色樹脂組成物は、着色剤(A)、樹脂(B)、並びに必要に応じて用いられる重合性化合物(C)、重合開始剤(D)、重合開始助剤(D1)、溶剤(E)、レベリング剤(F)及びその他の成分を混合することにより調製できる。混合は公知又は慣用の装置や条件により行うことができる。
着色剤(A)は、予め溶剤(E)の一部又は全部と混合し、平均粒子径が0.2μm以下程度となるまで、ビーズミル等を用いて分散させて得られた着色剤含有液として用いてもよく、着色剤含有液として用いることが好ましい。この際、必要に応じて前記分散剤、樹脂(B)の一部又は全部を配合してもよい。また、着色剤(A)は、予め溶剤(E)の一部又は全部に溶解させて得られた着色剤含有液として用いてもよい。このようにして得られた着色剤含有液に、残りの成分を、所定の濃度となるように混合することにより、目的の着色樹脂組成物を調製できる。
本発明の着色樹脂組成物から、色変換層であってもよいカラーフィルタを形成することができる。着色パターンを形成する方法としては、フォトリソグラフ法、インクジェット法、印刷法等が挙げられる。中でも、フォトリソグラフ法が好ましい。フォトリソグラフ法は、前記着色樹脂組成物を基板に塗布し、乾燥させて着色樹脂組成物層を形成し、フォトマスクを介して該着色樹脂組成物層を露光して、現像する方法である。フォトリソグラフ法において、露光の際にフォトマスクを用いないこと、及び/又は現像しないことにより、上記着色樹脂組成物層の硬化物である着色塗膜を形成することができる。このように形成した着色パターンや着色塗膜が本発明のカラーフィルタである。
まず、着色樹脂組成物を基板上に塗布し、加熱乾燥(プリベーク)及び/又は減圧乾燥することにより溶剤等の揮発成分を除去して乾燥させ、平滑な着色樹脂組成物層を得る。
塗布方法としては、スピンコート法、スリットコート法、スリット アンド スピンコート法等が挙げられる。
加熱乾燥を行う場合の温度は、30℃以上120℃以下が好ましく、50℃以上110℃以下がより好ましい。また加熱時間としては、10秒間以上60分間以下であることが好ましく、30秒間以上30分間以下であることがより好ましい。
減圧乾燥を行う場合は、50Pa以上150Pa以下の圧力下、20℃以上25℃以下の温度範囲で行うことが好ましい。
着色樹脂組成物層の膜厚は、特に限定されず、目的とするカラーフィルタの膜厚に応じて適宜選択すればよい。
現像方法は、パドル法、ディッピング法及びスプレー法等のいずれでもよい。さらに現像時に基板を任意の角度に傾けてもよい。
現像後の基板は、水洗されることが好ましい。
前記カラーフィルタは、表示装置(例えば、液晶表示装置、有機EL装置、電子ペーパー等)及び固体撮像素子に用いられるカラーフィルタとして有用である。
装置:HLC-8120GPC(東ソー(株)製)
カラム:TSK-GELG2000HXL
カラム温度:40℃
溶剤:テトラヒドロフラン
流速:1.0mL/分
分析試料の固形分濃度:0.001~0.01質量%
注入量:50μL
検出器:RI
校正用標準物質:TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500(東ソー(株)製)
上記で得られたポリスチレン換算の重量平均分子量及び数平均分子量の比(Mw/Mn)を分散度とした。
[色素合成例1:化合物(B-I-1a)の合成]
4-ブロモ-3,5-ジメチルフェノール(東京化成工業(株)製)14.8部及びN,N-ジメチルホルムアミド(関東化学(株)製)134部を混合し、60%水素化ナトリウム(関東化学(株)製)3.2部をゆっくり加え、40℃に昇温した。1,3,5-トリス(ブロモメチル)ベンゼン(東京化成工業(株)製)8.0部及びN,N-ジメチルホルムアミド(関東化学(株)製)34部を滴下し、5時間撹拌した。10℃に冷却後、水168部を加えた。25℃に昇温後、酢酸エチル(関東化学(株)製)168部を添加後、酢酸エチル層を抽出し、濃縮し、60℃で減圧乾燥したところ、式(B-I-1a)で表される化合物を13.4部得た(収率83%)。
(質量分析)イオン化モード=ESI+: m/z= 715.2
色素合成例1で得られた化合物(B-I-1a)10部、1-ナフチルアミン(東京化成工業(株)製)7.0部、酢酸パラジウム(東京化成工業(株)製)0.38部、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(東京化成工業(株)製)1.7部、tert-ブトキシナトリウム(東京化成工業(株)製)6.4部、及び脱水1,2-ジメトキシエタン(関東化学(株)製)200部を混合し、93℃、10時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-1)で表される化合物を8.2部得た(収率65%)。
(質量分析)イオン化モード=ESI+: m/z= 904.6
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコにビス(ジベンジリデンアセトン)パラジウム(0)(東京化成工業(株)製)0.27部、2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル(シグマアルドリッチ社製)0.57部、ナトリウム tert-ブトキシド(東京化成工業(株)製)42.1部及び4,4’-ジクロロベンゾフェノン(東京化成工業(株)製)50部を投入した後、2,6-ジメチルアニリン(東京化成工業(株)製)48.3部とトルエン432部との混合溶液をフラスコに滴下した。この反応液をオイルバスにて80℃に加熱しながら2時間撹拌した。反応液を氷浴にて冷却した後、ろ過を行い固体とろ液とを得た。この固体を粗体A1、ろ液をろ液A1とする。得られた粗体A1をトルエン50部にて洗浄し、次いでイオン交換水250部にて2度洗浄し固体を得た。この固体を粗体B1とする。底排付フラスコにろ液A1、トルエン50部、イオン交換水229部及び35%塩酸20.8部を投入し1時間撹拌した後、分液して有機層を得た。得られた有機層をイオン交換水238部と炭酸ナトリウム12.5部との混合液にて分液洗浄した後、硫酸マグネシウム150部にて乾燥し、固体をろ別して除去した。得られた有機層を蒸留して固体を得た。この固体を粗体C1とする。撹拌装置を備えたフラスコに粗体B1と粗体C1とを投入し、粗体B1と粗体C1との総質量に対し4倍質量のアセトニトリルを投入し1時間撹拌した。該混合液をろ過して得られた固体を、粗体B1と粗体C1との総質量に対し1倍質量のアセトニトリルにて洗浄した。洗浄後の固体を減圧下60℃にて乾燥し、式(C-I-1a)で表される化合物を75.9部得た。収率90.6%。
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに式(C-I-1a)で表される化合物50部及びN,N-ジメチルホルムアミド188部を投入し、氷浴にて冷却しながら30分撹拌した。該フラスコにカリウム tert-ブトキシド(東京化成工業(株)製)40部を投入し、氷浴にて冷却しながらさらに1時間撹拌した。反応液を氷冷したままヨードエタン(東京化成工業(株)製)55.6部を滴下した。反応液をオイルバスを用いて35℃に昇温し5時間撹拌した後、室温まで放冷した。撹拌装置を備えた別のフラスコに10%塩化ナトリウム水溶液1000部を投入し、撹拌しながら前記反応液を滴下した。30分撹拌した後ろ過し固体を得た。得られた固体をイオン交換水500部にて3回洗浄し、減圧下60℃にて乾燥し式(C-I-1)で表される化合物53.0部を得た。収率93.5%。
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに、色素合成例2で得られた式(B-I-1)で表される化合物6.8部、色素合成例4で得られた式(C-I-1)で表される化合物11部およびトルエン48部を投入した後、次いで、オキシ塩化リン(富士フイルム和光純薬(株)製)4.6部を加え110℃で8時間撹拌した。次いで反応混合物を室温に冷却した後、クロロホルム200部および飽和食塩水200部を注ぎ、分液操作で水層を除去した。有機層をエバポレーターで溶媒留去した後、得られた青紫色固体をカラムクロマトグラフィーで精製した。さらに、得られた青紫色固体にクロロホルム100部およびトルエン500部を注いで洗浄した後、減圧下60℃で乾燥して、式(I-23a-1)で表される化合物を7.5部得た(収率39%)。
(質量分析)イオン化モード=ESI+: m/z= 760.6、3価
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに、ホスホタングステン酸水和物(ケギン型リンタングステン酸;シグマアルドリッチ(株)製)4.3部、メタノール12部および水7.9部を投入した後、55℃で混合し、リンタングステン酸溶液を調製した。該フラスコに色素合成例5で得られた式(I-23a-1)で表される化合物を3.0部投入し、55℃で4時間撹拌した。反応溶液を濃縮後、水200部を投入して、1時間分散させた後、濾過して青色固体を得た。さらに、青色固体にメタノール800部を投入して、1時間分散させた後、濾過を行い、減圧下60℃で乾燥して、式(I-23a-2)で表される化合物を4.7部得た(収率72%)。
(質量分析)イオン化モード=MALDI+: m/z= 2280.0
イオン化モード=MALDI-: m/z= 2902.5
4-ブロモ-3,5-ジメチルフェノール(東京化成工業(株)製)7.4部及びN,N-ジメチルホルムアミド(関東化学(株)製)71部を混合し、60%水素化ナトリウム(関東化学(株)製)1.6部をゆっくり加え、40℃に昇温した。1,4-ビス(ブロモメチル)ベンゼン(東京化成工業(株)製)4.4部及びN,N-ジメチルホルムアミド(関東化学(株)製)18部を滴下し、5時間撹拌した。10℃に冷却後、水93部を加えた。25℃に昇温後、酢酸エチル(関東化学(株)製)93部を添加後、酢酸エチル層を抽出し、濃縮し、60℃で減圧乾燥したところ、式(B-I-2a)で表される化合物を5.1部得た(収率45%)。
(質量分析)イオン化モード=ESI+: m/z= 503.2
色素合成例7で得られた式(B-I-2a)で表される化合物9.5部、1-ナフチルアミン(東京化成工業(株)製)7.0部、酢酸パラジウム(東京化成工業(株)製)0.89部、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(東京化成工業(株)製)4.1部、tert-ブトキシナトリウム(東京化成工業(株)製)5.8部、及び脱水1,2-ジメトキシエタン(関東化学(株)製)190部を混合し、93℃、10時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-2)で表される化合物を7.3部得た(収率61%)。
(質量分析)イオン化モード=ESI+: m/z= 629.5
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに、色素合成例8で得られた式(B-I-2)で表される化合物4.0部、色素合成例4で得られた式(C-I-1)で表される化合物22部およびトルエン112部を投入した後、次いで、オキシ塩化リン(富士フイルム和光純薬(株)製)5.9部を加え90℃で6時間半撹拌した。次いで反応混合物を室温に冷却した後、これにクロロホルム300部を加えて得られた溶液を酢酸エチル3300部に注ぎ、ろ過して得られた湿固体を酢酸エチルで洗浄した。得られた固体を減圧下60℃で乾燥し、カラムクロマトグラフィーで精製した。減圧下60℃で乾燥したところ、式(I-5a-1)で表される化合物を1.0部得た(収率10%)。
(質量分析)イオン化モード=ESI+: m/z= 774.6、2価
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに、ホスホタングステン酸水和物(シグマアルドリッチ(株)製)2.0部、ジメチルスルホキシド20部および色素合成例9で得られた式(I-5a-1)で表される化合物を0.6部投入し、45℃で6時間撹拌した。25℃へ冷却後、反応液に蒸留水80部を投入して、1時間分散させた後、濾過して青色固体を得た。さらに、青色固体にメタノール60部を投入して、1時間分散させた後、濾過を行い、減圧下60℃で乾燥して、式(I-5a-2)で表される化合物を1.8部得た(定量的)。
(質量分析)イオン化モード=MALDI+: m/z= 1545.7
イオン化モード=MALDI-: m/z= 2902.5
色素合成例7で得られた式(B-I-2a)で表される化合物4.0部、1-プロピルアミン(東京化成工業(株)製)4.4部、トリス(ジベンジリデンアセトン)ジパラジウム(0)(富士フイルム和光純薬(株)製)0.72部、2-ジシクロヘキシルホスフィノ-2’-(ジメチルアミノ)ビフェニル(富士フイルム和光純薬(株)製)0.92部、tert-ブトキシナトリウム(東京化成工業(株)製)2.44部、及び脱水1,2-ジメトキシエタン(関東化学(株)製)80部を混合し、40℃、2時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-3a)で表される化合物を3.24部得た(収率89%)。
(質量分析)イオン化モード=ESI+: m/z= 461.5
色素合成例11で得られた式(B-I-3a)で表される化合物3.0部、1-ブロモナフタレン(東京化成工業(株)製)2.70部、酢酸パラジウム(東京化成工業(株)製)0.177部、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(東京化成工業(株)製)0.81部、tert-ブトキシナトリウム(東京化成工業(株)製)2.01部、及び脱水1,2-ジメトキシエタン(関東化学(株)製)60部を混合し、93℃、10時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-3)で表される化合物を3.45部得た(収率74%)。
(質量分析)イオン化モード=ESI+: m/z= 713.6
色素合成例4で得られた式(C-I-1)で表される化合物2.01部、色素合成例12得られた式(B-I-3)で表される化合物1.35部、オキシ塩化リン(富士フイルム和光純薬(株)製)0.75部、及び脱水トルエン(関東化学(株)製)9.9部を混合し、100℃、3時間撹拌した。25℃に冷却後、得られた混合物を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(I-17a-1)で表される化合物を2.31部得た(収率68%)。
(質量分析)イオン化モード=ESI+: m/z= 815.7、2価
色素合成例13で得られた式(I-17a-1)で表される化合物1.95部、ホスホタングステン酸水和物(シグマアルドリッチ(株)製)2.91部、及び脱水ジメチルスルホキシド(関東化学(株)製)10.2部を混合し、45℃、6時間撹拌した。25℃に冷却後、水78部を加え、得られた青色沈殿物を濾過した。得られた残渣を60℃で減圧乾燥したところ、式(I-17a-2)で表される化合物を3.3部得た(収率84%)。
(質量分析)イオン化モード=MALDI+: m/z= 1629.6
イオン化モード=MALDI-: m/z= 2902.5
色素合成例1で得られた式(B-I-1a)で表される化合物2.76部、1-プロピルアミン(東京化成工業(株)製)3.3部、トリス(ジベンジリデンアセトン)ジパラジウム(0)(富士フイルム和光純薬(株)製)0.528部、2-ジシクロヘキシルホスフィノ-2’-(ジメチルアミノ)ビフェニル(富士フイルム和光純薬(株)製)0.69部、tert-ブトキシナトリウム1.77部(東京化成工業(株)製)、及び脱水1,2-ジメトキシエタン(関東化学(株)製)54部を混合し、40℃、2時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-4a)で表される化合物を1.68部得た(収率67%)。
(質量分析)イオン化モード=ESI+: m/z= 652.6
色素合成例15で得られた式(B-I-4a)で表される化合物0.82部、1-ブロモナフタレン(東京化成工業(株)製)0.91部、酢酸パラジウム(東京化成工業(株)製)0.052部、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(東京化成工業(株)製)0.24部、tert-ブトキシナトリウム(東京化成工業(株)製)0.59部、及び脱水1,2-ジメトキシエタン(関東化学(株)製)16部を混合し、93℃、10時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-4)で表される化合物を1.2部得た(収率87%)。
(質量分析)イオン化モード=ESI+: m/z= 1030.8
色素合成例4で得られた式(C-I-1)で表される化合物1.36部、色素合成例16で得られた式(B-I-4)で表される化合物0.90部、オキシ塩化リン(富士フイルム和光純薬(株)製)0.52部、及び脱水トルエン(関東化学(株)製)6.8部を混合し、100℃、3時間撹拌した。25℃に冷却後、得られた混合物を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(I-35a-1)で表される化合物を1.36部得た(収率62%)。
(質量分析)イオン化モード=ESI+: m/z= 802.7、3価
色素合成例17で得られた式(I-35a-1)で表される化合物0.69部、ホスホタングステン酸水和物(シグマアルドリッチ(株)製)1.18部、及び脱水ジメチルスルホキシド(関東化学(株)製)3.6部を混合し、45℃、6時間撹拌した。25℃に冷却後、水28部を加え、得られた青色沈殿物を濾過した。得られた残渣を60℃で減圧乾燥したところ、式(I-35a-2)で表される化合物を1.3部得た(収率89%)。
(質量分析)イオン化モード=MALDI+: m/z= 2405.9
イオン化モード=MALDI-: m/z= 2902.5
以下の反応は、窒素雰囲気下で行った。冷却管及び撹拌装置を備えたフラスコに4-ブロモ-3,5-ジメチルフェノール(東京化成工業(株)製)4.6部、炭酸カリウム4.0部およびN,N-ジメチルホルムアミド17.4部を加え、25℃で20分撹拌した後、1,4-ジブロモブタン(東京化成工業(株)製)2.5部を加えて60℃で5時間撹拌した。反応液を放冷した後、蒸留水200部および酢酸エチル200部を加えて分液し、水層を酢酸エチル200部で2回洗浄した。得られた有機層を併せて過剰のNa2SO4で乾燥し、減圧濃縮して粗体を得た。これをシリカゲルカラムクロマトグラフィー(展開相:キサン/トルエン 3/1)で精製した。60℃で減圧乾燥後、式(B-I-5a)で表される化合物を3.7部得た(収率69%)。
(質量分析)イオン化モード=ESI+: m/z= 455.2
色素合成例19で得られた式(B-I-5a)で表される化合物3.95部、1-アミノナフタレン(東京化成工業(株)製)2.48部、トリス(ジベンジリデンアセトン)ジパラジウム(0)1.00部、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル(東京化成工業(株)製)0.71部、tert-ブトキシナトリウム(東京化成工業(株)製)3.74部、及びトルエン40部を混合し、110℃、3時間撹拌した。25℃に冷却後、得られた混合物をセライトろ過し、ろ液を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(B-I-5)で表される化合物を3.5部得た(収率70%)。
(質量分析)イオン化モード=ESI+: m/z= 581.5
2,6-ジメチルアニリン(東京化成工業(株)製)の代わりに2,4,6-トリメチルアニリン(東京化成工業(株)製)を用いた以外は色素合成例3と同様にして、式(C-I-5a)で表される化合物を得た。
式(C-I-1a)で表される化合物の代わりに式(C-I-5a)で表される化合物を用いた以外は色素合成例4と同様にして、式(C-I-5)で表される化合物を得た。
色素合成例22で得られた式(C-I-5)で表される化合物16.5部、色素合成例20で得られた式(B-I-5)で表される化合物7.5部、オキシ塩化リン(富士フイルム和光純薬(株)製)5.9部、及び脱水トルエン(関東化学(株)製)98部を混合し、80℃、3時間撹拌した。25℃に冷却後、得られた混合物を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(I-40a-1)で表される化合物を1.0部得た(収率5%)。
(質量分析)イオン化モード=ESI+: m/z= 777.7、2価
色素合成例23で得られた式(I-40a-1)で表される化合物1.3部、ホスホタングステン酸水和物(シグマアルドリッチ(株)製)3.8部、及び脱水ジメチルスルホキシド(関東化学(株)製)6.6部を混合し、45℃、6時間撹拌した。25℃に冷却後、水80部を加え、得られた青色沈殿物を濾過した。得られた残渣を60℃で減圧乾燥したところ、式(I-40a-2)で表される化合物を1.4部得た(収率61%)。
(質量分析)イオン化モード=MALDI+: m/z= 1553.7
イオン化モード=MALDI-: m/z= 2902.5
2,6-ジメチルアニリン(東京化成工業(株)製)の代わりに2,6-ジメチル-4-メトキシアニリンを用いた以外は色素合成例3と同様にして、式(C-I-6a)で表される化合物を得た。
式(C-I-1a)で表される化合物の代わりに式(C-I-6a)で表される化合物を用いた以外は色素合成例4と同様にして、式(C-I-6)で表される化合物を得た。
色素合成例26で得られた式(C-I-6)で表される化合物4.7部、色素合成例20で得られた式(B-I-5)で表される化合物2.0部、オキシ塩化リン(富士フイルム和光純薬(株)製)1.6部、及び脱水トルエン(関東化学(株)製)6.0部を混合し、80℃、4時間撹拌した。25℃に冷却後、得られた混合物を濃縮した。得られた残渣をシリカゲルカラム精製(溶剤:クロロホルム)し、60℃で減圧乾燥したところ、式(I-42a-1)で表される化合物を0.7部得た(収率10%)。
(質量分析)イオン化モード=ESI+: m/z= 809.7、2価
色素合成例27で得られた式(I-42a-1)で表される化合物0.7部、ホスホタングステン酸水和物(シグマアルドリッチ(株)製)1.8部、及び脱水ジメチルスルホキシド(関東化学(株)製)210部を混合し、45℃、6時間撹拌した。25℃に冷却後、水300部を加え、得られた青色沈殿物を濾過した。得られた残渣を60℃で減圧乾燥したところ、式(I-42a-2)で表される化合物を0.7部得た(収率57%)。
(質量分析)イオン化モード=MALDI+: m/z= 1617.7
イオン化モード=MALDI-: m/z= 2902.5
式(C-I-1)で表される化合物の代わりに式(C-I-5)で表される化合物を用いた以外は色素合成例9と同様にして、式(I-4a-1)で表される化合物を得た。
(質量分析)イオン化モード=MALDI+: m/z= 1601.9
式(I-5a-1)で表される化合物の代わりに式(I-4a-1)で表される化合物を用いた以外は色素合成例10と同様にして、式(I-4a-2)で表される化合物を得た。
(質量分析)イオン化モード=MALDI+: m/z= 1601.9
イオン化モード=MALDI-: m/z= 2902.5
特開2014-108975号公報に記載の内容に従い、下記式(x1)で表される化合物を合成した。
特開2014-108975号公報に記載の内容に従い、下記式(x2)で表される化合物を合成した。
樹脂合成例1
還流冷却器、滴下ロート及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、乳酸エチル141部、プロピレングリコールモノメチルエーテルアセテート178部を入れ、撹拌しながら85℃まで加熱した。次いで、アクリル酸38部、3,4-エポキシトリシクロ[5.2.1.02,6]デカン-8-イルアクリレート及び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)25部、N-シクロヘキシルマレイミド137部、2-ヒドロキシエチルメタクリレート50部、プロピレングリコールモノメチルエーテルアセテート338部の混合溶液を5時間かけて滴下した。一方、2,2-アゾビスイソブチロニトリル5部をプロピレングリコールモノメチルエーテルアセテート88部に溶解した溶液を6時間かけて滴下した。滴下終了後、85℃で4時間保持した後、室温まで冷却して、B型粘度計(23℃)で測定した粘度23mPas、固形分25.6%の共重合体(樹脂B-1)溶液を得た。生成した共重合体の重量平均分子量Mwは8.0×103、分散度2.1、固形分換算の酸価は109mg-KOH/gであった。樹脂B-1は、以下の構造単位を有する。
<化合物(I-23a-2)を含む着色剤分散液(A-1)の調製>
化合物(I-23a-2)5部、アクリル分散剤3部、樹脂B-1(固形分換算)2部、プロピレングリコールモノメチルエーテルアセテート79部、ジアセトンアルコール10部、乳酸エチル1部、および0.2mmのジルコニアビーズ300部を混合し、ペイントコンディショナー(LAU社製)を使用して、得られた混合物を1時間振盪した。その後、ジルコニアビーズをろ過により除去して着色剤分散液(A-1)を得た。
(A)着色剤:着色剤分散液(A-1) 245部
(B)樹脂:樹脂(B-1)(固形分換算) 45部
(C)重合性化合物:ジペンタエリスリトールヘキサアクリレート
(カヤラッド(登録商標)DPHA;日本化薬(株)製) 50部
(D)重合開始剤:TR-PBG327(常州強力電子新材料社製) 3部
(F)界面活性剤:フッ素系界面活性剤(メガファック(登録商標)F554;DIC社製 0.09部
(E)溶剤:プロピレングリコールモノメチルエーテルアセテート(E-1) 506部
(E)溶剤:乳酸エチル(E-2) 27部
を混合して着色樹脂組成物を得た。
化合物(I-23a-2)を以下の化合物に変更したこと以外は、実施例1と同様に着色樹脂組成物を各々得た。
実施例2:化合物(I-5a-2)
実施例3:化合物(I-17a-2)
実施例4:化合物(I-35a-2)
実施例5:化合物(I-40a-2)
実施例6:化合物(I-42a-2)
実施例7:化合物(I-4a-2)
比較例1:化合物(x1)
比較例2:化合物(x2)
(赤色樹脂組成物の作製)
(A)着色剤:Acid Red 52(東京化成工業(株)製) 8部
(B)樹脂:樹脂(B-1)(固形分換算) 50部
(C)重合性化合物:ジペンタエリスリトールヘキサアクリレート
(カヤラッド(登録商標)DPHA;日本化薬(株)製) 50部
(D)重合開始剤:TR-PBG327(常州強力電子新材料社製)3部
(F)界面活性剤:フッ素系界面活性剤(メガファック(登録商標)F554;DIC社製) 0.09部
(E)溶剤:プロピレングリコールモノメチルエーテルアセテート(E-1) 127部
(E)溶剤:乳酸エチル(E-2) 30部
(E)溶剤:4-ヒドロキシ-4-メチル-2-ペンタノン(E-3) 472部
を混合して赤色樹脂組成物を得た。
2インチ角のガラス基板(イーグル2000;コーニング社製)上に、実施例1~7及び比較例1~2で得られた着色樹脂組成物、並びに作製例1で得られた赤色樹脂組成物をそれぞれスピンコート法で塗布した後、100℃で3分間プリベークして、組成物層を形成した。冷却後、露光機(TME-150RSK;トプコン社製)を用いて、大気雰囲気下、60mJ/cm2の露光量(365nm基準)で組成物層に光照射した後、オーブン中、230℃で20分間ポストベークを行うことにより、着色塗膜を得た。
オリンパス社製の測色機(OSP-SP-200)装置を用いて、上記実施例1~7、比較例1~2、並びに作製例1から得られた着色塗膜の透過スペクトルを各々測定した。
実施例1~7又は比較例1~2の着色樹脂組成物と、作製例1の赤色樹脂組成物とを表10の比率で混合したときのCIE色度座標と明度Yを求めた。CIE色度座標と明度Yは、実施例1~7及び比較例1~2の着色塗膜から各々得られた透過スペクトルと、作製例1の着色塗膜から得られた透過スペクトルと、C光源の特性関数とを用いて計算され、表10の混合比率はいずれもCIE色度座標(x,y)=(0.150,0.060)となる組み合わせであった。明度Yの値を表10に示す。Yの値が大きいほど明度が高いことを示す。
I-23a-2:化合物(I-23a-2)
I-5a-2 :化合物(I-5a-2)
I-17a-2:化合物(I-17a-2)
I-35a-2:化合物(I-35a-2)
I-40a-2:化合物(I-40a-2)
I-42a-2:化合物(I-42a-2)
I-4a-2 :化合物(I-4a-2)
x1 :化合物(x1)
x2 :化合物(x2)
AR52 :Acid Red 52
Claims (5)
- 式(I)で表される化合物。
[式(I)中、
R1~R4及びR13は、互いに独立に、水素原子又は置換基を有していてもよい炭素数1~10の炭化水素基を表す。
R5~R12は、互いに独立に、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数1~5の炭化水素基を表す。
T1及びT2は、互いに独立に、置換基を有していてもよい2価の芳香族炭化水素基又は置換基を有していてもよい2価の芳香族複素環基を表す。
L1は、置換基を有していてもよい炭素数1~12のa価の脂肪族炭化水素基又は式(i)で表される基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
aは、2以上の整数を表す。
b及びcは、互いに独立に、1以上の整数を表す。
dは、0以上の整数を表す。
Xc-は、c価のアニオンを表す。]
[式(i)中、
T3は、置換基を有していてもよいa価の芳香族炭化水素基又は置換基を有していてもよいa価の芳香族複素環基を表す。
L2は、置換基を有していてもよい炭素数1~5の2価の脂肪族炭化水素基を表し、該脂肪族炭化水素基に含まれるメチレン基の少なくとも1つは-O-で置き換わっている。
*はT2との結合手を表す。] - 着色剤及び樹脂を含有し、前記着色剤が請求項1に記載の化合物を含む着色樹脂組成物。
- さらに重合性化合物及び重合開始剤を含有する請求項2に記載の着色樹脂組成物。
- 請求項2又は3に記載の着色樹脂組成物から形成されるカラーフィルタ。
- 請求項4に記載のカラーフィルタを含む表示装置。
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JP2014108975A (ja) * | 2012-11-30 | 2014-06-12 | Dainippon Printing Co Ltd | 色材、色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置 |
JP2015034966A (ja) * | 2013-07-09 | 2015-02-19 | 富士フイルム株式会社 | 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、および画像表示装置 |
JP2016088894A (ja) * | 2014-11-06 | 2016-05-23 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 化合物 |
JP2017165808A (ja) * | 2016-03-14 | 2017-09-21 | 富士フイルム株式会社 | 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置および化合物 |
JP2018003013A (ja) * | 2016-06-28 | 2018-01-11 | 大日本印刷株式会社 | 色材分散液、着色樹脂組成物、カラーフィルター、液晶表示装置、及び、発光表示装置 |
JP2018162364A (ja) * | 2017-03-24 | 2018-10-18 | 三菱ケミカル株式会社 | 着色樹脂組成物、カラーフィルタ及び画像表示装置 |
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JP2014108975A (ja) * | 2012-11-30 | 2014-06-12 | Dainippon Printing Co Ltd | 色材、色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置 |
JP2015034966A (ja) * | 2013-07-09 | 2015-02-19 | 富士フイルム株式会社 | 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、および画像表示装置 |
JP2016088894A (ja) * | 2014-11-06 | 2016-05-23 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 化合物 |
JP2017165808A (ja) * | 2016-03-14 | 2017-09-21 | 富士フイルム株式会社 | 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、画像表示装置および化合物 |
JP2018003013A (ja) * | 2016-06-28 | 2018-01-11 | 大日本印刷株式会社 | 色材分散液、着色樹脂組成物、カラーフィルター、液晶表示装置、及び、発光表示装置 |
JP2018162364A (ja) * | 2017-03-24 | 2018-10-18 | 三菱ケミカル株式会社 | 着色樹脂組成物、カラーフィルタ及び画像表示装置 |
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