JP2009108135A - Green dispersion, alkali-soluble green photosensitive composition, and method for producing those - Google Patents
Green dispersion, alkali-soluble green photosensitive composition, and method for producing those Download PDFInfo
- Publication number
- JP2009108135A JP2009108135A JP2007279284A JP2007279284A JP2009108135A JP 2009108135 A JP2009108135 A JP 2009108135A JP 2007279284 A JP2007279284 A JP 2007279284A JP 2007279284 A JP2007279284 A JP 2007279284A JP 2009108135 A JP2009108135 A JP 2009108135A
- Authority
- JP
- Japan
- Prior art keywords
- dispersion
- green
- meth
- acrylate
- alkali
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 115
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000000049 pigment Substances 0.000 claims abstract description 54
- 239000002245 particle Substances 0.000 claims abstract description 46
- -1 azo compound Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 19
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 18
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 9
- 150000003751 zinc Chemical class 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 101
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 239000002612 dispersion medium Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000001384 succinic acid Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 239000001056 green pigment Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical class OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- VTRZMLZNHGCYLK-UHFFFAOYSA-N 1-ethenyl-2-(methoxymethyl)benzene Chemical compound COCC1=CC=CC=C1C=C VTRZMLZNHGCYLK-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- HDEWQSUXJCDXIX-UHFFFAOYSA-N 1-ethenyl-3-(methoxymethyl)benzene Chemical compound COCC1=CC=CC(C=C)=C1 HDEWQSUXJCDXIX-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- XVXKXOPCFWAOLN-UHFFFAOYSA-N 1-ethenyl-4-(methoxymethyl)benzene Chemical compound COCC1=CC=C(C=C)C=C1 XVXKXOPCFWAOLN-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JFWFAUHHNYTWOO-UHFFFAOYSA-N 2-[(2-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC=C1COCC1OC1 JFWFAUHHNYTWOO-UHFFFAOYSA-N 0.000 description 1
- OCKQMFDZQUFKRD-UHFFFAOYSA-N 2-[(3-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC(COCC2OC2)=C1 OCKQMFDZQUFKRD-UHFFFAOYSA-N 0.000 description 1
- ZADXFVHUPXKZBJ-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methoxymethyl]oxirane Chemical compound C1=CC(C=C)=CC=C1COCC1OC1 ZADXFVHUPXKZBJ-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical compound NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- XBHQOMRKOUANQQ-UHFFFAOYSA-N 2-ethoxypropanoic acid Chemical compound CCOC(C)C(O)=O XBHQOMRKOUANQQ-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical compound COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- GCXJINGJZAOJHR-UHFFFAOYSA-N 2-methylacetoacetic acid Chemical compound CC(=O)C(C)C(O)=O GCXJINGJZAOJHR-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101000928724 Pseudomonas putida 4-cresol dehydrogenase [hydroxylating] flavoprotein subunit Proteins 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- URBZEXMYYYABCQ-UHFFFAOYSA-N butyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCCC URBZEXMYYYABCQ-UHFFFAOYSA-N 0.000 description 1
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
- IWPATTDMSUYMJV-UHFFFAOYSA-N butyl 2-methoxyacetate Chemical compound CCCCOC(=O)COC IWPATTDMSUYMJV-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SVBSJWKYFYUHTF-UHFFFAOYSA-N ethyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCC SVBSJWKYFYUHTF-UHFFFAOYSA-N 0.000 description 1
- WNIHNYUROPJCLW-UHFFFAOYSA-N ethyl 2-ethoxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OCC WNIHNYUROPJCLW-UHFFFAOYSA-N 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- JRJLLXQDXANQEC-UHFFFAOYSA-N fastogen green y Chemical compound [Cu+2].[N-]1C(N=C2C3=C(Cl)C(Cl)=C(Br)C(Cl)=C3C(N=C3C4=C(Br)C(Cl)=C(Br)C(Cl)=C4C(=N4)[N-]3)=N2)=C(C(Br)=C(Cl)C(Br)=C2Cl)C2=C1N=C1C2=C(Cl)C(Cl)=C(Cl)C(Br)=C2C4=N1 JRJLLXQDXANQEC-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- JQAACYUZYRBHGG-UHFFFAOYSA-L magnesium pidolate Chemical compound [Mg+2].[O-]C(=O)C1CCC(=O)N1.[O-]C(=O)C1CCC(=O)N1 JQAACYUZYRBHGG-UHFFFAOYSA-L 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BKFQHFFZHGUTEZ-UHFFFAOYSA-N methyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OC BKFQHFFZHGUTEZ-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-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
- 229940057867 methyl lactate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-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
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 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
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-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
- 150000003014 phosphoric acid esters Chemical class 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
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LVDAGIFABMFXSJ-UHFFFAOYSA-N propyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCC LVDAGIFABMFXSJ-UHFFFAOYSA-N 0.000 description 1
- NORCOOJYTVHQCR-UHFFFAOYSA-N propyl 2-hydroxyacetate Chemical compound CCCOC(=O)CO NORCOOJYTVHQCR-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 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
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Optical Filters (AREA)
Abstract
Description
本発明は、緑色分散液及びアルカリ可溶型緑色感光性組成物に関し、特に、カラーフィルター作製に有用なアルカリ可溶型緑色感光性組成物に関する。更に、それらの製造方法に関する。 The present invention relates to a green dispersion and an alkali-soluble green photosensitive composition, and more particularly to an alkali-soluble green photosensitive composition useful for producing a color filter. Furthermore, it is related with those manufacturing methods.
液晶表示装置に用いられるカラーフィルターは、ガラス等の透明基板上に赤色(R)、緑色(G)、青色(B)の各着色層が形成されたものである。これら各着色層は、いずれも有機顔料を分散した合成樹脂の薄膜が基板上に設けられた構造であり、その有機顔料としては、赤、緑及び青色の顔料が使用されている。
上記着色層を形成するためのカラーフィルター用感光性組成物は、有機顔料と有機溶媒と必要に応じて分散剤とを混合し均一となるように攪拌分散して顔料分散液を調製し、次いでこれに光硬化性化合物と、必要に応じて熱可塑性樹脂や光重合開始剤等を加えることで調製されている。
A color filter used in a liquid crystal display device is one in which colored layers of red (R), green (G), and blue (B) are formed on a transparent substrate such as glass. Each of these colored layers has a structure in which a thin film of a synthetic resin in which an organic pigment is dispersed is provided on a substrate, and red, green, and blue pigments are used as the organic pigment.
The photosensitive composition for a color filter for forming the colored layer is prepared by mixing an organic pigment, an organic solvent, and a dispersant as necessary, stirring and dispersing the mixture so as to be uniform, and then preparing a pigment dispersion. It is prepared by adding a photocurable compound and, if necessary, a thermoplastic resin, a photopolymerization initiator or the like to this.
従来から、上述のカラーフィルター用感光性組成物に用いられている緑色顔料は、中心金属が銅である「ピグメント グリーン 36」が主に使用されているが、微細な粒径の顔料を用いることにより、得られる塗膜のコントラストは良化するが、着色層を高輝度にすることや感光性組成物の分散安定性を得ることは困難であった。
例えば、特許文献1では、一次粒子の平均粒子径が0.01〜0.1μm、且つ一次粒子のアスペクトが1〜2であるハロゲン化金属フタロシアニンを用い、塗膜のコントラストに優れるカラーフィルターが得られる緑色顔料組成物を提案している。しかし、緑色顔料の1次粒子の粒径が小さいため、顔料分散液の安定性を得ることが困難であった。
Conventionally, “Pigment Green 36” whose central metal is copper is mainly used as the green pigment used in the above-described photosensitive composition for color filters. However, a pigment having a fine particle size is used. As a result, the contrast of the resulting coating film is improved, but it has been difficult to increase the brightness of the colored layer and to obtain the dispersion stability of the photosensitive composition.
For example, Patent Document 1 uses a metal halide phthalocyanine having an average primary particle diameter of 0.01 to 0.1 μm and an aspect ratio of primary particles of 1 to 2 to obtain a color filter having excellent coating film contrast. A green pigment composition is proposed. However, since the primary particle size of the green pigment is small, it is difficult to obtain the stability of the pigment dispersion.
一方、特許文献2では、平均粒子径が1μm以下の着色化合物と、硬化性化合物とが分散媒に分散された液状予備分散組成物を調製する予備分散工程と、その予備分散工程で得られた液状予備分散組成物を、100kg/cm2以上の圧力下で高圧分散処理する高圧分散工程とからなる着色組成物の製造方法が提案されている。ここでは、フタロシアニングリーン(C.I. Pigment Green 7:ハロゲン化銅フタロシアニン顔料)、ジアントラキノリルレッド(C.I. Pigment Red 177:赤色顔料)やフタロシアニンブルー(C.I. Pigment Blue 15:6青色顔料)の高圧衝突分散が例示されている。しかしながら、用いるハロゲン化銅フタロシアニン顔料等の平均粒径が非常に大きいので分散液の分散性や分散安定性は良好であるが、輝度及びコントラストが低かった。 On the other hand, in Patent Document 2, a preliminary dispersion step of preparing a liquid preliminary dispersion composition in which a coloring compound having an average particle diameter of 1 μm or less and a curable compound are dispersed in a dispersion medium, and the preliminary dispersion step were obtained. There has been proposed a method for producing a colored composition comprising a high-pressure dispersion process in which a liquid pre-dispersion composition is subjected to a high-pressure dispersion treatment under a pressure of 100 kg / cm 2 or more. Here, phthalocyanine green (CI Pigment Green 7: halogenated copper phthalocyanine pigment), dianthraquinolyl red (CI Pigment Red 177: red pigment) and phthalocyanine blue (C.I. Pigment Blue 15: 6). The high-pressure collision dispersion of the blue pigment) is illustrated. However, since the average particle diameter of the halogenated copper phthalocyanine pigment used is very large, the dispersibility and dispersion stability of the dispersion are good, but the brightness and contrast are low.
本発明は、このような状況下で、高輝度且つ高コントラストのカラーフィルターの緑色着色層を形成し得る、分散安定性の良好な分散性緑色分散液及びアルカリ可溶型緑色感光性組成物を提供することを課題とする。更に、高輝度且つ高コントラストの緑色着色層を有するカラーフィルター提供することを課題とする。 Under such circumstances, the present invention provides a dispersible green dispersion and an alkali-soluble green photosensitive composition with good dispersion stability, which can form a green colored layer of a color filter with high brightness and high contrast. The issue is to provide. It is another object of the present invention to provide a color filter having a green colored layer with high brightness and high contrast.
本発明者は、前記課題を達成するために鋭意研究を重ねた結果、特定の顔料成分を用いた予備分散液を高圧衝突分散させることにより上記課題を達成し得ることを見出した。本発明は、かかる知見に基づいて完成したものである。
すなわち、本発明は、
(1)ハロゲン化亜鉛フタロシアニン顔料(A)とアゾ化合物のニッケル錯体顔料(B)と有機溶媒とを混合してなり且つ分散粒子の平均粒径が10〜100nmである予備分散液を、50MPa〜300MPaの圧力下で高圧衝突分散させることにより得られる緑色分散液、
(2)前記ハロゲン化亜鉛フタロシアニン顔料(A)のハロゲン原子が、臭素原子及び/又は塩素原子である上記(1)の緑色分散液、
(3)上記(1)又は(2)の緑色分散液と、アルカリ可溶性樹脂と、光重合性モノマーと、光重合開始剤とを含有してなるアルカリ可溶型緑色感光性組成物、
(4)上記(3)に記載のアルカリ可溶型緑色感光性組成物を硬化させて得た緑色着色層を有するカラーフィルター、
(5)ハロゲン化亜鉛フタロシアニン顔料(A)とアゾ化合物のニッケル錯体顔料(B)と有機溶媒とを混合して、分散粒子の平均粒径が10〜100nmである予備分散液を調製する工程(a)と、該予備分散液を50MPa〜300MPaの圧力下で高圧衝突分散させる工程(b)とを含む緑色分散液の製造方法、
(6)前記ハロゲン化亜鉛フタロシアニン顔料(A)のハロゲン原子が、臭素原子及び/又は塩素原子である上記(5)緑色分散液の製造方法、及び
(7)上記(5)又は(6)の方法により得られた緑色分散液と、アルカリ可溶性樹脂と、光重合性モノマーと、光重合開始剤とを混合する工程を含むアルカリ可溶型緑色感光性組成物の製造方法である。
As a result of intensive studies in order to achieve the above object, the present inventor has found that the above object can be achieved by high-pressure collision dispersion of a preliminary dispersion using a specific pigment component. The present invention has been completed based on such findings.
That is, the present invention
(1) A preliminary dispersion liquid obtained by mixing a halogenated zinc phthalocyanine pigment (A), a nickel complex pigment (B) of an azo compound, and an organic solvent, and having an average particle diameter of dispersed particles of 10 to 100 nm, A green dispersion obtained by high-pressure collision dispersion under a pressure of 300 MPa,
(2) The green dispersion liquid according to (1), wherein the halogen atom of the zinc halide phthalocyanine pigment (A) is a bromine atom and / or a chlorine atom,
(3) An alkali-soluble green photosensitive composition comprising the green dispersion of (1) or (2), an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator,
(4) A color filter having a green colored layer obtained by curing the alkali-soluble green photosensitive composition according to (3) above,
(5) A step of preparing a preliminary dispersion in which the average particle diameter of dispersed particles is 10 to 100 nm by mixing a halogenated zinc phthalocyanine pigment (A), a nickel complex pigment (B) of an azo compound, and an organic solvent ( a method of producing a green dispersion comprising a) and a step (b) of high-pressure collision dispersion of the preliminary dispersion under a pressure of 50 MPa to 300 MPa,
(6) The method (5) for producing a green dispersion, wherein the halogen atom of the zinc halide phthalocyanine pigment (A) is a bromine atom and / or a chlorine atom, and (7) the method according to (5) or (6) It is a manufacturing method of the alkali-soluble green photosensitive composition including the process of mixing the green dispersion liquid obtained by the method, alkali-soluble resin, a photopolymerizable monomer, and a photoinitiator.
本発明によれば、高輝度且つ高コントラストのカラーフィルターの緑色着色層を形成し得る、分散安定性の良好な分散性緑色分散液及びアルカリ可溶型緑色感光性組成物を提供することができる。更に、高輝度且つ高コントラストの緑色着色層を有するカラーフィルターを提供することができる。 According to the present invention, it is possible to provide a dispersible green dispersion and an alkali-soluble green photosensitive composition with good dispersion stability, which can form a green colored layer of a color filter with high brightness and high contrast. . Furthermore, it is possible to provide a color filter having a green coloring layer with high brightness and high contrast.
本発明は、ハロゲン化亜鉛フタロシアニン顔料(A)とアゾ化合物のニッケル錯体顔料(B)と有機溶媒とを混合してなり且つ分散粒子の平均粒径が10〜100nmである予備分散液を、高圧衝突分散させることにより得られる緑色分散液であり、50MPa〜300MPaの圧力下で高圧衝突分散させるものである。
本発明に係る予備分散液の分散粒子の平均粒径が10nm以下では、予備分散液の粘度が高くなり、高圧分散工程における作業性が低下する恐れがあるとともに、高圧分散後の顔料粒径が細かくなりすぎるために分散安定性が悪くなる可能性があり、100nm以上では高圧分散工程後の顔料粒径が十分に細かくならず、輝度、コントラストが不十分となる。
また、高圧衝突分散の圧力が50MPa未満では、分散効率が不十分であり、本発明の目的を達成し得なく、300MPaを超えると装置の耐久性に問題を発生し易くなる。この観点から80MPa〜250MPaがより好ましく、100MPa〜200MPaが特に好ましい。
The present invention relates to a pre-dispersion liquid obtained by mixing a halogenated zinc phthalocyanine pigment (A), a nickel complex pigment (B) of an azo compound, and an organic solvent, and having an average particle diameter of dispersed particles of 10 to 100 nm. It is a green dispersion liquid obtained by collision-dispersion, and is subjected to high-pressure collision dispersion under a pressure of 50 MPa to 300 MPa.
When the average particle size of the dispersed particles of the preliminary dispersion according to the present invention is 10 nm or less, the viscosity of the preliminary dispersion is increased, and the workability in the high-pressure dispersion process may be reduced. Since the dispersion becomes too fine, dispersion stability may be deteriorated. When the particle diameter is 100 nm or more, the pigment particle size after the high-pressure dispersion step is not sufficiently fine, and the brightness and contrast are insufficient.
Further, if the pressure of high-pressure collision dispersion is less than 50 MPa, the dispersion efficiency is insufficient, and the object of the present invention cannot be achieved, and if it exceeds 300 MPa, a problem tends to occur in the durability of the apparatus. From this viewpoint, 80 MPa to 250 MPa is more preferable, and 100 MPa to 200 MPa is particularly preferable.
本発明において、ハロゲン化亜鉛フタロシアニン顔料(A)は、下記一般式(I)で表される、中心金属が亜鉛であるハロゲン化亜鉛フタロシアニン顔料である。 In the present invention, the halogenated zinc phthalocyanine pigment (A) is a zinc halide phthalocyanine pigment represented by the following general formula (I) whose central metal is zinc.
従って、上記一般式(I)から明らかなように、4個のベンゼン環に結合する16個のハロゲン原子又は水素原子のうち、8〜15個はフッ素原子、塩素原子、臭素原子、ヨウ素原子のいずれかのハロゲン原子であり、残りは水素原子である。
ここで、Xで表わされるハロゲン原子としては、臭素原子及び/又は塩素原子が好ましい。緑色としての着色力に優れ、青味がすぎないからである。
Therefore, as is apparent from the above general formula (I), 8 to 15 out of 16 halogen atoms or hydrogen atoms bonded to the four benzene rings are fluorine atoms, chlorine atoms, bromine atoms, iodine atoms. Any halogen atom and the rest are hydrogen atoms.
Here, the halogen atom represented by X is preferably a bromine atom and / or a chlorine atom. It is because it is excellent in coloring power as green and is not too bluish.
また、アゾ化合物のニッケル錯体顔料(B)は、ニッケル−アゾ錯体系顔料ともいい、具体的には、ランクセス(株)社製、Gelb pigment E4GN−GT 等が好ましい。 Moreover, the nickel complex pigment (B) of an azo compound is also called a nickel-azo complex pigment, and specifically, Gelb pigment E4GN-GT manufactured by LANXESS, Inc. is preferable.
本発明の緑色分散液に用いられる有機溶媒としては、上記の顔料及び所望により配合される分散剤を均一に分散でき、且つ後述するアルカリ可溶性樹脂、光重合性モノマー、光重合開始剤及び着色剤を均一に溶解分散できるエステル類、エーテル類、ケトン類等が挙げられ、これらは単独で用いても、2種以上を混合して使用しても良い。 As the organic solvent used in the green dispersion of the present invention, the above-mentioned pigment and a dispersant to be blended as desired can be uniformly dispersed, and an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, and a colorant described later are used. Are esters, ethers, ketones, etc. that can be uniformly dissolved and dispersed. These may be used alone or in admixture of two or more.
上記のエステル類としては、例えば、酢酸エチル、酢酸−n−ブチル、酢酸イソブチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、酢酸アミル、プロピオン酸エチル、プロピオン酸プロピル、プロピオン酸ブチル、酪酸メチル、酪酸エチル、酪酸プロピル、酪酸ブチル等のアルキルエステル類;乳酸メチル、乳酸エチル、ヒドロキシ酢酸メチル、ヒドロキシ酢酸エチル、ヒドロキシ酢酸プロピル、ヒドロキシ酢酸ブチル、メトキシ酢酸メチル、メトキシ酢酸エチル、メトキシ酢酸プロピル、メトキシ酢酸ブチル、エトキシ酢酸メチル、エトキシ酢酸エチル、エトキシ酢酸プロピル、ブトキシ酢酸メチル、ブトキシ酢酸エチル、ブトキシ酢酸プロピル、ブトキシ酢酸ブチル、3−ヒドロキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、3−メトキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、3−エトキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、2−ヒドロキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、2−メトキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、2−エトキシプロピオン酸のメチル、エチル、プロピル、ブチル等のエステル類、2−ヒドロキシ−2−メチルプロピオン酸メチル、2−ヒドロキシ−2−メチルプロピオン酸エチル、2−メトキシ−2−メチルプロピオン酸メチル、2−エトキシ−2−メチルプロピオン酸エチル、ピルビン酸のメチル、エチル、プロピル等のエステル類、アセト酢酸のメチル、エチル等のエステル類、2−オキソブタン酸のメチル、エチルのエステル類等、及びこれらの混合物が挙げられる。 Examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, amyl acetate, ethyl propionate, propyl propionate, and propionic acid. Alkyl esters such as butyl, methyl butyrate, ethyl butyrate, propyl butyrate and butyl butyrate; methyl lactate, ethyl lactate, methyl hydroxyacetate, ethyl hydroxyacetate, propyl hydroxyacetate, butyl hydroxyacetate, methyl methoxyacetate, ethyl methoxyacetate, methoxy Of propyl acetate, butyl methoxyacetate, methyl ethoxy acetate, ethyl ethoxy acetate, propyl ethoxy acetate, methyl butoxyacetate, ethyl butoxyacetate, propyl butoxyacetate, butylbutoxyacetate, 3-hydroxypropionic acid Esters such as methyl, ethyl, propyl, and butyl; esters of methyl 3-methoxypropionate such as methyl, ethyl, propyl, and butyl; esters of methyl 3-ethoxypropionate such as methyl, ethyl, propyl, and butyl; Esters such as methyl, ethyl, propyl and butyl of hydroxypropionic acid, esters of methyl, ethyl, propyl and butyl of 2-methoxypropionic acid, esters of methyl, ethyl, propyl and butyl of 2-ethoxypropionic acid , Methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate , Esters of ethyl, propyl, etc. Le, esters such as ethyl, 2-methyl-oxobutanoic acid, esters such as ethyl, etc., and mixtures thereof.
上記のエーテル類としては、例えば、ジエチレングリコールジメチルエーテル、テトラヒドロフラン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート等、及びこれらの混合物が挙げられる。
上記のケトン類としては、例えば、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、2−ヘプタノン、3−ヘプタノン等、及びこれらの混合物が挙げられる。その他、必要に応じてトルエン、キシレン等の芳香族炭化水素類も使用することができる。
Examples of the ethers include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate , And mixtures thereof.
Examples of the ketones include methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone, and mixtures thereof. In addition, aromatic hydrocarbons such as toluene and xylene can be used as necessary.
上述の有機溶媒の内、エチレングリコールモノエチルエーテル(沸点:136℃)、エチレングリコールモノメチルエーテルアセテート(沸点:145℃)、プロピレングリコールモノメチルエーテルアセテート(沸点:146℃)、ジエチレングリコールジメチルエーテル(沸点:162℃)、3−メトキシブチルアセテート(沸点:171℃)及び3−メチル−3−メトキシブチルアセテート(沸点:188℃)が特に好ましい。 Among the above organic solvents, ethylene glycol monoethyl ether (boiling point: 136 ° C.), ethylene glycol monomethyl ether acetate (boiling point: 145 ° C.), propylene glycol monomethyl ether acetate (boiling point: 146 ° C.), diethylene glycol dimethyl ether (boiling point: 162 ° C.) ), 3-methoxybutyl acetate (boiling point: 171 ° C.) and 3-methyl-3-methoxybutyl acetate (boiling point: 188 ° C.).
また、本発明の緑色分散液には、所望により公知の分散剤が用いられる。具体的には、変性ポリウレタン,変性ポリアクリレート、変性ポリエステル、変性ポリアミド等の高分子分散剤.リン酸エステル、アルキルアミン、ポリオキシエチレンアルキルフェニルエーテル等の界面活性剤や顔料誘導体を挙げることができる。本発明においては、これらの中でも、高分子分散剤が好ましく、具体的な商品名としてはEFKA−4046、EFKA−4047、EFKAポリマー100、EFKAポリマー400、EFKAポリマー401、EFKAポリマー4300、EFKAポリマー4330(以上、エフカケミカルズ社製)、Disperbyk111、Disperbyk161、Disperbyk165、Disperbyk182、Disperbyk2000、Disperbyk2001(以上、ビックケミー社製)、SOLSPERSE24000、SOLSPERSE27000、SOLSPERSE28000(以上、ルーブリゾール社製)、アジスパー821(味の素ファインテクノ(株)製)等を挙げることができる。 Moreover, a well-known dispersing agent is used for the green dispersion liquid of this invention depending on necessity. Specifically, polymer dispersants such as modified polyurethane, modified polyacrylate, modified polyester, and modified polyamide. Surfactants and pigment derivatives such as phosphate esters, alkylamines, and polyoxyethylene alkylphenyl ethers can be mentioned. Among these, a polymer dispersant is preferable in the present invention, and specific product names include EFKA-4046, EFKA-4047, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 4300, and EFKA polymer 4330. (Above, manufactured by Efka Chemicals), Disperbyk111, Disperbyk161, Disperbyk165, Disperbyk182, Disperbyk2000, Disperbyk2001 (above, manufactured by BYK Chemie), SOLSPERSE24000, SOLSPERSE27000, SOLSPERSE28000 (above, made by LubrizolTechnology), Ajispurintechno 821 And the like).
次に、本発明の緑色分散液の製造方法について工程(a)、工程(b)、工程(c)と工程順に説明する。
1.工程(a)
ハロゲン化亜鉛フタロシアニン顔料(A)(以下、単に「顔料(A)」ということがある)と、アゾ化合物のニッケル錯体顔料(B)(以下、単に「顔料(B)」ということがある)と、有機溶媒と、所望により分散剤とをディゾルバー等の高速高剪断ミキサー中で通常、0.5〜6時間混合して予備分散液を調製する。予備分散液は顔料100質量部当たり、分散剤2〜200質量部、有機溶媒100〜4,000質量部であることが分散性の観点から好ましい。
顔料総量の内の質量比{顔料(A)/顔料(B)}は所望する色調により適宜配合すれば良いが、通常、(9/1)〜(4/6)の範囲で配合される。
また、予備分散液は高速高剪断ミキサーにて混合後、顔料粒子を微粒子化し得る分散メディアを湿式分散機に入れて、この湿式分散機中で更に分散処理することが好ましい。湿式分散機は連続式、バッチ式のいずれでもよいが、工業上の大量生産のためには連続式が好ましい。使用する分散メディアは直径0.03〜2mm程度の各種ビーズ(ジルコニア、ガラス、アルミナ、チタニア等)が用いられる。湿式分散機としては、浅田鉄工(株)製ピコグレンミル、寿工業(株)製ウルトラアペックスミル、(株)井上製作所製キーミル等が挙げられる。
2.工程(b)
次に、工程(a)で得られた緑色分散液の予備分散液を50MPa〜300MPaの圧力下で高圧衝突分散させる。この分散処理は前記の高圧下、高速で液−液衝突させることができる高圧分散機を用いて行われる。高圧分散機としては、例えば、アルティマイザー{(株)スギノマシン製}等が挙げられる。
3.工程(c)
工程(b)で得られた緑色分散液と、アルカリ可溶性樹脂と、光重合性モノマーと、光重合開始剤とを混合してアルカリ可溶型緑色感光性組成物(以下、単に「感光性組成物」ということがある)を製造する。工程(c)における混合は、公知の混合機、分散機、例えば、ビーズミル、ボールミル、ディゾルバー、ニーダー等により混合分散すれば良い。得られた感光性樹脂組成物は好ましくは濾過して調製する。
Next, the manufacturing method of the green dispersion liquid of this invention is demonstrated in order of a process (a), a process (b), and a process (c).
1. Step (a)
A zinc halide phthalocyanine pigment (A) (hereinafter sometimes simply referred to as “pigment (A)”), a nickel complex pigment (B) of an azo compound (hereinafter sometimes simply referred to as “pigment (B)”), The organic solvent and, if desired, the dispersant are usually mixed in a high-speed high shear mixer such as a dissolver for 0.5 to 6 hours to prepare a preliminary dispersion. From the viewpoint of dispersibility, the preliminary dispersion is preferably 2 to 200 parts by weight of a dispersant and 100 to 4,000 parts by weight of an organic solvent per 100 parts by weight of the pigment.
The mass ratio {pigment (A) / pigment (B)} in the total amount of pigment may be appropriately blended depending on the desired color tone, but is usually blended in the range of (9/1) to (4/6).
The preliminary dispersion is preferably mixed with a high-speed high shear mixer, and then a dispersion medium capable of turning the pigment particles into fine particles is placed in a wet disperser and further dispersed in the wet disperser. The wet disperser may be either a continuous type or a batch type, but a continuous type is preferred for industrial mass production. As the dispersion medium to be used, various beads (zirconia, glass, alumina, titania, etc.) having a diameter of about 0.03 to 2 mm are used. Examples of the wet disperser include a Pico Glen Mill manufactured by Asada Tekko Co., Ltd., an Ultra Apex Mill manufactured by Kotobuki Industries Co., Ltd., and a key mill manufactured by Inoue Manufacturing Co., Ltd.
2. Step (b)
Next, the preliminary dispersion liquid of the green dispersion liquid obtained in the step (a) is subjected to high-pressure collision dispersion under a pressure of 50 MPa to 300 MPa. This dispersion treatment is performed using the high-pressure disperser capable of causing liquid-liquid collision at high speed under the above-described high pressure. Examples of the high-pressure disperser include an optimizer {manufactured by Sugino Machine Co., Ltd.}.
3. Step (c)
The green dispersion obtained in the step (b), an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator are mixed to obtain an alkali-soluble green photosensitive composition (hereinafter simply referred to as “photosensitive composition”). Manufacturing). The mixing in the step (c) may be performed by mixing and dispersing using a known mixer or disperser, for example, a bead mill, a ball mill, a dissolver, or a kneader. The obtained photosensitive resin composition is preferably prepared by filtration.
本発明の感光性組成物に配合されるアルカリ可溶性樹脂としては、顔料に対してバインダーとして作用し、かつカラーフィルタを製造する際に、その現像処理工程において用いられる現像液、特に好ましくはアルカリ性現像液に対して可溶性を有するものであれば、特に限定されるものではないが、カルボキシル基を有するアルカリ可溶性樹脂が好ましく、特に、1個以上のカルボキシル基を有するエチレン性不飽和単量体(以下、「カルボキシル基含有不飽和単量体」という)と他の共重合可能なエチレン性不飽和単量体(以下、「共重合性不飽和単量体」という)との共重合体(以下、「カルボキシル基含有共重合体」という)が好ましい。 The alkali-soluble resin to be blended in the photosensitive composition of the present invention acts as a binder for the pigment and is used in a developing process for producing a color filter, particularly preferably an alkaline development. Although it will not specifically limit if it has solubility with respect to a liquid, The alkali-soluble resin which has a carboxyl group is preferable, and especially the ethylenically unsaturated monomer which has one or more carboxyl groups (following) , “Carboxyl group-containing unsaturated monomer”) and other copolymerizable ethylenically unsaturated monomer (hereinafter referred to as “copolymerizable unsaturated monomer”) (Referred to as “carboxyl group-containing copolymer”).
カルボキシル基含有不飽和単量体としては、例えば、(メタ)アクリル酸、クロトン酸、α−クロルアクリル酸、けい皮酸等の不飽和モノカルボン酸類;マレイン酸、無水マレイン酸、フマル酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、メサコン酸等の不飽和ジカルボン酸又はその無水物類;3価以上の不飽和多価カルボン酸又はその無水物類;こはく酸モノ〔2−(メタ)アクリロイロキシエチル〕、フタル酸モノ〔2−(メタ)アクリロイロキシエチル〕等の2価以上の多価カルボン酸のモノ〔(メタ)アクリロイロキシアルキル〕エステル類;ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート等の両末端にカルボキシ基と水酸基とを有するポリマーのモノ(メタ)アクリレート類等を挙げることができる。
これらのカルボキシル基含有不飽和単量体のうち、こはく酸モノ(2−アクリロイロキシエチル)及びフタル酸モノ(2−アクリロイロキシエチル)は、それぞれM−5300及びM−5400(東亞合成(株)製)の商品名で市販されている。
前記カルボキシル基含有不飽和単量体は、単独で又は2種以上を混合して使用することができる。
ここで、(メタ)アクリル酸とはアクリル酸又はメタクリル酸をいい、(メタ)アクリレートとは、アクリレート又はメタクリレートをいう。
Examples of the carboxyl group-containing unsaturated monomer include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid; maleic acid, maleic anhydride, fumaric acid, itacon Unsaturated dicarboxylic acids such as acid, itaconic anhydride, citraconic acid, citraconic anhydride, and mesaconic acid or their anhydrides; trivalent or higher unsaturated polycarboxylic acids or their anhydrides; succinic acid mono [2- ( [Meth] acryloyloxyethyl], mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono [2- (meth) acryloyloxyethyl] phthalate; ω-carboxypoly Examples include mono (meth) acrylates of polymers having a carboxy group and a hydroxyl group at both ends, such as caprolactone mono (meth) acrylate. it can.
Among these carboxyl group-containing unsaturated monomers, succinic acid mono (2-acryloyloxyethyl) and phthalic acid mono (2-acryloyloxyethyl) are respectively M-5300 and M-5400 (Toagosei ( (Commercially available) under the trade name.
The said carboxyl group-containing unsaturated monomer can be used individually or in mixture of 2 or more types.
Here, (meth) acrylic acid refers to acrylic acid or methacrylic acid, and (meth) acrylate refers to acrylate or methacrylate.
また、共重合性不飽和単量体としては、例えば、スチレン、α−メチルスチレン、o−ビニルトルエン、m−ビニルトルエン、p−ビニルトルエン、p−クロルスチレン、o−メトキシスチレン、m−メトキシスチレン、p−メトキシスチレン、o−ビニルベンジルメチルエーテル、m−ビニルベンジルメチルエーテル、p−ビニルベンジルメチルエーテル、o−ビニルベンジルグリシジルエーテル、m−ビニルベンジルグリシジルエーテル、p−ビニルベンジルグリシジルエーテル等の芳香族ビニル化合物;インデン、1−メチルインデン等のインデン類;メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、sec−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、3−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、3−ヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート、アリル(メタ)アクリレート、ベンジル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、フェニル(メタ)アクリレート、2−メトキシエチル(メタ)アクリレート、2−フェノキシエチル(メタ)アクリレート、メトキシジエチレングルコール(メタ)アクリレート、メトキシトリエチレングルコール(メタ)アクリレート、メトキシプロピレングルコール(メタ)アクリレート、メトキシジプロピレングルコール(メタ)アクリレート、イソボルニル(メタ)アクリレート、トリシクロ[ 5.2.1.02,6] デカン−8−イル(メタ)アクリレート、2−ヒドロキシ3−フェノキシプロピル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート等の不飽和カルボン酸エステル類;2−アミノエチル(メタ)アクリレート、2−ジメチルアミノエチル(メタ)アクリレート、2−アミノプロピル(メタ)アクリレート、2−ジメチルアミノプロピル(メタ)アクリレート、3−アミノプロピル(メタ)アクリレート、3−ジメチルアミノプロピル(メタ)アクリレート等の不飽和カルボン酸アミノアルキルエステル類;グリシジル(メタ)アクリレート等の不飽和カルボン酸グリシジルエステル類;酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、安息香酸ビニル等のカルボン酸ビニルエステル類;ビニルメチルエーテル、ビニルエチルエーテル、アリルグリシジルエーテル等の不飽和エーテル類;(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデン等のシアン化ビニル化合物;
(メタ)アクリルアミド、α−クロロアクリルアミド、N−2−ヒドロキシエチル(メタ)アクリルアミド等の不飽和アミド類;マレイミド、N−フェニルマレイミド、N−シクロヘキシルマレイミド等の不飽和イミド類;1,3−ブタジエン、イソプレン、クロロプレン等の脂肪族共役ジエン類;ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート、ポリシロキサン等の重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー類等を挙げることができる。
これらの共重合性不飽和単量体は、単独で又は2種以上を混合して使用することができる。
Examples of the copolymerizable unsaturated monomer include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, and m-methoxy. Styrene, p-methoxystyrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, etc. Aromatic vinyl compounds; indenes such as indene and 1-methylindene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, Isobuti (Meth) acrylate, sec-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2- Hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, 2 -Methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypro Pyreneglycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.02,6] decan-8-yl (meth) acrylate, 2-hydroxy 3 -Unsaturated carboxylic acid esters such as phenoxypropyl (meth) acrylate and glycerol mono (meth) acrylate; 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate , Unsaturated carboxylic acid aminoalkyl esters such as 2-dimethylaminopropyl (meth) acrylate, 3-aminopropyl (meth) acrylate and 3-dimethylaminopropyl (meth) acrylate; unsaturated carboxylic acid such as glycidyl (meth) acrylate Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; (meth) acrylonitrile, vinyl cyanide compounds such as α-chloroacrylonitrile and vinylidene cyanide;
Unsaturated amides such as (meth) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide; Unsaturated imides such as maleimide, N-phenylmaleimide, N-cyclohexylmaleimide; 1,3-butadiene , Isoprene, chloroprene, and other aliphatic conjugated dienes; macromolecules having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane, etc. And monomers.
These copolymerizable unsaturated monomers can be used alone or in admixture of two or more.
本発明におけるカルボキシル基含有共重合体としては、(メタ)アクリル酸を必須成分とし、場合により、こはく酸モノ〔2−(メタ)アクリロイロキシエチル〕及びω−カルボキシポリカプロラクトンモノ(メタ)アクリレートの群から選ばれる少なくとも1種の化合物を更に含有するカルボキシル基含有不飽和単量体成分と、スチレン、メチル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、アリル(メタ)アクリレート、ベンジル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート、N−フェニルマレイミド、ポリスチレンマクロモノマー及びポリメチルメタクリレートマクロモノマーの群から選ばれる少なくとも1種との共重合体(以下、「カルボキシル基含有共重合体(C1)」という。)が好ましい。 As the carboxyl group-containing copolymer in the present invention, (meth) acrylic acid is an essential component, and in some cases, succinic acid mono [2- (meth) acryloyloxyethyl] and ω-carboxypolycaprolactone mono (meth) acrylate. A carboxyl group-containing unsaturated monomer component further containing at least one compound selected from the group consisting of styrene, methyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl ( A copolymer with at least one selected from the group of (meth) acrylate, glycerol mono (meth) acrylate, N-phenylmaleimide, polystyrene macromonomer and polymethylmethacrylate macromonomer (hereinafter referred to as “carboxyl group-containing copolymer (C1) ) ").) Arbitrariness.
カルボキシル基含有共重合体(C1)の具体例としては、(メタ)アクリル酸/メチル(メタ)アクリレート共重合体、(メタ)アクリル酸/ベンジル(メタ)アクリレート共重合体、(メタ)アクリル酸/2−ヒドロキシエチル(メタ)アクリレート/ベンジル(メタ)アクリレート共重合体、(メタ)アクリル酸/メチル(メタ)アクリレート/ポリスチレンマクロモノマー共重合体、(メタ)アクリル酸/メチル(メタ)アクリレート/ポリメチルメタクリレートマクロモノマー共重合体、(メタ)アクリル酸/ベンジル(メタ)アクリレート/ポリスチレンマクロモノマー共重合体、(メタ)アクリル酸/ベンジル(メタ)アクリレート/ポリメチルメタクリレートマクロモノマー共重合体、(メタ)アクリル酸/2−ヒドロキシエチル(メタ)アクリレート/ベンジル(メタ)アクリレート/ポリスチレンマクロモノマー共重合体、(メタ)アクリル酸/2−ヒドロキシエチル(メタ)アクリレート/ベンジル(メタ)アクリレート/ポリメチルメタクリレートマクロモノマー共重合体、メタクリル酸/スチレン/ベンジル(メタ)アクリレート/N−フェニルマレイミド共重合体、(メタ)アクリル酸/こはく酸モノ〔2−(メタ)アクリロイロキシエチル〕/スチレン/ベンジル(メタ)アクリレート/N−フェニルマレイミド共重合体、(メタ)アクリル酸/こはく酸モノ〔2−(メタ)アクリロイロキシエチル〕/スチレン/アリル(メタ)アクリレート/N−フェニルマレイミド共重合体、(メタ)アクリル酸/スチレン/ベンジル(メタ)アクリレート/グリセロールモノ(メタ)アクリレート/N−フェニルマレイミド共重合体、(メタ)アクリル酸/ω−カルボキシポリカクロラクトンモノ(メタ)アクリレート/スチレン/ベンジル(メタ)アクリレート/グリセロールモノ(メタ)アクリレート/N−フェニルマレイミド共重合体等を挙げることができる。
アルカリ可溶性樹脂のゲルパーミエーションクロマトグラフィー(GPC、溶出溶媒:テトラヒドロフラン)で測定したポリスチレン換算重量平均分子量Mwは、通常、5,000〜20,000、好ましくは6,000〜18,000である。
また、アルカリ可溶性樹脂の酸価が30mgKOH/g〜150mgKOH/gであるものが好ましく、70mgKOH/g〜130mgKOH/gであるものが更に好ましい。本発明のアルカリ可溶性樹脂は、感光性組成物に含まれる固形分中に、1質量%〜50質量%の範囲内であることが好ましく、なかでも1質量%〜40質量%であることがより好ましい。なお、感光性組成物に含まれる固形分とは、溶媒以外の構成成分全てである。
Specific examples of the carboxyl group-containing copolymer (C1) include (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid. / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate copolymer, (meth) acrylic acid / methyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / methyl (meth) acrylate / Polymethyl methacrylate macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, ( (Meth) acrylic acid / 2-hydroxye (Meth) acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, methacryl Acid / styrene / benzyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / styrene / benzyl (meth) acrylate / N-phenyl Maleimide copolymer, (meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / styrene / allyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / styrene / Benzyl (meth) acrylate / g Serol mono (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / ω-carboxypolycacrolactone mono (meth) acrylate / styrene / benzyl (meth) acrylate / glycerol mono (meth) acrylate / N-phenyl A maleimide copolymer etc. can be mentioned.
The polystyrene-equivalent weight average molecular weight Mw measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) of an alkali-soluble resin is usually 5,000 to 20,000, preferably 6,000 to 18,000.
Moreover, the acid value of the alkali-soluble resin is preferably 30 mgKOH / g to 150 mgKOH / g, and more preferably 70 mgKOH / g to 130 mgKOH / g. The alkali-soluble resin of the present invention is preferably in the range of 1% by mass to 50% by mass in the solid content contained in the photosensitive composition, and more preferably 1% by mass to 40% by mass. preferable. In addition, solid content contained in the photosensitive composition is all components other than a solvent.
本発明の感光性組成物に配合される光重合性モノマーとしては、前記のアルカリ可溶性樹脂と相溶性のあるエチレン性不飽和二重結合を少なくとも1つ有する化合物、好ましくはエチレン性不飽和二重結合を少なくとも2つ有する化合物が挙げられる。上記のエチレン性不飽和二重結合を有する化合物としては、単官能(メタ)アクリレート、二官能(メタ)アクリレート及び三官能以上の(メタ)アクリレート等、好ましくは二官能以上の(メタ)アクリレートが挙げられる。 The photopolymerizable monomer blended in the photosensitive composition of the present invention includes a compound having at least one ethylenically unsaturated double bond compatible with the alkali-soluble resin, preferably an ethylenically unsaturated double bond. Examples include compounds having at least two bonds. Examples of the compound having an ethylenically unsaturated double bond include monofunctional (meth) acrylate, bifunctional (meth) acrylate, trifunctional or higher (meth) acrylate, and preferably bifunctional or higher (meth) acrylate. Can be mentioned.
上記の単官能(メタ)アクリレートとしては、例えば、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、ブタンジオールモノ(メタ)アクリレート、アリル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、t−ブチルアミノエチル(メタ)アクリレート、ブチル(メタ)アクリレート、ヘキシル(メタ)アクリレート、エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、オクチル(メタ)アクリレート、2−エチルヘキシルカルビトール(メタ)アクリレート、グリシジル(メタ)アクリレート等が挙げられる。 Examples of the monofunctional (meth) acrylate include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, and polypropylene glycol mono (meth) acrylate. , Butanediol mono (meth) acrylate, allyl (meth) acrylate, butoxyethyl (meth) acrylate, t-butylaminoethyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, ethylhexyl (meth) acrylate, Examples include lauryl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, and glycidyl (meth) acrylate.
また、上記の二単官能(メタ)アクリレートとしては、例えば、1,3−ブタンジオールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、ビスフェノールAジ(メタ)アクリレート、3−メチルペンタンジオールジ(メタ)アクリレート、フタル酸ジ(メタ)アクリレート、シクロヘキシレングリコールジ(メタ)アクリレート、メトキシ化シクロヘキシルジ(メタ)アクリレート等が挙げられる。 Examples of the bifunctional (meth) acrylate include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1 , 6-hexanediol di (meth) acrylate, polypropylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, bisphenol A di (meth) ) Acrylate, 3-methylpentanediol di (meth) acrylate, phthalic acid di (meth) acrylate, cyclohexylene glycol di (meth) acrylate, and methoxylated cyclohexyl di (meth) acrylate.
更に、上記の三官能以上の(メタ)アクリレートとしては、例えば、トリメチロールプロパントリ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート(DPHA)、ジペンタエリスリトールペンタ(メタ)アクリレート、カルボン酸変性ジペンタエリスリトールペンタアクリレート等が挙げられる。
上記の光重合性モノマーは、単独で又は2種以上を混合して使用することができる。
なお、本発明に用いられる光重合性モノマーの含有量は、本発明の感光性組成物に含まれる固形分中において、3質量%〜50質量%の範囲であることが好ましい。上記範囲より少ないと十分に光硬化が進まず、露光部分がアルカリ現像時に溶出する場合があるからである。また、上記範囲より多いと、アルカリ現像性が低下するため、未露光部分でも現像できなくなる可能性があるからである。
Further, as the above trifunctional or higher functional (meth) acrylate, for example, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate , Dipentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate (DPHA), dipentaerythritol penta (meth) acrylate, carboxylic acid-modified dipentaerythritol pentaacrylate, and the like.
Said photopolymerizable monomer can be used individually or in mixture of 2 or more types.
In addition, it is preferable that content of the photopolymerizable monomer used for this invention is the range of 3 mass%-50 mass% in solid content contained in the photosensitive composition of this invention. If the amount is less than the above range, photocuring does not proceed sufficiently, and the exposed portion may be eluted during alkali development. On the other hand, if the amount is larger than the above range, the alkali developability deteriorates, so that development may not be possible even in an unexposed portion.
本発明の感光性組成物に配合される光重合開始剤としては、公知の光重合開始剤を使用することができ、好ましくはイミダゾール系、アセトフェノン系、オキシムエステル系、ベンゾフェノン系、ベンゾインエーテル系、チオキサントン系、トリアジン系、ベンジル系、アントラキノン系、チオール系及びイオウ化合物系光重合開始剤から選ばれる少なくとも1種であり、とくに好ましくはイミダゾール系、アルキルフェノン系、ベンゾフェノン系、アセトフェノン系及びチオキサントン系光重合開始剤から選ばれる少なくとも1種である。 As the photopolymerization initiator compounded in the photosensitive composition of the present invention, a known photopolymerization initiator can be used, and preferably an imidazole series, an acetophenone series, an oxime ester series, a benzophenone series, a benzoin ether series, At least one selected from thioxanthone, triazine, benzyl, anthraquinone, thiol and sulfur compound photoinitiators, particularly preferably imidazole, alkylphenone, benzophenone, acetophenone and thioxanthone It is at least one selected from polymerization initiators.
上記のイミダゾール系光重合開始剤としては、ヘキサアリールビスイミダゾール系化合物等が挙げられ、これらの化合物としては、例えば、2,2'−ビス(o−クロルフェニル)−4,4',5,5'−テトラフェニルビスイミダゾリル、2,2'−ビス(o−クロルフェニル)−4,4',5,5'−テトラ−(p−メトキシフェニル)ビスイミダゾリル、2,2'−ビス(2クロロフェニル)−4,4'−5,5'テトラキスフェニル−1,2'ビイミダゾール等が挙げられる。 Examples of the imidazole photopolymerization initiator include hexaarylbisimidazole compounds. Examples of these compounds include 2,2′-bis (o-chlorophenyl) -4,4 ′, 5, 5′-tetraphenylbisimidazolyl, 2,2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetra- (p-methoxyphenyl) bisimidazolyl, 2,2′-bis (2 Chlorophenyl) -4,4′-5,5′tetrakisphenyl-1,2′biimidazole and the like.
また、上記のアセトフェノン系光重合開始剤としては、例えば、ジエトキシアセトフェノン、2−ヒドロキシ1−[4−(2−ヒドロキシエトキシ)フェニル]−2−メチルプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1(例えば、チバスペシャリティーケミカルズ社製、商品名「IRGACURE 369」)、2−(ジメチルアミノ)−2−[(4−メチルフェニル)メチル]−1−[4−(4−モルホリニル)フェニル]−1−ブタノン、ベンジルジメチルケタール、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1−(4−メチルチオフェニル)−2−モルホリノプロパン−1−オン(例えば、チバスペシャリティーケミカルズ社製、商品名「IRGACURE 907」)、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1−{4−[4−(2−ヒドロキシ2−メチル−プロピオニル)−ベンジル]フェニル}−2−メチルプロパン−1−オン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン等が挙げられる。 Examples of the acetophenone photopolymerization initiator include diethoxyacetophenone, 2-hydroxy 1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, and 2-benzyl-2. -Dimethylamino-1- (4-morpholinophenyl) -butanone-1 (for example, trade name “IRGACURE 369” manufactured by Ciba Specialty Chemicals), 2- (dimethylamino) -2-[(4-methylphenyl) Methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1 -ON (for example, product name “IRGACU” manufactured by Ciba Specialty Chemicals, Inc. RE 907 "), 2-hydroxy 2-methyl-1-phenylpropan-1-one, 2-hydroxy 1- {4- [4- (2-hydroxy 2-methyl-propionyl) -benzyl] phenyl} -2- Examples include methylpropan-1-one and 2,2-dimethoxy-1,2-diphenylethane-1-one.
また、上記のベンゾフェノン系光重合開始剤としては、例えば、ベンゾフェノン、4−フェニルベンゾフェノン、4−ベンゾイル−4'−メチルジフェニルサルファイド、3,3',4,4'−テトラ(tert−ブチルパーオキシカルボニル)ベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4,4'−ビス−ジメチルアミノベンゾフェノン等が挙げられる。 Examples of the benzophenone photopolymerization initiator include benzophenone, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxy). Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 4,4′-bis-dimethylaminobenzophenone and the like.
また、上記のチオキサントン系光重合開始剤としては、例えば、2−及び4−イソプロピルチオキサントン、2,4−ジエチルチオキサントン、1−クロロ−4−プロポキシチオキサントン、2,4−ジクロロチオキサントン等が挙げられる。
このような光重合開始剤の含有量としては、上記感光性組成物を所望の硬化速度で光硬化することができる量であればよく、本発明の感光性組成物中に含まれる固形分中において、0.1質量%〜30質量%の範囲であることが好ましい。
Examples of the thioxanthone photopolymerization initiator include 2- and 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 1-chloro-4-propoxythioxanthone, and 2,4-dichlorothioxanthone.
As content of such a photoinitiator, what is necessary is just the quantity which can carry out photocuring of the said photosensitive composition with a desired cure rate, and it is in solid content contained in the photosensitive composition of this invention. In this case, it is preferably in the range of 0.1% by mass to 30% by mass.
本発明の感光性樹脂組成物においては、本発明の目的を妨げない範囲において、所望により種々の添加剤を配合しても良い。これらの添加剤としては、カラーフィルター用ガラス基板への上記感光性樹脂組成物の塗膜の濡れ性向上のためのノニオン系、カチオン系、アニオン系等の各種の界面活性剤、また、密着性向上のためにアクリル系シランカップリング剤、エポキシ系シランカップリング剤、ウレイド系シランカップリング剤等のシランカップリング剤、その他、消泡剤、ハジキ防止剤、酸化防止剤、凝集防止剤、紫外線吸収剤等が挙げられる。 In the photosensitive resin composition of this invention, you may mix | blend various additives depending on necessity in the range which does not interfere with the objective of this invention. As these additives, various surfactants such as nonionic, cationic and anionic surfactants for improving the wettability of the coating film of the photosensitive resin composition on the glass substrate for color filter, and adhesion Silane coupling agents such as acrylic silane coupling agents, epoxy silane coupling agents, ureido silane coupling agents, etc., antifoaming agents, repellency inhibitors, antioxidants, anti-aggregation agents, UV rays An absorbent etc. are mentioned.
上記のように調製された本発明の感光性組成物は、例えば、これを用いて、遮光層がパターン形成されたカラーフィルター用のガラス基板に回転塗布(スピンコート)、流延塗布、浸漬塗布、ロール塗布、特にダイコート法等の公知の塗布方法により塗布し、真空度が13〜133Pa程度、例えば26Paに到達するまで真空ベイクを行って0.5〜4μm程度(乾燥膜厚)の塗布膜を得る。得られた塗布膜に目的の緑色着色層を画素として形成するためのネガ型のフォトマスクを介して高圧水銀灯や超高圧水銀灯等により10〜500mJ/cm2 程度の光量の紫外線を照射し露光する。露光後、光硬化した塗膜を公知のアルカリ現像液を使用してスプレイ法や浸漬法にて現像し、未露光部を溶解して目的とする緑色に相当する画素を得る。必要に応じて、現像後、200〜250℃程度の温度で10〜60分程度、後硬化処理(ポストベイク)することができる。上記の画素を得る工程を、カラーフィルターに必要とされる他の色の数だけ繰り返すことによって目的とするカラーフィルターが得られる。上記のカラーフィルターは、通常、赤、緑及び青の各画素を遮光層がパターン形成されたカラーフィルター用のガラス基板上に配置したものである。 The photosensitive composition of the present invention prepared as described above is used, for example, for spin coating, casting coating, and dip coating on a glass substrate for a color filter in which a light shielding layer is patterned. Coating by a known coating method such as roll coating, particularly die coating, and vacuum baking is performed until the degree of vacuum reaches about 13 to 133 Pa, for example, 26 Pa, and a coating film of about 0.5 to 4 μm (dry film thickness) Get. The obtained coating film is exposed by irradiating it with ultraviolet light having a light quantity of about 10 to 500 mJ / cm @ 2 by means of a high pressure mercury lamp, an ultra high pressure mercury lamp or the like through a negative photomask for forming a target green colored layer as a pixel. After the exposure, the photocured coating film is developed by a spray method or a dipping method using a known alkali developer, and the unexposed portion is dissolved to obtain a pixel corresponding to the target green color. If necessary, after development, post-curing can be performed at a temperature of about 200 to 250 ° C. for about 10 to 60 minutes. The target color filter is obtained by repeating the above-described step of obtaining the pixels by the number of other colors required for the color filter. The above color filter is usually one in which each pixel of red, green and blue is arranged on a glass substrate for a color filter in which a light shielding layer is patterned.
上記のアルカリ現像液は、無機あるいは有機のアルカリ化合物と、必要に応じて界面活性剤を含有するアルカリ性水溶液である。上記の無機アルカリ化合物としては、例えば、水酸化カリウム、水酸化ナトリウム、燐酸水素ナトリウム、燐酸水素アンモニウム、珪酸カリウム、珪酸ナトリウム、炭酸カリウム、炭酸ナトリウム、炭酸水素カリウム、炭酸水素ナトリウム、硼酸カリウムであり、また、有機アルカリ化合物としては、例えば、モノメチルアミン、モノエチルアミン、ジメチルアミン、トリエチルアミン、エタノールアミン、2−ヒドロキシエチルトリメチルアンモニウムヒドロキシド等が挙げられる。上記のアルカリ性水溶液の濃度は、0.01〜10質量%程度、好ましくは0.03〜0.07質量%である。 The alkaline developer is an alkaline aqueous solution containing an inorganic or organic alkaline compound and, if necessary, a surfactant. Examples of the inorganic alkali compound include potassium hydroxide, sodium hydroxide, sodium hydrogen phosphate, ammonium hydrogen phosphate, potassium silicate, sodium silicate, potassium carbonate, sodium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, and potassium borate. Examples of the organic alkali compound include monomethylamine, monoethylamine, dimethylamine, triethylamine, ethanolamine, and 2-hydroxyethyltrimethylammonium hydroxide. The concentration of the alkaline aqueous solution is about 0.01 to 10% by mass, preferably 0.03 to 0.07% by mass.
本発明を実施例により、更に詳細に説明するが、本発明は、これらの例によってなんら限定されるものではない。
なお、緑色分散液の分散粒子の平均粒径及び分散安定性、感光性組成物の分散安定性並びにカラーフィルターの着色層の輝度及びコントラストの評価は、下記の方法に従って実施した。
Examples The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
The average particle size and dispersion stability of the dispersed particles of the green dispersion, the dispersion stability of the photosensitive composition, and the brightness and contrast of the colored layer of the color filter were evaluated according to the following methods.
(1)分散粒子の平均粒径
顔料分散体0.1質量部をPGMEA(プロピレングリコールモノメチルエーテルアセテート)溶媒9.9質量部で希釈し、マイクロトラックUPA粒度分布計(日機装社製)を用いて、粒度分布を測定し、その粒度分布の積算値50%の粒度を平均粒径とした。
(1) Average particle diameter of dispersed particles 0.1 parts by mass of a pigment dispersion was diluted with 9.9 parts by mass of a PGMEA (propylene glycol monomethyl ether acetate) solvent, and a Microtrac UPA particle size distribution meter (manufactured by Nikkiso Co., Ltd.) was used. The particle size distribution was measured, and the particle size with an integrated value of 50% of the particle size distribution was defined as the average particle size.
(2)分散安定性
顔料分散液を製造直後の粘度及び23℃の恒温槽に7日間静置した後の粘度をA&D社製 振動式粘度計CJV−5000にて25℃で測定し、測定開始から60秒後の値を粘度とした。各実施例及び比較例の顔料分散液について、上記7日間での粘度変化率を評価した。
◎:粘度変化率が3%未満である。
○:粘度変化率が3%以上、5%未満である。
△:粘度変化率が5%以上、10%未満である。
×:粘度変化率が10%以上である。
(2) Dispersion stability The viscosity immediately after production of the pigment dispersion and the viscosity after standing for 7 days in a thermostatic bath at 23 ° C. were measured at 25 ° C. with a vibratory viscometer CJV-5000 manufactured by A & D, and measurement started. The value 60 seconds after was taken as the viscosity. About the pigment dispersion liquid of each Example and a comparative example, the viscosity change rate in the said 7 days was evaluated.
A: Viscosity change rate is less than 3%.
○: Viscosity change rate is 3% or more and less than 5%.
Δ: Viscosity change rate is 5% or more and less than 10%.
X: Viscosity change rate is 10% or more.
(4)輝度
オリンパス(株)製OSP−SP200顕微分光測光装置を用いて、JIS Z8701に定める明るさY値を測定した。測定条件は、光源がC光源、照明倍率20倍、ピンホールNo.7(50μm)である。
◎:65.0以上
○:60.0以上、65.0未満
△:55.0以上、60.0未満
×:55.0未満
(4) Luminance The brightness Y value defined in JIS Z8701 was measured using an OSP-SP200 microspectrophotometric device manufactured by Olympus Corporation. The measurement conditions were as follows: the light source was a C light source, the illumination magnification was 20 times, and the pinhole no. 7 (50 μm).
◎: 65.0 or more ○: 60.0 or more, less than 65.0 △: 55.0 or more, less than 60.0 ×: less than 55.0
(5)コントラスト
カラーフィルターの緑色着色層を2枚の偏光板(日東電工(株)製、商品名「NPF−G 1220DU」で挟み込み、バックライト(株式会社東芝製、商品名「メロウ5D FL10EX−D−H」、色温度6500K)を点灯し、偏光板の直交時と平行時の輝度を輝度計(ミノルタ社製、商品名「LS−100」)により測定した。コントラストは輝度の測定値を用い、以下の式により導き出せる。
コントラスト=平行輝度(cd/m2)/直交輝度(cd/m2)
◎;5200以上
○;4800以上、5200未満
△;4400以上、4800未満
×;4400未満
(5) Contrast The green colored layer of the color filter is sandwiched between two polarizing plates (manufactured by Nitto Denko Corporation, trade name “NPF-G 1220DU”), and a backlight (made by Toshiba Corporation, trade name “Mellow 5D FL10EX— DH ", color temperature 6500K) was turned on, and the luminance when the polarizing plate was orthogonal and parallel was measured with a luminance meter (trade name" LS-100 "manufactured by Minolta Co.). And can be derived from the following equation:
Contrast = parallel luminance (cd / m2) / orthogonal luminance (cd / m2)
◎; 5200 or more ○; 4800 or more, less than 5200 △; 4400 or more, less than 4800 ×; less than 4400
アルカリ可溶性樹脂の合成
アルカリ可溶性樹脂として、ベンジルメタクリレート共重合樹脂{ベンジルメタクリレート/スチレン/メタクリル酸/(+グリシジルメタクリレート)=20/43/25/12(モル%)}を以下のように合成した。
ベンジルメタクリレート 30g(0.17モル)
スチレン 38g(0.37モル)
メタクリル酸 18g(0.21モル)
と、t−ブチルパーオキシ−2−エチルヘキサノエー卜(日本油脂製、パーブチルO)10gとの混合液を、プロピレングリコールモノメチルエーテルアセテート150gを入れた重合槽中に、窒素気流下100℃で、3時間かけて滴下した。滴下終了後さらに3時間加熱することにより重合体溶液を得た。この重合体の重量平均分子量はポリスチレン換算で8,000であった。
次に、得られた重合体溶液に、以下の組成
グリシジルメタクリレート 14g(0.10モル)
トリエチルアミン 0.2g
p−メトキシフェノール 0.05g
を添加し、110℃で10時間加熱することにより主鎖メタクリル酸のカルボン酸基とグリシジルメタクリレートのエポキシ基との反応を行った。反応中は、グリシジルメタクルートの重合を防ぐため、反応溶液内に空気をバブリングさせた。反応は溶液の酸価測定により追跡した。得られた反応溶液は固形分38%、酸価75mgKOH/g、重量平均分子量はポリスチレン換算で10,000であった。
Synthesis of alkali-soluble resin As an alkali-soluble resin, a benzyl methacrylate copolymer resin {benzyl methacrylate / styrene / methacrylic acid / (+ glycidyl methacrylate) = 20/43/25/12 (mol%)} was synthesized as follows.
Benzyl methacrylate 30 g (0.17 mol)
Styrene 38g (0.37mol)
Methacrylic acid 18g (0.21 mol)
And 10 g of t-butylperoxy-2-ethylhexanoe koji (manufactured by NOF Corporation, perbutyl O) in a polymerization tank containing 150 g of propylene glycol monomethyl ether acetate at 100 ° C. under a nitrogen stream. It was dripped over 3 hours. After completion of the dropwise addition, a polymer solution was obtained by heating for an additional 3 hours. The weight average molecular weight of this polymer was 8,000 in terms of polystyrene.
Next, to the obtained polymer solution, the following composition glycidyl methacrylate 14 g (0.10 mol)
Triethylamine 0.2g
p-Methoxyphenol 0.05g
Was added and heated at 110 ° C. for 10 hours to react the carboxylic acid group of the main chain methacrylic acid with the epoxy group of glycidyl methacrylate. During the reaction, air was bubbled into the reaction solution in order to prevent polymerization of glycidyl methacrylate. The reaction was followed by measuring the acid value of the solution. The obtained reaction solution had a solid content of 38%, an acid value of 75 mgKOH / g, and a weight average molecular weight of 10,000 in terms of polystyrene.
実施例1
表1に示す配合内容により、ディゾルバーにて1時間撹拌混合し、緑色混合物を得た。得られた緑色混合物をピコグレンミルPCMH C2M(浅田鉄工(株)製)にて分散し、予備分散液を得た。分散メディアとして直径0.1mmのジルコニアビーズを使用した。得られた予備分散液の分散粒子の平均粒径は、60nmであった。
次に、得られた予備分散液をアルティマイザー{(株)スギノマシン製}を用いて200MPaの超高圧下で予備分散液同士を高圧衝突分散した。この高圧衝突分散処理を3回繰り返し、緑色分散液を得た。得られた緑色分散液の分散粒子の平均粒径は、20nmであった。この緑色分散液の分散安定性を評価した。結果を表1に示す。
Example 1
According to the contents shown in Table 1, the mixture was stirred and mixed for 1 hour with a dissolver to obtain a green mixture. The obtained green mixture was dispersed with Pico Glen Mill PCMH C2M (manufactured by Asada Tekko Co., Ltd.) to obtain a preliminary dispersion. As a dispersion medium, zirconia beads having a diameter of 0.1 mm were used. The average particle size of the dispersed particles of the obtained preliminary dispersion was 60 nm.
Next, the preliminary dispersions were subjected to high-pressure collision dispersion between the preliminary dispersions under an ultrahigh pressure of 200 MPa using an optimizer {manufactured by Sugino Machine Co., Ltd.}. This high-pressure collision dispersion treatment was repeated three times to obtain a green dispersion. The average particle diameter of the dispersed particles of the obtained green dispersion liquid was 20 nm. The dispersion stability of this green dispersion was evaluated. The results are shown in Table 1.
比較例1
実施例1の分散メディアを、直径1mmのジルコニアビーズに変更した以外は、同じ配合処方及び混合方法にて予備分散液を得た。得られた予備分散液の分散粒子の平均粒径は、130nmであった。
次に、得られた予備分散液を、実施例1と同様の方法にて緑色分散液を得た。得られた緑色分散液の分散粒子の平均粒径は、100nmであった。この緑色分散液の分散安定性を評価した。結果を表1に示す。
Comparative Example 1
A preliminary dispersion was obtained by the same formulation and mixing method except that the dispersion medium of Example 1 was changed to zirconia beads having a diameter of 1 mm. The average particle diameter of the dispersed particles of the obtained preliminary dispersion was 130 nm.
Next, a green dispersion was obtained from the obtained preliminary dispersion in the same manner as in Example 1. The average particle diameter of the dispersed particles of the obtained green dispersion was 100 nm. The dispersion stability of this green dispersion was evaluated. The results are shown in Table 1.
比較例2
実施例1と同じ配合処方及び混合方法にて予備分散液を得た。得られた予備分散液の分散粒子の平均粒径は、60nmであった。この予備分散液を高圧衝突分散処理せず、そのまま緑色分散液とした。この緑色分散液の分散安定性を評価した。結果を表1に示す。
Comparative Example 2
A preliminary dispersion was obtained by the same formulation and mixing method as in Example 1. The average particle size of the dispersed particles of the obtained preliminary dispersion was 60 nm. This preliminary dispersion was not subjected to high-pressure collision dispersion treatment, and was used as it was as a green dispersion. The dispersion stability of this green dispersion was evaluated. The results are shown in Table 1.
比較例3
実施例1の顔料(A)を、ハロゲン化銅フタロシアニン顔料に変更した以外は、同じ配合処方及び混合方法にて予備分散液を得た。得られた予備分散液の分散粒子の平均粒径は、60nmであった。
次に、得られた予備分散液から、実施例1と同様の方法にて緑色分散液を得た。得られた緑色分散液の分散粒子の平均粒径は、20nmであった。この緑色分散液の分散安定性を評価した。結果を表1に示す。
Comparative Example 3
A preliminary dispersion was obtained by the same formulation and mixing method except that the pigment (A) of Example 1 was changed to a halogenated copper phthalocyanine pigment. The average particle size of the dispersed particles of the obtained preliminary dispersion was 60 nm.
Next, a green dispersion was obtained from the obtained preliminary dispersion in the same manner as in Example 1. The average particle diameter of the dispersed particles of the obtained green dispersion liquid was 20 nm. The dispersion stability of this green dispersion was evaluated. The results are shown in Table 1.
次に、実施例1及び比較例1〜3の緑色分散液に、それぞれ上記アルカリ可溶性樹脂の合成により得られたアルカリ可溶性樹脂(ベンジルメタクリレート共重合樹脂)、光重合性モノマー(ジペンタエリスリトールヘキサアクリレート、日本化薬(株)製、商品名「KAYARAD DPHA」)及び光重合開始剤(チバスペシャリティーケミカルズ社製、商品名「IRGACURE 369」)及び有機溶剤(プロピレングリコールモノメチルエーテルアセテート)を、下記配合処方によりビーズミルを使用して均一に混合分散し、4種類の実施例1及び比較例1〜3のアルカリ可溶型緑色感光性組成物を得た。これらの感光性組成物の分散安定性を評価した。結果を表1に示す。
アルカリ可溶型緑色感光性組成物の配合処方
顔料(表1参照) 8質量部
分散剤(表1参照) 16質量部
アルカリ可溶性樹脂 12質量部
光重合性モノマー 5質量部
光重合開始剤 3質量部
(商品名「IRGACURE 369」)
有機溶剤 56質量部
Next, in the green dispersions of Example 1 and Comparative Examples 1 to 3, the alkali-soluble resin (benzyl methacrylate copolymer resin) and the photopolymerizable monomer (dipentaerythritol hexaacrylate) obtained by synthesizing the alkali-soluble resin, respectively. Nippon Kayaku Co., Ltd., trade name “KAYARAD DPHA”) and photopolymerization initiator (Ciba Specialty Chemicals, trade name “IRGACURE 369”) and organic solvent (propylene glycol monomethyl ether acetate) The mixture was uniformly mixed and dispersed using a bead mill according to the formulation, and four types of alkali-soluble green photosensitive compositions of Example 1 and Comparative Examples 1 to 3 were obtained. The dispersion stability of these photosensitive compositions was evaluated. The results are shown in Table 1.
Formulation of alkali-soluble green photosensitive composition Pigment (see Table 1) 8 parts by weight Dispersant (see Table 1) 16 parts by weight Alkali-soluble resin 12 parts by weight Photopolymerizable monomer 5 parts by weight Photopolymerization initiator 3 parts by weight (Product name "IRGACURE 369")
56 parts by mass of organic solvent
更に、これら4種類の感光性組成物を使用して、それぞれ、ガラス基板に、ダイコーターを用いて塗布した後、真空度が26Paに到達するまで真空ベイクを行って、膜厚2.3μmの緑色着色層を形成した。
4種類の緑色着色層それぞれの輝度及びコントラストを上記の方法に従って実施した。結果を表1に示す。
Furthermore, using these four types of photosensitive compositions, each was coated on a glass substrate using a die coater, and then vacuum baked until the degree of vacuum reached 26 Pa, so that the film thickness was 2.3 μm. A green colored layer was formed.
The brightness and contrast of each of the four types of green colored layers were implemented according to the above method. The results are shown in Table 1.
*1: ハロゲン化亜鉛フタロシアニン顔料(A)、大日本インキ化学工業(株)製、商品名「FASTOGEN GREEN A110」
*2: ハロゲン化銅フタロシアニン顔料、大日本インキ化学工業(株)製、商品名
「FASTOGEN GREEN 2YK」
*3: アゾ化合物のニッケル錯体顔料(B)、ランクセス(株)社製、商品名「Gelb pigment E4GN−GT」
*4: ビックケミー社製、商品名「Disperbyk 161」
*5: プロピレングリコールモノメチルエーテルアセテート
* 1: Zinc halide phthalocyanine pigment (A), manufactured by Dainippon Ink & Chemicals, Inc., trade name “FASTOGEN GREEN A110”
* 2: Copper halide phthalocyanine pigment, manufactured by Dainippon Ink & Chemicals, Inc., trade name “FASTOGEN GREEN 2YK”
* 3: Nickel complex pigment (B) of azo compound, manufactured by LANXESS Co., Ltd., trade name "Gelb pigment E4GN-GT"
* 4: Product name “Disperbyk 161” manufactured by Big Chemie
* 5: Propylene glycol monomethyl ether acetate
表1から明らかなように、ハロゲン化亜鉛フタロシアニン顔料(A)を用い、且つ分散粒子の平均粒径が10〜100nmである予備分散液を所定の圧力下で高圧衝突分散処理した実施例1の緑色分散液及びアルカリ可溶型緑色感光性組成物の分散安定性はいずれも比較例1〜3の緑色分散液及びアルカリ可溶型緑色感光性組成物と比較して良好であった。
実施例1の緑色着色層は分散粒子の平均粒径が小さいので、比較例1の緑色着色層と比較して、輝度及びコントラストが大幅に良好であった。
また、実施例1のカラーフィルターの緑色着色層は、比較例2の緑色着色層と比較して、輝度及びコントラストが良好であり、比較例3の緑色着色層と比較して、輝度が良好であった。
As is apparent from Table 1, the predispersed liquid in which the halogenated zinc phthalocyanine pigment (A) was used and the average particle diameter of the dispersed particles was 10 to 100 nm was subjected to high-pressure collision dispersion treatment under a predetermined pressure. The dispersion stability of the green dispersion and the alkali-soluble green photosensitive composition was good compared to the green dispersion and the alkali-soluble green photosensitive composition of Comparative Examples 1-3.
Since the green colored layer of Example 1 had a small average particle diameter of dispersed particles, the brightness and contrast were significantly better than those of the green colored layer of Comparative Example 1.
In addition, the green colored layer of the color filter of Example 1 has better luminance and contrast than the green colored layer of Comparative Example 2, and has better luminance than the green colored layer of Comparative Example 3. there were.
本発明の緑色分散液及びそれを用いたアルカリ可溶型緑色感光性組成物は、高精細なカラーフィルター、特に液晶表示装置の大型ガラス基板を有するカラーフィルター用の感光性樹脂組成物として好適に用いられる。 The green dispersion of the present invention and the alkali-soluble green photosensitive composition using the same are suitably used as a photosensitive resin composition for high-definition color filters, particularly color filters having a large glass substrate for liquid crystal display devices. Used.
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007279284A JP5230993B2 (en) | 2007-10-26 | 2007-10-26 | Green dispersion, alkali-soluble green photosensitive composition and method for producing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007279284A JP5230993B2 (en) | 2007-10-26 | 2007-10-26 | Green dispersion, alkali-soluble green photosensitive composition and method for producing them |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009108135A true JP2009108135A (en) | 2009-05-21 |
JP5230993B2 JP5230993B2 (en) | 2013-07-10 |
Family
ID=40776986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007279284A Active JP5230993B2 (en) | 2007-10-26 | 2007-10-26 | Green dispersion, alkali-soluble green photosensitive composition and method for producing them |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5230993B2 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010150843A1 (en) * | 2009-06-25 | 2010-12-29 | 東洋インキ製造株式会社 | Colorant composition for a color filter, color filter using the same, and liquid crystal display device |
JP2011008004A (en) * | 2009-06-25 | 2011-01-13 | Toppan Printing Co Ltd | Coloring composition for color filter, color filter using the same, and liquid crystal display device |
JP2013023561A (en) * | 2011-07-20 | 2013-02-04 | Dic Corp | Pigment composition for color filter, method for producing the same, and color filter |
KR101248778B1 (en) | 2012-12-28 | 2013-04-03 | 한국항공우주연구원 | Decision method for position of geostationary orbit satellite using gps signal |
JP2013254214A (en) * | 2013-07-26 | 2013-12-19 | Fujifilm Corp | Colored composition for color filter, color filter, method for manufacturing color filter, and method for manufacturing colored composition for color filter |
KR20150010555A (en) * | 2013-07-19 | 2015-01-28 | 동우 화인켐 주식회사 | Photosensitive resin composition for transparent pixel |
JP2015034964A (en) * | 2013-02-28 | 2015-02-19 | 富士フイルム株式会社 | Transparent resin layer-forming composition, transparent resin layer, solid-state image sensor, and optoelectronic device |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07198933A (en) * | 1993-12-28 | 1995-08-01 | Japan Synthetic Rubber Co Ltd | Production of pigment dispersion liquid for color filter |
JPH0841395A (en) * | 1994-07-28 | 1996-02-13 | Mitsubishi Chem Corp | Preparation of coloring substance dispersion for use as ink jet recording liquid |
JPH09296142A (en) * | 1996-04-30 | 1997-11-18 | Japan Synthetic Rubber Co Ltd | Coloring composition |
JPH1036738A (en) * | 1996-07-22 | 1998-02-10 | Mitsubishi Pencil Co Ltd | Production of ink composition for ink-jest recording and ink composition for ink-jet recording |
JP2001288393A (en) * | 2000-01-31 | 2001-10-16 | Canon Inc | Recording ink, inkjet recording method, method for producing color filter, color filters, method for producing liquid crystal display panel, liquid crystal display panel and yellow ink |
JP2001354869A (en) * | 2000-04-04 | 2001-12-25 | Bayer Ag | Organic pigment to be put in color filter of liquid crystalline display |
JP2005194326A (en) * | 2003-12-26 | 2005-07-21 | Kao Corp | Method for producing water-based ink |
JP2005194322A (en) * | 2003-12-26 | 2005-07-21 | Kao Corp | Manufacturing process of pigment dispersion |
JP2006284691A (en) * | 2005-03-31 | 2006-10-19 | Dainippon Ink & Chem Inc | Green pigment composition for color filter, and color filter containing same in green pixel portion |
JP2007025687A (en) * | 2005-07-19 | 2007-02-01 | Lanxess Deutschland Gmbh | Organic pigments for color filter |
-
2007
- 2007-10-26 JP JP2007279284A patent/JP5230993B2/en active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07198933A (en) * | 1993-12-28 | 1995-08-01 | Japan Synthetic Rubber Co Ltd | Production of pigment dispersion liquid for color filter |
JPH0841395A (en) * | 1994-07-28 | 1996-02-13 | Mitsubishi Chem Corp | Preparation of coloring substance dispersion for use as ink jet recording liquid |
JPH09296142A (en) * | 1996-04-30 | 1997-11-18 | Japan Synthetic Rubber Co Ltd | Coloring composition |
JPH1036738A (en) * | 1996-07-22 | 1998-02-10 | Mitsubishi Pencil Co Ltd | Production of ink composition for ink-jest recording and ink composition for ink-jet recording |
JP2001288393A (en) * | 2000-01-31 | 2001-10-16 | Canon Inc | Recording ink, inkjet recording method, method for producing color filter, color filters, method for producing liquid crystal display panel, liquid crystal display panel and yellow ink |
JP2001354869A (en) * | 2000-04-04 | 2001-12-25 | Bayer Ag | Organic pigment to be put in color filter of liquid crystalline display |
JP2005194326A (en) * | 2003-12-26 | 2005-07-21 | Kao Corp | Method for producing water-based ink |
JP2005194322A (en) * | 2003-12-26 | 2005-07-21 | Kao Corp | Manufacturing process of pigment dispersion |
JP2006284691A (en) * | 2005-03-31 | 2006-10-19 | Dainippon Ink & Chem Inc | Green pigment composition for color filter, and color filter containing same in green pixel portion |
JP2007025687A (en) * | 2005-07-19 | 2007-02-01 | Lanxess Deutschland Gmbh | Organic pigments for color filter |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010150843A1 (en) * | 2009-06-25 | 2010-12-29 | 東洋インキ製造株式会社 | Colorant composition for a color filter, color filter using the same, and liquid crystal display device |
JP2011008004A (en) * | 2009-06-25 | 2011-01-13 | Toppan Printing Co Ltd | Coloring composition for color filter, color filter using the same, and liquid crystal display device |
CN102460240A (en) * | 2009-06-25 | 2012-05-16 | 东洋油墨Sc控股株式会社 | Colorant composition for color filter, color filter using same, and liquid crystal display device |
CN102460240B (en) * | 2009-06-25 | 2014-06-25 | 东洋油墨Sc控股株式会社 | Colorant composition for color filter, color filter using same, and liquid crystal display device |
KR101498191B1 (en) * | 2009-06-25 | 2015-03-03 | 토요잉크Sc홀딩스주식회사 | Colorant composition for a color filter, color filter using the same, and liquid crystal display device |
JP2013023561A (en) * | 2011-07-20 | 2013-02-04 | Dic Corp | Pigment composition for color filter, method for producing the same, and color filter |
KR101248778B1 (en) | 2012-12-28 | 2013-04-03 | 한국항공우주연구원 | Decision method for position of geostationary orbit satellite using gps signal |
JP2015034964A (en) * | 2013-02-28 | 2015-02-19 | 富士フイルム株式会社 | Transparent resin layer-forming composition, transparent resin layer, solid-state image sensor, and optoelectronic device |
KR20150010555A (en) * | 2013-07-19 | 2015-01-28 | 동우 화인켐 주식회사 | Photosensitive resin composition for transparent pixel |
JP2015022308A (en) * | 2013-07-19 | 2015-02-02 | 東友ファインケム株式会社 | Photosensitive resin composition for forming transparent pixel |
KR102093759B1 (en) * | 2013-07-19 | 2020-03-26 | 동우 화인켐 주식회사 | Photosensitive resin composition for transparent pixel |
JP2013254214A (en) * | 2013-07-26 | 2013-12-19 | Fujifilm Corp | Colored composition for color filter, color filter, method for manufacturing color filter, and method for manufacturing colored composition for color filter |
Also Published As
Publication number | Publication date |
---|---|
JP5230993B2 (en) | 2013-07-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI719016B (en) | Colored photosensitive resin composition, color filter, and image display apparatus comprising the same | |
JP4797993B2 (en) | Active energy ray-curable composition | |
JP5281412B2 (en) | Black matrix pigment dispersion composition and black matrix pigment dispersion resist composition containing the same | |
JP5230993B2 (en) | Green dispersion, alkali-soluble green photosensitive composition and method for producing them | |
JP4210460B2 (en) | Pigment dispersant, pigment dispersion composition, colored coating composition and color filter | |
JP3940535B2 (en) | Radiation sensitive composition for black resist | |
JP4428911B2 (en) | Radiation sensitive composition for color filter, color filter and color liquid crystal display element | |
TWI612382B (en) | Colored photosensitive resin composition for red pixel, color filter using thereof and display device having the same | |
JP4586918B2 (en) | Active energy ray-curable composition and method for producing the same | |
JP5491019B2 (en) | Photosensitive coloring composition and color filter using the same | |
CN104932196B (en) | Colored photosensitive resin composition and colour filter comprising the composition | |
NL1017826C2 (en) | Pigment dispersions. | |
JP5460179B2 (en) | Photosensitive red composition for color filter and color filter using the same | |
JP5130914B2 (en) | Active energy ray-curable composition | |
JP5144971B2 (en) | Photosensitive resin composition | |
JP2003248115A (en) | Color filter, radiation sensitive composition therefor and color liquid crystal display device | |
JP2003241374A (en) | Binder for organic solvent-based colored resist comprising alkali-soluble graft polymer, pigment dispersion for organic solvent-based colored resist, photosensitive colored composition and color filter | |
JP3960311B2 (en) | Curable resin composition for die coating, color filter, method for producing color filter, and liquid crystal display device | |
JP4136745B2 (en) | Pigment dispersion aid for preparing pigment dispersion for colored resist, pigment dispersion for colored resist, photosensitive coloring composition, and color filter | |
JP2010223987A (en) | Red composition for color filter and color filter having the same | |
JP5460204B2 (en) | Photosensitive red composition for color filter and color filter using the same | |
JP2001164142A (en) | Pigment dispersion composition | |
JP2004177498A (en) | Photosetting resin composition and its use | |
JPWO2008102834A1 (en) | Curable pigment dispersant | |
JP4325215B2 (en) | Colored resin composition, color filter, and liquid crystal display device |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20101005 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130218 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130226 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130321 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160329 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5230993 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |