JP5011560B2 - 短波長レーザ露光装置用着色感光性樹脂組成物、これを用いたカラーフィルタ及び液晶表示装置 - Google Patents
短波長レーザ露光装置用着色感光性樹脂組成物、これを用いたカラーフィルタ及び液晶表示装置 Download PDFInfo
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- JP5011560B2 JP5011560B2 JP2010057638A JP2010057638A JP5011560B2 JP 5011560 B2 JP5011560 B2 JP 5011560B2 JP 2010057638 A JP2010057638 A JP 2010057638A JP 2010057638 A JP2010057638 A JP 2010057638A JP 5011560 B2 JP5011560 B2 JP 5011560B2
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- short wavelength
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- photosensitive resin
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- 239000011230 binding agent Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
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- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 claims description 2
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
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- 239000011737 fluorine Substances 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
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- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- QGVQVNIIRBPOAM-UHFFFAOYSA-N dodecyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)OCCCCCCCCCCCC)=CC=CC2=C1 QGVQVNIIRBPOAM-UHFFFAOYSA-N 0.000 description 1
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- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- FKIRSCKRJJUCNI-UHFFFAOYSA-N ethyl 7-bromo-1h-indole-2-carboxylate Chemical compound C1=CC(Br)=C2NC(C(=O)OCC)=CC2=C1 FKIRSCKRJJUCNI-UHFFFAOYSA-N 0.000 description 1
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- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
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- 238000013007 heat curing Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical group 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
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- 239000007788 liquid Substances 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
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
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- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- ZZSKMNCIAKKVRB-UHFFFAOYSA-N morpholin-4-yl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCOCC1 ZZSKMNCIAKKVRB-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
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- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-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
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
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- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 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
- 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
- 239000000047 product Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 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
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
Description
[前記式(1)中、R1、R2、R3はそれぞれ独立に、水素原子、R、OR、COR、SR、CONRR’またはCNであり、R及びR’は炭素原子数1〜8のアルキル基、炭素原子数6〜12のアリール基、炭素原子数7〜13のアラルキル基または炭素原子数5〜7の複素環基を示し、これらはハロゲン原子または複素環基で置換または非置換され、これらのうち、アルキル基及びアラルキル基のアルキレン部分は不飽和結合、エーテル結合、チオエーテル結合、エステル結合によって連結されることができ、前記R及びR’は一緒に環を形成することができる。R4、R5、R6、R7はそれぞれ独立に水素原子、ハロゲン原子または炭素原子数1〜8のアルキル基を示し、R8は炭素原子数0〜10のアルキル基を示し、Y1、Y2、Y3はそれぞれ独立に酸素原子または硫黄原子を示し、Xはハロゲン原子または炭素原子数1〜8のアルキル基を示す。]
[前記式(2)中、R1はグリシジル基、(メタ)アクリロイル基、アミノプロピル基、メルカプトプロピル基、シアノプロピル基及びイソシアネートプロピル基からなるグループから選択される何れか一つの有機官能基であるか、前記グループから選択される何れか一つの有機官能基を有する炭素原子数1〜20の脂肪族または芳香族炭化水素であり、R2は水素原子、メチル基、エチル基またはヒドロキシ基であり、nは1〜13の整数である。]
本発明に係る短波長レーザ露光装置用着色感光性樹脂組成物は、光重合開始剤(A)として下記式(1)のオキシムエステル系光重合開始剤を含む。
[前記式(1)中、R1、R2、R3はそれぞれ独立に、水素原子、R、OR、COR、SR、CONRR’またはCNであり、R及びR’は炭素原子数1〜8のアルキル基、炭素原子数6〜12のアリール基、炭素原子数7〜13のアラルキル基または炭素原子数5〜7の複素環基を示し、これらはハロゲン原子または複素環基で置換または非置換され、これらのうちアルキル基及びアラルキル基のアルキレン部分は、不飽和結合、エーテル結合、チオエーテル結合、エステル結合によって連結されることができ、前記R及びR’は一緒に環を形成することができる。R4、R5、R6、R7はそれぞれ独立に水素原子、ハロゲン原子または炭素原子数1〜8のアルキル基を示し、R8は炭素原子数0〜10のアルキル基を示し、Y1、Y2、Y3はそれぞれ独立に酸素原子または硫黄原子を示し、Xはハロゲン原子または炭素原子数1〜8のアルキル基を示す。]
本発明に係る短波長レーザ露光装置用着色感光性樹脂組成物はシリコン化合物(B)を含む。
[前記式(2)中、R1はグリシジル基、(メタ)アクリロイル基、アミノプロピル基、メルカプトプロピル基、シアノプロピル基及びイソシアネートプロピル基からなるグループから選択される何れか一つの有機官能基であるか、前記グループから選択される何れか一つの有機官能基を有する炭素原子数1〜20の脂肪族または芳香族炭化水素であり、R2は水素原子、メチル基、エチル基またはヒドロキシ基であり、nは1〜13の整数である。]
本発明の短波長レーザ露光装置用着色感光性樹脂組成物に含有される結合剤樹脂(C)は、着色材料(E)に対する結合剤樹脂として作用するものであって、カラーフィルタの製造のための現像段階で使用されたアルカリ性現像液に溶解可能な重合体であれば何れも使用することができる。
前記結合剤樹脂としては、例えば(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/ポリスチレン巨大単量体共重合体、(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)アクリレート巨大単量体共重合体、(メタ)アクリル酸/ベンジル(メタ)アクリレート/ポリスチレン巨大単量体共重合体、(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)アクリレート巨大単量体共重合体、(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/ポリスチレン巨大単量体共重合体、(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)アクリレート巨大単量体共重合体、(メタ)アクリル酸/スチレン/ベンジル(メタ)アクリレート/N‐フェニルマレイミド共重合体、(メタ)アクリル酸/コハク酸モノ(2‐アクリロイルオキシ)/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/コハク酸モノ(2‐アクリロイルオキシエチル)/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/ベンジル(メタ)アクリレート/N‐フェニルマレイミド/スチレン/グリセロールモノ(メタ)アクリレート共重合体などがある。これらのうち(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/ベンジル(メタ)アクリレート/スチレン共重合体、(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/メチル(メタ)アクリレート/スチレン共重合体が好ましく使用される。
本発明の短波長レーザ露光装置用着色感光性樹脂組成物に含有される光重合性化合物(D)は、光及び光重合開始剤の作用で重合することができる化合物であって、単官能単量体、2官能単量体及びその他の多官能単量体を含むことができる。
これらのうち2官能以上の多官能単量体が好ましく使用される。
本発明で使用される着色材料(E)はその色調が限定されず、得られるカラーフィルタの用途によって選定可能である。具体的に、顔料、染料または天然色素のうち何れか一つであってもよく、その中でも耐熱性、発色性が優れていることから有機顔料が好ましく使用される。有機顔料及び無機顔料として、具体的にはカラーインデックス(The Society of Dyers and Colourists出版)においてピグメント(Pigment)に分類されている化合物を使用することができる。
本発明の短波長レーザ露光装置用着色感光性樹脂組成物に含有される溶剤(F)は、特に制限されず、着色感光性樹脂組成物の分野で使用されている各種有機溶剤を使用することができる。
これらの溶剤(F)は、それぞれ単独でまたは2種以上混合して使用することができる。
撹拌機、温度計及びpHメータを備えた反応容器に3‐メタクリルオキシプロピルトリメトキシシラン(MTMS:GE‐東芝製A‐174)80mlを入れ、メタノール15mlにpH2.5のマロン酸水溶液5mlを混合製造した混合液20mlを滴下漏斗に入れて、反応容器を撹拌しながら常温でメタノールとマロン酸水溶液混合液を30分間滴下させた。滴下終了後、常温を維持しながら2時間撹拌した。2時間の撹拌後、減圧下で溶媒を取り除いた。無水硫酸マグネシウムで残存する蒸留水を脱水し、無水硫酸マグネシウムを濾過分別した。上記の過程で、最終的に得られるシリコン化合物は、密着性増進に最適の性能を示す無色の粘性液体であるシリコンゾル状態で存在するようになる。
合成例1と同様の容器に、3‐メタクリルオキシプロピルトリメトキシシランを3‐グリシドキシプロピルトリメトキシシラン(GPTMS:GE‐東芝製A‐187)に変更したこと以外には合成例1と同様に合成した。
表1及び表2に記載の各成分を混合溶解して光重合組成物を製造した。
(A‐2)4,4’‐ビス(ジエチルアミノ)ベンゾフェノン[EAB‐F;保土ヶ谷化学(株)製]
(A‐3)(E)‐1‐(1‐(6‐(4‐((2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)methoxy)‐2‐methylbenzoyl)‐9‐ethyl‐9,9a‐dihydro‐4aH‐carbazol‐3‐yl)ethylideneaminooxy)ethanone[N‐1919<製造社:株式会社ADEKA>]
(A‐4)トリクロロメチルトリアジン
(B‐1)シリコン化合物<合成例1>
(B‐2)シリコン化合物<合成例2>
(B‐3)シリコン化合物:3‐メタクリルオキシプロピルトリメトキシシラン
(B‐4)シリコン化合物:ビニルトリメトキシシラン
(C‐1)メタクリル酸とベンジルメタクリレートとの共重合体(メタクリル酸単位とベンジルメタクリレート単位との比は、モル比で25:75、酸価は82、ポリスチレン換算重量平均分子量は28000)
(D‐1)ジペンタエリスリトールヘキサアクリレート
(E‐1)C.I.ピグメントレッド254
(E‐2)C.I.ピグメントレッド177
(E‐3)C.I.ピグメントイエロー150
(F‐1)プロピレングリコールモノメチルエーテルアセテート
(F‐2)3‐エトキシプロピオン酸エチル
(F‐3)メトキシプロパノール
前記参考例1、実施例2〜5と比較例1〜4のカラーフィルタ用着色感光性樹脂組成物をスピンコーティング法でガラス基板上に塗布した後、加熱板上に載置し、100℃の温度で3分間維持して薄膜を形成した。続いて、前記薄膜上に透過率1〜100%の範囲で階段状に変化させるフォトマスクとの間隔を100umにし、露光量30mJ/cm2を照射し、1umから100umまでのライン/スペースパターンを有する試験フォトマスクを載置し、試験フォトマスクとの間隔を200umにし、露光量30mJ/cm2を照射した。
現像しても表面粗さのないパターンを形成するために必要な最低必要露光量として、
○:15mJ以下で表面粗さ無し
△:15mJ超過30mJ以下
X:30mJ超過
画素表面の形状をSEM(10000倍率)を用いて観察した。
○:パターンプロファイル(Pattern profile)及び直進性良好
△:パターンプロファイル(Pattern profile)良好
X:パターンプロファイル(Pattern profile)不良
画素表面の形状を顕微鏡(500倍率)を用いて観察した。
○:パターンエッジ(Pattern edge)部のパターン剥離良好
△:パターンエッジ(Pattern edge)部のパターン剥離普通
X:パターンエッジ(Pattern edge)部のパターン剥離不良
画素の透過率測定及び表面形状を顕微鏡(500倍率)を用いて観察した。
○:残渣、透過率良好
△:残渣良好、透過率不良
X:残渣、透過率不良
Claims (7)
- 式(1)で表示されるオキシムエステル系重合開始剤を含む光重合開始剤(A)、式(2)で表示されるシリコン化合物(B)、結合剤樹脂(C)、光重合性化合物(D)、着色材料(E)及び溶剤(F)を含む短波長レーザ露光装置用着色感光性樹脂組成物であり、
前記光重合開始剤(A)は、前記短波長レーザ露光装置用着色感光性樹脂組成物中の固形分に対して質量分率で3〜20質量%含まれ、前記式(1)の光重合開始剤は、短波長レーザ露光装置用着色感光性樹脂組成物中の光重合開始剤に対して質量分率で60〜70質量%含まれることを特徴とする短波長レーザ露光装置用着色感光性樹脂組成物。
- 前記シリコン化合物(B)は、メタクリロキシメチルトリエトキシシラン、メタクリロキシメチルトリメトキシシラン、3‐メタクリロキシプロピルトリクロロシラン、3‐メタクリロキシプロピルトリメトキシシラン、3‐メタクリロキシプロピルトリエトキシシラン、3‐アクリロキシプロピルトリメトキシシラン、3‐アクリロキシプロピルトリクロロシランからなるグループのうち選択された少なくとも一つの化合物をゾル‐ゲル工程を経て得られたことを特徴とする、請求項1に記載の短波長レーザ露光装置用着色感光性樹脂組成物。
- 前記シリコン化合物(B)は、短波長レーザ露光装置用着色感光性樹脂組成物中の固形分に対して質量分率で0.1〜2.0質量%含まれることを特徴とする、請求項1に記載の短波長レーザ露光装置用着色感光性樹脂組成物。
- 前記短波長レーザ露光装置は、露光波長が300nm〜400nmの短波長であることを特徴とする、請求項1に記載の短波長レーザ露光装置用着色感光性樹脂組成物。
- 前記短波長レーザ露光装置は、露光波長が308nmまたは355nmであることを特徴とする、請求項1に記載の短波長レーザ露光装置用着色感光性樹脂組成物。
- 請求項1〜5のいずれか一項に記載の短波長レーザ露光装置用着色感光性樹脂組成物を所定のパターンに形成した後、露光及び現像して形成されるカラー層を含んで成ることを特徴とするカラーフィルタ。
- 請求項6に記載のカラーフィルタを含むことを特徴とする液晶表示装置。
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JP2003177227A (ja) * | 2001-12-10 | 2003-06-27 | Toppan Printing Co Ltd | カラーフィルターの製造方法およびそれに用いる黒色感光性樹脂組成物およびカラーフィルター |
JP3992725B2 (ja) * | 2004-08-20 | 2007-10-17 | 株式会社Adeka | オキシムエステル化合物及び該化合物を含有する光重合開始剤 |
JP2007041158A (ja) | 2005-08-01 | 2007-02-15 | Fujifilm Holdings Corp | カラーフィルタ作成用の光硬化性樹脂着色組成物、光硬化性樹脂転写フィルム、及びそれらを用いて製造するカラーフィルタの製造方法 |
TWI437280B (zh) * | 2006-06-23 | 2014-05-11 | Fujifilm Corp | 化合物、感光性組成物、硬化性組成物、彩色濾光片用硬化性組成物、彩色濾光片及其製法 |
JP2008122750A (ja) | 2006-11-14 | 2008-05-29 | Toray Ind Inc | カラーフィルター用感光性レジスト組成物およびカラーフィルター |
US8133656B2 (en) * | 2006-12-27 | 2012-03-13 | Adeka Corporation | Oxime ester compound and photopolymerization initiator containing the same |
JP5191241B2 (ja) * | 2007-01-12 | 2013-05-08 | 東洋インキScホールディングス株式会社 | 着色組成物およびカラーフィルタの製造方法 |
JP5109437B2 (ja) * | 2007-03-27 | 2012-12-26 | Jsr株式会社 | 着色層形成用感放射線性組成物、カラーフィルタおよびカラー液晶表示素子 |
KR20080107128A (ko) * | 2007-06-05 | 2008-12-10 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러필터, 및 이를 구비한액정표시장치 |
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2009
- 2009-03-16 KR KR1020090022098A patent/KR101403153B1/ko not_active IP Right Cessation
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2010
- 2010-03-11 TW TW099107170A patent/TWI402620B/zh not_active IP Right Cessation
- 2010-03-15 JP JP2010057638A patent/JP5011560B2/ja not_active Expired - Fee Related
- 2010-03-16 CN CN201010132318A patent/CN101840155A/zh active Pending
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KR20100103987A (ko) | 2010-09-29 |
TWI402620B (zh) | 2013-07-21 |
KR101403153B1 (ko) | 2014-06-09 |
CN101840155A (zh) | 2010-09-22 |
JP2010217895A (ja) | 2010-09-30 |
TW201037459A (en) | 2010-10-16 |
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