JP5115046B2 - 感光性黒色組成物およびカラーフィルタ - Google Patents
感光性黒色組成物およびカラーフィルタ Download PDFInfo
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- JP5115046B2 JP5115046B2 JP2007157315A JP2007157315A JP5115046B2 JP 5115046 B2 JP5115046 B2 JP 5115046B2 JP 2007157315 A JP2007157315 A JP 2007157315A JP 2007157315 A JP2007157315 A JP 2007157315A JP 5115046 B2 JP5115046 B2 JP 5115046B2
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- Prior art keywords
- carbon black
- dispersant
- photopolymerization initiator
- general formula
- black composition
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 claims abstract description 47
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- 239000000049 pigment Substances 0.000 claims abstract description 21
- 238000010521 absorption reaction Methods 0.000 claims abstract description 17
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- 239000003999 initiator Substances 0.000 claims description 49
- 239000006185 dispersion Substances 0.000 claims description 48
- 229920005989 resin Polymers 0.000 claims description 41
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- 239000000975 dye Substances 0.000 claims description 20
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- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000011164 primary particle Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000002923 oximes Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 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
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- SKEQOTBKQUCUGK-UHFFFAOYSA-N o-(2-hydroxyethyl) propanethioate Chemical compound CCC(=S)OCCO SKEQOTBKQUCUGK-UHFFFAOYSA-N 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-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
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 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 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
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- 239000011118 polyvinyl acetate Substances 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Images
Classifications
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- 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
-
- 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
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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
- G03F7/0005—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
- 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
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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
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- 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
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Paints Or Removers (AREA)
- Liquid Crystal (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
カーボンブラックを用いた分散体においては、一般的にカーボンブラックのストラクチャー(一次凝集体)が大きい程、分散が容易と言われているため、ストラクチャーが大きいカーボンブラックを好んで使用される傾向がある。しかし、塗膜中ではこのストラクチャーによる構造が塗膜形成時の充填性を妨げ、遮光剤以外の空孔の多い塗膜となる。特にカーボンブラックの含有量が増大するとストラクチャーがカーボンブラックの充填性に与える影響は大きくなる。その結果同じ含有量でもカーボンブラックの種類と分散性によって充填性が変わり、遮光性が異なる結果を与える。
一般式(1):
(HOOC−)m−R1−(−COO−[−R3−COO−] n−R2)t
(式中、R1は4価のテトラカルボン酸化合物残基、R2はモノアルコール残基、R3はラクトン残基、mは2または3、nは1〜50の整数、tは(4−m)を表す。)
のいずれかの酸性分散剤であり、(c)色素誘導体が、下記一般式(2)で示される塩基性色素誘導体であることを特徴とする感光性黒色組成物に関する。
一般式(2):
一般式(3):
また、本発明は、(d)光重合開始剤が、オキシム系光重合開始剤、イミダゾール系光重合開始剤およびボレート系光重合開始剤から選ばれる少なくとも一種の光重合開始剤であることを特徴とする上記感光性黒色組成物に関する。
平均一次粒子径15〜25nm、比表面積100〜180m2/g、吸油量55cm3/100g以下であるカーボンブラックとしては、例えば、CABOT製のBLACK PEARLS L、三菱化学製のMA8、MCF88、#(1000,45,45L)、DEGUSSA製のSpecial Black550、Printex75、Printex55、コロンビヤン・カーボン製のRAVEN1250、1200等を挙げることができ、特に好ましくは、三菱化学製の#45、#45L、DEGUSSA製のPrintex55を用いることができる。
一般式(1):
(HOOC−)m−R1−(−COO−[−R3−COO−] n−R2)t
(式中、R1は4価のテトラカルボン酸化合物残基、R2はモノアルコール残基、R3はラクトン残基、mは2または3、nは1〜50の整数、tは(4−m)を表す。)
リン酸エステル系顔料分散剤としては、BYK−Chemie製Disperbyk−111、110等が挙げることができるが、特にこれらに限定されない。
一般式(2)
一般式(3)
ガス導入管、温度計、コンデンサ、攪拌機を備えた反応容器に、1−ドデカノール62.6部、ε−カプロラクトン287.4部、触媒としてモノブチルスズ(IV)オキシド0
.1部を仕込み、窒素ガスで置換し、120℃で4時間加熱、撹拌した。固形分測定により98%が反応したことを確認したのち、無水ピロメリット酸36.6部を加え、120℃で2時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認した後に反応を終了して分散剤を得た。得られた分散剤は常温で白色固形であり、酸価は49mgKOH/gであった。この分散剤を不揮発分が30%になるようにシクロヘキサノンを添加して分散剤溶液1を調製した。
(HOOC−)m−R1−(−COO−[−R3−COO−] n−R2)t
(式中、R1は4価のテトラカルボン酸化合物残基、R2はモノアルコール残基、R3はラクトン残基、mは2または3、nは1〜50の整数、tは(4−m)を表す。)
反応容器にプロピレングリコールモノメチルエーテルアセテート370部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度で下記モノマーおよび熱重合開始剤の混合物を1時間かけて滴下して重合反応を行った。
メチルメタクリレート 10.0部
n−ブチルメタクリレート 35.0部
2−ヒドロキシエチルメタクリレート 15.0部
2、2'−アゾビスイソブチロニトリル 4.0部
パラクミルフェノールエチレンオキサイド変性アクリレート 20.0部
(東亞合成社製「アロニックスM−110」)
カーボンブラック#45(三菱化学製,平均一次粒子径24nm,比表面積120m2/g,吸油量53cm3/100g)100部、下記式(19)に示す塩基性色素誘導体4部、下記一般式(1)で表される分散剤溶液1を14部、樹脂溶液1を56部混合し、シクロヘキサノンで希釈して最終固形分を20%とした。このものを、直径0.8mmのガラスビーズを用いペイントシェーカーにて2時間分散することにより、カーボンブラック分散体Aを調製した。
式(19):
(HOOC−)m−R1−(−COO−[−R3−COO−] n−R2)t
(式中、R1は4価のテトラカルボン酸化合物残基、R2はモノアルコール残基、R3はラクトン残基、mは2または3、nは1〜50の整数、tは(4−m)を表す。)
カーボンブラック分散体Aにおいて、カーボンブラックとしてカーボンブラック#45の代わりにカーボンブラック#45L(三菱化学製,平均一次粒子径24nm,比表面積125m2/g,吸油量45cm3/100g)を用いた以外は、同様の操作を行なってカーボンブラック分散体Bを調製した。
カーボンブラック分散体Aにおいて、カーボンブラックとしてカーボンブラック#45の代わりにPrintex55(DEGUSSA製,平均一次粒子径25nm,比表面積110m2/g,吸油量44cm3/100g)を用いた以外は、同様の操作を行なってカーボンブラック分散体Cを調製した。
カーボンブラック分散体Aにおいて、分散剤として分散剤溶液1の代わりにリン酸エステル系顔料分散剤Disperbyk−111(BYK Chemie製)を14.2部を用いてシクロヘキサノンで最終固形分20%に希釈した以外は、同様の操作を行なってカーボンブラック分散体Dを調製した。
カーボンブラック分散体Aにおいて、カーボンブラックとしてカーボンブラック#45の代わりにカーボンブラック#47(三菱化学製,平均一次粒子径23nm,比表面積132m2/g,吸油量64cm3/100g)100部を用いた以外は、同様の操作を行なってカーボンブラック分散体Eを調製した。
カーボンブラック分散体Aの調製において、カーボンブラックとしてカーボンブラック#45の代わりにREGAL250R(CABOT製,平均一次粒子径35nm,比表面積50m2/g,吸油量46cm3/100g)100部を用いた以外は、カーボンブラック分散体Aの調整と同様の操作を行ってカーボンブラック分散体Fを調製した。
カーボンブラック分散体Aにおいて、分散剤として分散剤溶液1の代わりに塩基性櫛形顔料分散剤Solsperse28000(日本ルーブリゾール製)14.2部を用いてシクロヘキサノンで最終固形分20%に希釈した以外は、同様の操作を行なってカーボンブラック分散体Gを調製した。
カーボンブラック分散体Aにおいて、色素誘導体として塩基性色素誘導体の代わりに酸性色素誘導体Solsperse5000(日本ルーブリゾール製)を用いた以外は、同様の操作を行なってカーボンブラック分散体Hを調製した。
カーボンブラック分散体Aにおいて、分散剤として分散剤溶液1の代わりに樹脂溶液1を用いた以外は、同様の操作を行なってカーボンブラック分散体Iを調製した。
カーボンブラック分散体Aにおいて、塩基性色素誘導体の代わりにカーボンブラック#45を用いた以外は、同様の操作を行なってカーボンブラック分散体Jを調製した。
[実施例1]
カーボンブラック分散体Aに対して表1に示す配合組成で、混合物を均一になるように攪拌混合した後、2μmのフィルタで濾過して、カーボンブラックの含有量の異なる感光性黒色組成物を得た(実施例1a〜d)。
光重合開始剤A:式(14)で示されるオキシム系光重合開始剤(エタノン, 1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)、チバ・スペシャルティ・ケミカルズ社製「イルガキュア OXE02」)
溶剤 :シクロヘキサノン
実施例1と同様にして表2に示すカーボンブラック分散体を用いてそれぞれに対応する感光性黒色組成物を得た。
感光性黒色組成物をスピンコート法により10cm×10cmのガラス基板に塗工した後、70℃で15分の乾燥により乾燥膜厚約1μmの塗膜を作成し、露光工程は行わずに230℃で1時間加熱した後、膜厚を測定した。このようにして得られた感光性黒色組成物塗工基板の光学濃度(OD)を、マクベス濃度計(GretagMacbeth D200−II)により測定し、測定光学濃度(OD)を測定膜厚で除し、単位膜厚当たりの光学濃度(OD/μm)を求めた。
ブラックマトリックスのパターン形状の評価は、[遮光性]評価と同様の方法で塗膜を作成した。その後、超高圧水銀ランプを用い、フォトマスクを介して露光量120〜200mJ/cm2の紫外線を露光した。炭酸ナトリウム水溶液を用いてスプレー現像した後、イオン交換水で洗浄することで未露光部分を取り除いた。なお、フォトマスクには10μmのマスクパターンを使用し、ストライプ状のブラックマトリックスパターンを形成した。作成されたパターン形状を、光学顕微鏡あるいは電子線走査顕微鏡で観察し、直線性を観察した。直線部分にギザツキが見られない場合にはパターン形状○、直線部分の一部にギザツキが見られる場合はパターン形状△、直線部分の全体にわたってギザツキが多数見られる場合はパターン形状×として評価した。
Claims (5)
- (a)カーボンブラック、(b)分散剤、(c)色素誘導体、(d)光重合開始剤、 および(e)エチレン性不飽和化合物を含有してなる感光性黒色組成物において、(a)カーボンブラックの平均一次粒子径が15〜25nm、比表面積100〜180m2/g、フタル酸ジブチル(DBP)吸油量が55cm3/100g以下であり、(b)分散剤がリン酸エステル系顔料分散剤または下記一般式(1)
一般式(1):
(HOOC−)m−R1−(−COO−[−R3−COO−] n−R2)t
(式中、R1は4価のテトラカルボン酸化合物残基、R2はモノアルコール残基、R3はラクトン残基、mは2または3、nは1〜50の整数、tは(4−m)を表す。)
のいずれかの酸性分散剤であり、(c)色素誘導体が、下記一般式(2)で示される塩基性色素誘導体であることを特徴とする感光性黒色組成物。
一般式(2):
一般式(3):
- (f)樹脂を含有することを特徴とする請求項1に記載の感光性黒色組成物。
- (b)分散剤および(f)樹脂の合計重量(P)に対する(e)エチレン性不飽和化合物の重量(M)の比率(M/P)が、0.10〜0.70であることを特徴とする請求項2に記載の感光性黒色組成物。
- (d)光重合開始剤が、オキシム系光重合開始剤、イミダゾール系光重合開始剤およびボレート系光重合開始剤から選ばれる少なくとも一種の光重合開始剤であることを特徴とする請求項1〜3いずれか1項に記載の感光性黒色組成物。
- 透明基板上に、請求項1〜4いずれか1項に記載の感光性黒色組成物を用いて形成されたブラックマトリックスを備えることを特徴とするカラーフィルタ。
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