WO2022224779A1 - 有機el表示装置 - Google Patents
有機el表示装置 Download PDFInfo
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- WO2022224779A1 WO2022224779A1 PCT/JP2022/016191 JP2022016191W WO2022224779A1 WO 2022224779 A1 WO2022224779 A1 WO 2022224779A1 JP 2022016191 W JP2022016191 W JP 2022016191W WO 2022224779 A1 WO2022224779 A1 WO 2022224779A1
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- Prior art keywords
- colorant
- pigment
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- organic
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- 239000003086 colorant Substances 0.000 claims abstract description 225
- -1 oxime ester Chemical class 0.000 claims abstract description 191
- 229920005989 resin Polymers 0.000 claims abstract description 118
- 239000011347 resin Substances 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 238000004040 coloring Methods 0.000 claims abstract description 75
- 239000000178 monomer Substances 0.000 claims abstract description 55
- 239000003999 initiator Substances 0.000 claims abstract description 54
- 239000000758 substrate Substances 0.000 claims abstract description 29
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 12
- 239000010703 silicon Substances 0.000 claims abstract description 12
- 239000000049 pigment Substances 0.000 claims description 156
- 239000002904 solvent Substances 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 238000002834 transmittance Methods 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 230000003595 spectral effect Effects 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 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 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000001018 xanthene dye Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000011161 development Methods 0.000 abstract description 19
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- 238000000034 method Methods 0.000 description 55
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- 239000002270 dispersing agent Substances 0.000 description 29
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- 239000000975 dye Substances 0.000 description 18
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 18
- 238000002156 mixing Methods 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 16
- 125000002091 cationic group Chemical group 0.000 description 16
- 238000002347 injection Methods 0.000 description 16
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- 239000000126 substance Substances 0.000 description 16
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- 239000011324 bead Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- 239000010935 stainless steel Substances 0.000 description 13
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- 239000001052 yellow pigment Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000001055 blue pigment Substances 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
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- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000006870 function Effects 0.000 description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 9
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- 239000001054 red pigment Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 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 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 230000032258 transport Effects 0.000 description 8
- 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 7
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 7
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 6
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- 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 5
- DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 5
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- GAMLUOSQYHLFCT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-3-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1(CC)COC1 GAMLUOSQYHLFCT-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UHGYPKHARWLOQB-UHFFFAOYSA-N trihydroxy-(13-phenyltridecyl)-tridecyl-lambda5-phosphane Chemical compound CCCCCCCCCCCCCP(O)(O)(O)CCCCCCCCCCCCCC1=CC=CC=C1 UHGYPKHARWLOQB-UHFFFAOYSA-N 0.000 description 1
- QHCNTMCHBZHBDY-UHFFFAOYSA-N trihydroxy-(6-methylheptyl)-phenyl-lambda5-phosphane Chemical compound CC(C)CCCCCP(O)(O)(O)C1=CC=CC=C1 QHCNTMCHBZHBDY-UHFFFAOYSA-N 0.000 description 1
- SFESXIFARCRODZ-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-phenyl-$l^{5}-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C1=CC=CC=C1 SFESXIFARCRODZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
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- 239000000984 vat dye Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
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- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
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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
- G03F7/0005—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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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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
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/35—Devices specially adapted for multicolour light emission comprising red-green-blue [RGB] subpixels
Definitions
- the present invention relates to an organic EL display device.
- organic EL which is a self-luminous element
- development and mass production of display devices using (organic electroluminescence) are progressing.
- display devices using (organic electroluminescence) are progressing.
- microdisplays high-definition and small displays of about 0.5 inches (hereinafter referred to as microdisplays) such as head-mounted displays and electronic viewfinders.
- the display method of the organic EL display includes a method of forming a white light-emitting layer and using a color filter to express colors such as RGB, and a method of vapor-depositing a light-emitting layer that emits each color such as RGB to express colors.
- a color filter to express colors
- RGB color filter
- the pixel size of a microdisplay is as small as 1 ⁇ m to 5 ⁇ m. Therefore, the conventional method of fabricating organic EL elements and color filters on separate substrates and bonding them together results in lower precision and color shifts. occur. Therefore, a method of forming a color filter on an organic EL element has been proposed.
- Patent Document 1 proposes a method of increasing curability at low temperatures by using an alkali-soluble resin containing an epoxy group and a coloring composition containing an amine compound as a curing agent.
- the addition of an amine compound to the coloring composition may reduce the transmittance of the color filter.
- Patent Document 2 proposes a method of curing at a low temperature by using an oxetane compound and a benzophenone-based compound having a peroxide skeleton as a thermal polymerization initiator.
- the curing temperature is 150° C. Considering the heat resistance of the organic EL element, further low-temperature curability is required. Further, in order to achieve high color reproducibility, it is necessary to control the spectral transmittance of the color filter by blending the coloring agent, and to increase the concentration of the coloring agent in order to make the film thinner. In the methods of Patent Documents 1 and 2, when the concentration of the coloring agent is high, it is very difficult to achieve sufficient sensitivity for patterning due to insufficient photocurability. There have been problems such as a decrease in pixel linearity (improper pixel linearity) and peeling of pixels during the development process (improper adhesion). In addition, there is a problem that the coloring agents that can be used are limited.
- the present invention provides an organic EL display having a color filter which has high luminance and high color reproducibility, good pixel adhesion in the development process even when the colorant concentration is high, and good pixel linearity.
- the purpose is to provide an apparatus.
- the organic EL display device is An organic EL display device having an organic EL layer and a color filter on a silicon substrate on which driving elements are formed, the color filter has pixels including red pixels, green pixels, and blue pixels;
- the film thickness of the pixel is 1.5 ⁇ m
- the spectral transmittance of the red pixel has a maximum light transmittance of 0.5% or less in a wavelength range of 450 nm to 560 nm, a 50% half-value wavelength of 593 nm to 603 nm, and a maximum light transmittance of a wavelength range of 600 nm to 700 nm.
- the maximum transmittance of light in the wavelength range of 400 nm to 470 nm is 2% or less
- the maximum transmittance of light in the wavelength range of 525 to 535 nm is 67% or more
- the 50% half-value wavelength on the short wavelength side is 497.
- the spectral transmittance of the blue pixel has a maximum light transmittance of less than 20% in a wavelength range of 500 nm to 560 nm
- the pixel is a cured product of a photosensitive coloring composition containing a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D),
- the coloring agent (A) contains Pigment Red 177 and other coloring agents
- the colorant (A) contains Pigment Yellow 185 and one or more selected from the group consisting of Pigment Green 36, Pigment Green 62, Pigment Green 63 and Pigment Green 59, and contains other colorants.
- the content of Pigment Yellow 185 in the colorant (A) of the green pixel is 49% by weight to 59% by weight, said blue pixels comprising Pigment Blue 15:6 and other colorants;
- the other coloring agent contains one or more selected from the group consisting of Pigment Red 254 and Pigment Yellow 139, in the green pixel, the other colorant comprises Pigment Blue 15:3;
- the other coloring agent contains one or more selected from the group consisting of Pigment Violet 23 and xanthene dyes,
- the photopolymerizable monomer (B) contains a compound represented by the following general formula (1)
- the photopolymerization initiator (C) contains an oxime ester photopolymerization initiator.
- the cured product constituting the red pixel contains colorant (A-1) Pigment Red 177, colorant (A-2) Pigment Red 254, and colorant (A-3) Pigment Yellow 139, In the colorant (A) in the red pixel, The content of the coloring agent (A-1) is 55% to 65% by weight, The content of the coloring agent (A-2) is 15% by weight to 25% by weight, and the content of the coloring agent (A-3) is 15% to 25% by weight, The cured product constituting the green pixel includes colorant (A-4) Pigment Yellow 185, colorant (A-5) Pigment Green 36, colorant (A-6) Pigment Green 62, and colorant (A-11).
- the content of the compound represented by the general formula (1) is 50% by weight or more with respect to the total amount of the photopolymerizable monomer (B).
- the oxime ester photopolymerization initiator is a compound represented by the following general formula (2).
- R 1 represents an optionally substituted alkyl group having 1 to 20 carbon atoms
- R 2 represents represents an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group
- each of R 3 to R 10 independently has a hydrogen atom and a substituent; represents an alkyl group having 1 to 20 carbon atoms which may be represents a good aryl group.
- the oxime ester photopolymerization initiator is a compound represented by the following general formula (3).
- W 1 and W 2 each independently represent a carbonyl bond (--CO--) or a single bond, and at least one of W 1 and W 2 is a carbonyl bond (--CO--).
- R a is an alkyl group having 2 to 6 carbon atoms
- R b is an alkyl group having 4 to 10 carbon atoms
- R c contains at least a hydrocarbon ring or heterocyclic ring and further has 1 to 4 carbon atoms.
- R b and R c are substituents different from each other.
- R d and R e are each independently an alkyl group having 1 to 6 carbon atoms.
- the resin (D) contains a photosensitive resin.
- the photosensitive resin contains a vinyl polymer having an aromatic carboxylic acid at the end.
- the photosensitive coloring composition further contains a solvent, and the solvent contains an ether ester solvent and an ether alcohol solvent.
- an organic EL display device having a color filter which has high luminance and high color reproducibility, good pixel adhesion in the development process even when the colorant concentration is high, and good pixel linearity. can do.
- FIG. 1 is a schematic cross-sectional view of the present organic EL display device.
- the "50% half-value wavelength” represents the wavelength (nm) at which the spectral transmittance is 50% in the wavelength region from 400 nm to 700 nm.
- “Short wavelength side 50% half-value wavelength” represents the wavelength (nm) when the spectral transmittance becomes 50% for the first time when the measurement is started from the short wavelength (400 nm) and scanned to the long wavelength side.
- “Side 50% half-value wavelength” represents the wavelength (nm) at which the spectral transmittance becomes 50% for the first time when the measurement is started from the long wavelength (700 nm) and scanned to the short wavelength side.
- “(Meth)acryloyl”, “(meth)acryl”, “(meth)acrylic acid”, “(meth)acrylate”, or “(meth)acrylamide” unless otherwise specified , “acryloyl and/or methacryloyl”, “acrylic and/or methacrylic”, “acrylic acid and/or methacrylic acid”, “acrylate and/or methacrylate”, or “acrylamide and/or methacrylamide”.
- C.I mentioned in this specification means a color index (C.I.).
- the organic EL display device (hereinafter also referred to as the present organic EL display device)
- An organic EL display device having an organic EL layer and a color filter on a silicon substrate on which driving elements are formed, the color filter has pixels including red pixels, green pixels, and blue pixels;
- the film thickness of the pixel is 1.5 ⁇ m
- the spectral transmittance of the red pixel has a maximum light transmittance of 0.5% or less in a wavelength range of 450 nm to 560 nm, a 50% half-value wavelength of 593 nm to 603 nm, and a maximum light transmittance of a wavelength range of 600 nm to 700 nm.
- the maximum transmittance of light in the wavelength range of 400 nm to 470 nm is 2% or less
- the maximum transmittance of light in the wavelength range of 525 to 535 nm is 67% or more
- the 50% half-value wavelength on the short wavelength side is 497.
- the spectral transmittance of the blue pixel has a maximum light transmittance of less than 20% in a wavelength range of 500 nm to 560 nm
- the pixel is a cured product of a photosensitive coloring composition containing a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D),
- the coloring agent (A) contains Pigment Red 177 and other coloring agents
- the colorant (A) contains Pigment Yellow 185 and one or more selected from the group consisting of Pigment Green 36, Pigment Green 62, Pigment Green 63 and Pigment Green 59, and contains other colorants.
- the content of Pigment Yellow 185 in the colorant (A) of the green pixel is 49% by weight to 59% by weight, said blue pixels comprising Pigment Blue 15:6 and other colorants;
- the other coloring agent contains one or more selected from the group consisting of Pigment Red 254 and Pigment Yellow 139, in the green pixel, the other colorant comprises Pigment Blue 15:3;
- the other coloring agent contains one or more selected from the group consisting of Pigment Violet 23 and xanthene dyes,
- the photopolymerizable monomer (B) contains a compound represented by the following general formula (1)
- the photopolymerization initiator (C) contains an oxime ester photopolymerization initiator.
- the organic EL display device since the pixels of the color filter are a cured product of the specific photosensitive coloring composition, even when the color filter is formed on the organic EL layer, the organic EL layer It is possible to obtain a high-quality organic EL display device that can suppress the influence of heat, has high luminance and high color reproducibility, and is excellent in pixel linearity.
- the organic EL display device uses pixels whose color filters have the above-mentioned specific spectral characteristics, so that colors connecting R (red), G (green), and B (blue) in the xy chromaticity diagram can be obtained. The area of the region defined by the triangle is expanded, and the display device has a wide color reproduction range (that is, high color reproducibility).
- the photosensitive coloring composition for pixel formation will be described first, and then the structure of the organic EL display device will be described.
- Each pixel of the color filter is a cured product of a photosensitive coloring composition containing a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D).
- the photopolymerizable monomer (B) contains at least a compound represented by general formula (1)
- the photopolymerization initiator (C) contains at least an oxime ester photopolymerization initiator. characterized by comprising
- the photosensitive coloring composition contains at least a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), and if necessary, other It may contain the components of The details of each component will be described below.
- the coloring agent (A) adjusts the color tone of the pixels of the color filter so that specific spectral characteristics described later can be obtained. It can be selected and used as appropriate.
- the pigment both organic pigments and inorganic pigments can be suitably used.
- the present photosensitive coloring composition is excellent in low-temperature curability, even dyes with low heat resistance compared to pigments can be suitably used.
- Inorganic pigments include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron oxide (III)), cadmium red, ultramarine blue, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic Metal oxide powders such as iron black, titanium oxide and iron tetroxide, metal sulfide powders, metal powders, and the like can be used. Inorganic pigments are preferably used in combination with organic pigments in order to ensure good applicability, sensitivity, developability, etc. while maintaining a balance between chroma and lightness.
- any of acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, and the like can be used as dyes.
- it may be in the form of a lake pigment obtained by converting a derivative of these or a dye into a lake.
- the colorant (A) preferably contains a pigment, and more preferably an organic pigment, because it has high color developability, excellent heat resistance, and particularly excellent thermal decomposition resistance.
- the coloring agent (A) will be described below more specifically for each color.
- This organic EL display device uses C.I. I. Pigment Red 177 (also referred to as coloring agent (A-1)) is used in combination with other coloring agents.
- C.I. I. Pigment Red 177 also referred to as coloring agent (A-1)
- the spectral transmittance of the red pixel when the film thickness of the pixel is 1.5 ⁇ m
- the maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.5. % or less
- the maximum transmittance of light having a half-value wavelength of 593 nm to 603 nm and a wavelength of 600 nm to 700 nm is easily adjusted to 80% or more and less than 100%.
- a red pigment, an orange pigment, or a yellow pigment is preferable as the other coloring agent in the red pixel coloring agent.
- Other colorants may be used singly or in combination of two or more.
- red pigment examples include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81: 3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200,
- orange pigment examples include C.I. I. Pigment Orange 36, 38, 43, 51, 55, 59, 61 and the like.
- yellow pigment examples include C.I. I. Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95,97,100,101,104,105,108,109,110,111,116,117,119,120,126,127,127:1,128,129,133,134,136,138,139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191
- pigment red 254 colorant (A -2)
- Pigment Yellow 139 colorant (A-3)
- the content of the colorant (A-1) in the colorant (A) is 55% to 65% by weight.
- the content of the coloring agent (A-2) is preferably 15% to 25% by weight
- the content of the coloring agent (A-3) is preferably 15% to 25% by weight.
- the colorant for green pixels is C.I. I. Pigment Yellow 185 (also referred to as colorant (A-4)) and one or more selected from the group consisting of Pigment Green 36, Pigment Green 62, Pigment Green 63 and Pigment Green 59, in the colorant (A) Pigment Yellow 185 content of 49% to 59% by weight.
- the spectral transmittance of the green pixel when the film thickness of the pixel is 1.5 ⁇ m is 2% or less in the wavelength range of 400 nm to 470 nm.
- a green pigment, a yellow pigment, or a blue pigment is preferable as the other coloring agent in the green pixel coloring agent.
- Other colorants may be used singly or in combination of two or more.
- green pigment examples include C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58, 59, 62, 63, etc. is mentioned.
- blue pigment examples include C.I. I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.
- yellow pigment examples include those similar to those exemplified in the red pixel colorant.
- Pigment Green 36 (colorant (A- 5)), Pigment Green 62 (colorant (A-6)), Pigment Green 63 (colorant (A-11)), Pigment Green 59 (colorant (A-12)), Pigment Blue 15:3 (colorant Agent (A-7)) is preferred.
- colorant (A) for green pixels As a combination of colorants (A) for green pixels, the following combinations (I) to (IV) are more preferable.
- Colorant (A-4), Colorant (A-5) and Colorant (A-7) (II) Colorant (A-4) and Colorant (A-6)
- III) Colorant (A-4) and Colorant (A-11) (IV) Colorant (A-4) and Colorant (A-12)
- the content of the coloring agent (A-4) is 49% to 59% by weight, the coloring agent (A-5), the coloring agent (A-6), the coloring agent (A-11) or the coloring agent (A-12)
- the content of 33% to 51% by weight, the content of the colorant (A-7) is preferably 0% to 13% by weight, and the content of the colorant (A-7) is 3% by weight. ⁇ 13% by weight is more preferred.
- the present organic EL display device uses a combination of Pigment Blue 15:6 (also referred to as coloring agent (A-8)) and other coloring agents as a coloring agent for blue pixels.
- Pigment Blue 15:6 also referred to as coloring agent (A-8)
- other coloring agents as a coloring agent for blue pixels.
- a blue pigment, a purple pigment, or a xanthene-based dye is preferable as the other coloring agent in the coloring agent for blue pixels.
- Other colorants may be used singly or in combination of two or more.
- the purple pigment examples include C.I. I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
- blue pigment are the same as those exemplified in the above green pixel colorant.
- the xanthene dyes may be in the form of oil-soluble dyes, acid dyes, direct dyes, or basic dyes, and may also be used as lake pigments.
- the xanthene-based basic dye is preferably used after being salted using an organic acid or perchloric acid.
- the organic acid it is preferable to use an organic sulfonic acid or an organic carboxylic acid.
- naphthalenesulfonic acid such as Bias acid and perchloric acid are preferably used from the standpoint of resistance.
- the xanthene-based acid dye is salt-formed using a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, or a resin component having these functional groups, and used as a salt-forming compound. Alternatively, it can be sulfonamidated and used as a sulfonic acid amide compound.
- a salt-forming compound of a xanthene-based acid dye and a sulfonic acid amide compound of a xanthene-based acid dye are preferable because they are excellent in hue and resistance. It is more preferable to use a sulfonic acid amide compound obtained by sulfonamidating a xanthene acid dye.
- rhodamine-based dyes are preferable because they are excellent in color development and durability.
- xanthene oil-soluble dyes include C.I. I. Solvent Red 35, C.I. I. Solvent Red 36, C.I. I. Solvent Red 42, C.I. I. Solvent Red 43, C.I. I. Solvent Red 44, C.I. I. Solvent Red 45, C.I. I. Solvent Red 46, C.I. I. Solvent Red 47, C.I. I. Solvent Red 48, C.I. I. Solvent Red 49, C.I. I. Solvent Red 72, C.I. I. Solven Red 73, C.I. I. Solvent Red 109, C.I. I. Solvent Red 140, C.I. I. Solvent Red 141, C.I. I.
- Solvent Red 237 C.I. I. Solvent Red 246, C.I. I. solvent violet 2, C.I. I. solvent violet 10 and the like. Among them, C.I. I. Solvent Red 35, C.I. I. Solvent Red 36, C.I. I. Solvent Red 49, C.I. I. Solvent Red 109, C.I. I. Solvent Red 237, C.I. I. Solvent Red 246, C.I. I. Solvent Violet 2 is more preferred.
- xanthene-based basic dyes include C.I. I. Basic Red 1 (Rhodamine 6GCP), 8 (Rhodamine G), C.I. I. Basic Violet 10 (Rhodamine B) and the like. Among them, C.I. I. Basic Red 1, C.I. I. Basic Violet 10 is preferred.
- xanthene acid dyes include C.I. I. Acid Red 51 (erythrosine (food red No. 3)), C.I. I. Acid Red 52 (acid rhodamine), C.I. I. Acid Red 87 (Eosin G (Edible Red No. 103)), C.I. I. Acid Red 92 (Acid Phloxine PB (Edible Red No. 104)), C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B (Edible Red No. 5), Acid Rhodamine G, C.I. I. acid violet 9; Among them, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I.
- Acid Red 388 C.I. I. Acid Red 52 (acid rhodamine), C.I. I. Acid Red 289, Acid Rhodamine G, C.I. I. Acid Violet 9 is more preferred, and C.I. I. Acid Red 52, C.I. I. Preferably Acid Red 289 is used.
- the xanthene-based acid dye may be a salt-forming compound with a nitrogen-containing compound, and a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, etc., or a resin component having these functional groups is used. It is preferable to make a salt-forming compound of an acid dye by salt-forming, because high heat resistance, light resistance, and solvent resistance can be imparted. Acid dyes can be imparted with high heat resistance, light resistance and solvent resistance by sulfonamidation. Moreover, it may be a salt-forming compound of an acid dye and a compound having an onium base. An excellent coloring composition can be obtained.
- Primary amine compounds include methylamine, ethylamine, propylamine, isopropylamine, butylamine, amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridodecylamine, tetra decylamine (myristylamine), pentadecylamine, cetylamine, stearylamine, oleylamine, cocoalkylamine, beef tallow alkylamine, hardened beef tallow alkylamine, aliphatic unsaturated primary amines such as allylamine, aniline, benzylamine, and the like. .
- Secondary amine compounds include aliphatic unsaturated secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine and diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine, dicocoalkyl Amine, di-cured beef tallow alkylamine, distearylamine and the like.
- Tertiary amine compounds include trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, and tribenzylamine.
- a xanthene-based acid dye it may be used as a salt-forming compound (a) consisting of the acid dye and a quaternary ammonium salt compound.
- the quaternary ammonium salt compound as the counter component of the acid dye is described below.
- the quaternary ammonium salt compound (a) functions as a counter for acid dyes by having an amino group.
- a preferred form of the quaternary ammonium salt compound, which is the counter component of the salt-forming compound, is colorless or white.
- colorless or white means a so-called transparent state, and is defined as a state in which the transmittance is 95% or more, preferably 98% or more in the entire wavelength region of 400 to 700 nm in the visible light region. It is. That is, it is preferable that it does not interfere with the color development of the dye component and does not cause color change.
- the molecular weight of the counter portion which is the cationic component of the quaternary ammonium salt compound, is preferably in the range of 190-900. If the molecular weight is less than 190, the light resistance and heat resistance may be lowered, and the solubility in solvents may be lowered. On the other hand, if the molecular weight exceeds 900, the proportion of the coloring component in the molecule will decrease, resulting in a decrease in color developability and brightness. More preferably, the molecular weight of the counter moiety is in the range of 240-850. Particularly preferred are counter moieties with molecular weights in the range of 350-800.
- the molecular weight was calculated based on the structural formula, and the atomic weight of C was 12, the atomic weight of H was 1, and the atomic weight of N was 14.
- a compound represented by the following general formula (5) is preferable as the quaternary ammonium salt compound.
- R 31 to R 34 each independently represent an alkyl group having 1 to 20 carbon atoms or a benzyl group, and at least two of R 31 to R 34 have 5 to 20.
- X 1- represents an inorganic or organic anion.
- R 31 to R 34 When at least two or more of R 31 to R 34 have 5 to 20 carbon atoms, good solubility in a solvent is obtained. If there are three or more alkyl groups having a carbon number of less than 5, the solubility in a solvent is deteriorated, and foreign matter is likely to occur in the coating film. In addition, if an alkyl group having more than 20 carbon atoms is present, the salt-forming compound (a) will be impaired in color development.
- X 1- may be an inorganic or organic anion, preferably a halogen, and preferably a chloride ion (anion).
- Quaternary ammonium salt compounds include tetramethylammonium chloride, tetraethylammonium chloride, monostearyltrimethylammonium chloride, distearyldimethylammonium chloride, tristearylmonomethylammonium chloride, cetyltrimethylammonium chloride, trioctylmethylammonium chloride, and dioctyldimethylammonium chloride.
- monolauryltrimethylammonium chloride monolauryltrimethylammonium chloride, dilauryldimethylammonium chloride, trilaurylmethylammonium chloride, triamylbenzylammonium chloride, trihexylbenzylammonium chloride, trioctylbenzylammonium chloride, trilaurylbenzylammonium chloride, benzyldimethylstearylammonium chloride, and Examples include benzyldimethyloctylammonium chloride, dialkyl (alkyl is C14 to C18) dimethylammonium chloride (cured beef tallow), and the like.
- Specific products of quaternary ammonium salt compounds include, for example, Kotamine 24P, Kotamine 86P Conc, Kotamine 60W, Kotamine 86W, Kotamine D86P, Sansol C, Sansol B-50 manufactured by Kao Corporation, and Arcade 210- manufactured by Lion Corporation. 80E, 2C-75, 2HT-75, 2HT flakes, 2O-75I, 2HP-75, 2HP flakes, among others, Cortamine D86P (distearyldimethylammonium chloride), Arcade 2HT-75 (dialkyl (alkyl is C14- C18) dimethylammonium chloride).
- a xanthene-based acid dye it may be used as a salt-forming compound (a') comprising an acid dye and a resin having a cationic group in its side chain.
- a resin having a cationic group in a side chain for obtaining the salt-forming compound (a') will be described.
- the resin having a cationic group in the side chain for obtaining the salt-forming compound is not particularly limited as long as it has at least one onium base in the side chain.
- ammonium salts iodonium salts, sulfonium salts, diazonium salts, and phosphonium salts are preferable, and considering storage stability (thermal stability), ammonium salts, iodonium salts, and sulfonium salts are preferred. is more preferable. Ammonium salts are more preferred.
- the same resin As the binder resin constituting the photosensitive coloring composition.
- the resin having a cationic group in the side chain for obtaining the salt-forming compound (a') is preferably an acrylic resin.
- an alkali resin containing a structural unit represented by the following general formula (6) is preferable.
- a salt-forming compound can be obtained by forming a salt between the cationic group in the general formula (6) and the anionic group of the xanthene-based acid dye.
- R 41 represents a hydrogen atom or a substituted or unsubstituted alkyl group
- R 42 to R 44 each independently represent a hydrogen atom, an optionally substituted alkyl group, a substituted represents an optionally substituted alkenyl group or an optionally substituted aryl group, two of R 42 to R 44 may be bonded together to form a ring
- Q is an alkylene group, an arylene group, or —CONH —R 45 —, —COO—R 45 —
- R 45 represents an alkylene group
- X 2- represents an inorganic or organic anion.
- Examples of the alkyl group for R 41 include methyl group, ethyl group, propyl group, n-butyl group, i-butyl group, t-butyl group, n-hexyl group and cyclohexyl group.
- an alkyl group having 1 to 12 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
- examples of the substituent include a hydroxyl group and an alkoxyl group.
- R 41 is most preferably a hydrogen atom or a methyl group.
- alkyl groups for R 42 to R 44 include linear alkyl groups (methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl and n-octadecyl, etc.), branched alkyl groups (isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl, 2-ethylhexyl and 1,1,3,3-tetramethyl butyl, etc.), cycloalkyl groups (such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl) and bridged cyclic alkyl groups (such as nor
- alkenyl groups for R 42 to R 44 include linear or branched alkenyl groups (vinyl, allyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl and 2-methyl-2-propenyl etc.), cycloalkenyl groups (2-cyclohexenyl and 3-cyclohexenyl etc.).
- the alkenyl group is preferably an alkenyl group having 2 to 18 carbon atoms, more preferably an alkenyl group having 2 to 8 carbon atoms.
- aryl groups for R 42 to R 44 include monocyclic aryl groups (phenyl etc.), condensed polycyclic aryl groups (naphthyl, anthracenyl, phenanthrenyl, anthraquinolyl, fluorenyl, naphthoquinolyl etc.) and aromatic heterocyclic hydrocarbons.
- alkyl group, alkenyl group or aryl group represented by R 42 to R 44 has a substituent
- substituents include a halogen atom, a hydroxyl group, an alkoxyl group, an aryloxy group, an alkenyl group, an acyl group, A substituent selected from an alkoxycarbonyl group, a carboxyl group, a phenyl group, and the like can be mentioned.
- substituents halogen atoms, hydroxyl groups, alkoxyl groups, and phenyl groups are particularly preferred.
- R 42 to R 44 are preferably optionally substituted alkyl groups, more preferably unsubstituted alkyl groups.
- two of R 42 to R 44 may combine with each other to form a ring.
- the component of Q connecting the vinyl moiety and the ammonium base represents an alkylene group, an arylene group, -CONH-R 45 -, and -COO-R 45 -, and R 45 represents an alkylene group, Among them, -CONH-R 45 - and -COO-R 45 - are preferred from the viewpoint of polymerizability and availability. Further, R45 is more preferably a methylene group, an ethylene group, a propylene group or a butylene group, and particularly preferably an ethylene group.
- the component X 2- in general formula (6), which constitutes the counter anion of the resin, may be an inorganic or organic anion.
- the counter anion known ones can be employed without limitation, and specific examples include hydroxide ions; halide ions such as chloride ions, bromide ions and iodide ions; carboxylate ions such as formate ions and acetate ions; such as carbonate, bicarbonate, nitrate, sulfate, sulfite, chromate, dichromate, phosphate, cyanide, permanganate and also hexacyanoferrate(III) complex ions and the like.
- Halogen ions and carboxylate ions are preferred, and halogen ions are most preferred, from the viewpoints of suitability for synthesis and stability.
- the counter anion is an organic acid ion such as carboxylate ion
- the organic acid ion may be covalently bonded to the resin to form an inner salt.
- One method of introducing an oxetane group into a resin having a cationic group in its side chain is to convert an ethylenically unsaturated monomer containing an oxetane structure to a cationic group represented by general formula (6). It is a method of copolymerizing with an ethylenically unsaturated monomer.
- Ethylenically unsaturated monomers having an oxetane group include (3-methyl-3-oxetanyl)methyl (meth)acrylate, (3-ethyl-3-oxetanyl)methyl (meth)acrylate, (3-butyl-3 -oxetanyl)methyl (meth)acrylate, (3-hexyltyl-3-oxetanyl)methyl (meth)acrylate and the like.
- Examples of commercially available products include ETERNA COLL OXMA (manufactured by Ube Industries), OXE-10, and OXE-30 (manufactured by Osaka Organic Chemical Industry Co., Ltd.).
- a salt-forming compound of an acid dye and a nitrogen-containing compound or a resin having a cationic group in a side chain can be produced by a conventionally known method.
- a specific method is disclosed in Japanese Patent Application Laid-Open No. 11-72969.
- a quaternary ammonium salt compound may be added, and the solution may be subjected to chlorination while stirring.
- the sulfonic acid group (--SO 3 H) and sodium sulfonate group (--SO 3 Na) in the xanthene-based acid dye are combined with the ammonium group (NH4 + ) in the quaternary ammonium salt compound to form a salt.
- a compound is obtained.
- methanol and ethanol are also usable solvents for chlorination.
- the salt-forming compound is obtained by stirring or vibrating an aqueous solution in which a resin having a cationic group in the side chain represented by the general formula (6) and an acid dye is dissolved, or It can be easily obtained by mixing an aqueous solution of a resin having a cationic group in its side chain and an aqueous solution of an acid dye under stirring or shaking.
- an aqueous solution the ammonium group of the resin and the anionic group of the acid dye are ionized, and they form an ionic bond, and the ion-bonded portion becomes water-insoluble and precipitates.
- the salt composed of the counter anion of the resin and the counter cation of the acid dye is water-soluble, it can be removed by washing with water or the like.
- the resin having a cationic group in the side chain and the acid dye to be used may be of a single type or may be of a plurality of types having different structures. Also, with other acid dyes, a salt-forming compound with a nitrogen-containing compound or a resin having a cationic group in the side chain can be obtained in the same manner as for xanthene dyes.
- the acid dye may be a sulfonic acid amide compound obtained by reacting a sulfonic acid amide compound with an anionic dye.
- Sulfonic acid amide compounds of acid dyes that can be preferably used for acid dyes are obtained by chlorinating acid dyes having —SO 3 H and —SO 3 Na by a conventional method to convert —SO 3 H to —SO 2 Cl.
- Compounds can be prepared by reacting with an amine having a —NH 2 group.
- Amine compounds that can be preferably used in sulfonamidation include, specifically, 2-ethylhexylamine, dodecylamine, 3-decyloxypropylamine, 3-(2-ethylhexyloxy)propylamine, and 3-ethoxypropyl. Amines, cyclohexylamines and the like are preferably used.
- C.I. I As an example of xanthene-based acid dyes, C.I. I.
- a sulfonic acid amide compound obtained by modifying Acid Red 289 with 3-(2-ethylhexyloxy)propylamine C.I. I.
- Acid Red 289 is sulfonyl chlorided and then reacted with the theoretical equivalent of 3-(2-ethylhexyloxy)propylamine in dioxane to give C.I. I.
- a sulfonic acid amide compound of Acid Red 289 may be obtained.
- Acid Red 52 is sulfonyl chlorided and then reacted with the theoretical equivalent of 3-(2-ethylhexyloxy)propylamine in dioxane to give C.I. I.
- a sulfonic acid amide compound of Acid Red 52 may be obtained.
- pigment violet 23 colorant (A -9)
- xanthene dyes colorant (A-10) are preferred.
- the content of the colorant (A-8) in the colorant (A) is 58% to 64% by weight.
- the content of the coloring agent (A-9) is preferably 12% to 20% by weight, and the content of the coloring agent (A-10) is preferably 17% to 25% by weight.
- the method for refining the pigment can be appropriately selected from known methods, and examples thereof include wet grinding, dry grinding, dissolution precipitation method, etc. Salt milling treatment by a kneader method, which is one type of wet grinding, is performed. be able to.
- the salt milling process involves milling a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent while heating using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, and sand mill.
- a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, and sand mill.
- This is a treatment in which water-soluble inorganic salts and water-soluble organic solvents are removed by washing with water after kneading to a certain extent.
- the water-soluble inorganic salt functions as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling.
- water-soluble inorganic salt sodium chloride, barium chloride, potassium chloride, sodium sulfate, etc. can be used, but it is preferable to use sodium chloride (salt) from the viewpoint of price.
- the water-soluble inorganic salt is preferably used in an amount of 50 to 2,000 parts by mass, most preferably 300 to 1,000 parts by mass, based on 100 parts by mass of the pigment, from the viewpoint of both processing efficiency and production efficiency.
- the water-soluble organic solvent has the function of moistening the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used.
- a high boiling point solvent having a boiling point of 120° C. or higher is preferable from the viewpoint of safety.
- the water-soluble organic solvent is preferably used in an amount of 5 to 1,000 parts by mass, most preferably 50 to 500 parts by mass, per 100 parts by mass of the pigment.
- a resin may be added as necessary when salt milling the pigment.
- the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used.
- the resins used are preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the above organic solvents.
- the amount of the resin used is preferably in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the pigment.
- the primary particle size of the pigment is preferably 20 nm or more because it is well dispersed in the carrier. Moreover, since a color filter having a high contrast ratio can be formed, the thickness is preferably 100 nm or less. A particularly preferred range is from 25 to 85 nm.
- the primary particle size of the pigment is determined by a method of directly measuring the size of the primary particles from an electron micrograph of the pigment taken by a TEM (transmission electron microscope). Specifically, the minor axis diameter and the major axis diameter of the primary particles of each pigment are measured, and the average is taken as the particle diameter of the pigment particles. Next, for 100 or more pigment particles, the volume of each particle is obtained by approximating it to the cube of the obtained particle size, and the volume average particle size is taken as the average primary particle size.
- the photopolymerizable monomer (B) contains at least a compound represented by the following general formula (1), and may further contain other photopolymerizable monomers as necessary.
- the compound represented by formula (1) include trimethylolpropane triacrylate, trimethylolpropane EO-modified triacrylate, trimethylolpropane PO-modified triacrylate, pentaerythritol triacrylate, and pentaerythritol tetraacrylate. be done.
- the compounds represented by formula (1) can be used singly or in combination of two or more.
- photopolymerizable monomers include known (meth)acrylate monomers. Specifically, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, ⁇ -carboxyethyl (meth) Acrylates, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol Tetra (meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl
- the content of the photopolymerizable monomer (B) with respect to the total solid content in the photosensitive coloring composition is preferably 5-40% by mass.
- the content of the compound represented by the general formula (1) contained in the photopolymerizable monomer (B) is 50 to 100% by mass with respect to the total amount of the photopolymerizable monomer (B). and more preferably 60% by mass or more.
- the photopolymerization initiator (C) contains an oxime ester-based photopolymerization initiator, and may further contain other photopolymerization initiators as necessary.
- the photosensitive coloring composition containing the oxime ester-based photopolymerization initiator can be a photosensitive coloring composition having ultraviolet irradiation curability and solvent developability or alkali developability. Therefore, according to the said photosensitive coloring composition, a pixel can be formed by the photolithographic method.
- a photosensitive coloring composition having excellent color characteristics and chemical resistance and good patterning properties can be obtained.
- the N—O bond of the oxime is cleaved to generate iminyl radicals and alkyloxy radicals. Since these radicals are further decomposed to generate highly active radicals, a pattern can be formed with a small amount of exposure.
- the coloring agent concentration of the photosensitive coloring composition is high, the UV transmittance of the coating film may be low, and the curing degree of the coating film may be low. Since the present photosensitive coloring composition contains an oxime ester photopolymerization initiator with high quantum efficiency, it has excellent curability even when the concentration of the coloring agent is high.
- oxime ester photopolymerization initiator examples include, among others, oxime ester photopolymerization initiators represented by the following general formulas (2) to (4), and represented by the following general formula (2) or (3). is preferred, and an oxime ester photopolymerization initiator represented by the general formula (2) is more preferred.
- R 1 represents an optionally substituted alkyl group having 1 to 20 carbon atoms
- R 2 represents represents an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group
- each of R 3 to R 10 independently has a hydrogen atom and a substituent; represents an alkyl group having 1 to 20 carbon atoms which may be represents a good aryl group.
- alkyl groups having 1 to 20 carbon atoms in R 1 to R 10 include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group and dodecyl group.
- Examples of the aryl group for R 2 to R 11 include phenyl group, naphthyl group, anthracenyl group and the like.
- the substituent that the alkyl group and the aryl group may have means that the alkyl group or the aryl group may have a substituent instead of a hydrogen atom.
- the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; alkoxy groups such as a methoxy group, an ethoxy group and a tert-butoxy group; Group; Alkoxycarbonyl group such as methoxycarbonyl group, butoxycarbonyl group, phenoxycarbonyl group; Acyloxy group such as acetoxy group, propionyloxy group, benzoyloxy group; Acyl group, benzoyl group, isobutyryl group, acryloyl group, methacryloyl group, methoxalyl acyl groups such as groups; alkylsulfanyl groups such as methylsulfanyl group and tert-butyl
- R 1 is carbon which may have a substituent an alkyl group having a number of 1 to 20,
- R 2 being an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group
- R 3 to R 10 each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group, a nitro group, or an R -CO- group is preferred.
- R 4 to R 6 and R 8 to R 10 are hydrogen atoms
- R 7 is a hydrogen atom or R 11 —CO— group
- R 11 is an aryl group which may have a substituent. is more preferable.
- oxime ester-based photopolymerization initiators represented by general formula (2) compounds represented by the following chemical formulas (2-1) and (2-2) are preferred.
- W 1 and W 2 each independently represent a carbonyl bond (--CO--) or a single bond, and at least one of W 1 and W 2 is a carbonyl bond (--CO--).
- R a is an alkyl group having 2 to 6 carbon atoms
- R b is an alkyl group having 4 to 10 carbon atoms
- R c contains at least a hydrocarbon ring or heterocyclic ring and further has 1 to 4 carbon atoms.
- R d and R e are each independently an alkyl group having 1 to 6 carbon atoms.
- alkyl groups for R a include linear alkyl groups such as ethyl, propyl, butyl and hexyl groups.
- the alkyl group for Rb includes linear alkyl groups such as butyl, hexyl, octyl and dodecyl groups.
- the hydrocarbon ring for Rc includes aliphatic hydrocarbon rings such as cyclohexyl groups, and aromatic hydrocarbon rings such as phenyl groups, naphthyl groups and anthracenyl groups.
- examples of the heterocyclic ring for R c include rings in which one or more carbon atoms of the above hydrocarbon ring are replaced with a nitrogen atom, an oxygen atom, or a sulfur atom.
- alkyl groups for R d and R e include linear alkyl groups such as methyl, ethyl, propyl, butyl and hexyl groups.
- oxime ester-based photopolymerization initiator represented by general formula (3) a compound represented by the following chemical formula (3-1) is preferred.
- R 21 and R 22 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl and R 23 and R 24 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group, R 25 is a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group, or an R 26 —CO— group, and R 26 is a substituted an alkyl group having 1 to 20 carbon atoms which may have a group, an aryl group which may have a substituent, or a heterocyclic group.
- the alkyl group having 1 to 20 carbon atoms for R 21 to R 26 can be the same as the alkyl group having 1 to 20 carbon atoms for R 1 to R 10 .
- the aryl groups for R 21 to R 26 can be the same as the aryl groups for R 2 to R 11 above.
- heterocyclic ring in the heterocyclic group represented by R 26 examples include furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyran, pyrone, pyridine, pyrone, pyridazine, pyrimidine, pyrazine, benzofuran, thionaphthene, indole, carbazole, coumarin, quinoline, phthalazine, quinoxaline and the like.
- the substituents that the alkyl group and the aryl group may have may be the same as the substituents in the general formula (2).
- R 21 is an optionally substituted aryl group
- R 22 is a C 1 to 20 optionally substituted aryl group. It is preferably an alkyl group
- R 23 and R 24 are hydrogen atoms
- R 25 is a hydrogen atom, or an R 26 —CO— group.
- oxime ester photopolymerization initiator represented by general formula (4) a compound represented by the following chemical formula (4-1) is preferable.
- the photopolymerization initiator (C) may further contain other photopolymerization initiators.
- Other photopolymerization initiators include, for example, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1 -one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl ) Methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and other acetophenone compounds Benzoin compounds such as benzoin, benzoin, benzoin, benzoin, be
- photopolymerization initiators can be used singly or as a mixture of two or more at any ratio as required.
- all acetophenone compounds are manufactured by BASF Japan Co., Ltd.
- "IRGACURE 907" (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1 -on)
- "IRGACURE 369” (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone
- IRGACURE 379 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one and phosphine-based compounds are all manufactured by BASF Japan Ltd.
- IRGACURE 819 bis(2,4,6- trimethylbenzoyl)phenylphosphine oxide
- IRGACURE TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide) and the like.
- the content of the photopolymerization initiator (C) is preferably 0.5 to 50 parts by mass with respect to 100 parts by mass of the colorant (A), and from the viewpoint of photocurability and developability, 1 to 30 parts by mass. is more preferable.
- the photopolymerization initiator (C) is 1 part by mass or more, the adhesiveness to the substrate is excellent.
- the photopolymerization initiator (C) is 30 parts by mass or less, the resolution is excellent.
- the photosensitive coloring composition may further contain a sensitizer.
- Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone; 1,2-diketone derivatives such as benzyl and camphorquinone; benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene.
- polymethine dyes such as derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives; acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, phthalocyanine derivatives, pyrylium derivatives, thio
- sensitizers that are particularly suitable for sensitization. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4′-bis (Dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl- Examples include N-ethylcarbazole and the like.
- sensitizers include "KAYACURE DETX-S” (2,3-diethylthioxanthone manufactured by Nippon Kayaku Co., Ltd.), "EAB-F”(4,4'-bis(diethylamino)benzophenone, Hodogaya Chemical Industry company) and the like.
- a sensitizer that absorbs light in the ultraviolet to near-infrared region can also be contained.
- the sensitizers can be used singly or as a mixture of two or more at any ratio as required.
- the content when using a sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (C) contained in the coloring composition, and photocurability and developability. From the point of view, it is more preferably 5 to 50 parts by mass.
- This photosensitive coloring composition contains a resin (D).
- the resin (D) is preferably a transparent resin having a transmittance of 80% or more in the entire wavelength range of 400 to 700 nm when a 2 ⁇ m-thick coating is formed, and the transmittance is preferably 95% or more.
- the resin (D) is preferably one or more selected from thermoplastic resins and photosensitive resins. Moreover, it is preferable that the resin (D) has alkali solubility. Thereby, the film formed from the photosensitive coloring composition can be patterned by photolithography.
- the photosensitive resin that does not have alkali solubility and the alkali-soluble resin may have a thermosetting group. Examples of the thermosetting group include an epoxy group and an oxetanyl group.
- the resin (D) can be used alone or in combination of two or more.
- the content of resin (D) is preferably 20 to 400 parts by mass, more preferably 50 to 250 parts by mass, based on 100 parts by mass of colorant (A). When contained in an appropriate amount, a film can be easily formed, and good color characteristics can be easily obtained.
- alkali-soluble resins include resins having acidic groups such as carboxyl groups and sulfone groups.
- Alkali-soluble thermoplastic resins include, for example, acrylic resins having acidic groups, ⁇ -olefin/(anhydride) maleic acid copolymers, styrene/styrenesulfonic acid copolymers, and ethylene/(meth)acrylic acid copolymers. , or isobutylene/(anhydride) maleic acid copolymer.
- an acrylic resin having an acidic group and a styrene/styrenesulfonic acid copolymer are preferred from the standpoint of improving developability, heat resistance and transparency.
- thermoplastic resin may contain those not having alkali solubility.
- Non-alkali-soluble thermoplastic resins include, for example, acrylic resins, butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate , polyurethane resins, polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, and polyimide resins. .
- the alkali-soluble photosensitive resin has photosensitivity because it has a polymerizable unsaturated group.
- the alkali-soluble photosensitive resin is alkali-soluble and photosensitive, and a known resin can be used, and a resin synthesized by the following methods (i) and (ii) is preferable.
- the alkali-soluble photosensitive resin is used, it is three-dimensionally crosslinked by irradiation with light, increasing the crosslink density, thereby improving the chemical resistance of the film.
- Method (i) for example, first synthesizes a polymer of an epoxy group-containing monomer and other monomers. Next, there is a method of adding a monocarboxyl group-containing monomer to the epoxy group of the polymer, and reacting the formed hydroxyl group with a polybasic acid anhydride to obtain an alkali-soluble photosensitive resin.
- the monocarboxyl group-containing monomer is a monomer having one carboxyl group.
- Epoxy group-containing monomers include, for example, glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4- Epoxycyclohexyl (meth)acrylates can be mentioned.
- glycidyl (meth)acrylate is preferable from the viewpoint of reactivity.
- Monocarboxyl group-containing monomers are, for example, (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, ⁇ -position haloalkyl of (meth)acrylic acid, alkoxyl, halogen, nitro, cyano-substituted and monocarboxylic acids such as monocarboxylic acids.
- polybasic acid anhydrides examples include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride.
- the polybasic acid anhydride may have a carboxyl group that does not form an acid anhydride.
- Other monomers include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t- Butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isobornyl (meth)acrylate, phenyl (meth)acrylate (meth)acrylates such as acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)
- a hydroxyl group-containing monomer, a carboxyl group-containing monomer, and other monomers are synthesized to produce a polymer.
- a method of synthesizing an alkali-soluble photosensitive resin by reacting the hydroxyl group of the polymer with the isocyanate group of an isocyanate group-containing monomer.
- Hydroxyl group-containing monomers for example, 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol mono (meth)
- Examples include acrylates or hydroxyalkyl methacrylates such as cyclohexanedimethanol mono(meth)acrylate.
- polyether mono(meth)acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide to hydroxyalkyl (meth)acrylate, poly ⁇ -valerolactone, poly ⁇ -caprolactone, and/or poly Polyester mono(meth)acrylates to which 12-hydroxystearic acid or the like is added are also included.
- 2-hydroxyethyl methacrylate and glycerol mono(meth)acrylate are preferred, and glycerol mono(meth)acrylate is more preferred.
- isocyanate group-containing monomers examples include 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, and 1,1-bis[methacryloyloxy]ethyl isocyanate.
- monomers that can be used other than the above monomers include phosphate ester group-containing monomers.
- a phosphate ester group-containing monomer is, for example, a compound obtained by reacting a hydroxyl group of a hydroxyl group-containing monomer with a phosphorylating agent such as phosphorus pentoxide or polyphosphoric acid.
- the raw materials for the resin (D) can be used singly or in combination of two or more. Moreover, resin (D) can be used individually or in combination of 2 or more types.
- the content of the resin (D) is preferably 20 to 400 parts by mass, more preferably 50 to 250 parts by mass, based on 100 parts by mass of the colorant (A). 20 parts by mass or more is preferable because the film formability and various resistances are good, and 400 parts by mass or less is preferable because the concentration of the coloring agent is high and good color characteristics can be exhibited.
- the weight average molecular weight (Mw) of the resin (D) is preferably 2,000 to 40,000, more preferably 3,000 to 30,000, even more preferably 4,000 to 20,000.
- the value of Mw/Mn is preferably 10 or less.
- Mn is a number average molecular weight.
- the acid value of the resin (D) is preferably 50-200 mgKOH/g, more preferably 70-180 mgKOH/g, even more preferably 90-170 mgKOH/g. Adequate acid value enables highly balanced alkali solubility, adhesion, and residue suppression.
- the photosensitive coloring composition contains a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), and optionally other components.
- A coloring agent
- B photopolymerizable monomer
- C photopolymerization initiator
- D resin
- the photosensitive coloring composition may contain a thermosetting compound.
- a thermosetting compound As a result, when a color filter is produced, the heat resistance is improved because the crosslinking density is improved in the heating step after the film is patterned by photolithography. In addition, since the colorant (A) is less likely to aggregate in the heating step, the contrast ratio is further improved.
- thermosetting compound is a low-molecular-weight compound or polymer (thermosetting resin) and is not limited by molecular weight.
- the thermosetting resin is included in the thermosetting compound.
- Thermosetting compounds include, for example, epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenolic compounds. Among these, epoxy compounds and oxetane compounds are preferred.
- Epoxy compounds include, for example, bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted polycondensates of various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.), phenol polymers with various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene
- epoxy compounds include, for example, Epicoat 807, Epicote 815, Epicote 825, Epicote 827, Epicote 828, Epicote 190P, Epicote 191P (manufactured by Yuka Shell Epoxy Co., Ltd.), Epicote 1004, and Epicote 1256 (manufactured by Yuka Shell Epoxy Co., Ltd.).
- the content of the epoxy compound is preferably 0.5 to 300 parts by mass, more preferably 1.0 to 50 parts by mass, based on 100 parts by mass of the colorant (A).
- the heat resistance and pattern shape of the film are further improved.
- An oxetane compound is a compound having an oxetane group.
- examples of the oxetane compound include monofunctional oxetane compounds, bifunctional oxetane compounds, and trifunctional or higher oxetane compounds.
- Monofunctional oxetane compounds include, for example, (3-ethyloxetan-3-yl)methyl acrylate, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-ethyl-3-(2-methacryloxymethyl)oxetane, 3-ethyl-3- ⁇ [3-(triethoxy silyl)propoxy]methyl ⁇ oxetane and the like.
- Commercially available products include OXE-10 and OXE-30 manufactured by Osaka Organic Chemical Industry Co., Ltd., OXT-101 and OXT-212 manufactured by Toagosei Co., Ltd., and the like.
- Bifunctional oxetane compounds include, for example, 4,4′-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl), 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 1,4-bis ⁇ [(3-ethyl-3-oxetanyl)methoxy]methyl ⁇ benzene, di[1-ethyl(3-oxetanyl)]methyl ether, di[1-ethyl(3-oxetanyl)]methyl ether- 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(2-phenoxymethyl)oxetane, 3,7-bis(3-oxetanyl) -5-oxa-nonane, 1,2-bis[(3-e
- trifunctional or higher oxetane groups include pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, and dipentaerythritol hexa(3-ethyl).
- the content of the oxetane compound is preferably 0.5 to 50 parts by mass, more preferably 1 to 40 parts by mass. If it is contained in an appropriate amount, the solvent resistance of the film will be further improved.
- a melamine compound is a compound having a melamine ring structure.
- Melamine compounds include low-molecular-weight compounds and high-molecular-weight compounds.
- the melamine compound used herein is preferably a compound in which a methylol group or an ether group is bonded to a melamine ring.
- the average number of bonds of methylol groups and/or ether groups per melamine ring is preferably 5.0 or more. If it has an appropriate number of bonds, the solvent resistance of the film is further improved, and the contrast ratio is less likely to decrease.
- melamine compounds include, for example, Nicarac MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X , MS-001, MX-002, MX-730, MX-750, MX-708, MX-706, MX-042, MX-45, MX-500, MX-520, MX-43, MX-417, MX -410 (manufactured by Sanwa Chemical Co., Ltd.), Cymel 232, 235, 236, 238, 285, 300, 301, 303, 350, 370 (manufactured by Nippon Cytec Industries Co., Ltd.) and the like.
- dicarac MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, and MW-30 having an average number of methylol groups and/or ether groups per melamine ring of 5.0 or more , MW-22, MS-21, MS-11, MW-24X, MX-45 (manufactured by Sanwa Chemical Co., Ltd.) Cymel 232, 235, 236, 238, 300, 301, 303, 350 (manufactured by Nippon Cytec Industries Co., Ltd.) is preferable in terms of further improving the crosslink density of the coating.
- the total content of the thermosetting compound is preferably 20-400 parts by mass, more preferably 50-250 parts by mass, based on 100 parts by mass of the colorant (A). 20 parts by mass or more is preferable because the film formability and various resistances are good, and 400 parts by mass or less is preferable because the concentration of the coloring agent is high and good color characteristics can be exhibited.
- the present photosensitive coloring composition may contain an antioxidant.
- the antioxidant prevents the photopolymerization initiator and the thermosetting compound from being oxidized and yellowing due to the heat process during thermosetting and ITO annealing, so that the transmittance of the pixel can be increased.
- the "antioxidant” may be a compound having an ultraviolet absorption function, a radical scavenging function, or a peroxide decomposition function. , sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylic acid ester-based, and triazine-based compounds, and known ultraviolet absorbers, antioxidants, and the like can be used.
- hindered phenol-based antioxidants hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferred from the viewpoint of achieving both transmittance and sensitivity of the coating film.
- Dophenol-based antioxidants, hindered amine-based antioxidants, or phosphorus-based antioxidants are more preferred.
- Hindered phenol antioxidants include 2,4-bis[(laurylthio)methyl]-o-cresol, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl), 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di -t-butylanilino)-1,3,5-triazine, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,6-di-t-butyl-4- nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 4,4'-butylidene-bis-(2-t-butyl-5-methylphenol), 2,2'-thio- Bis-(6-t-buty
- Hindered amine antioxidants include bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(N-methyl-2,2,6,6-tetramethyl-4-piperidyl) sebacate, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4 -piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)(1,2,3, 4-butanetetracarboxylate, poly[ ⁇ 6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl ⁇ (2,2,6,6 -tetramethyl-4-piperidyl)imino ⁇ hexamethyl ⁇ (2,2,6,6-tetra
- Phosphorus antioxidants include tris(isodecyl)phosphite, tris(tridecyl)phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi(tridecyl)phosphite, diphenylisooctylphosphite, diphenylisodecyl phosphite, diphenyltridecylphosphite, triphenylphosphite, tris(nonylphenyl)phosphite, 4,4' isopropylidenediphenol alkylphosphite, trisnonylphenylphosphite, trisdinonylphenylphosphite, tris(2 ,4-di-t-butylphenyl)phosphite, tris(biphenyl)phosphi
- Sulfur antioxidants include 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]- o-cresol, 2,4-bis[(laurylthio)methyl]-o-cresol and the like.
- oligomer type and polymer type compounds having a thioether structure may also be used.
- Benzotriazole-based antioxidants include oligomer-type and polymer-type compounds having a benzotriazole structure.
- Benzophenone antioxidants such as 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4- Octadecyloxybenzophenone, 2,2'dihydroxy-4-methoxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4- methoxy-5-sulfobenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-chlorobenzophenone and the like.
- oligomer type and polymer type compounds having a benzophenone structure may also be used.
- triazine antioxidants examples include 2,4-bis(allyl)-6-(2-hydroxyphenyl)1,3,5-triazine.
- oligomer type and polymer type compounds having a triazine structure may also be used.
- salicylic acid ester-based antioxidants examples include phenyl salicylate, p-octylphenyl salicylate, and p-tertbutylphenyl salicylate.
- oligomer type and polymer type compounds having a salicylic acid ester structure may also be used.
- antioxidants can be used singly or as a mixture of two or more at any ratio as needed.
- the content of the antioxidant is preferably 0.5 to 5.0% by mass based on the total solid content of the photosensitive coloring composition from the viewpoint of brightness and sensitivity.
- the photosensitive coloring composition may contain an adhesion improver such as a silane coupling agent in order to improve adhesion to the substrate.
- an adhesion improver such as a silane coupling agent in order to improve adhesion to the substrate.
- adhesion improvers include vinylsilanes such as vinyltrimethoxysilane and vinyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3- (Meth)acrylsilanes such as methacryloxypropyltriethoxysilane and 3-acryloxypropyltrimethoxysilane 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3- Epoxysilanes such as glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane , N-
- the adhesion improver can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, per 100 parts by weight of the colorant in the coloring composition. Within this range, the effect is enhanced and the balance between adhesion, resolution, and sensitivity is good, which is more preferable.
- a leveling agent may be added to the photosensitive coloring composition in order to improve the leveling property of the composition.
- the leveling agent dimethylsiloxane having a polyether structure or a polyester structure in its main chain is preferred. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Dow Corning Toray Co., Ltd. and BYK-333 manufactured by BYK Chemie. Specific examples of dimethylsiloxane having a polyester structure include BYK-310 and BYK-370 manufactured by BYK-Chemie. A dimethylsiloxane having a polyether structure in its main chain and a dimethylsiloxane having a polyester structure in its main chain can be used in combination.
- the content of the leveling agent is preferably 0.003 to 0.5% by mass based on the total solid content of the coloring composition.
- a leveling agent is a type of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a hydrophilic group but has low solubility in water, and when added to the coloring composition, its It is useful that it has the characteristic of low surface tension lowering ability and good wettability to the glass plate despite the low surface tension lowering ability, and it is added in an amount that does not cause defects in the coating film due to bubbling.
- a substance capable of sufficiently suppressing chargeability can be preferably used.
- a dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used as a leveling agent having such preferred properties.
- Polyalkylene oxide units include polyethylene oxide units and polypropylene oxide units, and dimethylpolysiloxane may have both polyethylene oxide units and polypropylene oxide units.
- Anionic, cationic, nonionic or amphoteric surfactants can be added to the leveling agent as auxiliaries. Two or more kinds of surfactants may be mixed and used. Examples of anionic surfactants added to the leveling agent include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, and alkyldiphenyl ether disulfonic acid.
- cationic surfactants that are added to leveling agents include alkyl quaternary ammonium salts and their ethylene oxide adducts.
- Nonionic surfactants added to the leveling agent include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate. , polyethylene glycol monolaurate; alkylbetaines such as alkyldimethylaminoacetic acid betaine; amphoteric surfactants such as alkylimidazoline; and fluorine-based and silicone-based surfactants.
- the photosensitive coloring composition may contain a curing agent and a curing accelerator as necessary in order to assist curing of the thermosetting resin.
- a curing agent Phenol-based resins, amine-based compounds, acid anhydrides, active esters, carboxylic acid-based compounds, sulfonic acid-based compounds and the like are effective as curing agents, but are not particularly limited to these. Any curing agent can be used as long as it can react with the . Among these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferred.
- the curing accelerator examples include amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl -N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivatives bicyclic amidine compounds and salts thereof (e.g., imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2- ethyl-4-methylimid
- the present photosensitive coloring composition may contain a storage stabilizer in order to stabilize the viscosity over time.
- Storage stabilizers include, for example, benzyltrimethyl chloride, quaternary ammonium chloride such as diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, tetraphenylphosphine and the like. organic phosphines, phosphites, and the like.
- the storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the colorant.
- the photosensitive coloring composition may contain a solvent. This facilitates the adjustment of the viscosity of the photosensitive coloring composition, making it easier to form a film with a smooth surface.
- the solvent may be appropriately selected according to the purpose of use and contained in an appropriate amount.
- Solvents include, for example, ester solvents (solvents containing -COO- in the molecule but not containing -O-), ether solvents (solvents containing -O- in the molecule but not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (containing OH in the molecule, -O -, -CO- and -COO--free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.
- ester solvent examples include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, Butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, ⁇ -butyrolactone and the like.
- Ether solvents include ether solvents having no hydroxyl group and ether alcohol solvents (solvents containing —OH and —O— in the molecule).
- Ether alcohol solvents include, for example, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monobutyl ether.
- propylene glycol monomethyl ether propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methyl Butanol etc. are mentioned.
- Ether solvents having no hydroxyl group include, for example, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, dipropylene glycol dimethyl ether, dipropylene. Glycol methyl-n-propyl ether, anisole, phenetole, methylanisole and the like.
- the present photosensitive coloring composition preferably contains an ether alcohol solvent from the viewpoint of compatibility and coatability of the photosensitive coloring composition.
- Ether ester solvents are, for example, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3- ethyl ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate , ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono
- Ketone solvents are, for example, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
- alcohol solvents examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, 1,3-butylene glycol, and glycerin.
- aromatic hydrocarbon solvents examples include benzene, toluene, xylene, and mesitylene.
- Amide solvents include, for example, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and the like.
- a solvent having a boiling point of 120°C or higher and 245°C or lower at 1 atm is preferable in terms of coating properties and drying properties.
- propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2- Pentanone, N,N-dimethylformamide, N-methylpyrrolidone, cyclohexanone, tripropylene glycol monomethyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono Butyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, dipropylene
- solvents can adjust the viscosity of the photosensitive coloring composition to an appropriate viscosity and can form a coating film with the desired uniform thickness, 200 parts per 100 parts by mass of the solid content of the photosensitive coloring composition It is preferably used in an amount of up to 900 parts by mass, more preferably in an amount of 300 to 570 parts by mass.
- the viscosity of the photosensitive coloring composition is preferably 2.4 to 7.2 mPa ⁇ s, more preferably 3.4 to 6.4 mPa ⁇ s.
- the photosensitive coloring composition of the present organic EL display device it is preferable to use both an ether alcohol solvent and an ether ester solvent as the solvent.
- an ether alcohol solvent and an ether ester solvent By using the solvent together, cracks on the surface of pixels formed from the photosensitive coloring composition are suppressed, and the smoothness is improved.
- the boiling point of these solvents is preferably 140° C. or higher and 245° C. or lower.
- ether alcohol solvents include tripropylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, 3-methoxy-1-butanol, 3-methoxy-3 -Methylbutanol is preferred.
- propylene glycol monomethyl ether acetate and ethyl 3-ethoxypropionate are preferable as the ether ester solvent.
- the ratio of the ether ester solvent is preferably 250 to 600 parts by weight, preferably 300 to 450 parts by weight, with respect to 100 parts by weight of the solid content of the photosensitive coloring composition. part is more preferred.
- the ratio of the ether alcohol solvent is preferably 2.5 to 100 parts by mass, more preferably 5 to 45 parts by mass, per 100 parts by mass of the solid content of the photosensitive coloring composition.
- a dispersing aid such as a pigment derivative, a resin-type dispersant, or a surfactant may be contained as appropriate. Since the dispersing aid has a great effect of preventing the reaggregation of the colorant after dispersion, the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersing aid has good brightness and viscosity stability. get better.
- dye derivatives include compounds obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group optionally having a substituent into an organic pigment, anthraquinone, acridone or triazine. 63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, JP-A-2001-335717, JP-A-2003- 128669, JP 2004-091497, JP 2007-156395, JP 2008-094873, JP 2008-094986, JP 2008-095007, JP 2008-195916 Those described in publications, Japanese Patent No. 4585781 and the like can be used, and these can be used alone or in combination of two or more.
- the content of the pigment derivative is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and most preferably 3 parts by mass or more with respect to 100 parts by mass of the colorant.
- the amount is preferably 40 parts by mass or less, more preferably 35 parts by mass or less.
- the resin-type dispersant has a colorant affinity site having a property of adsorbing to the colorant and a site compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant into the colorant carrier. It works to stabilize the Specific examples of resin-type dispersants include polyurethanes, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts.
- Oily dispersants such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, water-soluble such as polyvinylpyrrolidone Resins, water-soluble polymer compounds, polyesters, modified polyacrylates, ethylene oxide/propylene oxide addition compounds, phosphoric acid esters, etc. are used, and these can be used alone or in combination of two or more. It is not necessarily limited to these.
- resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by BYK-Chemie Japan.
- Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalenesulfonate, sodium alkyldiphenylether disulfonate.
- a resin-type dispersant or surfactant When a resin-type dispersant or surfactant is added, it is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass, per 100 parts by mass of the colorant. If the amount of the resin-type dispersant and surfactant is less than 0.1 parts by mass, it is difficult to obtain the effect of addition. If the content is more than 55 parts by mass, the excess dispersant affects dispersion may affect
- a method for producing a photosensitive coloring composition for example, first prepares a colorant dispersion, and then adds a photopolymerizable monomer, a photopolymerization initiator, and other components used as necessary. and methods to do so.
- the colorant dispersion is prepared, for example, by dispersing the colorant in a colorant carrier such as a binder resin and/or an organic solvent, preferably together with a dispersing aid, using a kneader, a two-roll mill, a three-roll mill, a ball mill, or a horizontal sand mill. , a vertical sand mill, an annular bead mill, or an attritor.
- the plurality of colorants may be dispersed in the colorant carrier at the same time, or the colorant dispersions may be separately prepared and then mixed.
- the coloring agent has high solubility, specifically, when the coloring agent has high solubility in the organic solvent to be used, and when it is dissolved by stirring and no foreign matter is confirmed, it is manufactured by finely dispersing as described above. No need.
- the present photosensitive coloring composition is separated by means of centrifugation, filtration with a sintered filter or membrane filter, or the like, to obtain coarse particles of 5 ⁇ m or more, preferably 1 ⁇ m or more, more preferably 0.5 ⁇ m or more, particularly preferably It is preferable to remove coarse particles of 0.3 ⁇ m or more and mixed dust.
- FIG. 1 is a schematic cross-sectional view of the organic EL display device.
- This organic EL display device 10 has an organic EL layer 2 and a color filter on a silicon substrate 1 on which drive elements are formed. It may have a layer 4 and a cover glass 5, and may have a flat layer (planar) between the organic EL layer 2 and the color filter 3 (not shown). Details of each configuration of the organic EL display device will be described below.
- the color filter 3 is formed on the organic EL layer and has at least red pixels, green pixels, and blue pixels (3a, 3b, 3c).
- the pixel is a cured product of the photosensitive coloring composition described above.
- the color filter may also have magenta pixels, cyan pixels, yellow pixels, or other pixels.
- a color filter is formed on the organic EL layer 2 or on a flat layer provided as necessary.
- the fine uneven surface of the organic EL layer can be planarized.
- a well-known curable resin can be used for the flat layer, preferably an ultraviolet curable resin, and if necessary, a thermosetting resin may be used together.
- the ultraviolet curable resin is not particularly limited, an acrylic resin exhibiting sensitivity to the i-line (wavelength of 365 nm) is preferable.
- the method of forming the pixels constituting the color filter is not particularly limited, the following method can be used, for example.
- a coating method such as a spray coating method, a dip coating method, a bar coating method, a call coating method, a spin coating method, and a coating film to form
- a mask of a predetermined pattern to photopolymerize a photopolymerizable monomer or a photosensitive resin to form a cured coating film.
- Light sources used for exposure include, for example, ultraviolet light from low-pressure mercury lamps, high-pressure mercury lamps, metal halide lamps, electron beams, and the like.
- the amount of exposure may be appropriately adjusted depending on the light source used, the thickness of the coating film, and the like. Moreover, in order to accelerate the polymerization reaction after exposure, heat treatment may be performed. Since the photosensitive coloring composition has low-temperature curability, it can be sufficiently cured even by heat treatment at 100° C. or less.
- the film thickness of the pixels forming the color filter is 0.5 ⁇ m to 2.0 ⁇ m, more preferably 1.0 to 2.0 ⁇ m.
- the red, green, and blue pixels forming the color filter have the following spectral characteristics, so that a high-quality organic EL display device with high luminance and high color reproducibility can be obtained.
- Red pixel the maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.5% or less, and the maximum transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%.
- Green pixel Maximum light transmittance in the wavelength range of 400 nm to 470 nm is 2% or less, maximum light transmittance in the wavelength range of 525 to 535 nm is 67% or more, short wavelength side 50% half value wavelength is 497 to 507 nm, and long wavelength The side 50% half-value wavelength is 554 to 581 nm.
- Blue pixel Maximum transmittance of light in the wavelength range of 500 nm to 560 nm is less than 20%. Since each pixel of the color filter has the above spectral characteristics, the color filter has a wide color gamut.
- the organic EL layer can be formed of an organic light-emitting single layer or multiple layers containing a light-emitting material.
- a general three-layer structure in which a hole transport layer, an electron transporting organic light-emitting layer, and an electron transport layer are sequentially stacked, a hole (electron) injection layer, a hole (A multi-layer structure may be employed in which an electron) transport layer and a layer having separate injection and transport functions are provided, or a layer for blocking hole (electron) transport is provided.
- An example of the organic EL layer is a structure in which an anode, an organic layer, and a cathode are laminated in order from the silicon substrate side, and airtightly covered with a sealing layer.
- the anode is provided on a silicon substrate and is composed of a conductive material with a large work function.
- conductive materials with a large work function include nickel, silver, gold, platinum, palladium, selenium, rhodium, ruthenium, iridium, rhenium, tungsten, molybdenum, chromium, tantalum, niobium, alloys thereof, and tin oxide ( SnO2), indium tin oxide (ITO), zinc oxide, titanium oxide, and the like.
- the cathode is constructed using a conductive material with a small work function.
- a conductive material for example, an alloy of an active metal such as Li, Mg, or Ca and a metal such as Ag, Al, or In, or a structure in which these are laminated can be used.
- a thin compound layer of active metal such as Li, Mg or Ca and halogen such as fluorine or bromine or oxygen may be inserted between the organic layer.
- the anode and cathode are patterned into shapes suitable for the driving method of the display device.
- the drive system of the organic EL display device is a simple matrix type
- the anode and the cathode are formed in stripes that intersect with each other, and the intersection of these stripes becomes the organic EL element.
- the organic layer has at least a white light-emitting layer, and is usually composed of a plurality of layers of organic layers. It may have a charge transport layer such as a hole transport layer that transports holes and an electron transport layer that transports electrons to the white light emitting layer.
- Emission characteristics of white color should include emission in at least three regions of red region (600 nm to 780 nm), green region (475 nm to 600 nm), and blue region (380 nm to 475 nm).
- the number of emission peaks does not necessarily need to be three or more.
- two emission peaks may be used as long as they emit light in the above region.
- the material constituting such a white light-emitting layer is not particularly limited as long as it emits fluorescence or phosphorescence. Moreover, the light-emitting material may have a hole-transport property or an electron-transport property. Examples of light-emitting materials include dye-based materials, metal complex-based materials, and polymer-based materials.
- dye-based materials examples include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, silole derivatives, thiophene ring compounds, pyridine. Ring compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, trifmanylamine derivatives, oxadiazole dimers, pyrazoline dimers and the like can be mentioned.
- metal complex-based materials examples include aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazole zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, and europium complexes, or Al, Zn, and Be as central metals. or a rare earth metal such as Tb, Eu, and Dy, and a ligand having an oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, quinoline structure, or the like.
- polymer materials include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and the dye materials and metal complex materials described above. Examples thereof include molecularized ones.
- Examples of the method for forming the white light-emitting layer include a vapor deposition method, a printing method, an inkjet method, a spin coating method, a casting method, a dipping method, a bar coating method, a blade coating method, a roll coating method, a gravure coating method, and flexographic printing. method, spray coating method, self-assembly method (alternate adsorption method, self-assembled monolayer method), and the like.
- vapor deposition, spin coating, and inkjet are preferably used, and the film thickness of the white light-emitting layer is usually about 5 nm to 5 ⁇ m.
- the organic EL layer may have a hole injection layer formed between the white light emitting layer and the anode. This is because the provision of the hole-injection layer stabilizes the injection of holes into the white light-emitting layer, and can increase the light emission efficiency.
- a material for forming the hole injection layer a material generally used for the hole injection layer of an organic EL device can be used. Further, the material for forming the hole injection layer may be any material that has either hole injection properties or electron barrier properties.
- materials for forming the hole injection layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, and conductive polymer oligomers such as thiophene oligomers.
- examples of materials for forming the hole injection layer include porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds.
- the film thickness of the hole injection layer is usually about 5 nm to 1 ⁇ m.
- the organic EL layer may have an electron injection layer formed between the white light emitting layer and the cathode.
- the electron injection layer By providing the electron injection layer, the injection of electrons into the white light emitting layer can be stabilized and the luminous efficiency can be improved.
- Materials for forming the electron injection layer include, for example, nitro-substituted fluorene derivatives, anthraquinodimethane derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, heterocyclic tetracarboxylic acid anhydrides such as naphthalene perylene, carbodiimides, and fluorenylidene methane derivatives.
- anthraquinodimethane and anthrone derivatives oxadiazole derivatives, thiazole derivatives in which the oxygen atom of the oxadiazole ring of the oxadiazole derivative is substituted with a sulfur atom, and quinoxaline derivatives having a quinoxaline ring known as an electron-withdrawing group.
- metal complexes of 8-quinolinol derivatives such as tris(8-quinolinol)aluminum, phthalocyanines, metal phthalocyanines, and distyrylpyrazine derivatives.
- ⁇ Preparation of coloring agent> (Micronized red pigment (PR177-1)) dianthraquinone pigment C.I. I. 150 parts of Pigment Red 177 (“Cinilex Red SR3C” manufactured by CINIC Chemicals), 1500 parts of sodium chloride and 250 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60° C. for 10 hours.
- Pigment Red SR3C manufactured by CINIC Chemicals
- the kneaded mixture is poured into hot water, stirred for 1 hour while heating to about 70°C to form a slurry, filtered and washed with water to remove salt and diethylene glycol, dried at 80°C for a day and night, and pulverized.
- anthraquinone-based fine pigment PR177-1
- this kneaded product is put into 8000 parts of hot water and stirred for 2 hours while heating to 80°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night. , to obtain a diketopyrrolopyrrole micronized red pigment (PR254-1).
- C.I. I. Pigment Yellow 185 (BASF "Paliotol Yellow L 1155") 200 parts, sodium chloride 1000 parts, and diethylene glycol 100 parts were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 100° C. for 6 hours. Next, this kneaded product is put into 5 liters of hot water and stirred for 1 hour while heating to 70°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80°C for a day and night. , to obtain a finely divided yellow pigment (PY185-1).
- C.I. I. Pigment Yellow 185 BASF "Paliotol Yellow L 1155” 200 parts, sodium chloride 1000 parts, and diethylene glycol 100 parts were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho)
- C.I. I. Pigment Yellow 185 (BASF "Paliotol Yellow L 1155") 95 parts, rosin maleic acid resin (manufactured by Arakawa Chemical Industries, Ltd. "Malquido 32") 10 parts, sodium chloride 1200 parts, and diethylene glycol 120 parts are added to a stainless steel 1 gallon kneader ( (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 60° C. for 8 hours.
- a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 60° C. for 8 hours.
- this kneaded product is put into 8000 parts of hot water and stirred for 1 hour while heating to about 70°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80°C for a day and night. to obtain 105 parts of a yellow fine pigment (PY185-2).
- PG36-1 phthalocyanine pigment C.I. I. 120 parts of Pigment Green 36 ("Lionor Green 6YK” manufactured by Toyocolor Co., Ltd.), 1600 parts of sodium chloride, and 270 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 70° C. for 12 hours. This mixture was poured into 5,000 parts of hot water and stirred for 1 hour while heating to about 70°C to form a slurry, which was repeatedly filtered and washed with water to remove salt and solvent. A finely divided pigment (PG36-1) was obtained.
- PG62-1 phthalocyanine green pigment C.I. I. 200 parts of Pigment Green 62 (manufactured by Toyocolor Co., Ltd.), 1400 parts of sodium chloride and 360 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product is put into 8000 parts of hot water and stirred for 2 hours while heating to 80°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night. , to obtain a finely divided phthalocyanine green pigment (PG62-1).
- PG63-1 phthalocyanine green pigment C.I. I. 200 parts of Pigment Green 63 (manufactured by Toyocolor Co., Ltd.), 1400 parts of sodium chloride and 360 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product is put into 8000 parts of hot water and stirred for 2 hours while heating to 80°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night. , to obtain a phthalocyanine-based micronized green pigment (PG63-1).
- this kneaded product is put into 8000 parts of hot water and stirred for 2 hours while heating to 80°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night. , to obtain a finely divided phthalocyanine blue pigment (PB15:6-1).
- PB15:3-1 phthalocyanine blue pigment
- phthalocyanine blue pigment C.I. Pigment Blue 15:3, "LIONOL BLUE FG-7351” manufactured by Toyocolor Co., Ltd.
- 600 parts of sodium chloride 600 parts of diethylene glycol
- 600 parts of diethylene glycol 600 parts of sodium chloride
- diethylene glycol 600 parts of diethylene glycol
- a stainless steel 1 gallon kneader manufactured by Inoue Seisakusho
- this kneaded product is put into 5 liters of hot water, stirred for 1 hour while heating to 70° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80° C. for a day and night. to obtain a finely divided phthalocyanine blue pigment (PB15:3-1).
- this kneaded product is put into 8000 parts of hot water and stirred for 2 hours while heating to 80°C to form a slurry, which is repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 85°C for a day and night. , to obtain a dioxazine-based finely divided purple pigment (PV23-1).
- a salt-forming compound (V) was prepared from Acid Red 289 and a quaternary ammonium salt compound, tristearylmonomethylammonium chloride.
- Resin Dispersant Solution 1 Photosensitive Resin Into a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser and a stirrer, 8 parts of 3-mercapto-1,2-propanediol, 12 parts of pyromellitic anhydride, 80 parts of propylene glycol monomethyl ether acetate (PGMAc) and 0.2 parts of monobutyltin oxide as a catalyst were charged, and after purging with nitrogen gas, reaction was carried out at 120° C. for 5 hours (first step). It was confirmed by acid value measurement that 95% or more of the acid anhydride was half-esterified.
- PGMAc propylene glycol monomethyl ether acetate
- MMA methyl methacrylate
- tBA t-butyl acrylate
- EA ethyl acrylate
- MAA methacrylic acid
- BzMA benzyl methacrylate
- HEMA 2-hydroxyethyl methacrylate 50 parts of (HEMA) was charged, the inside of the reaction vessel was heated to 80° C., 1 part of 2,2′-azobis(2,4-dimethylvaleronitrile) was added, and the mixture was reacted for 12 hours (second step). Solid content measurement confirmed that 95% had reacted.
- Resin-type dispersant solution 2 30 parts of ethyl acrylate, 20 parts of tert-butyl acrylate, and 40 parts of 2-methyl methacrylate were charged into a reaction vessel equipped with a non-photosensitive gas inlet tube, a thermometer, a condenser, and a stirrer. , was replaced with nitrogen gas. The inside of the reaction vessel was heated to 80° C., and a solution of 6 parts of 3-mercapto-1,2-propanediol and 0.1 part of 2,2′-azobisisobutyronitrile dissolved in 45.7 parts of cyclohexanone was prepared. was added and reacted for 10 hours. Solid content measurement confirmed that 95% had reacted.
- the weight average molecular weight was 4,000.
- binder resin ⁇ Production of binder resin> (Acrylic resin solution (D-1)): photosensitive resin 100 parts of propylene glycol monomethyl ether acetate was placed in a separable 4-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, and a stirrer, and the mixture was placed in the vessel. The mixture was heated to 120° C. while introducing nitrogen gas, and at the same temperature, 5.2 parts of styrene, 35.5 parts of glycidyl methacrylate, 41.0 parts of dicyclopentanyl methacrylate, and 1. azobisisobutyronitrile were added from a dropping tube.
- Photosensitive Resin 182 g of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen introduction tube, and the atmosphere in the flask was adjusted. After converting air to nitrogen, heating to 100° C., 70.5 g (0.40 mol) of benzyl methacrylate, 43.0 g (0.5 mol) of methacrylic acid, monomethacrylate with a tricyclodecane skeleton (Hitachi Chemical Co., Ltd.
- Pigment dispersion (PR-1) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PR-1) having a non-volatile content of 20% by weight.
- Propylene glycol monomethyl ether acetate 72.2 parts
- Pigment dispersion (PR-2) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PR-2) having a non-volatile content of 20% by weight.
- Propylene glycol monomethyl ether acetate 72.2 parts
- Pigment dispersion (PY-1) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PY-1) having a non-volatile content of 20% by weight.
- Pigment dispersion (PY-2) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PY-2) having a non-volatile content of 20% by weight.
- Pigment dispersion (PY-3) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PY-3) having a non-volatile content of 20% by weight.
- Pigment dispersion (PY-4) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PY-4) having a non-volatile content of 20% by weight.
- Pigment dispersion (PG-1) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PG-1) having a non-volatile content of 20% by weight.
- Pigment dispersion (PG-2) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PG-2) having a non-volatile content of 20% by weight.
- Resin type dispersant solution 2 (non-photosensitive) 12.5 parts
- Propylene glycol monomethyl ether acetate 72.5 parts
- Pigment dispersion (PG-3) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PG-3) having a non-volatile content of 20% by weight.
- Resin type dispersant solution 2 (non-photosensitive) 12.5 parts
- Propylene glycol monomethyl ether acetate 72.5 parts
- Pigment dispersion (PG-4) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PG-4) having a non-volatile content of 20% by weight.
- Resin type dispersant solution 2 (non-photosensitive) 12.5 parts
- Propylene glycol monomethyl ether acetate 72.5 parts
- Pigment dispersion (PG-5) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PG-5) having a non-volatile content of 20% by weight.
- Pigment dispersion (PB-1) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PB-1) having a non-volatile content of 20% by weight.
- Pigment dispersion (PB-2) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PB-2) having a non-volatile content of 17% by weight.
- Pigment Dispersion (PV-1) After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), 5.0 ⁇ m to prepare a pigment dispersion (PV-1) having a non-volatile content of 17% by weight.
- Photopolymerizable monomer B-1 trimethylolpropane EO-modified triacrylate ("Aronix M-350" manufactured by Toagosei Co., Ltd.)
- Photopolymerizable monomer B-2 trimethylolpropane triacrylate ("Aronix M-309" manufactured by Toagosei Co., Ltd.)
- Photopolymerizable monomer B-3 pentaerythritol tri and tetraacrylate ("Aronix M-306" manufactured by Toagosei Co., Ltd.)
- Photopolymerizable monomer B-4 dipentaerythritol hexaacrylate ("Aronix M-402" manufactured by Toagosei Co., Ltd.)
- Photopolymerization initiator C-4 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (manufactured by BASF Japan Ltd. "IRGACURE-907") ⁇ Leveling agent> Leveling agent: A solution prepared by dissolving 1 part of "FZ-2122" manufactured by Dow Corning Toray Co., Ltd. in 99 parts of propylene glycol monomethyl ether acetate (PGMAc) ⁇ solvent (S)> Solvent S-1: Propylene glycol monomethyl ether acetate Solvent S-2: Tripropylene glycol monomethyl ether Solvent S-3: 3-methoxy-1-butanol
- a TFT layer was formed on a silicon substrate using a known method such as a sputtering method or an etching method. Furthermore, after forming a white organic EL element on the TFT layer by using a known method such as vapor deposition, silicon nitride was coated by a CVD method to form an organic EL element substrate.
- the green photosensitive coloring composition is applied with a spinner so that the film thickness of the cured finish is 1.5 ⁇ m, and the color filter is applied through a pattern mask through ultraviolet exposure, alkali development, water washing and drying steps. of green layer (G) was formed. After that, it was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the green layer (G) of the color filter.
- the red photosensitive coloring composition is applied with a spinner so that the film thickness of the cured finish becomes 1.5 ⁇ m, and a pattern mask is formed.
- a red layer (R) of a color filter was temporarily formed through ultraviolet exposure, alkali development, water washing and drying steps. Then, it was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the red layer (R) of the color filter.
- the blue photosensitive coloring composition is applied with a spinner so that the film thickness of the cured finish is 1.5 ⁇ m, and is applied through a pattern mask.
- the blue layer (B) of the color filter was temporarily formed through the steps of ultraviolet exposure, alkali development, water washing and drying. Thereafter, the composition was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the blue layer (B) of the color filter, thereby producing a color filter.
- Tables 8 to 11 show the combinations of photosensitive coloring compositions used in producing the color filters and organic EL display devices of each example and comparative example. Tables 8 to 11 show the appearance of the obtained color filters and organic EL display devices and the results of spectral transmittance measurement.
- ⁇ Pixel shape (linearity)> Each photosensitive coloring composition was coated on a silicon wafer substrate having a diameter of 200 mm using a spin coater so that the thickness after drying was 1.50 ⁇ m, and dried at 70° C. for 1 minute to obtain a substrate.
- i-line stepper exposure apparatus FPA-3000i5+ manufactured by Canon Inc.
- Exposure was through a photomask having a square opening of 2.40 ⁇ m square.
- TMAH a 2.38% aqueous solution of tetramethylammonium hydroxide manufactured by Tama Kagaku Kogyo Co., Ltd.
- the linearity of the pixels formed by the apertures was observed using a scanning electron microscope (“S-3000N” manufactured by Hitachi High-Tech Co., Ltd.) and evaluated according to the following criteria.
- S-3000N scanning electron microscope
- Each photosensitive coloring composition was coated on a silicon wafer substrate having a diameter of 200 mm using a spin coater so that the thickness after drying was 1.50 ⁇ m, and dried at 70° C. for 1 minute to obtain a substrate.
- an i-line stepper exposure apparatus FPA-3000i5+ manufactured by Canon Inc.
- Exposure was through a photomask having a square opening of 2.40 ⁇ m square.
- TMAH a 2.38% aqueous solution of tetramethylammonium hydroxide manufactured by Tama Kagaku Kogyo Co., Ltd.
- the exposed film was puddle-developed with 2.38% TMAH (a 2.38% aqueous solution of tetramethylammonium hydroxide manufactured by Tama Kagaku Kogyo Co., Ltd.) for 1 minute.
- the substrate was rinsed with pure water using a spin shower for 20 seconds, and then spin-dried.
- S-3000N manufactured by Hitachi High-Tech
- ⁇ No development residue in the non-exposed area (preferable level for practical use)
- ⁇ Development residue is present in part of the non-exposed area (practical level)
- ⁇ Development residue is present on the entire surface of the non-exposed area (level not suitable for practical use)
- Each photosensitive coloring composition is spin-coated on a glass substrate having a length of 100 mm ⁇ width of 100 mm and a thickness of 0.7 mm using a spin coater so that the dry film thickness is 1.50 ⁇ m, and dried at 70 ° C. for 1 minute. did.
- the resulting film was exposed to light of 3000 mJ/cm 2 with an ultra-high pressure mercury lamp having an i-ray illuminance of 30 mW/cm 2 through a photomask in which a 400 ⁇ m square square pattern mask pattern was arranged. After the pattern-exposed film was developed with 2.38% TMAH, the unexposed portion was washed with pure water.
- ⁇ Eab * ((L * (2)-L * (1)) 2 +(a * (2)-a * (1)) 2 +(b * (2)-b * (1)) 2 ) 1 /2
- ⁇ Eab * is less than 3.0 (preferable level for practical use)
- ⁇ Eab * is 3.0 or more and less than 6.0 (practical level)
- ⁇ Eab * is 6.0 or more (level not suitable for practical use)
- the NTSC area ratio (the ratio of the color gamut of the organic EL display device of Example or Comparative Example to the color gamut defined by the NTSC standard) was calculated from the obtained chromaticities of red, green, and blue. Color reproducibility can be evaluated by NTSC chromaticity.
- NTSC area ratio 93% or more were evaluated as ⁇ , those with an NTSC area ratio of 90% or more were evaluated as ⁇ , those with 85% or more and less than 90% were evaluated as ⁇ , and those with less than 85% were evaluated as x. If the NTSC area ratio is less than 85%, the image will appear to lack sharpness when displayed as an organic EL display device, so it was judged not to be practical.
- the luminance (W ⁇ L) of 330 cd/m 2 or more when all pixels of red, green, and blue are lit and displayed in white is ⁇ , and 300 cd/m 2 or more and less than 330 cd/m 2 was evaluated as ⁇ , 280 cd/m 2 or more and less than 300 cd/m 2 was evaluated as ⁇ , and less than 280 cd/m 2 was evaluated as x. If the luminance is less than 280 cd/m 2 , the image will appear dark when displayed, so it was determined that this is not practical as an organic EL display device.
- ⁇ Pixel crack> Each photosensitive coloring composition was coated on a silicon wafer substrate having a diameter of 200 mm using a spin coater so that the thickness after drying was 1.50 ⁇ m, and dried at 70° C. for 1 minute to obtain a substrate.
- i-line stepper exposure apparatus FPA-3000i5+ manufactured by Canon Inc.
- Exposure was through a photomask having a square opening of 2.40 ⁇ m square.
- TMAH a 2.38% aqueous solution of tetramethylammonium hydroxide manufactured by Tama Kagaku Kogyo Co., Ltd.
- the substrate was rinsed with pure water using a spin shower for 20 seconds, and then spin-dried. After spin-drying, it was baked on a hot plate at 90° C. for 5 minutes to obtain a monochromatic patterned substrate.
- the second and third colors were also added in the same manner to obtain a patterned substrate in which three colors of RGB were added.
- the pixel surface was observed using a scanning electron microscope ("S-3000N" manufactured by Hitachi High-Tech) and evaluated according to the following criteria.
- S-3000N manufactured by Hitachi High-Tech
- the present invention can be used as an organic EL display device for electronic devices such as smart glasses, head-mounted displays, and electronic viewfinders.
Abstract
Description
駆動素子が形成されたシリコン基板上に、有機EL層と、カラーフィルタと、を有する、有機EL表示装置であって、
前記カラーフィルタが、赤色画素と、緑色画素と、青色画素とを含む画素を有し、
前記画素の膜厚が1.5μmのときの、
前記赤色画素の分光透過率が、波長450nm~560nmの範囲における光の最大透過率が0.5%以下、50%半値波長が593nm~603nm、かつ波長600nm~700nmの範囲の光の最大透過率が80%以上100%未満であり、
前記緑色画素の分光透過率が、波長400nm~470nmの範囲における光の最大透過率が2%以下、波長525~535nmの光の最大透過率が67%以上、短波長側50%半値波長が497~507nm、かつ長波長側50%半値波長が554~581nmであり、
前記青色画素の分光透過率が、波長500nm~560nmの範囲における光の最大透過率が20%未満であり、
前記画素が、着色剤(A)と、光重合性単量体(B)と、光重合開始剤(C)と、樹脂(D)とを含有する感光性着色組成物の硬化物であり、
前記赤色画素は、着色剤(A)がピグメントレッド177およびその他着色剤を含み、
前記緑色画素は、着色剤(A)がピグメントイエロー185、ならびに、ピグメントグリーン36、ピグメントグリーン62、ピグメントグリーン63およびピグメントグリーン59からなる群より選択される1種以上を含み、その他着色剤を含んでいてもよく、かつ緑色画素の着色剤(A)中、ピグメントイエロー185の含有量が49重量%~59重量%であり、
前記青色画素が、ピグメントブルー15:6およびその他着色剤を含み、
赤色画素において、前記その他着色剤が、ピグメントレッド254、およびピグメントイエロー139からなる群より選択される1種以上を含み、
緑色画素において、前記その他着色剤が、ピグメントブルー15:3を含み、
青色画素において、前記その他着色剤が、ピグメントバイオレット23、およびキサンテン系染料からなる群より選択される1種以上を含み、
前記光重合性単量体(B)が下記一般式(1)で表される化合物を含み、
光重合開始剤(C)がオキシムエステル系光重合開始剤を含む。
一般式(1)
[CH2=CHC(=O)-(OCmH2m)n-OCH2]3-CR
(一般式(1)中、mは1~3の整数を表し、nは0~2の整数を表し、複数あるm及びnは同一であっても異なってもよい。
Rは-CH2CH3、-CH2OH、-CH2O(C=O)C=CH2から選ばれる置換基を表す。)
前記赤色画素を構成する硬化物が、着色剤(A-1)ピグメントレッド177、着色剤(A-2)ピグメントレッド254、および着色剤(A-3)ピグメントイエロー139を含有し、
前記赤色画素における着色剤(A)中、
着色剤(A-1)の含有量が55重量%~65重量%、
着色剤(A-2)の含有量が15重量%~25重量%、
および着色剤(A-3)の含有量が15重量%~25重量%であり、
前記緑色画素を構成する硬化物が、着色剤(A-4)ピグメントイエロー185、着色剤(A-5)ピグメントグリーン36、着色剤(A-6)ピグメントグリーン62、着色剤(A-11)ピグメントグリーン63、着色剤(A-12)ピグメントグリーン59、及び着色剤(A-7)ピグメントブルー15:3を下記(I)~(IV)の組み合わせで含有し、
(I)着色剤(A-4)、着色剤(A-5)および着色剤(A-7)
(II)着色剤(A-4)および着色剤(A-6)
(III)着色剤(A-4)および着色剤(A-11)
(IV)着色剤(A-4)および着色剤(A-12)
前記緑色画素における着色剤(A)中、
着色剤(A-4)の含有量が49重量%~59重量%、
着色剤(A-5)、着色剤(A-6)、着色剤(A-11)または着色剤(A-12)の含有量が33重量%~51重量%、
および着色剤(A-7)の含有量が0重量%~13重量%であり、
前記青色画素を構成する硬化物が、着色剤(A-8)ピグメントブルー15:6、着色剤(A-9)ピグメントバイオレット23、および着色剤(A-10)キサンテン系染料を含有し、
前記青色画素における着色剤(A)中、
着色剤(A-8)の含有量が58重量%~64重量%、
着色剤(A-9)の含有量が12重量%~20重量%、
および着色剤(A-10)の含有量が17重量%~25重量%である。
Raは、炭素数2~6のアルキル基であり、Rbは、炭素数4~10のアルキル基であり、Rcは、少なくとも炭化水素環又は複素環を含み、更に炭素数1~4のアルキレン鎖、チオエーテル結合(-S-)、エーテル結合(-O-)、及びカルボニル結合(-CO-)から選択される少なくとも1種の2価の連結基を含んでいても良い基であり、RbとRcとは互いに異なる置換基である。Rd及びReはそれぞれ独立に炭素数1~6のアルキル基である。)
なお本発明において数値範囲を示す「~」は、特に断りがない限り、その前後に記載された数値を下限値及び上限値として含むことを意味する。
本発明において、「50%半値波長」とは、400nmから700nmの波長領域において分光透過率が50%となるときの波長(nm)を表す。「短波長側50%半値波長」は短波長(400nm)から測定を開始して長波長側にスキャンしたときに分光透過率がはじめて50%となるときの波長(nm)を表し、「長波長側50%半値波長」は長波長(700nm)から測定を開始して短波長側にスキャンしたときに分光透過率がはじめて50%となるときの波長(nm)を表す。
「(メタ)アクリロイル」、「(メタ)アクリル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、又は「(メタ)アクリルアミド」と表記した場合には、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタクリロイル」、「アクリル及び/又はメタクリル」、「アクリル酸及び/又はメタクリル酸」、「アクリレート及び/又はメタクリレート」、又は「アクリルアミド及び/又はメタクリルアミド」を表すものとする。また、本明細書に挙げる「C.I.」は、カラーインデックス(C.I.)を意味する。
駆動素子が形成されたシリコン基板上に、有機EL層と、カラーフィルタと、を有する、有機EL表示装置であって、
前記カラーフィルタが、赤色画素と、緑色画素と、青色画素とを含む画素を有し、
前記画素の膜厚が1.5μmのときの、
前記赤色画素の分光透過率が、波長450nm~560nmの範囲における光の最大透過率が0.5%以下、50%半値波長が593nm~603nm、かつ波長600nm~700nmの範囲の光の最大透過率が80%以上100%未満であり、
前記緑色画素の分光透過率が、波長400nm~470nmの範囲における光の最大透過率が2%以下、波長525~535nmの光の最大透過率が67%以上、短波長側50%半値波長が497~507nm、かつ長波長側50%半値波長が554~581nmであり、
前記青色画素の分光透過率が、波長500nm~560nmの範囲における光の最大透過率が20%未満であり、
前記画素が、着色剤(A)と、光重合性単量体(B)と、光重合開始剤(C)と、樹脂(D)とを含有する感光性着色組成物の硬化物であり、
前記赤色画素は、着色剤(A)がピグメントレッド177およびその他着色剤を含み、
前記緑色画素は、着色剤(A)がピグメントイエロー185、ならびに、ピグメントグリーン36、ピグメントグリーン62、ピグメントグリーン63およびピグメントグリーン59からなる群より選択される1種以上を含み、その他着色剤を含んでいてもよく、かつ緑色画素の着色剤(A)中、ピグメントイエロー185の含有量が49重量%~59重量%であり、
前記青色画素が、ピグメントブルー15:6およびその他着色剤を含み、
赤色画素において、前記その他着色剤が、ピグメントレッド254、およびピグメントイエロー139からなる群より選択される1種以上を含み、
緑色画素において、前記その他着色剤が、ピグメントブルー15:3を含み、
青色画素において、前記その他着色剤が、ピグメントバイオレット23、およびキサンテン系染料からなる群より選択される1種以上を含み、
前記光重合性単量体(B)が下記一般式(1)で表される化合物を含み、
光重合開始剤(C)がオキシムエステル系光重合開始剤を含む。
一般式(1)
[CH2=CHC(=O)-(OCmH2m)n-OCH2]3-CR
(一般式(1)中、mは1~3の整数を表し、nは0~2の整数を表し、複数あるm及びnは同一であっても異なってもよい。
Rは-CH2CH3、-CH2OH、-CH2O(C=O)C=CH2から選ばれる置換基を表す。)
また、本有機EL表示装置は、カラーフィルタが上記特定の分光特性を有する画素を用いることで、xy色度図における、R(赤)、G(緑)、B(青)、を結んだ色三角形により規定される領域の面積が広がり、色再現域の広い(即ち高色再現性)の表示装置となる。
以下、本有機EL表示装置について、まず画素形成用の感光性着色組成物を説明し、次いで、有機EL表示装置の構成について説明する。
上記カラーフィルタの各画素は、着色剤(A)、光重合性単量体(B)、光重合開始剤(C)、及び樹脂(D)を含む感光性着色組成物の硬化物である。当該感光性着色組成物は、前記光重合性単量体(B)が少なくとも一般式(1)で表される化合物を含み、光重合開始剤(C)が少なくともオキシムエステル系光重合開始剤を含むことを特徴とする。これにより、高輝度かつ高色再現性を有し、着色剤濃度が高くても現像工程での画素密着性が良好で画素直線性の良好な画素が得られる。
感光性着色組成物は、少なくとも着色剤(A)、光重合性単量体(B)、光重合開始剤(C)、及び樹脂(D)を含有するものであり、必要に応じて更に他の成分を含有してもよいものである。以下各成分の詳細について説明する。
着色剤(A)は、カラーフィルタの画素を後述する特定の分光特性が得られるように色調を調節するものであり、所定の画素の色味に応じて、公知の顔料及び染料の中から、適宜選択して用いることができる。
顔料としては、有機顔料、無機顔料のいずれも好適に用いることができる。また、本感光性着色組成物は、低温硬化性に優れているため、顔料と比較して耐熱性の低い染料であっても好適に用いることができる。
染料としては、酸性染料、直接染料、塩基性染料、造塩染料、油溶性染料、分散染料、反応染料、媒染染料、建染染料、硫化染料等のいずれも用いることができる。また、これらの誘導体や、染料をレーキ化したレーキ顔料の形態であってもよい。
以下、色ごとにより具体的に着色剤(A)について説明する。
本有機EL表示装置は、赤色画素用着色剤として、C.I.ピグメントレッド177(着色剤(A-1)ともいう)とその他着色剤とを組み合わせて用いる。ピグメントレッド177と、その他着色剤とを組み合わせることで、画素の膜厚を1.5μmとしたときの赤色画素の分光透過率を、波長450nm~560nmの範囲における光の最大透過率が0.5%以下、50%半値波長が593nm~603nm、かつ波長600nm~700nmの範囲の光の最大透過率が80%以上100%未満に調整しやすくなる。
着色剤(A-1)、(A-2)、(A-3)を組み合わせて用いる場合、着色剤(A)中、着色剤(A-1)の含有量を55重量%~65重量%、着色剤(A-2)の含有量を15重量%~25重量%、着色剤(A-3)の含有量を15重量%~25重量%とすることが好ましい。
本有機EL表示装置において緑色画素用着色剤は、C.I.ピグメントイエロー185(着色剤(A-4)ともいう)ならびに、ピグメントグリーン36、ピグメントグリーン62、ピグメントグリーン63およびピグメントグリーン59からなる群より選択される1種以上を含み、着色剤(A)中のピグメントイエロー185の含有量を49重量%~59重量%として用いる。ピグメントイエロー185を上記割合で用いることで、画素の膜厚を1.5μmとしたときの緑色画素の分光透過率を、波長400nm~470nmの範囲における光の最大透過率が2%以下、波長525~535nmの光の最大透過率が67%以上、短波長側50%半値波長が497~507nm、かつ長波長側50%半値波長が554~581nmに調整しやすくなる。
(I)着色剤(A-4)、着色剤(A-5)および着色剤(A-7)
(II)着色剤(A-4)および着色剤(A-6)
(III)着色剤(A-4)および着色剤(A-11)
(IV)着色剤(A-4)および着色剤(A-12)
本有機EL表示装置は、青色画素用着色剤として、ピグメントブルー15:6(着色剤(A-8)ともいう)とその他着色剤とを組み合わせて用いる。ピグメントブルー15:6とその他着色剤とを組み合わせることで、画素の膜厚を1.5μmとしたときの青色画素の分光透過率を、波長500nm~560nmの範囲における光の最大透過率が20%未満に調整しやすくなる。
中でも、発色性の高いローダミン系油溶性染料であるC.I.ソルベントレッド35、C.I.ソルベントレッド36、C.I.ソルベントレッド49、C.I.ソルベントレッド109、C.I.ソルベントレッド237、C.I.ソルベントレッド246、C.I.ソルベントバイオレット2がより好ましい。
中でも、耐熱性、耐光性の面で、C.I.アシッドレッド87、C.I.アシッドレッド92、C.I.アシッドレッド388、C.I.アシッドレッド52(アシッドローダミン)、C.I.アシッドレッド289、アシッドローダミンG、C.I.アシッドバイオレット9がより好ましく、更に、発色性、耐熱性、耐光性に優れる点から、C.I.アシッドレッド52、C.I.アシッドレッド289を用いることが好ましい。
また、酸性染料と、オニウム塩基を有する化合物との造塩化合物であってもよく、なかでも、オニウム塩基を有する化合物が、側鎖にカチオン性基を有する樹脂であることにより、明度及び耐性に優れた着色組成物とすることが出来る。
キサンテン系酸性染料の場合、酸性染料と側鎖にカチオン性基を有する樹脂とからなる造塩化合物(a’)として用いてもよい。当該造塩化合物(a’)を得るための、側鎖にカチオン性基を有する樹脂について説明する。
造塩化合物を得るための側鎖にカチオン性基を有する樹脂としては、側鎖に少なくとも1つのオニウム塩基を有するものであれば、特に制限はないが、好適なオニウム塩構造としては、入手性等の観点からは、アンモニウム塩、ヨードニウム塩、スルホニウム塩、ジアゾニウム塩、及びホスホニウム塩であることが好ましく、保存安定性(熱安定性)を考慮すると、アンモニウム塩、ヨードニウム塩、及びスルホニウム塩であることがより好ましい。さらに好ましくはアンモニウム塩である。
酸性染料と、含窒素化合物又は側鎖にカチオン性基を有する樹脂との造塩化合物は、従来知られている方法により製造することができる。特開平11-72969号公報などに具体的な手法が開示されている。キサンテン系酸性染料を用いて一例をあげると、キサンテン系酸性染料を水に溶解した後、四級アンモニウム塩化合物を添加、攪拌しながら造塩化処理を行なえばよい。ここでキサンテン系酸性染料中のスルホン酸基(-SO3H)、スルホン酸ナトリウム基(-SO3Na)の部分と四級アンモニウム塩化合物のアンモニウム基(NH4+)の部分が結合した造塩化合物が得られる。また水の代わりに、メタノール、エタノールも造塩化時に使用可能な溶剤である。
また、その他の酸性染料においても、キサンテン系染料と同様の手法で、含窒素化合物又は側鎖にカチオン性基を有する樹脂との造塩化合物を得ることができる。
酸性染料は、スルホン酸アミド化合物と、アニオン性染料とを反応させて得られたスルホン酸アミド化合物であってもよい。
酸性染料に好ましく用いることのできる酸性染料のスルホン酸アミド化合物は、-SO3H、-SO3Naを有する酸性染料を常法によりクロル化して、-SO3Hを-SO2Clとし、この化合物を、-NH2基を有するアミンと反応して製造することができる。
また、スルホンアミド化において好ましく使用できるアミン化合物としては、具体的には、2-エチルへキシルアミン、ドデシルアミン、3-デシロキシプロピルアミン、3-(2-エチルヘキシルオキシ)プロピルアミン、3-エトキシプロピルアミン、シクロへキシルアミン等を用いることが好ましい。
また、C.I.アシッドレッド52を3-(2-エチルヘキシルオキシ)プロピルアミンを用いて変性したスルホン酸アミド化合物を得る場合も、C.I.アシッドレッド52をスルホニルクロリド化した後、ジオキサン中で理論当量の3-(2-エチルヘキシルオキシ)プロピルアミンと反応させてC.I.アシッドレッド52のスルホン酸アミド化合物を得ればよい。
光重合性単量体(B)は、少なくとも下記一般式(1)で表される化合物を含み、必要に応じてさらに他の光重合性単量体を含んでいてもよいものである。
一般式(1)
[CH2=CHC(=O)-(OCmH2m)n-OCH2]3-CR
(一般式(1)中、mは1~3の整数を表し、nは0~2の整数を表し、複数あるm及びnは同一であっても異なってもよい。
Rは-CH2CH3、-CH2OH、-CH2O(C=O)C=CH2から選ばれる置換基を表す。)
一般式(1)で表される化合物は、1種単独で、又は2種以上を組み合わせて用いることができる。
他の光重合性化合物は、1種を単独で、又は2種以上混合して用いることができる。
本有機EL表示装置において、光重合開始剤(C)は、オキシムエステル系光重合開始剤を含み、必要に応じてさらに他の光重合開始剤を含んでいてもよいものである。オキシムエステル系光重合開始剤を含有する感光性着色組成物は、紫外線照射硬化性を有し、溶剤現像性又はアルカリ現像性を有する感光性着色組成物とすることができる。そのため、当該感光性着色組成物によれば、フォトリソグラフィー法により画素を形成することができる。また、前記オキシムエステル系光重合開始剤を用いることにより、色特性及び耐薬品性に優れ、パターニング性も良好な感光性着色組成物となる。
オキシムエステル系光重合開始剤としては、中でも、下記一般式(2)~(4)で表されるオキシムエステル系光重合開始剤が挙げられ、下記一般式(2)又は(3)で表されるオキシムエステル系光重合開始剤が好ましく、一般式(2)で表されるオキシムエステル系光重合開始剤がより好ましい。
R2~R11におけるアリール基としては、フェニル基、ナフチル基、アントラセニル基などがあげられる。
なお、Zが直接結合とは、Zが原子を有さず、一般式(2)中でZと接続している2つの原子が直接結合していることを示す。
また、これらの置換基は1個以上あるいは1種以上存在することができ、さらにこれらの置換基の水素原子がさらに他の置換基で置換されていてもよい。
Raは、炭素数2~6のアルキル基であり、Rbは、炭素数4~10のアルキル基であり、Rcは、少なくとも炭化水素環又は複素環を含み、更に炭素数1~4のアルキレン鎖、チオエーテル結合(-S-)、エーテル結合(-O-)、及びカルボニル結合(-CO-)から選択される少なくとも1種の2価の連結基を含んでいてもよい基であり、RbとRcとは互いに異なる置換基である。Rd及びReはそれぞれ独立に炭素数1~6のアルキル基である。)
Rbにおけるアルキル基としては、ブチル基、ヘキシル基、オクチル基、ドデシル基などの直鎖アルキル基が挙げられる。
Rcにおける炭化水素環としては、シクロヘキシル基などの脂肪族炭化水素環、フェニル基、ナフチル基、アントラセニル基などの芳香族炭化水素環などが挙げられる。また、Rcにおける複素環としては、上記炭化水素環の炭素原子の1つ又は2つ以上が、窒素原子、酸素原子、硫黄原子に置き換わった環が挙げられる。
また、Rd及びReにおけるアルキル基は、例えば、メチル基、エチル基、プロピル基、ブチル基、ヘキシル基、等の直鎖アルキル基が挙げられる。
R21~R26におけるアリール基は、前記R2~R11におけるアリール基と同様のものとすることができる。
R26の複素環基における複素環としては、例えば、フラン、チオフェン、ピロール、オキサゾール、チアゾール、イミダゾール、ピラゾール、ピラン、ピロン、ピリジン、ピロン、ピリダジン、ピリミジン、ピラジン、ベンゾフラン、チオナフテン、インドール、カルバゾール、クマリン、キノリン、フタラジン、キノキサリン等が挙げられる。
また、アルキル基及びアリール基が有してもよい置換基は、前記一般式(2)における置換基と同様のものとすることができる。
また、光重合性開始剤(C)は、更に他の光重合性開始剤を含有してもよい。他の光重合性開始剤としては、例えば、4-フェノキシジクロロアセトフェノン、4-t-ブチル-ジクロロアセトフェノン、ジエトキシアセトフェノン、1-(4-イソプロピルフェニル)-2-ヒドロキシ-2-メチルプロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン、2-(ジメチルアミノ)-2-[(4-メチルフェニル)メチル]-1-[4-(4-モルフォリニル)フェニル]-1-ブタノン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタン-1-オン等のアセトフェノン系化合物;ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール等のベンゾイン系化合物;ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、4-フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、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(t-ブチルパーオキシカルボニル)ベンゾフェノン等のベンゾフェノン系化合物;チオキサントン、2-クロルチオキサントン、2-メチルチオキサントン、イソプロピルチオキサントン、2,4-ジ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等のチオキサントン系化合物;2,4,6-トリクロロ-s-トリアジン、2-フェニル-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(p-メトキシフェニル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(p-トリル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-ピペロニル-4,6-ビス(トリクロロメチル)-s-トリアジン、2,4-ビス(トリクロロメチル)-6-スチリル-s-トリアジン、2-(ナフト-1-イル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(4-メトキシ-ナフト-1-イル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2,4-トリクロロメチル-(ピペロニル)-6-トリアジン、2,4-トリクロロメチル-(4’-メトキシスチリル)-6-トリアジン等のトリアジン系化合物;ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイルジフェニルホスフィンオキサイド等のホスフィン系化合物;9,10-フェナンスレンキノン、カンファーキノン、エチルアントラキノン等のキノン系化合物;ボレート系化合物;カルバゾール系化合物;イミダゾール系化合物;あるいは、チタノセン系化合物等が挙げられる。
これらの光重合開始剤は、1種を単独で、又は必要に応じて任意の比率で2種以上混合して用いることができる。
光重合性開始剤の市販品としては、アセトフェノン系化合物としては、全てBASFジャパン社製で「IRGACURE 907」(2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン)、「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-モルフォリニル)フェニル]-1-ブタノン)、「IRGACURE 379」2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタン-1-オン、ホスフィン系化合物としては、全てBASFジャパン社製で「IRGACURE 819」(ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド)、「IRGACURE TPO」(2,4,6-トリメチルベンゾイルジフェニルホスフィンオキサイド)などが挙げられる。
感光性着色組成物は、さらに、増感剤を含有してもよい。
増感剤としては、カルコン誘導体、ジベンザルアセトンなどの不飽和ケトン類;ベンジルやカンファーキノンなどの1,2-ジケトン誘導体;ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノ-ル誘導体等のポリメチン色素;アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体、又はミヒラーケトン誘導体、α-アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、9,10-フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、4,4’-ジエチルイソフタロフェノン、3,3’又は4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノン、4,4’-ビス(ジエチルアミノ)ベンゾフェノン等が挙げられる。
その他、紫外から近赤外域にかけての光に対して吸収を示す増感剤を含有させることもできる。
増感剤は、1種を単独で、又は必要に応じて任意の比率で2種以上混合して用いることができる。
本感光性着色組成物は、樹脂(D)を含有する。樹脂(D)は、厚さ2μmの被膜を形成したときに400~700nmの全波長領域において透過率が80%以上となる透明樹脂が好ましく、前記透過率は95%以上が好ましい。樹脂(D)は、熱可塑性樹脂及び感光性樹脂から選択される1種以上が好ましい。また、樹脂(D)はアルカリ可溶性を有することが好ましい。これにより感光性着色組成物から形成する被膜をフォトリソグラフィー法でパターニングできる。アルカリ可溶性を有しない感光性樹脂、およびアルカリ可溶性樹脂は、熱硬化性基を有していてもよい。前記熱硬化性基は、例えば、エポキシ基、オキセタニル基等が挙げられる。
熱可塑性樹脂はアルカリ可溶性を有しないものを含んでいてもよい。アルカリ可溶性を有しない熱可塑性樹脂は、例えば、アクリル樹脂、ブチラール樹脂、スチレン-マレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル-酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、ビニル系樹脂、アルキッド樹脂、ポリスチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリエチレン(HDPE、LDPE)、ポリブタジエン、及びポリイミド樹脂等が挙げられる。
アルカリ可溶性感光性樹脂は、重合性不飽和基を有するため感光性を有する。アルカリ可溶性感光性樹脂は、アルカリ可溶性があり、感光性を有すれば良く、公知の樹脂を使用できるところ、以下の方法(i)(ii)で合成した樹脂が好ましい。アルカリ可溶性感光性樹脂は、を使用すると光照射で3次元架橋して架橋密度が上がるため、被膜の薬品耐性が向上する。
方法(i)は、例えば、まず、エポキシ基含有単量体、およびその他単量体の重合体を合成する。次いで、前記重合体のエポキシ基に、モノカルボキシル基含有単量体を付加し、生成した水酸基に、多塩基酸無水物を反応させてアルカリ可溶性感光性樹脂を得る方法が挙げられる。なお、モノカルボキシル基含有単量体は、カルボキシル基を1有する単量体である。
あるいは、(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、ダイアセトン(メタ)アクリルアミド、又はアクリロイルモルホリン等の(メタ)アクリルアミド類スチレン、又はα-メチルスチレン等のスチレン類、エチルビニルエーテル、n-プロピルビニルエーテル、イソプロピルビニルエーテル、n-ブチルビニルエーテル、又はイソブチルビニルエーテル等のビニルエーテル類、酢酸ビニル、又はプロピオン酸ビニル等の脂肪酸ビニル類等が挙げられる。
本感光性着色組成物は、着色剤(A)、光重合性単量体(B)、光重合開始剤(C)、及び樹脂(D)のほか、必要に応じて他の成分を含有してもよい。以下、感光性着色組成物に含まれ得る各成分について説明する。
感光性着色組成物は、熱硬化性化合物を含有してもよい。これによりカラーフィルタを作製する際、被膜をフォトリソグラフによりパターンを形成した後の加熱工程で架橋密度が向上するため耐熱性が向上する。また、加熱工程で着色剤(A)が凝集し難くなるため、コントラスト比がより向上する。
熱硬化性化合物は、例えば、エポキシ化合物、オキセタン化合物、ベンゾグアナミン化合物、ロジン変性マレイン酸化合物、ロジン変性フマル酸化合物、メラミン化合物、尿素化合物、およびフェノール化合物が挙げられる。これらの中でも、エポキシ化合物、オキセタン化合物が好ましい。
エポキシ化合物は、例えば、ビスフェノール類(ビスフェノールA、ビスフェノールF、ビスフェノールS、ビフェノール、ビスフェノールAD等)、フェノール類(フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等)と各種アルデヒド(ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等)との重縮合物、フェノール類と各種ジエン化合物(ジシクロペンタジエン、テルペン類、ビニルシクロヘキセン、ノルボルナジエン、ビニルノルボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等)との重合物、フェノール類とケトン類(アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等)との重縮合物、フェノール類と芳香族ジメタノール類(ベンゼンジメタノール、α,α,α’,α’-ベンゼンジメタノール、ビフェニルジメタノール、α,α,α’,α’-ビフェニルジメタノール等)との重縮合物、フェノール類と芳香族ジクロロメチル類(α,α’-ジクロロキシレン、ビスクロロメチルビフェニル等)との重縮合物、ビスフェノール類と各種アルデヒドの重縮合物、アルコール類等をグリシジル化したグリシジルエーテル系エポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキシ樹脂、脂肪族エポキシ樹脂、グリシジルアミン系エポキシ樹脂、グリシジルエステル系エポキシ樹脂等が挙げられる。
オキセタン化合物は、オキセタン基を有する化合物である。オキセタン化合物は、1官能オキセタン化合物、2官能オキセタン化合物、3官能以上のオキセタン化合物が挙げられる。
市販品は、大阪有機化学工業社製OXE-10、OXE-30、東亞合成社製OXT-101、OXT-212等が挙げられる。
市販品は、宇部興産社製OXBP、OXTP、東亞合成社製OXT-121、OXT-221等が挙げられる。
メラミン化合物は、メラミン環構造を有する化合物である。メラミン化合物は、低分子化合物や高分子量化合物が含まれる。本明細書でメラミン化合物は、メラミン環に、メチロール基またはエーテル基が結合した化合物が好ましい。メラミン環1個当たりのメチロール基および/またはエーテル基の結合数は、平均5.0以上が好ましい。適度な結合数を有すると被膜の耐溶剤性がより向上し、コントラスト比が低下し難くなる。
本感光性着色組成物は、酸化防止剤を含有してもよい。酸化防止剤は、光重合開始剤や熱硬化性化合物が、熱硬化やITOアニール時の熱工程によって酸化し黄変することを防ぐため、画素の透過率を高くすることができる。
感光性着色組成物には、基材との密着性を高めるためにシランカップリング剤等の密着向上剤を含有してもよい。密着向上剤による密着性が向上することにより、細線の再現性が良好となり解像度が向上する。
感光性着色組成物には、当該組成物のレベリング性を向上するため、レベリング剤を添加してもよい。レベリング剤としては、主鎖にポリエーテル構造又はポリエステル構造を有するジメチルシロキサンが好ましい。主鎖にポリエーテル構造を有するジメチルシロキサンの具体例としては、東レ・ダウコーニング社製FZ-2122、ビックケミー社製BYK-333などが挙げられる。ポリエステル構造を有するジメチルシロキサンの具体例としては、ビックケミー社製BYK-310、BYK-370などが挙げられる。主鎖にポリエーテル構造を有するジメチルシロキサンと、主鎖にポリエステル構造を有するジメチルシロキサンとは、併用することもできる。レベリング剤の含有割合は、着色組成物の全固形分中、0.003~0.5質量%用いることが好ましい。
レベリング剤に補助的に加えるアニオン性界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン-アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン-アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどが挙げられる。
また感光性着色組成物は、熱硬化性樹脂の硬化を補助するため、必要に応じて、硬化剤、硬化促進剤を含有してもよい。硬化剤としては、フェノール系樹脂、アミン系化合物、酸無水物、活性エステル、カルボン酸系化合物、スルホン酸系化合物などが有効であるが、特にこれらに限定されるものではなく、熱硬化性樹脂と反応し得るものであれば、いずれの硬化剤を使用してもよい。また、これらの中でも、1分子内に2個以上のフェノール性水酸基を有する化合物、アミン系硬化剤が好ましく挙げられる。上記硬化促進剤としては、例えば、アミン化合物(例えば、ジシアンジアミド、ベンジルジメチルアミン、4-(ジメチルアミノ)-N,N-ジメチルベンジルアミン、4-メトキシ-N,N-ジメチルベンジルアミン、4-メチル-N,N-ジメチルベンジルアミン等)、4級アンモニウム塩化合物(例えば、トリエチルベンジルアンモニウムクロリド等)、ブロックイソシアネート化合物(例えば、ジメチルアミン等)、イミダゾール誘導体二環式アミジン化合物及びその塩(例えば、イミダゾール、2-メチルイミダゾール、2-エチルイミダゾール、2-エチル-4-メチルイミダゾール、2-フェニルイミダゾール、4-フェニルイミダゾール、1-シアノエチル-2-フェニルイミダゾール、1-(2-シアノエチル)-2-エチル-4-メチルイミダゾール等)、リン化合物(例えば、トリフェニルホスフィン等)、グアナミン化合物(例えば、メラミン、グアナミン、アセトグアナミン、ベンゾグアナミン等)、S-トリアジン誘導体(例えば、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン、2-ビニル-2,4-ジアミノ-S-トリアジン、2-ビニル-4,6-ジアミノ-S-トリアジン・イソシアヌル酸付加物、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン・イソシアヌル酸付加物等)などを用いることができる。これらは1種単独で使用してもよく、2種以上を併用してもよい。上記硬化促進剤の含有量としては、熱硬化性樹脂100質量部に対し、0.01~15質量部が好ましい。
本感光性着色組成物は、経時粘度を安定化させるために貯蔵安定剤を含有してもよい。
貯蔵安定剤としては、例えば、ベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの4級アンモニウムクロライド、乳酸、シュウ酸などの有機酸及びそのメチルエーテル、t-ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。貯蔵安定剤は、着色剤100質量部に対し、0.1~10質量部の量で用いることができる。
感光性着色組成物は、溶剤を含有してもよい。これにより感光性着色組成物の粘度調整が容易になるため、表面が平滑な被膜を形成し易い。溶剤は、使用目的に応じて適宜選択し、適量を含有すれば良い。
水酸基を有さないエーテル溶剤は、例えば、テトラヒドロフラン、テトラヒドロピラン、1,4-ジオキサン、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、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジブチルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチル-n-プロピルエーテル、アニソール、フェネトール、メチルアニソールなどが挙げられる。
本感光性着色組成物は、これらの中でもエーテルアルコール溶剤を含むことが当該感光性着色組成物の相溶性と塗布性の観点から好ましい。
中でも、エーテルアルコール溶剤は、トリプロピ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、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、3-メトキシ-1-ブタノール、3-メトキシ-3-メチルブタノールが好ましい。
また、中でも、エーテルエステル溶剤は、プロピレングリコールモノメチルエーテルアセテート、3-エトキシプロピオン酸エチルが好ましい。
着色剤を着色剤担体中に分散する際に、適宜、色素誘導体、樹脂型分散剤、界面活性剤等の分散助剤を含有してもよい。分散助剤は、分散後の着色剤の再凝集を防止する効果が大きいので、分散助剤を用いて着色剤を着色剤担体中に分散してなる着色組成物は、明度及び粘度安定性が良好になる。
色素誘導体としては、有機顔料、アントラキノン、アクリドン又はトリアジンに、塩基性置換基、酸性置換基、又は置換基を有していても良いフタルイミドメチル基を導入した化合物があげられ、例えば、特開昭63-305173号公報、特公昭57-15620号公報、特公昭59-40172号公報、特公昭63-17102号公報、特公平5-9469号公報、特開2001-335717号公報、特開2003-128669号公報、特開2004-091497号公報、特開2007-156395号公報、特開2008-094873号公報、特開2008-094986号公報、特開2008-095007号公報、特開2008-195916号公報、特許第4585781号公報等に記載されているものを使用でき、これらは単独又は2種類以上を混合して用いることができる。
樹脂型分散剤は、着色剤に吸着する性質を有する着色剤親和性部位と、着色剤担体と相溶性のある部位とを有し、着色剤に吸着して着色剤の着色剤担体への分散を安定化する働きをするものである。樹脂型分散剤として具体的には、ポリウレタン、ポリアクリレート等のポリカルボン酸エステル、不飽和ポリアミド、ポリカルボン酸、ポリカルボン酸(部分)アミン塩、ポリカルボン酸アンモニウム塩、ポリカルボン酸アルキルアミン塩、ポリシロキサン、長鎖ポリアミノアマイドリン酸塩、水酸基含有ポリカルボン酸エステルや、これらの変性物、ポリ(低級アルキレンイミン)と遊離のカルボキシル基を有するポリエステルとの反応により形成されたアミドやその塩等の油性分散剤、(メタ)アクリル酸-スチレン共重合体、(メタ)アクリル酸-(メタ)アクリル酸エステル共重合体、スチレン-マレイン酸共重合体、ポリビニルアルコール、ポリビニルピロリドン等の水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート系、エチレンオキサイド/プロピレンオキサイド付加化合物、燐酸エステル系等が用いられ、これらは単独で又は2種以上を混合して用いることができるが、必ずしもこれらに限定されるものではない。
界面活性剤としては、ラウリル硫酸ナトリウム、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン-アクリル酸共重合体のアルカリ塩、ステアリン酸ナトリウム、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、スチレン-アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステル等のアニオン性界面活性剤;ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレート等のノニオン性界面活性剤;アルキル4級アンモニウム塩やそれらのエチレンオキサイド付加物等のカオチン性界面活性剤;アルキルジメチルアミノ酢酸ベタイン等のアルキルベタイン、アルキルイミダゾリン等の両性界面活性剤が挙げられ、これらは単独で又は2種以上を混合して用いることができるが、必ずしもこれらに限定されるものではない。
感光性着色組成物の製造方法は、例えば、まず、着色剤分散体を調製し、次いで、光重合性単量体と、光重合開始剤と、必要に応じて用いられる他の成分とを添加する方法などが挙げられる。
着色剤分散体は、例えば、着色剤を、バインダー樹脂などの着色剤担体及び/又は有機溶剤中に、好ましくは分散助剤と一緒に、ニーダー、2本ロールミル、3本ロールミル、ボールミル、横型サンドミル、縦型サンドミル、アニュラー型ビーズミル、又はアトライター等の各種分散手段を用いて微細に分散することで調製できる。着色剤(A)が2種以上の着色剤を含む場合、複数ある着色剤を同時に着色剤担体に分散しても良いし、別々に着色剤分散液を調製した後に混合してもよい。また、着色剤の溶解性が高い場合、具体的には使用する有機溶剤への溶解性が高く、攪拌により溶解、異物が確認されない状態であれば、上記のような微細に分散して製造する必要はない。
本感光性着色組成物は、遠心分離、焼結フィルタやメンブレンフィルタによる濾過等の手段にて、5μm以上の粗大粒子、好ましくは1μm以上の粗大粒子、さらに好ましくは0.5μm以上、特に好ましくは0.3μm以上の粗大粒子及び混入した塵の除去を行うことが好ましい。
次に有機EL表示装置の構成について図1を参照して説明する。図1は、本有機EL表示装置の、模式的な断面図である。本有機EL表示装置10は、駆動素子が形成されたシリコン基板1上に、有機EL層2と、カラーフィルタとを有するものであり、必要に応じて、当該カラーフィルタ3上に、さらに封止層4やカバーガラス5を有してもよく、また、有機EL層2とカラーフィルタ3との間に平坦層(プレーナー)を有してもよい(図示せず)。
以下、有機EL表示装置の各構成の詳細について説明する。
カラーフィルタ3は、有機EL層上に形成され、少なくとも赤色画素と、緑色画素と、青色画素とを備えている(3a、3b、3c)。当該画素が前述の感光性着色組成物の硬化物である。カラーフィルタは、さらにマゼンタ色画素、シアン色画素、黄色画素、又はその他の画素を有するものであってもよい。
カラーフィルタは、有機EL層2上に、又は、必要に応じて設けられた平坦層上に形成される。平坦層を設けることにより有機EL層の微細な凹凸面を平坦化することができる。
平坦層は、公知の硬化性樹脂を用いることができ、紫外線硬化型樹脂が好ましく、必要に応じては熱硬化型樹脂を併用してもよい。前記紫外線硬化型樹脂としては特に限定するものではないが、i線(波長365nm)に感度を示すアクリル系樹脂が好ましい。
まず、前述した感光性着色組成物を、スプレーコート法、ディップコート法、バーコート法、コールコート法、スピンコート法などの塗布手段を用いて有機EL層又は平坦層に塗布して、塗膜を形成する。
次いで、必要に応じて前記塗膜を乾燥させたのち、これに、所定のパターンのマスクを介して露光し、光重合性単量体や感光性樹脂を光重合反応させて、硬化塗膜とする。露光に使用される光源としては、例えば低圧水銀灯、高圧水銀灯、メタルハライドランプなどの紫外線、電子線等が挙げられる。露光量は、使用する光源や塗膜の厚みなどによって適宜調整すればよい。
また、露光後に重合反応を促進させるために、加熱処理を行ってもよい。前記感光性着色組成物は、低温硬化性を有するため、100℃以下の加熱処理であっても十分に硬化することができる。
また、カラーフィルタを構成する赤色画素、緑色画素、青色画素は、以下の分光特性を有することにより、高輝度かつ高色再現性を有し、高品位な有機EL表示装置とすることができる。
赤色画素:波長450nm~560nmの範囲における光の最大透過率が0.5%以下、かつ波長600nm~700nmの範囲の光の最大透過率が80%以上100%未満。
緑色画素:波長400nm~470nmの範囲における光の最大透過率が2%以下、波長525~535nmの光の最大透過率が67%以上、短波長側50%半値波長が497~507nm、かつ長波長側50%半値波長が554~581nm。
青色画素:波長500nm~560nmの範囲における光の最大透過率が20%未満。
カラーフィルタは各画素が、上記の分光特性を有することで、色域の広いカラーフィルタとなる。
前記有機EL層は、発光物質を含む有機発光単層、あるいは多層で形成することができる。多層で形成される場合は、たとえば一般的な正孔輸送層、電子輸送性有機発光層、電子輸送層が順次積層してなる3層構成、さらには正孔(電子)注入層、正孔(電子)輸送層と注入機能と輸送機能を分けた層を設けたり、あるいは正孔(電子)輸送をブロックする層を設けたりする多層構成でもよい。
(微細化赤色顔料(PR177-1))
ジアントラキノン系顔料C.I.PigmentRed177(「CinilexRedSR3C」CINICChemicals社製)150部、塩化ナトリウム1500部、及びジエチレングリコール250部を、ステンレス製1ガロンニーダー(井上製作所製)中に仕込み、60℃で10時間混練した。次に、混練した混合物を温水に投入し、約70℃に加熱しながら1時間攪拌してスラリー状として、濾過及び水洗をして食塩及びジエチレングリコールを除いた後、80℃で一昼夜乾燥させ、粉砕することにより、138部のアントラキノン系の微細顔料(PR177-1)を得た。
ジケトピロロピロール系赤色顔料C.I.ピグメントレッド254(BASF社製「Irgajin RedL 3630」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、ジケトピロロピロール系の微細化赤色顔料(PR254-1)を得た。
黄色顔料C.I.ピグメントイエロー139(BASFジャパン社製「パリオトールエローD1819」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、微細化黄色顔料(PY139-1)を得た。
黄色着色剤として、C.I.ピグメントイエロー185(BASF社「Paliotol Yellow L 1155」)200部、塩化ナトリウム1000部、及びジエチレングリコール100部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、100℃で6時間混練した。次にこの混練物を5リットルの温水に投入し、70℃に加熱しながら1時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥し、微細化黄色顔料(PY185-1)を得た。
黄色着色剤として、C.I.ピグメントイエロー185(BASF社「Paliotol Yellow L 1155」)95部、ロジンマレイン酸樹脂(荒川化学工業社製「マルキード32」)10部、塩化ナトリウム1200部、およびジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、60℃で8時間混連した。次に、この混練物を温水8000部に投入し、約70℃に加熱しながら1時間撹拌してスラリー状として、濾過、水洗を繰り返して塩化ナトリウムおよびジエチレングリコールを除いた後、80℃で一昼夜乾燥し、黄色微細化顔料(PY185-2)105部を得た。
フタロシアニン顔料C.I.ピグメントグリーン36(トーヨーカラー社製「リオノールグリーン6YK」)120部、塩化ナトリウム1600部、およびジエチレングリコール270部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、70℃で12時間混練した。この混合物を温水5000部に投入し、約70℃に加熱しながら1時間撹拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で一昼夜乾燥し、117部の微細化顔料(PG36-1)を得た。
フタロシアニン系緑色顔料C.I.ピグメントグリーン58(DIC株式会社製「FASTOGEN GREEN A110」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、フタロシアニン系の微細化緑色顔料(PG58-1)を得た。
フタロシアニン系緑色顔料C.I.ピグメントグリーン62(トーヨーカラー社製)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、フタロシアニン系の微細化緑色顔料(PG62-1)を得た。
フタロシアニン系緑色顔料C.I.ピグメントグリーン63(トーヨーカラー社製)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、フタロシアニン系の微細化緑色顔料(PG63-1)を得た。
C.I.ピグメントグリーン59 100部、塩化ナトリウム1,200部、およびジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、70℃で6時間混練した。この混練物を3,000部の温水に投入し、70℃に加熱しながら1時間撹拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウムおよびジエチレングリコールを除いた後、80℃で一昼夜乾燥し、微細化した顔料(PG59-1)を得た。
フタロシアニン系青色顔料C.I.ピグメントブルー15:6(トーヨーカラー株式会社製「LIONOL BLUE ES」、比表面積60m2/g)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、フタロシアニン系の微細化青色顔料(PB15:6-1)を得た。
フタロシアニン系青色顔料(C.I.ピグメントブルー15:3、トーヨーカラー株式会社製「LIONOL BLUE FG-7351」)200部、塩化ナトリウム600部、およびジエチレングリコール600部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、120℃で8時間混練した。次に、この混練物を5リットルの温水に投入し、70℃に加熱しながら1時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥し、フタロシアニン系の微細化青色顔料(PB15:3-1)を得た。
ジオキサジン系紫色顔料C.I.ピグメントバイオレット23(トーヨーカラー株式会社製「LIONOGEN VIOLET RL」)200部、塩化ナトリウム1400部、及びジエチレングリコール360部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。次にこの混練物を8000部の温水に投入し、80℃に加熱しながら2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、ジオキサジン系の微細化紫色顔料(PV23-1)を得た。
下記の手順でC.I.アシッドレッド289と4級アンモニウム塩化合物であるトリステアリルモノメチルアンモニウムクロライドとからなる造塩化合物(V)を作製した。5%水溶液になるよう、C.I.アシッドレッド289の10部を200部の水に溶解させ、30~50℃に加熱した後、メタノール/水=20/80溶液に5%溶液になるよう5.5部のトリステアリルモノメチルアンモニウムクロライドを溶解し、少しずつ滴下した。トリステアリルモノメチルアンモニウムクロライド溶液を滴下した後、30~50℃で3時間攪拌した。攪拌しながら室温まで放冷した後、吸引濾過を行い、水洗後、濾紙上に残った造塩化合物を乾燥機にて水分を除去して乾燥して、C.I.アシッドレッド289とトリステアリルモノメチルアンモニウムクロライドとの造塩化合物(V)8部を得た。
(樹脂型分散剤溶液1):感光性樹脂
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、3-メルカプト-1,2-プロパンジオール8部、ピロメリット酸無水物12部、プロピレングリコールモノメチルエーテルアセテート(PGMAc)80部、触媒としてモノブチルスズオキシド0.2部を仕込み、窒素ガスで置換した後、120℃で5時間反応させた(第一工程)。酸価の測定で95%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。次に、メチルメタクリレート(MMA)15部、t-ブチルアクリレート(tBA)10部、エチルアクリレート(EA)10部、メタクリル酸(MAA)5部、ベンジルメタクリレート(BzMA)10部、2-ヒドロキシエチルメタクリレート(HEMA)50部を仕込み、反応容器内を80℃に加熱して、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1部を添加し、12時間反応した(第二工程)。固形分測定により95%が反応したことを確認した。次いで、次にフラスコ内を空気置換し、2-メタクリロイルオキシエチルイソシアネート(MOI)54.0部、ヒドロキノン0.1部を仕込み、70℃で4時間反応を行った(第三工程)。IRにてイソシアネート基に基づく2270cm-1のピークの消失を確認後、反応溶液を冷却して、PGMAcで固形分調整することにより、固形分40%の感光性樹脂である樹脂型分散剤溶液1を得た。得られた樹脂型分散剤の酸価は36、重量平均分子量は12,000であった。
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、エチルアクリレート30部、tert-ブチルアクリレート20部、2‐メチルメタクリレート40部、を仕込み、窒素ガスで置換した。反応容器内を80℃に加熱して、3-メルカプト-1,2-プロパンジオール6部に、2,2’-アゾビスイソブチロニトリル0.1部をシクロヘキサノン45.7部に溶解した溶液を添加して、10時間反応した。固形分測定により95%が反応したことを確認した。このとき、重量平均分子量が4000であった。次に、ピロメリット酸二無水物9.7部、PGMAc70部、触媒として1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン0.20部を追加し、120℃で7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反応を終了した。反応終了後、不揮発分を40重量%に調製し、重量平均分子量8,100、酸価50mgKOH/g、ビニル重合部位のガラス転移温度22.5℃の樹脂型分散剤のPGMAc溶液(樹脂型分散剤溶液2)を得た。
(アクリル樹脂溶液(D-1)):感光性樹脂
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けた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100部を入れ、容器に窒素ガスを注入しながら120℃に加熱して、同温度で滴下管よりスチレン5.2部、グリシジルメタクリレート35.5部、ジシクロペンタニルメタクリレート41.0部、アゾビスイソブチロニトリル1.0部の混合物を2.5時間かけて滴下し重合反応を行った。次にフラスコ内を空気置換し、アクリル酸17.0部にトリスジメチルアミノメチルフェノール0.3部、及びハイドロキノン0.3部を投入し、120℃で5時間反応を続け固形分酸価=0.8となったところで反応を終了し、重量平均分子量が約12,000(GPCによる測定)の樹脂溶液を得た。
更にテトラヒドロ無水フタル酸30.4部、トリエチルアミン0.5部を加え120℃で4時間反応させ、不揮発分が20%になるよう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を添加してアクリル樹脂溶液(D-1)を調製した。
撹拌機、温度計、還流冷却管、滴下ロート及び窒素導入管を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート182gを導入し、フラスコ内雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5g(0.40モル)、メタクリル酸43.0g(0.5モル)、トリシクロデカン骨格のモノメタクリレート(日立化成(株)製FA-513M)22.0g(0.10モル)及びプロピレングリコールモノメチルエーテルアセテート136gからなる混合物にアゾビスイソブチロニトリル3.6gを添加した溶液を滴下ロートから2時間かけてフラスコに滴下し、さらに100℃で5時間撹拌し続けた。次に、フラスコ内雰囲気を窒素から空気にし、グリシジルメタクリレート35.5g[0.25モル、(本反応に用いたメタクリル酸のカルボキシル基に対して50モル%)]、トリスジメチルアミノメチルフェノール0.9g及びハイドロキノン0.145gをフラスコ内に投入し、110℃で6時間反応を続け、不揮発分が20%になるよう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を添加して固形分酸価が79mgKOH/gのアクリル樹脂溶液(D-2)を得た。GPCにより測定したポリスチレン換算の重量平均分子量は13,000で、分子量分布(Mw/Mn)は2.1であった。
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、滴下管及び撹拌装置を取り付けた反応容器にシクロヘキサノン196部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管より、ベンジルメタクリレート20.0部、n-ブチルメタクリレート17.2部、2-ヒドロキシエチルメタクリレート12.9部、メタクリル酸12.0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(東亞合成株式会社製「アロニックスM110」)20.7部、2,2’-アゾビスイソブチロニトリル1.1部の混合物を2時間かけて滴下した。滴下終了後、更に3時間反応を継続し、アクリル樹脂の溶液を得た。
室温まで冷却した後、樹脂溶液約2部をサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が20質量%になるよう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を添加して、アクリル樹脂溶液(D-3)を調製した。重量平均分子量(Mw)は26,000であった。
(顔料分散体(PR-1))
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PR-1)を作製した。
微細化赤色顔料(PR177-1) :14.8部
樹脂型分散剤溶液1(感光性樹脂) :13.0部
プロピレングリコールモノメチルエーテルアセテート :72.2部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PR-2)を作製した。
微細化赤色顔料(PR254-1) :14.8部
樹脂型分散剤溶液1(感光性樹脂) :13.0部
プロピレングリコールモノメチルエーテルアセテート :72.2部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PY-1)を作製した。
微細化黄色顔料(PY139-1) :14.0部
樹脂型分散剤溶液2(非感光性) :15.0部
プロピレングリコールモノメチルエーテルアセテート :71.0部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PY-2)を作製した。
微細化黄色顔料(PY185-1) :12.0部
樹脂型分散剤溶液1(感光性樹脂) :20.0部
プロピレングリコールモノメチルエーテルアセテート :68.0部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PY-3)を作製した。
微細化黄色顔料(PY185-2) :12.0部
樹脂型分散剤溶液1(感光性樹脂) :20.0部
プロピレングリコールモノメチルエーテルアセテート :68.0部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PY-4)を作製した。
微細化黄色顔料(PY185-1) :12.0部
樹脂型分散剤溶液2(非感光性) :20.0部
プロピレングリコールモノメチルエーテルアセテート :68.0部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PG-1)を作製した。
微細化緑色顔料(PG36-1) :15.0部
樹脂型分散剤溶液2(非感光性) :12.5部
プロピレングリコールモノメチルエーテルアセテート :72.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PG-2)を作製した。
微細化緑色顔料(PG58-1) :15.0部
樹脂型分散剤溶液2(非感光性) :12.5部
プロピレングリコールモノメチルエーテルアセテート :72.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PG-3)を作製した。
微細化緑色顔料(PG62-1) :15.0部
樹脂型分散剤溶液2(非感光性) :12.5部
プロピレングリコールモノメチルエーテルアセテート :72.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PG-4)を作製した。
微細化緑色顔料(PG63-1) :15.0部
樹脂型分散剤溶液2(非感光性) :12.5部
プロピレングリコールモノメチルエーテルアセテート :72.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PG-5)を作製した。
微細化緑色顔料(PG59-1) :15.0部
樹脂型分散剤溶液2(非感光性) :12.5部
プロピレングリコールモノメチルエーテルアセテート :72.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が20重量%の顔料分散体(PB-1)を作製した。
微細化青色顔料(PB15:3-1) :13.0部
樹脂型分散剤溶液2(非感光性) :17.5部
プロピレングリコールモノメチルエーテルアセテート :69.5部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が17重量%の顔料分散体(PB-2)を作製した。
微細化青色顔料(PB15:6-1) :11.9部
樹脂型分散剤溶液1(感光性樹脂) :12.8部
プロピレングリコールモノメチルエーテルアセテート :75.4部
下記の混合物を均一になるように攪拌混合した後、直径0.5mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKII」)で3時間分散した後、5.0μmのフィルタで濾過し、不揮発成分が17重量%の顔料分散体(PV-1)を作製した。
微細化紫色顔料(PV23-1) :12.0部
樹脂型分散剤溶液1(感光性樹脂) :15.0部
プロピレングリコールモノメチルエーテルアセテート :73.0部
下記の混合物を均一になるように攪拌混合した後、5.0μmのフィルタで濾過し造塩化合物含有溶液(SV)を作製した。
造塩化合物(V) :13.00部
シクロヘキサノン :87.00部
[製造例1]
(感光性着色組成物(R-1))
下記の混合物を均一になるように攪拌混合した後、1.0μmのフィルタで濾過して、
感光性着色組成物(R-1)を得た。
顔料分散体(PR-1) :52.70部
顔料分散体(PR-2) :17.57部
顔料分散体(PY-1) :18.57部
光重合性単量体(B-1) :2.12部
光重合開始剤(C-1) :0.10部
レベリング剤(不揮発分1%) :1.00部
溶剤(S-1) :7.94部
(感光性着色組成物(R-2~69)の調製)
顔料分散体、光重合性単量体、光重合開始剤、及び樹脂溶液の種類と配合量を表1~7に示す内容に変更した以外は感光性着色組成物(R-1)と同様にして感光性着色組成物(R-2~69)を得た。
<光重合性単量体(B)>
光重合性単量体B-1:トリメチロールプロパンEO変性トリアクリレート(東亞合成社製「アロニックスM-350」)
光重合性単量体B-2:トリメチロールプロパントリアクリレート(東亞合成社製「アロニックスM-309」)
光重合性単量体B-3:ペンタエリスリトールトリおよびテトラアクリレート(東亞合成社製「アロニックスM-306」)
光重合性単量体B-4:ジペンタエリスリトールヘキサアクリレート(東亞合成社製「アロニックスM-402」)
<光重合開始剤(C)>
<レベリング剤>
レベリング剤:東レ・ダウコーニング社製「FZ-2122」1部をプロピレングリコールモノメチルエーテルアセテート(PGMAc)99部に溶解させた溶液
<溶剤(S)>
溶剤S-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
溶剤S-2:トリプロピレングリコールモノメチルエーテル
溶剤S-3:3-メトキシー1-ブタノール
シリコン基板にスパッタ法やエッチング法等の公知の方法を用いてTFT層を形成した。更に、TFT層上に蒸着法等の公知の方法を用いて白色有機EL素子を形成後、CVD法により窒化珪素を被覆して有機EL素子基板を形成した。
前記OLED素子上に、緑色感光性着色組成物を硬化仕上がりの膜厚が1.5μmになるようにスピンナーで塗布し、パターンマスクを介して紫外線露光、アルカリ現像、水洗及び乾燥工程を経てカラーフィルタの緑色層(G)を形成した。その後、加熱オーブンを用いて80℃、10分間加熱して硬化して、カラーフィルタの緑色層(G)の形成を完了した。
各感光性着色組成物を直径200mmのシリコンウエハ基板上に、スピンコーターを用いて乾燥後の厚さが1.50μmとなるように塗布し、70℃1分乾燥して基板を得た。次に、i線ステッパー露光装置FPA-3000i5+(Canon社製)を使用して、365nmの波長で3000J/m2の露光を行った。露光は、2.40μm四方の正方形の開口部を有するフォトマスクを通して行った。露光後の被膜をTMAH2.38%(多摩化学工業製 テトラメチルアンモニウムヒドロキシドの2.38%水溶液)で1分、パドル現像を行った。パドル現像後、20秒スピンシャワーにて純水でリンスを行い、スピン乾燥させた。開口部により形成された画素の直線性を走査型電子顕微鏡(日立ハイテク社製「S-3000N」)を用いて観察し、下記基準で評価した。
○:画素の直線性が全面で良好(実用上好ましいレベル)
△:画素の直線性が部分的に良好(実用可能なレベル)
×:画素の直線性が全面で不良(実用には適さないレベル)
各感光性着色組成物を直径200mmのシリコンウエハ基板上に、スピンコーターを用いて乾燥後の厚さが1.50μmとなるように塗布し、70℃1分乾燥して基板を得た。次に、i線ステッパー露光装置FPA-3000i5+(Canon社製)を使用して、365nmの波長で3000J/m2の露光を行った。露光は、2.40μm四方の正方形の開口部を有するフォトマスクを通して行った。露光後の被膜をTMAH2.38%(多摩化学工業製 テトラメチルアンモニウムヒドロキシドの2.38%水溶液)で1分、パドル現像を行った。パドル現像後、20秒スピンシャワーにて純水でリンスを行い、スピン乾燥させた。非露光部の現像残渣を走査型電子顕微鏡(日立ハイテク社製「S-3000N」)を用いて観察し、下記基準で評価した。
○:非露光部に現像残渣がない(実用上好ましいレベル)
△:非露光部の一部に現像残渣が存在(実用可能なレベル)
×:非露光部の全面に現像残渣が存在(実用には適さないレベル)
各感光性着色組成物を縦100mm×横100mm・0.7mm厚のガラス基板上に、スピンコーターを用いて乾燥膜厚が1.50μmとなるように回転塗工し、70℃で1分乾燥した。次に、得られた被膜に対して、400μm四方の正方パターンマスクパターンを配列したフォトマスクを介してi線の照度30mW/cm2の超高圧水銀灯にて3000mJ/cm2の露光を行った。
パターン露光された被膜に対して、TMAH2.38%を用いて、未露光部を現像した後、純水にて水洗を行なった。その後、水滴を高圧のエアーで飛ばし、基板を自然乾燥させ、80℃で10分間、ホットプレートでポストベーク処理し、ガラス基板上に硬化膜のパターンを形成した。得られた塗膜のC光源での色度([L*(1)、a*(1)、b*(1)])を顕微分光光度計(オリンパス光学社製「OSP-SP100」)を用いて測定した。続いて、その基板上に紫外線カットフィルター(ホヤ社製「COLORED OPTICAL GLASS L38」)を貼り、470W/m2のキセノンランプを用いて紫外線を100時間照射した後、C光源での色度([L*(2)、a*(2)、b*(2)])を測定し、上記計算式により、色差ΔEab*を求め、下記の4段階で評価した。
ΔEab*=((L*(2)-L*(1))2+(a*(2)-a*(1))2+(b*(2)-b*(1))2)1/2
○:ΔEab*が3.0未満(実用上好ましいレベル)
△:ΔEab*が3.0以上、6.0未満(実用可能なレベル)
×:ΔEab*が6.0以上(実用には適さないレベル)
外観観察は、NIKON製光学顕微鏡「ECLIPSELV100」にて反射観察した。画素の染込み、表面あれがないものは〇、軽微な染込みがみられるものは△、表面あれ隣接画素からの色の染込みがみられるものは×として評価した。表面あれ、隣接画素からの色の染込みがみられるものは実用的ではないと判断した。
また、画素の重なりの評価として、赤色・緑色・青色の画素の重なり量が0.1μm未満の場合を○、画素の重なり量が0.1μm以上0.3μm未満の場合を△、0.3μm以上の場合を×として評価した。画素の重なり量が0.3μm以上の場合、表示エリアが小さくなる為、有機EL表示装置の輝度低下を招いてしまうため、実用的ではないと判断した。
実施例1~37及び比較例1~5の有機EL表示装置における赤色表示時、緑色表示時、青色表示時の色度をオリンパス社製「分光放射輝度計CS-1000」を用いて測定した。得られた赤色・緑色・青色の色度からNTSC面積比率(NTSC規格で規定する色域に対する実施例又は比較例の有機EL表示装置の色域の割合)を算出した。なお、NTSCによる色度で色再現性が評価できる。
NTSC面積比率が93%以上のものは◎、90%以上のものは〇、85%以上90%未満のものは△、85%未満のものは×として評価した。NTSC面積比率が85%未満のものは、有機EL表示装置として画像表示した際に画像の鮮明さが不足して見えてしまうため、実用的ではないと判断した。
赤色、緑色、青色の3色の画素を全て点灯表示し、白色表示した際の輝度(W-L)が330cd/m2以上のものは◎、300cd/m2以上330cd/m2未満のものは〇、280cd/m2以上300cd/m2未満のものは△、280cd/m2未満のものは× として評価した。輝度が280cd/m2未満の場合は、画像表示した際に暗く見えてしまうため有機EL表示装置として実用的ではないと判断した。
各感光性着色組成物を直径200mmのシリコンウエハ基板上に、スピンコーターを用いて乾燥後の厚さが1.50μmとなるように塗布し、70℃1分乾燥して基板を得た。次に、i線ステッパー露光装置FPA-3000i5+(Canon社製)を使用して、365nmの波長で3000J/m2の露光を行った。露光は、2.40μm四方の正方形の開口部を有するフォトマスクを通して行った。露光後の被膜をTMAH2.38%(多摩化学工業製 テトラメチルアンモニウムヒドロキシドの2.38%水溶液)で1分、パドル現像を行った。パドル現像後、20秒スピンシャワーにて純水でリンスを行い、スピン乾燥させた。スピン乾燥後、ホットプレートで90℃5分間焼成し、単色のパターン基板を得た。2色目、3色目の入色も同様に行い、RGB3色入色されたパターン基板を得た。画素表面を、走査型電子顕微鏡(日立ハイテク社製「S-3000N」)を用いて観察し、下記基準で評価した。
○:画素上にヒビ割れがない(実用上好ましいレベル)
△:ヒビ割れがある画素が部分的に存在する(実用可能なレベル)
×:ヒビ割れがある画素が全体的に存在する(実用には適さないレベル)
2 有機EL層
3 カラーフィルタ
4 封止層
5 カバーガラス
10 有機EL表示装置
3a、3b、3c 画素
Claims (8)
- 駆動素子が形成されたシリコン基板上に、有機EL層と、カラーフィルタと、を有する、有機EL表示装置であって、
前記カラーフィルタが、赤色画素と、緑色画素と、青色画素とを含む画素を有し、
前記画素の膜厚が1.5μmのときの、
前記赤色画素の分光透過率が、波長450nm~560nmの範囲における光の最大透過率が0.5%以下、50%半値波長が593nm~603nm、かつ波長600nm~700nmの範囲の光の最大透過率が80%以上100%未満であり、
前記緑色画素の分光透過率が、波長400nm~470nmの範囲における光の最大透過率が2%以下、波長525~535nmの光の最大透過率が67%以上、短波長側50%半値波長が497~507nm、かつ長波長側50%半値波長が554~581nmであり、
前記青色画素の分光透過率が、波長500nm~560nmの範囲における光の最大透過率が20%未満であり、
前記画素が、着色剤(A)と、光重合性単量体(B)と、光重合開始剤(C)と、樹脂(D)とを含有する感光性着色組成物の硬化物であり、
前記赤色画素は、着色剤(A)がピグメントレッド177およびその他着色剤を含み、
前記緑色画素は、着色剤(A)がピグメントイエロー185、ならびに、ピグメントグリーン36、ピグメントグリーン62、ピグメントグリーン63およびピグメントグリーン59からなる群より選択される1種以上を含み、その他着色剤を含んでいてもよく、かつ緑色画素の着色剤(A)中、ピグメントイエロー185の含有量が49重量%~59重量%であり、
前記青色画素が、ピグメントブルー15:6およびその他着色剤を含み、
赤色画素において、前記その他着色剤が、ピグメントレッド254、およびピグメントイエロー139からなる群より選択される1種以上を含み、
緑色画素において、前記その他着色剤が、ピグメントブルー15:3を含み、
青色画素において、前記その他着色剤が、ピグメントバイオレット23、およびキサンテン系染料からなる群より選択される1種以上を含み、
前記光重合性単量体(B)が下記一般式(1)で表される化合物を含み、
光重合開始剤(C)がオキシムエステル系光重合開始剤を含む、有機EL表示装置。
一般式(1)
[CH2=CHC(=O)-(OCmH2m)n-OCH2]3-CR
(一般式(1)中、mは1~3の整数を表し、nは0~2の整数を表し、複数あるm及びnは同一であっても異なってもよい。
Rは-CH2CH3、-CH2OH、-CH2O(C=O)C=CH2から選ばれる置換基を表す。) - 前記赤色画素を構成する硬化物が、着色剤(A-1)ピグメントレッド177、着色剤(A-2)ピグメントレッド254、および着色剤(A-3)ピグメントイエロー139を含有し、
前記赤色画素における着色剤(A)中、
着色剤(A-1)の含有量が55重量%~65重量%、
着色剤(A-2)の含有量が15重量%~25重量%、
および着色剤(A-3)の含有量が15重量%~25重量%であり、
前記緑色画素を構成する硬化物が、着色剤(A-4)ピグメントイエロー185、着色剤(A-5)ピグメントグリーン36、着色剤(A-6)ピグメントグリーン62、着色剤(A-11)ピグメントグリーン63、着色剤(A-12)ピグメントグリーン59、及び着色剤(A-7)ピグメントブルー15:3を下記(I)~(IV)の組み合わせで含有し、
(I)着色剤(A-4)、着色剤(A-5)および着色剤(A-7)
(II)着色剤(A-4)および着色剤(A-6)
(III)着色剤(A-4)および着色剤(A-11)
(IV)着色剤(A-4)および着色剤(A-12)
前記緑色画素における着色剤(A)中、
着色剤(A-4)の含有量が49重量%~59重量%、
着色剤(A-5)、着色剤(A-6)、着色剤(A-11)または着色剤(A-12)の含有量が33重量%~51重量%、
および着色剤(A-7)の含有量が0重量%~13重量%であり、
前記青色画素を構成する硬化物が、着色剤(A-8)ピグメントブルー15:6、着色剤(A-9)ピグメントバイオレット23、および着色剤(A-10)キサンテン系染料を含有し、
前記青色画素における着色剤(A)中、
着色剤(A-8)の含有量が58重量%~64重量%、
着色剤(A-9)の含有量が12重量%~20重量%、
および着色剤(A-10)の含有量が17重量%~25重量%である、
請求項1に記載の有機EL表示装置。 - 前記一般式(1)で表される化合物の含有量が、光重合性単量体(B)全量に対して50重量%以上である、請求項1または2に記載の有機EL表示装置。
- 前記オキシムエステル系光重合開始剤が、下記一般式(3)で表される化合物である、請求項1~3いずれか1項に記載の有機EL表示装置。
Raは、炭素数2~6のアルキル基であり、Rbは、炭素数4~10のアルキル基であり、Rcは、少なくとも炭化水素環又は複素環を含み、更に炭素数1~4のアルキレン鎖、チオエーテル結合(-S-)、エーテル結合(-O-)、及びカルボニル結合(-CO-)から選択される少なくとも1種の2価の連結基を含んでいても良い基であり、RbとRcとは互いに異なる置換基である。Rd及びReはそれぞれ独立に炭素数1~6のアルキル基である。) - 前記樹脂(D)が、感光性樹脂を含む、請求項1~5いずれか1項に記載の有機EL表示装置。
- 前記感光性樹脂が、末端に芳香族カルボン酸を有するビニル重合体を含む、請求項6に記載の有機EL表示装置。
- 前記感光性着色組成物が、更に溶剤を含有し、前記溶剤がエーテルエステル溶剤と、エーテルアルコール溶剤とを含む、請求項1~7のいずれか一項に記載の有機EL表示装置。
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