JPH05281414A - Pigment composition for color filter - Google Patents
Pigment composition for color filterInfo
- Publication number
- JPH05281414A JPH05281414A JP10247792A JP10247792A JPH05281414A JP H05281414 A JPH05281414 A JP H05281414A JP 10247792 A JP10247792 A JP 10247792A JP 10247792 A JP10247792 A JP 10247792A JP H05281414 A JPH05281414 A JP H05281414A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- color filter
- composition
- filter according
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 190
- 239000000203 mixture Substances 0.000 title claims description 67
- 229920005989 resin Polymers 0.000 claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 26
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 239000006104 solid solution Substances 0.000 claims description 32
- 239000001052 yellow pigment Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 13
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical group C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 10
- LPDSNGAFAJYVKH-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-dichloroaniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C(Cl)=C1Cl LPDSNGAFAJYVKH-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 239000012860 organic pigment Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229920000620 organic polymer Polymers 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229920005596 polymer binder Polymers 0.000 claims description 4
- 239000002491 polymer binding agent Substances 0.000 claims description 4
- MBSOHMUBMHZCGE-UHFFFAOYSA-N 9h-carbazole;dioxazine Chemical group O1ON=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 MBSOHMUBMHZCGE-UHFFFAOYSA-N 0.000 claims description 3
- 239000001057 purple pigment Substances 0.000 claims description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical group C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 abstract description 27
- 229920000647 polyepoxide Polymers 0.000 abstract description 27
- 239000006185 dispersion Substances 0.000 abstract description 18
- 238000002834 transmittance Methods 0.000 abstract description 11
- 230000003595 spectral effect Effects 0.000 abstract description 8
- 239000004640 Melamine resin Substances 0.000 abstract description 5
- 229920000877 Melamine resin Polymers 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 5
- 229920000178 Acrylic resin Polymers 0.000 abstract description 2
- 239000004925 Acrylic resin Substances 0.000 abstract description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 abstract description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract description 2
- 150000004056 anthraquinones Chemical class 0.000 abstract description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 abstract description 2
- 229920005575 poly(amic acid) Polymers 0.000 abstract description 2
- 229920001225 polyester resin Polymers 0.000 abstract description 2
- 239000004645 polyester resin Substances 0.000 abstract description 2
- 229920001721 polyimide Polymers 0.000 abstract description 2
- 239000009719 polyimide resin Substances 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract description 2
- 230000000284 resting effect Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 14
- -1 glycidyl ester Chemical class 0.000 description 10
- 230000028161 membrane depolarization Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 230000010287 polarization Effects 0.000 description 4
- 150000003077 polyols Chemical group 0.000 description 4
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 2
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 230000002999 depolarising effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- IXLDIJPRDDUUKL-UHFFFAOYSA-N (dimethylamino)methyl benzoate Chemical compound CN(C)COC(=O)C1=CC=CC=C1 IXLDIJPRDDUUKL-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- MLKIVXXYTZKNMI-UHFFFAOYSA-N 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one Chemical compound CCCCCCCCCCCCC1=CC=C(C(=O)C(C)(C)O)C=C1 MLKIVXXYTZKNMI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- PAAVDLDRAZEFGW-UHFFFAOYSA-N 2-butoxyethyl 4-(dimethylamino)benzoate Chemical compound CCCCOCCOC(=O)C1=CC=C(N(C)C)C=C1 PAAVDLDRAZEFGW-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Optical Filters (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明はカラーフィルター用顔料
組成物及びそれを用いたカラ−フィルタ−に関する。更
に詳しくは、液晶表示デバイス等に用いられる光学特性
の優れたカラーフィルタ及びそれ用の顔料組成物に関す
る。FIELD OF THE INVENTION The present invention relates to a pigment composition for a color filter and a color filter using the same. More specifically, the present invention relates to a color filter having excellent optical properties used in a liquid crystal display device and the like and a pigment composition for the same.
【0002】[0002]
【従来の技術】CRT方式からの転換が進みつつあるカ
ラー液晶表示装置等に用いられるカラーフィルターは、
少なくとも2種類以上の色相に着色された微細な画素
と、画素間に光を遮断する目的で設けられるブラックマ
トリクスから形成されている。このカラーフィルターを
作製する方法としては、染料を用いる染色法、染料内添
法、顔料を用いる顔料内添法、電着法、電界ミセル法、
印刷法などが挙げられる。これらの方法のなかで、顔料
を用いる方法は、耐熱性、耐光性に優れ、しかも染色法
に比べカラーフィルターを作製するプロセスが簡略であ
るという特徴を有している。2. Description of the Related Art Color filters used in color liquid crystal display devices and the like, which are being converted from the CRT system, are
It is composed of fine pixels colored in at least two kinds of hues and a black matrix provided for the purpose of blocking light between the pixels. As a method for producing this color filter, a dyeing method using a dye, a dye internal addition method, a pigment internal addition method using a pigment, an electrodeposition method, an electric field micelle method,
Printing method and the like. Among these methods, the method using a pigment is characterized in that it is excellent in heat resistance and light resistance, and that the process for producing a color filter is simpler than in the dyeing method.
【0003】しかしながら、顔料を用いる方法は画素を
可視光が透過する関係で、顔料粒子が透過波長の1/2
の粒子径まで微粒子化処理されていなければならない。
従ってカラ−フィルタ−用顔料としては耐熱性、耐光性
の点で十分実用性があり、かつ微粒子化が容易であると
いう性質を兼ね備えていなければならない。一般に顔料
を分散微粒子化する際、2種類以上の顔料を併用すると
ヘテロ凝集しやすく、良好な透過率を持った分散体が得
にくく、又安定したレオロジーも得にくい。従ってカラ
−フィルタ−用顔料に要求される諸条件を満たす顔料は
少なく、又2種以上の顔料を混合して使用する事も困難
な事が多いので、染料を用いる方法に比べその選択がむ
ずかしく、分光特性的にも使用されうる顔料の選択が限
られるというのが現状である。However, in the method using a pigment, the visible light is transmitted through the pixel, and the pigment particles have a half of the transmission wavelength.
The particle size must be up to the particle size of.
Therefore, the pigment for a color filter must have the properties of being sufficiently practical in terms of heat resistance and light resistance and being easy to be made into fine particles. Generally, when two or more kinds of pigments are used in combination when the pigment is dispersed into fine particles, heteroaggregation is likely to occur, a dispersion having good transmittance is difficult to obtain, and stable rheology is also difficult to obtain. Therefore, there are few pigments that satisfy the various conditions required for color filter pigments, and it is often difficult to mix and use two or more kinds of pigments. Therefore, the selection is more difficult than the method using dyes. At present, the choice of pigments that can be used is limited in terms of spectral characteristics.
【0004】更に、液晶表示の場合、1990年色彩工
学コンファレンスで日本アイ・ビー・エム社から報告さ
れた文献により明らかにされたように、顔料を用いる方
法においては、顔料がカラーフィルターの画素中で粒子
として存在するため、偏光板を通して得られた偏光が顔
料粒子によって一部散乱され偏光性がそこなわれ(これ
を消偏作用とよぶ)、液晶の表示品位、特にそのコント
ラストが染料を用いる方法に比べ低く、黄色顔料を用い
る場合、その性質が顕著であるという問題点を持ってい
る。Further, in the case of liquid crystal display, as disclosed in the literature reported by IBM Japan, Ltd. at the 1990 Color Engineering Conference, in the method using a pigment, the pigment is in the pixel of the color filter. Since the polarized light obtained through the polarizing plate is partly scattered by the pigment particles and the polarization property is impaired (this is called depolarization effect), the display quality of liquid crystal, especially its contrast uses a dye. It is lower than the method, and when using a yellow pigment, there is a problem that its properties are remarkable.
【0005】[0005]
【発明が解決しようとする課題】有機顔料を用いるカラ
ーフィルターの作製において、多様な分光特性が得ら
れ、液晶表示における高い表示品位を可能にするカラー
フィルター用顔料組成物が望まれている。In the production of a color filter using an organic pigment, a pigment composition for a color filter, which can obtain various spectral characteristics and enables a high display quality in a liquid crystal display, is desired.
【0006】[0006]
【課題を解決する為の手段】本発明者らは、前記したよ
うな多様な分光特性得られ、液晶表示品位の良好なカラ
ーフィルターの作製方法を見出すべく鋭意努力した結
果、特定の顔料組成物が、前記の様な特性を満たす事を
見出し、本発明に至ったものである。DISCLOSURE OF THE INVENTION The inventors of the present invention have made diligent efforts to find a method for producing a color filter which has various spectral characteristics as described above and has a good liquid crystal display quality. As a result, a specific pigment composition is obtained. However, the present invention has been completed by finding that the above characteristics are satisfied.
【0007】即ち本発明は、 (1)有機高分子と有機顔料からなる組成物であって、
該有機顔料が2種類以上の顔料の固溶体であることを特
徴とするカラーフィルター用顔料組成物 (2)有機高分子がエチレン性不飽和二重結合を少なく
とも1つ以上有する光重合性化合物と光重合開始剤と場
合によってその他の樹脂からなる感光性樹脂である事を
特徴とする(1)に記載のカラーフィルター用顔料組成
物 (3)その他の樹脂が、皮膜形成性高分子結合剤および
/または熱重合性樹脂である事を特徴とする(2)に記
載のカラーフィルター用顔料組成物 (4)顔料の固溶体が、CI pigment Red
177と黄色顔料である事を特徴とする(1)乃至
(3)に記載のカラーフィルター用顔料組成物 (5)黄色顔料がジクロルベンジジン系ジスアゾ顔料で
あることを特徴とする(4)に記載のカラーフィルター
用顔料組成物 (6)黄色顔料がイソインドリノン系顔料であることを
特徴とする(4)に記載のカラーフィルター用顔料組成
物 (7)顔料の固溶体が、CI pigment Blu
e 15と紫色顔料である事を特徴とする(1)1乃至
(3)に記載のカラーフィルター用顔料組成物 (8)紫色顔料がカルバゾールジオキサジン顔料である
ことを特徴とする(7)に記載のカラーフィルター用顔
料組成物 (8)顔料の固溶体が、下記式(1)で表される化合物
と黄色顔料である事を特徴とする(1)乃至(3)に記
載のカラーフィルター用顔料組成物That is, the present invention provides (1) a composition comprising an organic polymer and an organic pigment,
The organic pigment is a solid solution of two or more kinds of pigments, and a pigment composition for a color filter (2) The organic polymer has a photopolymerizable compound having at least one ethylenically unsaturated double bond and light. Pigment composition for color filter according to (1), which is a photosensitive resin comprising a polymerization initiator and other resin as the case may be. (3) The other resin may be a film-forming polymer binder and / or Or a pigment composition for a color filter according to (2), which is a thermopolymerizable resin. (4) The solid solution of the pigment is CI pigment Red.
177 and a yellow pigment (1) to (3), which is a pigment composition for a color filter (5) The yellow pigment is a dichlorobenzidine-based disazo pigment (4) Pigment composition for color filter described (6) Pigment composition for color filter described in (4), characterized in that the yellow pigment is an isoindolinone pigment (7) The solid solution of the pigment is CI pigment Blu.
(15) The pigment composition for a color filter according to any one of (1) to (3), characterized in that it is a violet pigment. (8) The violet pigment is a carbazole dioxazine pigment (7) Pigment composition for color filter described in (8) Pigment for color filter described in (1) to (3), wherein the solid solution of the pigment is a compound represented by the following formula (1) and a yellow pigment. Composition
【0008】[0008]
【化3】 [Chemical 3]
【0009】(R1 、R2 、R3 、R4 は各々独立し
て、水素、塩素又は臭素を表す。) (10)黄色顔料がジクロルベンジジン系ジスアゾ顔料
であることを特徴とする(9)に記載のカラーフィルタ
ー用顔料組成物 (11)黄色顔料がイソインドリノン系顔料であること
を特徴とする(9)に記載のカラーフィルター用顔料組
成物 (12)顔料の固溶体が、下記式(2)で表される化合
物と黄色顔料である事を特徴とする(1)乃至(3)に
記載のカラーフィルター用顔料組成物(R 1 , R 2 , R 3 and R 4 each independently represent hydrogen, chlorine or bromine.) (10) The yellow pigment is a dichlorobenzidine-based disazo pigment ( (9) The pigment composition for a color filter according to (9), wherein the yellow pigment is an isoindolinone pigment, the pigment composition for a color filter according to (9), (12) a solid solution of the pigment is The pigment composition for color filters according to (1) to (3), which is a compound represented by formula (2) and a yellow pigment.
【0010】[0010]
【化4】 [Chemical 4]
【0011】(R1 およびR2 は各々独立して、水素、
塩素、臭素、アルコキシ基、アルキル基、ニトロ基、カ
ルボアニライド基又はアルコキシカルボニル基を、R
は、水素、塩素、臭素、アルコキシ基、アルキル基、ニ
トロ基、カルボアニライド基、アルコキシカルボニル基
で1置換あるいは2置換されたフェニル基またはベンゾ
イミダゾロン基を表す。) (13)黄色顔料がジクロルベンジジン系ジスアゾ顔料
であることを特徴とする(12)に記載のカラーフィル
ター用顔料組成物 (14)黄色顔料がイソインドリノン系顔料であること
を特徴とする(12)に記載のカラーフィルター用顔料
組成物 (15)(1)乃至(14)のカラーフィルター用顔料
組成物を用いて作製されるカラーフィルター を提供する。(R 1 and R 2 are each independently hydrogen,
Chlorine, bromine, an alkoxy group, an alkyl group, a nitro group, a carboanilide group or an alkoxycarbonyl group, R
Represents hydrogen, chlorine, bromine, an alkoxy group, an alkyl group, a nitro group, a carboanilide group, a phenyl group or a benzimidazolone group mono- or di-substituted with an alkoxycarbonyl group. (13) The pigment composition for a color filter according to (12), wherein the yellow pigment is a dichlorobenzidine-based disazo pigment. (14) The yellow pigment is an isoindolinone-based pigment. (12) Pigment composition for color filter (15) A color filter produced using the pigment composition for a color filter of (1) to (14).
【0012】本発明のカラーフィルター用顔料組成物及
びこれを用いて作製されるカラ−フィルタ−について詳
しく説明する。本発明では、種々の有機顔料から選択さ
れる2種類以上の顔料を、後記する既知の方法で固溶体
化するが、用いうる顔料の具体例としては、ペリレン系
顔料、キナクリドン系顔料、アントラキノン系顔料、モ
ノアゾ系顔料、ジスアゾ系顔料、ピロロピロール系顔
料、イソインドリノン系顔料、フタロシアニン系顔料、
ハロゲン化フタロシアニン系顔料、ジオキサジン系顔料
等が挙げられるが、更にそれらの具体例をカラーインデ
ックス(C.I.)ナンバーで示す。The pigment composition for a color filter of the present invention and the color filter produced using the same will be described in detail. In the present invention, two or more kinds of pigments selected from various organic pigments are made into a solid solution by a known method described below. Specific examples of usable pigments include perylene pigments, quinacridone pigments, and anthraquinone pigments. , Monoazo pigments, disazo pigments, pyrrolopyrrole pigments, isoindolinone pigments, phthalocyanine pigments,
Examples thereof include halogenated phthalocyanine-based pigments and dioxazine-based pigments, and specific examples thereof are shown by color index (CI) numbers.
【0013】 C.I.黄色顔料 20、24、83、86、9
3、109、110、117、125、137、13
8、147、148、153、154、166、168 C.I.赤色顔料 9、97、122、123、1
49、168、177、180、192、208、21
5、216、217、220、223、224、22
6、227、228、240 C.I.紫色顔料 19、23、29、30、37、
40、50 C.I.青色顔料 15、15:1〜6、22、6
0、64 C.I.緑色顔料 7、36C. I. Yellow pigment 20, 24, 83, 86, 9
3, 109, 110, 117, 125, 137, 13
8, 147, 148, 153, 154, 166, 168 C.I. I. Red pigment 9, 97, 122, 123, 1
49, 168, 177, 180, 192, 208, 21
5, 216, 217, 220, 223, 224, 22
6, 227, 228, 240 C.I. I. Purple pigment 19, 23, 29, 30, 37,
40, 50 C.I. I. Blue pigment 15, 15: 1-6, 22, 6
0, 64 C.I. I. Green pigment 7,36
【0014】使用される有機顔料は上記の顔料に限定さ
れるものではなく、又好ましい組合せの例としては、以
下の組合せが挙げられる。 ・顔料の固容体が、CI pigment Red 1
77と黄色顔料からなり、その黄色顔料が、特にジクロ
ルベンジジン系ジスアゾ顔料あるいは、イソインドリノ
ン系顔料であるもの。 ・顔料の固容体が、CI pigment Blue
15と紫色顔料からなり、その紫色顔料がカルバゾール
ジオキサジン顔料であるもの。 ・顔料の固容体が、前記式(1)で表される化合物と黄
色顔料からなり、その黄色顔料が、特にジクロルベンジ
ジン系ジスアゾ顔料あるいは、イソインドリノン系顔料
であるもの。 ・顔料の固容体が、前記式(2)で表される化合物と黄
色顔料であり、この黄色顔料が、特にジクロルベンジジ
ン系ジスアゾ顔料あるいは、イソインドリノン系顔料で
あるもの。The organic pigments used are not limited to the above-mentioned pigments, and examples of preferable combinations include the following combinations.・ The solid solution of the pigment is CI pigment Red 1
77 and a yellow pigment, and the yellow pigment is particularly a dichlorobenzidine-based disazo pigment or an isoindolinone-based pigment.・ Pigment solid solution is CI pigment Blue
15 and a violet pigment, and the violet pigment is a carbazole dioxazine pigment. The pigment solid solution comprises a compound represented by the formula (1) and a yellow pigment, and the yellow pigment is particularly a dichlorobenzidine-based disazo pigment or an isoindolinone-based pigment. The solid solution of the pigment is a compound represented by the formula (2) and a yellow pigment, and the yellow pigment is particularly a dichlorobenzidine-based disazo pigment or an isoindolinone-based pigment.
【0015】これらの顔料から選ばれる2種類以上の顔
料は、他の添加剤等とボールミルなどで処理するか、硫
酸等の顔料が溶解する溶媒に溶解、混合されたのち、顔
料を溶解しない溶媒中で析出させる事により固溶体とさ
れる。Two or more kinds of pigments selected from these pigments are treated with other additives and the like in a ball mill or the like, or are dissolved in a solvent in which the pigment such as sulfuric acid is dissolved and mixed, and then a solvent which does not dissolve the pigment. It is made into a solid solution by precipitating in it.
【0016】本発明で使用される有機高分子としては、
カラーフィルターの当然の要求として無色透明で、耐
熱、耐光性に優れた高分子でなければならず、その具体
例としては以下のものが挙げられる。The organic polymer used in the present invention includes:
As a matter of course, a color filter must be a polymer that is colorless and transparent and has excellent heat resistance and light resistance. Specific examples thereof include the following.
【0017】即ち、エポキシ樹脂、メラミン樹脂、アク
リル樹脂、ポリイミド樹脂および、その前駆体であるポ
リアミック酸樹脂、ポリエステル樹脂、不飽和ポリエス
テル樹脂、ポリカーボネート樹脂、(メタ)アクリロイ
ル基を持つ感光性モノマー、及びオリゴマー、その他の
樹脂等であり、殊に好ましい有機高分子はエチレン性不
飽和二重結合を少なくとも1つ以上有する光重合性化合
物であり、そのような例としては、次のような光重合性
のモノマ−、オリゴマ−、ポリマ−が挙げられる。(メ
タ)アクリロイル基を持つ感光性モノマー、及びオリゴ
マーとしての、エチルアクリレート、ブチルアクリレー
ト、ヒドロキシエチルアクリレート、ヒドロキシエチル
メタクリレート、エチレングリコールジメタアクリレー
ト、ペンタエリスリトールトリアクリレート、ペンタエ
リスリトールトリメタクリレート、ジペンタエリスリト
ールヘキサアクリレート、ジペンタエリスリトールヘキ
サメタクリレート、のような1価又は多価アルコールの
アクリル酸又はメタクリル酸のエステル類;多価アルコ
ールと1塩基酸又は多塩基酸を縮合して得られるポリエ
ステルプレポリマーに(メタ)アクリル酸を反応して得
られるポリエステル(メタ)アクリレート;ポリオール
基と2個のイソシアネート基を持つ化合物を反応させた
後(メタ)アクリル酸を反応して得られるポリウレタン
(メタ)アクリレート;ビスフェノールA型エポキシ樹
脂、ビスフェノールF型エポキシ樹脂、ノボラック型エ
ポキシ樹脂、ポリカルボン酸グリシジルエステル、ポリ
オールポリグリシジルエステル、脂肪族又は脂環式エポ
キシ樹脂、アミンエポキシ樹脂、トリフェノールメタン
型エポキシ樹脂、ジヒドロキシベンゼン型エポキシ樹脂
などのエポキシ樹脂と(メタ)アクリル酸を反応させて
得られるエポキシ(メタ)アクリレートThat is, an epoxy resin, a melamine resin, an acrylic resin, a polyimide resin and its precursors, a polyamic acid resin, a polyester resin, an unsaturated polyester resin, a polycarbonate resin, a photosensitive monomer having a (meth) acryloyl group, and Oligomers, other resins, etc., and particularly preferred organic polymers are photopolymerizable compounds having at least one ethylenically unsaturated double bond, and examples thereof include the following photopolymerizable compounds. Examples thereof include monomers, oligomers and polymers. Ethyl acrylate, butyl acrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, ethylene glycol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol hexa as a photosensitive monomer having a (meth) acryloyl group and an oligomer. Acrylic or methacrylic acid esters of monohydric or polyhydric alcohols such as acrylate, dipentaerythritol hexamethacrylate; polyester prepolymers obtained by condensing polyhydric alcohols with monobasic acids or polybasic acids (meta ) Polyester (meth) acrylate obtained by reacting acrylic acid; (meth) acrylate after reacting a compound having a polyol group and two isocyanate groups Polyurethane (meth) acrylate obtained by reacting phosphoric acid; bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, polycarboxylic acid glycidyl ester, polyol polyglycidyl ester, aliphatic or alicyclic epoxy resin (Meth) acrylate obtained by reacting (meth) acrylic acid with an epoxy resin such as amine, amine epoxy resin, triphenol methane type epoxy resin, dihydroxybenzene type epoxy resin
【0018】(メタ)アクリロイル基とカルボン酸を併
せて持つ、感光性モノマー及び、オリゴマーとして、ビ
スフェノールA型エポキシ樹脂、ビスフェノールF型エ
ポキシ樹脂、ノボラック型エポキシ樹脂、ポリカルボン
酸グリシジルエステル、ポリオールポリグリシジルエス
テル、脂肪族又は脂環式エポキシ樹脂、アミンエポキシ
樹脂、トリフェノールメタン型エポキシ樹脂、ジヒドロ
キシベンゼン型エポキシ樹脂などのエポキシ基と(メ
タ)アクリル酸を反応させて得られるヒドロキシ基に酸
無水物を反応させたエポキシ(メタ)アクリレート カ
ルボン酸付加物;無水マレイン酸と共重合可能な、エチ
レン、プロペン、イソブチレン、スチレン、ビニルフェ
ノール、アクリル酸、アクリル酸エステル、アクリルア
ミド等のモノマーとの共重合体の無水マレイン酸部にヒ
ドロキシエチルアクリレート等のアルコール性のヒドロ
キシ基を持つアクリレートやグリシジルメタクリレート
等のエポキシ基をもつアクリレートを反応させハーフエ
ステル化した化合物;アクリル酸、アクリル酸エステル
とヒドロキシエチルアクリレート等のアルコール性のヒ
ドロキシ基を持つアクリレートの共重合体の−OH基に
さらにアクリル酸を反応せしめた化合物:As photosensitive monomers and oligomers having both a (meth) acryloyl group and a carboxylic acid, bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, polycarboxylic acid glycidyl ester, polyol polyglycidyl Acid anhydrides are added to hydroxy groups obtained by reacting (meth) acrylic acid with epoxy groups such as esters, aliphatic or alicyclic epoxy resins, amine epoxy resins, triphenolmethane type epoxy resins, and dihydroxybenzene type epoxy resins. Reacted epoxy (meth) acrylate carboxylic acid adduct; with a monomer copolymerizable with maleic anhydride, such as ethylene, propene, isobutylene, styrene, vinylphenol, acrylic acid, acrylic ester, acrylamide Compounds obtained by reacting the maleic anhydride portion of the copolymer with an acrylate having an alcoholic hydroxy group such as hydroxyethyl acrylate or an acrylate having an epoxy group such as glycidyl methacrylate to form a half ester; acrylic acid, an acrylic ester and hydroxyethyl A compound obtained by further reacting acrylic acid with -OH group of an acrylate copolymer having an alcoholic hydroxy group such as acrylate:
【0019】本発明の顔料組成物には上記の樹脂類の他
にその他樹脂を添加する事が出来るが、その他の樹脂と
しては皮膜形成性高分子結合剤が挙げられる。皮膜形成
性高分子結合剤の具体例としては、例えば、ポリメタク
リル酸エステル又はその部分加水分解物、ポリ酢酸ビニ
ル又はその加水分解物、ポリビニルフェノール、フェノ
ールノボッラク、ポリスチレン、ポリビニルブチラー
ル、ポリクロロプレン、ポリ塩化ビニル、塩素化ポリエ
チレン、塩素化ポリプロピレン、ポリビニルピロリド
ン、スチレンと無水マレイン酸の共重合体又はそのハー
フエステル、アクリル酸、アクリル酸エステル、メタク
リル酸、メタクリル酸エステル、アクリルアミド、アク
リロニトリルなどの共重合可能なモノマー群から選ばれ
た、ガラス転移点が35℃以上である共重合体などが挙
げられる。In addition to the above resins, other resins can be added to the pigment composition of the present invention. Examples of the other resins include film-forming polymer binders. Specific examples of the film-forming polymer binder include, for example, polymethacrylic acid ester or its partial hydrolyzate, polyvinyl acetate or its hydrolyzate, polyvinylphenol, phenol novolak, polystyrene, polyvinyl butyral and polychloroprene. , Polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyvinylpyrrolidone, copolymer of styrene and maleic anhydride or its half ester, acrylic acid, acrylic acid ester, methacrylic acid, methacrylic acid ester, acrylamide, acrylonitrile, etc. Examples thereof include a copolymer selected from the group of polymerizable monomers and having a glass transition point of 35 ° C. or higher.
【0020】本発明の顔料組成物には更に熱重合性樹脂
を添加する事が出来るが、そのような熱硬化型樹脂重合
性樹脂としてはエポキシ樹脂、メラミン樹脂等が挙げら
れる。そのうちエポキシ樹脂としては、ビスフェノール
A型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、
ノボラック型エポキシ樹脂、ポリカルボン酸グリシジル
エステル、ポリオールポリグリシジルエーテル、脂肪族
又は脂環式エポキシ樹脂、アミンエポキシ樹脂、トリフ
ェノールメタン型エポキシ樹脂、ジヒドロキシベンゼン
型エポキシ樹脂などが、又メラミン樹脂としては、ポリ
メチロールメラミン樹脂、ポリメチロールベンゾグアナ
ミン樹脂等がそれぞれ挙げられる。A thermopolymerizable resin may be further added to the pigment composition of the present invention. Examples of such thermosetting resin-polymerizable resin include epoxy resin and melamine resin. Among them, as the epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin,
Novolak type epoxy resin, polycarboxylic acid glycidyl ester, polyol polyglycidyl ether, aliphatic or alicyclic epoxy resin, amine epoxy resin, triphenol methane type epoxy resin, dihydroxybenzene type epoxy resin and the like, and also as melamine resin, Examples thereof include polymethylol melamine resin and polymethylol benzoguanamine resin.
【0021】本発明で使用される光重合開始剤として
は、種々の光重合開始剤を単独あるいは複合して使用す
ることができるが、一般に、顔料を光重合性樹脂に分散
させる着色光重合性樹脂では、光重合開始剤がラジカル
を発生するのに必要な紫外線が顔料に吸収されてしま
い、充分にラジカルを発生できないため、重合が不十分
となりがちである。従って、光重合開始剤としては高感
度な化合物、あるいは、組成物を使用するのが好まし
い。そのような光重合開始剤の具体例としては、ベンジ
ル;ベンゾインエーテル;ベンゾインイソブチルエーテ
ル;ベンゾインイソプロピルエーテル;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−ベンゾイル−4’−メチルジフェニルサルファイ
ド;ベンジルメチルケタール;2−n−ブトキシエチル
−4−ジメチルアミノベンゾエート;2−クロロチオキ
サントン;2,4−ジエチルチオキサントン;2,4−
ジイソプロピルチオキサントン;ジメチルアミノメチル
ベンゾエート;p−ジメチルアミノ安息香酸イソアミ
ル;3,3’−ジメチル−4−メトキシベンゾフェノ
ン;2,4−ジメチルチオキサントン;1−(4−ドデ
シルフェニル)−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−ヒドロキシ−2−メチル−1−フェニルプロ
パン−1−オン;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;イソ
プロピルチオキサントン;メチルベンゾイルフォーメー
ト;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、2,2’−ビ
ス(o−クロルフェニル)−4,4’,5,5’−テト
ラフェニルビスイミダゾリル;2,2’−ビス(o−ク
ロルフェニル)−4,4’,5,5’−テトラ−(p−
メトキシフェニル)ビスイミダゾリルが挙げられる。こ
れらは単独あるいは、混合して使用しても良く、感光性
樹脂に対し、0.1〜10重量%、好ましくは、0.1
〜5重量%の範囲内で使用される。As the photopolymerization initiator used in the present invention, various photopolymerization initiators can be used alone or in combination, but generally, a colored photopolymerization property in which a pigment is dispersed in a photopolymerizable resin is used. In the resin, the ultraviolet rays required for the photopolymerization initiator to generate radicals are absorbed by the pigment, and the radicals cannot be sufficiently generated, so that the polymerization tends to be insufficient. Therefore, it is preferable to use a highly sensitive compound or composition as the photopolymerization initiator. Specific examples of such a photopolymerization initiator include benzyl; benzoin ether; benzoin isobutyl ether; benzoin isopropyl ether; benzophenone; benzoylbenzoic acid; methyl benzoylbenzoate.
4-benzoyl-4'-methyldiphenyl sulfide; benzyl methyl ketal; 2-n-butoxyethyl-4-dimethylaminobenzoate; 2-chlorothioxanthone; 2,4-diethylthioxanthone; 2,4-
Diisopropylthioxanthone; Dimethylaminomethylbenzoate; Isoamyl p-dimethylaminobenzoate; 3,3'-Dimethyl-4-methoxybenzophenone;2,4-Dimethylthioxanthone; 1- (4-dodecylphenyl) -2-hydroxy-2- Methylpropan-1-one; 1-hydroxycyclohexyl phenyl ketone; 2-hydroxy-2-methyl-1-phenylpropan-1-one; 1- (4-isopropylphenyl)-
2-Hydroxy-2-methylpropan-1-one; isopropylthioxanthone; methylbenzoylformate; 2-methyl-1- [4- (methylthio) phenyl]
-2-morpholinopropan-1-one, 2,2'-bis (o-chlorophenyl) -4,4 ', 5,5'-tetraphenylbisimidazolyl;2,2'-bis (o-chlorophenyl) ) -4,4 ', 5,5'-Tetra- (p-
Methoxyphenyl) bisimidazolyl. These may be used alone or as a mixture and may be used in an amount of 0.1 to 10% by weight, preferably 0.1
Used in the range of up to 5% by weight.
【0022】本発明のおける顔料の固溶体は、可視光を
透過させる必要上、透過光の波長の1/2以下の粒径が
望ましく、さらに望ましくは、200nm以下の粒径に
調製されたものである。前記したような方法で得られた
顔料の固溶体は分散剤あるいは溶剤と共に、サンドミ
ル、三本ロール等の分散機で分散するか、樹脂と共に,
必要により分散剤の存在下で、三本ロ−ル等で混練する
ことにより本発明のカラ−フィルタ−用顔料組成物をえ
る。尚、分散剤としては通常顔料の分散化に使用される
物が使用されうる。このカラ−フィルタ−用顔料組成物
に更にカラ−フィルタ−調製法に応じた樹脂を加えカラ
−フィルタ−調製用の樹脂組成物が作製される。通常顔
料固溶体は樹脂成分に対して10から50重量%の割合
で添加される。The solid solution of the pigment in the present invention has a particle size of 1/2 or less of the wavelength of transmitted light, and more preferably 200 nm or less, in view of the necessity of transmitting visible light. is there. The solid solution of the pigment obtained by the above-mentioned method is dispersed with a dispersant or a solvent in a disperser such as a sand mill or a triple roll, or with a resin,
If necessary, the pigment composition for a color filter of the present invention is obtained by kneading with a triple roll or the like in the presence of a dispersant. As the dispersant, those usually used for dispersing pigments can be used. A resin according to the color filter preparation method is further added to the pigment composition for color filter to prepare a resin composition for color filter preparation. Usually, the pigment solid solution is added at a ratio of 10 to 50% by weight with respect to the resin component.
【0023】次に本発明のカラ−フィルタ−用顔料組成
物を用いたカラ−フィルタ−の調製法について述べる。
本発明の顔料組成物は顔料を用いたカラ−フィルタ−の
通常の製法である顔料内添フォトリソ法、電着法、電界
イセル法、印刷法のいずれの方法にも使用しうる。例え
ば顔料内添フォトリソ法では本発明の顔料組成物、感光
性樹脂、光重合開始剤、溶剤、その他の成分からなる樹
脂組成物を調製し、必要なら、超音波処理機、分散機に
より処理したり、フィルタリングを行った後、スピンナ
−等の塗布機出ガラス板等の基板上に塗布し乾燥した
後、超高圧水銀灯などの光源を用いフォトマスクを介し
て露光し、現像工程を経て1画素を得る。このような操
作を異なった色相の顔料固溶体を含む樹脂組成物を用い
通常3回繰り返すことによりR、G、Bの3色からなる
画素を有するカラ−フィルタ−を得る。又印刷法では、
本発明の顔料組成物とポリアミド樹脂やエポキシ樹脂等
の熱硬化性樹脂及び溶剤からなるインキを印刷機により
ガラス板等の基板に印刷し熱処理を施して1画素を得
る。このような操作を使用する顔料固溶体を代えて3回
行う事によりR、G、Bの3色からなる画素をもつカラ
−フィルタ−を得る。顔料内添フォトリソ法、印刷法以
外の方法についても通常の方法に従い、本発明の顔料組
成物を使用したカラ−フィルタ−が調製される。Next, a method for preparing a color filter using the pigment composition for a color filter of the present invention will be described.
The pigment composition of the present invention can be used in any of the usual methods for producing a color filter using a pigment, such as a pigment internal photolithography method, an electrodeposition method, an electric field isel method, and a printing method. For example, in the photolithography method with internal pigment, a pigment composition of the present invention, a photosensitive resin, a photopolymerization initiator, a solvent, a resin composition comprising other components is prepared, and if necessary, treated with an ultrasonic treatment machine or a disperser. After filtering or filtering, it is coated on a substrate such as a glass plate from a spinner coating machine, dried, and then exposed through a photomask using a light source such as an ultra-high pressure mercury lamp, and a pixel is processed through a developing process. To get This operation is usually repeated three times using resin compositions containing pigment solid solutions having different hues to obtain a color filter having pixels of three colors of R, G and B. In the printing method,
An ink composed of the pigment composition of the present invention, a thermosetting resin such as a polyamide resin or an epoxy resin, and a solvent is printed on a substrate such as a glass plate by a printing machine and heat-treated to obtain one pixel. A color filter having pixels of three colors of R, G, and B is obtained by performing such an operation three times by changing the pigment solid solution using the above operation. A color filter using the pigment composition of the present invention can be prepared according to a usual method other than the photolithography method in which the pigment is added and the printing method.
【0024】本発明の顔料組成物は分散が安定してお
り、この顔料組成物を使用したカラ−フィルタ−は分光
特性に優れ、消偏向作用が小さいという特徴がある。The pigment composition of the present invention is characterized in that the dispersion is stable, and the color filter using this pigment composition has excellent spectral characteristics and a small depolarizing action.
【0025】[0025]
【実施例】以下、実施例により本発明を更に具体的に説
明するが、本発明がこれらの実施例のみに限定されるも
のではない。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【0026】顔料固溶体調製例1 C.I.pigment Red 177の40gと、
C.I.pigment Yellow 83の13.
3gを、濃硫酸200mlに溶解し、室温で2時間攪拌
する。この硫酸溶液を大量の攪拌された氷水中に1時間
かけて投入する。ついで室温で1時間攪拌し、次いでこ
の顔料スラリ−を濾過し、残渣を濾液が中性になるまで
水洗した後、80℃で乾燥した。Pigment Solid Solution Preparation Example 1 C. I. 40g of Pigment Red 177,
C. I. Pigment Yellow 83 13.
3 g is dissolved in 200 ml concentrated sulfuric acid and stirred at room temperature for 2 hours. This sulfuric acid solution is poured into a large amount of stirred ice water over 1 hour. Then, the mixture was stirred at room temperature for 1 hour, the pigment slurry was filtered, the residue was washed with water until the filtrate became neutral, and then dried at 80 ° C.
【0027】顔料固溶体調製例2〜6 上記と同様の方法で、以下表1に記載の組み合わせから
なる顔料固溶体を調製した。Pigment Solid Solution Preparation Examples 2 to 6 Pigment solid solutions comprising the combinations shown in Table 1 below were prepared in the same manner as above.
【0028】[0028]
【表1】 実施例 顔 料 使 用 量 2 CIピグメントレッド 177 40.3g CIピグメントイエロー 185 13.3g 3 CIピグメントグリーン 36 45.0g CIピグメントイエロー 83 5.0g 4 CIピグメントグリーン 36 45.0g CIピグメントイエロー 185 10.0g 5 CIピグメントブルー 15 47.5g CIピグメントバイオレット 23 2.5g 6 CIピグメントレッド 208 40.0g CIピグメントイエロー 83 13.3g 7 CIピグメントレッド 208 40.0g CIピグメントイエロー 185 13.3g[Table 1] Examples Amount of pigment used 2 CI Pigment Red 177 40.3 g CI Pigment Yellow 185 13.3 g 3 CI Pigment Green 36 45.0 g CI Pigment Yellow 83 83 5.0 g 4 CI Pigment Green 36 45.0 g CI Pigment Yellow 185 10.0 g 5 CI Pigment Blue 15 47.5 g CI Pigment Violet 23 2.5 g 6 CI Pigment Red 208 40.0 g CI Pigment Yellow 83 13.3 g 7 CI Pigment Red 208 40.0 g CI Pigment Yellow 185 13. 3 g
【0029】分散化例1 上記、顔料固溶体調製例1で調製された顔料固溶体20
gに対し分散剤としてソルビタン脂肪酸エステル系化合
物を4g加え、さらにエチルセロソルブアセテートを7
6gr加え、サンドミルにて分散化を行った。Dispersion Example 1 Pigment solid solution 20 prepared in Pigment Solid Solution Preparation Example 1 above
4 g of sorbitan fatty acid ester compound as a dispersant was added to 7 g of ethyl cellosolve acetate.
6 gr was added and dispersed by a sand mill.
【0030】分散化例2〜7 上記、顔料固溶体調製例2〜7で調製された顔料固溶体
ついて分散化例1と同様な方法で分散化処理を施した。Dispersion Examples 2 to 7 The pigment solid solutions prepared in the above Pigment Solid Solution Preparation Examples 2 to 7 were subjected to a dispersion treatment in the same manner as in Dispersion Example 1.
【0031】分散化例1から7で得られた顔料固溶体分
散化物の粒子の平均個数分布は200nm以下であっ
た。The average number distribution of particles of the pigment solid solution dispersions obtained in Dispersion Examples 1 to 7 was 200 nm or less.
【0032】実施例1 上記分散化例1で得られた顔料固溶体分散ペーストを1
5g、アーコケミカル製SMA2625(スチレン−マ
レイン酸ハーフエステル)を6.5g、ジペンタエリス
リトールヘキサアクリレートを3.5g、チバ・ガイギ
ー社製イルガキュアー369(光重合開始剤)を0.4
g、日本化薬製カヤキュアーDETX(光重合開始剤)
を0.1g、エチルセロソルブアセテート20gをそれ
ぞれ混合、攪拌し、更に超音波にて10分間分散化処理
して、本発明のカラーフィルター用顔料組成物を得た。Example 1 The pigment solid solution dispersion paste obtained in Dispersion Example 1 was
5 g, SMA2625 (styrene-maleic acid half ester) manufactured by Arco Chemical Co., Ltd., 6.5 g of dipentaerythritol hexaacrylate, and Irgacure 369 (photopolymerization initiator) manufactured by Ciba-Geigy Co., Ltd. 0.4
g, Nippon Kayaku Kayakyu DETX (photopolymerization initiator)
And 0.1 g of ethyl cellosolve acetate were mixed and stirred, and further subjected to dispersion treatment by ultrasonic waves for 10 minutes to obtain a pigment composition for a color filter of the present invention.
【0033】実施例2〜7 実施例1と同様の方法で、分散化例2〜7で得られた顔
料固溶体の分散化物を用いて本発明のカラーフィルター
用顔料組成物を得た。Examples 2 to 7 In the same manner as in Example 1, the pigment solid solution pigment dispersions of the present invention were obtained using the dispersions of the pigment solid solutions obtained in Dispersion Examples 2 to 7.
【0034】比較例1〜7用顔料組成物の調製 C.I.pigment Red 177の15gと、
C.I.pigment Yellow 83の5g
に、分散剤としてソルビタン脂肪酸エステル系化合物を
4gr加え、さらにエチルセロソルブアセテートを76
g加え、サンドミルにて分散化を行った。この顔料ペー
ストを15g、アーコケミカル製SMA2625(スチ
レン−マレイン酸ハーフエステル)を6.5g、ジペン
タエリスリトールヘキサアクリレートを3.5g、チバ
・ガイギー社製イルガキュアー369を0.4g、日本
化薬製カヤキュアーDETXを0.1g、エチルセロソ
ルブアセテート20gをそれぞれ混合、攪拌し、超音波
にて10分間再分散化処理して、比較例1用のカラーフ
ィルター用顔料組成物を得た。前記表1に記載の顔料の
組み合わせ及び使用量により、比較例1と同様の方法で
分散化し、比較用カラーフィルター用顔料組成物2〜7
を得た。Preparation of Pigment Compositions for Comparative Examples 1-7 C.I. I. Pigment Red 177 15g,
C. I. Pigment Yellow 83 5g
4g of sorbitan fatty acid ester compound was added as a dispersant, and ethylcellosolve acetate was added to 76g.
g and dispersed by a sand mill. 15 g of this pigment paste, 6.5 g of SMA2625 (styrene-maleic acid half ester) manufactured by Arco Chemical, 3.5 g of dipentaerythritol hexaacrylate, 0.4 g of Irgacure 369 manufactured by Ciba-Geigy, Nippon Kayaku Kayacure DETX (0.1 g) and ethyl cellosolve acetate (20 g) were mixed, stirred, and subjected to a redispersion treatment with ultrasonic waves for 10 minutes to obtain a pigment composition for a color filter for Comparative Example 1. Pigment compositions 2 to 7 for comparison color filters were dispersed in the same manner as in Comparative Example 1 according to the combination and the amount of use of the pigments shown in Table 1 above.
Got
【0035】実施例8〜14 実施例1で得られたカラーフィルター用顔料組成物を、
コーニング社製7059ガラス基板に乾燥時の膜厚が2
μmとなるように、スピンナーにて塗布、乾燥した。次
いで超高圧水銀灯で100mj露光したのち、200℃
で20分間ポストベークして、膜厚が2μmのカラーフ
ィルターを得た。(実施例8) 実施例2〜6で得られたカラ−フィルタ−用顔料組成物
についても実施例8におけるのと同様にしてそれぞれか
らカラ−フィルタ−を調製した。(実施例9〜14)Examples 8 to 14 The pigment compositions for color filters obtained in Example 1 were
Corning 7059 glass substrate has a dry film thickness of 2
It was applied by a spinner so as to have a thickness of μm and dried. Then, after exposing 100 mj with an ultra-high pressure mercury lamp, 200 ° C
After post-baking for 20 minutes, a color filter having a film thickness of 2 μm was obtained. (Example 8) With respect to the pigment compositions for color filters obtained in Examples 2 to 6, color filters were prepared from each in the same manner as in Example 8. (Examples 9 to 14)
【0036】比較例1〜7 前記比較例1〜7用顔料組成物の調製で得られた顔料組
成物を用い、実施例8〜14におけるのと同様にして比
較用のカラ−フィルタ−を作製した。Comparative Examples 1 to 7 Using the pigment compositions obtained in the preparation of the pigment compositions for Comparative Examples 1 to 7 above, color filters for comparison were prepared in the same manner as in Examples 8 to 14. did.
【0037】性能試験 (1)透過率の測定 実施例8〜14及び比較例1〜7で得られた各々のカラ
−フィルタ−につき透過率を測定した。その結果を表2
の透過率(1)の欄に示した。他方実施例1〜6で得ら
れた組成物及び比較用の組成物についてそれらの調製後
3ヶ月放置した後それらの組成物を用いて前記と同様の
方法でカラ−フィルタ−を調製した。得られたカラ−フ
ィルタ−について透過率を測定し表2の透過率(2)の
欄に示した。 (2)消偏度の測定 実施例8〜14及び比較1〜7で得られたカラ−フィル
タ−につき消偏度を測定し表2に示した。尚、消偏度は
次の方法に依った。2枚の偏光板の間にカラーフィルタ
ーを置いて、偏光軸が平行の時と、垂直の時との輝度比
をコントラストと定義する。次にカラーフィルターを2
枚の偏光板の間に置いた時と、外に置いた時、カラーフ
ィルターに偏光異常(これを消偏作用と呼ぶ)がなけれ
ば両者同一のコントラストが得られるので、この両者の
コントラストの比を、消偏作用の程度を表す、消偏度と
した。尚、表2において消偏度は%で表した。Performance test (1) Measurement of transmittance The transmittance of each of the color filters obtained in Examples 8 to 14 and Comparative Examples 1 to 7 was measured. The results are shown in Table 2.
The transmittance (1) is shown in the column. On the other hand, the compositions obtained in Examples 1 to 6 and the composition for comparison were allowed to stand for 3 months after their preparation, and then the color filters were prepared in the same manner as above using the compositions. The transmittance of the obtained color filter was measured and is shown in the column of transmittance (2) in Table 2. (2) Measurement of Depolarization Deflection The depolarization of the color filters obtained in Examples 8 to 14 and Comparatives 1 to 7 was measured and is shown in Table 2. The depolarization degree was determined by the following method. A color filter is placed between two polarizing plates, and the luminance ratio between when the polarization axes are parallel and when the polarization axes are vertical is defined as the contrast. Then add 2 color filters
When placed between two polarizing plates and when placed outside, the same contrast can be obtained if the color filter has no polarization anomaly (this is called depolarization effect). The degree of depolarization, which represents the degree of depolarization effect, was used. In Table 2, the degree of depolarization is expressed in%.
【0038】 表2 透過率測定波長 透過率(1) 透過率(2) 消偏度 実施例8 610nm 79.2% 79.1% 81% 比較例1 610nm 76.5% 68.3% 61% 実施例9 610nm 80.3% 80.3% 82% 比較例2 610nm 77.5% 70.1% 60% 実施例10 540nm 77.3% 77.3% 80% 比較例3 540nm 74.4% 69.2% 48% 実施例11 540nm 78.3% 78.2% 79% 比較例4 540nm 74.8% 69.4% 47% 実施例12 450nm 84.0% 83.9% 78% 比較例5 450nm 82.1% 79.8% 48% 実施例13 610nm 75.3% 75.3% 82% 比較例6 610nm 74.2% 71.2% 63% 実施例14 610nm 76.2% 76.1% 81% 比較例7 610nm 74.8% 69.5% 59%Table 2 Transmittance measurement wavelength Transmittance (1) Transmittance (2) Depolarization Example 8 610 nm 79.2% 79.1% 81% Comparative Example 1 610 nm 76.5% 68.3% 61% Example 9 610nm 80.3% 80.3% 82% Comparative Example 2 610nm 77.5% 70.1% 60% Example 10 540nm 77.3% 77.3% 80% Comparative Example 3 540nm 74.4% 69.2% 48% Example 11 540nm 78.3% 78.2% 79% Comparative Example 4 540nm 74.8% 69.4% 47% Example 12 450nm 84.0% 83.9% 78% Comparative Example 5 450nm 82.1% 79.8% 48% Example 13 610nm 75.3% 75.3% 82% Comparative Example 6 610nm 74.2% 71.2% 63% Example 14 610nm 76 2% 76.1% 81% Comparative Example 7 610nm 74.8% 69.5% 59%
【0039】表から明らかなように本発明の顔料組成物
は分散安定性に優れているので放置による透過率の変化
が極めて小さく、又消偏率が小さいという特徴がある。As is apparent from the table, the pigment composition of the present invention is excellent in dispersion stability, and therefore has the characteristics that the change in transmittance upon standing is extremely small and the depolarization ratio is small.
【0040】[0040]
【発明の効果】分散安定性が良好で、分光特性の良い、
消偏作用の少ない、カラーフィルター用顔料組成物が得
られた。又本発明の顔料組成物は2種以上の顔料を任意
に組み合わせて使用出来るので、種々の分光特性をもっ
た顔料組成物を調製出来るという特徴がある。The dispersion stability is good and the spectral characteristics are good.
A pigment composition for a color filter having less depolarizing effect was obtained. In addition, the pigment composition of the present invention can be used in any combination of two or more kinds of pigments, so that the pigment composition having various spectral characteristics can be prepared.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 C09B 67/46 Z 7306−4H ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location C09B 67/46 Z 7306-4H
Claims (15)
って、該有機顔料が2種類以上の顔料の固溶体であるこ
とを特徴とするカラーフィルター用顔料組成物。1. A pigment composition for a color filter, which is a composition comprising an organic polymer and an organic pigment, wherein the organic pigment is a solid solution of two or more kinds of pigments.
少なくとも1つ以上有する光重合性化合物と光重合開始
剤と場合によってその他の樹脂からなる感光性樹脂であ
る事を特徴とする請求項1に記載のカラーフィルター用
顔料組成物2. The organic polymer is a photosensitive resin comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond, a photopolymerization initiator, and optionally other resins. Item 1. The pigment composition for a color filter according to Item 1.
および/または熱重合性樹脂である事を特徴とする請求
項2に記載のカラーフィルター用顔料組成物3. The pigment composition for a color filter according to claim 2, wherein the other resin is a film-forming polymer binder and / or a thermopolymerizable resin.
Red 177と黄色顔料である事を特徴とする請求項
1乃至請求項3に記載のカラーフィルター用顔料組成物4. The solid solution of the pigment is CI pigment
The pigment composition for a color filter according to claim 1, which is Red 177 and a yellow pigment.
顔料であることを特徴とする請求項4に記載のカラーフ
ィルター用顔料組成物5. The pigment composition for a color filter according to claim 4, wherein the yellow pigment is a dichlorobenzidine-based disazo pigment.
ことを特徴とする請求項4に記載のカラーフィルター用
顔料組成物6. The pigment composition for a color filter according to claim 4, wherein the yellow pigment is an isoindolinone pigment.
Blue 15と紫色顔料である事を特徴とする請求項
1乃至請求項3に記載のカラーフィルター用顔料組成物7. A solid solution of a pigment is a CI pigment.
Blue 15 and a purple pigment, The pigment composition for color filters of Claim 1 thru | or 3 characterized by the above-mentioned.
であることを特徴とする請求項7に記載のカラーフィル
ター用顔料組成物8. The pigment composition for a color filter according to claim 7, wherein the purple pigment is a carbazole dioxazine pigment.
化合物と黄色顔料である事を特徴とする請求項1乃至請
求項3に記載のカラーフィルター用顔料組成物 【化1】 (R1 、R2 、R3 、R4 は各々独立して、水素、塩素
又は臭素を表す。)9. The color filter pigment composition according to claim 1, wherein the solid solution of the pigment is a compound represented by the following formula (1) and a yellow pigment. (R 1 , R 2 , R 3 and R 4 each independently represent hydrogen, chlorine or bromine.)
ゾ顔料であることを特徴とする請求項9に記載のカラー
フィルター用顔料組成物10. The pigment composition for a color filter according to claim 9, wherein the yellow pigment is a dichlorobenzidine-based disazo pigment.
ることを特徴とする請求項9に記載のカラーフィルター
用顔料組成物11. The pigment composition for a color filter according to claim 9, wherein the yellow pigment is an isoindolinone pigment.
る化合物と黄色顔料である事を特徴とする請求項1乃至
請求項3に記載のカラーフィルター用顔料組成物 【化2】 (R1 およびR2 は各々独立して、水素、塩素、臭素、
アルコキシ基、アルキル基、ニトロ基、カルボアニライ
ド基又はアルコキシカルボニル基を、Rは、水素、塩
素、臭素、アルコキシ基、アルキル基、ニトロ基、カル
ボアニライド基、アルコキシカルボニル基で1置換ある
いは2置換されたフェニル基またはベンゾイミダゾロン
基を表す。)12. The pigment composition for a color filter according to claim 1, wherein the solid solution of the pigment is a compound represented by the following formula (2) and a yellow pigment. (R 1 and R 2 are each independently hydrogen, chlorine, bromine,
An alkoxy group, an alkyl group, a nitro group, a carboanilide group or an alkoxycarbonyl group, and R is a hydrogen atom, a chlorine atom, a bromine atom, an alkoxy group, an alkyl group, a nitro group, a carboanilide group, or an alkoxycarbonyl group, which is substituted by 1 or 2 It represents a substituted phenyl group or a benzimidazolone group. )
ゾ顔料であることを特徴とする請求項12に記載のカラ
ーフィルター用顔料組成物13. The pigment composition for a color filter according to claim 12, wherein the yellow pigment is a dichlorobenzidine-based disazo pigment.
ることを特徴とする請求項12に記載のカラーフィルタ
ー用顔料組成物14. The pigment composition for a color filter according to claim 12, wherein the yellow pigment is an isoindolinone pigment.
ター用顔料組成物を用いて作製されるカラーフィルタ
ー。15. A color filter produced by using the pigment composition for a color filter according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10247792A JPH05281414A (en) | 1992-03-30 | 1992-03-30 | Pigment composition for color filter |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10247792A JPH05281414A (en) | 1992-03-30 | 1992-03-30 | Pigment composition for color filter |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH05281414A true JPH05281414A (en) | 1993-10-29 |
Family
ID=14328539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10247792A Pending JPH05281414A (en) | 1992-03-30 | 1992-03-30 | Pigment composition for color filter |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH05281414A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH1010309A (en) * | 1996-06-25 | 1998-01-16 | Sumitomo Rubber Ind Ltd | Ink for color filter |
JPH1010314A (en) * | 1996-06-26 | 1998-01-16 | Sumitomo Rubber Ind Ltd | Color filter |
JPH10160928A (en) * | 1996-12-02 | 1998-06-19 | Fuji Film Oorin Kk | Coating composition for green color filter |
JPH11256061A (en) * | 1998-03-10 | 1999-09-21 | Mitsubishi Paper Mills Ltd | Novel mixed crystal of phthalocyanine and method for producing electrophotographic photoreceptor using the same |
JP2001354871A (en) * | 2000-04-14 | 2001-12-25 | Sumitomo Chem Co Ltd | Pigment dispersion, photosensitive coloring composition and color filter using the same |
US6596446B2 (en) * | 2000-04-04 | 2003-07-22 | Bayer Aktiengesellschaft | Organic pigments in color filters liquid of crystal display |
JP2005141239A (en) * | 1996-02-02 | 2005-06-02 | Tokyo Ohka Kogyo Co Ltd | Photosensitive composition for green color filter, method for manufacturing green color filter by using the same, green color filter obtained by the method, and color filter having the green color filter |
WO2006011467A1 (en) | 2004-07-29 | 2006-02-02 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigment |
JP2009223344A (en) * | 2009-07-08 | 2009-10-01 | Toyo Ink Mfg Co Ltd | Blue colored composition for color filter and color filter |
US8361680B2 (en) | 2008-12-19 | 2013-01-29 | Boe Technology Group Co., Ltd. | Pigment dispersion solution, pigment photoresist and color filter |
JP2016218188A (en) * | 2015-05-18 | 2016-12-22 | 凸版印刷株式会社 | Green photosensitive composition for solid-state imaging device and color filter using the same |
-
1992
- 1992-03-30 JP JP10247792A patent/JPH05281414A/en active Pending
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005141239A (en) * | 1996-02-02 | 2005-06-02 | Tokyo Ohka Kogyo Co Ltd | Photosensitive composition for green color filter, method for manufacturing green color filter by using the same, green color filter obtained by the method, and color filter having the green color filter |
JPH1010309A (en) * | 1996-06-25 | 1998-01-16 | Sumitomo Rubber Ind Ltd | Ink for color filter |
JPH1010314A (en) * | 1996-06-26 | 1998-01-16 | Sumitomo Rubber Ind Ltd | Color filter |
JPH10160928A (en) * | 1996-12-02 | 1998-06-19 | Fuji Film Oorin Kk | Coating composition for green color filter |
JPH11256061A (en) * | 1998-03-10 | 1999-09-21 | Mitsubishi Paper Mills Ltd | Novel mixed crystal of phthalocyanine and method for producing electrophotographic photoreceptor using the same |
US6596446B2 (en) * | 2000-04-04 | 2003-07-22 | Bayer Aktiengesellschaft | Organic pigments in color filters liquid of crystal display |
JP2001354871A (en) * | 2000-04-14 | 2001-12-25 | Sumitomo Chem Co Ltd | Pigment dispersion, photosensitive coloring composition and color filter using the same |
WO2006011467A1 (en) | 2004-07-29 | 2006-02-02 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigment |
US7888398B2 (en) | 2004-07-29 | 2011-02-15 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigment |
US8361680B2 (en) | 2008-12-19 | 2013-01-29 | Boe Technology Group Co., Ltd. | Pigment dispersion solution, pigment photoresist and color filter |
JP2009223344A (en) * | 2009-07-08 | 2009-10-01 | Toyo Ink Mfg Co Ltd | Blue colored composition for color filter and color filter |
JP2016218188A (en) * | 2015-05-18 | 2016-12-22 | 凸版印刷株式会社 | Green photosensitive composition for solid-state imaging device and color filter using the same |
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