JP3016532B2 - Photosensitive resin composition for color filter and color filter using the same - Google Patents
Photosensitive resin composition for color filter and color filter using the sameInfo
- Publication number
- JP3016532B2 JP3016532B2 JP27809092A JP27809092A JP3016532B2 JP 3016532 B2 JP3016532 B2 JP 3016532B2 JP 27809092 A JP27809092 A JP 27809092A JP 27809092 A JP27809092 A JP 27809092A JP 3016532 B2 JP3016532 B2 JP 3016532B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- photosensitive resin
- resin composition
- color filter
- compound
- 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.)
- Expired - Fee Related
Links
- 239000011342 resin composition Substances 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229920005989 resin Polymers 0.000 claims description 40
- 239000011347 resin Substances 0.000 claims description 40
- 239000004593 Epoxy Substances 0.000 claims description 22
- 239000003086 colorant Substances 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 150000008065 acid anhydrides Chemical class 0.000 claims description 16
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 13
- 150000007519 polyprotic acids Polymers 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- 229920001187 thermosetting polymer Polymers 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000002894 organic compounds Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 25
- 239000000126 substance Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000003822 epoxy resin Substances 0.000 description 18
- 229920000647 polyepoxide Polymers 0.000 description 18
- -1 isocyanate compound Chemical class 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 239000000178 monomer Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 15
- 239000003849 aromatic solvent Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 238000004040 coloring Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 description 10
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 7
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 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 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- 239000012860 organic pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000001062 red colorant Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- UYEDESPZQLZMCL-UHFFFAOYSA-N 1,2-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3SC2=C1 UYEDESPZQLZMCL-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
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
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- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-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
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- WBIOHYFEXBPYSK-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCOCCO WBIOHYFEXBPYSK-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-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
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
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- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- RYLOLRAYISQACV-UHFFFAOYSA-N 4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]benzaldehyde Chemical compound C1=C[N+](C)=CC=C1C=CC1=CC=C(C=O)C=C1 RYLOLRAYISQACV-UHFFFAOYSA-N 0.000 description 1
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- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 108091005944 Cerulean Proteins 0.000 description 1
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- 241000588724 Escherichia coli Species 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 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 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 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
- 239000000038 blue colorant Substances 0.000 description 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- JRJLLXQDXANQEC-UHFFFAOYSA-N fastogen green y Chemical compound [Cu+2].[N-]1C(N=C2C3=C(Cl)C(Cl)=C(Br)C(Cl)=C3C(N=C3C4=C(Br)C(Cl)=C(Br)C(Cl)=C4C(=N4)[N-]3)=N2)=C(C(Br)=C(Cl)C(Br)=C2Cl)C2=C1N=C1C2=C(Cl)C(Cl)=C(Cl)C(Br)=C2C4=N1 JRJLLXQDXANQEC-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000040 green colorant Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- HTENFZMEHKCNMD-UHFFFAOYSA-N helio brilliant orange rk Chemical compound C1=CC=C2C(=O)C(C=C3Br)=C4C5=C2C1=C(Br)C=C5C(=O)C1=CC=CC3=C14 HTENFZMEHKCNMD-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N monomethylhydroquinone Natural products CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
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- KFULNSSZDXUIJW-UHFFFAOYSA-N oxolan-2-ylmethyl prop-2-enoate 2-phenoxyethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCOC1=CC=CC=C1.C(C=C)(=O)OCC1CCCO1 KFULNSSZDXUIJW-UHFFFAOYSA-N 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
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- 230000003595 spectral effect Effects 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、カラー液晶表示装置等
のカラーフィルタの製造に有用な、希アルカリ水溶液で
現像可能なカラーフィルタ用感光性樹脂組成物及びそれ
を用いたカラーフィルタに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photosensitive resin composition for a color filter which is useful for producing a color filter for a color liquid crystal display device and the like and which can be developed with a dilute alkaline aqueous solution, and a color filter using the same.
【０００２】[0002]
【従来の技術】従来より、ガラス基板等の上に形成され
たカラーフィルタが、カラー液晶表示装置、カラーファ
クシミリ、カラービデオカメラ等に広く用いられてき
た。このカラーフィルタの製造においては、カラー液晶
表示装置のＯＡ機器等への用途及び市場の拡大と共に技
術の多様化が進み、染色法、印刷法、電着法及び分散法
等が提案されているが、その中でも染色法が主流であっ
た。2. Description of the Related Art Hitherto, a color filter formed on a glass substrate or the like has been widely used for a color liquid crystal display device, a color facsimile, a color video camera and the like. In the production of this color filter, the use of color liquid crystal display devices for OA equipment and the like and the market are expanding, and the technology is diversified. Dyeing methods, printing methods, electrodeposition methods, dispersion methods and the like have been proposed. Among them, the dyeing method was the mainstream.
【０００３】染色法では、感光性を付与したアクリル樹
脂、ゼラチン等の水溶性レジスト剤を用いてガラス基板
に所定のパターンを形成した後、染色、固着及び防染処
理工程を経て着色パターンを得る。この工程を３回繰り
返して赤色（Ｒ）、緑色（Ｇ）及び青色（Ｂ）の着色層
を作成し、さらに着色層上に保護膜を施すのである。染
色法は、精細性及び分光特性等の面では優れているが、
上記のように工程が複雑であり、また耐久性にやや劣る
という難点がある。In the dyeing method, a predetermined pattern is formed on a glass substrate using a water-soluble resist agent such as an acrylic resin or gelatin imparted with photosensitivity, and then a colored pattern is obtained through a dyeing, fixing and anti-staining process. . This process is repeated three times to form red (R), green (G), and blue (B) colored layers, and a protective film is applied on the colored layers. Although the dyeing method is excellent in terms of fineness and spectral characteristics,
As described above, there are disadvantages that the process is complicated and the durability is slightly inferior.
【０００４】そこで、近年分散法が注目されている。分
散法では、予め着色顔料を分散してあるレジスト剤をガ
ラス基板に塗布し、露光現像によって所定のパターンを
得る。この工程を３回繰り返して赤色（Ｒ）、緑色
（Ｇ）及び青色（Ｂ）の着色層を作成し、さらに必要に
応じて着色層上に保護膜を施すのである。このように、
分散法は、染色、固着工程等が不要なことから生産性の
向上を図ることができ、また必ずしも着色層上に保護膜
を施す必要がない等の利点を有する。分散法に使用され
るレジスト剤として、具体的には、ＳＢＱ−ＰＶＡ系の
感光性樹脂を用いるもの（特開昭６０−１２９７３８
号）、ビニルピロリドン−メチルメタクリレート共重合
系の感光性樹脂等を用いるもの（特開昭６３−３１４５
０１号）等が挙げられる。Therefore, in recent years, the dispersion method has attracted attention. In the dispersion method, a resist agent in which a coloring pigment is dispersed in advance is applied to a glass substrate, and a predetermined pattern is obtained by exposure and development. This process is repeated three times to form red (R), green (G), and blue (B) colored layers, and a protective film is formed on the colored layers as necessary. in this way,
The dispersing method has advantages in that productivity can be improved because a dyeing and fixing step is not required, and a protective film does not necessarily need to be provided on the colored layer. As a resist agent used in the dispersion method, specifically, one using an SBQ-PVA-based photosensitive resin (JP-A-60-129938)
No.) and those using a vinylpyrrolidone-methyl methacrylate copolymer-based photosensitive resin or the like (JP-A-63-3145).
No. 01).
【０００５】しかし、分散法においても、耐熱性の点に
おいては問題がある。特に液晶カラー表示装置のカラー
フィルタに用いられるレジスト剤は、透明導電膜及び配
向膜形成の熱処理工程に晒されるため２００℃以上の熱
で着色しないことが求められるにもかかわらず、上記の
公知感光性樹脂は１８０℃、１時間程度の加熱で黄変
し、特に４５０ｎｍ付近における青色のピーク透過率が
低下すると共にこの透過率を向上させようとすると色純
度が悪くなるのである。However, the dispersion method has a problem in terms of heat resistance. Particularly, the resist agent used for the color filter of the liquid crystal color display device is exposed to a heat treatment step of forming a transparent conductive film and an alignment film, and is required not to be colored by heat of 200 ° C. or more. The conductive resin turns yellow when heated at 180 ° C. for about 1 hour, and particularly, the peak transmittance of blue at around 450 nm decreases, and the color purity deteriorates if the transmittance is to be improved.
【０００６】[0006]
【発明が解決しようとする課題】本発明の課題は、上記
のような耐熱性の問題を解消し、しかも高解像性、耐久
性、耐光性及び耐薬品性に優れた、希アルカリで現像可
能なカラーフィルタ用感光性樹脂組成物及びそれを用い
たカラーフィルタを提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problem of heat resistance, and furthermore, develop with a dilute alkali which is excellent in high resolution, durability, light resistance and chemical resistance. An object of the present invention is to provide a photosensitive resin composition for a color filter and a color filter using the same.
【０００７】[0007]
【課題を解決するための手段】本発明に係る、希アルカ
リ水溶液で現像可能な液状感光性樹脂組成物は、 Ａ．下記一般式（Ｉ）で表される化合物と不飽和モノカ
ルボン酸との反応物に飽和若しくは不飽和多塩基酸無水
物を反応させるか、一般式（Ｉ）で表される化合物と不
飽和モノカルボン酸との反応物に、イソホロンジイソシ
アネート等のイソシアネート基を分子中に少なくとも２
個有するイソシアネート化合物及び飽和若しくは不飽和
多塩基酸無水物を反応させるかによって得られた紫外線
硬化性樹脂、According to the present invention, there is provided a liquid photosensitive resin composition which can be developed with a dilute aqueous alkali solution. A saturated or unsaturated polybasic acid anhydride is reacted with a reaction product of a compound represented by the following general formula (I) and an unsaturated monocarboxylic acid, or a compound represented by the following general formula (I) is reacted with an unsaturated monocarboxylic acid. An isocyanate group such as isophorone diisocyanate is added to the reaction product with the carboxylic acid at least 2 in the molecule.
An ultraviolet-curable resin obtained by reacting an isocyanate compound having one and a saturated or unsaturated polybasic acid anhydride,
【０００８】[0008]
【化３】 Embedded image
【０００９】〔但し、式中、Ｒはｋ個の活性水素を有す
る有機化合物残基、ｎ1 、ｎ2 、ｎ k は０又は１〜５０
の整数で、その和が１〜５０であり、ｋは１〜３の整数
である。また、式中の下記官能基Wherein R is an organic compound residue having k active hydrogens, n 1 , n 2 and nk are 0 or 1 to 50
And the sum is 1 to 50 , and k is an integer of 1 to 3.
It is . Also, the following functional groups in the formula
【００１０】[0010]
【化４】 Embedded image
【００１１】 [0011]
【００１２】（但し、Ｒ’は水素原子、アルキル基、ア
ルキルカルボニル基又はアリールカルボニル基を示す）
に置き換えてもよい。〕(However, R 'represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an arylcarbonyl group.)
May be replaced by ]
【００１３】Ｂ．光重合開始剤、 Ｃ．希釈剤及び Ｄ．着色剤 を含んでなるものである。B. A photopolymerization initiator, C.I. Diluent and D. It contains a coloring agent.
【００１４】なお、上記組成において、さらにＥ．熱硬
化性化合物を含んでもよく、また成分Ａの合成に際し
て、一般式（Ｉ）で表される化合物と不飽和モノカルボ
ン酸との反応物の代わりに一般式（Ｉ）で表される化合
物及びその他のエポキシ化合物と不飽和モノカルボン酸
との反応物を用いてもよい。[0014] In the above composition, E. coli. It may contain a thermosetting compound, and in the synthesis of the component A, a compound represented by the general formula (I) instead of a reaction product of the compound represented by the general formula (I) and the unsaturated monocarboxylic acid; A reaction product of another epoxy compound and an unsaturated monocarboxylic acid may be used.
【００１５】以下本発明を詳細に説明する。 〈Ａ．紫外線硬化性樹脂について〉紫外線硬化性樹脂
は、既述のように、一般式（Ｉ）で表される化合物と不
飽和モノカルボン酸との反応物に飽和若しくは不飽和多
塩基酸無水物を反応させるか、一般式（Ｉ）で表される
化合物と不飽和モノカルボン酸との反応物に、イソホロ
ンジイソシアネート等のイソシアネート基を分子中に少
なくとも２個有するイソシアネート化合物及び飽和若し
くは不飽和多塩基酸無水物を反応させるかによって得ら
れる。Hereinafter, the present invention will be described in detail. <A. Regarding the UV-curable resin> As described above, the UV-curable resin is obtained by reacting a reaction product of a compound represented by the general formula (I) with an unsaturated monocarboxylic acid with a saturated or unsaturated polybasic acid anhydride. Or an isocyanate compound having at least two isocyanate groups such as isophorone diisocyanate in a molecule obtained by reacting a compound represented by the general formula (I) with an unsaturated monocarboxylic acid; and a saturated or unsaturated polybasic anhydride. It is obtained by reacting the product.
【００１６】本発明に使用される一般式（Ｉ）で表され
る脂環式エポキシ樹脂は、公知の方法によって合成する
ことができ、例えば、分子中に活性化水素を有する有機
化合物、すなわちモノアルコール類、ジオール又はトリ
オール等のポリアルコール類、フェノール類、チオール
類、カルボン酸類等を開始剤にして４−ビニルシクロヘ
キセン−１−オキサイドを開環重合させることによって
得られる。これらの有機化合物の中で、本発明において
特に好適なものとしては、メタノール、アリルアルコー
ル、エチレングリコール、グリセリン、トリメチロール
プロパン、ペンタエリスリトール及びアクリル酸等が挙
げられる。The alicyclic epoxy resin represented by the general formula (I) used in the present invention can be synthesized by a known method. For example, an organic compound having activated hydrogen in the molecule, that is, a monofunctional epoxy compound, It is obtained by subjecting 4-vinylcyclohexene-1-oxide to ring-opening polymerization using polyalcohols such as alcohols, diols or triols, phenols, thiols, carboxylic acids and the like as initiators. Among these organic compounds, particularly preferable ones in the present invention include methanol, allyl alcohol, ethylene glycol, glycerin, trimethylolpropane, pentaerythritol and acrylic acid.
【００１７】不飽和モノカルボン酸としては、例えば、
アクリル酸、メタクリル酸、クロトン酸及び桂皮酸等を
挙げることができるが、特にアクリル酸が好ましい。As the unsaturated monocarboxylic acid, for example,
Acrylic acid, methacrylic acid, crotonic acid, cinnamic acid and the like can be mentioned, but acrylic acid is particularly preferred.
【００１８】また、イソシアネート化合物としては、例
えば、２，４−トリレンジイソシアネート、２，６−ト
リレンジイソシアネート、キシリレンジイソシアネー
ト、水添キシリレンジイソシアネート、イソホロンジイ
ソシアネート、４，４’−ジフェニルメタンジイソシア
ネート、トルイジンジイソシアネート、リジンジイソシ
アネート、トリメチレンジイソシアネート、テトラメチ
レンジイソシアネート、ヘキサメチレンジイソシアネー
ト、トリメチルヘキサメチレンジイソシアネート、トリ
フェニルメタントリイソシアネート及びポリメチレンポ
リフェニルポリイソシアネート等を挙げることができ
る。これらは単独で、又は２種類以上併せて使用するこ
とができるが、特にイソホロンジイソシアネート、水添
キシリレンジイソシアネート、トリレンジイソシアネー
ト及びキシリレンジイソシアネート等が好ましく、その
中でも高温時の着色の問題が少ない点からイソホロンジ
イソシアネート及び水添キシリレンジイソシアネート
等、芳香環を有さないものが最適である。Examples of the isocyanate compound include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, 4,4'-diphenylmethane diisocyanate, and toluidine. Examples thereof include diisocyanate, lysine diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, triphenylmethane triisocyanate, and polymethylene polyphenyl polyisocyanate. These can be used alone or in combination of two or more kinds. Particularly, isophorone diisocyanate, hydrogenated xylylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate and the like are preferable, and among them, there is little problem of coloring at high temperature. Most preferred are those having no aromatic ring, such as isophorone diisocyanate and hydrogenated xylylene diisocyanate.
【００１９】さらに、飽和若しくは不飽和多塩基酸無水
物としては、例えば、無水マレイン酸、無水コハク酸、
無水イタコン酸、無水フタル酸、テトラヒドロ無水フタ
ル酸、メチルテトラヒドロ無水フタル酸、無水メチルナ
ジック酸、ヘキサヒドロ無水フタル酸及びメチルヘキサ
ヒドロ無水フタル酸等の２塩基酸無水物、並びに無水ト
リメリット酸、無水ピロメリット酸、無水ベンゾフェノ
ンテトラカルボン酸及びメチルシクロヘキセンテトラカ
ルボン酸無水物等の３塩基酸以上の酸無水物を挙げるこ
とができる。Further, as the saturated or unsaturated polybasic anhydride, for example, maleic anhydride, succinic anhydride,
Dibasic anhydrides such as itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride and methylhexahydrophthalic anhydride; and trimellitic anhydride, anhydride Examples thereof include acid anhydrides of three or more basic acids such as pyromellitic acid, benzophenonetetracarboxylic anhydride and methylcyclohexenetetracarboxylic anhydride.
【００２０】紫外線硬化性樹脂の製造方法を詳細に説明
すると、例えば、一般式（Ｉ）で表される化合物をカル
ビトールアセテート、セロソルブアセテート及びメチル
エチルケトン等の有機溶剤に溶解し、ハイドロキノン及
びハイドロキノンモノメチルエーテル等の熱重合禁止
剤、並びにベンジルジメチルアミン及びトリエチルアミ
ン等の第３級アミン類、並びにトリメチルベンジルアン
モニウムクロライド及びメチルトリエチルアンモニウム
クロライド等の第４級アンモニウム塩類、或はさらにト
リフェニルスチビン等の触媒を使用して、アクリル酸等
の不飽和モノカルボン酸をエポキシ基の１化学当量に対
して好ましくは約０．７〜１．３化学当量、特に好まし
くは約０．９〜１．１化学当量となる比で、常法によ
り、好ましくは６０〜１５０℃、特に好ましくは８０〜
１２０℃の反応温度で反応させて、エポキシアクリレー
トからなる第一の反応生成物を得る。続いて、この第一
の反応生成物に酸無水物を、第一の反応生成物中の水酸
基１化学当量に対して酸無水物０．９９〜０．１０化学
当量となる比で反応させる。このとき、酸無水物として
は前記飽和若しくは不飽和多塩基酸無水物より少なくと
も１種を選択し、常法により、７０〜１２０℃の反応温
度で加熱撹拌により反応させて、所要の紫外線硬化性樹
脂を得る。The method for producing the ultraviolet curable resin will be described in detail. For example, the compound represented by the general formula (I) is dissolved in an organic solvent such as carbitol acetate, cellosolve acetate and methyl ethyl ketone, and hydroquinone and hydroquinone monomethyl ether are dissolved. And tertiary amines such as benzyldimethylamine and triethylamine, and quaternary ammonium salts such as trimethylbenzylammonium chloride and methyltriethylammonium chloride, or a catalyst such as triphenylstibine. The unsaturated monocarboxylic acid such as acrylic acid is used in an amount of preferably about 0.7 to 1.3 chemical equivalents, more preferably about 0.9 to 1.1 chemical equivalents with respect to one chemical equivalent of the epoxy group. In a conventional manner, preferably from 60 to 50 ° C., particularly preferably 80 to
The reaction is performed at a reaction temperature of 120 ° C. to obtain a first reaction product composed of epoxy acrylate. Subsequently, the first reaction product is reacted with an acid anhydride at a ratio of 0.99 to 0.10 chemical equivalents of the acid anhydride to 1 chemical equivalent of the hydroxyl group in the first reaction product. At this time, as the acid anhydride, at least one selected from the above-mentioned saturated or unsaturated polybasic acid anhydrides is reacted by heating and stirring at a reaction temperature of 70 to 120 ° C. according to a conventional method to obtain a desired ultraviolet curable property. Obtain resin.
【００２１】また、イソホロンジイソシアネート等のイ
ソシアネート化合物を紫外線硬化性樹脂の合成に使用す
る場合は、まず、前記第一の反応生成物を得た後、イソ
シアネート化合物を、前者の２級水酸基１化学当量に対
して好ましくはイソシアネート基０．０１〜０．９０化
学当量、特に好ましくはイソシアネート基０．０５〜
０．４０化学当量となる比で、常法により、触媒として
ジブチルスズジラウレート等の有機スズ化合物若しくは
ベンジルジメチルアミン等の第３級アミン類を加えて又
は加えずに先の反応で配合した触媒で、２０〜１００℃
の反応温度で加熱撹拌により反応させて、第二の反応生
成物を得る。なお、第一の反応生成物中の水酸基１化学
当量に対するイソシアネート基の前記反応量が０．９０
化学当量より多い場合は希釈剤に対する紫外線硬化性樹
脂の溶解性が不良となり易く、特に０．０５〜０．４０
化学当量の範囲で最良の使用特性が得られる。When an isocyanate compound such as isophorone diisocyanate is used for synthesizing an ultraviolet-curable resin, first, the first reaction product is obtained, and then the isocyanate compound is replaced with one equivalent of the secondary hydroxyl group of 1 equivalent. Is preferably 0.01 to 0.90 chemical equivalent of isocyanate group, and particularly preferably 0.05 to 0.05 isocyanate group.
At a ratio of 0.40 chemical equivalents, a catalyst blended in the previous reaction with or without the addition of an organic tin compound such as dibutyltin dilaurate or a tertiary amine such as benzyldimethylamine as a catalyst by a conventional method, 20-100 ° C
The reaction is carried out by heating and stirring at the reaction temperature described above to obtain a second reaction product. The reaction amount of the isocyanate group with respect to 1 chemical equivalent of the hydroxyl group in the first reaction product is 0.90.
When the amount is larger than the chemical equivalent, the solubility of the ultraviolet curable resin in the diluent tends to be poor, and particularly, 0.05 to 0.40.
The best use characteristics are obtained in the range of the chemical equivalent.
【００２２】続いて、前記第二の反応生成物に酸無水物
を、先の第一の反応生成物中の水酸基１化学当量に対し
て酸無水物０．９９〜０．１０化学当量となる比で反応
させる。このとき酸無水物としては前記飽和若しくは不
飽和多塩基酸無水物の内より少なくとも１種選択し、常
法により、好ましくは７０〜１２０℃で加熱撹拌により
反応させて紫外線硬化性樹脂を得る。Subsequently, an acid anhydride is added to the second reaction product in an amount of 0.99 to 0.10 chemical equivalents of the acid anhydride to 1 chemical equivalent of the hydroxyl group in the first reaction product. Reaction in ratio. At this time, as the acid anhydride, at least one selected from the above-mentioned saturated or unsaturated polybasic acid anhydrides is selected, and reacted by a conventional method, preferably by heating and stirring at 70 to 120 ° C. to obtain an ultraviolet curable resin.
【００２３】紫外線硬化性樹脂は、一般式（Ｉ）で表さ
れる化合物の分子量を適宜選択することで、優れた耐熱
性を有するのみならず、プリキュア後の被膜強度の優れ
た皮膜特性が得られるため、いわゆるオフコンタクト法
のみならず、パターンの接触露光が容易に可能になり、
また低光量での露光においても良好なパターン形成を可
能とする優れたレジスト剤を得ることができる。同よう
の被膜特性の調節は上記のごとく一部イソシアネート架
橋することによっても可能である。By appropriately selecting the molecular weight of the compound represented by the general formula (I), the UV-curable resin can have not only excellent heat resistance but also excellent film properties such as excellent film strength after precure. Therefore, not only the so-called off-contact method, but also the contact exposure of the pattern is easily possible,
Further, it is possible to obtain an excellent resist agent capable of forming a good pattern even in exposure with a low light amount. The same adjustment of the coating properties can be achieved by partially crosslinking the isocyanate as described above.
【００２４】なお、紫外線硬化性樹脂は、前記の合成例
に限らず、常法での種々の合成法によって合成可能であ
り、例えば一般式（Ｉ）で表される化合物にアクリル酸
等の不飽和モノカルボン酸を反応させてエポキシアクリ
レートとした後、先ず酸無水物を反応させ、その後にイ
ソシアネート化合物等を反応させて合成することもでき
る。The UV-curable resin is not limited to the above-mentioned synthesis examples, and can be synthesized by various conventional synthesis methods. For example, the compound represented by the general formula (I) may be synthesized with a compound such as acrylic acid. After the reaction with a saturated monocarboxylic acid to form an epoxy acrylate, first, an acid anhydride may be reacted, and then, an isocyanate compound or the like may be reacted for synthesis.
【００２５】ところで、紫外線硬化性樹脂の原料エポキ
シ化合物として、一般式（Ｉ）で表される化合物のみな
らず、一般式（Ｉ）で表される化合物とその他のエポキ
シ化合物、例えばビスフェノール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（フェノールノボラック型、クレゾールノボラック
型）、環式脂肪族エポキシ樹脂、トリス（ヒドロキシフ
ェニル）メタンベースの多官能エポキシ樹脂、油化シェ
ルエポキシ社製エピコート１５７シリーズに相当するエ
ポキシ樹脂、トリグリシジルイソシアヌレート等との混
合物を用いることも可能である。しかしながら、ここに
列挙したその他のエポキシ化合物の多くは、多量配合す
ると加熱による着色を招き易いので、当該原料エポキシ
化合物全量に占める一般式（Ｉ）で表される化合物の配
合比率を、２５重量％以上、特に５０重量％以上に保持
することが望ましい。Incidentally, as the raw material epoxy compound of the ultraviolet curable resin, not only the compound represented by the general formula (I) but also the compound represented by the general formula (I) and other epoxy compounds, for example, bisphenol A type epoxy Resin, bisphenol F type epoxy resin, novolak type epoxy resin (phenol novolak type, cresol novolak type), cycloaliphatic epoxy resin, polyfunctional epoxy resin based on tris (hydroxyphenyl) methane, Epicoat 157 manufactured by Yuka Shell Epoxy It is also possible to use a mixture with an epoxy resin, triglycidyl isocyanurate or the like corresponding to the series. However, many of the other epoxy compounds listed here are liable to be colored by heating when blended in a large amount, so that the compounding ratio of the compound represented by the general formula (I) in the total amount of the raw material epoxy compound is 25% by weight. It is desirable to keep the above, especially at least 50% by weight.
【００２６】得られた紫外線硬化性樹脂の酸価は、３０
〜１６０ｍｇＫＯＨ／ｇ程度であることが好ましい。そ
の酸価が３０より小さい場合はアルカリ現像液に対する
溶解性が悪くなり、逆に１６０より大きい場合は硬化レ
ジスト皮膜の耐薬品性等の特性を低下させる要因とな
る。The acid value of the obtained ultraviolet curable resin is 30.
It is preferably about 160 mgKOH / g. If the acid value is less than 30, the solubility in an alkali developing solution will be poor, and if it is greater than 160, it will be a factor of deteriorating properties such as chemical resistance of the cured resist film.
【００２７】なお、前記紫外線硬化性樹脂には、公知の
多塩基酸無水物を付加したエポキシアクリレート、その
他エポキシ化合物から本発明に係る紫外線硬化性樹脂と
同ようの製法で誘導した紫外線硬化性樹脂を適宜併用す
ることもできる。The UV-curable resin may be a known UV-curable resin derived from a known polybasic acid anhydride-added epoxy acrylate or other epoxy compound in the same manner as the UV-curable resin according to the present invention. Can also be used in combination as appropriate.
【００２８】〈Ｂ．光重合開始剤について〉光重合開始
剤としては、例えば、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及びベンゾインイソ
プロピルエーテル等のベンゾインとそのアルキルエーテ
ル類、並びにアセトフェノン、２，２−ジメトキシ−２
−フェニルアセトフェノン、２，２−ジエトキシ−２−
フェニルアセトフェノン、１，１−ジクロロアセトフェ
ノン、１−ヒドロキシシクロヘキシルフェニルケトン及
び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−オン等のアセトフェ
ノン類、並びに２−メチルアントラキノン及び２−アミ
ルアントラキノン等のアントラキノン類、並びに２，４
−ジメチルチオキサントン、２，４−ジエチルチオキサ
ントン、２−クロロチオキサントン及び２，４−ジイソ
プロピルチオキサントン等のチオキサントン類、並びに
アセトフェノンジメチルケタール及びベンジルジメチル
ケタール等のケタール類、並びにベンゾフェノン等のベ
ンゾフェノン類又はキサントン類、並びにルシリンＴＰ
Ｏ（ＢＡＳＦ社製 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シド）等を挙げることがで
き、これらは安息香酸系又は第三級アミン系等の公知の
光重合促進剤と併用してもよい。これらの光重合開始剤
は、紫外線硬化性樹脂１００重量部に対して好ましくは
０．１〜３０重量部、特に好ましくは１〜２５重量部配
合される。<B. Regarding photopolymerization initiator> Examples of photopolymerization initiators include benzoin such as benzoin, benzoin methyl ether, benzoin ethyl ether and benzoin isopropyl ether and their alkyl ethers, and acetophenone, 2,2-dimethoxy-2.
-Phenylacetophenone, 2,2-diethoxy-2-
Phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexyl phenyl ketone and 2-methyl-1- [4- (methylthio) phenyl]-
Acetophenones such as 2-morpholino-propan-1-one and anthraquinones such as 2-methylanthraquinone and 2-amylanthraquinone, and 2,4
-Thioxanthones such as dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone and 2,4-diisopropylthioxanthone, and ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal, and benzophenones or xanthones such as benzophenone; And Lucirin TP
O (2,4,6-trimethylbenzoyldiphenylphosphine oxide manufactured by BASF) and the like may be used, and these may be used in combination with a known photopolymerization accelerator such as a benzoic acid or a tertiary amine. These photopolymerization initiators are preferably used in an amount of 0.1 to 30 parts by weight, particularly preferably 1 to 25 parts by weight, based on 100 parts by weight of the ultraviolet curable resin.
【００２９】〈Ｃ．希釈剤について〉希釈剤としては、
光重合性モノマー及び／又は有機溶剤を使用することが
できる。前記光重合性モノマーとして、例えば、２−ヒ
ドロキシエチルアクリレート、２−ヒドロキシプロピル
アクリレート、Ｎ−ビニルピロリドン、アクリロイルモ
ルフォリン、メトキシテトラエチレングリコールアクリ
レート、メトキシポリエチレングリコールアクリレー
ト、ポリエチレングリコールジアクリレート、Ｎ，Ｎ−
ジメチルアクリルアミド、Ｎ−メチロールアクリルアミ
ド、Ｎ，Ｎ−ジメチルアミノプロピルアクリルアミド、
Ｎ，Ｎ−ジメチルアミノエチルアクリレート、Ｎ，Ｎ−
ジメチルアミノプロピルアクリレート及びメラミンアク
リレート、又は前記アクリレートに対応する各メタクリ
レート等の水溶性モノマー、並びにジエチレングリコー
ルジアクリレート、トリエチレングリコールジアクリレ
ート、プロピレングリコールジアクリレート、トリプロ
ピレングリコールジアクリレート、フェノキシエチルア
クリレートテトラヒドロフルフリルアクリレート、シク
ロヘキシルアクリレート、トリメチロールプロパンジア
クリレート、トリメチロールプロパントリアクリレー
ト、ペンタエリスリトールトリアクリレート、ペンタエ
リスリトールテトラアクリレート、ジペンタエリスリト
ールペンタアクリレート、ジペンタエリスリトールヘキ
サアクリレート、イソボニルアクリレート、シクロペン
タニル（モノ又はジ）アクリレート、シクロペンテニル
（モノ又はジ）アクリレート、又は前記アクリレートに
対応する各メタクリレート類及び多塩基酸とヒドロキシ
アルキル（メタ）アクリレートとのモノ−、ジ−、トリ
−又はそれ以上のポリエステル等の非水溶性モノマー、
並びにポリエステルアクリレート、ウレタンアクリレー
ト、ビスフェノールＡ型エポキシアクリレート、フェノ
ールノボラック型エポキシアクリレート及びクレゾール
ノボラック型エポキシアクリレート、トリグリシジルイ
ソシアヌレート若しくは一般式（Ｉ）で表される化合物
から誘導されるエポキシアクリレート等のエポキシアク
リレート（これらのエポキシアクリレートはイソシアネ
ート基を分子中に少なくとも２個有する化合物若しくは
多塩基酸無水物等で一部架橋されていてもよい）、ポリ
エステルアクリレート、ウレタンアクリレート等の高分
子量アクリレートモノマー等を挙げることができる。前
記水溶性モノマー、非水溶性モノマー及び高分子アクリ
レートモノマー等は各々単独で或いは適宜互いに組み合
わせて使用することができる。<C. About diluent> As diluent,
Photopolymerizable monomers and / or organic solvents can be used. Examples of the photopolymerizable monomer include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, N-vinylpyrrolidone, acryloylmorpholine, methoxytetraethylene glycol acrylate, methoxypolyethylene glycol acrylate, polyethylene glycol diacrylate, and N, N-.
Dimethylacrylamide, N-methylolacrylamide, N, N-dimethylaminopropylacrylamide,
N, N-dimethylaminoethyl acrylate, N, N-
Water-soluble monomers such as dimethylaminopropyl acrylate and melamine acrylate, or each methacrylate corresponding to the acrylate, and diethylene glycol diacrylate, triethylene glycol diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, phenoxyethyl acrylate tetrahydrofurfuryl Acrylate, cyclohexyl acrylate, trimethylolpropane diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, isobornyl acrylate, cyclopentanyl (mono or di Water-insoluble such as acrylate, cyclopentenyl (mono or di) acrylate, or methacrylates corresponding to the acrylate and mono-, di-, tri- or higher polyesters of polybasic acid and hydroxyalkyl (meth) acrylate Monomer,
And epoxy acrylates such as polyester acrylate, urethane acrylate, bisphenol A epoxy acrylate, phenol novolak epoxy acrylate and cresol novolak epoxy acrylate, epoxy acrylate derived from triglycidyl isocyanurate or a compound represented by the general formula (I). (These epoxy acrylates may be partially crosslinked with a compound having at least two isocyanate groups in the molecule or a polybasic acid anhydride), and high molecular weight acrylate monomers such as polyester acrylate and urethane acrylate. Can be. The water-soluble monomer, the water-insoluble monomer, the polymer acrylate monomer and the like can be used alone or in combination with one another as appropriate.
【００３０】また、前記有機溶剤としては、例えば、メ
チルエチルケトン及びシクロヘキサノン等のケトン類、
並びにトルエン及びキシレン等の芳香族炭化水素類、並
びにセロソルブ及びブチルセロソルブ等のセロソルブ
類、並びにカルビトール及びブチルカルビトール等のカ
ルビトール類、並びに酢酸エチル、酢酸ブチル、セロソ
ルブアセテート、ブチルセロソルブアセテート及びブチ
ルカルビトールアセテート、プロピレングリコールモノ
メチルエーテルアセテート等の酢酸エステル類等を挙げ
ることができる。Examples of the organic solvent include ketones such as methyl ethyl ketone and cyclohexanone;
And aromatic hydrocarbons such as toluene and xylene; and cellosolves such as cellosolve and butyl cellosolve; and carbitols such as carbitol and butyl carbitol; and ethyl acetate, butyl acetate, cellosolve acetate, butyl cellosolve acetate and butyl carbitol. Acetates such as acetate and propylene glycol monomethyl ether acetate can be exemplified.
【００３１】前記水溶性モノマー、非水溶性モノマー及
び高分子量アクリレートモノマー等の光重合性モノマー
は、紫外線硬化性樹脂を希釈し、塗布し易い状態にする
と共に酸価及び光重合性を調節する。水溶性モノマーを
単独で或は非水溶性モノマーや高分子量アクリレートモ
ノマー等と組み合わせて使用する場合は、水溶性モノマ
ーの配合比率が多くなるとアルカリ水溶液への溶解性が
向上するが、これを多用すると完全硬化したレジスト皮
膜の耐水性が低下するので、このレジスト皮膜がアルカ
リ水溶液に難溶とならない程度に、好ましくは紫外線硬
化性樹脂に対して１００重量％以下の範囲で配合すれば
よい。また、前記有機溶剤は、紫外線硬化性樹脂を溶
解、希釈し、液状として塗布可能にすると共に乾燥によ
り造膜させる。The photopolymerizable monomer such as the water-soluble monomer, water-insoluble monomer, and high-molecular-weight acrylate monomer dilutes the ultraviolet-curable resin to make it easy to apply, and adjusts the acid value and photopolymerizability. When a water-soluble monomer is used alone or in combination with a water-insoluble monomer or a high-molecular-weight acrylate monomer, the solubility in an alkaline aqueous solution is improved when the mixing ratio of the water-soluble monomer is increased. Since the water resistance of the completely cured resist film is reduced, the resist film may be blended to such an extent that the resist film does not become sparingly soluble in an aqueous alkali solution, preferably in a range of 100% by weight or less based on the ultraviolet curable resin. In addition, the organic solvent dissolves and dilutes the ultraviolet curable resin, makes it applicable as a liquid, and forms a film by drying.
【００３２】前記希釈剤は、塗布方法にもよるが、単独
で又は２種以上の混合物として感光性樹脂組成物全量に
対して１０〜９５重量％の範囲で配合することが好まし
い。The above-mentioned diluent is preferably used alone or as a mixture of two or more kinds in a range of 10 to 95% by weight based on the total amount of the photosensitive resin composition, though it depends on a coating method.
【００３３】〈Ｄ．着色剤〉本発明の感光性熱硬化性樹
脂組成物に使用される着色剤は、塗膜をカラーフィルタ
用に着色させるものであり、例えば、アゾレーキ系、不
溶性アゾ系、フタロシアニン系、キナクリドン系、ジオ
キサジン系、イソインドリノン系、ペリノン系、アント
ラキノン系、ペリレン系、スレン系及びアゾ系の有機顔
料、の有機顔料、並びにミロリブルー、酸化鉄、コバル
ト系、マンガン系、群青、紺青、コバルトブルー、セル
リアンブルー、ピリアジン、エメラルドグリーン及びコ
バルトグリーン等の無機顔料、並びに油溶性染料、分散
性、塩基性染料及び分散染料等の染料を単独若しくは混
合して使用することができる。<D. Colorant> The colorant used in the photosensitive thermosetting resin composition of the present invention is used to color a coating film for a color filter.For example, an azo lake type, an insoluble azo type, a phthalocyanine type, a quinacridone type, Organic pigments of dioxazine type, isoindolinone type, perinone type, anthraquinone type, perylene type, sulene type and azo type organic pigments, as well as milor blue, iron oxide, cobalt type, manganese type, ultramarine, navy blue, cobalt blue, cerulean Inorganic pigments such as blue, pyriazine, emerald green and cobalt green, and dyes such as oil-soluble dyes, dispersible, basic dyes and disperse dyes can be used alone or in combination.
【００３４】〈Ｅ．熱硬化性化合物〉以上の各成分Ａ〜
Ｄを含んでなる感光性樹脂組成物には、さらに熱硬化性
化合物、例えば熱硬化性エポキシ化合物を含ませて、光
硬化反応及び熱硬化反応を同時に或いは逐次的に進行さ
せることにより、密着性、耐光性、耐薬品性及び皮膜強
度等の一層の向上を図ってもよい。<E. Thermosetting compound> Each of the above components A to
The photosensitive resin composition containing D further contains a thermosetting compound, for example, a thermosetting epoxy compound, and allows the photocuring reaction and the thermosetting reaction to proceed simultaneously or sequentially, thereby improving the adhesion. Further, light resistance, chemical resistance, film strength and the like may be further improved.
【００３５】上記熱硬化性エポキシ化合物としては、例
えば、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、フェノールノボラック型エポキシ
樹脂、クレゾールノボラック型エポキシ樹脂、Ｎ−グリ
シジル型エポキシ樹脂又は脂環式エポキシ樹脂、「ＹＸ
−４０００」（油化シェルエポキシ社製エポキシ樹脂）
等、一分子中に２個以上のエポキシ基を有するものを挙
げることができるが、耐熱性の点からは、特に水添ビス
フェノールＡ型エポキシ樹脂、トリグリシジルイソシア
ヌレート及び本発明において用いられる一般式（Ｉ）で
表される化合物等が望ましい。Examples of the thermosetting epoxy compound include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, N-glycidyl type epoxy resin and alicyclic epoxy resin. , "YX
-4000 "(epoxy resin manufactured by Yuka Shell Epoxy)
Examples thereof include those having two or more epoxy groups in one molecule. From the viewpoint of heat resistance, hydrogenated bisphenol A type epoxy resin, triglycidyl isocyanurate and the general formula used in the present invention are particularly preferable. The compound represented by (I) is desirable.
【００３６】なお、本発明に係る感光性樹脂組成物に
は、さらに必要に応じて、イミダゾール誘導体、ポリア
ミン類、グアナミン類、３級アミン類、４級アンモニウ
ム塩類、ポリフェノール類及び多塩基酸無水物等のエポ
キシ樹脂硬化剤及び硬化促進剤類、並びに硫酸バリウ
ム、酸化珪素、タルク、クレー及び炭酸カルシウム等の
充填剤、並びに消泡剤、シランカップリング剤等の密着
性付与剤、レベリング剤、ハレーション防止剤及び分散
剤等の各種添加剤、或はハイドロキノン、ハイドロキノ
ンモノメチルエーテル、ピロガロール、ターシャリブチ
ルカテコール及びフェノチアジン等の重合禁止剤等を加
えてもよい。The photosensitive resin composition according to the present invention may further contain an imidazole derivative, a polyamine, a guanamine, a tertiary amine, a quaternary ammonium salt, a polyphenol and a polybasic acid anhydride, if necessary. Epoxy resin curing agents and curing accelerators; fillers such as barium sulfate, silicon oxide, talc, clay and calcium carbonate; and adhesion promoters such as defoamers and silane coupling agents, leveling agents, and halation. Various additives such as an inhibitor and a dispersant, or a polymerization inhibitor such as hydroquinone, hydroquinone monomethyl ether, pyrogallol, tert-butylcatechol and phenothiazine may be added.
【００３７】本発明に係る感光性樹脂組成物は、例え
ば、前述したＡ〜Ｄ或はＡ〜Ｅの各配合成分及び添加剤
等を三本ロール、ボールミル、サンドミル等で混練する
ことによって調製される。The photosensitive resin composition according to the present invention is prepared, for example, by kneading the above-mentioned components A to D or A to E, additives and the like with a three-roll, ball mill, sand mill or the like. You.
【００３８】本発明に係る感光性樹脂組成物の使用方法
としては、例えば、ガラス基板上に浸漬法、スプレー、
スピンコーター、ロールコーター又はスクリーン印刷等
により塗布した後、溶剤を揮発させるために例えば６０
〜１２０℃で加熱乾燥を行ない、その後、パターンを描
いたマスクを乾燥した塗膜表面に接触させ又は接触させ
ずに当てがい、ケミカルランプ、低圧水銀灯、中圧水銀
灯、高圧水銀灯、超高圧水銀灯、キセノンランプ又はメ
タルハライドランプ等を用いて紫外線を照射し、現像し
てパターンを形成することにより目的とするレジスト皮
膜を形成させることができる。また、熱硬化性化合物を
配合した場合等においては、現像後、さらに加熱硬化工
程を加えてもよい。The method of using the photosensitive resin composition according to the present invention includes, for example, immersion on a glass substrate, spraying,
After being applied by a spin coater, a roll coater or screen printing, for example, 60
Heat drying at ~ 120 ° C, then apply the mask with the pattern drawn on or without contacting the dried coating surface, chemical lamp, low-pressure mercury lamp, medium-pressure mercury lamp, high-pressure mercury lamp, ultra-high-pressure mercury lamp, A target resist film can be formed by irradiating ultraviolet rays using a xenon lamp or a metal halide lamp and developing the pattern to form a pattern. In the case where a thermosetting compound is added, a heat curing step may be further added after the development.
【００３９】[0039]
【実施例】以下に、実施例及び比較例を示して本発明を
具体的に説明するが、本発明はそれらの実施例に限定さ
れるものではない。なお、以下に使用される「部」及び
「％」は全て重量基準であり、また「着色剤」について
は、赤色の場合はリオノーゲンレッドＧＤ（東洋インキ
製造社製）、青色の場合はリオノールブルーＥＳ（東洋
インキ製造社製）、また緑色の場合はリオノールグリー
ン２ＹＳ（東洋インキ製造社製）を各々使用した。EXAMPLES The present invention will be specifically described below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following, "parts" and "%" are all based on weight, and "colorant" is Lionogen Red GD (manufactured by Toyo Ink Mfg. Co., Ltd.) for red, and Rio Nord Blue ES (manufactured by Toyo Ink Mfg. Co., Ltd.) and, in the case of green, Lionol Green 2YS (manufactured by Toyo Ink Mfg. Co., Ltd.) were used.
【００４０】〔実施例１〕下記の一般式（II）で表され
る化合物〔ＥＨＰＥ−３１５０ ダイセル化学工業
（株）社製 エポキシ当量１８５〕Example 1 Compound represented by the following general formula (II) [EHPE-3150, epoxy equivalent 185, manufactured by Daicel Chemical Industries, Ltd.]
【００４１】[0041]
【化５】 Embedded image
【００４２】（式中、ｎ1 、ｎ2 、ｎ3 は１〜１８の整
数で、その和が１０〜２０である。）１８５部をカルビ
トールアセテート６０部に加熱溶解したものに、撹拌下
にアクリル酸７４部、ハイドロキノン０．１部及びベン
ジルジメチルアミン０．７部を加え、常法により９０〜
１００℃で２４時間反応させた。この反応液を冷却後、
カルビトールアセテート６５部、スワゾール１５００
（丸善石油化学社製芳香族系溶剤）１２５部及びテトラ
ヒドロ無水フタル酸７６部を加え、１００℃に昇温する
と共に撹拌下に約３時間反応させ、紫外線硬化性樹脂
（Ａ−１）を得た。(Wherein n 1 , n 2 , and n 3 are integers of 1 to 18 and the sum is 10 to 20). A solution prepared by heating and dissolving 185 parts in 60 parts of carbitol acetate is stirred under stirring. To the mixture were added 74 parts of acrylic acid, 0.1 part of hydroquinone and 0.7 parts of benzyldimethylamine.
The reaction was performed at 100 ° C. for 24 hours. After cooling the reaction,
Carbitol acetate 65 parts, Swazole 1500
(Aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 125 parts and tetrahydrophthalic anhydride 76 parts were added, and the mixture was heated to 100 ° C. and reacted under stirring for about 3 hours to obtain an ultraviolet curable resin (A-1). Was.
【００４３】 ［配合成分］ 紫外線硬化性樹脂（Ａ−１） ５５ 部 「イルガキュア９０７」（チバ・ガイギー社製光開始剤） ４ 部 「モダフロー」（モンサント社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 部 セロソルブアセテート ７．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (A-1) 55 parts "Irgacure 907" (photoinitiator manufactured by Ciba Geigy) 4 parts "Modaflow" (leveling agent manufactured by Monsanto) 0.5 part Colorant 12 parts "Swazol 1500" (aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts cellosolve acetate 7.5 parts ───────────────────────── 85 copies in total
【００４４】前記組成において、着色剤として先ず赤色
着色剤を用いた配合成分を三段ロールで混練し、希アル
カリ現像型の赤色感光性樹脂組成物を調製し、同ように
して、青色及び緑色着色剤を用いて青色及び緑色感光性
樹脂組成物を各々調製した。In the above composition, first, a compound using a red colorant as a colorant is kneaded with a three-stage roll to prepare a red alkali-developable red photosensitive resin composition. Blue and green photosensitive resin compositions were each prepared using a coloring agent.
【００４５】次に、上記赤色感光性樹脂組成物をプロピ
レングリコールモノメチルエーテルアセテートで３倍
（重量比）に希釈し、ガラス基板上にスピンコートによ
り全面塗布した後、溶剤を揮発させるために９０℃で乾
燥を２０分行ない、膜厚２μｍの乾燥塗膜を得た。その
後、パターンを描いたマスクを塗膜面に当てがい、５０
０ｍｊの紫外線を照射し、次に１％炭酸ナトリウム水溶
液を現像液として現像することによりパターンニングさ
れた赤色着色層を形成した。続いて、前記赤色着色層の
形成されたガラス基板上に、前記と同ようにして、青色
及び緑色の各感光性樹脂組成物を用いて青色着色層及び
緑色着色層を順次形成させ、カラーフィルタテストピー
スを作成した。Next, the above red photosensitive resin composition was diluted three times (weight ratio) with propylene glycol monomethyl ether acetate, and the whole was coated on a glass substrate by spin coating. For 20 minutes to obtain a dried coating film having a thickness of 2 μm. Then, a mask with a pattern is applied to the coating surface,
Irradiation with ultraviolet light of 0 mj was performed, and then development was performed using a 1% aqueous solution of sodium carbonate as a developer to form a patterned red colored layer. Subsequently, on the glass substrate on which the red coloring layer is formed, a blue coloring layer and a green coloring layer are sequentially formed using the blue and green photosensitive resin compositions in the same manner as described above, and a color filter is formed. A test piece was created.
【００４６】〔実施例２〕 ［配合成分］ 紫外線硬化性樹脂（Ａ−１） ４３ 部 トリメチロールプロパントリアクリレート ８ 部 「ルシリンＴＰＯ」（ＢＡＳＦ社製 光開始剤） ４ 部 「ポリフローＳ」（共栄社油脂社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 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 １１．５ 部 ────────────────────────────────── 合計 ８５ 部Example 2 [Components] 43 parts of ultraviolet curable resin (A-1) 8 parts of trimethylolpropane triacrylate 8 parts of “lucirin TPO” (photo initiator from BASF) 4 parts of “Polyflow S” (Kyoeisha) 0.5 part Coloring agent 12 parts "Swazol 1500" (Aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts Propylene glycol monomethyl ether acetate 11.5 parts合計 85 copies in total
【００４７】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００４８】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate in the same manner as in Example 1 using the photosensitive resin composition to prepare a color filter test piece.
【００４９】〔実施例３〕実施例１で用いた一般式（I
I）で表される化合物〔ＥＨＰＥ−３１５０ ダイセル
化学工業（株）社製 エポキシ当量 １８５〕１８５部
をカルビトールアセテート６０部に加熱溶解したもの
に、撹拌下にアクリル酸７４部、ハイドロキノン０．１
部及びベンジルジメチルアミン０．７部を加え、常法に
より９０〜１００℃で２４時間反応させた。この反応液
を冷却後、カルビトールアセテート６５部、スワゾール
１５００（丸善石油化学社製芳香族系溶剤）１３３部、
イソホロンジイソシアネート７部及びジブチルスズジラ
ウレート０．１部を加え、撹拌下に５０℃で４時間反応
させた。さらに、これにテトラヒドロ無水フタル酸７６
部を加え、１００℃に昇温すると共に撹拌下に約３時間
反応させ、紫外線硬化性樹脂（Ａ−２）を得た。Example 3 The general formula (I) used in Example 1 was used.
185 parts of a compound represented by the formula (I) [EHPE-3150, epoxy equivalent 185, manufactured by Daicel Chemical Industries, Ltd.] dissolved in 60 parts of carbitol acetate under heating was mixed with 74 parts of acrylic acid and hydroquinone 0.1 under stirring.
And 0.7 parts of benzyldimethylamine were added, and the mixture was reacted at 90 to 100 ° C. for 24 hours by a conventional method. After cooling the reaction solution, 65 parts of carbitol acetate, 133 parts of Swazole 1500 (an aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.),
7 parts of isophorone diisocyanate and 0.1 part of dibutyltin dilaurate were added and reacted at 50 ° C. for 4 hours with stirring. In addition, tetrahydrophthalic anhydride 76
Then, the mixture was heated to 100 ° C. and reacted with stirring for about 3 hours to obtain an ultraviolet curable resin (A-2).
【００５０】 ［配合成分］ 紫外線硬化性樹脂（Ａ−２） ５５ 部 ベンジルジメチルケタール ４ 部 「ＤＣ−３ＰＡ」（トーレシリコン社製） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 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 ７．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (A-2) 55 parts Benzyl dimethyl ketal 4 parts “DC-3PA” (manufactured by Toray Silicone) 0.5 part Colorant 12 parts “Swazol 1500” (Maruzen Petrochemical) (Aromatic solvent manufactured by Co.) 6 parts Propylene glycol monomethyl ether acetate 7.5 parts ──────────────────────────────── 85 copies in total
【００５１】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００５２】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate using the photosensitive resin composition in the same manner as in Example 1 to prepare a color filter test piece.
【００５３】〔実施例４〕実施例３においてイソホロン
ジイソシアネートの代わりにトリレンジイソシアネート
を用いたこと以外は、実施例３と同ように操作すること
により紫外線硬化性樹脂（Ａ−３）を得た。Example 4 An ultraviolet curable resin (A-3) was obtained in the same manner as in Example 3, except that tolylene diisocyanate was used instead of isophorone diisocyanate. .
【００５４】 ［配合成分］ 紫外線硬化性樹脂（Ａ−３） ４３ 部 ジペンタエリスリトールヘキサアクリレート ８ 部 ベンジルジメチルケタール ４ 部 「モダフロー」（モンサント社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 部 セロソルブアセテート １１．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (A-3) 43 parts Dipentaerythritol hexaacrylate 8 parts Benzyl dimethyl ketal 4 parts "Modaflow" (leveling agent manufactured by Monsanto) 0.5 part Colorant 12 parts "Swazol" 1500 "(Aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts Cellosolve Acetate 11.5 parts ───────────────────────────── 85 copies in total
【００５５】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００５６】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate in the same manner as in Example 1 by using the photosensitive resin composition to prepare a color filter test piece.
【００５７】〔実施例５〕実施例１で用いた一般式（I
I）で表される化合物〔ＥＨＰＥ−３１５０ ダイセル
化学工業（株）社製 エポキシ当量 １８５〕１３０部
及びエポトートＳＴ−３０００（東都化成社製水添ビス
フェノールＡ型エポキシ樹脂、エポキシ当量２３５）７
０．５部をカルビトールアセテート６５部に加熱溶解し
たものに、撹拌下にアクリル酸７４部、ハイドロキノン
０．１部及びベンジルジメチルアミン０．７部を加え、
常法により９０〜１００℃で２４時間反応させた。この
反応液を冷却後、カルビトールアセテート７０部、スワ
ゾール１５００（丸善石油化学社製芳香族系溶剤）１３
８部、イソホロンジイソシアネート１１部及びジブチル
スズジラウレート０．１部を加え、撹拌下に５０℃で４
時間反応させた。さらに、これにテトラヒドロ無水フタ
ル酸７６部を加え、１００℃に昇温すると共に撹拌下に
約３時間反応させ、紫外線硬化性樹脂（Ａ−４）を得
た。Example 5 The general formula (I) used in Example 1 was used.
130 parts of the compound represented by I) [EHPE-3150, epoxy equivalent 185, manufactured by Daicel Chemical Industries, Ltd.] and Epototo ST-3000 (hydrogenated bisphenol A type epoxy resin, epoxy equivalent 235, manufactured by Toto Kasei) 7
To a solution obtained by heating and dissolving 0.5 part of 65 parts of carbitol acetate, 74 parts of acrylic acid, 0.1 part of hydroquinone and 0.7 part of benzyldimethylamine were added with stirring.
The reaction was carried out at 90 to 100 ° C. for 24 hours by a conventional method. After cooling the reaction solution, 70 parts of carbitol acetate, 13 swazole 1500 (an aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 13
8 parts, 11 parts of isophorone diisocyanate and 0.1 part of dibutyltin dilaurate were added, and stirred at 50 ° C. for 4 hours.
Allowed to react for hours. Further, 76 parts of tetrahydrophthalic anhydride was added thereto, and the mixture was heated to 100 ° C. and reacted for about 3 hours with stirring to obtain an ultraviolet curable resin (A-4).
【００５８】 ［配合成分］ 紫外線硬化性樹脂（Ａ−４） ５５ 部 「イルガキュア９０７」 ４ 部 「モダフロー」（モンサント社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 部 セロソルブアセテート ７．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (A-4) 55 parts “Irgacure 907” 4 parts “Modaflow” (leveling agent manufactured by Monsanto) 0.5 part Colorant 12 parts “Swazol 1500” (Maruzen Petrochemical) Aromatic solvent manufactured by Sharp Corporation 6 parts Cellosolve Acetate 7.5 parts ────────────────────────────────── Total 85 copies
【００５９】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００６０】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate using the photosensitive resin composition in the same manner as in Example 1 to prepare a color filter test piece.
【００６１】〔実施例６〕 ［配合成分］ 紫外線硬化性樹脂（Ａ−２） ４３ 部 ヒドロキシエチルアクリレート ６ 部 「イルガキュアー９０７」（チバガイギー社製光重合開始剤） ４ 部 「ＴＥＰＩＣ」（日産化学社製エポキシ樹脂、エポキシ当量１００） ４ 部 「モダフロー」（モンサント社製レベリング剤） １ 部 着色剤 １２ 部 ２−メチルイミダゾール ０．１部 「スワゾール１５００」（丸善石油化学社製芳香 族系溶剤） ６ 部 ブチルグリコール ８．９部 ────────────────────────────────── 合計 ８５ 部Example 6 [Components] Ultraviolet-curable resin (A-2) 43 parts Hydroxyethyl acrylate 6 parts "Irgacure 907" (photopolymerization initiator manufactured by Ciba Geigy) 4 parts "TEPIC" (Nissan Chemical) Epoxy resin, epoxy equivalent 100) 4 parts "Modaflow" (leveling agent manufactured by Monsanto) 1 part Colorant 12 parts 2-methylimidazole 0.1 part "Swazol 1500" (Aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts butyl glycol 8.9 parts ８５ total 85 parts
【００６２】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００６３】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させた後、１５０℃で３０分
間加熱硬化を行い、カラーフィルタテストピースを作成
した。Next, a red coloring layer, a blue coloring layer, and a green coloring layer were formed on a glass substrate using the photosensitive resin composition in the same manner as in Example 1, and then heated at 150 ° C. for 30 minutes. After curing, a color filter test piece was prepared.
【００６４】〔実施例７〕下記の一般式で表される化合
物（III)〔ＥＨＰＥ−１１５０ ダイセル化学工業
（株）社製 エポキシ当量１７２〕Example 7 Compound (III) represented by the following general formula [EHPE-1150, epoxy equivalent 172, manufactured by Daicel Chemical Industries, Ltd.]
【００６５】[0065]
【化６】 Embedded image
【００６６】（式中、ｎは１０〜２０の整数である。）
１７２部をカルビトールアセテート６０部に加熱溶解し
たものに、撹拌下にアクリル酸７４部、ハイドロキノン
０．１部及びベンジルジメチルアミン０．７部を加え、
常法により９０〜１００℃で２４時間反応させた。この
反応液を冷却後、カルビトールアセテート６５部、スワ
ゾール１５００（丸善石油化学社製芳香族系溶剤）１１
８部及びテトラヒドロ無水フタル酸７６部を加え、１０
０℃に昇温すると共に撹拌下に約３時間反応させ、紫外
線硬化性樹脂（Ａ−５）を得た。(In the formula, n is an integer of 10 to 20.)
To a solution prepared by heating and dissolving 172 parts of carbitol acetate in 60 parts, 74 parts of acrylic acid, 0.1 part of hydroquinone and 0.7 parts of benzyldimethylamine were added with stirring.
The reaction was carried out at 90 to 100 ° C. for 24 hours by a conventional method. After cooling the reaction solution, 65 parts of carbitol acetate, swazole 1500 (aromatic solvent manufactured by Maruzen Petrochemical Co.) 11
8 parts and 76 parts of tetrahydrophthalic anhydride were added, and 10 parts were added.
The temperature was raised to 0 ° C., and the mixture was reacted for about 3 hours with stirring to obtain an ultraviolet curable resin (A-5).
【００６７】 ［配合成分］ 紫外線硬化性樹脂（Ａ−５） ５５ 部 「イルガキュア９０７」（チバ・ガイギー社製光開始剤） ４ 部 「モダフロー」（モンサント社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 部 セロソルブアセテート ７．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] Ultraviolet-curable resin (A-5) 55 parts “Irgacure 907” (photoinitiator manufactured by Ciba-Geigy) 4 parts “Modaflow” (leveling agent manufactured by Monsanto) 0.5 part Colorant 12 parts "Swazol 1500" (aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts cellosolve acetate 7.5 parts ───────────────────────── 85 copies in total
【００６８】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００６９】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate using the photosensitive resin composition in the same manner as in Example 1 to prepare a color filter test piece.
【００７０】〔実施例８〕実施例７で用いた一般式（II
I)で表される化合物〔ＥＨＰＥ−１１５０ ダイセル化
学工業（株）社製 エポキシ当量 １７２〕１７２部を
カルビトールアセテート６０部に加熱溶解したものに、
撹拌下にアクリル酸７４部、ハイドロキノン０．１部及
びベンジルジメチルアミン０．７部を加え、常法により
９０〜１００℃で２４時間反応させた。この反応液を冷
却後、カルビトールアセテート６５部、スワゾール１５
００（丸善石油化学社製芳香族系溶剤）１２３部、イソ
ホロンジイソシアネート７部及びジブチルスズジラウレ
ート０．１部を加え、撹拌下に５０℃で４時間反応させ
た。さらに、これにテトラヒドロ無水フタル酸７６部を
加え、１００℃に昇温すると共に撹拌下に約３時間反応
させ、紫外線硬化性樹脂（Ａ−６）を得た。Example 8 The general formula (II) used in Example 7
In a solution obtained by heating and dissolving 172 parts of a compound represented by I) [EHPE-1150, epoxy equivalent 172, manufactured by Daicel Chemical Industries, Ltd.] in 60 parts of carbitol acetate,
Under stirring, 74 parts of acrylic acid, 0.1 part of hydroquinone and 0.7 parts of benzyldimethylamine were added, and the mixture was reacted at 90 to 100 ° C. for 24 hours by a conventional method. After cooling the reaction mixture, 65 parts of carbitol acetate and 15 parts of swazole were used.
123 parts of 00 (aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.), 7 parts of isophorone diisocyanate and 0.1 part of dibutyltin dilaurate were added and reacted at 50 ° C. for 4 hours with stirring. Further, 76 parts of tetrahydrophthalic anhydride was added thereto, and the mixture was heated to 100 ° C. and reacted with stirring for about 3 hours to obtain an ultraviolet curable resin (A-6).
【００７１】 ［配合成分］ 紫外線硬化性樹脂（Ａ−３） ５５ 部 ベンジルジメチルケタール ４ 部 「ＤＣ−３ＰＡ」（トーレシリコン社製） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 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 ７．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (A-3) 55 parts Benzyl dimethyl ketal 4 parts “DC-3PA” (manufactured by Toray Silicone) 0.5 part Colorant 12 parts “Swazol 1500” (Maruzen Petrochemical) (Aromatic solvent manufactured by Co.) 6 parts Propylene glycol monomethyl ether acetate 7.5 parts ──────────────────────────────── 85 copies in total
【００７２】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００７３】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate in the same manner as in Example 1 by using the photosensitive resin composition to prepare a color filter test piece.
【００７４】〔比較例１〕ポリビニルアルコール（平均
重合度１７００、ケン化度８８モル％）に、アセタール
化反応によりＮ−メチル−４−（ｐ−ホルミルスチリ
ル）ピリジニウムメトサルフェートを付加して、反応液
を大量のアセトンに注加し、樹脂を沈澱させ、これをメ
タノールで充分に洗浄し、乾燥させ、スチリルピリジニ
ウム付加ポリビニルアルコール（１．２モル％付加）
（以下、「ＳＢＱ−ＰＶＡ」という」）を得た。Comparative Example 1 N-methyl-4- (p-formylstyryl) pyridinium methosulfate was added to polyvinyl alcohol (average degree of polymerization: 1700, saponification degree: 88 mol%) by an acetalization reaction. The solution was poured into a large amount of acetone to precipitate the resin, which was thoroughly washed with methanol, dried, and styrylpyridinium-added polyvinyl alcohol (1.2 mol% added).
(Hereinafter, referred to as “SBQ-PVA”) ”.
【００７５】このＳＢＱ−ＰＶＡ１００部に水９００部
を加え、常温で１時間撹拌し、ＳＢＱ−ＰＶＡの１０％
水溶液を調製した。To 100 parts of this SBQ-PVA, 900 parts of water was added, and the mixture was stirred at room temperature for 1 hour to obtain 10% of SBQ-PVA.
An aqueous solution was prepared.
【００７６】 ［配合成分］ ＳＢＱ−ＰＶＡ１０％水溶液 ７０ 部 水 ２７ 部 着色剤 ３ 部 ────────────────────────────────── 合計 １００ 部[Ingredients] SBQ-PVA 10% aqueous solution 70 parts Water 27 parts Colorant 3 parts １００ 100 copies in total
【００７７】前記組成において、着色剤として赤色着色
剤を用いた配合成分を三段ロールで混練し、ＳＢＱ−Ｐ
ＶＡ系の赤色感光性樹脂組成物を調製し、同様にして、
青色及び緑色着色剤を用いて青色及び緑色感光性樹脂組
成物を各々調製した。In the above composition, a compound using a red colorant as a colorant is kneaded with a three-stage roll, and the SBQ-P
A VA-based red photosensitive resin composition was prepared, and similarly,
Blue and green photosensitive resin compositions were prepared using blue and green colorants, respectively.
【００７８】赤色感光性樹脂組成物を、ガラス基板上に
スピンコートにより全面塗布し、水分を揮発させるため
に７０℃で乾燥を２０分行ない、膜厚２μｍの乾燥塗膜
を得た。その後、パターンを描いたマスクを塗膜面に当
てがい、３００ｍｊの紫外線を照射し、次に水／イソプ
ロパノール＝１０／３（重量比）を現像液として現像す
ることによりパターンニングされた赤色着色層を形成し
た。続いて、前記赤色着色層の形成されたガラス基板上
に、前記と同様にして、青色及び緑色の各感光性樹脂組
成物を用いて青色着色層及び緑色着色層を順次形成さ
せ、カラーフィルタテストピースを作成した。The red photosensitive resin composition was applied to the entire surface of a glass substrate by spin coating, and dried at 70 ° C. for 20 minutes in order to volatilize water, thereby obtaining a dried coating film having a thickness of 2 μm. Thereafter, a mask having a pattern drawn thereon is applied to the coating film surface, irradiated with 300 mj of ultraviolet light, and then developed using water / isopropanol = 10/3 (weight ratio) as a developer to form a patterned red colored layer. Was formed. Subsequently, on the glass substrate on which the red coloring layer was formed, a blue coloring layer and a green coloring layer were sequentially formed using the blue and green photosensitive resin compositions in the same manner as described above, and a color filter test was performed. Created a piece.
【００７９】〔比較例２〕エピコート１５４（油化シェ
ルエポキシ社製ノボラックエポキシ樹脂 エポキシ当量
１７８）１７８部をカルビトールアセテート６８部に加
熱溶解したものに、撹拌下にアクリル酸７４部、ハイド
ロキノン０．１部及びベンジルジメチルアミン０．７部
を加え、常法により９０〜１００℃で２４時間反応させ
た。この反応液を冷却後、カルビトールアセテート２０
部、スワゾール１５００（丸善石油化学社製芳香族系溶
剤）８８部及びテトラヒドロ無水フタル酸７６部を加
え、１００℃に昇温すると共に撹拌下に約３時間反応さ
せ、紫外線硬化性樹脂（Ｂ−２）を得た。Comparative Example 2 A mixture of 178 parts of Epicoat 154 (epoxy equivalent of novolak epoxy resin manufactured by Yuka Shell Epoxy Co., Ltd., 178) in 68 parts of carbitol acetate was heated to 74 parts of acrylic acid and 0.1 part of hydroquinone under stirring. 1 part and 0.7 parts of benzyldimethylamine were added, and the mixture was reacted at 90 to 100 ° C. for 24 hours by a conventional method. After cooling the reaction solution, carbitol acetate 20
, 88 parts of Swazol 1500 (aromatic solvent manufactured by Maruzen Petrochemical Co.) and 76 parts of tetrahydrophthalic anhydride, and the mixture was heated to 100 ° C. and reacted for about 3 hours with stirring. 2) was obtained.
【００８０】 ［配合成分］ 紫外線硬化性樹脂（Ｂ−２） ４３ 部 ジペンタエリスリトールヘキサアクリレート ８ 部 ベンジルジメチルケタール ４ 部 「モダフロー」（モンサント社製レベリング剤） ０．５ 部 着色剤 １２ 部 「スワゾール１５００」（丸善石油化学社製芳香族系溶剤） ６ 部 セロソルブアセテート １１．５ 部 ────────────────────────────────── 合計 ８５ 部[Ingredients] UV curable resin (B-2) 43 parts Dipentaerythritol hexaacrylate 8 parts Benzyl dimethyl ketal 4 parts "Modaflow" (leveling agent manufactured by Monsanto) 0.5 part Colorant 12 parts "Swazol" 1500 "(Aromatic solvent manufactured by Maruzen Petrochemical Co., Ltd.) 6 parts Cellosolve Acetate 11.5 parts ───────────────────────────── 85 copies in total
【００８１】前記組成の配合成分を実施例１と同じ方法
で混練し、赤色、青色及び緑色感光性樹脂組成物を各々
調製した。The components of the above composition were kneaded in the same manner as in Example 1 to prepare red, blue and green photosensitive resin compositions, respectively.
【００８２】次に、前記感光性樹脂組成物を用い、実施
例１と同じ方法で、ガラス基板上に赤色着色層、青色着
色層及び緑色着色層を形成させ、カラーフィルタテスト
ピースを作成した。Next, a red-colored layer, a blue-colored layer and a green-colored layer were formed on a glass substrate in the same manner as in Example 1 by using the photosensitive resin composition to prepare a color filter test piece.
【００８３】〈試験結果〉前記実施例及び比較例で得ら
れたテストピースに関する諸物性試験結果を表１、表２
及び表３に示す。<Test Results> Tables 1 and 2 show the results of various physical property tests on the test pieces obtained in the above Examples and Comparative Examples.
And Table 3.
【００８４】[0084]
【表１】 [Table 1]
【００８５】[0085]
【表２】 [Table 2]
【００８６】[0086]
【表３】 [Table 3]
【００８７】前記試験結果の評価方法は下記の通りであ
る。 ◎−−−極めて優れる。 ○−−−優れる。 △−−−やや劣る。 ×−−−劣る。The evaluation method of the test results is as follows. A --- Excellent. ○ ---- Excellent. Δ −−− Slightly inferior. X --- Inferior.
【００８８】[0088]
【発明の効果】以上のように、本発明に係るカラーフィ
ルタ用感光性樹脂組成物は、耐熱性に優れると共に２０
０℃以上の加熱によっても着色せず、しかも高解像性、
耐久性、耐光性及び耐薬品性に優れ、カラー液晶表示装
置等のカラーフィルタの製造に好適に使用できる。As described above, the color filter according to the present invention is
The photosensitive resin composition for filter has excellent heat resistance and 20
No coloration by heating at 0 ° C or higher, and high resolution.
It has excellent durability, light resistance and chemical resistance, and can be suitably used for the production of color filters for color liquid crystal display devices and the like.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｇ０３Ｆ 7/027 ５０２ Ｇ０３Ｆ 7/027 ５０２ ５１３ ５１３ 7/028 7/028 7/032 ５０１ 7/032 ５０１ (56)参考文献 特開 平４−170547（ＪＰ，Ａ) 特開 平４−194942（ＪＰ，Ａ) 特開 平２−173749（ＪＰ，Ａ) 特開 平３−100009（ＪＰ，Ａ) 特開 昭63−278052（ＪＰ，Ａ) 特開 昭49−2601（ＪＰ，Ａ) 特開 昭60−170620（ＪＰ，Ａ) 特開 昭60−161973（ＪＰ，Ａ) 特開 昭63−251416（ＪＰ，Ａ) 特開 昭61−272（ＪＰ，Ａ) 特開 昭63−296037（ＪＰ，Ａ) 特開 平６−93221（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) G03F 7/038 C08F 2/50 G02B 5/20 101 G03F 7/004 G03F 7/027 G03F 7/028 G03F 7/032 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification code FI G03F 7/027 502 G03F 7/027 502 513 513 7/028 7/028 7/032 501 7/032 501 (56) References Special features Japanese Unexamined Patent Publication (Kokai) No. 4-170547 (JP, A) Japanese Unexamined Patent Publication (Kokai) No. 4-194942 (JP, A) Japanese Unexamined Patent Publication (Kokai) No. 2-173749 (JP, A) JP, A) JP-A-49-2601 (JP, A) JP-A-60-170620 (JP, A) JP-A-60-161973 (JP, A) JP-A-63-251416 (JP, A) JP-A-61-272 (JP, A) JP-A-63-296037 (JP, A) JP-A-6-93221 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) G03F 7 / 038 C08F 2/50 G02B 5/20 101 G03F 7/004 G03F 7/027 G03F 7/028 G03F 7/032
Claims (5)
物と不飽和モノカルボン酸との反応物に飽和若しくは不
飽和多塩基酸無水物を反応させて得られる紫外線硬化性
樹脂、 【化１】 〔但し、式中、Ｒはｋ個の活性水素を有する有機化合物
残基、ｎ1 、ｎ2 、ｎ k は０又は１〜５０の整数で、そ
の和が１〜５０であり、ｋは１〜３の整数である。ま
た、式中の下記官能基 【化２】 （但し、Ｒ’は水素原子、アルキル基、アルキルカルボ
ニル基又はアリールカルボニル基を示す）に置き換えて
もよい。〕 Ｂ．光重合開始剤、 Ｃ．希釈剤及び Ｄ．着色剤 を含んでなる、希アルカリ水溶液で現像可能なカラーフ
ィルタ用感光性樹脂組成物。1. A. First Embodiment An ultraviolet-curable resin obtained by reacting a reaction product of a compound represented by the following general formula (I) with an unsaturated monocarboxylic acid with a saturated or unsaturated polybasic acid anhydride: Wherein R is an organic compound residue having k active hydrogens, n 1 , n 2 and nk are 0 or an integer of 1 to 50, the sum of which is 1 to 50 , and k is 1 -3 . Further, the following functional group in the formula: (However, R ′ represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an arylcarbonyl group). B. A photopolymerization initiator, C.I. Diluent and D. A color film that can be developed with a dilute alkaline aqueous solution and contains a colorant.
A photosensitive resin composition for filters .
飽和モノカルボン酸との反応物に、イソシアネート基を
分子中に少なくとも２個有する化合物及び飽和若しくは
不飽和多塩基酸無水物を反応させて得られる紫外線硬化
性樹脂、 Ｂ．光重合開始剤、 Ｃ．希釈剤及び Ｄ．着色剤 を含んでなる、希アルカリ水溶液で現像可能なカラーフ
ィルタ用感光性樹脂組成物。2. A. Ultraviolet light obtained by reacting a reaction product of the compound represented by the general formula (I) with an unsaturated monocarboxylic acid with a compound having at least two isocyanate groups in the molecule and a saturated or unsaturated polybasic anhydride. Curable resin, B. A photopolymerization initiator, C.I. Diluent and D. A color film that can be developed with a dilute alkaline aqueous solution and contains a colorant.
A photosensitive resin composition for filters .
表される化合物と不飽和モノカルボン酸との反応物の代
わりに一般式（Ｉ）で表される化合物及びその他のエポ
キシ化合物と不飽和モノカルボン酸との反応物が用いら
れた請求項１又は請求項２記載のカラーフィルタ用感光
性樹脂組成物。3. In the synthesis of the component A, a compound represented by the general formula (I) and another epoxy compound are used instead of a reaction product of the compound represented by the general formula (I) and the unsaturated monocarboxylic acid. The photosensitive resin composition for a color filter according to claim 1 or 2, wherein a reaction product with an unsaturated monocarboxylic acid is used.
求項２又は請求項３記載のカラーフィルタ用感光性樹脂
組成物。4. E. The photosensitive resin composition for a color filter according to claim 1, which comprises a thermosetting compound.
求項４記載の感光性樹脂組成物を用いて製造されたカラ
ーフィルタ。5. A color filter produced using the photosensitive resin composition according to claim 1, 2, 3, or 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27809092A JP3016532B2 (en) | 1992-09-21 | 1992-09-21 | Photosensitive resin composition for color filter and color filter using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27809092A JP3016532B2 (en) | 1992-09-21 | 1992-09-21 | Photosensitive resin composition for color filter and color filter using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06102669A JPH06102669A (en) | 1994-04-15 |
| JP3016532B2 true JP3016532B2 (en) | 2000-03-06 |
Family
ID=17592501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27809092A Expired - Fee Related JP3016532B2 (en) | 1992-09-21 | 1992-09-21 | Photosensitive resin composition for color filter and color filter using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3016532B2 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5615129A (en) * | 1995-02-21 | 1997-03-25 | General Signal Power Systems, Inc. | Method and apparatus for adaptive and corrective determination of battery run-time in uninterruptible power systems |
| JP3743490B2 (en) * | 2000-02-16 | 2006-02-08 | 信越化学工業株式会社 | Thermosetting photosensitive material |
| JP2003122001A (en) * | 2001-10-15 | 2003-04-25 | Nippon Kayaku Co Ltd | Photosensitive resin, photosensitive resin composition using the same, and its hardened product |
| JP4594851B2 (en) * | 2005-11-25 | 2010-12-08 | 株式会社東芝 | Resin composition and resin-encapsulated semiconductor device |
| JP5286657B2 (en) * | 2006-09-22 | 2013-09-11 | 大日本印刷株式会社 | Pigment dispersion, inkjet ink for color filter and method for producing the same, color filter, and liquid crystal display device |
| JP5211701B2 (en) * | 2008-01-10 | 2013-06-12 | 大日本印刷株式会社 | Cyclic ether compound for photocurable resin composition |
| JP5371449B2 (en) | 2008-01-31 | 2013-12-18 | 富士フイルム株式会社 | Resin, pigment dispersion, colored curable composition, color filter using the same, and method for producing the same |
| JP5334624B2 (en) | 2008-03-17 | 2013-11-06 | 富士フイルム株式会社 | Colored curable composition, color filter, and method for producing color filter |
| KR101441998B1 (en) | 2008-04-25 | 2014-09-18 | 후지필름 가부시키가이샤 | Polymerizable composition, light shielding color filter, black curable composition, light shielding color filter for solid-state imaging device, method of manufacturing the same, and solid-state imaging device |
| JP2010198735A (en) | 2009-02-20 | 2010-09-09 | Fujifilm Corp | Optical member and organic electroluminescent display device equipped with the same |
| JP5535692B2 (en) * | 2009-03-17 | 2014-07-02 | 富士フイルム株式会社 | Colored curable composition, color filter, and method for producing color filter |
| JP2016027400A (en) * | 2014-07-04 | 2016-02-18 | 株式会社日本触媒 | Resin composition for lamination and intended purposes thereof |
-
1992
- 1992-09-21 JP JP27809092A patent/JP3016532B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06102669A (en) | 1994-04-15 |
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