JP6844121B2 - 着色硬化性樹脂組成物及びその硬化膜 - Google Patents
着色硬化性樹脂組成物及びその硬化膜 Download PDFInfo
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- JP6844121B2 JP6844121B2 JP2016085281A JP2016085281A JP6844121B2 JP 6844121 B2 JP6844121 B2 JP 6844121B2 JP 2016085281 A JP2016085281 A JP 2016085281A JP 2016085281 A JP2016085281 A JP 2016085281A JP 6844121 B2 JP6844121 B2 JP 6844121B2
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- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical class CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- WCAOBJJSISYNMN-UHFFFAOYSA-N oxetane;terephthalic acid Chemical compound C1COC1.C1COC1.OC(=O)C1=CC=C(C(O)=O)C=C1 WCAOBJJSISYNMN-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- KGOFMNHNVFEEHB-UHFFFAOYSA-N prop-2-enoyloxymethoxymethyl prop-2-enoate Chemical compound C=CC(=O)OCOCOC(=O)C=C KGOFMNHNVFEEHB-UHFFFAOYSA-N 0.000 description 1
- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- ZQMAPKVSTSACQB-UHFFFAOYSA-N prop-2-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC=C ZQMAPKVSTSACQB-UHFFFAOYSA-N 0.000 description 1
- HAFZJTKIBGEQKT-UHFFFAOYSA-N prop-2-enyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC=C HAFZJTKIBGEQKT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UOUAODFZKFGFKS-UHFFFAOYSA-N propane-1-sulfonic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCS(O)(=O)=O UOUAODFZKFGFKS-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- FTUYQIPAPWPHNC-UHFFFAOYSA-M sodium;4-[[4-[benzyl(ethyl)amino]phenyl]-[4-[benzyl(ethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 FTUYQIPAPWPHNC-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YEOUFHBJWTZWCZ-UHFFFAOYSA-M sulforhodamine G Chemical compound [Na+].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O YEOUFHBJWTZWCZ-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
- 229960004453 trimethadione Drugs 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical class CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- JBCJMTUHAXHILC-UHFFFAOYSA-N zinc;octanoic acid Chemical compound [Zn+2].CCCCCCCC(O)=O JBCJMTUHAXHILC-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Description
で表される熱分解性基を有する含フッ素熱分解性界面活性剤(A)、着色剤(B)、アルカリ可溶性樹脂(C)、前記アルカリ可溶性樹脂(C)以外の光硬化性化合物(D)、光重合開始剤(E)および溶剤(F)を含有することを特徴とする着色硬化性樹脂組成物を提供するものである。
で表される熱分解性基を有することを特徴とする。
で表される構造単位を有する樹脂であることが好ましい。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:RI
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
で表される基であり、R62、R63はそれぞれ前記構造式(a1)で表される基又はカルボキシル基である。〕
で表される構造単位を有する、カルボキシル基を有する樹脂(但し、カルボキシル基を有する樹脂中のフッ素原子含有率は0.5質量%以下である。)となる。
製法1:カルボキシル基を有する重合性単量体(α)と、下記一般式(1)
で表されるビニルエーテル化合物と、を反応させてブロック化されたカルボキシル基を有する重合性単量体を得た後、該重合性単量体を重合させる方法。
R5は、−OH、−SO3−、−SO3H、−SO3 −M+、−CO2H、−CO2 −M+、−CO2R8、−SO3R8又は−SO2NR9R10であり、mは0〜5の整数を表し、(但し、mが2以上の整数である場合、複数のR5は同一であっても、異なっていてもよい。)
R6及びR7は、それぞれ独立に、炭素数1〜6のアルキル基である。
Xは、ハロゲン原子であり、a1は、0又は1の整数であり、
R25は、−SO3−、−SO3 −Ma+、−SO3H又はSO2NHR26であり、m1は、0〜5の整数(但し、m1が2以上の整数である場合、複数のR25は同一であっても異なっていてもよい)である。
・酸性基を有する(メタ)アクリル系重合性単量体を必須の成分として重合させて得られるアルカリ可溶性樹脂(C1)。
・反応性基を持つ(メタ)アクリル系重合性単量体を必須の成分として重合させて得られる酸性基を有さない重合体と、該反応性基に対して反応性を有する反応性基と酸基とを有する化合物とを反応させて得られるアルカリ可溶性樹脂(C2)
・エポキシ基含有(メタ)アクリレートと、他の重合性単量体との共重合体に対し、該共重合体が有するエポキシ基の少なくとも一部に不飽和モノカルボン酸を付加させ、さらに不飽和モノカルボン酸の付加反応により生じた水酸基の少なくとも一部にポリカルボン酸の酸無水物を付加反応させて得られるアルカリ可溶性樹脂(C3)。
・カルボキシル基と重合性不飽和基を有するエポキシ(メタ)アクリレート樹脂(C4)
・カルボキシル基と重合性不飽和基を有するカルド型樹脂(C5)
以下に、上記(C1)〜(C5)について詳細に説明する。
・2−ヒドロキシエチル(メタ)アクリレートのような水酸基を有する重合性単量体を必須の成分として重合体を得た後、コハク酸無水物、テトラヒドロフタル酸無水物、マレイン酸無水物等の酸無水物を付加させて得られるアルカリ可溶性樹脂。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
攪拌機、温度計、冷却管および窒素導入管を装備した4つ口フラスコに、プロピレングリコールモノメチルエーテルアセテート100gを仕込み、窒素気流下、攪拌しながら内温を110℃に昇温した。次いで、ベンジルメタクリレート80gとメタクリル酸20gからなる混合液と、プロピレングリコールモノメチルエーテルアセテート46g、t−アミルパーオキシ−2−エチルヘキサノエート1.5g及びt−アミルパーベンゾエート0.15gからなる混合液をそれぞれ4時間かけて滴下した。滴下終了後、内温を110℃に保持したまま8時間重合反応させた。反応終了後、プロピレングリコールモノメチルエーテルアセテートにて希釈し、不揮発分40%のアルカリ可溶性樹脂(C1)の樹脂溶液を得た。この樹脂の重量平均分子量は17,000であった。
500ml四つ口フラスコ中に、ビスフェノールフルオレン型エポキシ樹脂(エポキシ当量235)235g、テトラメチルアンモニウムクロライド110mg、2,6−ジ−tert−ブチル−4−メチルフェノール100mg及びアクリル酸72.0gを仕込み、これに25ml/分の速度で空気を吹き込みながら90〜100℃で加熱溶解した。次に、溶液が白濁した状態のまま徐々に昇温し、120℃に加熱して完全溶解させた。この際、溶液は次第に透明粘稠になったが、そのまま撹拌を継続した。この間、酸価を測定し、1.0mgKOH/g未満になるまで加熱撹拌を続けた。酸価が目標値に達するまで12時間を要した。そして室温まで冷却し、無色透明で固体状の下記式(a4)で表されるビスフェノールフルオレン型エポキシアクリレートを得た。
得られた含フッ素熱分解性界面活性剤(A1)を用いて硬化膜を作製し、その外見を評価した。具体的には、アルカリ可溶性樹脂(C1)の40質量%樹脂溶液を3部、光重合性モノマーとして東亞合成株式会社製アロニックスM−402 1.2部、光重合開始剤としてBASFジャパン株式会社製イルガキュア#369 0.1部、含フッ素熱分解性界面活性剤(A1)を固形分として換算で0.0024部を、プロピレングリコールモノメチルエーテルアセテート(PGMEA)8部に混合して、光硬化型樹脂組成物を調製した。得られた光硬化型樹脂組成物を用いて硬化膜を得て、その外観を評価した。硬化膜の作製方法及び評価方法を下記に示す。
光硬化型樹脂組成物3mlを10cm×10cmのクロムメッキガラス基板に回転数500rpmで30秒間スピンコーティングした後、110℃で2分間加熱乾燥させて塗膜を作製した。
硬化膜にナトリウムランプを照射して硬化膜表面の凹凸(塗布ムラ)の発生具合を目視で観察し、以下の判断基準で硬化膜表面の平滑性を評価した。
○:塗布ムラがほとんど観察されない。
△:塗布ムラが一部観察される。
×:塗布ムラが多く観測される。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A2)を用いた以外は試験例1と同様にして硬化膜を得て、その外観を評価した。上記の基準によると、硬化膜の外見の評価は「○:塗布ムラがほとんど観察されない。」であった。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A3)を用いた以外は試験例1と同様にして硬化膜を得て、その外観を評価した。上記の基準によると、硬化膜の外見の評価は「○:塗布ムラがほとんど観察されない。」であった。
含フッ素熱分解性界面活性剤(A1)の代わりに、含フッ素非熱分解性界面活性剤(A´1)(DIC株式会社製のフッ素系界面活性剤 メガファックF−560)を用いた以外は試験例1と同様にして比較対照用光硬化型樹脂組成物(1´)を得た。試験例1と同様にして硬化膜の外見の評価は「○:塗布ムラがほとんど観察されない。」であった。
<赤色顔料分散液の調整>
C.I.PigmentRed254(BASF社製「IRGAPHOR RED BT−CF」)10gをポリビンに入れ、PGMEA 60g、DISPERBYK LPN21116(ビックケミー株式会社製)12g、0.3−0.4mmΦセプルビーズを加え、ペイントコンディショナー(東洋精機株式会社製)で2時間分散し、赤色顔料分散液を得た。
この赤色顔料分散液5.9gに対し、含フッ素熱分解性界面活性剤(A)として、前記含フッ素熱分解性界面活性剤(A1)を固形分換算で0.0023g、アルカリ可溶性樹脂(C)としてアルカリ可溶性樹脂(C1)の40質量%樹脂溶液を1.5g、光硬化性化合物(D)として東亞合成化学株式会社製アロニックスM−402を0.6g、光重合開始剤(E)としてBASFジャパン株式会社製イルガキュア#369を0.05g、溶剤(F)としてPGMEAを2.2g加え混合し、本発明の着色硬化性組成物(1)を得た。得られた着色硬化性組成物(1)を用いて硬化膜を得て、硬化膜へのリコート性を評価した。硬化膜の作製方法及び評価方法を下記に示す。評価結果を第1表に示す。
着色硬化性組成物(1)を7cm×7cmのガラス板上に回転数1000rpmで10秒間スピンコーティングした後、高圧水銀灯で50mJ/cm2の条件で露光して硬化膜を作製した。
硬化膜表面の極性の変化を測定し、リコート性の評価とした。具体的には、硬化膜を230℃の乾燥機を用いて20分間加熱し、その前後でのPGMEAの接触角を測定した。加熱後の接触角が小さい程、リコート性に優れる硬化膜が得られたと判断した。更に硬化膜を大気圧プラズマにて処理した後、再度硬化膜表面のPGMEA接触角を測定した。接触角が20°未満である場合、リコート性に優れると評価した。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A2)を用いた以外は実施例1と同様にして着色硬化性組成物(2)を得た。得られた着色硬化性組成物(2)を用いて硬化膜を得て、実施例1と同様にして硬化膜へのリコート性を評価した。評価結果を第1表に示す。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A3)を用いた以外は実施例1と同様にして着色硬化性組成物(3)を得た。得られた着色硬化性組成物(3)を用いて硬化膜を得て、実施例1と同様にして硬化膜へのリコート性を評価した。評価結果を第1表に示す。
<青色顔料分散液の調製>
C.I.PigmentBlue15:6(DIC社製「FASTOGEN Blue A510」)12gをポリビンに入れ、PGMEA 82g、EFKA4320(BASF株式会社製)6g、0.3−0.4mmΦセプルビーズを加え、ペイントコンディショナーで2時間分散し、青色顔料分散液を得た。
この青色顔料分散液4.2gに対し、前記含フッ素熱分解性界面活性剤(A1)を固形分換算で0.001g、染料(b2)としてキサンテン系染料(山田化学工業製 CFB−2)を0.1g、アルカリ可溶性樹脂(C)として合成例2で得たアルカリ可溶性樹脂(C1)の40質量%樹脂溶液を1.5g、光硬化性化合物(D)として東亞合成化学株式会社製アロニックスM−402を0.6g、光重合開始剤(E)としてBASFジャパン株式会社製イルガキュア#369を0.05g、溶剤(F)としてPGMEAを3.7g加え混合し、本発明の着色硬化性組成物(2)を得た。実施例1と同様にして硬化膜を得て、硬化膜へのリコート性を評価した。評価結果を第2表に示す。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A2)を用いた以外は実施例4と同様にして着色硬化性組成物(2)を得た。得られた着色硬化性組成物(2)を用いて硬化膜を得て、実施例4と同様にして硬化膜へのリコート性を評価した。評価結果を第2表に示す。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A3)を用いた以外は実施例4と同様にして着色硬化性組成物(3)を得た。得られた着色硬化性組成物(3)を用いて硬化膜を得て、実施例4と同様にして硬化膜へのリコート性を評価した。評価結果を第2表に示す。
<カーボンブラックインクの調製>
カーボンブラック(三菱化学社製#2400)100g、BYK167(ビックケミー株式会社製)20g(固形分換算)、S12000(ルーブリゾール社製)2g及びPGMEA 232.8gを混合し、十分に撹拌し、混合液を得た。混合液をペイントシェーカーに入れ、30℃で6時間分散処理を行った。分散処理の際には混合液60gに対して直径0.5mmのジルコニアビーズ180gを用いた。分散終了後、フィルターによりビーズと分散液を分離して、固形分35%のカーボンブラックインクを調製した。このカ−ボンブラックインクは増粘もなく分散性が良好であった。
アルカリ可溶性樹脂(C)としてカルド樹脂(C2)に3−メトキシブチルアセテートを加え、固形分濃度50質量%に調整した調整液を得た。この調整液25部、光硬化性化合物(D)としてジペンタエリスリトールヘキサアクリレートを9部、光重合開始剤(E)としてBASFジャパン株式会社製イルガキュアOXE02を6.7部、イルガキュア#369を3.3部、含フッ素熱分解性界面活性剤(A1)を固形分換算で0.2部、カーボンブラックインキを157部及びPGMEAを加えて固形分濃度を15質量%に調整し、撹拌機で2時間混合した後、5μmメンブレンフィルターで濾過し、着色硬化性組成物(3)を調製した。
着色硬化性組成物(3)を7cm×7cmのガラス板上に回転数1000rpmで10秒間スピンコーティングした後、80℃で3分間乾燥させた。乾燥後、高圧水銀灯を使用して50mJ/cm2で露光して硬化膜を作製した。
実施例1と同様にして硬化膜へのリコート性を評価するとともに、更に硬化膜を大気圧プラズマにて処理した後、再度硬化膜表面のPGMEA接触角を測定した。評価結果を第3表に示す。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A2)を用いた以外は実施例7と同様にして着色硬化性組成物(2)を得た。得られた着色硬化性組成物(2)を用いて硬化膜を得て、実施例7と同様にして硬化膜へのリコート性を評価した。評価結果を第3表に示す。
含フッ素熱分解性界面活性剤(A1)のかわりに含フッ素熱分解性界面活性剤(A3)を用いた以外は実施例7と同様にして着色硬化性組成物(3)を得た。得られた着色硬化性組成物(3)を用いて硬化膜を得て、実施例7と同様にして硬化膜へのリコート性を評価した。評価結果を第3表に示す。
含フッ素熱分解性界面活性剤(A1)の代わりに含フッ素非熱分解性界面活性剤(A´1)を用いた以外は実施例1と同様にして比較対照用着色硬化性樹脂組成物(1´)を得た。実施例1と同様にして硬化膜を得て、硬化膜へのリコート性を評価した。評価結果を第1表に示す。
含フッ素熱分解性界面活性剤(A1)の代わりに含フッ素非熱分解性界面活性剤(A´1)を用いた以外は実施例4と同様にして比較対照用着色硬化性樹脂組成物(2´)を得た。実施例4と同様にして硬化膜を得て、硬化膜へのリコート性を評価した。評価結果を第2表に示す。
含フッ素熱分解性界面活性剤(A1)の代わりに含フッ素非熱分解性界面活性剤(A´2)(DIC株式会社製のフッ素系界面活性剤 メガファックF−559)を用いた以外は実施例7と同様にして比較対照用着色硬化性樹脂組成物(3´)を得た。実施例7と同様にして硬化膜を得て、硬化膜へのリコート性を評価した。評価結果を第3表に示す。
Claims (11)
- 下記構造式(a1)
で表される熱分解性基を有する樹脂である含フッ素熱分解性界面活性剤(A)、着色剤(B)、アルカリ可溶性樹脂(C)、前記アルカリ可溶性樹脂(C)以外の光硬化性化合物(D)、光重合開始剤(E)および溶剤(F)を含有することを特徴とするブラックマトリックス用着色硬化性樹脂組成物。但し、前記構造式(a1)で表される熱分解性基を有する樹脂は、ゲルパーミエーションクロマトグラフィー(カラムの種類:TSK gel Super(東ソー)、展開溶媒:テトラヒドロフラン、カラム温度:40℃、流量(サンプル注入量):10μl、装置名: HLC−8220GPC(東ソー)、検量線ベース樹脂:ポリスチレン樹脂)で測定して得られる重量平均分子量で1900、2600、3200、5500及び12000であるものを除く。 - 前記構造式(a1)中のR4が、フッ素原子が直接結合した炭素原子の数が1〜6のフッ素化アルキル基である請求項1記載の着色硬化性樹脂組成物。
- 前記構造式(a1)中のR4が、フッ素原子が直接結合した炭素原子の数が4〜6のフッ素化アルキル基である請求項1記載の着色硬化性樹脂組成物。
- 前記構造式(a1)中のR1、R2およびR3がそれぞれ水素原子で、R4がフッ素原子が直接結合した炭素原子の数が1〜6のフッ素化アルキル基である請求項1記載の着色硬化性樹脂組成物。
- 前記含フッ素熱分解性界面活性剤(A)のフッ素原子含有率が1〜35質量%である請求項1記載の着色硬化性樹脂組成物。
- 前記含フッ素熱分解性界面活性剤(A)が、カルボキシル基を有する重合性単量体(α)を原料とする重合体と、前記一般式(1)で表されるビニルエーテル化合物と、を構成要素とするものである請求項1記載の着色硬化性樹脂組成物。
- 請求項1〜9のいずれか1項記載の着色硬化性樹脂組成物の硬化膜であるブラックマトリックス。
- 下記構造式(a1)
で表される熱分解性基を有する樹脂である含フッ素熱分解性界面活性剤(A)、着色剤(B)、アルカリ可溶性樹脂(C)、前記アルカリ可溶性樹脂(C)以外の光硬化性化合物(D)、光重合開始剤(E)および溶剤(F)を含有する着色硬化性樹脂組成物の硬化膜であるカラーフィルター。但し、前記構造式(a1)で表される熱分解性基を有する樹脂は、ゲルパーミエーションクロマトグラフィー(カラムの種類:TSK gel Super(東ソー)、展開溶媒:テトラヒドロフラン、カラム温度:40℃、流量(サンプル注入量):10μl、装置名: HLC−8220GPC(東ソー)、検量線ベース樹脂:ポリスチレン樹脂)で測定して得られる重量平均分子量で1900、2600、3200、5500及び12000であるものを除く。
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