JP2019183020A - 重合性組成物、ブラックマトリクス用感光性組成物及びカラーフィルタ - Google Patents
重合性組成物、ブラックマトリクス用感光性組成物及びカラーフィルタ Download PDFInfo
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- JP2019183020A JP2019183020A JP2018076450A JP2018076450A JP2019183020A JP 2019183020 A JP2019183020 A JP 2019183020A JP 2018076450 A JP2018076450 A JP 2018076450A JP 2018076450 A JP2018076450 A JP 2018076450A JP 2019183020 A JP2019183020 A JP 2019183020A
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- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 239000011159 matrix material Substances 0.000 title description 15
- -1 isocyanate silane compound Chemical class 0.000 claims abstract description 275
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000012948 isocyanate Substances 0.000 claims abstract description 25
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 21
- 239000002981 blocking agent Substances 0.000 claims abstract description 18
- 239000003086 colorant Substances 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 239000004593 Epoxy Substances 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 23
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
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- 229910052799 carbon Inorganic materials 0.000 claims description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 239000003999 initiator Substances 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
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- 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 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229940049920 malate Drugs 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 5
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 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 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
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- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- QPKSOTIQSGGKOB-UHFFFAOYSA-N n,n-diamino-1-(oxiran-2-yl)methanamine Chemical class NN(N)CC1CO1 QPKSOTIQSGGKOB-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-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
- 239000002116 nanohorn Substances 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
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- 239000002736 nonionic surfactant Substances 0.000 description 1
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- 239000004843 novolac epoxy resin Substances 0.000 description 1
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- YLNSNVGRSIOCEU-UHFFFAOYSA-N oxiran-2-ylmethyl butanoate Chemical compound CCCC(=O)OCC1CO1 YLNSNVGRSIOCEU-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 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
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 150000003953 γ-lactams Chemical class 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Optical Filters (AREA)
Abstract
Description
上記BM用感光性組成物において顔料を用いる場合、感光性組成物を調製する際に、顔料を予め樹脂や分散媒に分散させた顔料分散液を作成することが一般的である。
R2は、水素原子、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、
Z1は、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、Z1で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR4−、−NR4CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
R4は、水素原子、炭素原子数1〜20の炭化水素基を表し、
aは1〜3の数を表し、a≧2の場合、複数存在するR1は同一である場合があり、異なる場合があり、
bは0〜2の数を表し、b=2の場合、複数存在するR2は、同一である場合があり、異なる場合があり、
a+b=3である。)
R3は、水素原子又はメチル基を表し、
X1及びX3は、それぞれ独立に、直接結合又は炭素原子数1〜20の炭化水素基を表し、
X2は、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、
X1、X2及びX3で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR4−、−NR4CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
Yは、酸素原子、硫黄原子、又は−NR4−を表し、
R4は、水素原子、炭素原子数1〜20の炭化水素基を表し、
cは、2〜10の数を表し、
c≧2の場合、複数存在するR3は、同一の場合があり異なる場合があり、
dは、1〜3の数を表し、
d≧2の場合、R1、R2、X3及びZ1は、それぞれ、同一の場合があり異なる場合がある。)
下記一般式(IV)で表されるエポキシ化合物、
下記一般式(IV)で表されるエポキシ化合物と不飽和一塩基酸とをエステル化させた構造を有する不飽和化合物、又は
下記一般式(IV)で表されるエポキシ化合物と不飽和一塩基酸とをエステル化させた構造を有する不飽和化合物に、更に多塩基酸無水物をエステル化させた構造を有する不飽和化合物
である[1]〜[3]の何れか一に記載の重合性組成物。
Mで表される炭素原子数1〜20の炭化水素基中の1つ又は2つ以上の水素原子はハロゲン原子で置換される場合があり、
R11、R12、R13、R14、R15、R16、R17及びR18は、それぞれ独立に、水素原子、炭素原子数1〜20の炭化水素基又はハロゲン原子を表し、
R11〜R18で表される基中のメチレン基は、酸素が隣り合わない条件で、−O−に置換されている場合があり、
nは0〜10の数を表し、
nが0でない場合、複数存在するR11、R12、R13、R14、R15、R16、R17、R18及びMは、それぞれ、同一である場合があり、異なる場合がある。)
R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49及びR50は、それぞれ独立に、水素原子、炭素原子数1〜20の炭化水素基、複素環を含有する炭素原子数2〜20の基、又はハロゲン原子を表し、
R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49及びR50で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−又は−S−に置換される場合があり、
R22とR23、R23とR24、R24とR25、R25とR26、R27とR28、R28とR29、R29とR30、R35とR36、R36とR37、R37とR38、R43とR44、R44とR45、R45とR46、R47とR48、R48とR49及びR49とR50は結合して環を形成する場合があり、
式中の*は、(a)、(b)、(c)及び(d)で表される基が、*部分で隣接する基と結合することを意味する。)
R61及びR62で表される基中の水素原子の1つ又は2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環を含有する炭素原子数2〜20の基で置換されている場合があり、
R61及びR62で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR63−、−NR63CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
R63は、水素原子又は炭素原子数1〜20の炭化水素基を表し、
mは0又は1を表し、
式中の*は、一般式(V)で表される基が、*部分で、隣接する基と結合することを意味する。)
ブロックイソシアネートシラン化合物(A)は、上記一般式(I)で表されるイソシアネート化合物とブロック化剤とを反応させて得られた構造を有する化合物である。
チル、エチル、プロピル、iso−プロピル、ブチル、sec−ブチル、tert−ブチル、iso−ブチル、アミル、iso−アミル、tert−アミル、ヘキシル、2−ヘキシル、3−ヘキシル、シクロヘキシル、1−メチルシクロヘキシル、ヘプチル、2−ヘプチル、3−ヘプチル、iso−ヘプチル、tert−ヘプチル、1−オクチル、iso−オクチル、tert−オクチル等が挙げられる。
また、上記一般式(I)において、aが3であり、且つbが0であるイソシアネート化合物が、密着性の点から好ましい。
本発明の重合性組成物は重合性化合物(B)を含有する。
重合性化合物(B)としては、光硬化性樹脂及び/又は熱硬化性樹脂を用いることができる(但し、上記ブロックイソシアネートシラン化合物(A)を除く)。
光硬化性樹脂としては、アクリル酸エステルの重合体;エポキシ樹脂に不飽和一塩基酸を反応させて得られるもの;エポキシ樹脂と不飽和一塩基酸との反応物に、更に多塩基酸無水物を反応させて得られるもの;テトラカルボン酸二無水物とジアミンからなるイミド分子鎖とカルボキシル基側鎖を持つ構成単位を少なくとも1個有するポリイミド樹脂;エポキシビニルエステル樹脂の水酸基に多塩基酸無水物を反応させた構造を有する酸ペンダント型エポキシビニルエステル樹脂等が挙げられる。
熱硬化性樹脂としては、フェノール樹脂、尿素樹脂、メラミン樹脂、エポキシ樹脂、不飽和ポリエステル樹脂、ベンゾグアナミン誘導体、イソシアネート化合物、ブロックイソシアネート化合物、マレイミド化合物、ベンゾオキサジン化合物、オキサゾリン化合物、カルボジイミド化合物、シクロカーボネート化合物、多官能オキセタン化合物、エピスルフィド樹脂等が挙げられる。
アクリル酸−t−ブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸イソオクチル、(メタ)アクリル酸イソノニル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸ジメチルアミノメチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸アミノプロピル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸エトキシエチル、(メタ)アクリル酸ポリ(エトキシ)エチル、(メタ)アクリル酸ブトキシエトキシエチル、(メタ)アクリル酸エチルヘキシル、(メタ)アクリル酸フェノキシエチル、(メタ)アクリル酸テトラヒドロフリル、(メタ)アクリル酸ビニル、(メタ)アクリル酸アリル、(メタ)アクリル酸ベンジル、4−(2−オキシラニルメトキシ)ブチル−2−プロペン酸エステル、7−オキサビシクロ[4.1.0]ヘプト−3−イル−2−プロペン酸エステル、7−オキサビシクロ[4.1.0]ヘプト−3−イル−2−プロペン酸エステル、7−オキサビシクロ[4.1.0]ヘプト−3−イルメチル−2−プロペン酸エステル、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリシクロデカンジメチロールジ(メタ)アクリレート、トリ[(メタ)アクリロイルエチル]イソシアヌレート、ポリエステル(メタ)アクリレートオリゴマー等が挙げられる。
即ち、上記エポキシ樹脂のエポキシ基1個に対し、上記不飽和一塩基酸のカルボキシル基が0.1〜1.0個で付加させた構造を有するエポキシ付加物において、該エポキシ付加物の水酸基1個に対し、上記多塩基酸無水物の酸無水物構造が0.1〜1.0個となる比率となるようにするのが好ましい。
上記エポキシ樹脂、上記不飽和一塩基酸及び上記多塩基酸無水物の反応は、常法に従って行うことができる。
ルグリシジルエーテル、フェニルグリシジルエーテル、p−メトキシグリシジルエーテル、p−ブチルフェノールグリシジルエーテル、クレジルグリシジルエーテル、2−メチルクレジルグリシジルエーテル、4−ノニルフェニルグリシジルエーテル、ベンジルグリシジルエーテル、p−クミルフェニルグリシジルエーテル、トリチルグリシジルエーテル、2,3−エポキシプロピルメタクリレート、エポキシ化大豆油、エポキシ化アマニ油、グリシジルブチレート、ビニルシクロヘキサンモノオキシド、1,2−エポキシ−4−ビニルシクロヘキサン、スチレンオキシド、ピネンオキシド、メチルスチレンオキシド、シクロヘキセンオキシド、プロピレンオキシド、7−オキサビシクロ[4.1.0]ヘプト−3−イル−2−プロペン酸エステル等が挙げられる。
上記ビスフェノール型エポキシ化合物としては、水添ビスフェノール型エポキシ化合物等のビスフェノール型エポキシ化合物も用いることができる。
また上記グリシジルエーテル類としては、エチレングリコールジグリシジルエーテル、プロピレングリコールジグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、1,8−オクタンジオールジグリシジルエーテル、1,10−デカンジオールジグリシジルエーテル、2,2−ジメチル−1,3−プロパンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、テトラエチレングリコールジグリシジルエーテル、ヘキサエチレングリコールジグリシジルエーテル、1,4−シクロヘキサンジメタノールジグリシジルエーテル、1,1,1−トリ(グリシジルオキシメチル)プロパン、1,1,1−トリ(グリシジルオキシメチル)エタン、1,1,1−トリ(グリシジルオキシメチル)メタン、1,1,1,1−テトラ(グリシジルオキシメチル)メタン等を用いることができる。
その他、フェノールノボラック型エポキシ化合物、ビフェニルノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ジシクロペンタジエンノボラック型エポキシ化合物等のノボラック型エポキシ化合物;3,4−エポキシ−6−メチルシクロヘキシルメチル−3,4−エポキシ−6−メチルシクロヘキサンカルボキシレート、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、1−エポキシエチル−3,4−エポキシシクロヘキサン等の脂環式エポキシ化合物;フタル酸ジグリシジルエステル、テトラヒドロフタル酸ジグリシジルエステル、ダイマー酸グリシジルエステル等のグリシジルエステル類;テトラグリシジルジアミノジフェニルメタン、トリグリシジルP−アミノフェノール、N,N−ジグリシジルアニリン等のグリシジルアミン類;1,3−ジグリシジル−5,5−ジメチルヒダントイン、トリグリシジルイソシアヌレート等の複素環式エポキシ化合物;ジシクロペンタジエンジオキシド等のジオキシド化合物;ナフタレン型エポキシ化合物;トリフェニルメタン型エポキシ化合物;ジシクロペンタジエン型エポキシ化合物等を用いることもできる。
本発明の重合性組成物は重合開始剤(C)を含有する。
本発明の重合性組成物に用いられる重合開始剤(C)としては、ラジカル重合開始剤及びカチオン重合開始剤が挙げられる。ラジカル重合開始剤としては、光照射によりラジカルを発生する光ラジカル重合開始剤、或いは加熱によりラジカルを発生する熱ラジカル重合開始剤を用いることができ、特に制限されず従来既知の化合物を用いることが可能である。光ラジカル重合開始剤としては、例えば、アセトフェノン系化合物、ベンジル系化合物、ベンゾフェノン系化合物、チオキサントン系化合物などのケトン系化合物、オキシムエステル系化合物などを好ましいものとして例示することができる。
−2−メチルプロピオフェノン、2−ヒドロキシメチル−2−メチルプロピオフェノン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、p−ジメチルアミノアセトフェノン、p−ターシャリブチルジクロロアセトフェノン、p−ターシャリブチルトリクロロアセトフェノン、p−アジドベンザルアセトフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、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ノン−1、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾイン−n−ブチルエーテル、ベンゾインイソブチルエーテル、1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン等が挙げられる。
感度及び耐熱性の点から好ましい。
R73及びR74は、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基、R75、OR76、SR77、NR78R79、COR80、SOR81、SO2R82又はCONR83R84を表し、
R75〜R84は、それぞれ独立に、炭素原子数1〜20の炭化水素基又は複素環を含有する炭素原子数2〜20基を表し、
R83及びR84は互いに結合して環を形成している場合があり、
X21は、酸素原子、硫黄原子、セレン原子、CR85R86、CO、NR87又はPR88を表し、
X22は、単結合又はCOを表し、
R85〜R88は、炭素原子数1〜20の炭化水素基を表し、
上記炭素原子数1〜20の炭化水素基及び複素環を含有する炭素原子数2〜20基中の水素原子の一つ又は2つ以上が、ハロゲン原子、ニトロ基、シアノ基、水酸基、カルボキシル基又は複素環基で置換されている場合があり、上記炭素原子数1〜20の炭化水素基及び複素環を含有する炭素原子数2〜20基中のメチレン基の一つ以上が−O−に置換されている場合があり、
R73及びR74は、それぞれ独立に、隣接するベンゼン環と一緒になって環を形成している場合があり、
jは、0〜4の整数を表し、
kは、0〜5の整数を表す。)
ここで陽イオン[M]r+はオニウムであることが好ましく、その構造は、例えば、下記一般式、[(R29)fQ]r+で表すことができる。
)〔(1,2,3,4,5,6−η)−(1−メチルエチル)ベンゼン〕−アイアン−ヘキサフルオロホスフェート等の鉄−アレーン錯体や、トリス(アセチルアセトナト)アルミニウム、トリス(エチルアセトナトアセタト)アルミニウム、トリス(サリチルアルデヒダト)アルミニウム等のアルミニウム錯体とトリフェニルシラノール等のシラノール類との混合物等も挙げることができる。
上記芳香族スルホニウム塩としては、市販のものを用いることもでき、例えば、WPAG−336、WPAG−367、WPAG−370、WPAG−469、WPAG−638(和光純薬工業社製)、CPI−100P、CPI−101A、CPI−200K、CPI−210S(サンアプロ社製)、アデカオプトマーSP−056、アデカオプトマーSP−066、アデカオプトマーSP−130、アデカオプトマーSP−140、アデカオプトマーSP−082、アデカオプトマーSP−103、アデカオプトマーSP−601、アデカオプトマーSP−606、アデカオプトマーSP−701(ADEKA社製)等が挙げられる。
上記着色剤(D)としては、例えば、顔料、染料、天然色素等が挙げられる。
本発明の重合性組成物は充填剤を含有する場合がある。充填剤として、無機充填剤又は有機充填剤を用いることができる。無機充填剤は、通常シリコーン樹脂組成物、エポキシ樹脂組成物等の封止材料に配合されるものを使用することができる。例えば、溶融シリカ、溶融球状シリカ、結晶性シリカ、コロイダルシリカ、ヒュームドシリカ、シリカゲル等のシリカ類;アルミナ、酸化鉄、三酸化アンチモン等の金属酸化物;窒化ケイ素、窒化アルミニウム、窒化ホウ素、炭化ケイ素等のセラミックス;マイカやモンモリロナイト等の鉱物;水酸化アルミニウム、水酸化マグネシウム等の金属水酸化物或いはこれらを有機変性処理等により改質したもの;炭酸カルシウム、ケイ酸カルシウム、炭酸マグネシウム、炭酸バリウム等の金属炭酸塩或いはこれらを有機変性処理等により改質したもの;金属ホウ酸塩、カーボンブラック等の顔料;炭素繊維、グラファイト、ウィスカ、カオリン、タルク、ガラス繊維、ガラスビーズ、ガラスマイクロスフィア、シリカガラス、層状粘土鉱物、クレー、炭化ケイ素、石英、アルミニウム、亜鉛等が挙げられる。有機充填剤としては、アクリルビーズ、ポリマー微粒子、透明樹脂ビーズ、木粉、パルプ、木綿チップ等が挙げられる。
これらの中でも、ケトン類、エーテルエステル系溶剤等、特にプロピレングリコール−1−モノメチルエーテル−2−アセテート、シクロヘキサノン等が、感光性組成物において、レジストと重合開始剤の相溶性がよいので好ましい。
また、重合性組成物の塗膜を基板上に形成し、該塗膜に所定のパターン形状を有するマスクを介して活性光を照射した後、露光後の被膜を現像液(特にアルカリ現像液)にて現像し、現像後の該被膜を加熱する工程によりパターニングすることもできる。
ソルダーレジスト層は、重合性組成物をブレードコーター、リップコーター、コンマコーター、フィルムコーター等でキャリアフィルム又はカバーフィルムに5〜100μmの厚さで均一に塗布し乾燥して形成される。
カバーフィルムとしては、ポリエチレンフィルム、ポリプロピレンフィルム等を使用することができるが、ソルダーレジスト層との接着力が、キャリアフィルムよりも小さいものが良い。
四ツ口フラスコ中に、窒素雰囲気化において下記ブロック化剤No.1を0.1mol仕込み、温度を35℃に調整した後、3−イソシアネートプロピルトリエトキシシラン0.1molを温度が40℃以上に上がらないようコントロールしながら滴下した。その後、内温40℃で1時間撹拌した。IRでイソシアネート基のピークが消失したことを確認し、下記ブロックイソシアネートシランNo.1を得た。
ブロック化剤No.1の代わりにペンタエリスリトールトリアクリレートを用いた以外は、[製造例1]と同様の操作を行い、ブロックイソシアネートシランNo.2を得た。
1,1−ビス〔4−(2,3−エポキシプロピルオキシ)フェニル〕インダンの184g、アクリル酸58g、2,6−ジ−tert−ブチル−p−クレゾール0.26g、テトラ−n−ブチルアンモニウムブロミド0.11g及びPGMEA105gを仕込み、120℃で16時間撹拌した。反応液を室温まで冷却し、PGMEA160g、ビフタル酸無水物59g及びテトラ−n−ブチルアンモニウムブロミド0.24gを加えて、120℃で4時間撹拌した。更に、テトラヒドロ無水フタル酸20gを加え、120℃で4時間、100℃で3時間、80℃で4時間、60℃で6時間、40℃で11時間撹拌した後、PGMEA128gを加えて、PGMEA溶液として重合性化合物B−1を得た(Mw=5000、Mn=2100、酸価(固形分換算)92.7mgKOH/g)。
9,9−ビス(4−グリシジルオキシフェニル)フルオレン75.0g、アクリル酸23.8g、2,6−ジ−t−ブチル−p−クレゾール0.273g、テトラブチルアンモニウムクロリド0.585g、及びPGMEA65.9gを仕込み、90℃で1時間、100℃で1時間、110℃で1時間及び120℃で14時間撹拌した。室温まで冷却し、無水コハク酸25.9g、テトラブチルアンモニウムクロリド0.427g、及びPGMEA1.37gを加えて、100℃で5時間撹拌した。更に、9,9−ビス(4−グリシジルオキシフェニル)フルオレン30.0g、2,6−ジ−t−ブチル−p−クレゾール0.269g、及びPGMEA1.50gを加えて、90℃で90分、120℃で4時間撹拌後、PGMEA122.2gを加えて、PGMEA溶液として目的物である重合性化合物B−2を得た(Mw=4190、Mn=2170,酸価(固形分換算)52mg・KOH/g)
MA100(三菱化学社製カーボンブラック)150g及びペルオキソ2硫酸ナトリウム脱イオン水溶液(濃度2.0N)3000mlを混合し、60℃で10時間撹拌した。ろ過し、得られたスラリーを水酸化ナトリウムで中和し、ダイアフィルトレーションにより処理し、得られた固体を75℃で一晩乾燥し、黒色粉末としてカーボンブラックNo.1を得た。
カーボンブラックNo.1を16g、重合性化合物B−1PGMEA溶液を3.6g、DISPERBYK−161(ビックケミー製、分散剤)を2.4g及びPGMEAを78g、それぞれ秤量して合わせ、ビーズミルにより処理して、カーボンブラック分散液No.1を得た。
[表1]及び[表2]の配合に従って各成分を混合し、重合性組成物(実施例1〜6及び比較例1〜4)を得た。尚、表中の配合の数値は質量部を表す。また、表中の符号は、下記の成分を表す。
A−1:ブロックイソシアネートシラン化合物No.1
A−2:ブロックイソシアネートシラン化合物No.2
A−3:KBE−9007(信越シリコーン社製)
A−4:KBM−5103(信越シリコーン社製)
A−5:KBM−503 (信越シリコーン社製)
A−6:KBM−403 (信越シリコーン社製)
B−1:重合性化合物B−1PGMEA溶液(固形分45%)
B−2:重合性化合物B−2PGMEA溶液(固形分45%)
B−3:カヤラッドDPHA(日本化薬社製)
C−1:化合物No.C9
C−2:化合物No.C15
D−1:カーボンブラック分散液No.1(固形分20%PGMEA分散液)
E−1:PGMEA
ガラス基板上に上記重合性組成物をスピンコート(500rpm、10秒間)し乾燥させた後、100℃で100秒間プリベークを行った。光源として超高圧水銀ランプを用いて露光後した後、230℃で30分間ベークすることで樹脂製ブラックマトリクス層のあるガラス基板を得た。ガラス基板に6mmx3.5mmの面積で熱硬化接着剤(シール剤:三井化学社製XN−21S)を塗布し、樹脂製ブラックマトリクス層のあるガラス基板と、ブラックマトリクス層が接着面となるように貼りあわせ、接着剤を硬化させた。貼りあわされた基板を120℃、2atm、相対湿度100%の条件の高温高湿装置内に5時間静置した。このサンプルについて島津製EZ−Graphにて3点支持曲げ試験を実施し、密着強度を測定した。
ガラス基板上に上記重合性組成物をスピンコート(500rpm、10秒間)し乾燥させた後、100℃で100秒間プリベークを行った。光源として超高圧水銀ランプを用いて露光後した後、230℃で30分間ベークすることで樹脂製ブラックマトリクス層のあるガラス基板を得た。得られた樹脂製ブラックマトリクス層のある基板を120℃、2atm、相対湿度100%の条件にて高温高湿装置内に5時間静置した。JIS K5600−5−6に従って、カッターにて黒色層に1mm2のマスを100個作成した。その上にポリイミドテープを貼り付け、黒色層がハガレ割合を観察した。全くハガレなかったものを○、部分的にハガレたものを△、全てハガレたものを×とした。
上記重合性組成物をスクリュー管瓶に充填し、40℃において3日間静置した。静置後のレジスト液の粘度を測定し、粘度変化が5%以内であれば○、5%以上あるものを×とした。
基板上に上記重合性組成物をスピンコート(500rpm、10秒間)し乾燥させた後、100℃で100秒間プリベークを行った。光源として超高圧水銀ランプを用いて露光後した後、230℃で30分間ベークして硬化物を作成した。得られた膜のOD値を、マクベス透過濃度計を用いて測定し、該OD値をポストベイク後の厚さで割って、1μmあたりのOD値を算出した。
1μmあたりのOD値が3.5以上の硬化物はブラックマトリクスとして使用することができ、厚さあたりのOD値が4.0以上の硬化物はブラックマトリクスとして好ましく使用することができる。
(感度)
マスク開口6μmのフォトマスクを用いて、露光量を10mJ/cm2〜100mJ/cm2の間において10mJ/cm間隔で現像を行い、現像後のパターンが6μm以上となった部分を感度とし、露光量が40cJ/cm2以下のものをブラックマトリクスとして好ましく使用することができる。
それに対して、比較例1〜3の重合性組成物又は硬化物は、保存安定性、感度、基材への接着力、密着力の全てにおいて優れるものはなかった。
よって、本発明の重合性組成物は、ディスプレイ表示装置などの部材として好適に用いられることは明らかである。
Claims (10)
- 下記一般式(I)で表されるイソシアネート化合物とブロック化剤とを反応させて得られる構造を有するブロックイソシアネートシラン化合物(A)、重合性化合物(B)及び重合開始剤(C)を含有する重合性組成物。
R2は、水素原子、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、
Z1は、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、Z1で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR4−、−NR4CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
R4は、水素原子、炭素原子数1〜20の炭化水素基を表し、
aは1〜3の数であり、a≧2の場合、複数存在するR1は同一である場合があり、異なる場合があり、
bは0〜2の数を表し、b=2の場合、複数存在するR2は、同一である場合があり、異なる場合があり、
a+b=3である。) - ブロックイソシアネートシラン化合物(A)が下記一般式(II)で表される化合物である請求項1に記載の重合性組成物。
R3は、水素原子又はメチル基を表し、
X1及びX3は、それぞれ独立に、直接結合又は炭素原子数1〜20の炭化水素基を表し、
X2は、炭素原子数1〜20の炭化水素基、又は複素環を含有する炭素原子数2〜20の基を表し、
X1、X2及びX3で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR4−、−NR4CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
Yは、酸素原子、硫黄原子、又は−NR4−を表し、
R4は、水素原子、炭素原子数1〜20の炭化水素基を表し、
cは、2〜10の数を表し、
c≧2の場合、複数存在するR3は、同一の場合があり異なる場合があり、
dは、1〜3の数を表し、
d≧2の場合、R1、R2、X3及びZ1は、それぞれ、同一の場合があり、異なる場合がある。) - ブロックイソシアネートシラン化合物(A)が下記一般式(III)で表される基を有するブロックイソシアネートシラン化合物である請求項1又は2に記載の重合性組成物。
- 上記重合性化合物(B)が、
下記一般式(IV)で表されるエポキシ化合物、
下記一般式(IV)で表されるエポキシ化合物と不飽和一塩基酸とをエステル化させた構造を有する不飽和化合物、又は
下記一般式(IV)で表されるエポキシ化合物と不飽和一塩基酸とをエステル化させた構造を有する不飽和化合物に、更に多塩基酸無水物をエステル化させた構造を有する不飽和化合物
である請求項1〜3の何れか一項に記載の重合性組成物。
Mで表される炭素原子数1〜20の炭化水素基中の1つ又は2つ以上の水素原子はハロゲン原子で置換される場合があり、
R11、R12、R13、R14、R15、R16、R17及びR18は、それぞれ独立に、水素原子、炭素原子数1〜20の炭化水素基又はハロゲン原子を表し、
R11〜R18で表される基中のメチレン基は、酸素が隣り合わない条件で、−O−に置換されている場合があり、
nは0〜10の数を表し、
nが0でない場合、複数存在するR11、R12、R13、R14、R15、R16、R17、R18及びMは、それぞれ、同一である場合があり、異なる場合がある。)
R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49及びR50は、それぞれ独立に、水素原子、炭素原子数1〜20の炭化水素基、複素環を含有する炭素原子数2〜20の基、又はハロゲン原子を表し、
R22、R23、R24、R25、R26、R27、R28、R29、R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41、R42、R43、R44、R45、R46、R47、R48、R49及びR50で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−又は−S−に置換される場合があり、
R22とR23、R23とR24、R24とR25、R25とR26、R27とR28、R28とR29、R29とR30、R35とR36、R36とR37、R37とR38、R43とR44、R44とR45、R45とR46、R47とR48、R48とR49及びR49とR50は結合して環を形成する場合があり、
式中の*は、(a)、(b)、(c)及び(d)で表される基が、*部分で隣接する基と結合することを意味する。) - 重合開始剤(C)が、下記一般式(V)で表される基を有する化合物である請求項1〜4の何れか一項に記載の重合性組成物。
R61及びR62で表される基中の水素原子の1つ又は2つ以上はハロゲン原子、ニトロ基、シアノ基、水酸基、アミノ基、カルボキシル基、メタクリロイル基、アクリロイル基、エポキシ基、ビニル基、ビニルエーテル基、メルカプト基、イソシアネート基又は複素環を含有する炭素原子数2〜20の基で置換されている場合があり、
R61及びR62で表される基中のメチレン基の1つ又は2つ以上は、酸素が隣り合わない条件で、−O−、−CO−、−COO−、−OCO−、−NR63−、−NR63CO−、−S−、−CS−、−SO2−、−SCO−、−COS−、−OCS−又はCSO−に置換される場合があり、
R63は、水素原子又は炭素原子数1〜20の炭化水素基を表し、
mは0又は1を表し、
式中の*は、一般式(V)で表される基が、*部分で、隣接する基と結合することを意味する。) - 更に着色剤(D)を含有する請求項1〜5の何れか一項に記載の重合性組成物。
- 請求項1〜6に記載の何れか一項に重合性組成物を含有するブラックマトリクス用感光性組成物。
- 請求項1〜6の何れか一項に記載の重合性組成物又は請求項7に記載のブラックマトリクス用感光性組成物を光又は熱によって硬化させる、硬化物の製造方法。
- 請求項1〜6の何れか一項に記載の重合性組成物又は請求項7に記載のブラックマトリクス用感光性組成物の硬化物。
- 請求項9に記載の硬化物を含有するカラーフィルタ。
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