JP6633382B2 - 感光性樹脂組成物、それから形成される光硬化パターン、及びそれを備えた画像表示装置 - Google Patents
感光性樹脂組成物、それから形成される光硬化パターン、及びそれを備えた画像表示装置 Download PDFInfo
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- JP6633382B2 JP6633382B2 JP2015246492A JP2015246492A JP6633382B2 JP 6633382 B2 JP6633382 B2 JP 6633382B2 JP 2015246492 A JP2015246492 A JP 2015246492A JP 2015246492 A JP2015246492 A JP 2015246492A JP 6633382 B2 JP6633382 B2 JP 6633382B2
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- 239000011342 resin composition Substances 0.000 title claims description 60
- -1 oxime ester Chemical class 0.000 claims description 76
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 75
- 229920005989 resin Polymers 0.000 claims description 62
- 239000011347 resin Substances 0.000 claims description 62
- 239000000126 substance Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 15
- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- NKVCQMYWYHDOOF-UHFFFAOYSA-N 1-phenoxyethane-1,2-diol Chemical compound OCC(O)OC1=CC=CC=C1 NKVCQMYWYHDOOF-UHFFFAOYSA-N 0.000 claims description 6
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 claims description 6
- RKYJPYDJNQXILT-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCOC(=O)C=C RKYJPYDJNQXILT-UHFFFAOYSA-N 0.000 claims description 6
- UECGJSXCVLTIMQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OCCOC(=O)C=C UECGJSXCVLTIMQ-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 229920002120 photoresistant polymer Polymers 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000006850 spacer group Chemical group 0.000 claims description 5
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 claims description 3
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 3
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 3
- SHJIJMBTDZCOFE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-methoxyethanol Chemical compound COC(O)COCCOCCOCCO SHJIJMBTDZCOFE-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RSHKWPIEJYAPCL-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CC)COC1 RSHKWPIEJYAPCL-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
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- 150000002921 oxetanes Chemical class 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
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000006353 oxyethylene group Chemical group 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
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- LVDAGIFABMFXSJ-UHFFFAOYSA-N propyl 2-butoxyacetate Chemical compound CCCCOCC(=O)OCCC LVDAGIFABMFXSJ-UHFFFAOYSA-N 0.000 description 1
- GYOCIFXDRJJHPF-UHFFFAOYSA-N propyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OCCC GYOCIFXDRJJHPF-UHFFFAOYSA-N 0.000 description 1
- ADOFEJQZDCWAIL-UHFFFAOYSA-N propyl 2-ethoxyacetate Chemical compound CCCOC(=O)COCC ADOFEJQZDCWAIL-UHFFFAOYSA-N 0.000 description 1
- GXKPKHWZTLSCIB-UHFFFAOYSA-N propyl 2-ethoxypropanoate Chemical compound CCCOC(=O)C(C)OCC GXKPKHWZTLSCIB-UHFFFAOYSA-N 0.000 description 1
- FIABMSNMLZUWQH-UHFFFAOYSA-N propyl 2-methoxyacetate Chemical compound CCCOC(=O)COC FIABMSNMLZUWQH-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- BMVTVMIDGMNRRR-UHFFFAOYSA-N propyl 2-propoxyacetate Chemical compound CCCOCC(=O)OCCC BMVTVMIDGMNRRR-UHFFFAOYSA-N 0.000 description 1
- HJIYVZIALQOKQI-UHFFFAOYSA-N propyl 3-butoxypropanoate Chemical compound CCCCOCCC(=O)OCCC HJIYVZIALQOKQI-UHFFFAOYSA-N 0.000 description 1
- IYVPXMGWHZBPIR-UHFFFAOYSA-N propyl 3-ethoxypropanoate Chemical compound CCCOC(=O)CCOCC IYVPXMGWHZBPIR-UHFFFAOYSA-N 0.000 description 1
- KNCDNPMGXGIVOM-UHFFFAOYSA-N propyl 3-hydroxypropanoate Chemical compound CCCOC(=O)CCO KNCDNPMGXGIVOM-UHFFFAOYSA-N 0.000 description 1
- JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
- YTUFRRBSSNRYID-UHFFFAOYSA-N propyl 3-propoxypropanoate Chemical compound CCCOCCC(=O)OCCC YTUFRRBSSNRYID-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Description
〔式中、R1は、水素又はメチル基であり、R2は、水素又は炭素数1〜6のアルキル基である。〕
〔式中、R3は、水素又はメチル基である。〕
〔式中、L1は、水素又は炭素数1〜10のアルキル基であり、L2は、水素、炭素数1〜6のアルキル基又は炭素数6〜12のアリール基であり、L3は、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基又は−SC6H5である。〕
〔式中、R4、R5、R6、及びR7は、互いに独立して、水素又はメチル基であり、
R8は、ベンジル(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、(2−フェニル)フェノキシエトキシ(メタ)アクリレート、2−ヒドロキシ−(2−フェニル)フェノールプロピル(メタ)アクリレート、2−ヒドロキシ−(3−フェニル)フェノキシプロピル(メタ)アクリレート、テトラヒドロフリル(メタ)アクリレート、(メタ)スチレン、ビニルトルエン、ビニルナフタレン、N−ベンジルマレイミド、メチル(メタ)アクリレート、エチル(メタ)アクリレート、メトキシエチレングリコール(メタ)アクリレート、メトキシジエチレングリコール(メタ)アクリレート、メトキシトリエチレングリコール(メタ)アクリレート、メトキシテトラエチレングリコール(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、及びテトラヒドロフリル(メタ)アクリレートからなる群から選択される単量体に由来する構造であり、
R9は、下記式(1)〜(7)からなる群から選択される単量体に由来する構造であり、
R10は、(メタ)アクリル酸、2−(メタ)アクリロイルオキシエチルスクシネート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、及び2−(メタ)アクリロイルオキシエチルスクシネートからなる群から選択される単量体に由来する構造であり、
R11は、水素又は炭素数1〜6のアルキル基であり、
a=20〜60mol%、b=5〜30mol%、c=10〜50mol%、d=5〜30mol%である。〕
〔式中、R12及びR13は、互いに独立して、水素又はメチル基であり、
R14は、下記式(8)の単量体に由来する構造であり、
R15は、(メタ)アクリル酸、2−(メタ)アクリロイルオキシエチルスクシネート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、及び2−(メタ)アクリロイルオキシエチルスクシネートからなる群から選択される単量体に由来する構造であり、
e=50〜95mol%、f=5〜50mol%である。〕
〔式中、L3〜L20は、互いに独立して、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基又はハロゲン原子である。〕
〔式中、L21及びL22は、互いに独立して、炭素数1〜5のアルキル基である。〕
本発明の感光性樹脂組成物は、アルカリ可溶性樹脂(A)と、重合性単量体化合物(B)と、ビイミダゾール系開始剤(C1)と、オキシムエステル系開始剤(C2)と、溶媒(E)とを含む。
本発明に用いられるアルカリ可溶性樹脂(A)は、パターンを形成する際の現像処理工程で用いられるアルカリ現像液に対して可溶性を付与する成分であり、下記化学式1で示される繰り返し単位を有する第1の樹脂と、下記化学式2で示される繰り返し単位を有する第2の樹脂とを含む。
〔式中、R1は、水素又はメチル基であり、R2は、水素又は炭素数1〜6のアルキル基である。〕
〔式中、繰り返し単位aは、ベンジル(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、(2−フェニル)フェノキシエトキシ(メタ)アクリレート、2−ヒドロキシ−(2−フェニル)フェノールプロピル(メタ)アクリレート、2−ヒドロキシ−(3−フェニル)フェノキシプロピル(メタ)アクリレート、テトラヒドロフリル(メタ)アクリレート、スチレン、α―メチルスチレン、ビニルトルエン、ビニルナフタレン、N−ベンジルマレイミド、メチル(メタ)アクリレート、エチル(メタ)アクリレート、メトキシエチレングリコール(メタ)アクリレート、メトキシジエチレングリコール(メタ)アクリレート、メトキシトリエチレングリコール(メタ)アクリレート、メトキシテトラエチレングリコール(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、及びテトラヒドロフリル(メタ)アクリレートからなる群から選択される単量体に由来する構造であり、R 4 は、水素又はメチル基であり、
繰り返し単位bは、下記式(1)〜(7)からなる群から選択される単量体に由来する構造であり、R 5 は、水素又はメチル基であり、
繰り返し単位cは、(メタ)アクリル酸、2−(メタ)アクリロイルオキシエチルスクシネート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、及び2−(メタ)アクリロイルオキシエチルスクシネートからなる群から選択される単量体に由来する構造であり、R 6 は、水素又はメチル基であり、
R 7 は、水素又はメチル基であり、R11は、水素又は炭素数1〜6のアルキル基であり、
a=20〜60mol%、b=5〜30mol%、c=10〜50mol%、d=5〜30mol%である。〕
〔式中、R16、R17、R18、及びR19は、互いに独立して、水素又はメチル基であり、a=20〜60mol%、b=5〜30mol%、c=10〜50mol%、d=5〜30mol%である。〕
〔式中、R3は、水素又はメチル基である。〕
〔式中、繰り返し単位eは、下記式(8)の単量体に由来する構造であり、R 12 は、水素又はメチル基であり、
繰り返し単位fは、(メタ)アクリル酸、2−(メタ)アクリロイルオキシエチルスクシネート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、及び2−(メタ)アクリロイルオキシエチルスクシネートからなる群から選択される単量体に由来する構造であり、R 13 は、水素又はメチル基であり、
e=50〜95mol%、f=5〜50mol%である。〕
〔式中、R20及びR21は、互いに独立して、水素又はメチル基であり、e=50〜95mol%、f=5〜50mol%である。〕
本発明の感光性樹脂組成物に用いられる重合性化合物(B)は、製造工程中の架橋密度を増加させ、光硬化パターンの機械的特性を強化し得る。
本発明による光重合開始剤(C)は、前記重合性化合物(B)を重合し得る成分であり、ビイミダゾール系開始剤(C1)と、下記化学式3で示されるオキシムエステル系開始剤(C2)とを含む。
〔式中、L1は、水素又は炭素数1〜10のアルキル基であり、L2は、水素、炭素数1〜6のアルキル基又は炭素数6〜12のアリール基であり、L3は、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基又は−SC6H5である。〕
本発明の感光性樹脂組成物は、必要に応じて増感剤(D)をさらに含むことができる。本発明による増感剤(D)は、ビイミダゾール系開始剤(C1)のラジカル生成反応を促進させて、ラジカル重合の反応性が向上し、架橋密度を向上させ、光硬化パターンの基材との密着性を向上させることができる。
溶媒(E)は、当分野において通常用いられるものであれば、何れでも制限されることなく用いることができる。
本発明による感光性樹脂組成物は、必要に応じて、充填剤、他の高分子化合物、硬化剤、レベリング剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤、連鎖移動剤等の添加剤をさらに含んでもよい。
本発明は、前記感光性樹脂組成物で製造される光硬化パターン及び前記光硬化パターンを含む画像表示装置を提供することを目的とする。
還流冷却器、滴下漏斗、及び撹拌機を備えた1Lのフラスコ内に、窒素を0.02L/分で流入するようにして窒素雰囲気下とし、プロピレングリコールモノメチルエーテルアセテート200g投入し、100℃に昇温した後、ベンジルメタクリレート61.6g(0.35モル)、トリシクロ[5.2.1.02,6]デカニルメタクリレート22.0g(0.10モル)、メタクリル酸47.3g(0.55モル)、及びプロピレングリコールモノメチルエーテルアセテート150gを含む混合物に2,2’−アゾビス(2,4−ジメチルバレロニトリル)3.6gを添加した溶液を滴下漏斗で2時間にかけてフラスコに滴下して100℃でさらに5時間撹拌を続けた。
還流冷却器、滴下漏斗、及び撹拌機を備えた1Lのフラスコ内に、窒素を0.02L/分で流入するようにして窒素雰囲気下とし、ジエチレングリコールメチルエチルエーテル150gを投入して撹拌し、70℃まで加熱した。次いで、下記化学式6及び化学式7の混合物(モル比は、50:50)210.2g(0.95mol)、及びメタクリル酸14.5g(0.17mol)をジエチレングリコールメチルエチルエーテル150gに溶解させて溶液を調製した。
還流冷却器、滴下漏斗、及び撹拌機を備えた1Lのフラスコ内に、窒素を0.02L/分で流入するようにして窒素雰囲気下とし、プロピレングリコールモノメチルエーテルアセテート200gを投入して、100℃に昇温した後、メタクリル酸47.3g(0.55モル)、ベンジルメタクリレート61.7g(0.35モル)、トリシクロ[5.2.1.02,6]デカニルメタクリレート22.0g(0.10モル)、及びプロピレングリコールモノメチルエーテルアセテート150gを含む混合物に2,2’−アゾビス(2,4−ジメチルバレロニトリル)3.6gを添加した溶液を滴下漏斗から2時間かけてフラスコに滴下した後、100℃でさらに7時間撹拌を続けた。反応終了後、固形分酸価が134mgKOH/gである樹脂A−3を得た。GPCによって測定したポリスチレン換算の重量平均分子量は、22,700であり、分子量分布(Mw/Mn)は、2.5であった。
下記表1及び表2に記載された組成及び含有量(質量部)を有する感光性樹脂組成物を調製した。
A−2:調製例2の樹脂
A−3:調製例3の樹脂
B−1:ジペンタエリスリトールヘキサアクリレート(KAYARAD DPHA:日本化薬(株)製)
C−1:2,2’−ビス(o−クロロフェニル)−4,5,4’,5’−テトラフェニル−1、2’−ビイミダゾール(B−CIM:保土谷化学工業(株)製)
C−2:2,2’−ビス(o−メトキシフェニル)−4,5,4’,5’−テトラフェニル−1,2’−ビイミダゾール(HABI−107:Tronly製)
C−3:化学式8で示されるビイミダゾール系化合物
C−4:化学式9で示されるオキシムエステル系化合物
C−5:化学式10で示されるオキシムエステル系化合物
D−1:化学式11で示される化合物
D−2:化学式12で示される化合物
D−3:化学式13で示される化合物
D−4:化学式14で示される化合物
E−1:プロピレングリコールモノメチルエーテルアセテート:ジエチレングリコールメチルエチルエーテル(6:4の体積比)
F−1(酸化防止剤):4,4’−ブチリデンビス[6−tert−ブチル−3−メチルフェノール](BBM−S:住友精密化学製)
2インチ角のガラス基板(イーグル2000、コーニング社製)を中性洗剤、水、及びアルコールで順次洗浄した後、乾燥させた。このガラス基板上に、前記実施例及び比較例で調製した感光性樹脂組成物をそれぞれスピンコーティングした後、ホットプレートを用いて90℃で125秒間プリベークを行った。前記プリベークを行った基板を常温で冷却後、石英硝子製フォトマスクとの間隔を150μmにして露光機(UX−1100SM;Ushio(株)製)を用いて60mJ/cm2の露光量(365nm基準)で光照射した。このとき、フォトマスクは、次のパターンが同一平面上に形成されたフォトマスクを用いた。
得られたドットパターンを三次元形状測定装置(SIS−2000システム;SNU Precision社製)で観察してパターンの底面から全体高さの5%の箇所をボトムCD(a)、底面から全体高さの95%の箇所をトップCD(b)と定義し、(b)の長さを(a)の長さで除した後、100を掛けた値(=b/a×100)をT/B比と定義した。
前記で得られた膜厚さ3.0μmにおけるパターンサイズを三次元形状測定装置(SIS−2000システム;SNU Precision社製)を用いて測定し、マスクサイズとの差をCD−Biasで下記のように算出する。CD−Biasは、0に近接するほど良好であり、(+)は、パターンのサイズがマスクより大きいことを、(−)は、パターンのサイズがマスクより小さいことを意味する。
CD−Bias=(形成されたパターンサイズ)−(形成の際に用いたマスクサイズ)
現像密着性は、25%の透過率を有するハーフトーンマスク(Half-tone Mask)を適用したマスクを用いて生成されたパターンが基板に密着される程度を把握するものであり、直径(size)が5〜20μmまで1μm間隔のドットパターンがそれぞれ1000個のあるフォトマスクによって膜厚さが3μmで形成されたパターンが欠落することなく100%残っている場合のパターンの実際サイズをSNU Precision社の3次元形状測定器SIS−2000を用いて線幅を測定した。パターン線幅の値は、パターンの底面から全体高さの5%の箇所をボトムCDの値と定義した。欠落することなく残っている最小パターンサイズが小さいほど現像密着性に優れる。
実施例及び比較例の樹脂組成物を基板に塗布して、それぞれスピンコーティングした後、ホットプレートを用いて90℃で125秒間プリベークを行った。前記プリベークを行った基板を常温で冷却した後、露光機(UX−1100SM;Ushio(株)製)を用いて60mJ/cm2の露光量(365nm基準)で塗膜の全面に光を照射した。
Claims (10)
- 下記化学式1で示される繰り返し単位を有する第1の樹脂、及び下記化学式2で示される繰り返し単位を有する第2の樹脂を含むアルカリ可溶性樹脂(A)と、重合性化合物(B)と、ビイミダゾール系開始剤(C1)と、下記化学式3で示されるオキシムエステル系開始剤(C2)と、下記化学式5で示される増感剤(D)と、溶媒(E)とを含む、感光性樹脂組成物。
〔式中、R1は、水素又はメチル基であり、R2は、水素又は炭素数1〜6のアルキル基である。〕
〔式中、R3は、水素又はメチル基である。〕
〔式中、L1は、水素又は炭素数1〜10のアルキル基であり、L2は、水素、炭素数1〜6のアルキル基又は炭素数6〜12のアリール基であり、L3は、水素、炭素数1〜6のアルキル基、炭素数6〜12のアリール基又は−SC6H5である。〕
〔式中、L 21 及びL 22 は、互いに独立して、炭素数1〜5のアルキル基である。〕 - 前記第1の樹脂と前記第2の樹脂との混合重量比は、20:80〜 80:20である、請求項1に記載の感光性樹脂組成物。
- 前記第1の樹脂の重量平均分子量は、10,000〜30,000である、請求項1に記載の感光性樹脂組成物。
- 前記第2の樹脂の重量平均分子量は、2,000〜20,000である、請求項1に記載の感光性樹脂組成物。
- 前記第1の樹脂は、化学式1−1で示される繰り返し単位を有する、請求項1に記載の感光性樹脂組成物。
〔式中、繰り返し単位aは、ベンジル(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、(2−フェニル)フェノキシエトキシ(メタ)アクリレート、2−ヒドロキシ−(2−フェニル)フェノールプロピル(メタ)アクリレート、2−ヒドロキシ−(3−フェニル)フェノキシプロピル(メタ)アクリレート、テトラヒドロフリル(メタ)アクリレート、スチレン、α―メチルスチレン、ビニルトルエン、ビニルナフタレン、N−ベンジルマレイミド、メチル(メタ)アクリレート、エチル(メタ)アクリレート、メトキシエチレングリコール(メタ)アクリレート、メトキシジエチレングリコール(メタ)アクリレート、メトキシトリエチレングリコール(メタ)アクリレート、メトキシテトラエチレングリコール(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、及びテトラヒドロフリル(メタ)アクリレートからなる群から選択される単量体に由来する構造であり、
繰り返し単位bは、下記式(1)〜(7)からなる群から選択される単量体に由来する構造であり、R 5 は、水素又はメチル基であり、
R 7 は、水素又はメチル基であり、R11は、水素又は炭素数1〜6のアルキル基であり、
a=20〜60mol%、b=5〜30mol%、c=10〜50mol%、d=5〜30mol%である。〕 - 前記第2の樹脂は、化学式2−1で示される繰り返し単位を有する、請求項1に記載の感光性樹脂組成物。
〔式中、繰り返し単位eは、下記式(8)の単量体に由来する構造であり、R 12 は、水素又はメチル基であり、
繰り返し単位fは、(メタ)アクリル酸、2−(メタ)アクリロイルオキシエチルスクシネート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、及び2−(メタ)アクリロイルオキシエチルスクシネートからなる群から選択される単量体に由来する構造であり、
e=50〜95mol%、f=5〜50mol%である。〕 - 前記ビイミダゾール系開始剤(C1)は、下記化学式4で示される、請求項1に記載の感光性樹脂組成物。
- 請求項1乃至7の何れか一項に記載の感光性樹脂組成物で形成される、光硬化パターン。
- 前記光硬化パターンは、アレイ平坦化膜パターン、保護膜パターン、絶縁膜パターン、フォトレジストパターン、ブラックマトリックスパターン、及びコラムスペーサパターンからなる群から選択される、請求項8に記載の光硬化パターン。
- 請求項8に記載の光硬化パターンを含む、画像表示装置。
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