JPWO2014091818A1 - 共重合体、それを含有する感光性樹脂組成物及び樹脂膜 - Google Patents
共重合体、それを含有する感光性樹脂組成物及び樹脂膜 Download PDFInfo
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- JPWO2014091818A1 JPWO2014091818A1 JP2014551921A JP2014551921A JPWO2014091818A1 JP WO2014091818 A1 JPWO2014091818 A1 JP WO2014091818A1 JP 2014551921 A JP2014551921 A JP 2014551921A JP 2014551921 A JP2014551921 A JP 2014551921A JP WO2014091818 A1 JPWO2014091818 A1 JP WO2014091818A1
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- Prior art keywords
- acrylate
- meth
- copolymer
- resin composition
- photosensitive resin
- Prior art date
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 52
- 239000011342 resin composition Substances 0.000 title claims abstract description 50
- 229920005989 resin Polymers 0.000 title claims description 41
- 239000011347 resin Substances 0.000 title claims description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 59
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 15
- -1 2-isocyanatoethyl Chemical group 0.000 claims description 34
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 3
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 3
- 238000002845 discoloration Methods 0.000 abstract description 8
- 238000003860 storage Methods 0.000 abstract description 8
- 239000010408 film Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 239000011229 interlayer Substances 0.000 description 7
- PJMXUSNWBKGQEZ-UHFFFAOYSA-N (4-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(O)C=C1 PJMXUSNWBKGQEZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 239000002253 acid Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-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
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 2
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
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- 238000007598 dipping method Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
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- 239000010410 layer Substances 0.000 description 2
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 239000004094 surface-active agent Substances 0.000 description 2
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- QWRVAXMLZCMVSL-UHFFFAOYSA-N (2,4,6-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC(O)=C(O)C(O)=C1 QWRVAXMLZCMVSL-UHFFFAOYSA-N 0.000 description 1
- ZDROXNKXVHPNBJ-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=C(O)C=CC=C1O ZDROXNKXVHPNBJ-UHFFFAOYSA-N 0.000 description 1
- DIBYQTLCOMYUAP-UHFFFAOYSA-N (2-hydroxy-4-methylphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=CC(C)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O DIBYQTLCOMYUAP-UHFFFAOYSA-N 0.000 description 1
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 1
- IUSXXDHQFMPZQX-UHFFFAOYSA-N (2-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=CC=C1OC(=O)C=C IUSXXDHQFMPZQX-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- NTHRHRINERQNSR-UHFFFAOYSA-N (3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC(O)=C1 NTHRHRINERQNSR-UHFFFAOYSA-N 0.000 description 1
- DRZPXZMMDBMTHL-UHFFFAOYSA-N (3-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=CC(OC(=O)C=C)=C1 DRZPXZMMDBMTHL-UHFFFAOYSA-N 0.000 description 1
- HWZREQONUGCFIT-UHFFFAOYSA-N (3-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=CC=CC(C(=O)C=2C(=C(O)C(O)=CC=2)O)=C1 HWZREQONUGCFIT-UHFFFAOYSA-N 0.000 description 1
- FVHMFMMVURPZFE-UHFFFAOYSA-N (4-hydroxy-3-methoxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=C(O)C(OC)=CC(C(=O)C=2C(=C(O)C(O)=CC=2)O)=C1 FVHMFMMVURPZFE-UHFFFAOYSA-N 0.000 description 1
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- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 description 1
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- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
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- 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
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 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
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 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
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
- C08K5/08—Quinones
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
特許文献3には、[A]不飽和カルボン酸とエポキシ基含有不飽和化合物とそれら以外のオレフィン系不飽和化合物との共重合体、及び[B]特定のフェノール化合物と1,2−ナフトキノンジアジドスルホン酸ハライドとの縮合物を含む感放射線性樹脂組成物が記載されている。
また、特許文献4及び5には、不飽カルボン酸と脂環式エポキシ基含有不飽和化合物との共重合体、及び1,2−ナフトキノンジアジドスルホン酸エステルを含む感光性樹脂組成物が記載されている。
即ち、本発明は、以下の[1]〜[9]で示される。
[1]ヒドロキシフェニル(メタ)アクリレート由来の繰り返し単位と、ブロックされたイソシアネート基含有不飽和化合物由来の繰り返し単位とを含むことを特徴とする共重合体。
[2]前記ヒドロキシフェニル(メタ)アクリレート由来の繰り返し単位30mol%〜90mol%と、前記ブロックされたイソシアネート基含有不飽和化合物由来の繰り返し単位10mol%〜70mol%とを含むことを特徴とする[1]に記載の共重合体。
[3]前記ブロックされたイソシアネート基含有不飽和化合物が、ブロックされた2−イソシアナトエチル(メタ)アクリレートであることを特徴とする[1]又は[2]に記載の共重合体。
[4]前記ブロックが、メチルエチルケトンオキシムによるものであることを特徴とする[1]〜[3]の何れかに記載の共重合体。
[5]前記ブロックされたイソシアネート基含有不飽和化合物が、2−(0−[1’−メチルプロピリデンアミノ]カルボキシアミノ)エチル(メタ)アクリレートであることを特徴とする[1]〜[4]の何れかに記載の共重合体。
[6][1]〜[5]の何れかに記載の共重合体及びキノンジアジド基含有化合物を含有することを特徴とする感光性樹脂組成物。
[7]前記共重合体100質量部に対して、前記キノンジアジド基含有化合物を5〜60質量部含むことを特徴とする[6]に記載の感光性樹脂組成物。
[8]溶媒以外の成分の合計量100質量部に対して、溶媒を30〜4000質量部含むことを特徴とする[6]又は[7]に記載の感光性樹脂組成物。
[9][6]〜[8]の何れかに記載の感光性樹脂組成物を基板上に塗布し、乾燥して得られることを特徴とする樹脂膜。
なお、明細書及び特許請求の範囲において、(メタ)アクリレートとは、メタクリレート又はアクリレートを意味する。
本発明の感光性樹脂組成物において必須成分として含まれる共重合体[A]は、(a1)ヒドロキシフェニル(メタ)アクリレート由来の繰り返し単位と、(a2)ブロックされたイソシアネート基含有不飽和化合物由来の繰り返し単位とを含むものである。
(a1)ヒドロキシフェニル(メタ)アクリレートの具体例としては、o−ヒドロキシフェニルアクリレート、m−ヒドロキシフェニルアクリレート、p−ヒドロキシフェニルアクリレート、o−ヒドロキシフェニルメタクリレート、m−ヒドロキシフェニルメタクリレート、p−ヒドロキシフェニルメタクリレートなどが挙げられる。これらは単独で使用してもよいし、2種以上を組み合わせて使用してもよい。また、これらの中でも、p−ヒドロキシフェニルメタクリレートが好ましい。
カラム:ショウデックス(登録商標) KF−801+KF−802+KF−802+KF−803
カラム温度:40℃
展開溶媒:テトラヒドロフラン
検出器:示差屈折計(ショウデックス(登録商標) RI−101)
流速:1mL/min
重合開始剤としては、例えば、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、2,2’−アゾビス(2−ブチロニトリル)、2,2’−アゾビスイソブチロニトリル、ジメチル−2,2’−アゾビスイソブチレート、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)等のアゾ系開始剤やベンゾイルパーオキサイド、ラウリルパーオキサイド、オクタノイルパーオキサイド、アセチルパーオキサイド、ジ−t−ブチルパーオキサイド、t−ブチルクミルパーオキサイド、ジクミルパーオキサイド、t−ブチルパーオキシアセテート、t−ブチルパーオキシベンゾエート等の有機過酸化物が挙げられる。
〔実施例1〕
還流冷却器及び攪拌機を備えたフラスコに、p−ヒドロキシフェニルメタクリレート42質量部、2−(0−[1’−メチルプロピリデンアミノ]カルボキシアミノ)エチルメタクリレート58質量部、プロピレングリコールモノメチルエーテルアセテート400質量部及び2,2’−アゾビスイソブチロニトリル6質量部を仕込み、窒素置換した後、攪拌しながら液温を80℃に上昇させ、80℃で6時間反応させた。ゲル・パーミエーション・クロマトグラフィーによりモノマーの消失を確認し、100℃に昇温して30分間エージングを行った。80℃、減圧下でプロピレングリコールモノメチルエーテルアセテートを蒸留により取り除き、固形分濃度を30質量%に調整して、共重合体[A−1]を含む樹脂溶液(S−1)を得た。
樹脂溶液中に含まれる共重合体[A−1]のポリスチレン換算重量平均分子量(Mw)は8,700であり、分子量分布(Mw/Mn)は3.5であった。
還流冷却器及び攪拌機を備えたフラスコに、p−ヒドロキシフェニルメタクリレート41質量部、2−[(3,5−ジメチルピラゾリル)カルボニルアミノ]エチルメタクリレート59質量部、プロピレングリコールモノメチルエーテルアセテート400質量部及び2,2'−アゾビスイソブチロニトリル6質量部を仕込み、実施例1と同様に反応を行って、共重合体[A−2]を含む樹脂溶液(S−2)を得た。
樹脂溶液中に含まれる共重合体[A−2]のポリスチレン換算重量平均分子量(Mw)は8,800であり、分子量分布(Mw/Mn)は3.5であった。
還流冷却器及び攪拌機を備えたフラスコに、p−ヒドロキシフェニルメタクリレート36質量部、2−(0−[1'−メチルプロピリデンアミノ]カルボキシアミノ)エチルメタクリレート51質量部、n−ブチルアクリレート13質量部、プロピレングリコールモノメチルエーテルアセテート400質量部及び2,2'−アゾビスイソブチロニトリル6質量部を仕込み、実施例1と同様に反応を行って、共重合体[A−3]を含む樹脂溶液(S−3)を得た。
樹脂溶液中に含まれる共重合体[A−3]のポリスチレン換算重量平均分子量(Mw)は8,300であり、分子量分布(Mw/Mn)は3.3であった。
還流冷却器及び攪拌機を備えたフラスコに、p−ヒドロキシフェニルメタクリレート56質量部、グリシジルメタクリレート44質量部、プロピレングリコールモノメチルエーテルアセテー600質量部及び2,2’−アゾビスイソブチロニトリル6質量部を仕込み、窒素置換した後、攪拌しながら液温を80℃に上昇させ、80℃で6時間反応した。ゲル・パーミエーション・クロマトグラフィーによりモノマーの消失を確認し、100℃に昇温して30分間エージングを行った。100℃、減圧下でプロピレングリコールモノメチルエーテルアセテートを蒸留により取り除き、固形分濃度を30質量%に調整して、共重合体[A’−4]を含む樹脂溶液(S−4)を得た。
樹脂溶液中に含まれる共重合体[A’−4]のポリスチレン換算重量平均分子量(Mw)は8,400であり、分子量分布(Mw/Mn)は3.1であった。
(1)透明性
樹脂溶液(S−1)〜(S−4)を、ガラス基板上に膜厚3μmとなるように塗布し、オーブンにて80℃で30分間乾燥した。得られた樹脂膜付きのガラス基板について、分光光度計を使用して、波長400〜800nmでの最低透過率をガラス基板をブランクとして測定した。透過率が大きいほど透明性が高い。結果を表1に示す。
樹脂溶液(S−1)〜(S−4)を、150℃のホットプレート上に膜厚約0.5mmとなるように塗布し、ゲル化するまでの時間を測定した。時間が短いほど硬化性が良好である。結果を表1に示す。
樹脂溶液(S−1)〜(S−4)を、金属基板上に膜厚3μmとなるように塗付し、オーブンにて80℃で30分間乾燥した。乾燥した塗膜を200℃のオーブンで30分間加熱硬化させた。得られた硬化塗膜の1MHzでの誘電率を測定した。誘電率が小さいほど電気特性が良好である。結果を表1に示す。
〔実施例4〕
実施例1で得られた樹脂溶液(S−1)100質量部、1−[1−(4−ヒドロキシフェニル)イソプロピル]−4−[1,1−ビス(4−ヒドロキシフェニル)エチル]ベンゼン−1,2−ナフトキノンジアジド−5−スルホン酸エステル6.25質量部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75質量部を混合溶解し、0.2μmのメンブランフィルターで濾過を行い、溶液状態の感光性樹脂組成物(S−5)を調製した。
実施例2で得られた樹脂溶液(S−2)を用い、実施例4と同様に溶液状態の感光性樹脂組成物(S−6)を調製した。
実施例3で得られた樹脂溶液(S−3)を用い、実施例4と同様に溶液状態の感光性樹脂組成物(S−7)を調製した。
比較例1で得られた樹脂溶液(S−4)を用い、実施例4と同様に溶液状態の感光性樹脂組成物(S−8)を調製した。
(1)保存安定性
感光性樹脂組成物(S−5)〜(S−8)を室温で1ヶ月間保存した後の粘度を測定した。なお、粘度は、E型粘度計を用いて25℃で測定を行った。調製直後の粘度に対し、室温1ヶ月間保存後の粘度上昇率が10%未満の場合を○、10%以上の場合を×とした。結果を表2に示す。
感光性樹脂組成物(S−5)〜(S−8)を、ガラス基板上に膜厚3μmとなるように塗布し、オーブンにて80℃で30分間乾燥した。何れの感光性樹脂組成物でも厚さが均一な透明な樹脂膜が得られ、塗布性は良好(○)であった。
乾燥した樹脂膜にポジパターンマスクを介して超高圧水銀灯で露光し、2.38重量%テトラメチルアンモニウムヒドロキシドの水溶液にて1分間浸漬して現像し、純水でリンスを行った。何れの感光性樹脂組成物でもポジパターンが転写され、現像性は良好(○)であった。
乾燥した樹脂膜にポジパターンマスクを介さずに全面露光し、オーブンにて200℃で30分間加熱硬化させた。得られた硬化樹脂膜付きのガラス基板について、分光光度計を使用して、波長400〜800nmでの最低透過率をガラス基板をブランクとして測定した。透過率が大きいほど透明性が高い。結果を表2に示す。
200℃で30分間加熱硬化させた後、再び230℃で10時間加熱処理し、波長400nmでの透過率をガラス基板をブランクとして測定した。透過率が大きいほど耐熱変色性が高い。結果を表2に示す。
Claims (9)
- ヒドロキシフェニル(メタ)アクリレート由来の繰り返し単位と、ブロックされたイソシアネート基含有不飽和化合物由来の繰り返し単位とを含むことを特徴とする共重合体。
- 前記ヒドロキシフェニル(メタ)アクリレート由来の繰り返し単位30mol%〜90mol%と、前記ブロックされたイソシアネート基含有不飽和化合物由来の繰り返し単位10mol%〜70mol%とを含むことを特徴とする請求項1に記載の共重合体。
- 前記ブロックされたイソシアネート基含有不飽和化合物が、ブロックされた2−イソシアナトエチル(メタ)アクリレートであることを特徴とする請求項1又は2に記載の共重合体。
- 前記ブロックが、メチルエチルケトンオキシムによるものであることを特徴とする請求項1〜3の何れか一項に記載の共重合体。
- 前記ブロックされたイソシアネート基含有不飽和化合物が、2−(0−[1'−メチルプロピリデンアミノ]カルボキシアミノ)エチル(メタ)アクリレートであることを特徴とする請求項1〜4の何れか一項に記載の共重合体。
- 請求項1〜5の何れか一項に記載の共重合体及びキノンジアジド基含有化合物を含有することを特徴とする感光性樹脂組成物。
- 前記共重合体100質量部に対して、前記キノンジアジド基含有化合物を5〜60質量部含むことを特徴とする請求項6に記載の感光性樹脂組成物。
- 溶媒以外の成分の合計量100質量部に対して、溶媒を30〜4000質量部含むことを特徴とする請求項6又は7に記載の感光性樹脂組成物。
- 請求項6〜8の何れか一項に記載の感光性樹脂組成物を基板上に塗布し、乾燥して得られることを特徴とする樹脂膜。
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JP2006307129A (ja) * | 2005-03-30 | 2006-11-09 | Asahi Glass Co Ltd | 撥油性組成物および撥油膜 |
JP2007246585A (ja) * | 2006-03-14 | 2007-09-27 | Jsr Corp | 側鎖不飽和重合体、感放射線性樹脂組成物および液晶表示素子用スペーサー |
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