JP7479130B2 - エポキシアクリレート樹脂、アルカリ可溶性樹脂、それを含む樹脂組成物及びその硬化物 - Google Patents
エポキシアクリレート樹脂、アルカリ可溶性樹脂、それを含む樹脂組成物及びその硬化物 Download PDFInfo
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- JP7479130B2 JP7479130B2 JP2019171508A JP2019171508A JP7479130B2 JP 7479130 B2 JP7479130 B2 JP 7479130B2 JP 2019171508 A JP2019171508 A JP 2019171508A JP 2019171508 A JP2019171508 A JP 2019171508A JP 7479130 B2 JP7479130 B2 JP 7479130B2
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- 229920005989 resin Polymers 0.000 title claims description 64
- 239000011347 resin Substances 0.000 title claims description 64
- 239000011342 resin composition Substances 0.000 title claims description 55
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 title claims description 41
- 239000004925 Acrylic resin Substances 0.000 title claims description 36
- 239000003999 initiator Substances 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 239000010408 film Substances 0.000 description 50
- 239000003822 epoxy resin Substances 0.000 description 32
- 229920000647 polyepoxide Polymers 0.000 description 32
- -1 2,6-disubstituted phenols Chemical class 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
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- 239000000243 solution Substances 0.000 description 21
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- 239000011248 coating agent Substances 0.000 description 17
- 230000018109 developmental process Effects 0.000 description 17
- 238000011161 development Methods 0.000 description 16
- 239000005011 phenolic resin Substances 0.000 description 13
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 239000000126 substance Substances 0.000 description 11
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 10
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000007747 plating Methods 0.000 description 6
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 150000003628 tricarboxylic acids Chemical class 0.000 description 6
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
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- 238000005260 corrosion Methods 0.000 description 3
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- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
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- 150000008366 benzophenones Chemical class 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KYQRDNYMKKJUTH-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)CC1C2 KYQRDNYMKKJUTH-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XFTRTWQBIOMVPK-UHFFFAOYSA-N citramalic acid Chemical compound OC(=O)C(O)(C)CC(O)=O XFTRTWQBIOMVPK-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- PVLBGPUZWYKZAA-UHFFFAOYSA-N cyclopenta-1,3-diene 2,6-dimethylphenol Chemical compound CC1=C(C(=CC=C1)C)O.C1C=CC=C1.C1C=CC=C1 PVLBGPUZWYKZAA-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- ORBFAMHUKZLWSD-UHFFFAOYSA-N ethyl 2-(dimethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(C)C ORBFAMHUKZLWSD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical group 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- VENBJVSTINLYEU-UHFFFAOYSA-N phenol;trifluoroborane Chemical compound FB(F)F.OC1=CC=CC=C1 VENBJVSTINLYEU-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002954 polymerization reaction product Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
ここで、R1はそれぞれ独立に、炭素数1~8のアルキル基、フェニル基又はアリル基を示し、nは平均値で1~10の数を示し、Yは式(2a)で表されるLを有する不飽和結合含有基であり、Lは水素原子又は式(3)で表されるカルボキシル基含有基を示し、Lの50モル%以上は該カルボキシル基含有基である。R2は水素原子又はメチル基を示し、Mはp+1価のカルボン酸残基を示し、pは1又は2である。
少なくとも1個の重合性不飽和基を有する光重合性モノマーと、
光重合開始剤と、
を含有することを特徴とする感光性樹脂組成物である。また、本発明の他の実施形態は、上記感光性樹脂組成物を硬化させて得た硬化物に関する。
Lは全部が式(3)で表されるカルボキシル基含有基であってもよいが、分子中に、水素原子とカルボキシル基含有基の両方を有していても良い。カルボキシル基含有基は、全L中に50モル%以上であり、70~100モル%が好ましく、90~100モル%がより好ましく、100モル%が更に好ましい。多塩基酸基は、アルカリと反応性であるため、アルカリ可溶性樹脂又はその重合反応物(未硬化物)にアルカリ可溶性を与える。Lにおける多塩基酸基の存在比を変化させることにより、アルカリ可溶性を調整することができ、アルカリ現像性を最適化することができる。また、一般式(6)で表わされる多塩基酸基の種類を変化させることによっても、アルカリ現像性を初めとする樹脂特性を変化させることができる。
飽和鎖式炭化水素ジカルボン酸又はトリカルボン酸としては、コハク酸、アセチルコハク酸、アジピン酸、アゼライン酸、シトラリンゴ酸、マロン酸、グルタル酸、クエン酸、酒石酸、オキソグルタル酸、ピメリン酸、セバシン酸、スベリン酸、ジグリコール酸等の酸一無水物が含まれる。
飽和環式炭化水素ジカルボン酸又はトリカルボン酸としては、ヘキサヒドロフタル酸、シクロブタンジカルボン酸、シクロペンタンジカルボン酸、ノルボルナンジカルボン酸、ヘキサヒドロトリメリット酸等の酸一無水物が含まれる。
不飽和ジカルボン酸又はトリカルボン酸としては、マレイン酸、イタコン酸、テトラヒドロフタル酸、メチルエンドメチレンテトラヒドロフタル酸、クロレンド酸等の酸一無水物が含まれる。
その他のジカルボン酸又はトリカルボン酸としては、フタル酸、トリメリット酸等の酸無水物が含まれる。これらのなかでは、コハク酸、イタコン酸、テトラヒドロフタル酸、ヘキサヒドロトリメリット酸、フタル酸、又はトリメリット酸の酸無水物が好ましく、コハク酸、イタコン酸、又はテトラヒドロフタル酸の酸無水物がより好ましい。なお、これらのカルボン酸類は1種類で使用することも、2種類以上を併用することもできる。
エポキシアクリレート樹脂を使用した場合はアルカリ現像性を有しないが、アルカリ可溶性樹脂を使用した場合はアルカリ現像性を有し得る。
本発明の硬化性樹脂組成物は、本発明のエポキシアクリレート樹脂と重合開始剤を含む。本発明の感光性樹脂組成物は、本発明のアルカリ可溶性樹脂と光重合性モノマーと光重合開始剤を含む
(A)一般式(2)で表される1分子内にカルボキシル基及び重合性不飽和基を有するアルカリ可溶性樹脂、
(B)少なくとも1個の重合性不飽和基を有する光重合性モノマー、
(C)光重合開始剤、
(D)エポキシ樹脂
光重合開始剤の添加量は、(A)アルカリ可溶性樹脂と(B)光重合性モノマーの合計量100質量部に対して、0.1~10質量部が好ましく、2~5質量部がより好ましい。ここで、光重合開始剤の添加量が0.1質量部未満であると感度が十分に得られず、光重合開始剤の添加量が10質量部を超えるとテーパー形状(現像パターン断面の膜厚方向形状)がシャープにならないで裾を引いた状態になるハレーションが起こりやすくなる。更に、後工程で高温に暴露した場合に分解ガスが発生するおそれがある。
固形分濃度は、実施例1(及び比較例1)中で得られた樹脂溶液、感光性樹脂組成物等(1g)をガラスフィルター〔質量:W0(g)〕に含浸させて秤量し〔W1(g)〕、160℃で2時間加熱した後の質量〔W2(g)〕の値を用いて下記式より算出した。
固形分濃度(%)=100×(W2-W0)/(W1-W0)
JIS K 0070規格に準拠して測定した。具体的には、樹脂溶液をジオキサンに溶解させ、電位差滴定装置「COM-1600」(平沼産業株式会社製)を用いて0.1N-KOH水溶液で滴定して、固形分1gあたりに必要としたKOHの量を酸価とした。
分子量は、ゲルパーミュエーションクロマトグラフィー(GPC)(「HLC-8220GPC」東ソー株式会社製、カラム:TSKgelSuperH2000(2本)+TSKgelSuperH3000(1本)+TSKgelSuperH4000(1本)+TSKgelSuperH5000(1本)(いずれも東ソー株式会社製)、溶媒:テトラヒドロフラン、温度:40℃、速度:0.6mL/min)にて測定し、標準ポリスチレン(「PS-オリゴマーキット」東ソー株式会社製)換算値として求めた値を重量平均分子量(Mw)とした。
空洞共振法(ベクトルネットワークアナライザー(VNA)E8363B(アジレント・テクノロジー製)、空洞共振器摂動法誘電率測定装置(関東電子応用開発製))を用いて、絶乾後23℃、湿度50%の室内に24時間保管した後の、1GHzの値を測定した。
硬化膜付きガラス基板の膜上に少なくとも100個の碁盤目状になるようにクロスカットを入れて、次いでセロハンテープを用いてピーリング試験を行い、碁盤目の状態を目視によって評価した。
◎:全く剥離がみられないもの
○:僅かに塗膜に剥離が確認できるもの
△:一部塗膜に剥離が確認できるもの
×:膜が殆ど剥離してしまうもの
硬化膜付きガラス基板を、2-アミノエタノール30部、グリコールエーテル70部の混合液の80℃に保持した溶液に浸漬し、10分後に引き上げて純水で洗浄、乾燥して、薬品浸漬したサンプルを作製して、上記密着性を評価した。
硬化膜付きガラス基板を、王水(塩酸:硝酸=7:3)の50℃に保持した溶液に浸漬し、10分後に引き上げて純水で洗浄、乾燥して、薬品浸漬したサンプルを作製して、上記密着性を評価した。
E1:2,6-キシレノール・ジシクロペンタジエン型エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YDDP-100、エポキシ当量271g/eq.)
E2:フェノールノボラック型エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YDPN-638、エポキシ当量177g/eq.)
E3:ビスフェノールA型液状エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YD-127、エポキシ当量182g/eq.)
E4:クレゾールノボラック型エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YDCN-700-3、エポキシ当量203g/eq.、軟化点73℃)
THPA:1,2,3,6-テトラヒドロフタル酸無水物
TPP:トリフェニルホスフィン
HQ:ハイドロキノン
TEAB:臭化テトラエチルアンモニウム
PGMEA:プロピレングリコールモノメチルエーテルアセテート
R1:実施例1で得られたエポキシアクリレート樹脂
HR1:比較例1で得られたエポキシアクリレート樹脂
A1:実施例2で得られたアルカリ可溶性樹脂
HA1:比較例2で得られたアルカリ可溶性樹脂
HA2:比較例3で得られたアルカリ可溶性樹脂
B1:ジペンタエリスリトールヘキサアクリレート
C1:光重合開始剤(BASF社製、イルガキュア184)
C2:光重合開始剤(4,4’-ビス(ジメチルアミノ)ベンゾフェノン(ミヒラーケトン))
撹拌機、温度調節装置、還流冷却器、及び空気導入装置を備えた反応容器に、271部のE1を61部のPGMEAに溶解し、更にアクリル酸72部、TPP3.5部、HQ0.1部を加えて、空気を吹きこみながら、110℃で8時間反応させた後、PGMEA285部加えて、エポキシアクリレート樹脂(R1)のPGMEA溶液を得た。得られた樹脂溶液の固形分濃度は50%であった。
実施例1と同様の装置に、177部のE2を44部のPGMEAに溶解し、更にアクリル酸72部、TPP3.5部、HQ0.1部を加えて、空気を吹きこみながら、110℃で8時間反応させた後、PGMEA208部加えて、エポキシアクリレート樹脂(HR1)のPGMEA溶液を得た。得られた樹脂溶液の固形分濃度は50%であった。実施例1と同様の操作を行い、試験片を作成し、比誘電率及び誘電正接を測定し、結果を表1に示した。
実施例1と同様の装置に、R1の50%PGMEA溶液450部と、THPA98部と、TEAB1.8部と、PGMEA40部とを仕込み、120~125℃で6時間撹拌し、アルカリ可溶性樹脂溶液(A1)を得た。得られた樹脂溶液の固形分濃度は55%、酸価(固形分換算)は113mgKOH/g、分子量(Mw)は890であった。
実施例1と同様の装置に、HR1の50%PGMEA溶液450部と、THPA135部と、TEAB1.8部と、PGMEA70部とを仕込み、120~125℃で6時間撹拌し、アルカリ可溶性樹脂溶液(HA1)を得た。得られた樹脂溶液の固形分濃度は55%、酸価(固形分換算)は138mgKOH/g、分子量(Mw)は1450であった。
実施例1と同様の装置に、182部のE3を45部のPGMEAに溶解し、更にアクリル酸72部、TPP3.5部、HQ0.1部を加えて、空気を吹きこみながら、110℃で8時間反応させた後、PGMEA212部加えて、エポキシアクリレート樹脂のPGMEA溶液を得た。得られた樹脂溶液の固形分濃度は50%であった。得られた樹脂溶液291部と、ジメチロールプロピオン酸4.0部と、1,6-ヘキサンジオール11.8部と、PGMEA84部とを仕込み、45℃に昇温した。次に、イソホロンジイソシアネート61.8部を温度に注意しながら滴下した。滴下終了後、75~80℃で6時間撹拌した。更に、THPA21部を仕込み、90~95℃で6時間撹拌し、アルカリ可溶性樹脂溶液(HA2)を得た。得られた樹脂溶液の固形分濃度は66%、酸価(固形分換算)は38.4mgKOH/g、分子量(Mw)は12220であった。
Claims (9)
- 請求項1に記載のエポキシアクリレート樹脂と重合開始剤とを含有することを特徴とする硬化性樹脂組成物。
- 請求項2に記載のアルカリ可溶性樹脂と、少なくとも1個の重合性不飽和基を有する光重合性モノマーと、光重合開始剤とを含有することを特徴とする感光性樹脂組成物。
- 請求項4に記載の感光性樹脂組成物に、更にエポキシ化合物を含有することを特徴とする感光性樹脂組成物。
- アルカリ可溶性樹脂と光重合性モノマーの合計100質量部に対して、光重合開始剤を0.1~10質量部含有する請求項4又は5に記載の感光性樹脂組成物。
- アルカリ可溶性樹脂と光重合性モノマーの合計100質量部に対して、エポキシ化合物を10~40質量部含有する請求項5又は6に記載の感光性樹脂組成物。
- 請求項3に記載の硬化性樹脂組成物を硬化させた硬化物。
- 請求項4~7のいずれか一項に記載の感光性樹脂組成物を硬化させた硬化物。
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