JP2016048305A - Photosensitive resin composition for forming interlayer insulation film, interlayer insulation film, and method for forming interlayer insulation film - Google Patents
Photosensitive resin composition for forming interlayer insulation film, interlayer insulation film, and method for forming interlayer insulation film Download PDFInfo
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- JP2016048305A JP2016048305A JP2014173128A JP2014173128A JP2016048305A JP 2016048305 A JP2016048305 A JP 2016048305A JP 2014173128 A JP2014173128 A JP 2014173128A JP 2014173128 A JP2014173128 A JP 2014173128A JP 2016048305 A JP2016048305 A JP 2016048305A
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- Prior art keywords
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- resin composition
- photosensitive resin
- insulating film
- interlayer insulating
- Prior art date
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- 239000011229 interlayer Substances 0.000 title claims abstract description 68
- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 238000009413 insulation Methods 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 12
- -1 isocyanate compound Chemical class 0.000 claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000012948 isocyanate Substances 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 18
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 17
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 238000013007 heat curing Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 239000003504 photosensitizing agent Substances 0.000 abstract description 5
- 229920001577 copolymer Polymers 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 239000002981 blocking agent Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000047 product Substances 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
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 4
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 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 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical compound FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 description 2
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- XHHCPUPIFYYPCN-UHFFFAOYSA-N 4-[bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)methyl]benzene-1,2-diol Chemical compound CC1=CC(O)=C(C2CCCCC2)C=C1C(C=1C(=CC(O)=C(C2CCCCC2)C=1)C)C1=CC=C(O)C(O)=C1 XHHCPUPIFYYPCN-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
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- 235000004515 gallic acid Nutrition 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 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 2
- 239000000463 material Substances 0.000 description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
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- SVHAMPNLOLKSFU-UHFFFAOYSA-N 1,2,2-trichloroethenylbenzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1 SVHAMPNLOLKSFU-UHFFFAOYSA-N 0.000 description 1
- AUHKVLIZXLBQSR-UHFFFAOYSA-N 1,2-dichloro-3-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC(Cl)=C1Cl AUHKVLIZXLBQSR-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- XPXMCUKPGZUFGR-UHFFFAOYSA-N 1-chloro-2-(1,2,2-trichloroethenyl)benzene Chemical compound ClC(Cl)=C(Cl)C1=CC=CC=C1Cl XPXMCUKPGZUFGR-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
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- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- ZQMAPKVSTSACQB-UHFFFAOYSA-N prop-2-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC=C ZQMAPKVSTSACQB-UHFFFAOYSA-N 0.000 description 1
- HAFZJTKIBGEQKT-UHFFFAOYSA-N prop-2-enyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC=C HAFZJTKIBGEQKT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 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
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000013638 trimer Substances 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
本発明は、層間絶縁膜形成用感光性樹脂組成物、層間絶縁膜及び層間絶縁膜の形成方法に関する。 The present invention relates to a photosensitive resin composition for forming an interlayer insulating film, an interlayer insulating film, and a method for forming an interlayer insulating film.
近年、半導体素子の高集積化、大型化が進み、パッケージ基板のより一層の薄型化、小型化への要求がある。これに伴い、半導体素子の表面保護層、層間絶縁膜、又は再配線層を有するパッケージ基板の層間絶縁膜を、より優れた電気特性、耐熱性、機械特性等を併せ持つ材料により形成することが求められている。 In recent years, semiconductor devices have been highly integrated and increased in size, and there is a demand for further thinner and smaller package substrates. Along with this, it is required to form a surface protection layer of a semiconductor element, an interlayer insulation film, or an interlayer insulation film of a package substrate having a rewiring layer with a material having more excellent electrical characteristics, heat resistance, mechanical characteristics, etc. It has been.
ポリイミド樹脂(以下、「PI」という。)やポリベンズオキサゾール(以下、「PBO」という。)はそのような要求特性を満足し得る材料の代表であり、例えば、PIやPBOに感光特性を付与した感光性PIや感光性PBOの使用が検討されている。これらの感光性樹脂を用いると、パターン形成工程が簡略化されて煩雑な製造工程が短縮できるという利点があるうえ、従来のカルボキシル基を導入しアルカリ現像可能としたビニル系の感光性樹脂に比べ耐熱性や絶縁抵抗が高いため、上記層間絶縁膜として有効である(例えば、特許文献1、2参照)。 Polyimide resin (hereinafter referred to as “PI”) and polybenzoxazole (hereinafter referred to as “PBO”) are representative of materials that can satisfy such required characteristics. For example, photosensitive properties are imparted to PI and PBO. The use of photosensitive PI and photosensitive PBO that have been used has been studied. The use of these photosensitive resins has the advantage that the pattern formation process is simplified and the complicated manufacturing process can be shortened. In addition, compared with conventional vinyl-based photosensitive resins that can be alkali-developed by introducing a carboxyl group. Since it has high heat resistance and insulation resistance, it is effective as the interlayer insulating film (see, for example, Patent Documents 1 and 2).
一方、感光性PIや感光性PBOは、高温(350〜400℃)での焼成が必要であることや、経時安定性が良好でない、形成した樹脂膜の膜べりが大きい、溶剤溶解性が低い等の問題があった。 On the other hand, photosensitive PI and photosensitive PBO require firing at a high temperature (350 to 400 ° C.), have poor stability over time, have a large thickness of the formed resin film, and have low solvent solubility. There was a problem such as.
これに対し、耐熱性が高く、且つ取り扱い性も良好な感光性アクリル樹脂を用いた層間絶縁膜が提案されている(特許文献3等)。しかしながら、この感光性アクリル樹脂を用いた層間絶縁膜は、機械特性等に未だ改良の余地があった。 On the other hand, an interlayer insulating film using a photosensitive acrylic resin having high heat resistance and good handleability has been proposed (Patent Document 3 and the like). However, the interlayer insulating film using the photosensitive acrylic resin still has room for improvement in mechanical characteristics and the like.
本発明は、上記事情に鑑みてなされたものであり、機械特性が良好である層間絶縁膜を形成可能な感光性樹脂組成物の提供を目的とする。 This invention is made | formed in view of the said situation, and it aims at provision of the photosensitive resin composition which can form the interlayer insulation film with favorable mechanical characteristics.
本発明の第一の態様は、アルカリ可溶性樹脂(A)と、感光剤(B)と、シランカップリング剤(C)と、架橋剤(D)と、を含有する層間絶縁膜形成用感光性樹脂組成物であって、前記架橋剤(D)が、オキセタン含有化合物、エポキシ基含有化合物及びブロックイソシアネート化合物からなる群から選択される少なくとも1種であることを特徴とする層間絶縁膜形成用感光性樹脂組成物である。
本発明の第二の態様は、前記第一の態様の層間絶縁膜形成用感光性樹脂組成物を用いた層間絶縁膜である。
本発明の第三の態様は、支持体上に、前記第一の態様の層間絶縁膜形成用感光性樹脂組成物を用いて感光性樹脂組成物層を形成する工程と、前記感光性樹脂組成物層を露光する工程と、露光された前記感光性樹脂組成物層を現像して層間絶縁膜パターンを形成する工程と、前記層間絶縁膜パターンを加熱硬化する工程と、を有する層間絶縁膜の形成方法である。
The first aspect of the present invention is an interlayer insulating film forming photosensitizer comprising an alkali-soluble resin (A), a photosensitizer (B), a silane coupling agent (C), and a cross-linking agent (D). A resin composition for forming an interlayer insulating film, wherein the crosslinking agent (D) is at least one selected from the group consisting of an oxetane-containing compound, an epoxy group-containing compound, and a blocked isocyanate compound. It is an adhesive resin composition.
A second aspect of the present invention is an interlayer insulating film using the photosensitive resin composition for forming an interlayer insulating film according to the first aspect.
A third aspect of the present invention includes a step of forming a photosensitive resin composition layer on a support using the photosensitive resin composition for forming an interlayer insulating film according to the first aspect, and the photosensitive resin composition An interlayer insulating film comprising: exposing a physical layer; developing the exposed photosensitive resin composition layer to form an interlayer insulating film pattern; and heating and curing the interlayer insulating film pattern. It is a forming method.
本発明によれば、機械特性等が良好である層間絶縁膜を形成可能な感光性樹脂組成物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the photosensitive resin composition which can form the interlayer insulation film with favorable mechanical characteristics etc. can be provided.
以下、本発明の実施態様について詳細に説明するが、本発明は、以下の実施態様に何ら限定されるものではなく、本発明の目的の範囲内において、適宜変更を加えて実施することができる。 Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments, and can be implemented with appropriate modifications within the scope of the object of the present invention. .
≪層間絶縁膜形成用感光性樹脂組成物≫
本発明の第一の態様は、アルカリ可溶性樹脂(A)と、感光剤(B)と、シランカップリング剤(C)と、架橋剤(D)と、を含有する層間絶縁膜形成用感光性樹脂組成物であって、前記架橋剤(D)が、オキセタン含有化合物、エポキシ基含有化合物及びブロックイソシアネート化合物からなる群から選択される少なくとも1種であることを特徴とする層間絶縁膜形成用感光性樹脂組成物である。
≪Photosensitive resin composition for forming interlayer insulating film≫
The first aspect of the present invention is an interlayer insulating film forming photosensitizer comprising an alkali-soluble resin (A), a photosensitizer (B), a silane coupling agent (C), and a cross-linking agent (D). A resin composition for forming an interlayer insulating film, wherein the crosslinking agent (D) is at least one selected from the group consisting of an oxetane-containing compound, an epoxy group-containing compound, and a blocked isocyanate compound. It is an adhesive resin composition.
[アルカリ可溶性樹脂(A)]
アルカリ可溶性樹脂としては、アルカリに対する溶解性を有するアルカリ可溶性基を有する任意の樹脂を採用できる。
該アルカリ可溶性樹脂(A)(以下、「共重合体(A)」と記載することがある。)としては、例えば、アクリル系樹脂が好適に用いられる。
アクリル系樹脂としては、一般式(a−1)で表される構成単位(A1)又は脂環式エポキシ基含有単位(A3)を含有することが好ましい。
[Alkali-soluble resin (A)]
As the alkali-soluble resin, any resin having an alkali-soluble group having solubility in alkali can be employed.
As the alkali-soluble resin (A) (hereinafter sometimes referred to as “copolymer (A)”), for example, an acrylic resin is preferably used.
As acrylic resin, it is preferable to contain the structural unit (A1) represented by general formula (a-1), or an alicyclic epoxy group containing unit (A3).
〔構成単位(A1)〕
構成単位(A1)は、下記一般式(a−1)で表される。
[Structural unit (A1)]
The structural unit (A1) is represented by the following general formula (a-1).
一般式(a−1)中、Rは水素原子又はメチル基を表す。
一般式(a−1)中、Ra01は水素原子又は水酸基を有する有機基である。
ここで、有機基とは、例えば、分岐状、直鎖状、又は環状のアルキル基、置換基を有していてもよいアリール基、置換基を有していてもよいヘテロアリール基、置換基を有していてもよいアラルキル基、又は置換基を有していてもよいヘテロアラルキル基を挙げることができ、Ra01は、その構造中に少なくとも一つの水酸基を有する。前記有機基の炭素数は1〜20であることが好ましく、6〜12であることが更に好ましい。炭素数が大きいと保存安定性や層間絶縁層の低誘電率化の面で好ましく、炭素数が小さいと解像性に優れる。
In general formula (a-1), R represents a hydrogen atom or a methyl group.
In general formula (a-1), Ra 01 is a hydrogen atom or an organic group having a hydroxyl group.
Here, the organic group is, for example, a branched, linear, or cyclic alkyl group, an aryl group that may have a substituent, a heteroaryl group that may have a substituent, or a substituent. An aralkyl group which may have a substituent, or a heteroaralkyl group which may have a substituent, and Ra 01 has at least one hydroxyl group in its structure. The organic group preferably has 1 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. A large carbon number is preferable in terms of storage stability and low dielectric constant of the interlayer insulating layer, and a small carbon number is excellent in resolution.
なお、構成単位(A1)として、Ra01が水素原子の場合、即ち、メタクリル酸やアクリル酸等を選択することも共重合体のアルカリ現像性を高める上で有効であるが、保存安定性の面から、構成単位(A1)として、上記の水酸基を有する有機基を採用することが好ましい。 As the structural unit (A1), when Ra 01 is a hydrogen atom, that is, selecting methacrylic acid or acrylic acid is effective in enhancing the alkali developability of the copolymer. From the standpoint, it is preferable to employ the above organic group having a hydroxyl group as the structural unit (A1).
構成単位(A1)として好ましい例として、下記一般式(a−1−1)で表される構成単位を挙げることができる。 Preferred examples of the structural unit (A1) include structural units represented by the following general formula (a-1-1).
一般式(a−1−1)において、Rは水素原子又はメチル基を挙げることができ、メチル基であることが好ましい。
また、Ya01は単結合又は炭素数1〜5の直鎖状若しくは分岐状のアルキレン基を示す。具体的には、メチレン基、エチレン基、プロピレン基、イソプロピレン基、n−ブチレン基、イソブチレン基、tert−ブチレン基、ペンチレン基、イソペンチレン基、ネオペンチレン基等が挙げられる。中でも、単結合、メチレン基、エチレン基であることが好ましい。
Ya01は、アルカリ可溶性を向上させることができることと、更に層間絶縁膜としたときの耐熱性が向上することから、単結合であることが好ましい。
In general formula (a-1-1), R can include a hydrogen atom or a methyl group, and is preferably a methyl group.
Ya 01 represents a single bond or a linear or branched alkylene group having 1 to 5 carbon atoms. Specific examples include a methylene group, an ethylene group, a propylene group, an isopropylene group, an n-butylene group, an isobutylene group, a tert-butylene group, a pentylene group, an isopentylene group, and a neopentylene group. Among these, a single bond, a methylene group, and an ethylene group are preferable.
Ya 01 is preferably a single bond because it can improve alkali solubility and further improve the heat resistance when used as an interlayer insulating film.
ここで、aは1〜5の整数を表すが、本発明の効果の観点や、製造が容易であるという点から、aが1であることが好ましい。また、ベンゼン環における水酸基の結合位置は、Ya01と結合している炭素原子を基準(1位)としたとき、4位に結合していることが好ましい。 Here, a represents an integer of 1 to 5, and it is preferable that a is 1 from the viewpoint of the effect of the present invention and the point that the production is easy. Further, the bonding position of the hydroxyl group in the benzene ring is preferably bonded to the 4-position when the carbon atom bonded to Ya 01 is the reference (first position).
また、Ra001は炭素数1〜5の直鎖状又は分岐状のアルキル基である。具体的には、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基等が挙げられる。中でも製造が容易であるという点から、メチル基又はエチル基であることが好ましい。
ここで、bは0又は1〜4の整数を表すが、本発明の効果の観点や、製造が容易であるという点から、bは0であることが好ましい。
Ra 001 is a linear or branched alkyl group having 1 to 5 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a neopentyl group. Among these, a methyl group or an ethyl group is preferable from the viewpoint of easy production.
Here, b represents 0 or an integer of 1 to 4, but b is preferably 0 from the viewpoint of the effect of the present invention and the ease of production.
構成単位(A1)として、更に具体的には、o−ヒドロキシフェニル(メタ)アクリレート、m−ヒドロキシフェニル(メタ)アクリレート、p−ヒドロキシフェニル(メタ)アクリレート、o−ヒドロキシベンジル(メタ)アクリレート、m−ヒドロキシベンジル(メタ)アクリレート、p−ヒドロキシベンジル(メタ)アクリレート、o−ヒドロキシフェニルエチル(メタ)アクリレート、m−ヒドロキシフェニルエチル(メタ)アクリレート、p−ヒドロキシフェニルエチル(メタ)アクリレート等が挙げられ、p−ヒドロキシフェニル(メタ)アクリレートまたはp−ヒドロキシベンジル(メタ)アクリレートが好ましく、特に、p−ヒドロキシフェニル(メタ)アクリレートが好ましい。 As the structural unit (A1), more specifically, o-hydroxyphenyl (meth) acrylate, m-hydroxyphenyl (meth) acrylate, p-hydroxyphenyl (meth) acrylate, o-hydroxybenzyl (meth) acrylate, m -Hydroxybenzyl (meth) acrylate, p-hydroxybenzyl (meth) acrylate, o-hydroxyphenylethyl (meth) acrylate, m-hydroxyphenylethyl (meth) acrylate, p-hydroxyphenylethyl (meth) acrylate, etc. , P-hydroxyphenyl (meth) acrylate or p-hydroxybenzyl (meth) acrylate is preferable, and p-hydroxyphenyl (meth) acrylate is particularly preferable.
共重合体における前記構成単位(A1)の含有比率は、10〜70モル%であることが好ましい。更に、15〜60モル%であることが好ましく、20〜50モル%であることが最も好ましい。 The content ratio of the structural unit (A1) in the copolymer is preferably 10 to 70 mol%. Furthermore, it is preferable that it is 15-60 mol%, and it is most preferable that it is 20-50 mol%.
〔脂環式エポキシ基含有単位(A3)〕
また、脂環式エポキシ基含有単位(A3)としては、脂環式エポキシ基を構造中に有し、エチレン性二重結合を有する化合物から誘導される構成単位であれば、特に限定されない。脂環式エポキシ基の脂環式基の炭素数は、5〜10程度が好ましい。本発明の共重合体が脂環式エポキシ基含有単位(A3)を有することで、アウトガス発生の原因となる低分子量架橋成分を感光性樹脂組成物に添加せずとも、その耐熱性を向上することが可能となる。
[Alicyclic epoxy group-containing unit (A3)]
The alicyclic epoxy group-containing unit (A3) is not particularly limited as long as it is a structural unit having an alicyclic epoxy group in the structure and derived from a compound having an ethylenic double bond. As for carbon number of the alicyclic group of an alicyclic epoxy group, about 5-10 are preferable. By having the alicyclic epoxy group-containing unit (A3) in the copolymer of the present invention, the heat resistance is improved without adding a low molecular weight crosslinking component that causes outgassing to the photosensitive resin composition. It becomes possible.
具体的な脂環式エポキシ基含有単位(A3)として、例えば、以下の一般式(1)〜(31)で示される脂環式エポキシ基含有重合性不飽和化合物から誘導されるものが挙げられる。 Specific examples of the alicyclic epoxy group-containing unit (A3) include those derived from alicyclic epoxy group-containing polymerizable unsaturated compounds represented by the following general formulas (1) to (31). .
式中、R4は水素原子又はメチル基を示し、R5は炭素数1〜8の2価の炭化水素基を示し、R6は炭素数1〜20の2価の炭化水素基を示し、R4、R5及びR6は同一又は異なってもよく、wは0〜10の整数を示す。 In the formula, R 4 represents a hydrogen atom or a methyl group, R 5 represents a divalent hydrocarbon group having 1 to 8 carbon atoms, R 6 represents a divalent hydrocarbon group having 1 to 20 carbon atoms, R 4 , R 5 and R 6 may be the same or different, and w represents an integer of 0 to 10.
これらの中でも、一般式(1)〜(6)、(14)、(16)、(18)、(21)、(23)〜(25)、(30)で表されるものが望ましい。更に好ましくは、一般式(1)〜(6)である。 Among these, those represented by the general formulas (1) to (6), (14), (16), (18), (21), (23) to (25), and (30) are preferable. More preferably, they are general formula (1)-(6).
共重合体における前記脂環式エポキシ基含有単位(A3)の含有比率は、5〜40モル%であることが好ましい。更に、10〜30モル%であることが好ましく、15〜25モル%であることが最も好ましい。その含有比率が10モル%以上であれば、層間絶縁膜の耐熱性や密着性を高めることができ、40モル%未満であると層間絶縁膜の誘電率を低く抑えることができる。 The content ratio of the alicyclic epoxy group-containing unit (A3) in the copolymer is preferably 5 to 40 mol%. Furthermore, it is preferable that it is 10-30 mol%, and it is most preferable that it is 15-25 mol%. If the content ratio is 10 mol% or more, the heat resistance and adhesion of the interlayer insulating film can be improved, and if it is less than 40 mol%, the dielectric constant of the interlayer insulating film can be kept low.
〔構成単位(A2)〕
また、上記共重合体は一般式(a−2)で表される構成単位(A2)を有することが好ましい。
[Structural unit (A2)]
Moreover, it is preferable that the said copolymer has a structural unit (A2) represented by general formula (a-2).
Rbの炭化水素基としては、例えば、分岐状、直鎖状、若しくは環状のアルキル基、置換基を有していてもよいアリール基、又は置換基を有していてもよいアラルキル基を挙げることができる。前記炭化水素基の炭素数は1〜20であることが好ましい。更に、分岐状、直鎖状のアルキル基としては、炭素数1〜12が好ましく、1〜6が最も好ましい。環状のアルキル基としては、炭素数6〜20が好ましく、6〜12が最も好ましい。置換基を有していてもよいアリール基、又は置換基を有していてもよいアラルキル基としては、炭素数6〜20が好ましく、6〜12が最も好ましい。炭素数が20以下であればアルカリ解像性は十分であり、炭素数が1以上であれば層間絶縁膜の誘電率を低減できて好ましい。 Examples of the hydrocarbon group for Rb include a branched, linear, or cyclic alkyl group, an aryl group that may have a substituent, or an aralkyl group that may have a substituent. Can do. The hydrocarbon group preferably has 1 to 20 carbon atoms. Furthermore, as a branched and linear alkyl group, C1-C12 is preferable and 1-6 are the most preferable. The cyclic alkyl group preferably has 6 to 20 carbon atoms, and most preferably 6 to 12 carbon atoms. The aryl group which may have a substituent or the aralkyl group which may have a substituent preferably has 6 to 20 carbon atoms, and most preferably 6 to 12 carbon atoms. Alkali resolution is sufficient if the carbon number is 20 or less, and it is preferable if the carbon number is 1 or more because the dielectric constant of the interlayer insulating film can be reduced.
構成単位(A2)として具体的には、メチルアクリレート、エチルアクリレート、プロピルアクリレート、イソプロピルアクリレート、ブチルアクリレート、アミルアクリレート、エチルヘキシルアクリレート、オクチルアクリレート、t−オクチルアクリレート等の直鎖あるいは分岐鎖アルキルアクリレート;シクロヘキシルアクリレート、ジシクロペンタニルアクリレート、2−メチルシクロヘキシルアクリレート、イソボルニルアクリレート等の脂環式アルキルアクリレート;ベンジルアクリレート、アリールアクリレート(例えば、フェニルアクリレート)等から誘導されるものが挙げられる。 Specific examples of the structural unit (A2) include linear or branched alkyl acrylates such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, amyl acrylate, ethyl hexyl acrylate, octyl acrylate, and t-octyl acrylate; cyclohexyl Examples thereof include alicyclic alkyl acrylates such as acrylate, dicyclopentanyl acrylate, 2-methylcyclohexyl acrylate, and isobornyl acrylate; those derived from benzyl acrylate, aryl acrylate (for example, phenyl acrylate), and the like.
あるいは、メチルメタクリレート、エチルメタクリレート、プロピルメタクリレート、イソプロピルメタクリレート、n−ブチルメタクリレート、sec−ブチルメタクリレート、t−ブチルメタクリレート、アミルメタクリレート、ヘキシルメタクリレート、オクチルメタクリレート等の直鎖又は分岐鎖アルキルメタクリレート;シクロヘキシルメタクリレート、ジシクロペンタニルメタクリレート、2−メチルシクロヘキシルメタクリレート、イソボルニルメタクリレート等の脂環式アルキルメタクリレート;ベンジルメタクリレート、アリールメタクリレート(例えばフェニルメタクリレート、クレジルメタクリレート、ナフチルメタクリレート等)等から誘導されるものが挙げられる。 Alternatively, linear or branched alkyl methacrylates such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, t-butyl methacrylate, amyl methacrylate, hexyl methacrylate, octyl methacrylate; cyclohexyl methacrylate, Alicyclic alkyl methacrylates such as dicyclopentanyl methacrylate, 2-methylcyclohexyl methacrylate, and isobornyl methacrylate; those derived from benzyl methacrylate, aryl methacrylate (eg, phenyl methacrylate, cresyl methacrylate, naphthyl methacrylate, etc.) It is done.
上記構成単位(A2)を共重合体に導入することにより、共重合体の溶解スピードを調整することができる。構成単位(A2)としては、特に脂環式の基を有する単量体から誘導されるものが、層間絶縁膜の低誘電率化の面から好ましい。 By introducing the structural unit (A2) into the copolymer, the dissolution speed of the copolymer can be adjusted. As the structural unit (A2), those derived from a monomer having an alicyclic group are particularly preferred from the viewpoint of reducing the dielectric constant of the interlayer insulating film.
共重合体における構成単位(A2)の含有比率は、5〜50モル%であることが好ましい。 The content ratio of the structural unit (A2) in the copolymer is preferably 5 to 50 mol%.
〔構成単位(A4)〕
また、上記共重合体には、本発明の目的に反しない範囲で構成単位(A1)〜(A3)以外の構成単位(A4)を含有していてもよい。この構成単位は、エチレン性二重結合を有する化合物から誘導される構成単位であれば、特に限定されない。このような構成単位としては、例えば、アクリルアミド類、メタクリルアミド類、アリル化合物、ビニルエーテル類、ビニルエステル類、及びスチレン類等から選ばれる構成単位が挙げられる。
[Structural unit (A4)]
Further, the copolymer may contain a structural unit (A4) other than the structural units (A1) to (A3) as long as the object of the present invention is not violated. The structural unit is not particularly limited as long as it is a structural unit derived from a compound having an ethylenic double bond. Examples of such structural units include structural units selected from acrylamides, methacrylamides, allyl compounds, vinyl ethers, vinyl esters, styrenes, and the like.
アクリルアミド類としては、具体的には、アクリルアミド、N−アルキルアクリルアミド(アルキル基の炭素数は1〜10が好ましく、例えばメチル基、エチル基、プロピル基、ブチル基、t−ブチル基、ヘプチル基、オクチル基、シクロヘキシル基、ヒドロキシエチル基、ベンジル基等が挙げられる)、N−アリールアクリルアミド(アリール基としては、例えばフェニル基、トリル基、ニトロフェニル基、ナフチル基、ヒドロキシフェニル基等)、N,N−ジアルキルアクリルアミド(アルキル基の炭素数は1〜10が好ましい)、N,N−アリールアクリルアミド(アリール基としては、例えばフェニル基がある)、N−メチル−N−フェニルアクリルアミド、N−ヒドロキシエチル−N−メチルアクリルアミド、N−2−アセトアミドエチル−N−アセチルアクリルアミドが挙げられる。 Specific examples of acrylamides include acrylamide and N-alkylacrylamide (the alkyl group preferably has 1 to 10 carbon atoms, such as methyl, ethyl, propyl, butyl, t-butyl, heptyl, Octyl group, cyclohexyl group, hydroxyethyl group, benzyl group and the like), N-arylacrylamide (as the aryl group, for example, phenyl group, tolyl group, nitrophenyl group, naphthyl group, hydroxyphenyl group, etc.), N, N-dialkylacrylamide (the alkyl group preferably has 1 to 10 carbon atoms), N, N-arylacrylamide (the aryl group includes, for example, a phenyl group), N-methyl-N-phenylacrylamide, N-hydroxyethyl -N-methylacrylamide, N-2-acetoami Ethyl -N- acetyl acrylamide.
メタクリルアミド類としては、具体的には、メタクリルアミド、N−アルキルメタクリルアミド(アルキル基としては、炭素数1〜10のものが好ましく、例えばメチル基、エチル基、t−ブチル基、エチルヘキシル基、ヒドロキシエチル基、シクロヘキシル基等が挙げられる)、N−アリールメタクリルアミド(アリール基としては、フェニル基等がある。)、N,N−ジアルキルメタクリルアミド(アルキル基としては、エチル基、プロピル基、ブチル基等がある)、N,N−ジアリールメタクリルアミド(アリール基としては、フェニル基等がある)、N−ヒドロキシエチル−N−メチルメタクリルアミド、N−メチル−N−フェニルメタクリルアミド、N−エチル−N−フェニルメタクリルアミドが挙げられる。 Specific examples of the methacrylamides include methacrylamide, N-alkylmethacrylamide (the alkyl group preferably has 1 to 10 carbon atoms, such as a methyl group, an ethyl group, a t-butyl group, an ethylhexyl group, Hydroxyethyl group, cyclohexyl group and the like), N-aryl methacrylamide (the aryl group includes a phenyl group), N, N-dialkyl methacrylamide (the alkyl group includes an ethyl group, a propyl group, Butyl group and the like), N, N-diarylmethacrylamide (the aryl group includes phenyl group and the like), N-hydroxyethyl-N-methylmethacrylamide, N-methyl-N-phenylmethacrylamide, N- And ethyl-N-phenylmethacrylamide.
アリル化合物としては、具体的には、アリルエステル類(例えば酢酸アリル、カプロン酸アリル、カプリル酸アリル、ラウリン酸アリル、パルミチン酸アリル、ステアリン酸アリル、安息香酸アリル、アセト酢酸アリル、乳酸アリル等)、アリルオキシエタノール等が挙げられる。 Specific examples of allyl compounds include allyl esters (eg, allyl acetate, allyl caproate, allyl caprylate, allyl laurate, allyl palmitate, allyl stearate, allyl benzoate, allyl acetoacetate, allyl lactate, etc.) And allyloxyethanol.
ビニルエーテル類としては、具体的には、アルキルビニルエーテル(例えばヘキシルビニルエーテル、オクチルビニルエーテル、デシルビニルエーテル、エチルヘキシルビニルエーテル、メトキシエチルビニルエーテル、エトキシエチルビニルエーテル、クロルエチルビニルエーテル、1−メチル−2,2−ジメチルプロピルビニルエーテル、2−エチルブチルビニルエーテル、ヒドロキシエチルビニルエーテル、ジエチレングリコールビニルエーテル、ジメチルアミノエチルビニルエーテル、ジエチルアミノエチルビニルエーテル、ブチルアミノエチルビニルエーテル、ベンジルビニルエーテル、テトラヒドロフルフリルビニルエーテル等)、ビニルアリールエーテル(例えばビニルフェニルエーテル、ビニルトリルエーテル、ビニルクロルフェニルエーテル、ビニル−2,4−ジクロルフェニルエーテル、ビニルナフチルエーテル、ビニルアントラニルエーテル等)が挙げられる。 Specific examples of vinyl ethers include alkyl vinyl ethers (for example, hexyl vinyl ether, octyl vinyl ether, decyl vinyl ether, ethylhexyl vinyl ether, methoxyethyl vinyl ether, ethoxyethyl vinyl ether, chloroethyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether, 2-ethylbutyl vinyl ether, hydroxyethyl vinyl ether, diethylene glycol vinyl ether, dimethylaminoethyl vinyl ether, diethylaminoethyl vinyl ether, butylaminoethyl vinyl ether, benzyl vinyl ether, tetrahydrofurfuryl vinyl ether, etc.), vinyl aryl ethers (for example, vinyl phenyl ether, vinyl tolyl ether, Vinyl black Phenyl ether, vinyl 2,4-dichlorophenyl ether, vinyl naphthyl ether, vinyl anthranyl ether, etc.).
ビニルエステル類としては、具体的には、ビニルブチレート、ビニルイソブチレート、ビニルトリメチルアセテート、ビニルジエチルアセテート、ビニルバレート、ビニルカプロエート、ビニルクロルアセテート、ビニルジクロルアセテート、ビニルメトキシアセテート、ビニルブトキシアセテート、ビニルフエニルアセテート、ビニルアセトアセテート、ビニルラクテート、ビニル−β−フェニルブチレート、安息香酸ビニル、サリチル酸ビニル、クロル安息香酸ビニル、テトラクロル安息香酸ビニル、ナフトエ酸ビニルが挙げられる。 Specific examples of vinyl esters include vinyl butyrate, vinyl isobutyrate, vinyl trimethyl acetate, vinyl diethyl acetate, vinyl valate, vinyl caproate, vinyl chloroacetate, vinyl dichloroacetate, vinyl methoxyacetate, vinyl Examples include butoxy acetate, vinyl phenyl acetate, vinyl acetoacetate, vinyl lactate, vinyl-β-phenylbutyrate, vinyl benzoate, vinyl salicylate, vinyl chlorobenzoate, vinyl tetrachlorobenzoate, and vinyl naphthoate.
スチレン類としては、具体的には、スチレン、アルキルスチレン(例えばメチルスチレン、ジメチルスチレン、トリメチルスチレン、エチルスチレン、ジエチルスチレン、イソプロピルスチレン、ブチルスチレン、ヘキシルスチレン、シクロヘキシルスチレン、デシルスチレン、ベンジルスチレン、クロルメチルスチレン、トリフルオロメチルスチレン、エトキシメチルスチレン、アセトキシメチルスチレン等)、アルコキシスチレン(例えばメトキシスチレン、4−メトキシ−3−メチルスチレン、ジメトキシスチレン等)、ハロゲンスチレン(例えばクロルスチレン、ジクロルスチレン、トリクロルスチレン、テトラクロルスチレン、ペンタクロルスチレン、ブロムスチレン、ジブロムスチレン、ヨードスチレン、フルオロスチレン、トリフルオロスチレン、2−ブロム−4−トリフルオロメチルスチレン、4−フルオロ−3−トリフルオロメチルスチレン等)が挙げられる。また、アクリロニトリル、メタクリロニトリル等も挙げられる。 Specific examples of styrenes include styrene, alkyl styrene (for example, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, isopropyl styrene, butyl styrene, hexyl styrene, cyclohexyl styrene, decyl styrene, benzyl styrene, chloro. Methyl styrene, trifluoromethyl styrene, ethoxymethyl styrene, acetoxymethyl styrene, etc.), alkoxy styrene (eg methoxy styrene, 4-methoxy-3-methyl styrene, dimethoxy styrene, etc.), halogen styrene (eg chloro styrene, dichloro styrene, Trichlorostyrene, tetrachlorostyrene, pentachlorostyrene, bromostyrene, dibromostyrene, iodostyrene, fluorostyrene, toner Fluorostyrene, 2-bromo-4-trifluoromethyl styrene, 4-fluoro-3-trifluoromethyl styrene etc.). Also included are acrylonitrile, methacrylonitrile and the like.
上記その他の構成単位として、脂環式の基を有する単量体から誘導されるものを選択することが、層間絶縁膜の誘電率を低下させる点で好ましい。 As the other structural unit, it is preferable to select one derived from a monomer having an alicyclic group in terms of reducing the dielectric constant of the interlayer insulating film.
本発明において、共重合体(A)は、前記構成単位(A1)、(A2)及び(A3)からなることが好ましい。
上記共重合体(A)の質量平均分子量(Mw:ゲルパーミエーションクロマトグラフィ(GPC)のポリスチレン換算による測定値)は、2000〜50000であることが好ましく、5000〜30000であることがより好ましい。分子量を2000以上とすることにより、容易に膜状に形成することが可能となる。また、分子量50000以下とすることによって、適度なアルカリ溶解性を得ることが可能となる。
In the present invention, the copolymer (A) is preferably composed of the structural units (A1), (A2) and (A3).
The copolymer (A) has a mass average molecular weight (Mw: measured value by gel permeation chromatography (GPC) in terms of polystyrene) of preferably 2000 to 50000, and more preferably 5000 to 30000. When the molecular weight is 2000 or more, it can be easily formed into a film. Moreover, moderate alkali solubility can be obtained by setting the molecular weight to 50000 or less.
上記共重合体は、公知のラジカル重合により、製造することができる。即ち、前記構成単位(A1)〜(A3)等を誘導する重合性単量体、及び公知のラジカル重合開始剤を重合溶媒に溶解した後、加熱撹拌することにより製造することができる。 The copolymer can be produced by known radical polymerization. That is, it can be produced by dissolving a polymerizable monomer for inducing the structural units (A1) to (A3) and the like and a known radical polymerization initiator in a polymerization solvent, and then stirring with heating.
更に、アルカリ可溶性樹脂(A)は、上記構成単位(A1)〜(A3)を含有する共重合体以外に、1種以上の他の共重合体を含んでいてもよい。この共重合体は、上記共重合体(A)100質量部に対して、0〜50質量部であることが好ましく、0〜30質量部であることがより好ましい。この共重合体の質量平均分子量(Mw:ゲルパーミエーションクロマトグラフィ(GPC)のポリスチレン換算による測定値)は、2000〜50000であることが好ましく、5000〜30000であることがより好ましい。 Furthermore, the alkali-soluble resin (A) may contain one or more other copolymers in addition to the copolymer containing the structural units (A1) to (A3). This copolymer is preferably 0 to 50 parts by mass, and more preferably 0 to 30 parts by mass with respect to 100 parts by mass of the copolymer (A). The copolymer has a mass average molecular weight (Mw: measured value in terms of polystyrene of gel permeation chromatography (GPC)) of preferably 2000 to 50000, and more preferably 5000 to 30000.
[感光剤(B)]
本発明における感光剤(B)としては、感光成分として使用できる化合物であれば特に限定されるものではないが、好ましい例としてキノンジアジド基含有化合物が挙げられる。
[Photosensitive agent (B)]
The photosensitive agent (B) in the present invention is not particularly limited as long as it is a compound that can be used as a photosensitive component, and preferred examples include a quinonediazide group-containing compound.
キノンジアジド基含有化合物としては、具体的には、フェノール化合物(フェノール性水酸基含有化合物ともいう)と、ナフトキノンジアジドスルホン酸化合物と、の完全エステル化物や部分エステル化物が挙げられる。 Specific examples of the quinonediazide group-containing compound include completely esterified products and partially esterified products of a phenol compound (also referred to as a phenolic hydroxyl group-containing compound) and a naphthoquinonediazide sulfonic acid compound.
上記フェノール化合物としては、具体的には、2,3,4−トリヒドロキシベンゾフェノン、2,3,4,4′−テトラヒドロキシベンゾフェノン等のポリヒドロキシベンゾフェノン類;トリス(4−ヒドロシキフェニル)メタン、ビス(4−ヒドロキシ−3−メチルフェニル)−2−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,3,5−トリメチルフェニル)−2−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−3,5−ジメチルフェニル)−4−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−3,5−ジメチルフェニル)−3−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−3,5−ジメチルフェニル)−2−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)−4−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)−3−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)−2−ヒドロキシフェニルメタン、ビス(4−ヒドロキシ−3,5−ジメチルフェニル)−3,4−ジヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)−3,4−ジヒドロキシフェニルメタン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)−2,4−ジヒドロキシフェニルメタン、ビス(4−ヒドロキシフェニル)−3−メトキシ−4−ヒドロキシフェニルメタン、ビス(5−シクロヘキシル−4−ヒドロキシ−2−メチルフェニル)−4−ヒドロキシフェニルメタン、ビス(5−シクロヘキシル−4−ヒドロキシ−2−メチルフェニル)−3−ヒドロキシフェニルメタン、ビス(5−シクロヘキシル−4−ヒドロキシ−2−メチルフェニル)−2−ヒドロキシフェニルメタン、ビス(5−シクロヘキシル−4−ヒドロキシ−2−メチルフェニル)−3,4−ジヒドロキシフェニルメタン、4,4‘−[(3,4−ジヒドロキシフェニル)メチレン]ビス(2−シクロヘキシル−5−メチルフェノール)等のトリスフェノール型化合物; Specific examples of the phenol compound include 2,3,4-trihydroxybenzophenone and polyhydroxybenzophenones such as 2,3,4,4′-tetrahydroxybenzophenone; tris (4-hydroxyphenyl) methane, Bis (4-hydroxy-3-methylphenyl) -2-hydroxyphenylmethane, bis (4-hydroxy-2,3,5-trimethylphenyl) -2-hydroxyphenylmethane, bis (4-hydroxy-3,5- Dimethylphenyl) -4-hydroxyphenylmethane, bis (4-hydroxy-3,5-dimethylphenyl) -3-hydroxyphenylmethane, bis (4-hydroxy-3,5-dimethylphenyl) -2-hydroxyphenylmethane, Bis (4-hydroxy-2,5-dimethylphenyl) -4-hydride Xiphenylmethane, bis (4-hydroxy-2,5-dimethylphenyl) -3-hydroxyphenylmethane, bis (4-hydroxy-2,5-dimethylphenyl) -2-hydroxyphenylmethane, bis (4-hydroxy- 3,5-dimethylphenyl) -3,4-dihydroxyphenylmethane, bis (4-hydroxy-2,5-dimethylphenyl) -3,4-dihydroxyphenylmethane, bis (4-hydroxy-2,5-dimethylphenyl) ) -2,4-dihydroxyphenylmethane, bis (4-hydroxyphenyl) -3-methoxy-4-hydroxyphenylmethane, bis (5-cyclohexyl-4-hydroxy-2-methylphenyl) -4-hydroxyphenylmethane, Bis (5-cyclohexyl-4-hydroxy-2-methylphenol ) -3-hydroxyphenylmethane, bis (5-cyclohexyl-4-hydroxy-2-methylphenyl) -2-hydroxyphenylmethane, bis (5-cyclohexyl-4-hydroxy-2-methylphenyl) -3,4 -Trisphenol type compounds such as dihydroxyphenylmethane, 4,4 '-[(3,4-dihydroxyphenyl) methylene] bis (2-cyclohexyl-5-methylphenol);
2,4−ビス(3,5−ジメチル−4−ヒドロキシベンジル)−5−ヒドロキシフェノール、2,6−ビス(2,5−ジメチル−4−ヒドロキシベンジル)−4−メチルフェノール等のリニア型3核体フェノール化合物;1,1−ビス〔3−(2−ヒドロキシ−5−メチルベンジル)−4−ヒドロキシ−5−シクロヘキシルフェニル〕イソプロパン、ビス[2,5−ジメチル−3−(4−ヒドロキシ−5−メチルベンジル)−4−ヒドロキシフェニル]メタン、ビス[2,5−ジメチル−3−(4−ヒドロキシベンジル)−4−ヒドロキシフェニル]メタン、ビス[3−(3,5−ジメチル−4−ヒドロキシベンジル)−4−ヒドロキシ−5−メチルフェニル]メタン、ビス[3−(3,5−ジメチル−4−ヒドロキシベンジル)−4−ヒドロキシ−5−エチルフェニル]メタン、ビス[3−(3,5−ジエチル−4−ヒドロキシベンジル)−4−ヒドロキシ−5−メチルフェニル]メタン、ビス[3−(3,5−ジエチル−4−ヒドロキシベンジル)−4−ヒドロキシ−5−エチルフェニル]メタン、ビス[2−ヒドロキシ−3−(3,5−ジメチル−4−ヒドロキシベンジル)−5−メチルフェニル]メタン、ビス[2−ヒドロキシ−3−(2−ヒドロキシ−5−メチルベンジル)−5−メチルフェニル]メタン、ビス[4−ヒドロキシ−3−(2−ヒドロキシ−5−メチルベンジル)−5−メチルフェニル]メタン、ビス[2,5−ジメチル−3−(2−ヒドロキシ−5−メチルベンジル)−4−ヒドロキシフェニル]メタン等のリニア型4核体フェノール化合物;2,4−ビス[2−ヒドロキシ−3−(4−ヒドロキシベンジル)−5−メチルベンジル]−6−シクロヘキシルフェノール、2,4−ビス[4−ヒドロキシ−3−(4−ヒドロキシベンジル)−5−メチルベンジル]−6−シクロヘキシルフェノール、2,6−ビス[2,5−ジメチル−3−(2−ヒドロキシ−5−メチルベンジル)−4−ヒドロキシベンジル]−4−メチルフェノール等のリニア型5核体フェノール化合物等のリニア型ポリフェノール化合物; Linear type 3 such as 2,4-bis (3,5-dimethyl-4-hydroxybenzyl) -5-hydroxyphenol, 2,6-bis (2,5-dimethyl-4-hydroxybenzyl) -4-methylphenol Nucleophilic phenol compound; 1,1-bis [3- (2-hydroxy-5-methylbenzyl) -4-hydroxy-5-cyclohexylphenyl] isopropane, bis [2,5-dimethyl-3- (4-hydroxy) -5-methylbenzyl) -4-hydroxyphenyl] methane, bis [2,5-dimethyl-3- (4-hydroxybenzyl) -4-hydroxyphenyl] methane, bis [3- (3,5-dimethyl-4) -Hydroxybenzyl) -4-hydroxy-5-methylphenyl] methane, bis [3- (3,5-dimethyl-4-hydroxybenzyl) -4-hydride Xyl-5-ethylphenyl] methane, bis [3- (3,5-diethyl-4-hydroxybenzyl) -4-hydroxy-5-methylphenyl] methane, bis [3- (3,5-diethyl-4-) Hydroxybenzyl) -4-hydroxy-5-ethylphenyl] methane, bis [2-hydroxy-3- (3,5-dimethyl-4-hydroxybenzyl) -5-methylphenyl] methane, bis [2-hydroxy-3 -(2-hydroxy-5-methylbenzyl) -5-methylphenyl] methane, bis [4-hydroxy-3- (2-hydroxy-5-methylbenzyl) -5-methylphenyl] methane, bis [2,5 -Linear tetranuclear phenolic compounds such as dimethyl-3- (2-hydroxy-5-methylbenzyl) -4-hydroxyphenyl] methane; 2,4- [2-hydroxy-3- (4-hydroxybenzyl) -5-methylbenzyl] -6-cyclohexylphenol, 2,4-bis [4-hydroxy-3- (4-hydroxybenzyl) -5-methylbenzyl] Linear pentanuclear phenol compounds such as -6-cyclohexylphenol and 2,6-bis [2,5-dimethyl-3- (2-hydroxy-5-methylbenzyl) -4-hydroxybenzyl] -4-methylphenol Linear polyphenol compounds such as
ビス(2,3,−トリヒドロキシフェニル)メタン、ビス(2,4−ジヒドロキシフェニル)メタン、2,3,4−トリヒドロキシフェニル−4′−ヒドロキシフェニルメタン、2−(2,3,4−トリヒドロキシフェニル)−2−(2′,3′,4′−トリヒドロキシフェニル)プロパン、2−(2,4−ジヒドロキシフェニル)−2−(2′,4′−ジヒドロキシフェニル)プロパン、2−(4−ヒドロキシフェニル)−2−(4′−ヒドロキシフェニル)プロパン、2−(3−フルオロ−4−ヒドロキシフェニル)−2−(3′−フルオロ−4′−ヒドロキシフェニル)プロパン、2−(2,4−ジヒドロキシフェニル)−2−(4′−ヒドロキシフェニル)プロパン、2−(2,3,4−トリヒドロキシフェニル)−2−(4′−ヒドロキシフェニル)プロパン、2−(2,3,4−トリヒドロキシフェニル)−2−(4′−ヒドロキシ−3′,5′−ジメチルフェニル)プロパン等のビスフェノール型化合物;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−[1−(3−メチル−4−ヒドロキシフェニル)イソプロピル]−4−[1,1−ビス(3−メチル−4−ヒドロキシフェニル)エチル]ベンゼン、等の多核枝分かれ型化合物;1,1−ビス(4−ヒドロキシフェニル)シクロヘキサン等の縮合型フェノール化合物等が挙げられる。これらは単独又は2種以上組み合わせて用いることができる。 Bis (2,3-trihydroxyphenyl) methane, bis (2,4-dihydroxyphenyl) methane, 2,3,4-trihydroxyphenyl-4'-hydroxyphenylmethane, 2- (2,3,4- Trihydroxyphenyl) -2- (2 ', 3', 4'-trihydroxyphenyl) propane, 2- (2,4-dihydroxyphenyl) -2- (2 ', 4'-dihydroxyphenyl) propane, 2- (4-hydroxyphenyl) -2- (4'-hydroxyphenyl) propane, 2- (3-fluoro-4-hydroxyphenyl) -2- (3'-fluoro-4'-hydroxyphenyl) propane, 2- ( 2,4-dihydroxyphenyl) -2- (4'-hydroxyphenyl) propane, 2- (2,3,4-trihydroxyphenyl) -2- (4'- Bisphenol type compounds such as loxyphenyl) propane, 2- (2,3,4-trihydroxyphenyl) -2- (4'-hydroxy-3 ', 5'-dimethylphenyl) propane; 1- [1- (4 -Hydroxyphenyl) isopropyl] -4- [1,1-bis (4-hydroxyphenyl) ethyl] benzene, 1- [1- (3-methyl-4-hydroxyphenyl) isopropyl] -4- [1,1- Examples thereof include polynuclear branched compounds such as bis (3-methyl-4-hydroxyphenyl) ethyl] benzene; and condensed phenol compounds such as 1,1-bis (4-hydroxyphenyl) cyclohexane. These can be used alone or in combination of two or more.
また、上記ナフトキノンジアジドスルホン酸化合物としては、ナフトキノン−1,2−ジアジド−5−スルホン酸又はナフトキノン−1,2−ジアジド−4−スルホン酸等を挙げることができる。 Examples of the naphthoquinone diazide sulfonic acid compound include naphthoquinone-1,2-diazide-5-sulfonic acid and naphthoquinone-1,2-diazide-4-sulfonic acid.
また、他のキノンジアジド基含有化合物、例えばオルトベンゾキノンジアジド、オルトナフトキノンジアジド、オルトアントラキノンジアジド又はオルトナフトキノンジアジドスルホン酸エステル類等のこれらの核置換誘導体が挙げられる。更には、オルトキノンジアジドスルホニルクロリドと、水酸基又はアミノ基をもつ化合物(例えばフェノール、p−メトキシフェノール、ジメチルフェノール、ヒドロキノン、ビスフェノールA、ナフトール、ピロカテコール、ピロガロール、ピロガロールモノメチルエテール、ピロガロール−1,3−ジメチルエーテル、没食子酸、水酸基を一部残してエステル化又はエ−テル化された没食子酸、アニリン、p−アミノジフェニルアミン等)と、の反応生成物等も用いることができる。これらは単独又は2種以上を組み合わせて用いてもよい。 In addition, other quinonediazide group-containing compounds such as orthobenzoquinonediazide, orthonaphthoquinonediazide, orthoanthraquinonediazide, or orthonaphthoquinonediazidesulfonic acid esters can be used. Further, orthoquinonediazidesulfonyl chloride and a compound having a hydroxyl group or an amino group (for example, phenol, p-methoxyphenol, dimethylphenol, hydroquinone, bisphenol A, naphthol, pyrocatechol, pyrogallol, pyrogallol monomethyl ether, pyrogallol-1,3 -Dimethyl ether, gallic acid, gallic acid esterified or etherified with some hydroxyl groups remaining, aniline, p-aminodiphenylamine, etc.) and the like can also be used. You may use these individually or in combination of 2 or more types.
これらのキノンジアジド基含有化合物は、例えばトリスフェノール型化合物と、ナフトキノン−1,2−ジアジド−5−スルホニルクロリド又はナフトキノン−1,2−ジアジド−4−スルホニルクロリドとをジオキサン等の適当な溶剤中において、トリエタノールアミン、炭酸アルカリ、炭酸水素アルカリ等のアルカリの存在下で縮合させ、完全エステル化又は部分エステル化することにより製造することができる。 These quinonediazide group-containing compounds include, for example, a trisphenol type compound and naphthoquinone-1,2-diazide-5-sulfonyl chloride or naphthoquinone-1,2-diazide-4-sulfonyl chloride in a suitable solvent such as dioxane. It can be produced by condensation in the presence of an alkali such as triethanolamine, alkali carbonate, alkali hydrogencarbonate, etc., and complete esterification or partial esterification.
また、上記(B)成分としては、非ベンゾフェノン系のキノンジアジド基含有化合物を用いることが好ましく、多核枝分かれ型化合物を用いることが好ましい。また、このフェノール性水酸基含有化合物は、350nmの波長におけるグラム吸光係数が1以下であることが好ましい。これにより、感光性樹脂組成物において、より高い感度が得られ、層間絶縁膜としたときの透過率(透明性)を向上させることができる。更に、上記フェノール性水酸基含有化合物は、分解温度が、300℃以上であることがより好ましい。これにより、層間絶縁膜の透明性を確保することができる。 Moreover, as said (B) component, it is preferable to use a non-benzophenone series quinonediazide group containing compound, and it is preferable to use a polynuclear branched type compound. The phenolic hydroxyl group-containing compound preferably has a gram extinction coefficient of 1 or less at a wavelength of 350 nm. Thereby, in the photosensitive resin composition, higher sensitivity can be obtained, and the transmittance (transparency) when an interlayer insulating film is formed can be improved. Furthermore, the phenolic hydroxyl group-containing compound preferably has a decomposition temperature of 300 ° C. or higher. Thereby, the transparency of the interlayer insulating film can be ensured.
このような(B)成分としては、キノンジアジド基含有化合物が好ましく、特にナフトキノンジアジドスルホン酸エステル化物が好ましい。なかでも、4,4‘−[(3,4−ジヒドロキシフェニル)メチレン]ビス(2−シクロヘキシル−5−メチルフェノール)、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]ベンゼン等のナフトキノンジアジドスルホン酸エステル化物を好適に用いることができる。 As such component (B), a quinonediazide group-containing compound is preferable, and a naphthoquinonediazidesulfonic acid ester is particularly preferable. Among them, 4,4 ′-[(3,4-dihydroxyphenyl) methylene] bis (2-cyclohexyl-5-methylphenol), 1- [1- (4-hydroxyphenyl) isopropyl] -4- [1, A naphthoquinonediazide sulfonate esterified product such as 1-bis (4-hydroxyphenyl) ethyl] benzene can be suitably used.
(B)成分の含有量は、全固形成分に対し、10〜40質量%が好ましく、更に好ましくは15〜30質量%である。(B)成分の含有量を10質量%以上とすることによって、解像度を向上させることが可能となる。また、パターンを形成した後の、パターンの膜減り量を低減させることが可能となる。また、(B)成分の含有量を40質量%以下とすることによって、適度な感度や透過率を付与することが可能となる。 (B) As for content of a component, 10-40 mass% is preferable with respect to all the solid components, More preferably, it is 15-30 mass%. By setting the content of the component (B) to 10% by mass or more, the resolution can be improved. Further, it is possible to reduce the amount of pattern loss after the pattern is formed. Further, by setting the content of the component (B) to 40% by mass or less, it is possible to impart appropriate sensitivity and transmittance.
[シランカップリング剤(C)]
本発明の層間絶縁膜形成用感光性樹脂組成物は、シランカップリング剤(C)を含有する。本発明の層間絶縁膜形成用感光性樹脂組成物は、シランカップリング剤(C)を含有することにより、本発明の感光性樹脂組成物により形成された膜と基板との密着性を向上できたり、本発明の感光性樹脂組成物により形成された膜の性質を調整することができる。
シランカップリング剤(C)として、具体的には、例えば、γ−アミノプロピルトリメトキシシラン、γ−アミノプロピルトリエトキシシラン、γ−グリシドキシプロピルトリアコキシシラン、γ−グリシドキシプロピルアルキルジアルコキシシラン、γ−メタクリロキシプロピルトリアルコキシシラン、γ−メタクリロキシプロピルアルキルジアルコキシシラン、γ−クロロプロピルトリアルコキシシラン、γ−メルカプトプロピルトリアルコキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリアルコキシシラン、ビニルトリアルコキシシランが挙げられる。これらのうち、γ−グリシドキシプロピルトリアルコキシシランやγ−メタクリロキシプロピルトリアルコキシシランがより好ましく、γ−グリシドキシプロピルトリアルコキシシランがさらに好ましく、3−グリシドキシプロピルトリメトキシシランがよりさらに好ましい。これらは1種単独または2種以上を組み合わせて使用することができる。
[Silane coupling agent (C)]
The photosensitive resin composition for forming an interlayer insulating film of the present invention contains a silane coupling agent (C). By containing the silane coupling agent (C), the photosensitive resin composition for forming an interlayer insulating film of the present invention can improve the adhesion between the film formed by the photosensitive resin composition of the present invention and the substrate. The properties of the film formed from the photosensitive resin composition of the present invention can be adjusted.
Specific examples of the silane coupling agent (C) include γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxypropyltriacoxysilane, and γ-glycidoxypropylalkyl. Dialkoxysilane, γ-methacryloxypropyltrialkoxysilane, γ-methacryloxypropylalkyldialkoxysilane, γ-chloropropyltrialkoxysilane, γ-mercaptopropyltrialkoxysilane, β- (3,4-epoxycyclohexyl) ethyl Examples include trialkoxysilane and vinyltrialkoxysilane. Of these, γ-glycidoxypropyltrialkoxysilane and γ-methacryloxypropyltrialkoxysilane are more preferable, γ-glycidoxypropyltrialkoxysilane is more preferable, and 3-glycidoxypropyltrimethoxysilane is more preferable. Further preferred. These can be used alone or in combination of two or more.
前記シランカップリング剤を含有する場合、その含有量は本発明の感光性樹脂組成物の全固形分に対して好ましくは0.01〜10質量%、より好ましくは0.1〜2質量%、最も好ましくは0.2〜1.5質量%である。前記のような範囲で含まれる場合、本発明の感光性樹脂組成物から形成されるパターンと基板との密着性が向上して好ましい。 When the silane coupling agent is contained, the content thereof is preferably 0.01 to 10% by mass, more preferably 0.1 to 2% by mass, based on the total solid content of the photosensitive resin composition of the present invention. Most preferably, it is 0.2-1.5 mass%. When included in the above range, the adhesiveness between the pattern formed from the photosensitive resin composition of the present invention and the substrate is preferably improved.
[架橋剤(D)]
本発明の層間絶縁膜形成用感光性樹脂組成物は、架橋剤(D)を含有する。架橋剤(D)は、オキセタン含有化合物、エポキシ基含有化合物及びブロックイソシアネート化合物からなる群から選択される少なくとも1種である。
本発明の層間絶縁膜形成用感光性樹脂組成物は、架橋剤(D)を含有することにより、架橋密度が向上するため、本発明の層間絶縁膜形成用感光性樹脂組成物を用いて形成した層間絶縁膜の弾性が向上し破断伸度をより高くでき、機械特性に優れたものとすることができると考えられる。その結果、本発明の層間絶縁膜形成用感光性樹脂組成物を用いて形成した層間絶縁膜の機械特性は、ポリイミド樹脂を採用した場合と同等又はそれ以上とすることができると考えられる。
[Crosslinking agent (D)]
The photosensitive resin composition for forming an interlayer insulating film of the present invention contains a crosslinking agent (D). The crosslinking agent (D) is at least one selected from the group consisting of an oxetane-containing compound, an epoxy group-containing compound, and a blocked isocyanate compound.
The photosensitive resin composition for forming an interlayer insulating film of the present invention is formed using the photosensitive resin composition for forming an interlayer insulating film of the present invention because the crosslinking density is improved by containing the crosslinking agent (D). It is considered that the elasticity of the interlayer insulating film is improved, the elongation at break can be further increased, and the mechanical properties can be improved. As a result, it is considered that the mechanical properties of the interlayer insulating film formed using the photosensitive resin composition for forming an interlayer insulating film of the present invention can be equal to or higher than that when a polyimide resin is employed.
〔オキセタン含有化合物、エポキシ基含有化合物〕
オキセタン基又はエポキシ基を有する化合物としては、例えば、スチレンオキシド、フェニルグリシジルエーテル、o−フェニルフェノールグリシジルエーテル、p−フェニルフェノールグリシジルエーテル、グリシジルシンナメート、メチルグリシジルエーテル、ブチルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、デシルグリシジルエーテル、ステアリルグリシジルエーテル、アリルグリシジルエーテル、グリシドール、N−グリシジルフタルイミド、1,3−ジブロモフェニルグリシジルエーテル、セロキサイド2000(ダイセル化学工業株式会社製)、オキセタンアルコール等が挙げられる。
オキセタン含有化合物の具体例としては、アロンオキセタンOXT−121、OXT−221、OX−SQ、PNOX(以上、東亞合成(株)製)を用いることができる。
エポキシ基含有化合物の具体例としては、エポキシ樹脂EXA4850−150、エポキシ樹脂EXA4850−1000(ともにDIC株式会社製)を用いることができる。
[Oxetane-containing compound, epoxy group-containing compound]
Examples of the compound having an oxetane group or an epoxy group include styrene oxide, phenyl glycidyl ether, o-phenylphenol glycidyl ether, p-phenylphenol glycidyl ether, glycidyl cinnamate, methyl glycidyl ether, butyl glycidyl ether, and 2-ethylhexyl glycidyl. Examples include ether, decyl glycidyl ether, stearyl glycidyl ether, allyl glycidyl ether, glycidol, N-glycidyl phthalimide, 1,3-dibromophenyl glycidyl ether, Celoxide 2000 (manufactured by Daicel Chemical Industries, Ltd.), and oxetane alcohol.
As specific examples of the oxetane-containing compound, Aron oxetane OXT-121, OXT-221, OX-SQ, and PNOX (manufactured by Toagosei Co., Ltd.) can be used.
As specific examples of the epoxy group-containing compound, epoxy resin EXA4850-150 and epoxy resin EXA4850-1000 (both manufactured by DIC Corporation) can be used.
〔ブロックイソシアネート化合物〕
本発明において使用されるブロックイソシアネート化合物は、本願発明に用いられるブロックイソシアネートは、常温では不活性であり、加熱されることにより、オキシム類、ジケトン類、フェノール類、カプロラクタム類等のブロック剤が解離してイソシアネート基を再生する化合物である。ブロックイソシアネート化合物は1種を単独で使用できまたは2種以上を併用できる。
ここで、イソシアネート化合物としては公知のものを使用でき、たとえば、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、リジンジイソシアネートなどの脂肪族ジイソシアネート、ジシクロへキシルメタンジイソシアネート、イソホロンジイソシアネート、1、4−シクロヘキサンジイソシアネート、水添キシリレンジイソシアネート、水添トリレンジイソシアネートなどの脂環式ジイソシアネート、トリレンジイソシアネート、4,4’−ジフェニルメタンジイソシアネート、2,4’−ジフェニルメタンジイソシアネート、ナフタレンジイソシアネート、キシリレンジイソシアネート、トリジンジイソシアネート、p−フェニレンジイソシアネート、ナフチレンジイソシアネートなどの芳香族ジイソシアネート、ジシクロへキシルメタン−4,4’−ジイソシアネート、これらのビウレット体、イソシアヌレート体、トリメチロールプロパンのアダクト体などが挙げられる。これらの中でも、ヘキサメチレンジイソシアネート、リジンジイソシアネートなどの脂肪族ジイソシアネート、ジシクロへキシルジイソシアネート、イソホロンジイソシアネートなどの脂環式ジイソシアネート、トリレンジイソシアネート、トリジンジイソシアネート、キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、ナフチレンジイソシアネートなどの芳香族ジイソシアネート、これらのビウレット体、イソシアヌレート体、トリメチロールプロパンのアダクト体などが好ましい。
中でもアダクト体としては、脂肪族ジイソシアネートとトリメチロールプロパンとの付加体が、ビウレット体としてはヘキサメチレンジイソシアネートと水又は三級アルコールとの反応物が、イソシアヌレート体としてはヘキサメチレンジイソシアネートの三量体が好ましい。
[Block isocyanate compounds]
The blocked isocyanate compound used in the present invention, the blocked isocyanate used in the present invention is inactive at room temperature, and when heated, the blocking agents such as oximes, diketones, phenols, caprolactams dissociate Thus, the compound regenerates the isocyanate group. A block isocyanate compound can be used individually by 1 type, or can use 2 or more types together.
Here, known isocyanate compounds can be used, for example, aliphatic diisocyanates such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, dicyclohexylmethane diisocyanate, isophorone diisocyanate, 1,4-cyclohexane diisocyanate, water. Alicyclic diisocyanates such as hydrogenated xylylene diisocyanate and hydrogenated tolylene diisocyanate, tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, naphthalene diisocyanate, xylylene diisocyanate, tolidine diisocyanate, p-phenylene Aromatic diisocyanates such as diisocyanate and naphthylene diisocyanate Over DOO, Kishirumetan 4,4'-diisocyanate dicyclohexyl, these biuret, isocyanurate, and the like adducts of trimethylol propane. Among these, aliphatic diisocyanates such as hexamethylene diisocyanate and lysine diisocyanate, alicyclic diisocyanates such as dicyclohexyl diisocyanate and isophorone diisocyanate, aromas such as tolylene diisocyanate, tolidine diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate and naphthylene diisocyanate Preferred are group diisocyanates, biurets, isocyanurates, and adducts of trimethylolpropane.
Among them, an adduct is an adduct of aliphatic diisocyanate and trimethylolpropane, a biuret is a reaction product of hexamethylene diisocyanate and water or a tertiary alcohol, and an isocyanurate is a trimer of hexamethylene diisocyanate. Is preferred.
ブロック剤は、ポリイソシアネート基に付加し、常温では安定であるが解離温度以上に加熱すると遊離してイソシアネート基を生成する化合物である。ブロック化剤の具体例としては、たとえば、γ−ブチロラクタム、ε−カプロラクタム、γ−バレロラクタム、プロピオラクタムなどのラクタム化合物、メチルエチルケトオキシム、メチルイソアミルケトオキシム、メチルイソブチルケトオキシム、ホルムアミドオキシム、アセトアミドオキシム、アセトオキシム、ジアセチルモノオキシム、ベンゾフェノンオキシム、シクロヘキサノンオキシムなどのオキシム化合物、フェノール、クレゾール、カテコール、ニトロフェノールなどの単環フェノール化合物、1−ナフトールなどの多環フェノール化合物、メチルアルコール、エチルアルコール、イソプロピルアルコール、tert−ブチルアルコール、トリメチロールプロパン、2−エチルヘキシルアルコールなどのアルコール化合物、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテルなどのエーテル化合物、マロン酸アルキルエステル、マロン酸ジアルキルエステル、アセト酢酸アルキルエステル、アセチルアセトンなどの活性メチレン化合物などが挙げられる。ブロック剤は1種を単独で使用できまたは2種以上併用できる。 A blocking agent is a compound that is added to a polyisocyanate group and is stable at room temperature but is liberated to generate an isocyanate group when heated to a temperature higher than the dissociation temperature. Specific examples of the blocking agent include, for example, lactam compounds such as γ-butyrolactam, ε-caprolactam, γ-valerolactam, propiolactam, methyl ethyl ketoxime, methyl isoamyl ketoxime, methyl isobutyl ketoxime, formamide oxime, acetamide oxime Oxime compounds such as acetooxime, diacetyl monooxime, benzophenone oxime, cyclohexanone oxime, monocyclic phenol compounds such as phenol, cresol, catechol, nitrophenol, polycyclic phenol compounds such as 1-naphthol, methyl alcohol, ethyl alcohol, isopropyl Alcohol compounds such as alcohol, tert-butyl alcohol, trimethylolpropane, 2-ethylhexyl alcohol, Glycol monomethyl ether, ethylene glycol monoethyl ether, ether compounds such as ethylene glycol monobutyl ether, malonic acid alkyl esters, malonic acid dialkyl esters, acetoacetic acid alkyl esters, and the like active methylene compounds such as acetylacetone. A blocking agent can be used individually by 1 type, or can be used together 2 or more types.
ブロックイソシアネート化合物は、イソシアネート化合物とブロック剤とを反応させることによって製造できる。イソシアネート化合物とブロック剤との反応は、たとえば、活性水素を持たない溶剤(1.4ジオキサン、セロソルブアセテート等)中にて50〜100℃程度の加熱下および必要に応じてブロック化触媒の存在下に行われる。イソシアネート化合物とブロック化剤との使用割合は特に制限されないが、好ましくは、イソシアネート化合物中のイソシアネート基とブロック剤との当量比として、0.95:1.0〜1.1:1.0であり、さらに好ましくは1:1.05〜1.15である。ブロック化触媒としては公知のものを使用でき、たとえば、ナトリウムメチラート、ナトリウムエチラート、ナトリウムフェノラート、カリウムメチラートなどの金属アルコラート、テトラメチルアンモニウム、テトラエチルアンモニウム、テトラブチルアンモニウムなどのテトラアルキルアンモニウムのハイドロオキサイド、これらの酢酸塩、オクチル酸塩、ミリスチン酸塩、安息香酸塩などの有機弱酸塩、酢酸、カプロン酸、オクチル酸、ミリスチン酸などのアルキルカルボン酸のアルカリ金属塩などが挙げられる。ブロック化触媒は1種を単独で使用できまたは2種以上を併用できる。 A blocked isocyanate compound can be produced by reacting an isocyanate compound with a blocking agent. The reaction between the isocyanate compound and the blocking agent is carried out, for example, in a solvent having no active hydrogen (1.4 dioxane, cellosolve acetate, etc.) under heating at about 50 to 100 ° C. and, if necessary, in the presence of a blocking catalyst. To be done. The use ratio of the isocyanate compound and the blocking agent is not particularly limited, but is preferably 0.95: 1.0 to 1.1: 1.0 as an equivalent ratio of the isocyanate group to the blocking agent in the isocyanate compound. Yes, more preferably 1: 1.05 to 1.15. Known blocking catalysts can be used, for example, metal alcoholates such as sodium methylate, sodium ethylate, sodium phenolate and potassium methylate, and tetraalkylammonium such as tetramethylammonium, tetraethylammonium and tetrabutylammonium. Examples thereof include hydroxides, organic weak acid salts such as acetates thereof, octylates, myristates and benzoates, and alkali metal salts of alkylcarboxylic acids such as acetic acid, caproic acid, octylic acid and myristic acid. The blocked catalyst can be used alone or in combination of two or more.
ブロックイソシアネート化合物としては市販品をも使用できる。市販品の具体例としては、TPA−B80E(商品名、旭化成株式会社製、イソシアヌート型)、17B−60P(商品名、旭化成株式会社製、ビウレット型)、E402−B80B(商品名、旭化成株式会社製、アダクト型)などが挙げられる。
ブロックイソシアネート化合物の含有量は本発明の感光性樹脂組成物の全固形分に対して好ましくは1〜60質量%、より好ましくは5〜50質量%、最も好ましくは10〜40質量%である。
A commercial item can also be used as a block isocyanate compound. Specific examples of commercially available products include TPA-B80E (trade name, manufactured by Asahi Kasei Corporation, isocyanut type), 17B-60P (trade name, manufactured by Asahi Kasei Corporation, biuret type), E402-B80B (trade name, Asahi Kasei Corporation) Company-made, adduct type).
The content of the blocked isocyanate compound is preferably 1 to 60% by mass, more preferably 5 to 50% by mass, and most preferably 10 to 40% by mass with respect to the total solid content of the photosensitive resin composition of the present invention.
本発明において、架橋剤(D)としては、層間絶縁膜の機械特性を向上させる観点から、ブロックイソシアネート化合物を採用することが好ましい。
また、ブロックイソシアネート化合物の中でも、アダクト型のブロックイソシアネート化合物を採用することが好ましい。
アダクト型のブロックイソシアネート化合物を採用する場合は、アダクト型のブロックイソシアネート化合物の含有量は本発明の感光性樹脂組成物の全固形分に対して好ましくは10〜40質量%、より好ましくは15〜25質量%である。
上記範囲とすることにより、層間絶縁膜の機械特性の向上に加え、熱耐性も付与することができる。
In the present invention, as the crosslinking agent (D), a blocked isocyanate compound is preferably employed from the viewpoint of improving the mechanical properties of the interlayer insulating film.
Of the blocked isocyanate compounds, an adduct type blocked isocyanate compound is preferably employed.
When an adduct type blocked isocyanate compound is employed, the content of the adduct type blocked isocyanate compound is preferably 10 to 40% by mass, more preferably 15 to 15%, based on the total solid content of the photosensitive resin composition of the present invention. 25% by mass.
By setting it as the said range, in addition to the improvement of the mechanical characteristic of an interlayer insulation film, heat resistance can also be provided.
[有機溶剤(S)]
本発明に係る感光性樹脂組成物は、塗布性を改善したり、粘度を調整したりするために、有機溶剤(S)を含有することが好ましい。
[Organic solvent (S)]
The photosensitive resin composition according to the present invention preferably contains an organic solvent (S) in order to improve applicability or adjust the viscosity.
(S)成分としては、ベンゼン、トルエン、キシレン、メチルエチルケトン、アセトン、メチルイソブチルケトン、シクロヘキサノン、メタノール、エタノール、プロパノール、ブタノール、ヘキサノール、シクロヘキサノール、エチレングリコール、ジエチレングリコール、グリセリン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル(PGME)、プロピレングリコールモノエチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、3−メトキシブチルアセテート(MA)、3−メトキシブタノール(BM)、3−メチル−3−メトキシブチルアセテート、プロピレングリコールモノメチルエーテアセテート(PGMEA)、プロピレングリコールモノメチルエーテルプロピオネート、プロピレングリコールモノエチルエーテルプロピオネート、炭酸メチル、炭酸エチル、炭酸プロピル、炭酸ブチル又はこれらの混合物等が挙げられる。中でもPGME、PGMEA、MAや、PGMEとPGMEAの混合溶剤、MAとBMの混合溶剤等を用いることが好ましい。 As component (S), benzene, toluene, xylene, methyl ethyl ketone, acetone, methyl isobutyl ketone, cyclohexanone, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, glycerin, ethylene glycol monomethyl ether, ethylene glycol Monoethyl ether, propylene glycol monomethyl ether (PGME), propylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, 3-methoxybutyl acetate (MA), 3-methoxybutanol (BM) , 3-methyl- -Methoxybutyl acetate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether propionate, methyl carbonate, ethyl carbonate, propyl carbonate, butyl carbonate or a mixture thereof . Among these, it is preferable to use PGMEA, PGMEA, MA, a mixed solvent of PGME and PGMEA, a mixed solvent of MA and BM, and the like.
有機溶剤(S)の使用量は特に限定されないが、基板等に塗布可能な濃度で、塗布膜厚に応じて適宜設定される。具体的には、感光性樹脂組成物の固形分濃度が10〜50質量%、特に15〜35質量%の範囲内となるように用いることが好ましい。 The amount of the organic solvent (S) used is not particularly limited, and is a concentration that can be applied to a substrate or the like, and is appropriately set according to the coating film thickness. Specifically, it is preferable to use the photosensitive resin composition so that the solid content concentration is in the range of 10 to 50% by mass, particularly 15 to 35% by mass.
[界面活性剤(E)]
本発明の層間絶縁膜形成用感光性樹脂組成物は、界面活性剤(E)を含有していてもよい。
界面活性剤(E)としては、シリコーン系界面活性剤またはフッ素系界面活性剤が挙げられる。具体的には、シリコーン系界面活性剤は、BYK−Chemie社のBYK−077、BYK−085、BYK−300、BYK−301、BYK−302、BYK−306、BYK−307、BYK−310、BYK−320、BYK−322、BYK−323、BYK−325、BYK−330、BYK−331、BYK−333、BYK−335、BYK−341v344、BYK−345v346、BYK−348、BYK−354、BYK−355、BYK−356、BYK−358、BYK−361、BYK−370、BYK−371、BYK−375、BYK−380、BYK−390などを使用することができる。
フッ素系界面活性剤としては、DIC(DaiNippon Ink&Chemicals)社のF−114、F−177、F−410、F−411、F−450、F−493、F−494、F−443、F−444、F−445、F−446、F−470、F−471、F−472SF、F−474、F−475、F−477、F−478、F−479、F−480SF、F−482、F−483、F−484、F−486、F−487、F−172D、MCF−350SF、TF−1025SF、TF−1117SF、TF−1026SF、TF−1128、TF−1127、TF−1129、TF−1126、TF−1130、TF−1116SF、TF−1131、TF1132、TF1027SF、TF−1441、TF−1442などを使用することができるが、これらにのみ限定されるものではない。
[Surfactant (E)]
The photosensitive resin composition for forming an interlayer insulating film of the present invention may contain a surfactant (E).
Examples of the surfactant (E) include silicone surfactants and fluorine surfactants. Specifically, BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK are available. -320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355 BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, and the like can be used.
Fluorosurfactants include DIC (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, and F-444. F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F -483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126 , TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442 However, it is not limited only to these.
前記界面活性剤を含有する場合、その含有量は本発明の感光性樹脂組成物の全固形分に対して好ましくは0.01〜10質量%、より好ましくは0.1〜2質量%、最も好ましくは0.05〜1.0質量%である。前記のような範囲で含まれる場合、本発明の感光性樹脂組成物から形成されるパターンと基板との密着性が向上して好ましい。 When the surfactant is contained, the content thereof is preferably 0.01 to 10% by mass, more preferably 0.1 to 2% by mass, most preferably based on the total solid content of the photosensitive resin composition of the present invention. Preferably it is 0.05-1.0 mass%. When included in the above range, the adhesiveness between the pattern formed from the photosensitive resin composition of the present invention and the substrate is preferably improved.
[その他]
また、本発明に係る感光性樹脂組成物は、界面活性剤や、増感剤、消泡剤等の各種添加剤を含有していてもよい。
[Others]
Moreover, the photosensitive resin composition which concerns on this invention may contain various additives, such as surfactant, a sensitizer, and an antifoamer.
界面活性剤としては、従来公知のものであってよく、アニオン系、カチオン系、ノニオン系等の化合物が挙げられる。具体的には、X−70−090(商品名、信越化学工業社製)等を挙げることができる。界面活性剤を添加することにより、塗布性、平坦性を向上させることができる。 The surfactant may be a conventionally known surfactant, and examples thereof include anionic, cationic, and nonionic compounds. Specific examples include X-70-090 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.). By adding the surfactant, the coating property and flatness can be improved.
増感剤としては、従来公知のポジ型レジストに用いられるものを使用することができる。例えば、分子量1000以下のフェノール性水酸基を有する化合物等が挙げられる。 As the sensitizer, those used in conventionally known positive resists can be used. For example, a compound having a phenolic hydroxyl group having a molecular weight of 1000 or less can be used.
上記消泡剤としては、従来公知のものであってよく、シリコーン系化合物、フッ素系化合物が挙げられる。 As said antifoamer, a conventionally well-known thing may be used and a silicone type compound and a fluorine-type compound are mentioned.
本発明に係る感光性樹脂組成物は、例えば、(A)成分、(B)成分、(C)成分及び(D)成分を、ロールミル、ボールミル、サンドミル等の撹拌機で混合(分散及び混練)し、必要に応じて5μmメンブランフィルター等のフィルターで濾過して調製することができる。 In the photosensitive resin composition according to the present invention, for example, the component (A), the component (B), the component (C), and the component (D) are mixed (dispersed and kneaded) with a stirrer such as a roll mill, a ball mill, or a sand mill. And it can prepare by filtering with filters, such as a 5 micrometer membrane filter, as needed.
[層間絶縁膜]
本発明は、前記層間絶縁膜形成用感光性樹脂組成物を用いた層間絶縁膜を提供する。
本発明の層間絶縁膜は、液晶表示素子、集積回路素子、固体撮像素子等の電子部品における層状に配置される配線の間を絶縁するために設ける層間絶縁膜として好適に用いることができる。
[Interlayer insulation film]
The present invention provides an interlayer insulating film using the photosensitive resin composition for forming an interlayer insulating film.
The interlayer insulating film of the present invention can be suitably used as an interlayer insulating film provided for insulating between wirings arranged in layers in electronic components such as liquid crystal display elements, integrated circuit elements, and solid-state imaging elements.
以下、本発明に係る感光性樹脂組成物を用いて層間絶縁膜を形成する方法について説明
する。
Hereinafter, a method for forming an interlayer insulating film using the photosensitive resin composition according to the present invention will be described.
[層間絶縁膜の形成方法]
まず、基板等の支持体上に本発明に係る感光性樹脂組成物をスピンナー、ロールコーター、スプレーコーター、スリットコーター等を用いて塗布、乾燥させ、感光性樹脂組成物層を形成する。上記基板としては、例えば、透明導電回路等の配線を備え、必要に応じてブラックマトリクス、カラーフィルタ、偏光板等を備えるガラス板が挙げられる。
[Method for forming interlayer insulating film]
First, the photosensitive resin composition according to the present invention is applied on a support such as a substrate using a spinner, a roll coater, a spray coater, a slit coater, or the like, and dried to form a photosensitive resin composition layer. Examples of the substrate include a glass plate that includes wiring such as a transparent conductive circuit, and includes a black matrix, a color filter, a polarizing plate, and the like as necessary.
上記乾燥の方法としては、例えば(1)ホットプレートにて80〜120℃の温度にて60〜120秒間乾燥する方法、(2)室温にて数時間〜数日放置する方法、(3)温風ヒータや赤外線ヒータ中に数十分〜数時間入れて溶剤を除去する方法、のいずれでもよい。また、上記感光性樹脂組成物層の膜厚は、特に限定されるものではないが、1.0〜5.0μm程度であることが好ましい。 Examples of the drying method include (1) a method of drying on a hot plate at a temperature of 80 to 120 ° C. for 60 to 120 seconds, (2) a method of leaving at room temperature for several hours to several days, and (3) a temperature. Any of a method of removing the solvent by putting it in a wind heater or an infrared heater for several tens of minutes to several hours may be used. Moreover, the film thickness of the said photosensitive resin composition layer is although it does not specifically limit, It is preferable that it is about 1.0-5.0 micrometers.
次いで、所定のマスクを介して、露光を行う。この露光は、紫外線、エキシマレーザ光等の活性エネルギー線を照射することにより行う。この活性エネルギー線の光源としては、例えば低圧水銀灯、高圧水銀灯、超高圧水銀灯、ケミカルランプ、エキシマレーザー発生装置等が挙げられる。照射するエネルギー線量は、感光性樹脂組成物の組成によっても異なるが、例えば30〜2000mJ/cm2程度であればよい。 Next, exposure is performed through a predetermined mask. This exposure is performed by irradiating active energy rays such as ultraviolet rays and excimer laser light. Examples of the active energy ray light source include a low-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a chemical lamp, and an excimer laser generator. Although the energy dose to be irradiated varies depending on the composition of the photosensitive resin composition, it may be, for example, about 30 to 2000 mJ / cm 2 .
次いで、露光された感光性樹脂組成物層を、現像液で現像し、パターンを形成する。この現像液としては、テトラメチルアンモニウムヒドロキシド(TMAH)水溶液のような有機アルカリ水溶液又は水酸化ナトリウム、水酸化カリウム、メタケイ酸ナトリウム、リン酸ナトリウム等の無機アルカリ水溶液が挙げられる。これにより、所望の範囲に層間絶縁膜を設けることができる。最後に、前記パターンを加熱硬化する。この加熱硬化温度しては、例えば300℃以下の条件で加熱硬化処理を行うことが好ましく、250℃以下の条件で加熱硬化処理を行うことがより好ましい。 Next, the exposed photosensitive resin composition layer is developed with a developer to form a pattern. Examples of the developer include an organic alkaline aqueous solution such as a tetramethylammonium hydroxide (TMAH) aqueous solution or an inorganic alkaline aqueous solution such as sodium hydroxide, potassium hydroxide, sodium metasilicate, and sodium phosphate. Thereby, an interlayer insulating film can be provided in a desired range. Finally, the pattern is cured by heating. For example, the heat curing temperature is preferably 300 ° C. or lower, and more preferably 250 ° C. or lower.
以下、実施例により本発明をより具体的に説明するが、本発明は以下の実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to a following example.
≪感光性樹脂組成物の調製≫
表1〜2に示す各成分を混合してPGMEA/PGME=60/40の混合溶剤に溶解し、感光性樹脂組成物を調製した。なお、実施例1〜11及び比較例1の固形分濃度は20質量%、実施例12〜22及び比較例2の固形分濃度は40質量%である。
<< Preparation of photosensitive resin composition >>
The components shown in Tables 1 and 2 were mixed and dissolved in a mixed solvent of PGMEA / PGME = 60/40 to prepare a photosensitive resin composition. In addition, solid content concentration of Examples 1-11 and Comparative Example 1 is 20 mass%, and solid content concentration of Examples 12-22 and Comparative Example 2 is 40 mass%.
上記表中の各略号は以下の意味を有する。また、[ ]内の数値は配合量(質量部)である。
(A)−1:下記高分子化合物(A)−1
(A)−2:下記高分子化合物(A)−2
(B)−1:下記化合物(B)−1に対し、ナフトキノンジアジド−5−スルホン酸エステルを3モル反応させたもの
(B)−2:下記化合物(B)−1に対し、ナフトキノンジアジド−5−スルホン酸エステルを2モル反応させたもの
(C)−1:下記化合物(C)−1
(D)−1:オキセタン架橋剤(東亜合成社製、OXT−121)
(D)−2:柔軟エポキシ架橋剤
(大日本インキ化学工業社製、EXA4850−150)
(D)−3:ブロックイソシアヌート架橋剤イソシアヌート型
(旭化成ケミカルズ社製、TPA−B80E)
(D)−4:ブロックイソシアヌート架橋剤ビウレット型
(旭化成ケミカルズ社製、17B−60P)
(D)−5:ブロックイソシアヌート架橋剤アダクト型
(旭化成ケミカルズ社製、E402−B80B)
(E)−1:シリコン系表面調整剤(ビックケミー・ジャパン社製、BYK−310)
Each abbreviation in the above table has the following meaning. Moreover, the numerical value in [] is a compounding quantity (mass part).
(A) -1: the following polymer compound (A) -1
(A) -2: the following polymer compound (A) -2
(B) -1: 3 mol of naphthoquinonediazide-5-sulfonic acid ester reacted with the following compound (B) -1 (B) -2: naphthoquinonediazide with respect to the following compound (B) -1 A product obtained by reacting 2 mol of 5-sulfonic acid ester (C) -1: the following compound (C) -1
(D) -1: Oxetane crosslinking agent (manufactured by Toa Gosei Co., Ltd., OXT-121)
(D) -2: Flexible epoxy crosslinking agent (Dainippon Ink & Chemicals, EXA 4850-150)
(D) -3: Block isocyanut cross-linking agent isocyanut type (manufactured by Asahi Kasei Chemicals Corporation, TPA-B80E)
(D) -4: Block isocyanurate crosslinker biuret type (Asahi Kasei Chemicals, 17B-60P)
(D) -5: Block isocyanate block adduct type (E402-B80B manufactured by Asahi Kasei Chemicals Corporation)
(E) -1: Silicon-based surface conditioner (BYK-310, manufactured by BYK Japan)
<感光性樹脂膜の形成>
実施例および比較例で調製した感光性樹脂組成物を、8インチシリコン基板上にスピンコーター(TR25000:東京応化(株)製)を用いて塗布し、115℃で90秒間プリベークを行い、膜厚2.0μmの塗膜を形成した。次いで、i線ステッパー(製品名:NSR−i 14E、株式会社ニコン製、NA=0.50、σ=0.64、Focus=0μm)を使用し、塗膜に紫外線を照射した。露光量は、500mJ/cm2とした。
露光後の塗膜を、23℃にて2.38質量%テトラメチルアンモニウムヒドロキシド水溶液で60秒間現像し、100℃で30分間、その後120℃で30分間、その後200℃で60分間の熱硬化処理を行った。
そして、作製された各感光性樹脂膜について、下記の評価を行った。その結果を表3〜4に示す。
<Formation of photosensitive resin film>
The photosensitive resin compositions prepared in Examples and Comparative Examples were applied on an 8-inch silicon substrate using a spin coater (TR25000: manufactured by Tokyo Ohka Kogyo Co., Ltd.), pre-baked at 115 ° C. for 90 seconds, and film thickness A 2.0 μm coating film was formed. Next, an i-line stepper (product name: NSR-i 14E, manufactured by Nikon Corporation, NA = 0.50, σ = 0.64, Focus = 0 μm) was used to irradiate the coating film with ultraviolet rays. The exposure amount was 500 mJ / cm 2 .
The exposed coating film is developed with an aqueous 2.38 mass% tetramethylammonium hydroxide solution at 23 ° C. for 60 seconds, and then thermally cured at 100 ° C. for 30 minutes, then at 120 ° C. for 30 minutes, and then at 200 ° C. for 60 minutes. Processed.
And the following evaluation was performed about each produced photosensitive resin film. The results are shown in Tables 3-4.
[引張伸度、引張強度、引張弾性率]
得られた感光性樹脂膜を万能材料試験機(TENSILON、株式会社オリエンテック製)によって、感光性樹脂の破断伸度、破断強度、及び引張弾性率を測定した。引張伸度の評価結果を「Elongation (%)」、破断強度の評価結果を「Tensile strength (%)」、引張弾性率の評価結果を「Young modulus (Gpa)」として表3〜4に記す。
[Tensile elongation, tensile strength, tensile modulus]
The obtained photosensitive resin film was measured for the elongation at break, the breaking strength, and the tensile modulus of the photosensitive resin with a universal material testing machine (TENSILON, manufactured by Orientec Co., Ltd.). Tables 3 to 4 show the evaluation results of tensile elongation as “Elongation (%)”, the evaluation results of breaking strength as “Tensile strength (%)”, and the evaluation results of tensile modulus as “Young modulus (Gpa)”.
[ガラス転移温度測定]
ガラス転移温度(Tg)は、示差走査熱量法(DSC;Differential Scanning Calorimeter)により測定した。
[Glass transition temperature measurement]
The glass transition temperature (Tg) was measured by a differential scanning calorimetry (DSC).
[線膨張係数(CTE)の評価]
所定の温度で熱硬化処理した感光性樹脂膜について、熱機械的分析装置TMA/SS-7100(エスアイアイ・ナノテクノロジー株式会社製)を用いて、熱機械分析により、荷重5g、昇温速度10℃/分、窒素雰囲気下(流量20ml/分)、温度50〜450℃の範囲における試験片伸びの測定を行い、100〜300℃の感光性樹脂膜のCTEを求めた。その結果を「CTE (-ppm/K)」として表3〜4に示す。
[Evaluation of linear expansion coefficient (CTE)]
The photosensitive resin film thermoset at a predetermined temperature is subjected to a thermomechanical analysis using a thermomechanical analyzer TMA / SS-7100 (manufactured by SII Nanotechnology Co., Ltd.). The elongation of the test piece was measured in a temperature range of 50 to 450 ° C. under a nitrogen atmosphere (flow rate 20 ml / min) at a temperature of 50 ° C./minute, and the CTE of the photosensitive resin film at 100 to 300 ° C. was obtained. The results are shown in Tables 3 to 4 as “CTE (−ppm / K)”.
上記結果に示したとおり、本発明の層間絶縁膜形成用感光性樹脂組成物を用いて形成した感光性樹脂膜は、破断伸度が高く、機械特性にすぐれていることがわかった。
中でも、架橋剤(D)としてアダクト型のブロックイソシアネート化合物を採用した実施例8、9、19及び20の感光性樹脂膜は、機械特性に加え耐熱性も良好であった。
As shown in the above results, it was found that the photosensitive resin film formed using the photosensitive resin composition for forming an interlayer insulating film of the present invention has a high elongation at break and excellent mechanical properties.
Among them, the photosensitive resin films of Examples 8, 9, 19 and 20 that employ an adduct type blocked isocyanate compound as the crosslinking agent (D) had good heat resistance in addition to mechanical properties.
Claims (7)
前記感光性樹脂組成物層を露光する工程と、
露光された前記感光性樹脂組成物層を現像して層間絶縁膜パターンを形成する工程と、
前記層間絶縁膜パターンを加熱硬化する工程と、を有する層間絶縁膜の形成方法。 A step of forming a photosensitive resin composition layer on the support using the photosensitive resin composition for forming an interlayer insulating film according to any one of claims 1 to 4,
Exposing the photosensitive resin composition layer;
Developing the exposed photosensitive resin composition layer to form an interlayer insulating film pattern; and
And a step of heat-curing the interlayer insulating film pattern.
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