JP5655451B2 - 熱硬化性樹脂組成物およびプリント配線板用層間接着フィルム - Google Patents
熱硬化性樹脂組成物およびプリント配線板用層間接着フィルム Download PDFInfo
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- JP5655451B2 JP5655451B2 JP2010206638A JP2010206638A JP5655451B2 JP 5655451 B2 JP5655451 B2 JP 5655451B2 JP 2010206638 A JP2010206638 A JP 2010206638A JP 2010206638 A JP2010206638 A JP 2010206638A JP 5655451 B2 JP5655451 B2 JP 5655451B2
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MNUSMUGFHGAOIW-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCCC1(C(O)=O)C(O)=O MNUSMUGFHGAOIW-UHFFFAOYSA-N 0.000 description 1
- JEBXNNPMFYXVHS-UHFFFAOYSA-N cyclohexane-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1C(O)=O JEBXNNPMFYXVHS-UHFFFAOYSA-N 0.000 description 1
- WTNDADANUZETTI-UHFFFAOYSA-N cyclohexane-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1 WTNDADANUZETTI-UHFFFAOYSA-N 0.000 description 1
- FTHDNRBKSLBLDA-UHFFFAOYSA-N cyclohexane-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)CC(C(O)=O)C1 FTHDNRBKSLBLDA-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- MGQFVQQCNPBJKC-UHFFFAOYSA-N dibutoxy(diethyl)silane Chemical compound CCCCO[Si](CC)(CC)OCCCC MGQFVQQCNPBJKC-UHFFFAOYSA-N 0.000 description 1
- GQNWJCQWBFHQAO-UHFFFAOYSA-N dibutoxy(dimethyl)silane Chemical compound CCCCO[Si](C)(C)OCCCC GQNWJCQWBFHQAO-UHFFFAOYSA-N 0.000 description 1
- OSMIWEAIYFILPL-UHFFFAOYSA-N dibutoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCCCC)(OCCCC)C1=CC=CC=C1 OSMIWEAIYFILPL-UHFFFAOYSA-N 0.000 description 1
- VULDKXCHNPRZCS-UHFFFAOYSA-N dibutoxy-ethyl-methylsilane Chemical compound CCCCO[Si](C)(CC)OCCCC VULDKXCHNPRZCS-UHFFFAOYSA-N 0.000 description 1
- NIGBFWLJCRFVJQ-UHFFFAOYSA-N dibutoxy-methyl-phenylsilane Chemical compound CCCCO[Si](C)(OCCCC)C1=CC=CC=C1 NIGBFWLJCRFVJQ-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- UWGJCHRFALXDAR-UHFFFAOYSA-N diethoxy-ethyl-methylsilane Chemical compound CCO[Si](C)(CC)OCC UWGJCHRFALXDAR-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- BZCJJERBERAQKQ-UHFFFAOYSA-N diethyl(dipropoxy)silane Chemical compound CCCO[Si](CC)(CC)OCCC BZCJJERBERAQKQ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- ZIDTUTFKRRXWTK-UHFFFAOYSA-N dimethyl(dipropoxy)silane Chemical compound CCCO[Si](C)(C)OCCC ZIDTUTFKRRXWTK-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- SLAYMDSSGGBWQB-UHFFFAOYSA-N diphenyl(dipropoxy)silane Chemical compound C=1C=CC=CC=1[Si](OCCC)(OCCC)C1=CC=CC=C1 SLAYMDSSGGBWQB-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011883 electrode binding agent Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZVJXKUWNRVOUTI-UHFFFAOYSA-N ethoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 ZVJXKUWNRVOUTI-UHFFFAOYSA-N 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- KUCGHDUQOVVQED-UHFFFAOYSA-N ethyl(tripropoxy)silane Chemical compound CCCO[Si](CC)(OCCC)OCCC KUCGHDUQOVVQED-UHFFFAOYSA-N 0.000 description 1
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- GXAOCGRUWCYNML-UHFFFAOYSA-N ethyl-methyl-dipropoxysilane Chemical compound CCCO[Si](C)(CC)OCCC GXAOCGRUWCYNML-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910003471 inorganic composite material Inorganic materials 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 239000005453 ketone based solvent Substances 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- BKXVGDZNDSIUAI-UHFFFAOYSA-N methoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC)C1=CC=CC=C1 BKXVGDZNDSIUAI-UHFFFAOYSA-N 0.000 description 1
- 238000006198 methoxylation reaction Methods 0.000 description 1
- 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 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- JQYGMRTZHJTQAC-UHFFFAOYSA-N methyl-phenyl-dipropoxysilane Chemical compound CCCO[Si](C)(OCCC)C1=CC=CC=C1 JQYGMRTZHJTQAC-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KADGVXXDDWDKBX-UHFFFAOYSA-N naphthalene-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C21 KADGVXXDDWDKBX-UHFFFAOYSA-N 0.000 description 1
- WRYWBRATLBWSSG-UHFFFAOYSA-N naphthalene-1,2,4-tricarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C21 WRYWBRATLBWSSG-UHFFFAOYSA-N 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- YXXLZRRIAHYCCY-UHFFFAOYSA-N phenanthrene-1,3,9,10-tetracarboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)=CC(C(O)=O)=C3C(C(O)=O)=C(C(O)=O)C2=C1 YXXLZRRIAHYCCY-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229910003470 tongbaite Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 150000005219 trimethyl ethers Chemical class 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- RTMBXAOPKJNOGZ-UHFFFAOYSA-N tris(2-methylphenyl) borate Chemical compound CC1=CC=CC=C1OB(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C RTMBXAOPKJNOGZ-UHFFFAOYSA-N 0.000 description 1
- FYAMVEZOQXNCIE-UHFFFAOYSA-N tris(3-methylphenyl) borate Chemical compound CC1=CC=CC(OB(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 FYAMVEZOQXNCIE-UHFFFAOYSA-N 0.000 description 1
- ROEKPHSQKWBJKS-UHFFFAOYSA-N tris(4-methylphenyl) borate Chemical compound C1=CC(C)=CC=C1OB(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 ROEKPHSQKWBJKS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Production Of Multi-Layered Print Wiring Board (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesive Tapes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
ポリイミド樹脂を樹脂濃度が0.5g/dlとなるようにN−メチル−2−ピロリドンに溶解して樹脂溶液を得た。樹脂溶液の溶液粘度、及び、溶媒粘度(N−メチル−2−ピロリドンの粘度)を30℃で、ウベローデ型の粘度管により測定して、得られた測定値を下記の式にあてはめて求めた。
上記式中、V1 はウベローデ型粘度管により測定した溶液粘度を示し、V2 はウベローデ型粘度管により測定した溶媒粘度を示す。ここで、V1 及びV2 は樹脂溶液及び溶媒(N−メチル−2−ピロリドン)が粘度管のキャピラリーを通過する時間から求めた。また、V3 は、ポリマー濃度(g/dl)である。
2、4位で主鎖と結合したトリレン構造の含有量は、ポリイミド樹脂主鎖に2、4−位で結合したトリレン構造の分子量を150として、ポリイミド樹脂全体の重量に占めるトリレン構造の割合から算出することができる。
測定装置 : 東ソー株式会社製 HLC−8320GPC、UV8320
カラム : 東ソー株式会社製 SuperAWM−H×2本
検出器 : RI(示差屈折計)及びUV(254nm)
データ処理:東ソー株式会社製 EcoSEC−WorkStation
測定条件: カラム温度 40℃
溶媒 DMF
流速 0.35ml/分
標準 :ポリスチレン標準試料にて検量線作成
試料 :樹脂固形分換算で0.2重量%のDMF溶液をマイクロフィルターでろ過したもの(注入量:10μl)
攪拌装置、温度計およびコンデンサーを付けたフラスコに、DMAC(ジメチルアセトアミド)213.2gとTDI(トリレンジイソシアネート)6.29g(0.036モル)、TODI(4,4´−ジイソシアネート−3,3´−ジメチル−1,1´−ビフェニル)37.8g(0.143モル)とTMA(無水トリメリット酸)29.0g(0.151モル)、BTDA(ベンゾフェノン−3,3′,4,4′−テトラカルボン酸二無水物、)12.2g(0.038モル)とを仕込み、攪拌を行いながら発熱に注意して1時間かけて150℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度が2Pa・sの樹脂固形分20%で溶液酸価が16(KOHmg/g)のポリイミド樹脂の溶液(ポリイミド樹脂がDMACに溶解した樹脂組成物)を得た。これをポリイミド樹脂(A1)の溶液と略記する。尚、その値から算出された樹脂の固形分酸価は64(KOHmg/g)であった。また、ゲルパーミエーションクロマトグラフィー(GPC)の測定の結果、重量平均分子量10000であった。
第1表に示す配合割合とした以外は合成例1と同様にしてポリイミド樹脂(A2)、(A4)及びポリイミド樹脂(A5)の溶液、比較対照用ポリイミド樹脂(a1)、(a3)及び(a4)の溶液を得た。合成例1と同様にビフェニル骨格の含有量、対数粘度、重量平均分子量及び固形分酸価を第1表に示す。
BTDAのかわりにBPDA(BPDA:ビフェニル−3,3´,4,4´−テトラカルボン酸無水物)を用い、さらに第1表に示す配合割合とした以外は合成例1と同様にしてポリイミド樹脂(A3)の溶液を得た。合成例1と同様にビフェニル骨格の含有量、対数粘度、重量平均分子量及び固形分酸価を第1表に示す。
攪拌装置、温度計およびコンデンサーを付けたフラスコに、GBL(ガンマブチロラクトン)1422.8gとMDI(ジフェニルメタンジイソシアネート)250g(1.0モル)とTMA(無水トリメリット酸)134.3(0.7モル)とTMA−H(シクロヘキサン−1,3,4−トリカルボン酸−3,4−無水物)59.4g(0.3モル)とを仕込み、攪拌を行いながら発熱に注意して80℃に昇温し、この温度で1時間かけて溶解、反応させ、更に2時間かけて160℃まで昇温した後、この温度で5時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は茶色の透明液体となった。25℃での粘度が10Pa・sの樹脂固形分20%で溶液酸価が1.8(KOHmg/g)のポリイミド樹脂(a5)の溶液(ポリイミド樹脂がγーブチロラクトンに溶解した樹脂組成物)を得た。尚、樹脂の酸価は1.8(KOHmg/g)であった。また、ゲルパーミエーションクロマトグラフィー(GPC)の測定の結果、重量平均分子量64000であった。
測定不能:合成中、析出物が沈殿し、均一溶液として得られなかった為、測定できなかった。
第2表〜第4表に示した配合にて本発明の熱硬化性樹脂組成物1〜11及び比較対照用熱硬化性樹脂組成物1´〜7´を得た。得られた組成物の硬化物のTG、線膨張係数及び溶融性の評価を行った。結果を第2〜第5表に示す。
1.試験片の作製
熱硬化性樹脂組成物を硬化後に得られる塗膜の膜厚が30μmになるようにブリキ基板上に塗装した。次いで、この塗装板を50℃の乾燥機で30分間、100℃の乾燥機で30分間、200℃の乾燥機で60分間乾燥して塗膜(フィルム)を作成した。室温まで冷却した後、塗膜(フィルム)を所定の大きさに切り出し、基板から単離して測定用試料とした。
セイコー電子(株)製熱分析システムTMA−SS6000を用いて、試料長10mm、昇温速度10℃/分、荷重30mNの条件でTMA(Thermal Mechanical Analysis)法により測定した。なお、TGは、TMA測定での温度−寸法変化曲線からその変極点を求め、その温度をTGとした。さらに線膨張係数に使用した温度域は20〜150℃での試料長の変位より求めた。TGが高いほど耐熱性に優れ線膨張係数が小さいほど寸法安定性に優れることを示す。
1.接着フィルムの作成
次に、熱硬化性樹脂組成物をPETフィルム(厚さ125μm)上に、乾燥後の樹脂組成物層の厚みが25μmとなるようにアプリケーターにて均一に塗布し、100℃で5分間乾燥させ、接着フィルムを得た。
あらかじめ120℃に加熱した電解銅箔(厚さ18μm、表面粗さ:M面Rz 7.4μm, S面Ra 0.21μm)に上記の接着フィルムを樹脂面が銅と接するように重ね合わせ、0.1MPaの圧力にて1分間熱プレスした。その後、PETフィルムをはがし、さらに200℃にて60分加熱することで樹脂組成物を本硬化させた。この試験片に対し、JIS K 5400 8.5.2(付着性 碁盤目テープ法)に従いテープ剥離試験を実施し、溶融接着性として以下の評価基準にて評価を行った。
○ :本硬化後、テープ剥離を実施して欠損部分の面積が試験実施面積に対して5%以上。
× :本硬化前、PETフィルムをはがした段階で樹脂が銅箔に全く付着していない。
TDI:2,4−トリレンジイソシアネート
TODI:4,4´−ジイソシアネート−3,3´−ジメチル−1,1´−ビフェニル
TMA:無水トリメリット酸
BTDA:ベンゾフェノンテトラカルボン酸無水物
BPDA:ビフェニル−3,3´,4,4´−テトラカルボン酸無水物
HCA−HQ:10−(2,5−ジヒドロキシフェニル)−10H−9−オキサ−10−ホスファフェナントレン−10−オキシド
850S:DIC(株)製 ビスフェノールA型液状エポキシ樹脂 エピクロン850−S(エポキシ当量 188g/eq)
EXA−4710:DIC(株)製 ナフタレン型エポキシ樹脂 エピクロンEXA−4710(エポキシ当量 173 g/eq)
N−680:DIC(株)製 クレゾールノボラック型エポキシ樹脂 エピクロンN−680(エポキシ当量 211 g/eq)
YX4000:三菱化学(株)製 ビフェニル型エポキシ樹脂 YX4000(エポキシ当量 187 g/eq)
アルコキシ化メラミン樹脂:メトキシ化ヘキサメチロールメラミン樹脂〔数平均分子量600、メチロール化率100%、粘度Z(25℃、ガードナー法)〕
Claims (14)
- 5員環イミド骨格に直結するビフェニル骨格を有し、該ビフェニル骨格の含有率が20〜45質量%で、且つ、対数粘度が0.2〜0.61dl/gであるポリイミド樹脂(A)と、エポキシ樹脂(B)と、アルコキシ化メラミン樹脂(C)とを含有する熱硬化性樹脂組成物であって、
前記エポキシ樹脂(B)が、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビフェニル型エポキシ樹脂及びナフタレン型エポキシ樹脂からなる群から選ばれる1種以上のエポキシ樹脂であり、
前記ポリイミド樹脂(A)がアルキレン構造を有さないポリイミド樹脂であることを特徴とする熱硬化性樹脂組成物。 - 前記ポリイミド樹脂(A)が、ビフェニル骨格の含有率が25〜40質量%で、且つ、対数粘度が0.2〜0.61dl/gである請求項1記載の熱硬化性樹脂組成物。
- 前記エポキシ樹脂(B)の含有量が、前記ポリイミド樹脂(A)100質量部に対して10〜100質量部である請求項1記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)が、更にベンゾフェノン構造を有するポリイミド樹脂である請求項1記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)が、更にトリレン構造を有するポリイミド樹脂である請求項1または4記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)がビフェニル骨格を有するポリイソシアネートと酸無水物とを反応させて得られるポリイミド樹脂である請求項1〜5のいずれか1項記載の熱硬化型ポリイミド樹脂組成物。
- 前記ビフェニル骨格を有するポリイソシアネートがトリジンジイソシアネートまたはトリジンジイソシアネートから誘導されるポリイソシアネートである請求項6記載の熱硬化型ポリイミド樹脂組成物。
- エポキシ樹脂(B)の150度における粘度が12Pa・s以下である請求項1記載の熱硬化性樹脂組成物。
- 硬化物の線膨張係数が50ppm/℃以下である請求項1記載の熱硬化性樹脂組成物。
- 前記アルコキシ化メラミン樹脂(C)がメトキシ化メチロールメラミン樹脂である請求項1記載の熱硬化性樹脂組成物。
- 前記アルコキシ化メラミン樹脂(C)の含有量が、前記ポリイミド樹脂(A)100質量部に対して3〜100質量部である請求項1記載の熱硬化性樹脂組成物。
- 更に、ホウ酸またはホウ酸エステル(D)を含有する請求項1記載の熱硬化性樹脂組成物。
- 前記ポリイミド樹脂(A)が、ジイソシアネートと酸無水物を反応させたものであり、
ジイソシアネートがトリレンジイソシアネートおよび4,4’−ジイソシアネート−3,3’−ジメチル−1,1’−ビフェニルであり、
酸無水物が無水トリメリット酸と、ベンゾフェノン−3,3’,4,4’−テトラカルボン酸二無水物及び/又はビフェニル−3,3’,4,4’−テトラカルボ酸無水物とである、請求項1〜12の何れか一項記載の熱可塑性樹脂組成物。 - 請求項1〜13のいずれか1項に記載の熱硬化性樹脂組成物により形成される層を、キャリアフィルム上に有することを特徴とするプリント配線板用層間接着フィルム。
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