JP6530574B2 - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
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- JP6530574B2 JP6530574B2 JP2018561365A JP2018561365A JP6530574B2 JP 6530574 B2 JP6530574 B2 JP 6530574B2 JP 2018561365 A JP2018561365 A JP 2018561365A JP 2018561365 A JP2018561365 A JP 2018561365A JP 6530574 B2 JP6530574 B2 JP 6530574B2
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- epoxy resin
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- 239000003822 epoxy resin Substances 0.000 title claims description 168
- 229920000647 polyepoxide Polymers 0.000 title claims description 168
- 239000000203 mixture Substances 0.000 title claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000003795 chemical substances by application Substances 0.000 claims description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 38
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 35
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 35
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 229920003986 novolac Polymers 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
- 239000005011 phenolic resin Substances 0.000 claims description 23
- 239000002966 varnish Substances 0.000 claims description 20
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 229920001568 phenolic resin Polymers 0.000 claims description 11
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 10
- 239000010408 film Substances 0.000 claims description 10
- 239000003566 sealing material Substances 0.000 claims description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000012790 adhesive layer Substances 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 239000012787 coverlay film Substances 0.000 claims description 5
- 239000011229 interlayer Substances 0.000 claims description 5
- 238000004382 potting Methods 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 16
- 239000011134 resol-type phenolic resin Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 description 65
- -1 dimethylmethylene group Chemical group 0.000 description 50
- 238000001723 curing Methods 0.000 description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 43
- 229910052799 carbon Inorganic materials 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 125000005843 halogen group Chemical group 0.000 description 36
- 150000001721 carbon Chemical group 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- 239000004593 Epoxy Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000011889 copper foil Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 235000013824 polyphenols Nutrition 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 9
- 238000007872 degassing Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920003987 resole Polymers 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000004687 hexahydrates Chemical class 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 0 CCC(C*(C)*1)*(*(C)C)C1OC Chemical compound CCC(C*(C)*1)*(*(C)C)C1OC 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920005672 polyolefin resin Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- UHXCHUWSQRLZJS-UHFFFAOYSA-N (4-dimethylsilylidenecyclohexa-2,5-dien-1-ylidene)-dimethylsilane Chemical compound C[Si](C)C1=CC=C([Si](C)C)C=C1 UHXCHUWSQRLZJS-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000003746 surface roughness Effects 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 238000007719 peel strength test Methods 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 239000013034 phenoxy resin Substances 0.000 description 2
- 229920006287 phenoxy resin Polymers 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical group C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
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- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 150000004980 phosphorus peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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Description
項1.
式(1):
飽和炭化水素環又は不飽和炭化水素環、あるいは
飽和炭化水素環及び/又は不飽和炭化水素環が2〜6個縮合又は2個連結した構造を有する環
であり、
RXa、RXb、RXc、及びRXdは、同一又は異なって、水素原子、低級アルキル基、低級アルコキシ基、低級アルケニル基、ハロゲン原子、又は式(3):
R2は、炭素数1〜18のアルキレン基を示し、この基は、ケイ素原子に直接結合した炭素原子を除く一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
R3は同一又は異なって、炭素数1〜18のアルキル基、炭素数2〜9のアルケニル基、シクロアルキル基、アリール基又はアラルキル基を示し、これらの基は、一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
mは0〜6の整数を示し、
nは0〜3の整数を示す。)で表される基を示し、
但し、RXa、RXb、RXc、及びRXdのうち、少なくとも1つは式(3)で表される基であり、
X環を構成する炭化水素環を構成する炭素原子であって且つRXa、RXb、RXc、及びRXdが結合していない炭素原子に結合した水素原子が、低級アルキル基、低級アルコキシ基、低級アルケニル基、又はハロゲン原子で置換されていてもよい。)
で表されるエポキシ樹脂とフェノール系硬化剤とを含有するエポキシ樹脂組成物。
項2.
前記飽和炭化水素環及び/又は不飽和炭化水素環が2個連結した構造を有する環が、
式(2):
項3.
前記飽和炭化水素環が炭素数4〜8の飽和炭化水素環であり、
前記不飽和炭化水素環が炭素数4〜8の不飽和炭化水素環である、
項1又は2に記載のエポキシ樹脂組成物。
項4.
式(1−iia):
R1は同一又は異なって、炭素数1〜18のアルキル基、炭素数2〜9のアルケニル基、シクロアルキル基、アリール基又はアラルキル基を示し、これらの基は、一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
R2は同一又は異なって、炭素数1〜18のアルキレン基を示し、この基は、ケイ素原子に直接結合した炭素原子を除く一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
R3は同一又は異なって、炭素数1〜18のアルキル基、炭素数2〜9のアルケニル基、シクロアルキル基、アリール基又はアラルキル基を示し、これらの基は、一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
mは0〜6の整数を示し、nは0〜3の整数を示す。)
で表されるエポキシ樹脂、並びに
式(1−iiia):
R1、R2、R3、m、及びnは前記に同じ。)
で表されるエポキシ樹脂
からなる群より選択される少なくとも1種のエポキシ樹脂とフェノール系硬化剤とを含有する、項1に記載のエポキシ樹脂組成物。
項5.
フェノール系硬化剤が、ノボラック型フェノール樹脂、レゾール型フェノール樹脂、及びアラルキル型フェノール樹脂からなる群より選択される少なくとも1種の樹脂である、項1〜4のいずれかに記載のエポキシ樹脂組成物。
項6.
フェノール系硬化剤が、式(7):
式(8):
項7.
さらに硬化促進剤を含有する、項1〜6のいずれかに記載のエポキシ樹脂組成物。
項8.
項1〜7のいずれかに記載のエポキシ樹脂組成物及び有機溶媒を含むワニス。
項9.
項1〜7のいずれかに記載のエポキシ樹脂組成物の硬化物。
項10.
項1〜7のいずれかに記載のエポキシ樹脂組成物、項8に記載のワニス、又は項9に記載の硬化物が用いられている(好ましくは、含む)、半導体封止体、液状封止材、ポッティング材、シール材、層間絶縁膜、接着層、カバーレイフィルム、電磁波シールドフィルム、プリント基板材料又は複合材料。
項11.
半導体封止体、液状封止材、ポッティング材、シール材、層間絶縁膜、接着層、カバーレイフィルム、電磁波シールドフィルム、プリント基板材料又は複合材料の用途に用いられる、項1〜7のいずれかに記載のエポキシ樹脂組成物、項8に記載のワニス、又は項9に記載の硬化物。
項12.
半導体封止体、液状封止材、ポッティング材、シール材、層間絶縁膜、接着層、カバーレイフィルム、電磁波シールドフィルム、プリント基板材料又は複合材料を製造するための、項1〜7のいずれかに記載のエポキシ樹脂組成物、項8に記載のワニス、又は項9に記載の硬化物の使用。
で示される4価の基として、特に好ましくは以下の式で表される基が挙げられる。すなわち、
で表される基である。
m=1の場合は
で表される基である場合、式(1)で表されるエポキシ樹脂として、式(1−X2)
R1、R2、R3、m、及びnは前記に同じ。〕
で表されるエポキシ樹脂を好ましく包含する。なお、R1、R2、R3、m、及びnは、いずれも、それぞれ同一又は異なっていてよく、同一であることが好ましい。
で表される基である。
で表されるエポキシ樹脂を好ましく包含する。なお、R1、R2、R3、m、及びnは、いずれも、それぞれ同一又は異なっていてよく、同一であることが好ましい。
で表される基である。
で表されるエポキシ樹脂を包含する。なお、R1、R2、R3、m、及びnは、いずれも、それぞれ同一又は異なっていてよく、同一であることが好ましい。
で表される基が挙げられる。
で表される化合物が挙げられる。
上記式(1−IIa)で表されるエポキシ樹脂のうち、さらに好ましいものとして、式(1−IIa1):
又は式(1−IIa2):
で表されるエポキシ樹脂が例示できる。なお、R1は同一又は異なっていてよく、同一であることが好ましい。
で表されるエポキシ樹脂を挙げることもできる。なお、R1、R2、R3、及びnは、いずれも、それぞれ同一又は異なっていてよく、同一であることが好ましい。
式(1−IIb)において、Xiiが1,4−フェニレン基又は式(2g−iia’)で表される基(好ましくは1,4−フェニレン基)であり、R1が同一又は異なって(好ましくは同一で)炭素数1〜3のアルキル基(特にメチル基)であり、nが共に0(すなわち環はR3で置換されていない)であり、R2が同一又は異なって(好ましくは同一で)炭素数2〜6のアルキレン基(好ましくはジメチレン基:−(CH2)2−)であるものがより好ましい。
で表されるエポキシ樹脂を挙げることもできる。なお、R1、R2、R3、及びnは、いずれも、それぞれ同一又は異なっていてよく、同一であることが好ましい。
式(1−IIIa)において、Xiiiが
又は式(5−iva):
又は式(5−ia):
で表される化合物を用いることにより、上記式(1−iiia)又は(1−iva)で表されるエポキシ樹脂や1個の式(3)の基が炭化水素環に結合した構造を有するエポキシ樹脂を製造することもできる。また、これらの化合物の構造において、Xi〜Xivが、それぞれ、X環から1個の水素原子を除いて得られる1価の基、X環から2個の水素原子を除いて得られる2価の基、X環から3個の水素原子を除いて得られる3価の基、又はX環から4個の水素原子を除いて得られる4価の基、に置換された構造の化合物を用いることで、式(1)で示される種々の化合物を製造することができる。
量部、好ましくは0.0005〜5質量部である。
できる。
なお、pは平均値で好ましくは2〜20を示し、より好ましくは3〜10を示す。
硬化促進剤の使用量は、エポキシ樹脂組成物中のエポキシ樹脂100質量部に対して、好ましくは0.01〜10.0質量部であり、より好ましくは0.1〜5質量部である。
攪拌機、温度計及び冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、アリルグリシジルエーテル5.9g、ヘキサクロロ白金酸六水和物の2wt%エタノール溶液0.05g、トルエン100gを仕込み、液温を70℃まで昇温させた。その後、1,4−ビス(ジメチルシリル)ベンゼン5.0gを15分間で滴下し、引続き、90℃で4時間攪拌した。トルエンを濃縮により除去後、無色透明液体の1,4−ビス[(2,3−エポキシプロピルオキシプロピル)ジメチルシリル]ベンゼン(エポキシ樹脂A)10.3g(エポキシ当量211g/eq)を取得した。
攪拌機、温度計及び冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、1,2−エポキシ−5−ヘキセン5.0g、ヘキサクロロ白金酸六水和物の2wt%エタノール溶液0.05g、トルエン100gを仕込み、液温を70℃まで昇温させた。その後、1,4−ビス(ジメチルシリル)ベンゼン5.0gを15分間で滴下し、引続き、90℃で5時間攪拌した。トルエンを濃縮により除去後、無色透明液体の1,4−ビス[(2,3−エポキシブチル)ジメチルシリル]ベンゼン(エポキシ樹脂B)9.5g(エポキシ当量195g/eq)を取得した。
攪拌機、温度計及び冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、1,2−エポキシ−4−ビニルシクロヘキサン6.4g、ヘキサクロロ白金酸六水和物の2wt%エタノール溶液0.05g、トルエン100gを仕込み、液温を70℃まで昇温させた。その後、1,4−ビス(ジメチルシリル)ベンゼン5.0gを15分間で滴下し、引続き、90℃で4時間攪拌した。トルエンを濃縮により除去後、無色透明液体の1,4−ビス{[2−(3,4−エポキシシクロヘキシル)エチル]ジメチルシリル}ベンゼン(エポキシ樹脂C)10.8g(エポキシ当量221g/eq)を取得した。
攪拌機、温度計及び冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、1,2−エポキシ−4−ビニルシクロヘキサン4.3g、ヘキサクロロ白金酸六水和物の2wt%エタノール溶液0.05g、トルエン250gを仕込み、液温を70℃まで昇温させた。その後、ビス[(p−ジメチルシリル)フェニル]エーテル5.0gを15分間で滴下し、引続き、90℃で6時間攪拌した。トルエンを濃縮により除去後、無色透明液体の4,4’−ビス{[2−(3,4−エポキシシクロヘキシル)エチル]ジメチルシリル}ジフェニルエーテル(エポキシ樹脂D)8.9g(エポキシ当量267g/eq)を取得した。
攪拌機、温度計及び冷却器を備え付けた200mL容の四つ口フラスコに、窒素雰囲気下で、1,2−エポキシ−4−ビニルシクロヘキサン7.4g、ヘキサクロロ白金酸六水和物の2wt%エタノール溶液0.05g、トルエン250gを仕込み、液温を70℃まで昇温させた。その後、1,3,5−トリス(ジメチルシリル)ベンゼン5.0gを15分間で滴下し、引続き、90℃で6時間攪拌した。トルエンを濃縮により除去後、無色透明液体の1,3,5−トリス{[2−(3,4−エポキシシクロヘキシル)エチル]ジメチルシリル}ベンゼン(エポキシ樹脂E)11.8g(エポキシ当量208g/eq)を取得した。
はじめに、本実施例、比較例で用いた原材料をまとめて示す。
・エポキシ樹脂F:三菱化学社製Bis−A型エポキシ樹脂(グレード828)(エポキシ当量189g/eq)
・エポキシ樹脂G:ダイセル社製脂環式エポキシ樹脂(セロキサイド2021P;一般名は3',4'-エポキシシクロヘキシルメチル 3,4-エポキシシクロヘキサンカルボキシレート
)(エポキシ当量137g/eq)
・エポキシ樹脂H:脂環式エポキシ樹脂(FOLDIE−201、日産化学工業社製)(エポキシ当量285g/eq)
・フェノール系硬化剤:フェノールノボラック樹脂(TD−2131、DIC社製)
・硬化促進剤:トリフェニルホスフィン(TPP、東京化成工業社製)
フェノールノボラック樹脂47質量部をアセトン47質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂A100質量部、TPP2質量部加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂49質量部をアセトン49質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂B100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂49質量部をアセトン49質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂C100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂41質量部をアセトン49質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂D100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂54質量部をアセトン49質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂E100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂55質量部をアセトン55質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂F100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂76質量部をアセトン76質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂G100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
フェノールノボラック樹脂36質量部をアセトン36質量部に加え、マグネチックスターラーにて、室温(25℃)で30分間攪拌し溶解させた。そこへ、エポキシ樹脂H100質量部、TPP2質量部を加え均一に混合した。その後、充分に脱気することでエポキシ樹脂組成物のワニスを調製した。
実施例1〜5、比較例1〜3で得られたワニスを電解銅箔(古河電気工業社製、FHG−WS、処理面のRz=1.2μm)に塗布し、室温で1時間減圧乾燥することで銅箔付き接着フィルムを形成した。この樹脂面に研磨したアルミニウム板を張り合わせて、100℃で1時間、120℃で2時間、150℃で2時間加熱して硬化させた。硬化後、幅1cmになるようにカッターで切れ目を入れ、90度ピール強度試験片とした。得られた試験片について、AGS−X(島津製作所社製)を用いて、試験速度50mm/minの条件で90度ピール強度試験を実施した。
実施例1〜5、比較例1〜3で得られたワニスをTPX板(三井化学社製、厚さ2mm)上に塗布し、室温で1時間減圧乾燥後、100℃で1時間、120℃で2時間、150℃で2時間加熱して硬化させた。次いで、硬化物を幅30mm×長さ30mm×厚さ0.5mmのサイズに切り出し試験片とした。得られた試験片は、誘電率測定装置(インピーダンスアナライザー、アジレント社製)を用いて、25℃にて、比誘電率(1GHz)及び誘電正接(1GHz)を測定した。また、誘電率測定装置の校正は、PTFEを用いて行った。
Claims (10)
- 式(1−iia):
R 1 は同一又は異なって、炭素数1〜18のアルキル基、炭素数2〜9のアルケニル基、シクロアルキル基、アリール基又はアラルキル基を示し、これらの基は、一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
R 2 は同一又は異なって、炭素数1〜18のアルキレン基を示し、この基は、ケイ素原子に直接結合した炭素原子を除く一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
R 3 は同一又は異なって、炭素数1〜18のアルキル基、炭素数2〜9のアルケニル基、シクロアルキル基、アリール基又はアラルキル基を示し、これらの基は、一部の炭素原子が、酸素原子及び窒素原子からなる群より選ばれる少なくとも1種の原子で置換されていてもよく、
mは0〜6の整数を示し、
nは0〜3の整数を示す。)
で表されるエポキシ樹脂、
式(1−iiia):
R 1 、R 2 、R 3 、m、及びnは前記に同じ。)
で表されるエポキシ樹脂、並びに
式(1−iva):
R 1 、R 2 、R 3 、m、及びnは前記に同じ。)
で表されるエポキシ樹脂
からなる群より選択される少なくとも1種のエポキシ樹脂とフェノール系硬化剤とを含有するエポキシ樹脂組成物。 - 前記飽和炭化水素環が炭素数4〜8の飽和炭化水素環であり、
前記不飽和炭化水素環が炭素数4〜8の不飽和炭化水素環である、
請求項1に記載のエポキシ樹脂組成物。 - 式(1−IIa)で表されるエポキシ樹脂が、
X ii が、1,4−フェニレン基又は式(2 g −iia’):
式(1−IIb)で表されるエポキシ樹脂が、
X ii が1,4−フェニレン基又は式(2 g −iia’):
式(1−IIIa)で表されるエポキシ樹脂が、
X iii が
請求項3に記載のエポキシ樹脂組成物。 - フェノール系硬化剤が、ノボラック型フェノール樹脂、レゾール型フェノール樹脂、及びアラルキル型フェノール樹脂からなる群より選択される少なくとも1種の樹脂である、請求項1〜4のいずれかに記載のエポキシ樹脂組成物。
- さらに硬化促進剤を含有する、請求項1〜6のいずれかに記載のエポキシ樹脂組成物。
- 請求項1〜7のいずれかに記載のエポキシ樹脂組成物及び有機溶媒を含むワニス。
- 請求項1〜7のいずれかに記載のエポキシ樹脂組成物の硬化物。
- 請求項1〜7のいずれかに記載のエポキシ樹脂組成物、請求項8に記載のワニス、又は請求項9に記載の硬化物が用いられている、半導体封止体、液状封止材、ポッティング材、シール材、層間絶縁膜、接着層、カバーレイフィルム、電磁波シールドフィルム、プリント基板材料又は複合材料。
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JPWO2018131567A1 (ja) | 2019-04-25 |
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WO2018131567A1 (ja) | 2018-07-19 |
CN110177819A (zh) | 2019-08-27 |
US20190352448A1 (en) | 2019-11-21 |
TW201829529A (zh) | 2018-08-16 |
EP3569627A1 (en) | 2019-11-20 |
US11292872B2 (en) | 2022-04-05 |
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