JP2007262243A - Resin composition and semiconductor device manufactured using resin composition - Google Patents
Resin composition and semiconductor device manufactured using resin composition Download PDFInfo
- Publication number
- JP2007262243A JP2007262243A JP2006089497A JP2006089497A JP2007262243A JP 2007262243 A JP2007262243 A JP 2007262243A JP 2006089497 A JP2006089497 A JP 2006089497A JP 2006089497 A JP2006089497 A JP 2006089497A JP 2007262243 A JP2007262243 A JP 2007262243A
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- Prior art keywords
- compound
- meth
- resin composition
- acrylate
- group
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 53
- 239000004065 semiconductor Substances 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000524 functional group Chemical group 0.000 claims abstract description 21
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- 230000017525 heat dissipation Effects 0.000 claims description 7
- 150000001451 organic peroxides Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 75
- -1 maleimide amino acid Chemical class 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 229920005862 polyol Polymers 0.000 description 12
- 150000003077 polyols Chemical class 0.000 description 12
- 238000001723 curing Methods 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000035882 stress Effects 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- URLYGBGJPQYXBN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound OCC1CCC(COC(=O)C=C)CC1 URLYGBGJPQYXBN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003999 initiator Substances 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
- 238000004898 kneading Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 1
- MYOQALXKVOJACM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy pentaneperoxoate Chemical compound CCCCC(=O)OOOC(C)(C)C MYOQALXKVOJACM-UHFFFAOYSA-N 0.000 description 1
- ZORJPNCZZRLEDF-UHFFFAOYSA-N (3-methoxy-3-methylbutoxy)carbonyloxy (3-methoxy-3-methylbutyl) carbonate Chemical compound COC(C)(C)CCOC(=O)OOC(=O)OCCC(C)(C)OC ZORJPNCZZRLEDF-UHFFFAOYSA-N 0.000 description 1
- NLBJAOHLJABDAU-UHFFFAOYSA-N (3-methylbenzoyl) 3-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC(C(=O)OOC(=O)C=2C=C(C)C=CC=2)=C1 NLBJAOHLJABDAU-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- FYRCDEARNUVZRG-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CC(C)CC(C)(C)C1 FYRCDEARNUVZRG-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- OTMBZPVYOQYPBE-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclododecane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCCCCCCCC1 OTMBZPVYOQYPBE-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- CRJIYMRJTJWVLU-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 3-(5,5-dimethylhexyl)dioxirane-3-carboxylate Chemical compound CC(C)(C)CCCCC1(C(=O)OC(C)(C)CC(C)(C)C)OO1 CRJIYMRJTJWVLU-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- VJZBTBIZXCDAMV-UHFFFAOYSA-N 2-(1,3-dioxo-5,6,7,7a-tetrahydro-4h-isoindol-3a-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)NC(=O)C21CCOC(=O)C=C VJZBTBIZXCDAMV-UHFFFAOYSA-N 0.000 description 1
- XDVMJFWMHCWGLB-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-4-yl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC2=C1C(=O)NC2=O XDVMJFWMHCWGLB-UHFFFAOYSA-N 0.000 description 1
- GUMPIILNPLLYKX-UHFFFAOYSA-N 2-(2,5-dioxopyrrol-3-yl)ethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCC=1C(=O)NC(C1)=O GUMPIILNPLLYKX-UHFFFAOYSA-N 0.000 description 1
- PJABOTZVAHGVAF-UHFFFAOYSA-N 2-(2-cyclohexylpropan-2-yl)-7,7-dimethyloctaneperoxoic acid Chemical compound CC(C)(C)CCCCC(C(=O)OO)C(C)(C)C1CCCCC1 PJABOTZVAHGVAF-UHFFFAOYSA-N 0.000 description 1
- CHKCPIUYSMYEEW-UHFFFAOYSA-N 2-(2-cyclohexylpropan-2-ylperoxy)-2-ethylhexanoic acid Chemical compound CCCCC(CC)(C(O)=O)OOC(C)(C)C1CCCCC1 CHKCPIUYSMYEEW-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- AFNINTOPXLZTNX-UHFFFAOYSA-N 2-[2-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCCCC1CCO AFNINTOPXLZTNX-UHFFFAOYSA-N 0.000 description 1
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-UHFFFAOYSA-N 0.000 description 1
- VZHATSRCGGWIRE-UHFFFAOYSA-N 2-[3-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCCC(CCO)C1 VZHATSRCGGWIRE-UHFFFAOYSA-N 0.000 description 1
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- BZGMEGUFFDTCNP-UHFFFAOYSA-N 2-hydroperoxy-2-methylpentane Chemical compound CCCC(C)(C)OO BZGMEGUFFDTCNP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RTEZVHMDMFEURJ-UHFFFAOYSA-N 2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)C(C)(C)C RTEZVHMDMFEURJ-UHFFFAOYSA-N 0.000 description 1
- WXDJDZIIPSOZAH-UHFFFAOYSA-N 2-methylpentan-2-yl benzenecarboperoxoate Chemical compound CCCC(C)(C)OOC(=O)C1=CC=CC=C1 WXDJDZIIPSOZAH-UHFFFAOYSA-N 0.000 description 1
- JPHJRWUYXNIYEP-UHFFFAOYSA-N 2-methylpentan-2-yloxy 7,7-dimethyloctaneperoxoate Chemical compound CCCC(C)(C)OOOC(=O)CCCCCC(C)(C)C JPHJRWUYXNIYEP-UHFFFAOYSA-N 0.000 description 1
- NBASYSYSVRDGEF-UHFFFAOYSA-N 2-methylpentan-2-ylperoxycyclohexane Chemical compound CCCC(C)(C)OOC1CCCCC1 NBASYSYSVRDGEF-UHFFFAOYSA-N 0.000 description 1
- RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- ATYIZISYPACGCO-UHFFFAOYSA-N tributoxy-[3-(3-tributoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCSSCCC[Si](OCCCC)(OCCCC)OCCCC ATYIZISYPACGCO-UHFFFAOYSA-N 0.000 description 1
- VVKKLYJRUIYBJT-UHFFFAOYSA-N tributoxy-[3-(3-tributoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCSSSSCCC[Si](OCCCC)(OCCCC)OCCCC VVKKLYJRUIYBJT-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- NQRACKNXKKOCJY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSCCC[Si](OC)(OC)OC NQRACKNXKKOCJY-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Die Bonding (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
Abstract
Description
本発明は、樹脂組成物及び樹脂組成物を使用して作製した半導体装置に関するものである。 The present invention relates to a resin composition and a semiconductor device manufactured using the resin composition.
近年、半導体デバイスの高速化は著しく、多層配線部における配線抵抗と配線間の寄生容量に起因する信号伝搬速度の低下による伝送遅延が問題となってきている。こうした問題は、半導体デバイスの高集積化に伴う配線幅及び配線間隔の微細化につれて配線抵抗が上昇しかつ寄生容量が増大するので、益々顕著となる傾向にある。そこで、配線抵抗及び寄生容量の増大に基づく信号遅延を防止するために、従来のアルミニウム配線に代わり銅配線の導入が行われると共に、層間絶縁膜に比誘電率が二酸化シリコン膜の3.9より小さい低誘電率の絶縁膜の適用が行われている。特に設計基準が65nmから45nmへと構成素子の微細化が進む中で層間絶縁膜の比誘電率は2.0程度あるいはそれ以下の値が強く求められ、このために層間絶縁膜として膜内部の空孔率を高めることで比誘電率を小さくした多孔質絶縁膜が必要になってきている。
このような多孔質絶縁膜は、その構造上一般的に機械的強度か弱いという問題がある。すなわち従来の絶縁膜を使用した半導体素子に比較して外部からのストレスに対して敏感で、これまで問題とされなかったストレスでも絶縁膜の破壊に至る場合がある。
そこで発生するストレスを少なくするために、封止材料、ダイアタッチ材料といった半導体構成材料に対して低応力性のものが要求されると共に、半導体生産プロセスの見直しも行われている。
半導体素子をリードフレーム、有機基板といった支持体に接着するダイアタッチプロセスにおいてはダイアタッチ後に半導体素子と支持体の熱膨張率の異なりに基づく反りが発生するが、過度の反りは層間絶縁膜のダメージの原因となるため、反りの小さいダイアタッチ材料が求められると共に低温で硬化することが可能な硬化性に優れる材料が求められている。(例えば、特許文献1参照。)
一般に低温での硬化性をよくすると室温での粘度上昇も短時間でおこり、またワイヤボンド時、半田リフロー時などの高温プロセス下での接着力が低下するといった傾向があった。
Such a porous insulating film generally has a problem that its mechanical strength is weak because of its structure. That is, compared with a semiconductor element using a conventional insulating film, it is more sensitive to external stress, and the insulating film may be destroyed even by stress that has not been a problem until now.
In order to reduce the stress generated there, semiconductor constituent materials such as a sealing material and a die attach material are required to have low stress, and the semiconductor production process has been reviewed.
In a die attach process in which a semiconductor element is bonded to a support such as a lead frame or an organic substrate, warpage occurs due to the difference in coefficient of thermal expansion between the semiconductor element and the support after die attachment, but excessive warpage is damage to the interlayer insulating film. Therefore, there is a need for a die attach material with a small warpage and a material with excellent curability that can be cured at low temperatures. (For example, refer to Patent Document 1.)
In general, when the curability at low temperature is improved, the viscosity at room temperature increases in a short time, and the adhesive force tends to decrease under high temperature processes such as wire bonding and solder reflow.
本発明は、十分な低応力性、低温硬化性を有しながら高温での接着性及び保存性に優れる樹脂組成物並びに該樹脂組成物を半導体用ダイアタッチペースト又は放熱部材接着用材料として使用することで信頼性に優れた半導体装置を提供することである。 The present invention uses a resin composition that has sufficient low-stress properties and low-temperature curability while being excellent in adhesiveness and storage stability at high temperatures, and uses the resin composition as a die attach paste for semiconductors or a material for adhering heat dissipation members. Thus, it is to provide a semiconductor device having excellent reliability.
このような目的は、下記[1]〜[8]に記載の本発明により達成される。
[1]ラジカル重合可能な官能基を有する化合物(A)、重合開始剤(B)、銀粉(C)及びスルフィド結合を有する化合物(D)を含むことを特徴とする樹脂組成物。
[2]前記化合物(A)のラジカル重合可能な官能基がビニル基、(メタ)アクリロイル基、(メタ)アリル基、及びマレイミド基から選ばれる少なくとも1つである[1]項に記載の樹脂組成物。
[3]前記化合物(A)のラジカル重合可能な官能基が(メタ)アクリロイル基である[1]又は[2]項に記載の樹脂組成物。
[4]前記化合物(A)の分子量が500〜10000である[1]〜[3]項のいずれか1項に記載の樹脂組成物。
[5]前記重合開始剤(B)が有機過酸化物である[1]〜[4]項のいずれか1項に記載の樹脂組成物。
[6]前記化合物(D)がジスルフィド結合、トリスルフィド結合、及びテトラスルフィド結合から選ばれる少なくとも1つの結合を有する化合物である[1]〜[5]項のいずれか1項に記載の樹脂組成物。
[7]前記化合物(D)がアルコキシシラン基を有する化合物である[6]項に記載の樹脂組成物。
[8][1]〜[7]項のいずれか1項に記載の樹脂組成物を半導体用ダイアタッチペースト又は放熱部材接着用材料として用いて作製したことを特徴とする半導体装置。
Such an object is achieved by the present invention described in the following [1] to [8].
[1] A resin composition comprising a compound (A) having a radical polymerizable functional group, a polymerization initiator (B), silver powder (C), and a compound (D) having a sulfide bond.
[2] The resin according to item [1], wherein the radically polymerizable functional group of the compound (A) is at least one selected from a vinyl group, a (meth) acryloyl group, a (meth) allyl group, and a maleimide group. Composition.
[3] The resin composition according to item [1] or [2], wherein the radically polymerizable functional group of the compound (A) is a (meth) acryloyl group.
[4] The resin composition according to any one of [1] to [3], wherein the compound (A) has a molecular weight of 500 to 10,000.
[5] The resin composition according to any one of [1] to [4], wherein the polymerization initiator (B) is an organic peroxide.
[6] The resin composition according to any one of items [1] to [5], wherein the compound (D) is a compound having at least one bond selected from a disulfide bond, a trisulfide bond, and a tetrasulfide bond. object.
[7] The resin composition according to item [6], wherein the compound (D) is a compound having an alkoxysilane group.
[8] A semiconductor device produced by using the resin composition according to any one of items [1] to [7] as a die attach paste for a semiconductor or a material for adhering a heat dissipation member.
本発明の樹脂組成物は、良好な低温硬化性と良好な保存性とを有しかつ高接着性で応力緩和特性にも優れるため、ダイアタッチペースト又は放熱部材接着用材料として使用した場合、半導体素子のダメージが少なくまた得られた半導体装置は耐リフロー性に優れており、その結果高信頼性の半導体装置を得ることができる。 The resin composition of the present invention has good low-temperature curability and good storage stability, and has high adhesiveness and excellent stress relaxation characteristics. Therefore, when used as a die attach paste or a heat dissipation member adhesion material, a semiconductor The obtained semiconductor device has little element damage and has excellent reflow resistance. As a result, a highly reliable semiconductor device can be obtained.
本発明は、ラジカル重合可能な官能基を有する化合物、重合開始剤、銀粉及びスルフィド結合を有する化合物を含むことを特徴とする半導体素子又は放熱部材を支持体に接着する樹脂組成物で、特に低温硬化性と保存性に優れ、高接着性かつ弾性率が低く応力緩和特性に優れる樹脂組成物を提供するものである。ここで、支持体とは、半導体素子を接着する場合は、リードフレーム、有機基板などであり、放熱部材を接着する場合は、半導体素子、リードフレーム、有機基板、半導体製品などが挙げられるが、これらに限定されるものではない。
以下、本発明について詳細に説明する。
The present invention is a resin composition for adhering a semiconductor element or a heat dissipation member to a support, comprising a compound having a functional group capable of radical polymerization, a polymerization initiator, silver powder, and a compound having a sulfide bond, particularly at low temperatures. The present invention provides a resin composition having excellent curability and storage stability, high adhesion, low elastic modulus and excellent stress relaxation properties. Here, the support is a lead frame, an organic substrate or the like when bonding a semiconductor element, and a semiconductor element, a lead frame, an organic substrate, a semiconductor product, or the like when bonding a heat dissipation member, It is not limited to these.
Hereinafter, the present invention will be described in detail.
本発明に用いるラジカル重合可能な官能基を有する化合物(A)のラジカル重合可能な官能基としては、ビニル基、(メタ)アクリロイル基、(メタ)アリル基、マレイミド基などが挙げられ、これらの官能基は反応性に優れ低温硬化、短時間硬化に好適に使用される。なかでも好ましいのは(メタ)アクリロイル基である。1分子中の官能基の数としては硬化性の観点より2つ以上が好ましく、より好ましくは2つの場合である。また化合物(A)の分子量としては500〜10000が好ましい。より好ましくは500〜7000である。これより低いと硬化時の体積収縮が大きくなりすぎ、これより高いと粘度が高くなりすぎるためである。 Examples of the radically polymerizable functional group of the compound (A) having a radically polymerizable functional group used in the present invention include a vinyl group, a (meth) acryloyl group, a (meth) allyl group, and a maleimide group. The functional group has excellent reactivity and is suitably used for low temperature curing and short time curing. Of these, a (meth) acryloyl group is preferred. The number of functional groups in one molecule is preferably two or more, more preferably two from the viewpoint of curability. Moreover, as molecular weight of a compound (A), 500-10000 are preferable. More preferably, it is 500-7000. If it is lower than this, the volume shrinkage at the time of curing becomes too large, and if it is higher than this, the viscosity becomes too high.
このような化合物(A)としては、以下のものが例示されるがこれらに限定されるわけではない。ポリオールとラジカル重合可能な官能基及びカルボキシ基を有する化合物又はその誘導体との反応により得られる化合物やラジカル重合可能な官能基及び水酸基を有する化合物とポリイソシアネートとポリオールとを反応することで得られる化合物やラジカル重合可能な官能基及び水酸基を有する化合物とポリカルボン酸化合物とを反応することで得られる化合物などである。 Examples of such compound (A) include, but are not limited to, the following. A compound obtained by reacting a polyol with a compound having a radically polymerizable functional group and a carboxy group or a derivative thereof, or a compound having a radically polymerizable functional group and a hydroxyl group, a polyisocyanate and a polyol And a compound obtained by reacting a compound having a functional group capable of radical polymerization and a hydroxyl group with a polycarboxylic acid compound.
ポリオールとしては、ポリアルキレンオキサイドポリオール、ポリエステルポリオール、ポリカーボネートポリオール、ポリオールとポリイソシアネートとの反応により得られるポリオール、水酸基を有する(メタ)アクリレートと水酸基を有しない(メタ)アクリレートとの共重合により得られるポリオールなどが挙げられ、ポリオールとしてジオールを用いたものも好ましい。 Examples of the polyol include polyalkylene oxide polyol, polyester polyol, polycarbonate polyol, polyol obtained by reaction of polyol and polyisocyanate, and copolymerization of (meth) acrylate having a hydroxyl group and (meth) acrylate having no hydroxyl group. A polyol etc. are mentioned, What uses diol as a polyol is also preferable.
ラジカル重合可能な官能基及びカルボキシ基を有する化合物又はその誘導体としては、(メタ)アクリル酸、(メタ)アクリル酸エステル、マレイミドアミノ酸、マレイミドアミノ酸エステル、ジアリルエステル化合物などが挙げられる。 Examples of the compound having a functional group capable of radical polymerization and a carboxyl group or a derivative thereof include (meth) acrylic acid, (meth) acrylic acid ester, maleimide amino acid, maleimide amino acid ester, diallyl ester compound and the like.
ラジカル重合可能な官能基及び水酸基を有する化合物としては、アリルアルコール、水酸基を有するビニルエーテル、水酸基を有する(メタ)アクリル酸エステル、水酸基を有する(メタ)アクリル酸アミドなどが挙げられる。ポリイソシアネートとしては、イソホロンジイソシアネート、ノルボルネンジイソシアネートのように2官能で芳香族環を含まないものも好適に用いられる。 Examples of the compound having a radical polymerizable functional group and a hydroxyl group include allyl alcohol, vinyl ether having a hydroxyl group, (meth) acrylic acid ester having a hydroxyl group, and (meth) acrylic acid amide having a hydroxyl group. As the polyisocyanate, those which are bifunctional and do not contain an aromatic ring such as isophorone diisocyanate and norbornene diisocyanate are also preferably used.
ポリカルボン酸化合物としては、(メタ)アクリル酸とカルボキシ基を有しない(メタ)アクリル酸エステルとの共重合により得られるポリカルボン酸、ダイマー酸等の脂肪族ジカルボン酸、過剰のジカルボン酸とポリオール又はポリアミンとの反応で得られるポリカルボン酸などが挙げられる。ポリカルボン酸はカルボキシ基であってもハロゲン化物、酸無水物、エステル化物等、水酸基と反応可能な誘導体となっていてもかまわない。
中でも耐加水分解性に優れるポリカーボネートポリオールや水酸基を有する(メタ)アクリレートと水酸基を有しない(メタ)アクリレートとの共重合により得られるポリオールとラジカル重合可能な官能基及びカルボキシ基を有する化合物又はその誘導体との反応により得られる化合物は好適に用いられ、芳香族環を含まないものも特に好ましく用いられる。
Examples of polycarboxylic acid compounds include polycarboxylic acid obtained by copolymerization of (meth) acrylic acid and (meth) acrylic acid ester having no carboxy group, aliphatic dicarboxylic acid such as dimer acid, excess dicarboxylic acid and polyol Or the polycarboxylic acid etc. which are obtained by reaction with a polyamine are mentioned. The polycarboxylic acid may be a carboxy group or a derivative capable of reacting with a hydroxyl group, such as a halide, an acid anhydride, or an esterified product.
Among them, a polycarbonate polyol having excellent hydrolysis resistance, a polyol obtained by copolymerization of (meth) acrylate having a hydroxyl group and (meth) acrylate having no hydroxyl group, a compound having a radically polymerizable functional group and a carboxy group, or a derivative thereof The compound obtained by the reaction with is preferably used, and those not containing an aromatic ring are particularly preferably used.
本発明で用いる重合開始剤(B)は、不飽和結合を反応させるものであれば、その種類については特に限定されるものではない。
本発明の樹脂組成物は、通常蛍光灯等の照明下で使用されるので光重合開始剤が含まれていると使用中の反応により粘度上昇が観察されるため実質的に光重合開始剤を含有することは好ましくない。実質的にとは、粘度上昇が観察されない程度で光重合開始剤が微量に存在してもよく、好ましくは、含有しないことである。
The type of the polymerization initiator (B) used in the present invention is not particularly limited as long as it allows an unsaturated bond to react.
Since the resin composition of the present invention is usually used under illumination such as a fluorescent lamp, if a photopolymerization initiator is contained, an increase in viscosity is observed due to a reaction during use. It is not preferable to contain it. “Substantially” means that a small amount of the photopolymerization initiator may be present to such an extent that no increase in viscosity is observed, and it is preferably not contained.
本発明に用いる重合開始剤(B)は、有機過酸化物が好ましく、有機過酸化物とは、分子内に−O−O−結合を有し、加熱することにより遊離ラジカルを発生しうるものである。例えば、ケトンパーオキサイド類、パーオキシケタール類、ハイドロパーオキサイド類、ジアルキルパーオキサイド類、ジアシルパーオキサイド類、パーオキシジカーボネート類、パーオキシエステル類等が挙げられる。望ましいものとしては、急速加熱試験(試料1gを電熱板の上にのせ、4℃/分で昇温した時の分解開始温度)における分解温度が40〜140℃となるものが好ましい。分解温度が40℃未満だと、樹脂組成物の常温における保存性が悪くなり、140℃を越えると硬化時間が極端に長くなるため好ましくない。具体例としては、メチルエチルケトンパーオキサイド、メチルシクロヘキサノンパーオキサイド、メチルアセトアセテートパーオキサイド、アセチルアセトンパーオキサイド、1,1−ビス(t−ブチルパーオキシ)3,3,5−トリメチルシクロヘキサン、1,1−ビス(t−ヘキシルパーオキシ)シクロヘキサン、1,1−ビス(t−ヘキシルパーオキシ)3,3,5−トリメチルシクロヘキサン、1,1−ビス(t−ブチルパーオキシ)シクロヘキサン、2,2−ビス(4,4−ジ−t−ブチルパーオキシシクロヘキシル)プロパン、1,1−ビス(t−ブチルパーオキシ)シクロドデカン、n−ブチル4,4−ビス(t−ブチルパーオキシ)バレレート、2,2−ビス(t−ブチルパーオキシ)ブタン、1,1−ビス(t−ブチルパーオキシ)−2−メチルシクロヘキサン、t−ブチルハイドロパーオキサイド、P−メンタンハイドロパーオキサイド、1,1,3,3−テトラメチルブチルハイドロパーオキサイド、t−ヘキシルハイドロパーオキサイド、ジクミルパーオキサイド、2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキサン、α、α’−ビス(t−ブチルパーオキシ)ジイソプロピルベンゼン、t−ブチルクミルパーオキサイド、ジ−t−ブチルパーオキサイド、2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキシン−3、イソブチリルパーオキサイド、3,5,5−トリメチルヘキサノイルパーオキサイド、オクタノイルパーオキサイド、ラウロイルパーオキサイド、桂皮酸パーオキサイド、m−トルオイルパーオキサイド、ベンゾイルパーオキサイド、ジイソプロピルパーオキシジカーボネート、ビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート、ジ−3−メトキシブチルパーオキシジカーボネート、ジ−2−エチルヘキシルパーオキシジカーボネート、ジ−sec−ブチルパーオキシジカーボネート、ジ(3−メチル−3−メトキシブチル)パーオキシジカーボネート、ジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート、α、α’−ビス(ネオデカノイルパーオキシ)ジイソプロピルベンゼン、クミルパーオキシネオデカノエート、1,1,3,3,−テトラメチルブチルパーオキシネオデカノエート、1−シクロヘキシル−1−メチ−ルエチルパーオキシネオデカノエート、t−ヘキシルパーオキシネオデカノエート、t−ブチルパーオキシネオデカノエート、t−ヘキシルパーオキシピバレート、t−ブチルパーオキシピバレート、2,5−ジメチル−2,5−ビス(2−エチルヘキサノイルパーオキシ)ヘキサン、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルへキサノエート、1−シクロヘキシル−1−メチルエチルパーオキシ−2−エチルヘキサノエート、t−ヘキシルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシイソブチレート、t−ブチルパーオキシマレイックアシッド、t−ブチルパーオキシラウレート、t−ブチルパーオキシ−3,5,5−トリメチルヘキサノエート、t−ブチルパーオキシイソプロピルモノカーボネート、t−ブチルパーオキシ−2−エチルヘキシルモノカーボネート、2,5−ジメチル−2,5−ビス(ベンゾイルパーオキシ)ヘキサン、t−ブチルパーオキシアセテート、t−ヘキシルパーオキシベンゾエート、t−ブチルパーオキシ−m−トルオイルベンゾエート、t−ブチルパーオキシベンゾエート、ビス(t−ブチルパーオキシ)イソフタレート、t−ブチルパーオキシアリルモノカーボネート、3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン等が挙げられるが、これらは単独又は硬化性を制御するため2種類以上を混合して用いることもできる。特に限定されるわけではないが樹脂組成物中0.001重量%以上、2重量%以下含有されるのが好ましい。 The polymerization initiator (B) used in the present invention is preferably an organic peroxide, which has an —O—O— bond in the molecule and can generate free radicals upon heating. It is. Examples thereof include ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxydicarbonates, peroxyesters, and the like. As a desirable thing, what has a decomposition temperature of 40-140 degreeC in a rapid heating test (The decomposition start temperature when 1 g of samples are put on an electric heating board and it heated up at 4 degree-C / min) is preferable. If the decomposition temperature is less than 40 ° C., the preservability of the resin composition at normal temperature deteriorates, and if it exceeds 140 ° C., the curing time becomes extremely long, which is not preferable. Specific examples include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, acetylacetone peroxide, 1,1-bis (t-butylperoxy) 3,3,5-trimethylcyclohexane, 1,1-bis. (T-hexylperoxy) cyclohexane, 1,1-bis (t-hexylperoxy) 3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, 2,2-bis ( 4,4-di-t-butylperoxycyclohexyl) propane, 1,1-bis (t-butylperoxy) cyclododecane, n-butyl 4,4-bis (t-butylperoxy) valerate, 2,2 -Bis (t-butylperoxy) butane, 1,1-bis (t-butylpa Oxy) -2-methylcyclohexane, t-butyl hydroperoxide, P-menthane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-hexyl hydroperoxide, dicumyl peroxide, 2 , 5-dimethyl-2,5-bis (t-butylperoxy) hexane, α, α′-bis (t-butylperoxy) diisopropylbenzene, t-butylcumyl peroxide, di-t-butylperoxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, cinnamic acid Peroxide, m-toluoyl peroxide, Zoyl peroxide, diisopropyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-sec-butyl Peroxydicarbonate, di (3-methyl-3-methoxybutyl) peroxydicarbonate, di (4-t-butylcyclohexyl) peroxydicarbonate, α, α'-bis (neodecanoylperoxy) diisopropylbenzene , Cumylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxy Neodecanoate, t-butyl -Oxyneodecanoate, t-hexylperoxypivalate, t-butylperoxypivalate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylperoxy) hexane, 1,1,3 , 3-tetramethylbutylperoxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylper Oxy-2-ethylhexanoate, t-butylperoxyisobutyrate, t-butylperoxymaleic acid, t-butylperoxylaurate, t-butylperoxy-3,5,5-trimethylhexano Ate, t-butylperoxyisopropyl monocarbonate, t-butylperoxy-2-ethyl Silmonocarbonate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyacetate, t-hexylperoxybenzoate, t-butylperoxy-m-toluoylbenzoate, t- Examples thereof include butyl peroxybenzoate, bis (t-butylperoxy) isophthalate, t-butylperoxyallyl monocarbonate, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, and the like. These can be used alone or in combination of two or more in order to control curability. Although not particularly limited, it is preferably contained in the resin composition in an amount of 0.001% by weight to 2% by weight.
本発明で用いる銀粉(C)は、特に限定されるものではないが、ノズルを使用して樹脂組成物を吐出するディスペンス時のノズル詰まりを防ぐために平均粒径は30μm以下が好ましく、半導体装置の信頼性を維持するためにナトリウム、塩素といったイオン性の不純物が少ないことが好ましい。通常電子材料用として市販されている銀粉であれば、還元粉、アトマイズ粉等が入手可能で、好ましい粒径としては平均粒径が1μm以上、30μm以下である。下限値以下では樹脂組成物の粘度が高くなりすぎ、上限値以上では上述のようにディスペンス時にノズル詰まりの原因となりうるからであり、電子材料用以外の銀粉ではイオン性不純物の量が多い場合があるので注意が必要である。形状はフレーク状、球状等特に限定されないが、好ましくはフレーク状のものを使用し、通常樹脂組成物中70重量%以上、95重量%以下含まれる。銀粉の割合が下限値より少ない場合には導電性が悪化し、上限値より多い場合には樹脂組成物の粘度が高くなりすぎるためである。 The silver powder (C) used in the present invention is not particularly limited, but the average particle diameter is preferably 30 μm or less in order to prevent nozzle clogging during dispensing in which the resin composition is discharged using a nozzle. In order to maintain reliability, it is preferable that there are few ionic impurities, such as sodium and chlorine. If it is the silver powder currently marketed for electronic materials normally, reduced powder, atomized powder, etc. can be obtained, and as an average particle diameter, an average particle diameter is 1 micrometer or more and 30 micrometers or less. This is because the viscosity of the resin composition becomes too high below the lower limit, and can cause nozzle clogging during dispensing as described above above the upper limit, and silver powder other than for electronic materials may have a large amount of ionic impurities. Because there is, attention is necessary. The shape is not particularly limited, such as flaky shape or spherical shape, but preferably flaky shape is used, and it is usually contained in the resin composition in an amount of 70% by weight to 95% by weight. This is because when the proportion of silver powder is less than the lower limit, the conductivity deteriorates, and when it is higher than the upper limit, the viscosity of the resin composition becomes too high.
本発明で用いるスルフィド結合を有する化合物(D)は、スルフィド結合を有するものであれば、その種類については特に限定されるものではない。
化合物(D)を使用する第1の理由は良好な接着特性を得るためである。硫黄を含有する化合物が金属との密着を向上させることはよく知られているが、なかでもスルフィド結合を有する化合物(D)をラジカル重合可能な官能基を有する化合物(A)、重合開始剤(B)、銀粉(C)と同時に使用することで良好な接着性を有する樹脂組成物を得ることが可能となる。特にスルフィド結合とアルコキシシラン基を有する化合物を用いた場合に接着性向上効果が著しい。硫黄とアルコキシシラン基を有する化合物として3−メルカプトプロピルトリメトキシシランが一般的だが、ラジカル重合可能な官能基を有する化合物(A)と同時に用いた場合には反応が室温でも進行する。特に化合物(A)として(メタ)アクリロイル基を有する化合物を用いた場合には、室温でも10分以下で流動しなくなる場合もある。そこで本発明では活性水素基を有しない化合物(D)を使用する。このような化合物としてはビス(トリメトキシシリルプロピル)テトラスルフィド、ビス(トリエトキシシリルプロピル)テトラスルフィド、ビス(トリブトキシシリルプロピル)テトラスルフィド、ビス(ジメトキシメチルシリルプロピル)テトラスルフィド、ビス(ジエトキシメチルシリルプロピル)テトラスルフィド、ビス(ジブトキシメチルシリルプロピル)テトラスルフィド、ビス(トリメトキシシリルプロピル)ジスルフィド、ビス(トリエトキシシリルプロピル)ジスルフィド、ビス(トリブトキシシリルプロピル)ジスルフィド、ビス(ジメトキシメチルシリルプロピル)ジスルフィド、ビス(ジエトキシメチルシリルプロピル)ジスルフィド、ビス(ジブトキシメチルシリルプロピル)ジスルフィドなどが挙げられる。グリシジル基を有するシランカップリング剤との併用も好ましい。
The compound (D) having a sulfide bond used in the present invention is not particularly limited as long as it has a sulfide bond.
The first reason for using compound (D) is to obtain good adhesive properties. It is well known that a sulfur-containing compound improves adhesion to a metal. Among them, a compound (A) having a functional group capable of radical polymerization of a compound (D) having a sulfide bond, a polymerization initiator ( It becomes possible to obtain the resin composition which has favorable adhesiveness by using it simultaneously with B) and silver powder (C). In particular, when a compound having a sulfide bond and an alkoxysilane group is used, the effect of improving adhesiveness is remarkable. As a compound having sulfur and an alkoxysilane group, 3-mercaptopropyltrimethoxysilane is generally used, but when it is used simultaneously with the compound (A) having a radical polymerizable functional group, the reaction proceeds even at room temperature. In particular, when a compound having a (meth) acryloyl group is used as the compound (A), it may not flow in 10 minutes or less even at room temperature. Therefore, the compound (D) having no active hydrogen group is used in the present invention. Such compounds include bis (trimethoxysilylpropyl) tetrasulfide, bis (triethoxysilylpropyl) tetrasulfide, bis (tributoxysilylpropyl) tetrasulfide, bis (dimethoxymethylsilylpropyl) tetrasulfide, bis (diethoxy Methylsilylpropyl) tetrasulfide, bis (dibutoxymethylsilylpropyl) tetrasulfide, bis (trimethoxysilylpropyl) disulfide, bis (triethoxysilylpropyl) disulfide, bis (tributoxysilylpropyl) disulfide, bis (dimethoxymethylsilyl) Propyl) disulfide, bis (diethoxymethylsilylpropyl) disulfide, bis (dibutoxymethylsilylpropyl) disulfide and the like. A combined use with a silane coupling agent having a glycidyl group is also preferred.
化合物(D)を使用する第2の理由は硬化反応時に銀粉と反応することで樹脂組成物と支持体との接着力向上のみならず樹脂組成物自体の凝集力を向上させる点である。図1、2に化合物(D)の一例としてA−1289(日本ユニカー(株)製、ビス(トリエトキシシリルプロピル)テトラスルフィド)単独のDSC曲線、及びA−1289と銀粉を重量比1対1で混合したサンプルのDSC曲線を示す。測定条件はサンプル重量約30mg、昇温は室温から10℃/分で行った。図1には明確なピークは見られないが、図2では60℃付近から発熱が観察され始め、ピーク温度が約100℃、反応の終了は約130℃と非常にブロードな発熱ピークが観察される。この発熱ピークは銀粉とA−1289が同時に存在する時に始めて観察されることから銀粉とA−1289の反応と考えられる。
このように化合物(D)は銀粉表面と反応すること、しかも60℃付近から非常に緩やかに反応し始めることが確認できた。この点が非常に重要であり、室温以下で保存している間には化合物(D)は銀粉表面と反応せず硬化反応中に反応し始めるため、化合物(D)は硬化反応時に支持体表面及び銀粉表面の両方に作用することが可能であることを示している。この結果、支持体との接着力向上と同時に銀粉−樹脂間の結合が強固になるため樹脂硬化物の凝集力を向上させることが可能となる。
The second reason for using the compound (D) is to improve not only the adhesion between the resin composition and the support but also the cohesion of the resin composition itself by reacting with the silver powder during the curing reaction. As an example of the compound (D) in FIGS. 1 and 2, a DSC curve of A-1289 (manufactured by Nippon Unicar Co., Ltd., bis (triethoxysilylpropyl) tetrasulfide) alone, and A-1289 and silver powder in a weight ratio of 1: 1. The DSC curve of the sample mixed by is shown. The measurement conditions were a sample weight of about 30 mg, and the temperature was raised from room temperature to 10 ° C./min. Although no clear peak is observed in FIG. 1, in FIG. 2, an exotherm begins to be observed at around 60 ° C., a very broad exothermic peak is observed at about 100 ° C. and the end of the reaction is about 130 ° C. The Since this exothermic peak is first observed when silver powder and A-1289 are present at the same time, it is considered to be a reaction between silver powder and A-1289.
Thus, it has been confirmed that the compound (D) reacts with the surface of the silver powder and starts to react very slowly from around 60 ° C. This point is very important. Since the compound (D) does not react with the silver powder surface during storage at room temperature or lower and starts to react during the curing reaction, the compound (D) is supported on the surface of the support during the curing reaction. And that it can act on both the silver powder surface. As a result, since the bond between the silver powder and the resin becomes strong at the same time as improving the adhesive strength with the support, it is possible to improve the cohesive strength of the cured resin.
化合物(D)を使用する第3の理由は、良好な保存性である。重合開始剤(B)として有機過酸化物を使用した場合、保存中でも分解は進行しており特に分解温度の低い重合開始剤の場合には分解により発生したラジカルが化合物(A)の反応を引き起こし粘度上昇が顕著になる。通常ハイドロキノン等の禁止剤を添加することで粘度上昇を抑えるが、禁止剤を多量に配合すると硬化性の悪化が著しくなる場合、硬化物特性に悪影響を及ぼす場合がある。ここでスルフィド結合は発生したラジカルをトラップすることが可能なので禁止剤として働き粘度上昇を抑制することが可能であると共に、硬化開始温度の上昇は見られるが汎用の禁止剤ほどの悪影響はない。なかでも硬化物特性への悪化は見られないので好適に使用することが可能である。
このようにラジカル重合可能な官能基を有する化合物(A)、重合開始剤(B)、銀粉(C)及びスルフィド結合を有する化合物(D)を用いることで、低温硬化性に優れながらも保存性がよく、良好な密着性、低応力性を示す樹脂組成物を得ることが可能となった。
The third reason for using the compound (D) is good storage stability. When an organic peroxide is used as the polymerization initiator (B), decomposition proceeds even during storage, and in the case of a polymerization initiator having a low decomposition temperature, radicals generated by decomposition cause the reaction of the compound (A). The increase in viscosity becomes significant. In general, an inhibitor such as hydroquinone is added to suppress the increase in viscosity. However, when a large amount of the inhibitor is added, if the curability is remarkably deteriorated, the properties of the cured product may be adversely affected. Here, since the sulfide bond can trap the generated radical, it acts as an inhibitor and can suppress an increase in viscosity, and an increase in the curing start temperature can be seen, but it is not as bad as a general-purpose inhibitor. In particular, since the deterioration of the cured product properties is not observed, it can be used preferably.
Thus, by using the compound (A) having a functional group capable of radical polymerization, the polymerization initiator (B), the silver powder (C) and the compound (D) having a sulfide bond, the low-temperature curability is excellent, but the storage stability is high. Thus, it became possible to obtain a resin composition exhibiting good adhesion and low stress.
本発明では希釈剤を使用することが可能である。なかでも以下に示すような化合物は良好な接着性を得るために好適に使用される。2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、3−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、3−ヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート、1,2−シクロヘキサンジオールモノ(メタ)アクリレート、1,3−シクロヘキサンジオールモノ(メタ)アクリレート、1,4−シクロヘキサンジオールモノ(メタ)アクリレート、1,2−シクロヘキサンジメタノールモノ(メタ)アクリレート、1,3−シクロヘキサンジメタノールモノ(メタ)アクリレート、1,4−シクロヘキサンジメタノールモノ(メタ)アクリレート、1,2−シクロヘキサンジエタノールモノ(メタ)アクリレート、1,3−シクロヘキサンジエタノールモノ(メタ)アクリレート、1,4−シクロヘキサンジエタノールモノ(メタ)アクリレート、グリセリンモノ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、トリメチロールプロパンモノ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、ペンタエリスリトールモノ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ネオペンチルグリコールモノ(メタ)アクリレートといった水酸基を有する(メタ)アクリレート化合物。水酸基を有する(メタ)アクリレート化合物とジカルボン酸を反応することでられたカルボキシ基を有する(メタ)アクリレート化合物。ここで使用可能なジカルボン酸としては、例えばしゅう酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、マレイン酸、フマル酸、フタル酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸及びこれらの誘導体が挙げられ、なかでもこれらジカルボン酸を脱水した酸無水物は水酸基と容易に反応しハーフエステル化物を得ることができるので好適に用いられる。水酸基を有する(メタ)アクリレート化合物及びカルボキシ基を有する(メタ)アクリレート化合物はどちらか一方でも併用しても差し支えなく、それぞれ複数種を使用しても差し支えない。 In the present invention, a diluent can be used. Of these, the following compounds are preferably used for obtaining good adhesion. 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl ( (Meth) acrylate, 1,2-cyclohexanediol mono (meth) acrylate, 1,3-cyclohexanediol mono (meth) acrylate, 1,4-cyclohexanediol mono (meth) acrylate, 1,2-cyclohexanedimethanol mono (meta) ) Acrylate, 1,3-cyclohexanedimethanol mono (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, 1,2-cyclohexanediethanol mono (meth) acrylate, 1 3-cyclohexanediethanol mono (meth) acrylate, 1,4-cyclohexanediethanol mono (meth) acrylate, glycerin mono (meth) acrylate, glycerin di (meth) acrylate, trimethylolpropane mono (meth) acrylate, trimethylolpropane di ( (Meth) acrylate compounds having a hydroxyl group such as (meth) acrylate, pentaerythritol mono (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, and neopentyl glycol mono (meth) acrylate. A (meth) acrylate compound having a carboxy group obtained by reacting a (meth) acrylate compound having a hydroxyl group with a dicarboxylic acid. Examples of the dicarboxylic acid usable here include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid, and tetrahydrophthalic acid. Hexahydrophthalic acid and derivatives thereof. Among them, an acid anhydride obtained by dehydrating these dicarboxylic acids is preferably used because it can easily react with a hydroxyl group to obtain a half-esterified product. Either a (meth) acrylate compound having a hydroxyl group or a (meth) acrylate compound having a carboxy group may be used in combination, or a plurality of types may be used.
上記以外にも水酸基及びカルボキシ基を有しない(メタ)アクリレート化合物又はビニル基を有する化合物を使用することも可能である。例えば下記のような化合物である。メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、ターシャルブチル(メタ)アクリレート、イソデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、トリデシル(メタ)アクリレート、セチル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソアミル(メタ)アクリレート、イソステアリル(メタ)アクリレート、ベヘニル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、その他のアルキル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ターシャルブチルシクロヘキシル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、グリシジル(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジンクモノ(メタ)アクリレート、ジンクジ(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、ネオペンチルグリコール(メタ)アクリレート、トリフロロエチル(メタ)アクリレート、2,2,3,3−テトラフロロプロピル(メタ)アクリレート、2,2,3,3,4,4−ヘキサフロロブチル(メタ)アクリレート、パーフロロオクチル(メタ)アクリレート、パーフロロオクチルエチル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、1,9−ノナンジオールジ(メタ)アクリレート、1,3−ブタンジオールジ(メタ)アクリレート、1,10−デカンジオールジ(メタ)アクリレート、テトラメチレングリコールジ(メタ)アクリレート、メトキシエチル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、エトキシジエチレングリコール(メタ)アクリレート、メトキシポリアルキレングリコールモノ(メタ)アクリレート、オクトキシポリアルキレングリコールモノ(メタ)アクリレート、ラウロキシポリアルキレングリコールモノ(メタ)アクリレート、ステアロキシポリアルキレングリコールモノ(メタ)アクリレート、アリロキシポリアルキレングリコールモノ(メタ)アクリレート、ノニルフェノキシポリアルキレングリコールモノ(メタ)アクリレート、N,N’−メチレンビス(メタ)アクリルアミド、N,N’−エチレンビス(メタ)アクリルアミド、1,2−ジ(メタ)アクリルアミドエチレングリコール、ジ(メタ)アクリロイロキシメチルトリシクロデカン、N−(メタ)アクリロイロキシエチルマレイミド、N−(メタ)アクリロイロキシエチルヘキサヒドロフタルイミド、N−(メタ)アクリロイロキシエチルフタルイミド、n−ビニル−2−ピロリドン、スチレン誘導体、α−メチルスチレン誘導体。 In addition to the above, it is also possible to use a (meth) acrylate compound having no hydroxyl group or carboxy group or a compound having a vinyl group. For example, the following compounds. Methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tertiary butyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) Acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isoamyl (meth) acrylate, isostearyl (meth) acrylate, behenyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, other alkyl (meth) acrylates, cyclohexyl (Meth) acrylate, tertiary butyl cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (Meth) acrylate, isobornyl (meth) acrylate, glycidyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, zinc mono (meth) acrylate, zinc di (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) Acrylate, neopentyl glycol (meth) acrylate, trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2,2,3,3,4,4-hexafluorobutyl ( (Meth) acrylate, perfluorooctyl (meth) acrylate, perfluorooctylethyl (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4- Tandiol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,10-decanediol di ( (Meth) acrylate, tetramethylene glycol di (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxypolyalkylene glycol mono (meth) acrylate, octoxypolyalkylene glycol mono (Meth) acrylate, Lauroxy polyalkylene glycol mono (meth) acrylate, Stearoxy polyalkylene glycol mono (meth) acrylate, Allyloxy polyalkylene glycol Rumono (meth) acrylate, nonylphenoxypolyalkylene glycol mono (meth) acrylate, N, N'-methylenebis (meth) acrylamide, N, N'-ethylenebis (meth) acrylamide, 1,2-di (meth) acrylamide ethylene Glycol, di (meth) acryloyloxymethyltricyclodecane, N- (meth) acryloyloxyethyl maleimide, N- (meth) acryloyloxyethyl hexahydrophthalimide, N- (meth) acryloyloxyethyl phthalimide, n -Vinyl-2-pyrrolidone, styrene derivatives, α-methylstyrene derivatives.
本発明の樹脂組成物には、必要により、消泡剤、界面活性剤、各種重合禁止剤、酸化防止剤等の添加剤を用いることができる。
本発明の樹脂組成物は、例えば各成分を予備混合した後、3本ロールを用いて混練した後真空下脱泡することにより製造することができる。
In the resin composition of the present invention, additives such as an antifoaming agent, a surfactant, various polymerization inhibitors, and antioxidants can be used as necessary.
The resin composition of the present invention can be produced, for example, by premixing the components, kneading using three rolls, and degassing under vacuum.
本発明の樹脂組成物を用いて半導体装置を製作する方法は、公知の方法を用いることができる。例えば、市販のダイボンダーを用いて、リードフレームの所定の部位に樹脂組成物をディスペンス塗布した後、半導体素子をマウントし、加熱硬化する。その後、ワイヤーボンディングして、エポキシ樹脂を用いてトランスファー成形することによって半導体装置を製作する。又はフリップチップ接合後アンダーフィル材で封止したフリップチップBGAなどのチップ裏面に樹脂組成物をディスペンスしヒートスプレッダー、リッドといった放熱部品を搭載し加熱硬化するなどといった使用方法も可能である。
以下実施例を用いて本発明を具体的に説明するが、これらに限定されるものではない。配合割合は重量部で示す。
As a method of manufacturing a semiconductor device using the resin composition of the present invention, a known method can be used. For example, using a commercially available die bonder, the resin composition is dispensed on a predetermined portion of the lead frame, and then the semiconductor element is mounted and heat-cured. Then, a semiconductor device is manufactured by wire bonding and transfer molding using an epoxy resin. Alternatively, it is possible to use a method in which a resin composition is dispensed on the back side of a chip such as a flip chip BGA sealed with an underfill material after flip chip bonding, and a heat dissipating component such as a heat spreader or lid is mounted and cured.
EXAMPLES The present invention will be specifically described below using examples, but is not limited thereto. The blending ratio is expressed in parts by weight.
[実施例1]
化合物(A)としてポリテトラメチレングリコールとイソホロンジイソシアネートと2−ヒドロキシメチルメタクリレートとの反応により得られたウレタンジメタクリレート化合物(分子量約1600、以下化合物A1)を、重合開始剤(B)としてジクミルパーオキサイド(日本油脂(株)製、パークミルD、急速加熱試験における分解温度:126℃、以下重合開始剤1)及びジ(4−t−ブチルシクロヘキシル)パーオキシジカーボネート(日本油脂(株)製、パーロイルTCP、急速加熱試験における分解温度:82℃、以下重合開始剤2)を、銀粉(C)として平均粒径8μm、最大粒径30μmのフレーク状銀粉(以下銀粉)を、化合物(D)としてテトラスルフィド結合及びエトキシシラン基を有する化合物(日本ユニカー(株)製、A−1289、以下化合物D)を、1,4−シクロヘキサンジメタノールモノアクリレート(日本化成(株)製、CHDMMA、以下化合物Y1)、2−メタクリロイルオキシエチルコハク酸(共栄社化学(株)製、ライトエステルHO−MS、以下化合物Y2)、1,6−ヘキサンジオールジメタクリレート(共栄社化学(株)製、ライトエステル1、6HX、以下化合物Y3)、グリシジル基を有するカップリング剤(信越化学工業(株)製、KBM−403E、以下化合物Z1)を表1のように配合し、3本ロールを用いて混練し、脱泡することで樹脂組成物を得た。配合割合は重量部である。得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
[Example 1]
A urethane dimethacrylate compound (molecular weight of about 1600, hereinafter referred to as compound A1) obtained by reaction of polytetramethylene glycol, isophorone diisocyanate and 2-hydroxymethyl methacrylate as compound (A) is used as dicumyl parper as polymerization initiator (B). Oxide (Nippon Yushi Co., Ltd., Park Mill D, decomposition temperature in rapid heating test: 126 ° C., hereinafter referred to as polymerization initiator 1) and di (4-t-butylcyclohexyl) peroxydicarbonate (Nippon Yushi Co., Ltd., Parroyl TCP, decomposition temperature in rapid heating test: 82 ° C., polymerization initiator 2) as silver powder (C), flaky silver powder (hereinafter referred to as silver powder) having an average particle diameter of 8 μm and maximum particle diameter of 30 μm as compound (D) A compound having a tetrasulfide bond and an ethoxysilane group (Nihon Unicar Co., Ltd. A-1289, hereinafter referred to as compound D), 1,4-cyclohexanedimethanol monoacrylate (manufactured by Nippon Kasei Co., Ltd., CHDMMA, hereinafter referred to as compound Y1), 2-methacryloyloxyethyl succinic acid (Kyoeisha Chemical Co., Ltd.) , Light ester HO-MS, hereinafter referred to as compound Y2), 1,6-hexanediol dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., light ester 1, 6HX, hereinafter referred to as compound Y3), coupling agent having a glycidyl group (Shin-Etsu Chemical) Industrial Co., Ltd. KBM-403E, hereinafter referred to as Compound Z1) was blended as shown in Table 1, kneaded using three rolls, and defoamed to obtain a resin composition. The blending ratio is parts by weight. The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.
[実施例2〜5]
化合物(A)として以下の化合物を使用した。
ポリテトラメチレングリコールとマレイミド化酢酸の反応により得られたビスマレイミド化合物(分子量580、以下化合物A2)
シクロヘキサンジカルボン酸のジアリルエステルとポリプロピレングリコールとの反応により得られたジアリルエステル化合物(分子量1000、ただし原料として用いたシクロヘキサンジカルボン酸のジアリルエステルを約15%含む、以下化合物A3)
1,4−シクロヘキサンジメタノール/1,6−ヘキサンジオール(=3/1(重量比))と炭酸ジメチルの反応により得られたポリカーボネートジオールとメチルメタクリレートの反応により得られたポリカーボネートジメタクリレート化合物(分子量1000、以下化合物A4)
酸価108mgKOH/gで分子量4600のアクリルオリゴマーと2−ヒドロキシメタクリレート/ブチルアルコール(=1/2(モル比))との反応により得られたメタクリル化アクリルオリゴマー(分子量5000、以下化合物A5)
表1のように配合し、実施例1と同様に3本ロールを用いて混練し、脱泡することで樹脂組成物を得た。配合割合は重量部である。得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
[Examples 2 to 5]
The following compounds were used as the compound (A).
Bismaleimide compound obtained by reaction of polytetramethylene glycol and maleimidated acetic acid (molecular weight 580, hereinafter referred to as compound A2)
Diallyl ester compound obtained by reaction of diallyl ester of cyclohexanedicarboxylic acid and polypropylene glycol (molecular weight 1000, but containing about 15% of diallyl ester of cyclohexanedicarboxylic acid used as a raw material, hereinafter compound A3)
1,4-cyclohexanedimethanol / 1,6-hexanediol (= 3/1 (weight ratio)) and polycarbonate dimethacrylate compound (molecular weight) obtained by reaction of polycarbonate diol and methyl methacrylate obtained by reaction of dimethyl carbonate 1000, hereinafter Compound A4)
Methacrylated acrylic oligomer (
The resin composition was obtained by mixing | blending like Table 1, kneading using a 3 roll similarly to Example 1, and defoaming. The blending ratio is parts by weight. The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.
[比較例1〜4]
表1に示す割合で配合し実施例1と同様に樹脂組成物を得た。
なお比較例3ではメルカプト基とアルコキシシラン基を有する化合物として3-メルカプトプロピルトリメトキシシラン(信越化学工業(株)製、KBM−803P、以下化合物Z2)を用いた。
得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
[Comparative Examples 1-4]
The resin composition was obtained in the same manner as in Example 1 by blending at the ratio shown in Table 1.
In Comparative Example 3, 3-mercaptopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., KBM-803P, hereinafter referred to as compound Z2) was used as the compound having a mercapto group and an alkoxysilane group.
The obtained resin composition was evaluated by the following methods. The evaluation results are shown in Table 1.
評価方法
・粘度及び保存性:E型粘度計(3°コーン)を用い25℃、2.5rpmでの値を樹脂組成物作製後(初期)及び25℃48時間処理後に測定した。粘度が15〜25Pa・s、粘度の変化率が20%以下の場合を合格とした。粘度の単位はPa・sである。
・接着強度:表1に示す樹脂組成物を用いて6×6mmのシリコンチップをNi−Pd/Auめっきした銅フレームにマウントし、120℃オーブン中60分硬化した。硬化後及び吸湿処理(85℃、85%、72時間)後に自動接着力測定装置を用い260℃での熱時ダイシェア強度を測定した。260℃熱時ダイシェア強度が30N/チップ以上の場合を合格とした。接着強度の単位はN/チップである。
・弾性率:表1に示す樹脂組成物を用いて4×20×0.1mmのフィルム状の試験片を作製し(硬化条件120℃60分)、動的粘弾性測定機(DMA)にて引っ張りモードでの測定を行った。測定条件は以下の通りである。
測定温度:−100〜300℃
昇温速度:5℃/分
周波数:10Hz
荷重:100mN
25℃における貯蔵弾性率を弾性率とし5000MPa以下の場合を合格とした。弾性率の単位はMPaである。
・耐リフロー性:表1に示す樹脂組成物を用いて、下記のリードフレームとシリコンチップをオーブン中120℃60分間硬化し接着した。封止材料(スミコンEME−7026、住友ベークライト(株)製)を用い封止し、パッケージを作製した。このパッケージを30℃、相対湿度60%、168時間吸湿処理した後、IRリフロー処理(260℃、10秒、3回リフロー)を行った。処理後のパッケージを超音波探傷装置(透過型)により剥離の程度を測定した。ダイアタッチ部の剥離面積が10%未満の場合を合格とした。剥離面積の単位は%である。
パッケージ:QFP(14×20×2.0mm)
リードフレーム:Ni−Pd/Auめっきした銅フレーム
チップサイズ:6×6mm
Evaluation method / Viscosity and storage stability: Using an E-type viscometer (3 ° cone), values at 25 ° C. and 2.5 rpm were measured after the resin composition was prepared (initial) and after treatment at 25 ° C. for 48 hours. The case where the viscosity was 15 to 25 Pa · s and the change rate of the viscosity was 20% or less was regarded as acceptable. The unit of viscosity is Pa · s.
Adhesive strength: A 6 × 6 mm silicon chip was mounted on a Ni—Pd / Au plated copper frame using the resin composition shown in Table 1, and cured in a 120 ° C. oven for 60 minutes. After curing and after moisture absorption treatment (85 ° C., 85%, 72 hours), the hot die shear strength at 260 ° C. was measured using an automatic adhesive force measuring apparatus. The case where the die shear strength when heated at 260 ° C. was 30 N / chip or more was regarded as acceptable. The unit of adhesive strength is N / chip.
Elastic modulus: 4 × 20 × 0.1 mm film-like test pieces were prepared using the resin composition shown in Table 1 (curing conditions: 120 ° C. for 60 minutes), and using a dynamic viscoelasticity measuring machine (DMA) Measurements were made in pull mode. The measurement conditions are as follows.
Measurement temperature: -100 to 300 ° C
Temperature increase rate: 5 ° C / min Frequency: 10Hz
Load: 100mN
The storage elastic modulus at 25 ° C. was regarded as the elastic modulus, and the case of 5000 MPa or less was regarded as acceptable. The unit of elastic modulus is MPa.
Reflow resistance: Using the resin composition shown in Table 1, the following lead frame and silicon chip were cured and bonded in an oven at 120 ° C. for 60 minutes. Sealing material (Sumicon EME-7026, manufactured by Sumitomo Bakelite Co., Ltd.) was used for sealing to produce a package. This package was subjected to a moisture absorption treatment at 30 ° C. and a relative humidity of 60% for 168 hours, followed by an IR reflow treatment (260 ° C., 10 seconds, 3 times reflow). The degree of peeling of the treated package was measured with an ultrasonic flaw detector (transmission type). The case where the peeling area of the die attach part was less than 10% was regarded as acceptable. The unit of the peeled area is%.
Package: QFP (14 x 20 x 2.0 mm)
Lead frame: Ni-Pd / Au plated copper frame Chip size: 6 x 6 mm
本発明の樹脂組成物は、良好な低温硬化性及び保存性を有しかつ高接着性で応力緩和特性にも優れるため、ダイアタッチペースト又は放熱部材接着用材料として使用した場合、半導体素子のダメージが少なくまた得られた半導体装置は耐リフロー性に優れており、その結果高信頼性の半導体装置を得ることができる。 The resin composition of the present invention has good low-temperature curability and storage stability, and has high adhesiveness and excellent stress relaxation characteristics. Therefore, when used as a die attach paste or a material for adhering heat dissipation members, damage to semiconductor elements The obtained semiconductor device is excellent in reflow resistance, and as a result, a highly reliable semiconductor device can be obtained.
Claims (8)
A semiconductor device produced by using the resin composition according to claim 1 as a die attach paste for a semiconductor or a material for adhering a heat dissipation member.
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