WO2022202505A1 - Electrically conductive resin composition, material having high thermal conductivity, and semiconductor device - Google Patents
Electrically conductive resin composition, material having high thermal conductivity, and semiconductor device Download PDFInfo
- Publication number
- WO2022202505A1 WO2022202505A1 PCT/JP2022/011708 JP2022011708W WO2022202505A1 WO 2022202505 A1 WO2022202505 A1 WO 2022202505A1 JP 2022011708 W JP2022011708 W JP 2022011708W WO 2022202505 A1 WO2022202505 A1 WO 2022202505A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- resin composition
- silver
- conductive resin
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 69
- 239000004065 semiconductor Substances 0.000 title claims description 48
- 239000000463 material Substances 0.000 title claims description 24
- 239000002245 particle Substances 0.000 claims abstract description 116
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 109
- 229910052709 silver Inorganic materials 0.000 claims abstract description 108
- 239000004332 silver Substances 0.000 claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- -1 acrylic compound Chemical class 0.000 claims abstract description 54
- 239000004593 Epoxy Substances 0.000 claims abstract description 24
- 125000000962 organic group Chemical group 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000012790 adhesive layer Substances 0.000 claims description 14
- 238000005245 sintering Methods 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000004020 conductor Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 110
- 229920005989 resin Polymers 0.000 description 55
- 239000011347 resin Substances 0.000 description 55
- 238000001723 curing Methods 0.000 description 33
- 125000004122 cyclic group Chemical group 0.000 description 25
- 239000000047 product Substances 0.000 description 21
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 14
- 239000005011 phenolic resin Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 229920001568 phenolic resin Polymers 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 239000004925 Acrylic resin Substances 0.000 description 7
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920002050 silicone resin Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000011231 conductive filler Substances 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000003574 free electron Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000003827 glycol group Chemical group 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
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- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 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 2
- 150000003512 tertiary amines Chemical class 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
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-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
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- RUJPNZNXGCHGID-UHFFFAOYSA-N (Z)-beta-Terpineol Natural products CC(=C)C1CCC(C)(O)CC1 RUJPNZNXGCHGID-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
- CTPYJEXTTINDEM-UHFFFAOYSA-N 1,2-bis(1-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOCC(C)C1=CC=CC=C1C(C)COOC(C)(C)C CTPYJEXTTINDEM-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
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- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
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- LORVPHHKJFSORQ-UHFFFAOYSA-N 1-[1-(1-butoxypropan-2-yloxy)propan-2-yloxy]propan-2-ol Chemical compound CCCCOCC(C)OCC(C)OCC(C)O LORVPHHKJFSORQ-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000008569 process Effects 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
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/22—Di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/40—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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
Definitions
- the present invention relates to a conductive resin composition, a highly thermally conductive material and a semiconductor device.
- Patent Document 1 discloses a conductive filler made of silver powder having a predetermined average particle size, an epoxy resin, a reactive diluent having one or more glycidyl functional groups in an aliphatic hydrocarbon chain, and a thermally conductive filler containing a curing agent.
- a conductive adhesive composition is disclosed. The document exemplifies cyclohexanedimethanol diglycidyl ether, neopentyl glycol diglycidyl ether, and the like as the reactive diluent.
- Patent Document 2 discloses a composition containing a predetermined glycidyl ether compound, a predetermined phenolic resin curing agent, a curing accelerator, and a conductive filler, wherein a predetermined amount of the phenolic resin curing agent is added to the glycidyl ether compound.
- a conductive adhesive is disclosed comprising: This document exemplifies 1,4-cyclohexanedimethanol diglycidyl ether and pentaerythritol tetraglycidyl ether as the glycidyl ether compound.
- Patent Document 3 discloses a thermally conductive conductive adhesive composition containing a conductive filler, an epoxy resin, a reactive diluent having two or more glycidyl ether functional groups in an aliphatic hydrocarbon chain, and a curing agent. things are disclosed. The document exemplifies cyclohexanedimethanol diglycidyl ether, neopentyl glycol diglycidyl ether, and the like as the reactive diluent.
- Patent Documents 1 to 3 have room for improvement in thermal conductivity, product reliability, and adhesion to substrates.
- the present inventors have found that the above problems can be solved by using a combination of a (meth)acrylic compound and a specific polyfunctional epoxy compound, and have completed the present invention. That is, the present invention can be shown below.
- a conductive resin composition is provided.
- R represents a hydroxyl group or an alkyl group having 1 to 3 carbon atoms, and multiple Rs may be the same or different.
- Q represents a divalent to hexavalent organic group.
- X represents an alkylene group having 1 to 3 carbon atoms, and multiple X's may be the same or different.
- m is an integer of 0-2, n is an integer of 2-4.
- a high thermal conductivity material obtained by sintering the conductive resin composition is provided.
- a substrate A semiconductor element mounted on the base material via an adhesive layer, A semiconductor device is provided in which the adhesive layer is formed by sintering the conductive resin composition.
- the conductive resin composition of the present invention promotes sintering of the silver-containing particles by curing shrinkage to obtain a highly thermally conductive material with excellent thermal conductivity. It is possible to obtain a highly thermally conductive material with excellent product reliability because it also has excellent adhesion to. In other words, it is possible to provide a conductive resin composition having an excellent balance of these properties.
- FIG. 1 is a cross-sectional view schematically showing an example of a semiconductor device
- FIG. 1 is a cross-sectional view schematically showing an example of a semiconductor device
- FIG. 1 is a cross-sectional view schematically showing an example of a semiconductor device
- alkyl group includes not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups).
- (meth)acryl used herein represents a concept that includes both acryl and methacryl. The same applies to similar expressions such as "(meth)acrylate” and "(meth)acryloyl”.
- the conductive resin composition of the present embodiment is (A) silver-containing particles; (B) a (meth) acrylic compound; (C) at least one polyfunctional epoxy compound selected from compounds represented by the following general formula (1).
- the sintering of the silver-containing particles is promoted by curing shrinkage, and a high thermal conductivity material with excellent thermal conductivity is obtained.
- the elastic modulus is low, the stress is relaxed, and the adhesiveness to the substrate etc. is excellent. Therefore, a high thermal conductivity material with excellent product reliability can be obtained.
- thermal conductivity can be evaluated by volume resistivity according to the Wiedemann-Franz law. In other words, the volume resistivity is the electrical resistance value per unit volume. If the electrical resistance value is low, the free electrons become carriers and electricity easily passes through. .
- the silver-containing particles (A) can be sintered by an appropriate heat treatment to form a particle connecting structure (sintering structure).
- the inclusion of silver-containing particles in the conductive resin composition particularly the inclusion of silver particles having a relatively small particle size and a relatively large specific surface area, allows A sintered structure is likely to be formed even by heat treatment.
- a preferred particle size will be described later.
- the shape of the silver-containing particles is not particularly limited, and includes known shapes such as spherical, dendritic, string-like, scale-like, agglomerated, and polyhedral shapes. can include one or more, preferably two or more. Thereby, it is excellent by electroconductivity.
- spherical silver-containing particles (a1) and scaly, aggregated, and one or more kinds of silver-containing particles (a2) selected from polyhedral shapes, more preferably containing spherical silver-containing particles (a1) and scale-like silver-containing particles (a2-1) is particularly preferred.
- the contact ratio between the silver-containing particles is further improved, so that a network is easily formed after sintering the conductive resin composition, and the thermal conductivity and the electrical conductivity are further improved.
- the term “spherical” is not limited to a perfect sphere, and includes a shape with some irregularities on the surface. Its circularity is, for example, 0.90 or more, preferably 0.92 or more, and more preferably 0.94 or more.
- the surface of the silver-containing particles (A) is treated with an organic compound such as a carboxylic acid, a saturated fatty acid having 4 to 30 carbon atoms, a monovalent unsaturated fatty acid having 4 to 30 carbon atoms, or a long-chain alkylnitrile. good too.
- an organic compound such as a carboxylic acid, a saturated fatty acid having 4 to 30 carbon atoms, a monovalent unsaturated fatty acid having 4 to 30 carbon atoms, or a long-chain alkylnitrile. good too.
- the silver-containing particles (A) may be (i) particles consisting essentially of silver, or (ii) particles consisting of silver and a component other than silver. Moreover, (i) and (ii) may be used together as the metal-containing particles.
- the silver-containing particles (A) particularly preferably contain silver-coated resin particles in which the surfaces of resin particles are coated with silver. Thereby, it is possible to prepare a conductive resin composition that gives a cured product having excellent thermal conductivity and a low storage elastic modulus.
- the silver-coated resin particles have silver on the surface and a resin inside, they are considered to have good thermal conductivity and to be softer than particles made only of silver. Therefore, it is considered that the use of silver-coated resin particles facilitates designing appropriate values for thermal conductivity and storage elastic modulus.
- the thermal conductivity it is considered to increase the amount of silver-containing particles.
- metals are generally "hard", too much silver-containing particles may result in too high a modulus after sintering.
- Part or all of the silver-containing particles are silver-coated resin particles, making it possible to easily design a conductive resin composition from which a cured product having desired thermal conductivity and storage elastic modulus can be obtained.
- the silver-coated resin particles it is sufficient that at least a part of the surface of the resin particles is covered with a silver layer. Of course, the entire surface of the resin particles may be covered with silver.
- the silver layer preferably covers 50% or more, more preferably 75% or more, and still more preferably 90% or more of the surface of the resin particles.
- the silver layer covers substantially the entire surface of the resin particles. From another point of view, when the silver-coated resin particles are cut along a certain cross section, it is preferable that the silver layer is observed all around the cross section.
- the mass ratio of resin/silver in the silver-coated resin particles is, for example, 90/10 to 10/90, preferably 80/20 to 20/80, more preferably 70/30 to 30/70. be.
- the "resin" in the silver-coated resin particles examples include silicone resins, (meth)acrylic resins, phenol resins, polystyrene resins, melamine resins, polyamide resins, polytetrafluoroethylene resins, and the like. Of course, resins other than these may be used. Moreover, only one resin may be used, or two or more resins may be used in combination. From the viewpoint of elastic properties and heat resistance, the resin is preferably a silicone resin or a (meth)acrylic resin.
- the silicone resin may be particles composed of organopolysiloxane obtained by polymerizing organochlorosilanes such as methylchlorosilane, trimethyltrichlorosilane, and dimethyldichlorosilane.
- organochlorosilanes such as methylchlorosilane, trimethyltrichlorosilane, and dimethyldichlorosilane.
- a silicone resin having a basic skeleton structure obtained by further three-dimensionally cross-linking an organopolysiloxane may be used.
- the (meth)acrylic resin is a resin obtained by polymerizing a monomer containing (meth)acrylic acid ester as a main component (50% by weight or more, preferably 70% by weight or more, more preferably 90% by weight or more). be able to.
- (Meth)acrylic acid esters for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate , stearyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-propyl (meth)acrylate, chloro-2-hydroxyethyl (meth)acrylate, diethylene glycol mono (meth)acrylate, At least one compound selected from the group consisting of methoxyethyl (meth)acrylate, glycidyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate and isoboronol (meth)acrylate can be mentioned.
- the monomer component of the acrylic resin may contain a small amount of other monomers.
- Such other monomer components include, for example, styrenic monomers.
- silver-coated (meth)acrylic resin see also the description in JP-A-2017-126463.
- Suitable functional groups may be introduced into silicone resins and (meth)acrylic resins.
- Functional groups that can be introduced are not particularly limited. Examples thereof include epoxy group, amino group, methoxy group, phenyl group, carboxyl group, hydroxyl group, alkyl group, vinyl group and mercapto group.
- the resin particle portion of the silver-coated resin particles may contain various additive components, such as low-stress modifiers.
- low-stress modifiers include liquid synthetic rubbers such as butadiene styrene rubber, butadiene acrylonitrile rubber, polyurethane rubber, polyisoprene rubber, acrylic rubber, fluororubber, liquid organopolysiloxane, and liquid polybutadiene.
- liquid synthetic rubbers such as butadiene styrene rubber, butadiene acrylonitrile rubber, polyurethane rubber, polyisoprene rubber, acrylic rubber, fluororubber, liquid organopolysiloxane, and liquid polybutadiene.
- the resin particle portion contains a silicone resin
- the inclusion of a low-stress modifier can make the elastic properties of the silver-coated resin particles preferable.
- the shape of the resin particle portion of the silver-coated resin particles is not particularly limited. A combination of a spherical shape and an irregular shape other than a spherical shape, such as a flat shape, a plate shape, a needle shape, etc., is preferable.
- the specific gravity of the silver-coated resin particles is not particularly limited, the lower limit is, for example, 2 or more, preferably 2.5 or more, and more preferably 3 or more. Further, the upper limit of the specific gravity is, for example, 10 or less, preferably 9 or less, more preferably 8 or less. Appropriate specific gravity is preferable in terms of dispersibility of the silver-coated resin particles themselves and uniformity when silver-coated resin particles and other silver-containing particles are used in combination.
- the proportion of silver-coated resin particles in the total silver-containing particles (A) is preferably 1 to 50% by mass, more preferably 3 to 45% by mass, and still more preferably 5 to 40% by mass. is. By appropriately adjusting this ratio, it is possible to further improve heat dissipation while suppressing a decrease in adhesive strength due to heat cycles.
- the silver-containing particles other than the silver-coated resin particles are, for example, particles consisting essentially of silver.
- the median diameter D50 of the silver-containing particles (A) is, for example, 0.01-50 ⁇ m, preferably 0.1-20 ⁇ m, more preferably 0.5-10 ⁇ m.
- D50 By setting D50 to an appropriate value, it is easy to balance thermal conductivity, sinterability, resistance to heat cycles, and the like. Also, by setting D50 to an appropriate value, it may be possible to improve the workability of application/adhesion.
- the particle size distribution (horizontal axis: particle size, vertical axis: frequency) of the silver-containing particles may be unimodal or multimodal.
- the silver-containing particles (A) contain spherical silver-containing particles (a1) and scale-like silver-containing particles (a2-1). These silver-containing particles are more preferably silver particles consisting essentially of silver.
- the median diameter D 50 of the spherical silver-containing particles (a1) is, for example, 0.1-20 ⁇ m, preferably 0.5-10 ⁇ m, more preferably 0.5-5.0 ⁇ m.
- the specific surface area of the spherical silver-containing particles (a1) is, for example, 0.1 to 2.5 m 2 /g, preferably 0.5 to 2.3 m 2 /g, more preferably 0.8 to 2.0 m 2 /g. is g.
- the tap density of the spherical silver-containing particles (a1) is, for example, 1.5 to 6.0 g/cm 3 , preferably 2.5 to 5.8 g/cm 3 , more preferably 4.5 to 5.5 g/cm 3 .
- the circularity of the spherical silver-containing particles (a1) is, for example, 0.90 or more, preferably 0.92 or more, and more preferably 0.94 or more. Satisfying each of these properties provides an excellent balance of thermal conductivity, sinterability, resistance to heat cycles, and the like.
- the median diameter D50 of the scale-like silver-containing particles (a2-1) is, for example, 0.1 to 20 ⁇ m, preferably 1.0 to 15 ⁇ m, more preferably 2.0 to 10 ⁇ m.
- the specific surface area of the scale-like silver-containing particles (a2-1) is, for example, 0.1 to 2.5 m 2 /g, preferably 0.2 to 2.0 m 2 /g, more preferably 0.25 to 1.0 m 2 /g. 2 m 2 /g.
- the tap density of the scale-like silver-containing particles (a2-1) is, for example, 1.5 to 6.0 g/cm 3 , preferably 2.5 to 5.9 g/cm 3 , more preferably 4.0 to 5.0 g/cm 3 . 8 g/cm 3 . Satisfying each of these properties provides an excellent balance of thermal conductivity, sinterability, resistance to heat cycles, and the like.
- the ratio (a1/a2-1) of the content of the spherical silver-containing particles (a1) to the content of the scale-like silver-containing particles (a2-1) is preferably 0.1 or more and 10 or less, more preferably 0.1. It can be 3 or more and 5 or less, particularly preferably 0.5 or more and 3 or less. As a result, the contact ratio between the silver-containing particles is particularly improved, so that a network is easily formed after sintering the paste-like polymerizable composition, and the thermal conductivity and the electrical conductivity are particularly improved.
- the ratio (a1/a2-1) of the median diameter D50 of the spherical silver-containing particles (a1) to the median diameter D50 of the scale-like silver-containing particles (a2-1) is preferably 0.01 or more and 0.8 or less. , more preferably 0.05 or more and 0.6 or less.
- the ratio (a1/a2-1) of the tap density of the spherical silver-containing particles (a1) to the tap density of the scale-like silver-containing particles (a2-1) is preferably 0.5 or more and 2.0 or less, more preferably It is 0.7 or more and 1.2 or less.
- the filling rate of the silver-containing particles is improved, and the contact ratio between the silver-containing particles is particularly improved.
- Conductivity is particularly improved.
- the median diameter D50 of the silver-coated resin particles is, for example, 5.0-25 ⁇ m, preferably 7.0-20 ⁇ m, more preferably 8.0-15 ⁇ m. Thereby, thermal conductivity can be improved more.
- the median diameter D 50 of the silver-containing particles (A) can be determined by, for example, particle image measurement using a flow type particle image analyzer FPIA (registered trademark)-3000 manufactured by Sysmex Corporation. More specifically, the particle diameter of the silver-containing particles (A) can be determined by measuring the volume-based median diameter in a wet manner using this device.
- FPIA flow type particle image analyzer
- the ratio of the silver-containing particles (A) in the entire conductive resin composition is, for example, 1-98% by mass, preferably 30-96% by mass, more preferably 50-94% by mass.
- the ratio of the metal-containing particles By setting the ratio of the metal-containing particles to 1% by mass or more, it is easy to increase the thermal conductivity.
- the ratio of the silver-containing particles (A) By setting the ratio of the silver-containing particles (A) to 98% by mass or less, the workability of coating/adhesion can be improved.
- particles consisting essentially of silver can be obtained from, for example, DOWA Hi-Tech Co., Ltd., Fukuda Metal Foil & Powder Co., Ltd., and the like.
- silver-coated resin particles can be obtained from, for example, Mitsubishi Materials Corporation, Sekisui Chemical Co., Ltd., Sanno Co., Ltd., and the like.
- the (meth)acrylic compound (B) is not particularly limited, but includes, for example, a monofunctional or bifunctional (meth)acrylic compound, or a trifunctional or higher polyfunctional (meth)acrylic compound.
- the (meth) acrylic compound represents an acrylic compound, a methacrylic compound, or a mixture thereof, and having a (meth) acrylic group means having one or more acrylic groups, or having one or more methacrylic groups.
- the monofunctional (meth)acrylates include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth) Acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, butoxyethyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate , octylheptyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (
- bifunctional (meth)acrylates include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,3 -butanediol di(meth)acrylate, 2-methyl-1,3-propanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl- 1,5-pentanediol di(meth)acrylate, 1,6-hexane
- trifunctional or higher polyfunctional (meth)acrylates examples include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, di aliphatic (meth)acrylates such as pentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated glycerin tri(meth)acrylate; heterocyclic (meth)acrylates such as isocyanuric acid tri(meth)acrylate; ) acrylates and the like.
- the (meth)acrylic compound (B) can contain at least one selected from these, and can contain a monofunctional (meth)acrylate or a bifunctional (meth)acrylate.
- the ratio of the (meth)acrylic compound (B) in the entire conductive resin composition of the present embodiment is, for example, 0.1 to 15% by mass, preferably 0.5 to 12% by mass, from the viewpoint of the effects of the present invention. , more preferably 1.0 to 10% by mass.
- the polyfunctional epoxy compound (C) contains at least one compound selected from compounds represented by the following general formula (1).
- the compound represented by the following general formula (1) contained in the polyfunctional epoxy compound (C) has a divalent to hexavalent organic group to which a plurality of epoxy group-containing groups are bonded, and has excellent reactivity and crosslink density. increases, sintering of the silver-containing particles is promoted by curing shrinkage when a resin is obtained from the compound, and a highly thermally conductive material with excellent thermal conductivity can be obtained. Furthermore, since the resulting cured product (high thermal conductive material) has a low elastic modulus and excellent flexibility, a semiconductor device or the like provided with the cured product has excellent product reliability due to stress relaxation. Furthermore, the resulting cured product (high thermal conductivity material) is excellent in adhesion to substrates and the like, and is excellent in product reliability. In other words, it is possible to provide a conductive resin composition having an excellent balance of these properties.
- R represents a hydroxyl group or an alkyl group having 1 to 3 carbon atoms, preferably a hydroxyl group or an alkyl group having 1 to 2 carbon atoms, more preferably a hydroxyl group or an alkyl group having 1 carbon atom. Multiple R may be the same or different.
- X represents an alkylene group having 1 to 3 carbon atoms, preferably an alkylene group having 1 to 2 carbon atoms, more preferably an alkylene group having 1 carbon atom. Multiple X's may be the same or different.
- n represents an integer of 2 to 4, preferably 2 or 3;
- Q represents a divalent to hexavalent organic group.
- divalent to hexavalent organic group in Q known organic groups can be used as long as the effects of the present invention are exhibited. can be mentioned.
- Examples of compounds in which Q in general formula (1) is an organic group in general formula (a) include Denacol EX-321 (manufactured by Nagase ChemteX Corporation) and PETG (manufactured by Showa Denko KK). Examples of compounds in which Q in general formula (1) is an organic group in general formula (b) include CDMDG (manufactured by Showa Denko KK). Examples of compounds in which Q in general formula (1) is an organic group in general formula (c) include Denacol EX-313 (manufactured by Nagase ChemteX Corporation).
- Examples of compounds in which Q in general formula (1) is an organic group in general formula (d) include Denacol EX-810 (manufactured by Nagase ChemteX Corporation). In general formula (e), p represents an integer of 1-30, preferably an integer of 10-25. Examples of compounds in which Q in general formula (1) is an organic group in general formula (e) include Denacol EX-861 (manufactured by Nagase ChemteX Corporation).
- Q 1 and Q 2 represent an alkylene group having 1 to 3 carbon atoms or a cycloalkylene group having 3 to 8 carbon atoms, preferably an alkylene group having 1 to 2 carbon atoms or 5 to 8 carbon atoms.
- Examples of compounds in which Q in general formula (1) is an organic group in general formula (f) include Denacol EX-211 and EX-252 (manufactured by Nagase ChemteX Corporation).
- Examples of compounds in which Q in general formula (1) is an organic group in general formula (g) include Denacol EX-512 (manufactured by Nagase ChemteX Corporation). Examples of compounds in which Q in general formula (1) is an organic group in general formula (h) include Denacol EX-614B (manufactured by Nagase ChemteX Corporation). In general formulas (a) to (h), * indicates a bond.
- the polyfunctional epoxy compound (C) is at least one compound selected from compounds in which Q is an organic group represented by general formulas (a), (b) and (c). It preferably contains at least one selected from compounds that are organic groups represented by general formulas (a) and (b), and more preferably contains an organic group represented by general formula (a) More preferably, it contains at least one selected from compounds.
- the polyfunctional epoxy compound (C) is a compound a in which Q in the general formula (1) is an organic group represented by the general formula (a) and n is 3, and Q in the general formula (1) is the general formula
- the ratio of compound a to the total amount of compound a and compound b (a/(a+b)) is 0.01 to 5, preferably 0.05 to 3, more preferably 0.1 to 1.
- the proportion of the polyfunctional epoxy compound (C) in the entire conductive resin composition of the present embodiment is, for example, 0.1 to 20% by mass, preferably 0.2 to 17% by mass, more preferably 0.5 to 15% by mass. % by mass.
- the conductive resin composition further promotes sintering of the silver-containing particles due to curing shrinkage. It is possible to obtain a highly thermally conductive material with even better thermal conductivity. Furthermore, since the resulting cured product (high thermal conductive material) has a lower elastic modulus and is more excellent in flexibility, a semiconductor device or the like provided with the cured product is more excellent in product reliability due to stress relaxation. Furthermore, the resulting cured product (high thermal conductivity material) is excellent in adhesion to substrates and the like, and is excellent in product reliability. In other words, it is possible to provide a conductive resin composition with a better balance of these properties.
- the conductive resin composition of this embodiment can further contain a curing agent (D).
- a curing agent (D) include those having a reactive group that reacts with the epoxy group contained in the polyfunctional epoxy compound (C).
- the curing agent (D) preferably contains a phenolic curing agent. These curing agents are particularly preferred when the thermosetting component contains epoxy groups.
- the phenol-based curing agent may be a low-molecular-weight compound or a high-molecular-weight compound (ie, phenolic resin).
- phenolic resins include novolac-type phenolic resins such as phenol novolak resin, cresol novolak resin, bisphenol novolak resin, and phenol-biphenyl novolak resin; polyvinylphenol; polyfunctional phenolic resins such as triphenylmethane-type phenol resin; modified phenolic resins such as modified phenolic resins and dicyclopentadiene-modified phenolic resins; phenolic aralkyl-type phenolic resins such as phenolaralkyl resins having a phenylene skeleton and/or biphenylene skeleton and naphtholaralkyl resins having a phenylene and/or biphenylene skeleton; be able to.
- the curing agent (D) only one type may be used, or two or more types may be used in combination.
- the amount thereof is, for example, 10 to 120 parts by mass, preferably 20 parts by mass when the amount of the polyfunctional epoxy compound (C) is 100 parts by mass. ⁇ 80 parts by mass.
- the conductive resin composition of the present embodiment can further contain a polymer (E) containing polyrotaxane.
- a polyrotaxane usually comprises a cyclic molecule forming an opening, a linear molecular chain passing through the opening of the cyclic molecule, and blocking groups bonded to both ends of the linear molecular chain. Blocking groups prevent the cyclic molecule from leaving the linear chain.
- a single linear molecular chain can pass through an opening in one or more cyclic molecules.
- the cyclic molecule in the polyrotaxane is not particularly limited as long as it forms an opening through which the linear molecular chain can pass.
- a cyclic molecule does not have to be completely closed by a covalent bond, as long as the linear molecular chain passing through the opening does not break off.
- Cyclic molecules include, for example, cyclodextrin, crown ether, benzocrown, dibenzocrown, dicyclohexanocrown, and derivatives or modifications thereof. From the viewpoint of inclusion ability of linear molecular chains, the cyclic molecule is preferably cyclodextrin or a derivative or modified form thereof.
- the cyclic molecule is cyclodextrin or a derivative or modified form thereof
- part or all of the hydroxy groups in the cyclodextrin are preferably substituted with hydrophobic groups.
- the solubility of the polyrotaxane in organic solvents is improved.
- the relative amount of the cyclic molecule to be included is, for example, 0.001, preferably 0.01, more preferably 0.1 or more, and the upper limit is, for example, 0.7 or less, preferably 0.6 or less, more preferably 0.5 It is below.
- the inclusion amount of the cyclic molecule is within the above range, the mobility of the cyclic molecule on the linear molecular chain is likely to be maintained.
- the linear molecular chain in the polyrotaxane is not particularly limited as long as it is a molecular chain that can penetrate the cyclic molecule and the cyclic molecule can move on the linear molecular chain.
- the straight-chain molecular chain only needs to contain a substantially straight-chain portion, and may have a branched chain or a cyclic substituent or the like.
- the length and molecular weight of the linear portion are not particularly limited.
- linear molecular chains examples include alkylene chains, polyester chains, polyether chains, polyamide chains, and polyacrylate chains. Among these, a polyester chain or a polyether chain is preferred, and a polyether chain is more preferred, from the viewpoint of the flexibility of the linear molecular chain itself.
- Polyether chains are preferably polyethylene glycol chains (polyoxyethylene chains).
- the blocking groups in the polyrotaxane are not particularly limited as long as they are groups arranged at both ends of the linear molecular chain and capable of maintaining the state in which the linear molecular chain penetrates the cyclic molecule.
- the blocking group includes a group having a structure larger than the opening of the cyclic molecule, a group that cannot pass through the opening of the cyclic molecule due to ionic interaction, and the like.
- Specific examples of blocking groups include adamantyl groups, groups containing cyclodextrin, anthracene groups, triphenylene groups, pyrene groups, trityl groups, and isomers and derivatives thereof.
- the combination of a cyclic molecule and a linear molecular chain is preferably a combination of ⁇ -cyclodextrin or a derivative thereof as the cyclic molecule and a polyethylene glycol chain or derivative thereof as the linear molecular chain. .
- This combination facilitates movement of the cyclic molecule on the linear molecular chain.
- this combination also has the advantage of being relatively easy to synthesize.
- the polyrotaxane preferably has crosslinkable groups. By having a crosslinkable group in the polyrotaxane, the thermosetting property, adhesiveness, etc. of the conductive resin composition are improved.
- the cyclic molecule in the polyrotaxane preferably has a crosslinkable group. Since the cyclic molecule has a crosslinkable group, the cyclic molecule maintains a state in which it can slide along the linear molecular chain even after the composition is thermally cured (crosslinked). Therefore, it is possible to further enhance the flexibility and stretchability of the film after thermosetting.
- the crosslinkable group is preferably a cationic crosslinkable group or a radical crosslinkable group, more preferably a radical crosslinkable group.
- the crosslinkable groups are preferably ethylenic carbon-carbon double bond-containing groups such as (meth)acryloyl groups.
- the crosslinkable group may contain an epoxy group and/or an oxetanyl group.
- the polyrotaxane may be synthesized with reference to a known method, or may be a commercially available product. Commercially available products include the "Serum” (registered trademark, SeRM in the alphabet) series sold by ASM Corporation.
- the conductive resin composition of the present embodiment may contain only one type of polyrotaxane, or may contain two or more types.
- the polymer (E) can contain known resins other than polyrotaxane within the scope of the effects of the present invention.
- resins include silicone resins, (meth)acrylic resins, phenol resins, polystyrene resins, melamine resins, polyamide resins, and polytetrafluoroethylene resins.
- the content of the polyrotaxane in 100% by mass of the polymer (E) is 75% by mass to 100% by mass, preferably 80% by mass to 100% by mass, more preferably 90% by mass to 100% by mass, especially It is preferably 95% by mass to 100% by mass.
- the proportion of the polymer (E) in the entire conductive resin composition of the present embodiment is, for example, 0.1 to 10% by mass, preferably 0.2 to 8% by mass, more preferably 0.3 to 5% by mass. be.
- the conductive resin composition of the present embodiment can further contain an organic solvent (F).
- organic solvent (F) examples include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, Propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, tripropylene glycol monobutyl ether, methyl methoxybutanol, ⁇ -terpineol, ⁇ -terpineol, hexylene glycol, benzyl alcohol, 2-phenyl Alcohols such as ethyl alcohol, isopalmityl alcohol, isostearyl alcohol, lauryl alcohol, ethylene glycol, propylene
- the amount is not particularly limited.
- the amount used may be appropriately adjusted based on the desired fluidity and the like.
- the organic solvent (F) is used in such an amount that the nonvolatile component concentration of the conductive resin composition is 50 to 95% by mass.
- the conductive resin composition of this embodiment can further contain a curing accelerator.
- a curing accelerator typically accelerates the reaction between the polyfunctional epoxy compound (C) and the curing agent (D).
- curing accelerators include phosphorus atom-containing compounds such as imidazole compounds, organic phosphines, tetrasubstituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, and adducts of phosphonium compounds and silane compounds; dicyandiamide, 1,8-diazabicyclo[5.4.0]undecene-7, amidines and tertiary amines such as benzyldimethylamine; nitrogen atom-containing compounds such as quaternary ammonium salts of the above amidines or the above tertiary amines; be done.
- a hardening accelerator only 1 type may be used and 2 or more types may be used together.
- the conductive resin composition of this embodiment can further contain a curing accelerator.
- the radical polymerization initiator can, for example, prevent insufficient curing, allow the curing reaction to proceed sufficiently at a relatively low temperature (eg, 180° C.), or further improve the adhesive strength. sometimes it can be done.
- Examples of radical polymerization initiators include peroxides and azo compounds.
- peroxides examples include organic peroxides such as diacyl peroxide, dialkyl peroxide, and peroxyketals, more specifically, ketone peroxides such as methyl ethyl ketone peroxide and cyclohexanone peroxide; Peroxyketals such as 1,1-di(t-butylperoxy)cyclohexane and 2,2-di(4,4-di(t-butylperoxy)cyclohexyl)propane; Hydroperoxides such as p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-butyl hydroperoxide; di(2-t-butylperoxyisopropyl)benzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, t-buty
- Azo compounds include 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2, 4-dimethylvaleronitrile) and the like.
- a radical polymerization initiator only one type may be used, or two or more types may be used in combination.
- the conductive resin composition of the present embodiment can contain other components such as a curing accelerator, a silane coupling agent, a plasticizer, and an adhesion imparting agent.
- the adhesive force can be further improved, and by including a plasticizer, the storage elastic modulus can be lowered. And it becomes easy to suppress the fall of the adhesive force by a heat cycle further.
- the conductive resin composition of the present embodiment is preferably pasty at 20°C. That is, the conductive resin composition (paste composition) of the present embodiment can preferably be applied to a substrate or the like like a paste at 20°C. As a result, the conductive resin composition of the present embodiment can be preferably used as an adhesive for semiconductor elements or the like. Of course, depending on the applied process, the conductive resin composition of the present embodiment may be in the form of a relatively low-viscosity varnish.
- the conductive resin composition of the present embodiment can be obtained by mixing each of the components described above and, if necessary, other components by a conventionally known method.
- a highly thermally conductive material can be obtained by sintering the conductive resin composition of the present embodiment. By changing the shape of the high thermal conductivity material, it can be applied to various parts that require heat dissipation in the fields of automobiles and electrical machinery.
- a semiconductor device can be manufactured using the conductive resin composition of the present embodiment.
- a semiconductor device can be manufactured by using the conductive resin composition of the present embodiment as an "adhesive" between a substrate and a semiconductor element.
- the semiconductor device of the present embodiment includes, for example, a substrate and a semiconductor element mounted on the substrate via an adhesive layer obtained by sintering the conductive resin composition by heat treatment. Prepare.
- the stress is relaxed, and the adhesiveness of the adhesive layer is less likely to deteriorate due to heat cycles. That is, the reliability of the semiconductor device of this embodiment is high.
- semiconductor devices include ICs, LSIs, power semiconductor devices (power semiconductors), and various other devices.
- substrates include various semiconductor wafers, lead frames, BGA substrates, mounting substrates, heat spreaders, and heat sinks.
- FIG. 1 is a cross-sectional view showing an example of a semiconductor device.
- the semiconductor device 100 includes a base material 30 and a semiconductor element 20 mounted on the base material 30 via an adhesive layer 10 (die attach material) that is a heat-treated body of a conductive resin composition.
- adhesive layer 10 die attach material
- the semiconductor element 20 and the base material 30 are electrically connected, for example, via bonding wires 40 or the like. Also, the semiconductor element 20 is sealed with a sealing resin 50, for example.
- the thickness of the adhesive layer 10 is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, and even more preferably 20 ⁇ m or more. Thereby, the stress absorption capacity of the conductive resin composition can be improved, and the heat cycle resistance can be improved.
- the thickness of the adhesive layer 10 is, for example, 100 ⁇ m or less, preferably 50 ⁇ m or less.
- the base material 30 is, for example, a lead frame.
- the semiconductor element 20 is mounted on the die pad 32 or the base material 30 with the adhesive layer 10 interposed therebetween.
- the semiconductor element 20 is electrically connected to the outer leads 34 (the base material 30) via bonding wires 40, for example.
- the base material 30, which is a lead frame, is composed of, for example, 42 alloy, a Cu frame, or the like.
- the substrate 30 may be an organic substrate or a ceramic substrate.
- organic substrates include those made of epoxy resin, cyanate resin, maleimide resin, or the like.
- the surface of the base material 30 may be coated with a metal such as silver or gold, for example. This improves the adhesiveness between the adhesive layer 10 and the substrate 30 .
- FIG. 2 is a cross-sectional view showing another example of the semiconductor device 100 different from that in FIG.
- the base material 30 is, for example, an interposer.
- a plurality of solder balls 52 are formed on the surface of the substrate 30, which is the interposer, opposite to the surface on which the semiconductor element 20 is mounted. In this case, the semiconductor device 100 will be connected to another wiring board through the solder balls 52 .
- the base material 30 is coated with a conductive resin composition, and then the semiconductor element 20 is arranged thereon. That is, the substrate 30, the conductive resin composition, and the semiconductor element 20 are laminated in this order.
- the method of applying the conductive resin composition is not particularly limited. Specifically, a dispensing method, a printing method, an inkjet method, and the like can be mentioned.
- the conductive resin composition is heat-cured.
- Thermal curing is preferably carried out by pre-curing and post-curing.
- thermosetting the conductive resin composition is made into a heat-treated body (cured product).
- thermosetting heat treatment
- the metal-containing particles in the conductive resin composition are aggregated, and a structure is formed in the adhesive layer 10 in which interfaces between a plurality of metal-containing particles have disappeared.
- the substrate 30 and the semiconductor element 20 are adhered via the adhesive layer 10 .
- the semiconductor element 20 and the base material 30 are electrically connected using bonding wires 40 .
- the semiconductor element 20 is sealed with the sealing resin 50 .
- a semiconductor device can be manufactured.
- Aliphatic polyfunctional epoxy compound 1 trimethylolpropane polyglycidyl ether (a mixture of compounds represented by the following chemical formula, Denacol EX-321L, manufactured by Nagase Chemtech)
- Aliphatic polyfunctional epoxy compound 2 epoxidation reaction product of pentaerythritol tetraallyl ether with hydrogen peroxide (compound represented by the following chemical formula, Showfree PETG, manufactured by Showa Denko)
- Aliphatic polyfunctional epoxy compound 3 epoxidation reaction product of pentaerythritol tetraallyl ether with hydrogen peroxide (compound represented by the following chemical formula, Showfree CDMDG, manufactured by Showa Denko)
- Epoxy resin 4 bisphenol F type epoxy resin (manufactured by Nippon Kayaku, RE-303S)
- Epoxy resin 5 aminophenol type epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER630)
- Acrylic monomer 1 ethylene glycol dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., Light Ester EG)
- Acrylic monomer 2 1,4-cyclohexanedimethanol monoacrylate (manufactured by Nippon Kasei Co., Ltd., CHDMMA, monofunctional acrylic)
- Polyrotaxane 1 SA1305P-20: 50% by mass solution of polyrotaxane ethyl acetate sold by ASM Co., Ltd., cyclic molecule in polyrotaxane contains acryloyl group, total weight average molecular weight (representative value): 1 million, methacrylic equivalent ( Representative value): 1500 g / eq
- Curing agent Phenolic resin having a bisphenol F skeleton (DIC-BPF manufactured by DIC)
- Radical polymerization initiator - Radical polymerization initiator 1: Dicumyl peroxide (manufactured by Kayaku Akzo Co., Ltd., Perkadox BC)
- Curing accelerator 1 2-phenyl-1H-imidazole-4,5-dimethanol (manufactured by Shikoku Kasei Kogyo Co., Ltd., 2PHZ-PW)
- ⁇ Silver filler 1 Dowa Electronics Co., Ltd., AG-DSB-114, spherical, D 50 : 0.7 ⁇ m, specific surface area: 1.05 m 2 /g, tap density 5.25 g/cm 3 , circularity: 0.953 ⁇ Silver filler 2: HKD-12 manufactured by Fukuda Metal Foil & Powder Co., Ltd., scale-like, median diameter D 50 : 7.6 ⁇ m, specific surface area: 0.315 m 2 /g, tap density: 5.5 g/cm 3
- Solvent 1 Tripropylene glycol mono-n-butyl ether (BFTG, manufactured by Nippon Emulsifier Co., Ltd., boiling point 274 ° C.)
- Examples 1-8, Comparative Examples 1-2 Each raw material component was mixed according to the compounding amount shown in Table 1 to obtain a varnish. Next, the obtained varnish was blended according to the blending amounts shown in Table 1, and kneaded at room temperature in a three-roll mill. Thus, a conductive resin composition was produced.
- the conductive resin composition was applied onto a glass plate, heated from 30° C. to 200° C. over 60 minutes in a nitrogen atmosphere, and then heat-treated at 200° C. for 120 minutes. As a result, a heat-treated body (cured product) of the conductive resin composition having a thickness of 0.05 mm was obtained.
- the resistance value of the surface of the heat-treated body was measured using a direct current four-electrode method with a milliohmmeter (manufactured by Hioki Co., Ltd.) and electrodes with an electrode spacing of 40 mm.
- the heat-treated body of the conductive resin composition was cut into pieces of about 0.1 mm x about 10 mm x about 4 mm to obtain strip-shaped samples for evaluation.
- the storage modulus (E′) at 25° C. was measured by DMA (dynamic viscoelasticity measurement, tensile mode) under the conditions of a heating rate of 5° C./min and a frequency of 10 Hz.
- the semiconductor device for evaluation produced as described above was treated in the same manner as described above at a temperature of 60° C. and a humidity of 60% for 48 hours to obtain an evaluation sample.
- the chip adhesion strength using a 4000 universal bond tester (manufactured by Nordson Dage), the strength when shearing at a tool speed of 500 ⁇ m / s at a position of 50 ⁇ m in height from the lead frame when heating at 260 ° C. It was evaluated as strength.
- the cured product obtained from the conductive resin composition containing the polyfunctional epoxy compound has low volume resistivity and excellent thermal conductivity, and has a low storage elastic modulus and is stress-relaxed. Furthermore, even after the constant temperature moisture absorption test, the adhesion strength is high and peeling is suppressed.
- semiconductor device adhesive layer 20 semiconductor element 30 base material 32 die pad 34 outer lead 40 bonding wire 50 sealing resin 52 solder ball
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Abstract
Description
すなわち、本発明は、以下に示すことができる。 The present inventors have found that the above problems can be solved by using a combination of a (meth)acrylic compound and a specific polyfunctional epoxy compound, and have completed the present invention.
That is, the present invention can be shown below.
(A)銀含有粒子と、
(B)(メタ)アクリル化合物と、
(C)下記一般式(1)で表される化合物から選択される少なくとも1種の多官能エポキシ化合物と、
を含む、導電性樹脂組成物が提供される。
Qは、2~6価の有機基を示す。
Xは炭素数1~3のアルキレン基を示し、複数存在するXは同一でも異なっていてもよい。
mは0~2の整数、nは2~4の整数を示す。) According to the invention,
(A) silver-containing particles;
(B) a (meth) acrylic compound;
(C) at least one polyfunctional epoxy compound selected from compounds represented by the following general formula (1);
A conductive resin composition is provided.
Q represents a divalent to hexavalent organic group.
X represents an alkylene group having 1 to 3 carbon atoms, and multiple X's may be the same or different.
m is an integer of 0-2, n is an integer of 2-4. )
前記導電性樹脂組成物を焼結して得られる高熱伝導性材料が提供される。 According to the invention,
A high thermal conductivity material obtained by sintering the conductive resin composition is provided.
基材と、
前記基材上に接着層を介して搭載された半導体素子と、を備え、
前記接着層は、前記導電性樹脂組成物を焼結してなる、半導体装置が提供される。 According to the invention,
a substrate;
A semiconductor element mounted on the base material via an adhesive layer,
A semiconductor device is provided in which the adhesive layer is formed by sintering the conductive resin composition.
本明細書における「(メタ)アクリル」との表記は、アクリルとメタクリルの両方を包含する概念を表す。「(メタ)アクリレート」「(メタ)アクリロイル」等の類似の表記についても同様である。 In the description of a group (atomic group) in the present specification, a description without indicating whether it is substituted or unsubstituted includes both those having no substituent and those having a substituent. For example, the term “alkyl group” includes not only alkyl groups without substituents (unsubstituted alkyl groups) but also alkyl groups with substituents (substituted alkyl groups).
The notation "(meth)acryl" used herein represents a concept that includes both acryl and methacryl. The same applies to similar expressions such as "(meth)acrylate" and "(meth)acryloyl".
(A)銀含有粒子と、
(B)(メタ)アクリル化合物と、
(C)下記一般式(1)で表される化合物から選択される少なくとも1種の多官能エポキシ化合物と、を含む。
これにより、硬化収縮によって銀含有粒子の焼結が促進されて熱伝導性に優れた高熱伝導性材料が得られ、さらに弾性率が低く応力が緩和され、かつ基板等との密着性に優れていることから製品信頼性に優れた高熱伝導性材料を得ることができる。
金属等の導電性物質のように熱伝導性と電気伝導性の両方の大部分を自由電子が担う場合、ウィーデマン・フランツ則により、熱伝導性は体積抵抗率により評価することができる。すなわち、体積抵抗率は単位体積あたりの電気抵抗値であり、電気抵抗値が低ければ自由電子がキャリアとなり電気が通りやすいことを表し、熱の伝わりやすさ(熱伝導性)の指標にもなる。 The conductive resin composition of the present embodiment is
(A) silver-containing particles;
(B) a (meth) acrylic compound;
(C) at least one polyfunctional epoxy compound selected from compounds represented by the following general formula (1).
As a result, the sintering of the silver-containing particles is promoted by curing shrinkage, and a high thermal conductivity material with excellent thermal conductivity is obtained.In addition, the elastic modulus is low, the stress is relaxed, and the adhesiveness to the substrate etc. is excellent. Therefore, a high thermal conductivity material with excellent product reliability can be obtained.
In the case where free electrons bear most of both thermal conductivity and electrical conductivity as in conductive substances such as metals, thermal conductivity can be evaluated by volume resistivity according to the Wiedemann-Franz law. In other words, the volume resistivity is the electrical resistance value per unit volume. If the electrical resistance value is low, the free electrons become carriers and electricity easily passes through. .
銀含有粒子(A)は、適切な熱処理によってシンタリング(焼結)を起こし、粒子連結構造(シンタリング構造)を形成することができる。 [Silver-containing particles (A)]
The silver-containing particles (A) can be sintered by an appropriate heat treatment to form a particle connecting structure (sintering structure).
なお、本実施形態において、「球状」とは、完全な真球に限られず、表面に若干の凹凸がある形状等も包含する。その円形度は、例えば0.90以上、好ましくは0.92以上、より好ましくは0.94以上である。 By including the silver-containing particles (a2) in the silver-containing particles (A), it is possible to suppress resin cracks in the molded product obtained from the conductive resin composition and to suppress the coefficient of linear expansion.
In the present embodiment, the term “spherical” is not limited to a perfect sphere, and includes a shape with some irregularities on the surface. Its circularity is, for example, 0.90 or more, preferably 0.92 or more, and more preferably 0.94 or more.
銀コート樹脂粒子においては、樹脂粒子の表面の少なくとも一部の領域を銀層が覆っていればよい。もちろん、樹脂粒子の表面の全面を銀が覆っていてもよい。 Generally, in order to increase the thermal conductivity, it is considered to increase the amount of silver-containing particles. However, since metals are generally "hard", too much silver-containing particles may result in too high a modulus after sintering. Part or all of the silver-containing particles are silver-coated resin particles, making it possible to easily design a conductive resin composition from which a cured product having desired thermal conductivity and storage elastic modulus can be obtained.
In the silver-coated resin particles, it is sufficient that at least a part of the surface of the resin particles is covered with a silver layer. Of course, the entire surface of the resin particles may be covered with silver.
別観点として、銀コート樹脂粒子をある断面で切断したときには、その断面の周囲全部に銀層が確認されることが好ましい。 Specifically, in the silver-coated resin particles, the silver layer preferably covers 50% or more, more preferably 75% or more, and still more preferably 90% or more of the surface of the resin particles. Particularly preferably, in silver-coated resin particles, the silver layer covers substantially the entire surface of the resin particles.
From another point of view, when the silver-coated resin particles are cut along a certain cross section, it is preferable that the silver layer is observed all around the cross section.
弾性特性や耐熱性の観点から、樹脂は、シリコーン樹脂または(メタ)アクリル樹脂が好ましい。 Examples of the "resin" in the silver-coated resin particles include silicone resins, (meth)acrylic resins, phenol resins, polystyrene resins, melamine resins, polyamide resins, polytetrafluoroethylene resins, and the like. Of course, resins other than these may be used. Moreover, only one resin may be used, or two or more resins may be used in combination.
From the viewpoint of elastic properties and heat resistance, the resin is preferably a silicone resin or a (meth)acrylic resin.
銀含有粒子の粒度分布(横軸:粒子径、縦軸:頻度)は、単峰性であっても多峰性であってもよい。 The median diameter D50 of the silver-containing particles (A) is, for example, 0.01-50 μm, preferably 0.1-20 μm, more preferably 0.5-10 μm. By setting D50 to an appropriate value, it is easy to balance thermal conductivity, sinterability, resistance to heat cycles, and the like. Also, by setting D50 to an appropriate value, it may be possible to improve the workability of application/adhesion.
The particle size distribution (horizontal axis: particle size, vertical axis: frequency) of the silver-containing particles may be unimodal or multimodal.
球状の銀含有粒子(a1)の比表面積は、例えば0.1~2.5m2/g、好ましくは0.5~2.3m2/g、より好ましくは0.8~2.0m2/gである。
球状の銀含有粒子(a1)のタップ密度は、例えば1.5~6.0g/cm3、好ましくは2.5~5.8g/cm3、より好ましくは4.5~5.5g/cm3である。
球状の銀含有粒子(a1)の円形度は、例えば0.90以上、好ましくは0.92以上、より好ましくは0.94以上である。
これらの各特性を満たすことにより、熱伝導性、焼結性、ヒートサイクルに対する耐性などのバランスに優れる。 The median diameter D 50 of the spherical silver-containing particles (a1) is, for example, 0.1-20 μm, preferably 0.5-10 μm, more preferably 0.5-5.0 μm.
The specific surface area of the spherical silver-containing particles (a1) is, for example, 0.1 to 2.5 m 2 /g, preferably 0.5 to 2.3 m 2 /g, more preferably 0.8 to 2.0 m 2 /g. is g.
The tap density of the spherical silver-containing particles (a1) is, for example, 1.5 to 6.0 g/cm 3 , preferably 2.5 to 5.8 g/cm 3 , more preferably 4.5 to 5.5 g/cm 3 .
The circularity of the spherical silver-containing particles (a1) is, for example, 0.90 or more, preferably 0.92 or more, and more preferably 0.94 or more.
Satisfying each of these properties provides an excellent balance of thermal conductivity, sinterability, resistance to heat cycles, and the like.
鱗片状の銀含有粒子(a2-1)の比表面積は、例えば0.1~2.5m2/g、好ましくは0.2~2.0m2/g、より好ましくは0.25~1.2m2/gである。
鱗片状の銀含有粒子(a2-1)のタップ密度は、例えば1.5~6.0g/cm3、好ましくは2.5~5.9g/cm3、より好ましくは4.0~5.8g/cm3である。
これらの各特性を満たすことにより、熱伝導性、焼結性、ヒートサイクルに対する耐性などのバランスに優れる。 The median diameter D50 of the scale-like silver-containing particles (a2-1) is, for example, 0.1 to 20 μm, preferably 1.0 to 15 μm, more preferably 2.0 to 10 μm.
The specific surface area of the scale-like silver-containing particles (a2-1) is, for example, 0.1 to 2.5 m 2 /g, preferably 0.2 to 2.0 m 2 /g, more preferably 0.25 to 1.0 m 2 /g. 2 m 2 /g.
The tap density of the scale-like silver-containing particles (a2-1) is, for example, 1.5 to 6.0 g/cm 3 , preferably 2.5 to 5.9 g/cm 3 , more preferably 4.0 to 5.0 g/cm 3 . 8 g/cm 3 .
Satisfying each of these properties provides an excellent balance of thermal conductivity, sinterability, resistance to heat cycles, and the like.
これにより、鱗片状の銀含有粒子間の空隙に、球状の銀含有粒子が効率的に充填され、銀含有粒子同士の接触率が特に向上することから、当該ペースト状重合性組成物の焼結後においてネットワークが容易に形成され熱伝導性および電気伝導性が特に向上する。 The ratio (a1/a2-1) of the median diameter D50 of the spherical silver-containing particles (a1) to the median diameter D50 of the scale-like silver-containing particles (a2-1) is preferably 0.01 or more and 0.8 or less. , more preferably 0.05 or more and 0.6 or less.
As a result, the voids between the scale-like silver-containing particles are efficiently filled with the spherical silver-containing particles, and the contact ratio between the silver-containing particles is particularly improved. A network is easily formed later, and thermal conductivity and electrical conductivity are particularly improved.
これにより、銀含有粒子の充填率が向上し、銀含有粒子同士の接触率が特に向上することから、当該ペースト状重合性組成物の焼結後においてネットワークが容易に形成され熱伝導性および電気伝導性が特に向上する。 The ratio (a1/a2-1) of the tap density of the spherical silver-containing particles (a1) to the tap density of the scale-like silver-containing particles (a2-1) is preferably 0.5 or more and 2.0 or less, more preferably It is 0.7 or more and 1.2 or less.
As a result, the filling rate of the silver-containing particles is improved, and the contact ratio between the silver-containing particles is particularly improved. Conductivity is particularly improved.
(メタ)アクリル化合物(B)としては、特に限定されないが、例えば、単官能または2官能(メタ)アクリル化合物、または3官能以上の多官能(メタ)アクリル化合物を挙げることができる。本実施形態において、(メタ)アクリル化合物とは、アクリル化合物、メタクリル化合物またはこれらの混合物を表し、(メタ)アクリル基を有するとは、アクリル基を1以上有する、またはメタクリル基を1以上有することを表す。 [(Meth) acrylic compound (B)]
The (meth)acrylic compound (B) is not particularly limited, but includes, for example, a monofunctional or bifunctional (meth)acrylic compound, or a trifunctional or higher polyfunctional (meth)acrylic compound. In the present embodiment, the (meth) acrylic compound represents an acrylic compound, a methacrylic compound, or a mixture thereof, and having a (meth) acrylic group means having one or more acrylic groups, or having one or more methacrylic groups. represents
シクロペンチル(メタ)アクリレート、シクロヘキシル(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、シクロペンチル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、イソボルニル(メタ)アクリレート、3-メチル-3-オキセタニルメチル(メタ)アクリレート、1-アダマンチル(メタ)アクリレートのような脂環式(メタ)アクリレート;
フェニル(メタ)アクリレート、ノニルフェニル(メタ)アクリレート、p-クミルフェニル(メタ)アクリレート、o-ビフェニル(メタ)アクリレート、1-ナフチル(メタ)アクリレート、2-ナフチル(メタ)アクリレート、ベンジル(メタ)アクリレート、2-ヒドロキシ-3-フェノキシプロピル(メタ)アクリレート、2-ヒドロキシ-3-(o-フェニルフェノキシ)プロピル(メタ)アクリレート、2-ヒドロキシ-3-(1-ナフトキシ)プロピル(メタ)アクリレート、2-ヒドロキシ-3-(2-ナフトキシ)プロピル(メタ)アクリレートのような芳香族(メタ)アクリレート;
2-テトラヒドロフルフリル(メタ)アクリレート、N-(メタ)アクリロイルオキシエチルヘキサヒドロフタルイミド、2-(メタ)アクリロイルオキシエチル-N-カルバゾールのような複素環式(メタ)アクリレートが挙げられる。 In the present embodiment, the monofunctional (meth)acrylates include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth) Acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, butoxyethyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate , octylheptyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, hexadecyl (meth)acrylate, stearyl (meth)acrylate, behenyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, 2 - aliphatic (meth)acrylates such as hydroxybutyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate;
Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 1,4-cyclohexanedimethanol mono (meth)acrylate, cyclopentyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl ( Alicyclic (meth)acrylates such as meth)acrylate, 3-methyl-3-oxetanylmethyl (meth)acrylate, 1-adamantyl (meth)acrylate;
Phenyl (meth)acrylate, nonylphenyl (meth)acrylate, p-cumylphenyl (meth)acrylate, o-biphenyl (meth)acrylate, 1-naphthyl (meth)acrylate, 2-naphthyl (meth)acrylate, benzyl (meth)acrylate , 2-hydroxy-3-phenoxypropyl (meth)acrylate, 2-hydroxy-3-(o-phenylphenoxy)propyl (meth)acrylate, 2-hydroxy-3-(1-naphthoxy)propyl (meth)acrylate, 2 - aromatic (meth)acrylates such as hydroxy-3-(2-naphthoxy)propyl (meth)acrylate;
Heterocyclic (meth)acrylates such as 2-tetrahydrofurfuryl (meth)acrylate, N-(meth)acryloyloxyethylhexahydrophthalimide, and 2-(meth)acryloyloxyethyl-N-carbazole are included.
シクロヘキサンジメタノール(メタ)アクリレート、トリシクロデカンジメタノール(メタ)アクリレート、水添ビスフェノールAジ(メタ)アクリレート、水添ビスフェノールFジ(メタ)アクリレートのような脂環式(メタ)アクリレート;
ビスフェノールAジ(メタ)アクリレート、ビスフェノールFジ(メタ)アクリレート、ビスフェノールAFジ(メタ)アクリレート、エトキシ化ビスフェノールAジ(メタ)アクリレート、フルオレン型ジ(メタ)アクリレートのような芳香族(メタ)アクリレート;
イソシアヌル酸ジ(メタ)アクリレートのような複素環式(メタ)アクリレート等が挙げられる。 Examples of bifunctional (meth)acrylates include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 1,3 -butanediol di(meth)acrylate, 2-methyl-1,3-propanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 3-methyl- 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 2-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, 1,9-nonanediol Aliphatic (meth)acrylates such as di(meth)acrylate, 1,10-decanediol di(meth)acrylate, glycerin di(meth)acrylate, tricyclodecanedimethanol (meth)acrylate;
Alicyclic (meth)acrylates such as cyclohexanedimethanol (meth)acrylate, tricyclodecanedimethanol (meth)acrylate, hydrogenated bisphenol A di(meth)acrylate, hydrogenated bisphenol F di(meth)acrylate;
Aromatic (meth)acrylates such as bisphenol A di(meth)acrylate, bisphenol F di(meth)acrylate, bisphenol AF di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, fluorene type di(meth)acrylate ;
Heterocyclic (meth)acrylates such as isocyanuric acid di(meth)acrylate and the like are included.
多官能エポキシ化合物(C)は、下記一般式(1)で表される化合物から選択される少なくとも1種を含む。
多官能エポキシ化合物(C)に含まれる下記一般式(1)で表される化合物は、複数のエポキシ基含有基が結合する2~6価の有機基を備えており、反応性に優れ架橋密度が高くなることから、当該化合物から樹脂が得られる際の硬化収縮によって銀含有粒子の焼結が促進されて熱伝導性に優れた高熱伝導性材料を得ることができる。さらに、得られる硬化物(高熱伝導性材料)は弾性率が低く柔軟性に優れることから、当該硬化物を備える半導体装置等は応力緩和により製品信頼性に優れる。さらに、得られる硬化物(高熱伝導性材料)は基板等との密着性にも優れており製品信頼性に優れる。言い換えればこれらの特性のバランスに優れた導電性樹脂組成物を提供することができる。 [Polyfunctional epoxy compound (C)]
The polyfunctional epoxy compound (C) contains at least one compound selected from compounds represented by the following general formula (1).
The compound represented by the following general formula (1) contained in the polyfunctional epoxy compound (C) has a divalent to hexavalent organic group to which a plurality of epoxy group-containing groups are bonded, and has excellent reactivity and crosslink density. increases, sintering of the silver-containing particles is promoted by curing shrinkage when a resin is obtained from the compound, and a highly thermally conductive material with excellent thermal conductivity can be obtained. Furthermore, since the resulting cured product (high thermal conductive material) has a low elastic modulus and excellent flexibility, a semiconductor device or the like provided with the cured product has excellent product reliability due to stress relaxation. Furthermore, the resulting cured product (high thermal conductivity material) is excellent in adhesion to substrates and the like, and is excellent in product reliability. In other words, it is possible to provide a conductive resin composition having an excellent balance of these properties.
nは2~4の整数を示し、好ましくは2または3である。
Qは、2~6価の有機基を示す。 m represents an integer of 0 to 2, preferably 0 or 1;
n represents an integer of 2 to 4, preferably 2 or 3;
Q represents a divalent to hexavalent organic group.
一般式(1)のQが一般式(b)の有機基である化合物としては、CDMDG(昭和電工社製)等が挙げられる。
一般式(1)のQが一般式(c)の有機基である化合物としては、デナコールEX-313(ナガセケムテックス社製)等が挙げられる。
一般式(1)のQが一般式(d)の有機基である化合物としては、デナコールEX-810(ナガセケムテックス社製)等が挙げられる。
一般式(e)中、pは1~30の整数を示し、好ましくは10~25の整数を示す。
一般式(1)のQが一般式(e)の有機基である化合物としては、デナコールEX-861(ナガセケムテックス社製)等が挙げられる。 Examples of compounds in which Q in general formula (1) is an organic group in general formula (a) include Denacol EX-321 (manufactured by Nagase ChemteX Corporation) and PETG (manufactured by Showa Denko KK).
Examples of compounds in which Q in general formula (1) is an organic group in general formula (b) include CDMDG (manufactured by Showa Denko KK).
Examples of compounds in which Q in general formula (1) is an organic group in general formula (c) include Denacol EX-313 (manufactured by Nagase ChemteX Corporation).
Examples of compounds in which Q in general formula (1) is an organic group in general formula (d) include Denacol EX-810 (manufactured by Nagase ChemteX Corporation).
In general formula (e), p represents an integer of 1-30, preferably an integer of 10-25.
Examples of compounds in which Q in general formula (1) is an organic group in general formula (e) include Denacol EX-861 (manufactured by Nagase ChemteX Corporation).
一般式(1)のQが一般式(f)の有機基である化合物としては、デナコールEX-211、EX-252(ナガセケムテックス社製)等が挙げられる。
一般式(1)のQが一般式(g)の有機基である化合物としては、デナコールEX-512(ナガセケムテックス社製)等が挙げられる。
一般式(1)のQが一般式(h)の有機基である化合物としては、デナコールEX-614B(ナガセケムテックス社製)等が挙げられる。
一般式(a)~(h)中、*は結合手を示す。 In general formula (f), Q 1 and Q 2 represent an alkylene group having 1 to 3 carbon atoms or a cycloalkylene group having 3 to 8 carbon atoms, preferably an alkylene group having 1 to 2 carbon atoms or 5 to 8 carbon atoms. is a cycloalkylene group of R 1 and R 2 represent an alkylene group having 1 to 3 carbon atoms, preferably an alkylene group having 1 to 2 carbon atoms.
Examples of compounds in which Q in general formula (1) is an organic group in general formula (f) include Denacol EX-211 and EX-252 (manufactured by Nagase ChemteX Corporation).
Examples of compounds in which Q in general formula (1) is an organic group in general formula (g) include Denacol EX-512 (manufactured by Nagase ChemteX Corporation).
Examples of compounds in which Q in general formula (1) is an organic group in general formula (h) include Denacol EX-614B (manufactured by Nagase ChemteX Corporation).
In general formulas (a) to (h), * indicates a bond.
本実施形態においては、多官能エポキシ化合物(C)と(メタ)アクリル化合物(B)とを組み合わせて用いることにより、導電性樹脂組成物は、硬化収縮によって銀含有粒子の焼結がより促進されて熱伝導性にさらに優れた高熱伝導性材料を得ることができる。さらに、得られる硬化物(高熱伝導性材料)は弾性率がより低く柔軟性にさらに優れることから、当該硬化物を備える半導体装置等は応力緩和により製品信頼性にさらに優れる。さらに、得られる硬化物(高熱伝導性材料)は基板等との密着性にも優れており製品信頼性に優れる。言い換えればこれらの特性のバランスにさらに優れた導電性樹脂組成物を提供することができる。 10 to 85 parts by mass, preferably 15 to 60 parts by mass, more preferably 20 to 50 parts by mass of the (meth)acrylic compound (B) can be contained with respect to 100 parts by mass of the polyfunctional epoxy compound (C).
In the present embodiment, by using the polyfunctional epoxy compound (C) and the (meth)acrylic compound (B) in combination, the conductive resin composition further promotes sintering of the silver-containing particles due to curing shrinkage. It is possible to obtain a highly thermally conductive material with even better thermal conductivity. Furthermore, since the resulting cured product (high thermal conductive material) has a lower elastic modulus and is more excellent in flexibility, a semiconductor device or the like provided with the cured product is more excellent in product reliability due to stress relaxation. Furthermore, the resulting cured product (high thermal conductivity material) is excellent in adhesion to substrates and the like, and is excellent in product reliability. In other words, it is possible to provide a conductive resin composition with a better balance of these properties.
本実施形態の導電性樹脂組成物は、さらに硬化剤(D)を含むことができる。
硬化剤(D)としては、多官能エポキシ化合物(C)に含まれるエポキシ基と反応する反応性基を有するものを挙げることができる。 [Curing agent (D)]
The conductive resin composition of this embodiment can further contain a curing agent (D).
Examples of the curing agent (D) include those having a reactive group that reacts with the epoxy group contained in the polyfunctional epoxy compound (C).
フェノール系硬化剤は、低分子化合物あってもよいし、高分子化合物(すなわちフェノール樹脂)であってもよい。 The curing agent (D) preferably contains a phenolic curing agent. These curing agents are particularly preferred when the thermosetting component contains epoxy groups.
The phenol-based curing agent may be a low-molecular-weight compound or a high-molecular-weight compound (ie, phenolic resin).
硬化剤(D)を用いる場合、1種のみを用いてもよいし、2種以上を併用してもよい。 Specific examples of phenolic resins include novolac-type phenolic resins such as phenol novolak resin, cresol novolak resin, bisphenol novolak resin, and phenol-biphenyl novolak resin; polyvinylphenol; polyfunctional phenolic resins such as triphenylmethane-type phenol resin; modified phenolic resins such as modified phenolic resins and dicyclopentadiene-modified phenolic resins; phenolic aralkyl-type phenolic resins such as phenolaralkyl resins having a phenylene skeleton and/or biphenylene skeleton and naphtholaralkyl resins having a phenylene and/or biphenylene skeleton; be able to.
When using the curing agent (D), only one type may be used, or two or more types may be used in combination.
本実施形態の導電性樹脂組成物は、さらにポリロタキサンを含有するポリマー(E)を含むことができる。 [Polymer (E) containing polyrotaxane]
The conductive resin composition of the present embodiment can further contain a polymer (E) containing polyrotaxane.
封鎖基としては、環状分子の開口より大きな構造を有する基、イオン性の相互作用により環状分子の開口を通過し得ない基などが挙げられる。封鎖基として具体的には、アダマンチル基、シクロデキストリンを含む基、アントラセン基、トリフェニレン基、ピレン基、トリチル基及びこれらの異性体、誘導体などが挙げられる。 The blocking groups in the polyrotaxane are not particularly limited as long as they are groups arranged at both ends of the linear molecular chain and capable of maintaining the state in which the linear molecular chain penetrates the cyclic molecule.
The blocking group includes a group having a structure larger than the opening of the cyclic molecule, a group that cannot pass through the opening of the cyclic molecule due to ionic interaction, and the like. Specific examples of blocking groups include adamantyl groups, groups containing cyclodextrin, anthracene groups, triphenylene groups, pyrene groups, trityl groups, and isomers and derivatives thereof.
ポリロタキサンは、好ましくは架橋性基を有する。ポリロタキサンが架橋性基を有することにより、導電性樹脂組成物の熱硬化性、接着性などが向上する。 In the polyrotaxane, the combination of a cyclic molecule and a linear molecular chain is preferably a combination of α-cyclodextrin or a derivative thereof as the cyclic molecule and a polyethylene glycol chain or derivative thereof as the linear molecular chain. . This combination facilitates movement of the cyclic molecule on the linear molecular chain. In addition, this combination also has the advantage of being relatively easy to synthesize.
The polyrotaxane preferably has crosslinkable groups. By having a crosslinkable group in the polyrotaxane, the thermosetting property, adhesiveness, etc. of the conductive resin composition are improved.
本実施形態の導電性樹脂組成物は、ポリロタキサンを1種のみ含んでもよいし、2種以上含んでもよい。 The polyrotaxane may be synthesized with reference to a known method, or may be a commercially available product. Commercially available products include the "Serum" (registered trademark, SeRM in the alphabet) series sold by ASM Corporation.
The conductive resin composition of the present embodiment may contain only one type of polyrotaxane, or may contain two or more types.
ポリマー(E)中にポリロタキサンを上記の量で含むことにより、熱伝導性および貯蔵弾性率にさらに優れるとともに、基材等との密着性にもより優れる。 In the present embodiment, the content of the polyrotaxane in 100% by mass of the polymer (E) is 75% by mass to 100% by mass, preferably 80% by mass to 100% by mass, more preferably 90% by mass to 100% by mass, especially It is preferably 95% by mass to 100% by mass.
By including the polyrotaxane in the above amount in the polymer (E), the thermal conductivity and the storage elastic modulus are further improved, and the adhesion to the substrate and the like is also further improved.
本実施形態の導電性樹脂組成物は、さらに有機溶剤(F)を含むことができる。
有機溶剤(F)としては、メタノール、エタノール、1-プロパノール、2-プロパノール、1-ブタノール、2-ブタノール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、トリプロピレングリコールモノブチルエーテル、メチルメトキシブタノール、α-ターピネオール、β-ターピネオール、へキシレングリコール、ベンジルアルコール、2-フェニルエチルアルコール、イゾパルミチルアルコール、イソステアリルアルコール、ラウリルアルコール、エチレングリコール、プロピレングリコール、ブチルプロピレントリグリコール、グリセリン等のアルコール類;
アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、ジアセトンアルコール(4-ヒドロキシ-4-メチル-2-ペンタノン)、2-オクタノン、イソホロン(3、5、5-トリメチル-2-シクロヘキセン-1-オン)、ジイソブチルケトン(2、6-ジメチル-4-ヘプタノン)等のケトン類;
酢酸エチル、酢酸ブチル、ジエチルフタレート、ジブチルフタレート、アセトキシエタン、酪酸メチル、ヘキサン酸メチル、オクタン酸メチル、デカン酸メチル、メチルセロソルブアセテート、エチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、1,2-ジアセトキシエタン、リン酸トリブチル、リン酸トリクレジル、リン酸トリペンチル等のエステル類;
テトラヒドロフラン、ジプロピルエーテル、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、プロピレングリコールジメチルエーテル、エトキシエチルエーテル、1,2-ビス(2-ジエトキシ)エタン、1,2-ビス(2-メトキシエトキシ)エタン等のエーテル類;
酢酸2-(2ブトキシエトキシ)エタン等のエステルエーテル類;
2-(2-メトキシエトキシ)エタノール等のエーテルアルコール類;
トルエン、キシレン、n-パラフィン、イソパラフィン、ドデシルベンゼン、テレピン油、ケロシン、軽油等の炭化水素類;
アセトニトリルもしくはプロピオニトリル等のニトリル類;
アセトアミド、N,N-ジメチルホルムアミド等のアミド類;
低分子量の揮発性シリコンオイル、揮発性有機変成シリコンオイル等のシリコンオイル類;
単官能(メタ)アクリル化合物など、を挙げることができる。
有機溶剤(F)を用いる場合、1種のみの溶剤を用いてもよいし、2種以上の溶剤を併用してもよい。 [Organic solvent (F)]
The conductive resin composition of the present embodiment can further contain an organic solvent (F).
Examples of the organic solvent (F) include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, Propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, tripropylene glycol monobutyl ether, methyl methoxybutanol, α-terpineol, β-terpineol, hexylene glycol, benzyl alcohol, 2-phenyl Alcohols such as ethyl alcohol, isopalmityl alcohol, isostearyl alcohol, lauryl alcohol, ethylene glycol, propylene glycol, butylpropylene triglycol, glycerin;
Acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol (4-hydroxy-4-methyl-2-pentanone), 2-octanone, isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), Ketones such as diisobutyl ketone (2,6-dimethyl-4-heptanone);
Ethyl acetate, butyl acetate, diethyl phthalate, dibutyl phthalate, acetoxyethane, methyl butyrate, methyl hexanoate, methyl octanoate, methyl decanoate, methyl cellosolve acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, 1,2- Esters such as diacetoxyethane, tributyl phosphate, tricresyl phosphate, and tripentyl phosphate;
Tetrahydrofuran, dipropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, propylene glycol dimethyl ether, ethoxyethyl ether, 1,2-bis(2-diethoxy)ethane, 1,2-bis(2-methoxyethoxy) ) ethers such as ethane;
Ester ethers such as 2-(2-butoxyethoxy)ethane acetate;
Ether alcohols such as 2-(2-methoxyethoxy)ethanol;
Hydrocarbons such as toluene, xylene, n-paraffin, isoparaffin, dodecylbenzene, turpentine oil, kerosene, light oil;
Nitriles such as acetonitrile or propionitrile;
amides such as acetamide and N,N-dimethylformamide;
Silicone oils such as low molecular weight volatile silicone oils and volatile organically modified silicone oils;
A monofunctional (meth)acrylic compound and the like can be mentioned.
When using the organic solvent (F), only one solvent may be used, or two or more solvents may be used in combination.
本実施形態の導電性樹脂組成物は、さらに硬化促進剤を含むことができる。硬化促進剤は、典型的には多官能エポキシ化合物(C)と硬化剤(D)との反応を促進させるものである。 [Curing accelerator]
The conductive resin composition of this embodiment can further contain a curing accelerator. A curing accelerator typically accelerates the reaction between the polyfunctional epoxy compound (C) and the curing agent (D).
硬化促進剤を用いる場合、1種のみを用いてもよいし、2種以上を併用してもよい。 Specific examples of curing accelerators include phosphorus atom-containing compounds such as imidazole compounds, organic phosphines, tetrasubstituted phosphonium compounds, phosphobetaine compounds, adducts of phosphine compounds and quinone compounds, and adducts of phosphonium compounds and silane compounds; dicyandiamide, 1,8-diazabicyclo[5.4.0]undecene-7, amidines and tertiary amines such as benzyldimethylamine; nitrogen atom-containing compounds such as quaternary ammonium salts of the above amidines or the above tertiary amines; be done.
When using a hardening accelerator, only 1 type may be used and 2 or more types may be used together.
本実施形態の導電性樹脂組成物は、さらに硬化促進剤を含むことができる。ラジカル重合開始剤により、例えば、硬化が不十分となることを抑えることができたり、比較的低温(例えば180℃)での硬化反応を十分に進行させることができたり、接着力を一層向上させることができたりする場合がある。
ラジカル重合開始剤としては、過酸化物、アゾ化合物などを挙げることができる。 [Radical polymerization initiator]
The conductive resin composition of this embodiment can further contain a curing accelerator. The radical polymerization initiator can, for example, prevent insufficient curing, allow the curing reaction to proceed sufficiently at a relatively low temperature (eg, 180° C.), or further improve the adhesive strength. sometimes it can be done.
Examples of radical polymerization initiators include peroxides and azo compounds.
p-メンタンハイドロパーオキサイド、ジイソプロピルベンゼ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、クメンハイドロパーオキサイド、t-ブチルハイドロパーオキサイド等のハイドロパーオキサイド;
ジ(2-t-ブチルパーオキシイソプロピル)ベンゼン、ジクミルパーオキサイド、2,5-ジメチル-2,5-ジ(t-ブチルパーオキシ)ヘキサン、t-ブチルクミルパーオキサイド、ジ-t-へキシルパーオキサイド、2,5-ジメチル-2,5-ジ(t-ブチルパーオキシ)ヘキシン-3、ジ-t-ブチルパーオキサイド等のジアルキルパーオキサイド;
ジベンゾイルパーオキサイド、ジ(4-メチルベンゾイル)パーオキサイド等のジアシルパーオキサイド;
ジ-n-プロピルパーオキシジカーボネート、ジイソプロピルパーオキシジカーボネート等のパーオキシジカーボネート;
2,5-ジメチル-2,5-ジ(ベンゾイルパーオキシ)ヘキサン、t-へキシルパーオキシベンゾエート、t-ブチルパーオキシベンゾエート、t-ブチルパーオキシ2-エチルヘキサノネート等のパーオキシエステルなどを挙げることができる。 Examples of peroxides include organic peroxides such as diacyl peroxide, dialkyl peroxide, and peroxyketals, more specifically, ketone peroxides such as methyl ethyl ketone peroxide and cyclohexanone peroxide; Peroxyketals such as 1,1-di(t-butylperoxy)cyclohexane and 2,2-di(4,4-di(t-butylperoxy)cyclohexyl)propane;
Hydroperoxides such as p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-butyl hydroperoxide;
di(2-t-butylperoxyisopropyl)benzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, t-butylcumyl peroxide, di-t- Dialkyl peroxides such as xyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3, di-t-butyl peroxide;
Diacyl peroxides such as dibenzoyl peroxide and di(4-methylbenzoyl) peroxide;
Peroxydicarbonates such as di-n-propyl peroxydicarbonate and diisopropyl peroxydicarbonate;
Peroxyesters such as 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, t-hexylperoxybenzoate, t-butylperoxybenzoate, t-butylperoxy 2-ethylhexanonate, etc. can be mentioned.
ラジカル重合開始剤を用いる場合、1種のみを用いてもよいし、2種以上を併用してもよい。 Azo compounds include 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2, 4-dimethylvaleronitrile) and the like.
When using a radical polymerization initiator, only one type may be used, or two or more types may be used in combination.
本実施形態の導電性樹脂組成物は、その他の成分として、硬化促進剤、シランカップリング剤、可塑剤、密着性付与剤等を含むことができる。 [Other ingredients]
The conductive resin composition of the present embodiment can contain other components such as a curing accelerator, a silane coupling agent, a plasticizer, and an adhesion imparting agent.
本実施形態の導電性樹脂組成物は、好ましくは、20℃でペースト状である。すなわち、本実施形態の導電性樹脂組成物(ペースト状組成物)は、好ましくは、20℃で、糊のようにして基板等に塗布することができる。このことにより、本実施形態の導電性樹脂組成物を、半導体素子の接着剤などとして好ましく用いることができる。
もちろん、適用されるプロセスなどによっては、本実施形態の導電性樹脂組成物は、比較的低粘度のワニス状などであってもよい。
本実施形態の導電性樹脂組成物は、上述の各成分と、必要に応じてその他の成分とを、従来公知の方法で混合することにより得ることができる。 <Conductive resin composition>
The conductive resin composition of the present embodiment is preferably pasty at 20°C. That is, the conductive resin composition (paste composition) of the present embodiment can preferably be applied to a substrate or the like like a paste at 20°C. As a result, the conductive resin composition of the present embodiment can be preferably used as an adhesive for semiconductor elements or the like.
Of course, depending on the applied process, the conductive resin composition of the present embodiment may be in the form of a relatively low-viscosity varnish.
The conductive resin composition of the present embodiment can be obtained by mixing each of the components described above and, if necessary, other components by a conventionally known method.
本実施形態の導電性樹脂組成物を焼結することにより高熱伝導性材料を得ることができる。
高熱伝導性材料の形状を変えることにより、自動車、電機分野において熱放散性を必要とする様々な部品に適用することができる。 <High thermal conductivity material>
A highly thermally conductive material can be obtained by sintering the conductive resin composition of the present embodiment.
By changing the shape of the high thermal conductivity material, it can be applied to various parts that require heat dissipation in the fields of automobiles and electrical machinery.
本実施形態の導電性樹脂組成物を用いて、半導体装置を製造することができる。例えば、本実施形態の導電性樹脂組成物を、基材と半導体素子との「接着剤」として用いることで、半導体装置を製造することができる。 <Semiconductor device>
A semiconductor device can be manufactured using the conductive resin composition of the present embodiment. For example, a semiconductor device can be manufactured by using the conductive resin composition of the present embodiment as an "adhesive" between a substrate and a semiconductor element.
半導体素子としては、IC、LSI、電力用半導体素子(パワー半導体)、その他各種の素子を挙げることができる。
基板としては、各種半導体ウエハ、リードフレーム、BGA基板、実装基板、ヒートスプレッダー、ヒートシンクなどを挙げることができる。 In the semiconductor device of the present embodiment, the stress is relaxed, and the adhesiveness of the adhesive layer is less likely to deteriorate due to heat cycles. That is, the reliability of the semiconductor device of this embodiment is high.
Examples of semiconductor devices include ICs, LSIs, power semiconductor devices (power semiconductors), and various other devices.
Examples of substrates include various semiconductor wafers, lead frames, BGA substrates, mounting substrates, heat spreaders, and heat sinks.
図1は、半導体装置の一例を示す断面図である。
半導体装置100は、基材30と、導電性樹脂組成物の熱処理体である接着層10(ダイアタッチ材)を介して基材30上に搭載された半導体素子20と、を備える。 An example of a semiconductor device will be described below with reference to the drawings.
FIG. 1 is a cross-sectional view showing an example of a semiconductor device.
The
接着層10の厚さは、例えば100μm以下、好ましくは50μm以下である。 The thickness of the
The thickness of the
基材30の表面は、例えば、銀、金などの金属により被膜されていてもよい。これにより、接着層10と基材30との接着性が向上する。 The
The surface of the
図2の半導体装置100において、基材30は、例えばインターポーザである。インターポーザである基材30のうち、半導体素子20が搭載される一面と反対側の面には、例えば複数の半田ボール52が形成される。この場合、半導体装置100は、半田ボール52を介して他の配線基板へ接続されることとなる。 FIG. 2 is a cross-sectional view showing another example of the
In the
まず、基材30の上に、導電性樹脂組成物を塗工し、次いで、その上に半導体素子20を配置する。すなわち、基材30、導電性樹脂組成物、半導体素子20がこの順で積層される。
導電性樹脂組成物を塗工する方法は特に限定されない。具体的には、ディスペンシング、印刷法、インクジェット法などを挙げることができる。 An example of a method for manufacturing a semiconductor device will be described.
First, the
The method of applying the conductive resin composition is not particularly limited. Specifically, a dispensing method, a printing method, an inkjet method, and the like can be mentioned.
実施例で用いた成分を以下に示す。 EXAMPLES The present invention will be described in more detail below with reference to Examples, but the present invention is not limited to these.
Components used in the examples are shown below.
・脂肪族多官能エポキシ化合物1:トリメチロールプロパンポリグリシジルエーテル(下記化学式で表される化合物の混合物、デナコールEX-321L、ナガセケムテック社製)
Aliphatic polyfunctional epoxy compound 1: trimethylolpropane polyglycidyl ether (a mixture of compounds represented by the following chemical formula, Denacol EX-321L, manufactured by Nagase Chemtech)
・エポキシ樹脂5:アミノフェノール型エポキシ樹脂(三菱ケミカル社製、jER630) ・ Epoxy resin 4: bisphenol F type epoxy resin (manufactured by Nippon Kayaku, RE-303S)
・ Epoxy resin 5: aminophenol type epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER630)
・アクリルモノマー1:エチレングリコールジメタクリレート(共栄社化学社製、ライトエステルEG)
・アクリルモノマー2:1,4-シクロヘキサンジメタノールモノアクリレート(日本化成社製、CHDMMA、単官能アクリル) ((meth)acrylic compound)
・ Acrylic monomer 1: ethylene glycol dimethacrylate (manufactured by Kyoeisha Chemical Co., Ltd., Light Ester EG)
・Acrylic monomer 2: 1,4-cyclohexanedimethanol monoacrylate (manufactured by Nippon Kasei Co., Ltd., CHDMMA, monofunctional acrylic)
・硬化剤1:ビスフェノールF骨格を有するフェノール樹脂(DIC社製、DIC-BPF) (curing agent)
・ Curing agent 1: Phenolic resin having a bisphenol F skeleton (DIC-BPF manufactured by DIC)
・ラジカル重合開始剤1:ジクミルパーオキサイド(化薬アクゾ社製、パーカドックスBC) (Radical polymerization initiator)
- Radical polymerization initiator 1: Dicumyl peroxide (manufactured by Kayaku Akzo Co., Ltd., Perkadox BC)
・硬化促進剤1:2-フェニル-1H-イミダゾール-4,5-ジメタノール(四国化成工業社製、2PHZ-PW) (Curing accelerator)
・ Curing accelerator 1: 2-phenyl-1H-imidazole-4,5-dimethanol (manufactured by Shikoku Kasei Kogyo Co., Ltd., 2PHZ-PW)
・銀フィラー1:DOWAエレクトロニクス社製、AG-DSB-114、球状、D50:0.7μm、比表面積:1.05m2/g、タップ密度5.25g/cm3、円形度:0.953
・銀フィラー2:福田金属箔粉工業社製、HKD-12、鱗片状、メジアン径D50:7.6μm、比表面積:0.315m2/g、タップ密度:5.5g/cm3 (Silver-containing particles)
・Silver filler 1: Dowa Electronics Co., Ltd., AG-DSB-114, spherical, D 50 : 0.7 μm, specific surface area: 1.05 m 2 /g, tap density 5.25 g/cm 3 , circularity: 0.953
・Silver filler 2: HKD-12 manufactured by Fukuda Metal Foil & Powder Co., Ltd., scale-like, median diameter D 50 : 7.6 μm, specific surface area: 0.315 m 2 /g, tap density: 5.5 g/cm 3
・溶剤1:トリプロピレングリコールモノ-n-ブチルエーテル(BFTG、日本乳化剤社製、沸点274℃) (solvent)
・ Solvent 1: Tripropylene glycol mono-n-butyl ether (BFTG, manufactured by Nippon Emulsifier Co., Ltd., boiling point 274 ° C.)
表1に示される配合量に従って、各原料成分を混合し、ワニスを得た。
次に、得られたワニスを用い、表1に示す配合量に従って配合し、常温で、3本ロールミルで混練した。これにより、導電性樹脂組成物を作製した。 [Examples 1-8, Comparative Examples 1-2]
Each raw material component was mixed according to the compounding amount shown in Table 1 to obtain a varnish.
Next, the obtained varnish was blended according to the blending amounts shown in Table 1, and kneaded at room temperature in a three-roll mill. Thus, a conductive resin composition was produced.
導電性樹脂組成物をガラス板上に塗布し、窒素雰囲気下で、30℃から200℃まで60分間かけて昇温し、続けて200℃で120分間熱処理した。これにより、厚さ0.05mmの導電性樹脂組成物の熱処理体(硬化物)を得た。ミリオームメータ(HIOKI社製)による直流四電極法、電極間隔が40mmの電極を用い、熱処理体表面の抵抗値を測定した。 (volume resistivity)
The conductive resin composition was applied onto a glass plate, heated from 30° C. to 200° C. over 60 minutes in a nitrogen atmosphere, and then heat-treated at 200° C. for 120 minutes. As a result, a heat-treated body (cured product) of the conductive resin composition having a thickness of 0.05 mm was obtained. The resistance value of the surface of the heat-treated body was measured using a direct current four-electrode method with a milliohmmeter (manufactured by Hioki Co., Ltd.) and electrodes with an electrode spacing of 40 mm.
AgメッキされたCuリードフレームのAgメッキ上に、得られた導電性樹脂組成物を所定量塗布し、その上に5×7mm角の裏面AuコートされたチップをAuコート面が接するようにマウントし、窒素雰囲気下において200℃で2時間硬化させ、評価用半導体装置を作製した。得られた半導体装置を温度60℃、湿度60%下で48時間処理した後の剥離有無を超音波探傷試験機(SAT)にて評価した。剥離が確認されてものを×、剥離がなかったものを〇とした。 (Evaluation of peeling after constant temperature moisture absorption treatment)
A predetermined amount of the obtained conductive resin composition was applied onto the Ag plating of the Ag-plated Cu lead frame, and a 5×7 mm square chip whose rear surface was Au-coated was mounted thereon so that the Au-coated surface was in contact. Then, it was cured at 200° C. for 2 hours in a nitrogen atmosphere to fabricate a semiconductor device for evaluation. The resulting semiconductor device was treated at a temperature of 60° C. and a humidity of 60% for 48 hours, and the presence or absence of peeling was evaluated using an ultrasonic tester (SAT). When peeling was confirmed, it was evaluated as x, and when there was no peeling, it was evaluated as ◯.
上記で作製した評価用半導体装置を上記と同様に温度60℃、湿度60%下で48時間処理して評価用サンプルとした。チップ密着強度について、4000万能型ボンドテスター(Nordson Dage社製)を用いて、260℃加熱時にリードフレームからの高さ50μmの位置をツール速度500μm/sでシェアをかけた際の強度をチップ密着強度として評価した。 (Adhesion strength after constant temperature moisture absorption treatment)
The semiconductor device for evaluation produced as described above was treated in the same manner as described above at a temperature of 60° C. and a humidity of 60% for 48 hours to obtain an evaluation sample. Regarding the chip adhesion strength, using a 4000 universal bond tester (manufactured by Nordson Dage), the strength when shearing at a tool speed of 500 μm / s at a position of 50 μm in height from the lead frame when heating at 260 ° C. It was evaluated as strength.
10 接着層
20 半導体素子
30 基材
32 ダイパッド
34 アウターリード
40 ボンディングワイヤ
50 封止樹脂
52 半田ボール 100
Claims (11)
- (A)銀含有粒子と、
(B)(メタ)アクリル化合物と、
(C)下記一般式(1)で表される化合物から選択される少なくとも1種の多官能エポキシ化合物と、
を含む、導電性樹脂組成物。
Qは、2~6価の有機基を示す。
Xは炭素数1~3のアルキレン基を示し、複数存在するXは同一でも異なっていてもよい。
mは0~2の整数、nは2~4の整数を示す。) (A) silver-containing particles;
(B) a (meth) acrylic compound;
(C) at least one polyfunctional epoxy compound selected from compounds represented by the following general formula (1);
A conductive resin composition comprising:
Q represents a divalent to hexavalent organic group.
X represents an alkylene group having 1 to 3 carbon atoms, and multiple X's may be the same or different.
m is an integer of 0-2, n is an integer of 2-4. ) - 多官能エポキシ化合物(C)は、一般式(1)中の前記Qが一般式(a)~(h)で表される有機基である化合物から選択される少なくとも1種を含む、請求項1に記載の導電性樹脂組成物。
一般式(f)中、Q1およびQ2は炭素数1~3のアルキレン基または炭素数3~8のシクロアルキレン基を示し、R1およびR2は炭素数1~3のアルキレン基を示す。
一般式(a)~(h)中、*は結合手を示す。) Claim 1, wherein the polyfunctional epoxy compound (C) contains at least one compound selected from compounds in which the Q in the general formula (1) is an organic group represented by general formulas (a) to (h). Conductive resin composition according to.
In general formula (f), Q 1 and Q 2 represent an alkylene group having 1 to 3 carbon atoms or a cycloalkylene group having 3 to 8 carbon atoms, and R 1 and R 2 represent an alkylene group having 1 to 3 carbon atoms. .
In general formulas (a) to (h), * indicates a bond. ) - 多官能エポキシ化合物(C)は、前記Qが一般式(a)、(b)および(c)で表される有機基である化合物から選択される少なくとも1種を含む、請求項1または2に記載の導電性樹脂組成物。 3. The polyfunctional epoxy compound (C) according to claim 1 or 2, comprising at least one compound selected from compounds in which said Q is an organic group represented by general formulas (a), (b) and (c). The conductive resin composition described.
- 多官能エポキシ化合物(C)は、前記Qが一般式(a)および(b)で表される有機基である化合物から選択される少なくとも1種を含む、請求項1~3のいずれかに記載の導電性樹脂組成物。 4. The polyfunctional epoxy compound (C) according to any one of claims 1 to 3, comprising at least one compound selected from compounds in which said Q is an organic group represented by general formulas (a) and (b). The conductive resin composition of.
- 多官能エポキシ化合物(C)100質量部に対して、(メタ)アクリル化合物(B)を10~85質量部含む、請求項1~4のいずれかに記載の導電性樹脂組成物。 The conductive resin composition according to any one of claims 1 to 4, comprising 10 to 85 parts by mass of the (meth)acrylic compound (B) with respect to 100 parts by mass of the polyfunctional epoxy compound (C).
- 銀含有粒子(A)が球状、樹状、紐状、鱗片状、凝集状、および多面体形状の銀含有粒子から選択される2種以上を含む、請求項1~5のいずれかに記載の導電性樹脂組成物。 The conductive material according to any one of claims 1 to 5, wherein the silver-containing particles (A) include two or more selected from spherical, dendritic, string-like, scaly, aggregated, and polyhedral silver-containing particles. elastic resin composition.
- さらに、硬化剤(D)を含む、請求項1~6のいずれかに記載の導電性樹脂組成物。 The conductive resin composition according to any one of claims 1 to 6, further comprising a curing agent (D).
- さらに、ポリロタキサンを含むポリマー(E)を含む、請求項1~7のいずれかに記載の導電性樹脂組成物。 The conductive resin composition according to any one of claims 1 to 7, further comprising a polymer (E) containing polyrotaxane.
- さらに、有機溶剤(F)を含む、請求項1~8のいずれかに記載の導電性樹脂組成物。 The conductive resin composition according to any one of claims 1 to 8, further comprising an organic solvent (F).
- 請求項1~9のいずれかに記載の導電性樹脂組成物を焼結して得られる高熱伝導性材料。 A highly thermally conductive material obtained by sintering the conductive resin composition according to any one of claims 1 to 9.
- 基材と、
前記基材上に接着層を介して搭載された半導体素子と、を備え、
前記接着層は、請求項1~9のいずれかに記載の導電性樹脂組成物を焼結してなる、半導体装置。 a substrate;
A semiconductor element mounted on the base material via an adhesive layer,
A semiconductor device, wherein the adhesive layer is formed by sintering the conductive resin composition according to any one of claims 1 to 9.
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Citations (6)
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JPH05501783A (en) * | 1989-11-29 | 1993-04-02 | アチソン・インダストリーズ・インコーポレイテツド | Conductive adhesive useful for bonding semiconductor die to a conductive support base |
JP2004168922A (en) * | 2002-11-21 | 2004-06-17 | Sumitomo Bakelite Co Ltd | Die attach paste and semiconductor device |
JP2008007558A (en) * | 2006-06-27 | 2008-01-17 | Sumitomo Bakelite Co Ltd | Liquid resin composition and semiconductor device prepared using the same |
JP2015160932A (en) * | 2014-02-28 | 2015-09-07 | 昭和電工株式会社 | Conductive adhesive and electronic device using the same |
JP2016222804A (en) * | 2015-05-29 | 2016-12-28 | 株式会社タムラ製作所 | Conductive adhesive and electronic substrate |
WO2022030089A1 (en) * | 2020-08-04 | 2022-02-10 | ナミックス株式会社 | Conductive composition, die attachment material, pressure-sintered die attachement material, and electronic component |
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JP5806760B1 (en) | 2014-05-29 | 2015-11-10 | 田中貴金属工業株式会社 | Thermally conductive conductive adhesive composition |
CN110709487B (en) | 2017-06-07 | 2022-01-14 | 田中贵金属工业株式会社 | Thermally and electrically conductive adhesive composition |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPH05501783A (en) * | 1989-11-29 | 1993-04-02 | アチソン・インダストリーズ・インコーポレイテツド | Conductive adhesive useful for bonding semiconductor die to a conductive support base |
JP2004168922A (en) * | 2002-11-21 | 2004-06-17 | Sumitomo Bakelite Co Ltd | Die attach paste and semiconductor device |
JP2008007558A (en) * | 2006-06-27 | 2008-01-17 | Sumitomo Bakelite Co Ltd | Liquid resin composition and semiconductor device prepared using the same |
JP2015160932A (en) * | 2014-02-28 | 2015-09-07 | 昭和電工株式会社 | Conductive adhesive and electronic device using the same |
JP2016222804A (en) * | 2015-05-29 | 2016-12-28 | 株式会社タムラ製作所 | Conductive adhesive and electronic substrate |
WO2022030089A1 (en) * | 2020-08-04 | 2022-02-10 | ナミックス株式会社 | Conductive composition, die attachment material, pressure-sintered die attachement material, and electronic component |
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