JP2009209246A - 樹脂組成物、接着剤層、及びそれらを用いて作製した半導体装置 - Google Patents
樹脂組成物、接着剤層、及びそれらを用いて作製した半導体装置 Download PDFInfo
- Publication number
- JP2009209246A JP2009209246A JP2008052849A JP2008052849A JP2009209246A JP 2009209246 A JP2009209246 A JP 2009209246A JP 2008052849 A JP2008052849 A JP 2008052849A JP 2008052849 A JP2008052849 A JP 2008052849A JP 2009209246 A JP2009209246 A JP 2009209246A
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- Prior art keywords
- compound
- meth
- resin composition
- acrylate
- bis
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 239000004065 semiconductor Substances 0.000 title claims abstract description 38
- 239000012790 adhesive layer Substances 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 36
- 230000001070 adhesive effect Effects 0.000 claims abstract description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 239000002245 particle Substances 0.000 claims abstract description 21
- 239000000853 adhesive Substances 0.000 claims abstract description 15
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 230000017525 heat dissipation Effects 0.000 claims description 10
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 claims description 8
- PDHFSBXFZGYBIP-UHFFFAOYSA-N 2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethanol Chemical compound OCCSCCSCCO PDHFSBXFZGYBIP-UHFFFAOYSA-N 0.000 claims description 4
- VZYIKHZFVOUXKE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethylsulfanyl]ethanol Chemical compound OCCSCCSCCSCCO VZYIKHZFVOUXKE-UHFFFAOYSA-N 0.000 claims description 4
- OPXVPMORRICVSM-UHFFFAOYSA-N 2-ethylsulfanylethane-1,1-diol Chemical compound CCSCC(O)O OPXVPMORRICVSM-UHFFFAOYSA-N 0.000 claims description 4
- 238000013329 compounding Methods 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 32
- 229910052802 copper Inorganic materials 0.000 abstract description 32
- 239000010949 copper Substances 0.000 abstract description 32
- 239000011248 coating agent Substances 0.000 abstract description 15
- 238000000576 coating method Methods 0.000 abstract description 15
- 238000000926 separation method Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 79
- -1 4-cyanatophenyl Chemical group 0.000 description 57
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 28
- 229910052709 silver Inorganic materials 0.000 description 20
- 239000004332 silver Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 238000007747 plating Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 150000003568 thioethers Chemical class 0.000 description 11
- 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 10
- 238000001723 curing Methods 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
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- 239000000843 powder Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 229920003986 novolac Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 2
- ZHMUMDLGQBRJIW-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ZHMUMDLGQBRJIW-UHFFFAOYSA-N 0.000 description 2
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
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- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 2
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- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
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- GSYVJAOBRKCNOT-UHFFFAOYSA-N diethoxymethyl-[3-[3-(diethoxymethylsilyl)propyltetrasulfanyl]propyl]silane Chemical compound CCOC(OCC)[SiH2]CCCSSSSCCC[SiH2]C(OCC)OCC GSYVJAOBRKCNOT-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- RLYFOKIGLVMCFH-UHFFFAOYSA-N dimethoxymethyl-[3-[3-(dimethoxymethylsilyl)propyltetrasulfanyl]propyl]silane Chemical compound COC(OC)[SiH2]CCCSSSSCCC[SiH2]C(OC)OC RLYFOKIGLVMCFH-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
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- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
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- 238000013007 heat curing Methods 0.000 description 1
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- CTRFEEQNDJFNNL-UHFFFAOYSA-N hexanoic acid;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.CCCCCC(O)=O CTRFEEQNDJFNNL-UHFFFAOYSA-N 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
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- MOFOBJHOKRNACT-UHFFFAOYSA-N nickel silver Chemical compound [Ni].[Ag] MOFOBJHOKRNACT-UHFFFAOYSA-N 0.000 description 1
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical group OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- BSWGGJHLVUUXTL-UHFFFAOYSA-N silver zinc Chemical compound [Zn].[Ag] BSWGGJHLVUUXTL-UHFFFAOYSA-N 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical class [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- JUAHKSBERRLSHD-UHFFFAOYSA-N tetraphenyl-$l^{5}-phosphane Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JUAHKSBERRLSHD-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- ATYIZISYPACGCO-UHFFFAOYSA-N tributoxy-[3-(3-tributoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCSSCCC[Si](OCCCC)(OCCCC)OCCCC ATYIZISYPACGCO-UHFFFAOYSA-N 0.000 description 1
- VVKKLYJRUIYBJT-UHFFFAOYSA-N tributoxy-[3-(3-tributoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCSSSSCCC[Si](OCCCC)(OCCCC)OCCCC VVKKLYJRUIYBJT-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- NQRACKNXKKOCJY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSCCC[Si](OC)(OC)OC NQRACKNXKKOCJY-UHFFFAOYSA-N 0.000 description 1
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
- H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
- H01L2224/29001—Core members of the layer connector
- H01L2224/29099—Material
- H01L2224/29198—Material with a principal constituent of the material being a combination of two or more materials in the form of a matrix with a filler, i.e. being a hybrid material, e.g. segmented structures, foams
- H01L2224/29298—Fillers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/00011—Not relevant to the scope of the group, the symbol of which is combined with the symbol of this group
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/00013—Fully indexed content
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01005—Boron [B]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01006—Carbon [C]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01029—Copper [Cu]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/102—Material of the semiconductor or solid state bodies
- H01L2924/1025—Semiconducting materials
- H01L2924/10251—Elemental semiconductors, i.e. Group IV
- H01L2924/10253—Silicon [Si]
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Die Bonding (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
Abstract
【解決手段】導電性粒子(A)、熱硬化性樹脂(B)、スルフィド結合を有する化合物がスルフィド結合とアルコキシシリル基を有する化合物(C1)、及びスルフィド結合と水酸基を有する化合物(C2)を含むことを特徴とする樹脂組成物、接着剤層、並びに該樹脂組成物を使用して作製したことを特徴とする半導体装置である。
【選択図】 なし
Description
これらの場合に半導体素子を接着する材料は熱伝導率だけでなく各界面において良好な塗布作業性が求められ、ボイド、剥離など熱拡散を悪化させる要因は排除される必要がある。
前記化合物(C2)は、芳香族環を含まない化合物であることができる。
前記化合物(C2)は、2,2'−ジチオジエタノール、3−チアペンタンジオール、3,6−ジチアオクタン−1,8−ジオール、及び3,6,9−トリチアウンデカン−1,11−ジオールからなる群より選ばれる少なくとも1つ以上の化合物であることができる。
前記化合物(C1)と前記化合物(C2)の配合比は (C1)/(C2)=1/9〜9/1であることができる。
本発明の接着剤層は、前述の樹脂組成物を加熱することにより得られることを特徴とする。
本発明の半導体装置は、前述の樹脂組成物を半導体用ダイアタッチペーストまたは放熱部材接着用材料として用いて作製したことを特徴とする。
本発明の接着剤層は、該樹脂組成物を加熱することにより得られるものであって、高温リフロー処理後でも剥離が生じない高信頼性のものである。
本発明の半導体装置は、該樹脂組成物を半導体用ダイアタッチペーストまたは放熱部材接着用材料として用いて作製したものであって、高温リフロー処理後でも剥離の生じない高信頼性のものである。
以下、本発明について詳細に説明する。
熱伝導性の向上の観点から特に好ましい導電性粒子(A)は銀粉である。ここで銀粉とは純銀又は銀合金の粉末であり、銀合金としては銀を50重量%以上、好ましくは70重量%以上含有する銀−銅合金、銀−パラジウム合金、銀−錫合金、銀−亜鉛合金、銀−マグネシウム合金、銀−ニッケル合金などである。銀粉が好ましいのは良好な導電性、熱伝導性を有する上に酸化されにくく加工性にも優れるからである。
ジヒドラジド化合物としては、アジピン酸ジヒドラジド、ドデカン酸ジヒドラジド、イソフタル酸ジヒドラジド、p−オキシ安息香酸ジヒドラジドなどのカルボン酸ジヒドラジドなどが挙げられ、酸無水物としてはフタル酸無水物、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、エンドメチレンテトラヒドロフタル酸無水物、ドデセニルコハク酸無水物、無水マレイン酸とポリブタジエンの反応物、無水マレイン酸とスチレンの共重合体などが挙げられる。
特に好ましいアクリル樹脂は分子量が500〜10000のポリエーテル、ポリエステル、ポリカーボネート、ポリ(メタ)アクリレート、ポリブタジエン、ブタジエンアクリロニトリル共重合体で(メタ)アクリル基を有する化合物である。
ポリエーテルとしては、炭素数が3〜6の有機基がエーテル結合を介して繰り返したものが好ましく、芳香族環を含まないものが好ましい。ポリエーテルポリオールと(メタ)アクリル酸またはその誘導体との反応により得ることが可能である。
ポリエステルとしては、炭素数が3〜6の有機基がエステル結合を介して繰り返したものが好ましく、芳香族環を含まないものが好ましい。ポリエステルポリオールと(メタ)アクリル酸またはその誘導体との反応により得ることが可能である。ポリカーボネートとしては、炭素数が3〜6の有機基がカーボネート結合を介して繰り返したものが好ましく、芳香族環を含まないものが好ましい。ポリカーボネートポリオールと(メタ)アクリル酸またはその誘導体との反応により得ることが可能である。
ポリブタジエンとしては、カルボキシ基を有するポリブタジエンと水酸基を有する(メタ)アクリレートとの反応、水酸基を有するポリブタジエンと(メタ)アクリル酸またはその誘導体との反応により得ることが可能であり、また無水マレイン酸を付加したポリブタジエンと水酸基を有する(メタ)アクリレートとの反応により得ることも可能である。
ブタジエンアクリロニトリル共重合体としては、カルボキシ基を有するブタジエンアクリロニトリル共重合体と水酸基を有する(メタ)アクリレートとの反応により得ることが可能である。
例えば化合物(C1)は金属表面との密着力向上効果があることは公知であり、被着体が銀メッキ表面の場合、Ni−Pdメッキ表面の場合には良好な接着力を示すようになるが、被着体表面が銅の場合には接着力は向上するものの、その効果は十分ではなく、さらに銅表面への接着力を向上させるとトレードオフとして銀メッキ表面との接着力が低下するなど、銅表面への接着力と銀メッキ表面への接着力の両立は困難であった。
ここで化合物(C1)と化合物(C2)を併用することで化合物(C1)の特徴である銀メッキ表面への高接着特性を維持しつつ、銅表面への接着力を大幅に向上させることが可能となり、被着体が銅表面の場合でも、銀メッキ表面の場合と同様に信頼性の高い接着剤層を得ることが可能となった。
化合物(C1)は少なくとも1つのアルコキシシリル基を有するが、より好ましいのはアルコキシシリル基が2つの場合である。このような化合物としてはビス(トリメトキシシリルプロピル)テトラスルフィド、ビス(トリエトキシシリルプロピル)テトラスルフィド、ビス(トリブトキシシリルプロピル)テトラスルフィド、ビス(ジメトキシメチルシリルプロピル)テトラスルフィド、ビス(ジエトキシメチルシリルプロピル)テトラスルフィド、ビス(ジブトキシメチルシリルプロピル)テトラスルフィド、ビス(トリメトキシシリルプロピル)ジスルフィド、ビス(トリエトキシシリルプロピル)ジスルフィド、ビス(トリブトキシシリルプロピル)ジスルフィド、ビス(ジメトキシメチルシリルプロピル)ジスルフィド、ビス(ジエトキシメチルシリルプロピル)ジスルフィド、ビス(ジブトキシメチルシリルプロピル)ジスルフィドなどが挙げられる。これら化合物はスルフィド結合の繰り返し数に分布があり、例えばビス(トリメトキシシリルプロピル)テトラスルフィドとは高速液体クロマトグラムなどにて測定して得られた平均スルフィド結合数が約4の化合物である。
また、この芳香族環を含まない化合物のなかでも特に好ましいものはスルフィド結合と水酸基を2個有する化合物であり、具体的には2,2’−ジチオジエタノール、3−チアペンタンジオール、3,6−ジチアオクタン−1,8−ジオール、及び3,6,9−トリチアウンデカン−1,11−ジオールからなる群より選ばれる少なくとも1つ以上の化合物である。これらの化合物を採用することでさらに銅表面への接着特性が良好になる。
このとき接着剤層の厚みについてはとくに制限を受けるものではないが、塗布作業性、及び銀メッキ表面に対する接着特性と銅表面に対する接着特性とのバランスを考慮すると、5μm以上、100μm以下、好ましくは10μm以上、50μm以下であるのが望ましい。特に好ましいのは10μm以上、30μm以下である。下限値未満では接着特性が悪化する場合があり、上限値を超えるとでは接着剤層の厚み制御が困難になり銀メッキ表面に対する接着特性と銅表面に対する接着特性とのバランスが安定しない場合があるからである。
[実施例1]
導電性粒子(A)として平均粒径8μm、最大粒径30μmのフレーク状銀粉(以下銀粉)を、熱硬化性樹脂(B)としてポリテトラメチレングリコールとイソホロンジイソシアネートと2−ヒドロキシメチルメタクリレートとの反応により得られたウレタンジメタクリレート化合物(分子量約1600、以下化合物B1)、1,4−シクロヘキサンジメタノールモノアクリレート(日本化成(株)製、CHDMMA、以下化合物B6)、2−メタクリロイルオキシエチルコハク酸(共栄社化学(株)製、ライトエステルHO−MS、以下化合物B7)、1,6−ヘキサンジオールジメタクリレート(共栄社化学(株)製、ライトエステル1,6HX、以下化合物B8)、ジクミルパーオキサイド(日本油脂(株)製、パークミルD、急速加熱試験における分解温度:126℃、以下重合開始剤)を、スルフィド結合とアルコキシシリル基を有する化合物(C1)としてビス(トリエトキシシリルプロピル)テトラスルフィド(ダイソー(株)製、カブラス4、以下化合物C11)を、スルフィド結合と水酸基を有する化合物(C2)として3,6−ジチアオクタン−1,8−ジオール(試薬、以下化合物C21)を、3−グリシジルプロピルトリメトキシシラン(信越化学工業(株)製、KBM−403E、以下化合物Z1)を表1のように配合し、3本ロールを用いて混練し、脱泡することで樹脂組成物を得た。配合割合は重量部である。得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
以下の化合物を使用した。
ポリテトラメチレングリコールとマレイミド化酢酸の反応により得られたビスマレイミド化合物(分子量580、以下化合物B2)、シクロヘキサンジカルボン酸のジアリルエステルとポリプロピレングリコールとの反応により得られたジアリルエステル化合物(分子量1000、ただし原料として用いたシクロヘキサンジカルボン酸のジアリルエステルを約15%含む、以下化合物B3)、1,4−シクロヘキサンジメタノール/1,6−ヘキサンジオール(=3/1(重量比))と炭酸ジメチルの反応により得られたポリカーボネートジオールとメチルメタクリレートの反応により得られたポリカーボネートジメタクリレート化合物(分子量1000、以下化合物B4)、酸価108mgKOH/gで分子量4600のアクリルオリゴマーと2−ヒドロキシメタクリレート/ブチルアルコール(=1/2(モル比))との反応により得られたメタクリル化アクリルオリゴマー(分子量5000、以下化合物B5)、ビスフェノールAとエピクロルヒドリンとの反応により得られるジグリシジルビスフェノールA(エポキシ当量180、常温で液体、以下化合物B9)、クレジルグリシジルエーテル(エポキシ当量185、以下化合物B10)、ビスフェノールF(大日本インキ工業(株)製、DIC−BPF、水酸基当量100、以下化合物B11)、ジシアンジアミド(以下化合物B12)、2−メチルイミダゾールと2,4−ジアミノ−6−ビニルトリアジンとの付加物(四国化成工業(株)製、キュアゾール2MZ−A、以下化合物B13)、化合物(C1)としてビス(トリエトキシシリルプロピル)ジスルフィド(ダイソー(株)製、カブラス2A、以下化合物C12)、化合物(C2)として3,6,9−トリチアウンデカン−1,11−ジオール(試薬、以下化合物C22)。
これらの中から選択した化合物を表1のように配合し、実施例1と同様に3本ロールを用いて混練し、脱泡することで樹脂組成物を得た。配合割合は重量部である。得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
表1に示す割合で配合し実施例1と同様に樹脂組成物を得た。
得られた樹脂組成物を以下の方法により評価した。評価結果を表1に示す。
・塗布作業性:表1に示す樹脂組成物を用いて、15×15×0.5mmのシリコンチップを銅ヒートスプレッダー(25×25×2mm、被着面は銅表面)にマウントし、175℃オーブンにて30分硬化した。硬化後の濡れ広がり性の様子を超音波探傷装置(反射型)にて測定し塗布作業性の指標とした。濡れ面積が90%以上のものを合格とした。
・耐リフロー性(1):表1に示す樹脂組成物を用いて下記のリードフレームにシリコンチップをマウントしオーブン中175℃30分間硬化し接着した。マウントはダイボンダー(ASM社製)を用い、樹脂組成物塗布直後に塗布厚みが約25μmになるように調整して行った。樹脂組成物硬化後のリードフレームを封止材料(スミコンEME−G700H、住友ベークライト(株)製)を用い封止し、半導体装置を作製した。この半導体装置を85℃、相対湿度60%、168時間吸湿処理した後、IRリフロー処理(260℃、10秒、3回リフロー)を行った。処理後の半導体装置を超音波探傷装置(透過型)により剥離の程度を測定した。剥離面積の単位は%である。ダイアタッチ部の剥離面積が10%未満の場合を合格とした。
半導体装置:QFP(14×20×2.0mm)
リードフレーム:銀メッキした銅フレーム(被着部分が銀メッキ)
チップサイズ:6×6mm
・耐リフロー性(2):使用するリードフレームとして銀リングメッキした銅フレーム(被着部分が銅表面)を使用した以外は耐リフロー性(1)と同様にして半導体装置を作製し剥離の測定を行った。ダイアタッチ部の剥離面積が10%未満の場合を合格とした。
これに対し本発明を逸脱する比較例1に示す樹脂組成物は、塗布作業性は良好であるが、化合物(C1)及び化合物(C2)を含まないため接着特性に劣り、耐温度サイクル試験及び耐リフロー試験において顕著な剥離の進展が見られた。比較例2に示す樹脂組成物は、塗布作業性は良好であるが、化合物(C1)を含まないため接着特性に劣り、耐リフロー試験において顕著な剥離の進展が見られた。比較例3に示す樹脂組成物は、塗布作業性は良好であるが、化合物(C2)を含まないため銅表面に対する接着特性に劣り、耐温度サイクル試験及び銀リングメッキ銅フレーム(被着部分が銅表面)を用いた耐リフロー試験において顕著な剥離の進展が見られた。
Claims (6)
- 導電性粒子(A)、熱硬化性樹脂(B)、スルフィド結合とアルコキシシリル基を有する化合物(C1)、及びスルフィド結合と水酸基を有する化合物(C2)を含むことを特徴とする樹脂組成物。
- 前記化合物(C2)が、芳香族環を含まない化合物である請求項1に記載の樹脂組成物。
- 前記化合物(C2)が、2,2'−ジチオジエタノール、3−チアペンタンジオール、3,6−ジチアオクタン−1,8−ジオール、及び3,6,9−トリチアウンデカン−1,11−ジオールからなる群より選ばれる少なくとも1つ以上の化合物である請求項1または請求項2に記載の樹脂組成物。
- 前記化合物(C1)と前記化合物(C2)の配合比が (C1)/(C2)=1/9〜9/1である請求項1〜請求項3のいずれか1項に記載の樹脂組成物。
- 請求項1〜請求項4のいずれか1項に記載の樹脂組成物を加熱することにより得られることを特徴とする接着剤層。
- 請求項1〜請求項4のいずれか1項に記載の樹脂組成物を半導体用ダイアタッチペーストまたは放熱部材接着用材料として用いて作製したことを特徴とする半導体装置。
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