JP6473322B2 - Curable resin composition, dispensing die attach material, and semiconductor device - Google Patents
Curable resin composition, dispensing die attach material, and semiconductor device Download PDFInfo
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- JP6473322B2 JP6473322B2 JP2014236178A JP2014236178A JP6473322B2 JP 6473322 B2 JP6473322 B2 JP 6473322B2 JP 2014236178 A JP2014236178 A JP 2014236178A JP 2014236178 A JP2014236178 A JP 2014236178A JP 6473322 B2 JP6473322 B2 JP 6473322B2
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- 239000011342 resin composition Substances 0.000 title claims description 83
- 239000000463 material Substances 0.000 title claims description 23
- 239000004065 semiconductor Substances 0.000 title claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 25
- 229920000647 polyepoxide Polymers 0.000 claims description 25
- 239000002245 particle Substances 0.000 claims description 21
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 239000002270 dispersing agent Substances 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000002270 phosphoric acid ester group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 22
- -1 polyoxyethylene Polymers 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- 101000896726 Homo sapiens Lanosterol 14-alpha demethylase Proteins 0.000 description 4
- 102100021695 Lanosterol 14-alpha demethylase Human genes 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical compound CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000017525 heat dissipation Effects 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000009974 thixotropic effect Effects 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- LPVHVQFTYXQKAP-YFKPBYRVSA-N (4r)-3-formyl-2,2-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC1(C)SC[C@@H](C(O)=O)N1C=O LPVHVQFTYXQKAP-YFKPBYRVSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- GTZHDRRNFNIFTL-UHFFFAOYSA-N 1-[4-(2-amino-2-methylpropyl)piperazin-1-yl]-2-methylpropan-2-amine Chemical compound CC(C)(N)CN1CCN(CC(C)(C)N)CC1 GTZHDRRNFNIFTL-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- LMVLMHGTZULBRX-UHFFFAOYSA-N 2-[2,2,2-tris(2-hydroxyphenyl)ethyl]phenol Chemical compound OC1=CC=CC=C1CC(C=1C(=CC=CC=1)O)(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LMVLMHGTZULBRX-UHFFFAOYSA-N 0.000 description 1
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 description 1
- SZUPZARBRLCVCB-UHFFFAOYSA-N 3-(2-undecylimidazol-1-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC=CN1CCC#N SZUPZARBRLCVCB-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 101100478890 Caenorhabditis elegans smo-1 gene Proteins 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Die Bonding (AREA)
Description
本発明は、硬化性樹脂組成物、ディスペンス用ダイアタッチ材、および半導体装置に関し、特に、放熱性に優れ、信頼性の高い半導体装置を形成可能な硬化性樹脂組成物、およびディスペンス用ダイアタッチ材、ならびにこのディスペンス用ダイアタッチ材により製造される半導体装置に関する。 The present invention relates to a curable resin composition, a die attach material for dispensing, and a semiconductor device, and in particular, a curable resin composition that is excellent in heat dissipation and capable of forming a highly reliable semiconductor device, and a die attach material for dispensing. In addition, the present invention relates to a semiconductor device manufactured using the dispensing die attach material.
基板とダイ、またはダイ同士を接着・接続するために、ダイアタッチ材が用いられている。近年、このダイアタッチ材には、放熱性の観点から、高熱伝導性が求められている。一般に、高熱伝導性を達成するためには、フィラーを高密度に充填することが行われる。しかし、フィラーを高密度に充填すると、ダイアタッチ材の粘度が高くなり、ディスペンスでの作業性が低下する、という問題が生じてしまう。 A die attach material is used to bond and connect the substrate and the die or between the dies. In recent years, this die attach material has been required to have high thermal conductivity from the viewpoint of heat dissipation. Generally, in order to achieve high thermal conductivity, a filler is filled at a high density. However, when the filler is filled at a high density, the viscosity of the die attach material becomes high, resulting in a problem that workability in dispensing decreases.
ディスペンスでの作業性を良くするためには、ダイアタッチ材が、低粘度、高揺変指数であることが望ましい。一方、ダイアタッチ材が低粘度になると、フィラーは沈降し易くなり、均一な組成物が得られなくなる。 In order to improve workability in dispensing, it is desirable that the die attach material has a low viscosity and a high fluctuation index. On the other hand, if the die attach material has a low viscosity, the filler tends to settle and a uniform composition cannot be obtained.
熱伝導性無機粉末を多量に含有させても、粘度が低く、流動性に優れる硬化性組成物が開示されている(特許文献1)。この硬化性組成物は、所望の場所(被適用物)又は型に注入し、加熱硬化させる(特許文献1の第0075段落)ことを想定しているため、ディスペンス用途や、揺変指数について考慮されていない。本願発明の発明者らが、この特許文献の実施例に記載されているビックケミー製分散剤(商品名:DISPERBYK−111)を使用して硬化性組成物を作製したが、作製した硬化性組成物の揺変指数が低くなってしまい、ディスペンス時に硬化性組成物の切れが悪い、隣のパターンまで糸を引いてしまう、パターンがだれる等の問題がある。 A curable composition having a low viscosity and excellent fluidity even when containing a large amount of thermally conductive inorganic powder is disclosed (Patent Document 1). Since this curable composition is assumed to be injected into a desired place (applied object) or mold and cured by heating (paragraph 0075 of Patent Document 1), it is considered for dispensing use and a throttling index. It has not been. The inventors of the present invention made a curable composition using the Big Chemie dispersant (trade name: DISPERBYK-111) described in the examples of this patent document, but the produced curable composition There is a problem that the sway index is low, the curable composition is poorly cut at the time of dispensing, the yarn is pulled to the adjacent pattern, and the pattern is slackened.
また、一般式(1)で示されるリン酸エステル基を有する分散剤を使用する樹脂組成物が開示されている(特許文献2)。しかし、この樹脂組成物では、スクリーン印刷を考慮しているため(特許文献2の第0005段落)、エポキシ樹脂を使用せずに(特許文献2の第0003、0005段落)、アクリルモノマーやスチレンモノマーを使用して粘度を低下させており(特許文献2の第0030、0031段落)、揺変指数(チキソトロピー値)が低く、上述のようなディスペンス時の問題に加えて、ボイドが発生しやすく、さらに、硬化物の耐熱性や耐水性が悪くなる、という問題がある。 Moreover, the resin composition which uses the dispersing agent which has the phosphate ester group shown by General formula (1) is disclosed (patent document 2). However, in this resin composition, since screen printing is considered (paragraph 0005 of Patent Document 2), an acrylic monomer or a styrene monomer is used without using an epoxy resin (paragraph 0003, 0005 of Patent Document 2). Is used to reduce the viscosity (paragraph 0030, 0031 of Patent Document 2), the thymotropic index (thixotropic value) is low, and in addition to the above-mentioned problems during dispensing, voids are likely to occur, Furthermore, there exists a problem that the heat resistance and water resistance of hardened | cured material worsen.
本発明は、低粘度でありながら、揺変指数が高く、硬化後に熱伝導率が高い硬化性樹脂組成物を提供することを目的とする。この硬化性樹脂組成物は、基板とダイ、またはダイ同士を接着・接続するダイアタッチ材、発熱材と放熱材とを接続する放熱材料(Thermal Interface Material:TIM)として好適に用いることができる。 An object of the present invention is to provide a curable resin composition having a low variation viscosity, a high throttling index, and a high thermal conductivity after curing. This curable resin composition can be suitably used as a die attach material for bonding and connecting the substrate and the die, or between the dies, and a heat radiating material (Thermal Interface Material: TIM) for connecting the heat generating material and the heat radiating material.
本発明は、以下の構成を有することによって上記問題を解決した硬化性樹脂組成物、ディスペンス用ダイアタッチ材、および半導体装置に関する。
〔1〕(A)エポキシ樹脂、(B)粒度分布において、最頻粒径が0.1〜10μmである無機充填材、および(C)一般式(1):
The present invention relates to a curable resin composition, a die attach material for dispensing, and a semiconductor device that have solved the above problems by having the following configuration.
[1] (A) an epoxy resin, (B) an inorganic filler having a mode particle size of 0.1 to 10 μm in the particle size distribution, and (C) the general formula (1):
(式中、Rは、同一でも異なってもよく、CqH2q+1−CH2O−(CH2CH2O)p−CH2CH2O−であり、pは8〜10、qは12〜16、xは1〜3の整数である)で示されるリン酸エステル基を有する分散剤を含むことを特徴とする、硬化性樹脂組成物。
〔2〕(C)成分が、硬化性樹脂組成物100質量部に対して、0.5〜5質量部である、上記〔1〕記載の硬化性樹脂組成物。
〔3〕(B)成分が、粒度分布において、0.1μm以上1μm未満と、1μm以上10μm以下の範囲内に、それぞれ頻度極大ピークを有する、上記〔1〕または〔2〕記載の硬化性樹脂組成物。
〔4〕(B)成分が、アルミナを含む、上記〔1〕〜〔3〕のいずれか記載の硬化性樹脂組成物。
〔5〕(B)成分が、硬化性樹脂組成物100質量部に対して、70〜90質量部である、上記〔1〕〜〔4〕のいずれか記載の硬化性樹脂組成物。
〔6〕揺変指数が、3〜6である、上記〔1〕〜〔5〕のいずれか記載の硬化性樹脂組成物。
〔7〕回転式粘度計で、25℃、5rpmでの粘度が、10〜40Pa・sである、上記〔1〕〜〔6〕のいずれか記載の硬化性樹脂組成物。
〔8〕上記〔1〕〜〔7〕のいずれか記載の硬化性樹脂組成物を用いる、ディスペンス用ダイアタッチ材。
〔9〕上記〔1〕〜〔7〕のいずれか記載の硬化性樹脂組成物の硬化体を有する、半導体装置。
(Wherein, R may be the same or different, C q H 2q + 1 -CH 2 O- (CH 2 CH 2 O) p -CH 2 CH 2 are O-, p is 8 to 10, q is 12 -16, x is an integer of 1-3, The curable resin composition characterized by including the dispersing agent which has a phosphate ester group shown.
[2] The curable resin composition according to the above [1], wherein the component (C) is 0.5 to 5 parts by mass with respect to 100 parts by mass of the curable resin composition.
[3] The curable resin according to the above [1] or [2], wherein the component (B) has a frequency maximum peak in the particle size distribution within the range of 0.1 μm or more and less than 1 μm and 1 μm or more and 10 μm or less. Composition.
[4] The curable resin composition according to any one of [1] to [3], wherein the component (B) includes alumina.
[5] The curable resin composition according to any one of [1] to [4], wherein the component (B) is 70 to 90 parts by mass with respect to 100 parts by mass of the curable resin composition.
[6] The curable resin composition according to any one of the above [1] to [5], wherein the variation index is 3 to 6.
[7] The curable resin composition according to any one of [1] to [6], wherein the viscosity at 25 ° C. and 5 rpm is 10 to 40 Pa · s with a rotary viscometer.
[8] A die attach material for dispensing using the curable resin composition according to any one of [1] to [7].
[9] A semiconductor device having a cured body of the curable resin composition according to any one of [1] to [7].
本発明〔1〕によれば、低粘度でありながら、揺変指数が高く、硬化後に熱伝導率が高い硬化性樹脂組成物を提供することができる。 According to the present invention [1], it is possible to provide a curable resin composition having a low viscosity, a high throttling index, and a high thermal conductivity after curing.
本発明〔8〕によれば、低粘度でありながら、揺変指数が高く、硬化後に熱伝導率が高い硬化性樹脂組成物を用いる、ディスペンス用ダイアタッチ材を提供することができる。本発明〔9〕によれば、熱伝導性が高いディスペンス用ダイアタッチ材の硬化体により、高信頼性の半導体装置を提供することができる。 According to the present invention [8], it is possible to provide a die attach material for dispensing that uses a curable resin composition that has a low coefficient of viscosity and a high thickness index and a high thermal conductivity after curing. According to the present invention [9], a highly reliable semiconductor device can be provided by a cured body of a dispense die attach material having high thermal conductivity.
〔硬化性樹脂組成物〕
本発明の硬化性樹脂組成物(以下、硬化性樹脂組成物という)は、(A)エポキシ樹脂、(B)粒度分布において、最頻粒径が0.1〜10μmである無機充填材、および(C)一般式(1):
[Curable resin composition]
The curable resin composition of the present invention (hereinafter referred to as curable resin composition) includes (A) an epoxy resin, (B) an inorganic filler having a mode particle size of 0.1 to 10 μm in the particle size distribution, and (C) General formula (1):
(式中、Rは、同一でも異なってもよく、CqH2q+1−CH2O−(CH2CH2O)p−CH2CH2O−であり、pは8〜10、qは12〜16、xは1〜3の整数である)で示されるリン酸エステル基を有する分散剤を含むことを特徴とする。この硬化性樹脂組成物は、低粘度でありながら、高い揺変指数を有し、硬化後に熱伝導率が高い。これは、(C)成分が(B)成分である無機充填材表面に作用し、(B)成分である平均粒子径の小さいフィラー間で牽引力が生じ、フィラーが連続した構造を形成するためである、と考えられる。 (Wherein, R may be the same or different, C q H 2q + 1 -CH 2 O- (CH 2 CH 2 O) p -CH 2 CH 2 are O-, p is 8 to 10, q is 12 To 16 and x is an integer of 1 to 3), and a dispersant having a phosphate ester group is included. Although this curable resin composition has a low viscosity, it has a high thickness index and has a high thermal conductivity after curing. This is because the component (C) acts on the surface of the inorganic filler which is the component (B), and a traction force is generated between the fillers having a small average particle diameter which is the component (B) to form a continuous filler structure. It is believed that there is.
(A)成分であるエポキシ樹脂は、硬化性樹脂組成物に、接着性、硬化性を付与し、硬化後の硬化性樹脂組成物に、耐久性、耐熱性を付与する。(A)成分としては、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、脂環式エポキシ樹脂、ベンゼン環を多数有した多官能型であるテトラキス(ヒドロキシフェニル)エタン型又はトリス(ヒドロキシフェニル)メタン型エポキシ樹脂、ビフェニル型エポキシ樹脂、トリフェノールメタン型エポキシ樹脂、ポリブタジエン型エポキシ樹脂(エポキシ化ポリブタジエン)、ナフタレン型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、アミノフェノール型エポキシ樹脂、シリコーンエポキシ樹脂等が挙げられる。ビスフェノールAエチレンオキシド付加物のジグリシジルエーテル、ビスフェノールAプロピレンオキシド付加物のジグリシジルエーテル等のポリグリシジルエステル、p−キシリレングリコールと1−クロロ−2,3−エポキシプロパンの反応生成物等も使用することができる。 The epoxy resin as the component (A) imparts adhesiveness and curability to the curable resin composition, and imparts durability and heat resistance to the cured curable resin composition. As component (A), bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin, tetrakis (hydroxyphenyl) ethane type which is a polyfunctional type having many benzene rings or Tris (hydroxyphenyl) methane type epoxy resin, biphenyl type epoxy resin, triphenolmethane type epoxy resin, polybutadiene type epoxy resin (epoxidized polybutadiene), naphthalene type epoxy resin, dicyclopentadiene type epoxy resin, aminophenol type epoxy resin, A silicone epoxy resin etc. are mentioned. Polyglycidyl ester such as diglycidyl ether of bisphenol A ethylene oxide adduct, diglycidyl ether of bisphenol A propylene oxide adduct, reaction product of p-xylylene glycol and 1-chloro-2,3-epoxypropane, etc. are also used. be able to.
中でも、硬化物の柔軟性確保の点からポリブタジエン型エポキシ樹脂が好ましく、また、組成物の粘度と硬化物の強度及び柔軟性確保の点から、25℃での粘度が3Pa・s以下である、ビスフェノールAプロピレンオキシド付加物のジグリシジルエーテル(BPA−POタイプ)のエポキシ樹脂が好ましい。また、(A)成分であるエポキシ樹脂は、低粘度化の観点から、液状であることが好ましい。市販品としては、DIC製ビスフェノールA型/ビスフェノールF型混合型エポキシ樹脂(品名:EXA835LV)、モメンティブ・パフォーマンス製シロキサン系エポキシ樹脂(品名:TSL9906)、新日鉄住金化学製1,4−シクロヘキサンジメタノールジグリシジルエーテル(品名:ZX1658GS)、ADEKA製エポキシ樹脂(品名:EP−4000S)、ADEKA製ビスフェノールAプロピレンオキシド付加物のジグリシジルエーテル(品名:BPA−PO4000S)等が挙げられる。(A)成分は、単独でも2種以上を併用してもよい。 Among them, a polybutadiene type epoxy resin is preferable from the viewpoint of ensuring the flexibility of the cured product, and the viscosity at 25 ° C. is 3 Pa · s or less from the viewpoint of ensuring the viscosity of the composition and the strength and flexibility of the cured product. A diglycidyl ether (BPA-PO type) epoxy resin of bisphenol A propylene oxide adduct is preferred. Moreover, it is preferable that the epoxy resin which is (A) component is a liquid form from a viewpoint of viscosity reduction. Commercially available products include DIC bisphenol A / bisphenol F mixed epoxy resin (product name: EXA835LV), Momentive Performance siloxane epoxy resin (product name: TSL9906), Nippon Steel & Sumikin Chemical 1,4-cyclohexanedimethanol di Examples thereof include glycidyl ether (product name: ZX1658GS), ADEKA epoxy resin (product name: EP-4000S), ADEKA bisphenol A propylene oxide adduct diglycidyl ether (product name: BPA-PO4000S), and the like. (A) A component may be individual or may use 2 or more types together.
(B)成分は、硬化後の硬化性樹脂組成物に、高熱伝導性を付与する。(B)成分は、粒度分布において、最頻粒径が0.1〜10μmであり、すなわち、0.1〜10μmの範囲内に少なくとも1つの頻度極大ピークを有する。(B)成分の最頻粒径が、0.1μm未満だと、硬化性樹脂組成物の粘度が上昇して、ディスペンス作業性が低下する。10μm超だと、硬化性樹脂組成物中での充填密度が低下し、硬化後の硬化性樹脂組成物の熱伝導率が低下してしまう。ここで、無機充填材の最頻粒径や頻度極大ピークは、平均粒径(粒状でない場合は、その平均最大径)を測定後、そのデータを解析することで得られる。平均粒径(粒状でない場合は、その平均最大径)は、レーザー回折法によって測定した体積基準のメジアン径をいい、例えば、レーザー散乱回析法粒度分布測定装置:LS13320(ベックマンコールター社製、湿式)により測定できる。 The component (B) imparts high thermal conductivity to the cured curable resin composition. In the particle size distribution, the component (B) has a mode particle size of 0.1 to 10 μm, that is, has at least one frequency maximum peak in the range of 0.1 to 10 μm. When the mode particle size of the component (B) is less than 0.1 μm, the viscosity of the curable resin composition increases and the dispensing workability decreases. When it exceeds 10 μm, the filling density in the curable resin composition is lowered, and the thermal conductivity of the curable resin composition after curing is lowered. Here, the mode particle diameter and the frequency maximum peak of the inorganic filler are obtained by measuring the average particle diameter (or the average maximum diameter if not granular) and then analyzing the data. The average particle diameter (or the average maximum diameter if not granular) refers to a volume-based median diameter measured by a laser diffraction method. For example, laser scattering diffraction particle size distribution analyzer: LS13320 (manufactured by Beckman Coulter, Inc., wet type) ).
(B)成分は、0.1μm以上1μm未満と、1μm以上10μm以下の範囲内に、それぞれ頻度極大ピークを有すると、硬化性樹脂組成物の低粘度化、硬化性樹脂組成物中での(B)成分の高密度充填化の観点から好ましい。0.1μm以上1μm未満の範囲内に頻度極大ピークを有する無機充填材と、1μm以上10μm以下の範囲内に頻度極大ピークを有する無機充填材の割合については、1μm以上10μm以下の範囲内に頻度極大ピークを有する無機充填材が、(B)成分100質量部に対して、60〜90質量部であると好ましく、65〜80質量部であると、より好ましい。この0.1μm以上1μm未満と、1μm以上10μm以下の範囲内に、それぞれ頻度極大ピークを有する無機充填材は、例えば、平均粒径が0.1μm以上1μm未満の無機充填材と、平均粒径が1μm以上10μm以下の無機充填材を混合して作製することができる。 When the component (B) has a frequency maximum peak in the range of 0.1 μm or more and less than 1 μm and 1 μm or more and 10 μm or less, respectively, the viscosity of the curable resin composition is reduced. B) It is preferable from the viewpoint of high density packing of the component. About the ratio of the inorganic filler which has a frequency maximum peak in the range of 0.1 micrometer or more and less than 1 micrometer, and the inorganic filler which has a frequency maximum peak in the range of 1 micrometer or more and 10 micrometers or less, it is frequency in the range of 1 micrometer or more and 10 micrometers or less. The inorganic filler having a maximum peak is preferably 60 to 90 parts by mass and more preferably 65 to 80 parts by mass with respect to 100 parts by mass of the component (B). The inorganic filler having a frequency maximum peak in the range of 0.1 μm or more and less than 1 μm and 1 μm or more and 10 μm or less is, for example, an inorganic filler having an average particle diameter of 0.1 μm or more and less than 1 μm, and an average particle diameter Can be prepared by mixing inorganic fillers of 1 μm or more and 10 μm or less.
(B)成分は、硬化後の硬化性樹脂組成物の高熱伝導化の観点から、アルミナ、酸化マグネシウム、窒化ホウ素を含むと好ましく、硬化後の硬化性樹脂組成物中での耐湿性の観点から、アルミナを含むと、より好ましい。各材料の熱伝導率測定結果の一例としては(単位は、W/m・K)、Al2O3は30、MgOは37、BNは30である。また、(B)成分が、シリカを含むと、シリカの添加量により硬化性樹脂組成物の揺変指数を制御することができ、ディスペンス用途での作業性向上の観点から、好ましい。(B)成分の市販品としては、昭和電工製アルミナ(Al2O3)粉末(品名:CBP05)、電気化学工業製アルミナ(Al2O3)粉末(品名:DAW−03、ASFP−20)、住友化学製アルミナ(Al2O3)粉末(品名:AA−3)、堺化学工業製酸化マグネシウム粉末(品名:SMO−5、SMO−1、SMO−02、SMO−2)が挙げられる。(B)成分は、単独でも2種以上を併用してもよい。 The component (B) preferably contains alumina, magnesium oxide and boron nitride from the viewpoint of increasing the thermal conductivity of the curable resin composition after curing, and from the viewpoint of moisture resistance in the curable resin composition after curing. More preferably, alumina is included. As an example of the thermal conductivity measurement result of each material (unit: W / m · K), Al 2 O 3 is 30, MgO is 37, and BN is 30. In addition, it is preferable that the component (B) contains silica from the viewpoint of improving workability in dispensing applications, because the variation index of the curable resin composition can be controlled by the amount of silica added. As the component (B) of the commercially available products, manufactured by Showa Denko alumina (Al 2 O 3) powder (product name: CBP05), manufactured by Denki Kagaku Kogyo Kabushiki alumina (Al 2 O 3) powder (product name: DAW-03, ASFP-20 ) , Alumina (Al 2 O 3 ) powder (product name: AA-3) manufactured by Sumitomo Chemical Co., Ltd., magnesium oxide powder (product names: SMO-5, SMO-1, SMO-02, SMO-2) manufactured by Sakai Chemical Industry. (B) A component may be individual or may use 2 or more types together.
(C)成分は、一般式(1): The component (C) is represented by the general formula (1):
(式中、Rは、同一でも異なってもよく、CqH2q+1−CH2O−(CH2CH2O)p−CH2CH2O−であり、pは8〜10、qは12〜16、xは1〜3の整数である)で示されるリン酸エステル基を有する分散剤であり、硬化性樹脂組成物を高揺変指数にすることができる。(C)成分の市販品としては、楠本化成株式会社製ポリオキシエチレンアルキルリン酸エステル分散剤(一般式(1)において、p=約9、q=約13、x=約3のリン酸エステル基を有する分散剤、品名:ED151)が挙げられる。(C)成分は、単独でも2種以上を併用してもよい。 (Wherein, R may be the same or different, C q H 2q + 1 -CH 2 O- (CH 2 CH 2 O) p -CH 2 CH 2 are O-, p is 8 to 10, q is 12 -16, x is an integer of 1 to 3) and has a phosphate ester group, and can make the curable resin composition have a high variation index. As a commercially available product of component (C), polyoxyethylene alkyl phosphate dispersant manufactured by Enomoto Kasei Co., Ltd. (in general formula (1), p = about 9, q = about 13, x = about 3 phosphate ester And a dispersant having a group, product name: ED151). (C) A component may be individual or may use 2 or more types together.
(A)成分は、硬化性樹脂組成物(溶剤を除く):100質量部に対して、1.5〜15質量部であると好ましく、2〜10質量部であると、より好ましい。 The component (A) is preferably 1.5 to 15 parts by mass, more preferably 2 to 10 parts by mass with respect to 100 parts by mass of the curable resin composition (excluding the solvent).
(B)成分は、硬化性樹脂組成物の接着性、硬化後の硬化性樹脂組成物の熱膨張係数、絶縁性の観点から、硬化性樹脂組成物100質量部(溶剤を除く)に対して、70〜90質量部であると好ましく、80〜87質量部であると、より好ましい。 The component (B) is based on 100 parts by mass (excluding the solvent) of the curable resin composition from the viewpoints of adhesiveness of the curable resin composition, thermal expansion coefficient of the curable resin composition after curing, and insulating properties. 70 to 90 parts by mass, and more preferably 80 to 87 parts by mass.
(C)成分は、硬化性樹脂組成物100質量部(溶剤を除く)に対して、0.5〜5質量部であると好ましく、0.6〜2.5質量部であると、より好ましい。(C)成分が0.5質量部以上であると、硬化性樹脂組成物を高揺変指数にし易く、2.5質量部以下であると、硬化時のボイド発生を抑制し易い。 The component (C) is preferably 0.5 to 5 parts by mass and more preferably 0.6 to 2.5 parts by mass with respect to 100 parts by mass (excluding the solvent ) of the curable resin composition. . When the component (C) is 0.5 part by mass or more, the curable resin composition is likely to have a high variation index, and when it is 2.5 parts by mass or less, generation of voids during curing is easily suppressed.
硬化性樹脂組成物は、さらに、(D)硬化剤を含む、と好ましい。(D)成分としては、フェノール系硬化剤、酸無水物系硬化剤、アミン系硬化剤、ヒドラジド化合物、ジシアンジアミド等を使用することができる。硬化性樹脂組成物の接着性の観点から、フェノール系硬化剤がより好ましく、また、硬化性樹脂組成物の流動性、接着性の観点から、酸無水物系硬化剤がより好ましい。硬化性樹脂組成物の保存安定性の観点からは、アミン系硬化剤のうちイミダゾール系硬化剤がより好ましい。接着性と保存安定性の観点からは、ジシアンジアミドがより好ましい。 It is preferable that the curable resin composition further includes (D) a curing agent. As the component (D), a phenol-based curing agent, an acid anhydride-based curing agent, an amine-based curing agent, a hydrazide compound, dicyandiamide, and the like can be used. From the viewpoint of adhesiveness of the curable resin composition, a phenol-based curing agent is more preferable, and from the viewpoint of fluidity and adhesiveness of the curable resin composition, an acid anhydride-based curing agent is more preferable. From the viewpoint of storage stability of the curable resin composition, an imidazole curing agent is more preferable among the amine curing agents. From the viewpoints of adhesiveness and storage stability, dicyandiamide is more preferable.
フェノール樹脂系硬化剤としては、エポキシ樹脂の硬化剤として公知のフェノール樹脂を用いることができ、例えば、レゾール型又はノボラック型フェノール樹脂を用いることができ、アルキルレゾール型、アルキルノボラック型、アラルキルノボラック型のフェノール樹脂、キシレン樹脂、アリルフェノール樹脂等が挙げられる。数平均分子量としては、220〜1000であることが好ましく、220〜500がより好ましい。アルキルレゾール型又はアルキルノボラック型フェノール樹脂の場合、アルキル基としては、炭素数1〜18のものを用いることができ、エチル、プロピル、ブチル、ペンチル、ヘキシル、オクチル、ノニル、デシルのような炭素数2〜10のものが好ましい。フェノール樹脂系硬化剤として市販されているものとしては、明和化成株式会社製フェノール樹脂系硬化剤(品名:MEH8005)等が挙げられる。 As the phenol resin-based curing agent, a known phenol resin can be used as a curing agent for an epoxy resin. For example, a resol type or novolac type phenol resin can be used, and an alkyl resole type, an alkyl novolak type, an aralkyl novolak type. Phenol resin, xylene resin, allylphenol resin, and the like. As a number average molecular weight, it is preferable that it is 220-1000, and 220-500 are more preferable. In the case of an alkylresole type or alkyl novolac type phenolic resin, the alkyl group can be one having 1 to 18 carbon atoms, such as ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, decyl. The thing of 2-10 is preferable. As what is marketed as a phenol resin type hardening | curing agent, Meiwa Kasei Co., Ltd. phenol resin type hardening agent (product name: MEH8005) etc. are mentioned.
酸無水物系硬化剤としては、エポキシ樹脂の硬化剤として公知の酸無水物を用いることができ、無水フタル酸、無水マレイン酸、ドデセニル無水コハク酸、トリメリット酸無水物、ベンゾフェノンテトラカルボン酸二無水物、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸等が挙げられる。酸無水物系硬化剤として市販されているものとしては、三菱化学株式会社製酸無水物系硬化剤(品名:YH307)等が挙げられる。 As the acid anhydride curing agent, known acid anhydrides can be used as epoxy resin curing agents, such as phthalic anhydride, maleic anhydride, dodecenyl succinic anhydride, trimellitic anhydride, benzophenone tetracarboxylic acid dicarboxylic acid. Anhydrides, tetrahydrophthalic anhydride, hexahydrophthalic anhydride and the like can be mentioned. As what is marketed as an acid anhydride type hardening | curing agent, Mitsubishi Chemical Corporation acid anhydride type hardening | curing agent (product name: YH307) etc. are mentioned.
アミン系硬化剤には、脂肪族アミン、芳香族アミンの他、イミダゾール類も包含される。
脂肪族アミンとしては、ジエチレントリアミン、トリエチレンテトラアミン、テトラエチレンペンタミン、トリメチルヘキサメチレンジアミン、m−キシレンジアミン、2−メチルペンタメチレンジアミン等の脂肪族ポリアミン、イソフォロンジアミン、1,3−ビスアミノメチルシクロヘキサン、ビス(4−アミノシクロヘキシル)メタン、ノルボルネンジアミン、1,2−ジアミノシクロヘキサン等の脂環式ポリアミン、N−アミノエチルピペラジン、1,4−ビス(2−アミノ−2−メチルプロピル)ピペラジン等のピペラジン型のポリアミンが挙げられる。芳香族アミンとしては、ジアミノジフェニルメタン、m−フェニレンジアミン、ジアミノジフェニルスルホン、ジエチルトルエンジアミン、トリメチレンビス(4−アミノベンゾエート)、ポリテトラメチレンオキシド−ジ−p−アミノベンゾエート等の芳香族ポリアミン等が挙げられる。トリス(ジメチルアミノメチル)フェノール、ベンジルジメチルアミン、1,8−ジアザビシクロ(5,4,0)ウンデンセン−7等の3級アミン等も使用することができる。
Amine-based curing agents include aliphatic amines and aromatic amines as well as imidazoles.
Examples of aliphatic amines include aliphatic polyamines such as diethylenetriamine, triethylenetetraamine, tetraethylenepentamine, trimethylhexamethylenediamine, m-xylenediamine, and 2-methylpentamethylenediamine, isophoronediamine, and 1,3-bisamino. Cycloaliphatic polyamines such as methylcyclohexane, bis (4-aminocyclohexyl) methane, norbornenediamine, 1,2-diaminocyclohexane, N-aminoethylpiperazine, 1,4-bis (2-amino-2-methylpropyl) piperazine And piperazine type polyamines such as Aromatic amines include diaminodiphenylmethane, m-phenylenediamine, diaminodiphenylsulfone, diethyltoluenediamine, trimethylenebis (4-aminobenzoate), and polytetramethylene oxide-di-p-aminobenzoate. Can be mentioned. Tertiary amines such as tris (dimethylaminomethyl) phenol, benzyldimethylamine, 1,8-diazabicyclo (5,4,0) undensen-7, and the like can also be used.
また、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、2−メチルイミダゾール、2−フェニル−4−メチルイミダゾール、1−シアノエチル−2−メチルイミダゾール、1−シアノエチル−2−ウンデシルイミダゾール、2−フェニル−4−メチル−5−ヒドロキシメチルイミダゾール、2−フェニル−4,5−ジヒドロキシメチルイミダゾール等のイミダゾール化合物も使用することができる。 Further, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-methylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 2 -Imidazole compounds such as phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole can also be used.
変性イミダゾール系硬化剤も使用することができ、エポキシ−イミダゾールアダクト系化合物やアクリレート−イミダゾールアダクト化合物が挙げられる。エポキシ−イミダゾールアダクト系化合物として市販されているものとしては、味の素ファインテクノ社製硬化剤(品名:アミキュアPN−23、アミキュアPN−40)、旭化成イーマテリアルズ社製硬化剤(品名:ノバキュアHX−3721)、富士化成工業社製硬化剤(品名:フジキュアFX−1000)等が挙げられる。また、アクリレート−イミダゾールアダクト系化合物として市販されているものとしては、例えば、ADEKA社製硬化剤(品名:EH2021)等が挙げられる。(D)成分は、これら品名に限定されるものではない。(D)成分は、単独でも2種以上を併用してもよい。 Modified imidazole-based curing agents can also be used, and examples include epoxy-imidazole adduct compounds and acrylate-imidazole adduct compounds. Examples of commercially available epoxy-imidazole adduct compounds include curing agents manufactured by Ajinomoto Fine Techno Co., Ltd. (product names: Amicure PN-23, Amicure PN-40), curing agents manufactured by Asahi Kasei E-Materials Co., Ltd. (product name: NovaCure HX- 3721), a curing agent (product name: Fujicure FX-1000) manufactured by Fuji Kasei Kogyo Co., Ltd., and the like. Moreover, as what is marketed as an acrylate-imidazole adduct type compound, the hardening agent (product name: EH2021) by ADEKA, etc. are mentioned, for example. The component (D) is not limited to these product names. (D) A component may be individual or may use 2 or more types together.
(D)成分は、硬化性樹脂組成物の保存安定性、硬化性の観点から、硬化性樹脂組成物(溶剤を除く):100質量部に対して、0.1〜10質量部であると好ましい。 (D) A component is 0.1-10 mass parts with respect to 100 mass parts of curable resin composition (except a solvent) from the viewpoint of the storage stability of a curable resin composition, and sclerosis | hardenability. preferable.
なお、硬化性樹脂組成物は、本発明の効果を損なわない範囲で、アクリル樹脂、ラジカル重合発生剤、カップリング剤、消泡剤等の添加剤や、有機溶剤を含むことができる。アクリル樹脂の市販品としては、共栄社化学株式会社製アクリル樹脂(品名:ライトエステルNP)、ラジカル重合発生剤の市販品としては、日油株式会社製ラジカル重合開始剤1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート(品名:パーオクタO)が挙げられ、カップリング材の市販品としては、信越化学工業株式会社製3−グリシドキシプロピルトリメトキシシラン(品名:KBM−403)が挙げられる。 The curable resin composition can contain an additive such as an acrylic resin, a radical polymerization generator, a coupling agent, and an antifoaming agent, and an organic solvent as long as the effects of the present invention are not impaired. As a commercial product of acrylic resin, Kyoeisha Chemical Co., Ltd. acrylic resin (product name: light ester NP), as a commercial product of radical polymerization generator, NOF Corporation radical polymerization initiator 1,1,3,3- Tetramethylbutyl peroxy-2-ethylhexanoate (product name: perocta O) is mentioned, and a commercially available coupling material is 3-glycidoxypropyltrimethoxysilane (product name: KBM) manufactured by Shin-Etsu Chemical Co., Ltd. -403).
硬化性樹脂組成物の回転式粘度計で、25℃、5rpmでの粘度は、ディスペンス用途での作業性の観点から、10〜40Pa・sであると好ましい。ここで、硬化性樹脂組成物の粘度は、ブルックフィールド社製回転式粘度計HB―DVII+P(コーンプレート型、スピンドル:CP51)を用い、25℃、5rpmで測定する。 In the rotary viscometer of the curable resin composition, the viscosity at 25 ° C. and 5 rpm is preferably 10 to 40 Pa · s from the viewpoint of workability in dispensing applications. Here, the viscosity of the curable resin composition is measured at 25 ° C. and 5 rpm using a Brookfield rotary viscometer HB-DVII + P (cone plate type, spindle: CP51).
硬化性樹脂組成物の揺変指数は、ディスペンス用途での作業性の観点から、3〜6であると好ましく、より好ましくは4〜6である。ここで、硬化性樹脂組成物の揺変指数は、粘度を、ブルックフィールド社製回転式粘度計HB―DVII+P(コーンプレート型、スピンドル:CP51)を用い、25℃で、0.5rpmと5rpmで測定し、〔(0.5rpmの粘度)/(5rpmの粘度)〕から求める。 The thrift index of the curable resin composition is preferably 3 to 6 and more preferably 4 to 6 from the viewpoint of workability in dispensing applications. Here, the tumbling index of the curable resin composition is the viscosity measured at 0.5 ° C. and 5 rpm at 25 ° C. using a rotational viscometer HB-DVII + P (cone plate type, spindle: CP51) manufactured by Brookfield. Measured and calculated from [(viscosity at 0.5 rpm) / (viscosity at 5 rpm)].
硬化後の硬化性樹脂組成物の熱伝導率は、接合されるダイ、基板等を含む半導体装置の放熱性の観点から、1W/m・K以上であると好ましく、2W/m・K以上であると、より好ましい。 The heat conductivity of the curable resin composition after curing is preferably 1 W / m · K or more from the viewpoint of heat dissipation of a semiconductor device including a die and a substrate to be joined, and is 2 W / m · K or more. More preferably.
上述の硬化性樹脂組成物は、(A)〜(C)成分等を含む原料を、分散させることにより、硬化性樹脂組成物を得ることができる。これらの原料の分散の装置としては、特に限定されるものではないが、撹拌、3本ロールミル、プラネタリーミキサー、ビーズミル等を使用することができる。また、これら装置を適宜組み合わせて使用してもよい。 The above-mentioned curable resin composition can obtain a curable resin composition by dispersing raw materials including the components (A) to (C). An apparatus for dispersing these raw materials is not particularly limited, and stirring, a three-roll mill, a planetary mixer, a bead mill and the like can be used. Moreover, you may use combining these apparatuses suitably.
このように、本発明の硬化性樹脂組成物は、低粘度でありながら、適切な揺変指数を有するので、ディスペンス用ダイアタッチ材として最適である。 Thus, since the curable resin composition of the present invention has an appropriate throttling index while having a low viscosity, it is optimal as a die attach material for dispensing.
〔半導体装置〕
本発明の半導体装置は、上述の硬化性樹脂組成物が硬化された硬化体を有する。熱伝導性に優れた硬化性樹脂組成物の硬化体により、高信頼性の半導体装置を提供することができる。半導体装置としては、ダイ(シリコンチップ等の半導体素子)、モジュール、電子部品などの発熱体と、基板などの受熱体とを、硬化性樹脂組成物の硬化物で接着したものや、発熱体からの熱を受熱した基板の熱と、この基板から更に受熱する放熱板などとを上述の硬化性樹脂組成物の硬化物で接着したものが、挙げられる。
[Semiconductor device]
The semiconductor device of the present invention has a cured body obtained by curing the above-described curable resin composition. A highly reliable semiconductor device can be provided by a cured body of a curable resin composition having excellent thermal conductivity. As a semiconductor device, a heating element such as a die (semiconductor element such as a silicon chip), a module, or an electronic component and a heat receiving element such as a substrate are bonded with a cured product of a curable resin composition, or a heating element And the heat of the substrate that has received the heat and the heat-radiating plate that further receives heat from the substrate are bonded with the cured product of the curable resin composition described above.
硬化性樹脂組成物をダイ、基板等に塗布する方法は、特に限定されないが、低粘度、高揺変指数である硬化性樹脂組成物の特性、生産性の観点から、ディスペンスが好ましい。 A method for applying the curable resin composition to a die, a substrate, or the like is not particularly limited, but dispensing is preferable from the viewpoint of the characteristics and productivity of the curable resin composition having a low viscosity and a high variation index.
硬化性樹脂組成物は、例えば、130〜180℃で、30〜120分間、熱硬化させて、被接着物を接着することができる。発熱体である被接着物と、受熱体である被接着物とを接着する場合、硬化した硬化性樹脂組成物は、発熱体である被接着物からの熱を受熱体である被接着物側へ逃がし、受熱体である被接着物側で放熱させる伝熱の役割を果たす。さらに、硬化した硬化性樹脂組成物は、発熱体である被接着物と受熱体である被接着物との間の熱膨張率の差に起因する応力を緩和する役割を果たす。 For example, the curable resin composition can be thermally cured at 130 to 180 ° C. for 30 to 120 minutes to adhere the adherend. When adhering an adherend that is a heating element and an adherend that is a heat receiving body, the cured curable resin composition takes heat from the adherend that is a heating element to the adherend side that is the heat receiving body. It plays the role of heat transfer that escapes and radiates heat on the adherend side that is a heat receiving body. Further, the cured curable resin composition plays a role of relieving stress caused by a difference in thermal expansion coefficient between an adherend that is a heating element and an adherend that is a heat receiving body.
本発明について、実施例により説明するが、本発明はこれらに限定されるものではない。なお、以下の実施例において、部、%はことわりのない限り、質量部、質量%を示す。また、(B)成分の平均粒径は、レーザー散乱回析法粒度分布測定装置:LS13320(ベックマンコールター社製、湿式)で測定し、その結果から最頻粒径や頻度極大ピークを算出した。 The present invention will be described with reference to examples, but the present invention is not limited thereto. In the following examples, parts and% indicate parts by mass and mass% unless otherwise specified. The average particle size of component (B) was measured with a laser scattering diffraction particle size distribution analyzer: LS13320 (manufactured by Beckman Coulter, Inc., wet type), and the mode particle size and frequency maximum peak were calculated from the results.
〔実施例1〜9、比較例1〜4〕
表1に示す配合で、(A)〜(D)成分等の原料を、3本ロールを用いて分散した後、真空撹拌を30分行い、硬化性樹脂組成物を作製した。
[Examples 1 to 9, Comparative Examples 1 to 4]
In the formulation shown in Table 1, after the raw materials such as the components (A) to (D) were dispersed using three rolls, vacuum stirring was performed for 30 minutes to prepare a curable resin composition.
〔硬化性樹脂組成物の評価方法〕
1.粘度の評価
作製した硬化性樹脂組成物の粘度を、ブルックフィールド社製回転式粘度計HB―DVII+P(コーンプレート型、スピンドル:CP51)を用い、25℃、5rpmで測定した。粘度が10〜40Pa・sの範囲に入るものが合格であり、それ以外は不合格である。表1に、結果を示す。
[Evaluation method of curable resin composition]
1. Evaluation of Viscosity The viscosity of the prepared curable resin composition was measured at 25 ° C. and 5 rpm using a Brookfield rotary viscometer HB-DVII + P (cone plate type, spindle: CP51). Those whose viscosities fall within the range of 10 to 40 Pa · s are acceptable, and others are unacceptable. Table 1 shows the results.
2.揺変指数の評価
硬化性樹脂組成物の揺変指数は、粘度を、ブルックフィールド社製回転式粘度計HB―DVII+P(コーンプレート型、スピンドル:CP51)を用い、25℃で、0.5rpmと5rpmで測定し、〔(0.5rpmの粘度)/(5rpmの粘度)〕から求めた。揺変指数が3〜6の範囲に入るものが合格であり、それ以外は不合格である。表1に、結果を示す。
2. Evaluation of Thickness Index The thickness index of the curable resin composition is 0.5 rpm at 25 ° C. using a rotational viscometer HB-DVII + P (cone plate type, spindle: CP51) manufactured by Brookfield. It was measured at 5 rpm and determined from [(0.5 rpm viscosity) / (5 rpm viscosity)]. Those in which the change index falls within the range of 3 to 6 are acceptable, and the others are unacceptable. Table 1 shows the results.
3.熱伝導率の評価
硬化性樹脂組成物を、ポリテトラフルオロエチレンフィルムを貼り付けたガラス板上に、乾燥後の膜厚が200〜400μmになるように掻き取り塗布した。図1に、掻き取り塗布の方法を説明するための模式図を示す。まず、ポリテトラフルオロエチレンフィルムを貼り付けたガラス板上に、適切な厚さとなるように、2列にスペーサーを重ねた後、粘着テープで貼付する(図1(A))。ポリテトラフルオロエチレンフィルムを貼り付けたガラス板上に、硬化性樹脂組成物を適量注ぐ(図1(B))。スライドガラスをスペーサー上に置き、硬化性樹脂組成物を掻き取って塗布する(図1(C)〜(E))。次に、塗布した硬化性樹脂組成物を、十分乾燥した後、得られた硬化性樹脂組成物のフィルムを、室温(25℃)から150℃まで30分で昇温し、150℃のオーブン中に30分間保持して硬化して、厚さ250μmのフィルム状の硬化物を作製した。このフィルム状の硬化物を、10×10mmに裁断し、熱伝導率測定用試験片を作製した。作製した熱伝導率測定用試験片の熱伝導率を、NETZSCH社製熱伝導率計(Xeフラッシュアナライザー、型番:LFA447Nanoflash)で測定した。表1に、結果を示す。
3. Evaluation of thermal conductivity The curable resin composition was scraped and applied on a glass plate on which a polytetrafluoroethylene film was attached so that the film thickness after drying was 200 to 400 μm. In FIG. 1, the schematic diagram for demonstrating the method of scraping application | coating is shown. First, spacers are stacked in two rows on a glass plate to which a polytetrafluoroethylene film is attached so as to have an appropriate thickness, and then attached with an adhesive tape (FIG. 1 (A)). An appropriate amount of a curable resin composition is poured onto a glass plate on which a polytetrafluoroethylene film is attached (FIG. 1B). A slide glass is placed on a spacer, and the curable resin composition is scraped and applied (FIGS. 1C to 1E). Next, after sufficiently drying the applied curable resin composition, the film of the obtained curable resin composition was heated from room temperature (25 ° C.) to 150 ° C. in 30 minutes, and in a 150 ° C. oven. And cured for 30 minutes to produce a film-like cured product having a thickness of 250 μm. This film-like cured product was cut into 10 × 10 mm to prepare a test piece for measuring thermal conductivity. The thermal conductivity of the prepared test piece for measuring thermal conductivity was measured with a thermal conductivity meter (Xe flash analyzer, model number: LFA447 Nanoflash) manufactured by NETZSCH. Table 1 shows the results.
表1からわかるように、実施例1〜10の全てで、粘度と揺変指数が適正な範囲内であり、かつ熱伝導率が高かった。特に、(B)成分が、79.9質量部以上である実施例1〜7、9、10では、熱伝導率が2.0W/m・K以上と高かった。また、(C)成分が0.8質量部以上である実施例1、3〜10では、揺変指数が4.0以上と特に優れていた。これに対して、(C)成分を含有しない比較例1は、粘度が高く、揺変指数が低かった。(C)成分の代わりに、酸性リン酸基を有する分散剤を使用した比較例2と、アルキロールアンモニウム塩分散剤を使用した比較例3は、いずれも揺変指数が低かった。 As can be seen from Table 1, in all of Examples 1 to 10, the viscosity and the fluctuation index were within appropriate ranges, and the thermal conductivity was high. In particular, in Examples 1 to 7, 9, and 10 in which the component (B) is 79.9 parts by mass or more, the thermal conductivity was as high as 2.0 W / m · K or more. In Examples 1 and 3 to 10 in which the component (C) is 0.8 parts by mass or more, the thymographic index was particularly excellent at 4.0 or more. On the other hand, the comparative example 1 which does not contain (C) component had a high viscosity, and the variation index was low. In Comparative Example 2 using a dispersant having an acidic phosphate group instead of the component (C), and Comparative Example 3 using an alkylol ammonium salt dispersant, the thixotropic index was low.
上記のように、本発明は、低粘度でありながら、揺変指数が高く、硬化後に熱伝導率が高い硬化性樹脂組成物を提供することができる。 As described above, the present invention can provide a curable resin composition having a low viscosity, a high throttling index, and a high thermal conductivity after curing.
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