WO2006019054A1 - 液状エポキシ樹脂組成物 - Google Patents
液状エポキシ樹脂組成物 Download PDFInfo
- Publication number
- WO2006019054A1 WO2006019054A1 PCT/JP2005/014842 JP2005014842W WO2006019054A1 WO 2006019054 A1 WO2006019054 A1 WO 2006019054A1 JP 2005014842 W JP2005014842 W JP 2005014842W WO 2006019054 A1 WO2006019054 A1 WO 2006019054A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- liquid epoxy
- resin composition
- amine
- component
- Prior art date
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- 239000004850 liquid epoxy resins (LERs) Substances 0.000 title claims abstract description 82
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 239000004065 semiconductor Substances 0.000 claims abstract description 45
- 150000001412 amines Chemical class 0.000 claims abstract description 40
- 239000002245 particle Substances 0.000 claims abstract description 38
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 24
- 239000005011 phenolic resin Substances 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 239000011256 inorganic filler Substances 0.000 claims abstract description 17
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 17
- 238000007789 sealing Methods 0.000 claims abstract description 14
- 239000007962 solid dispersion Substances 0.000 claims abstract description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims description 25
- -1 amine compound Chemical class 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 17
- 239000003822 epoxy resin Substances 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920005989 resin Polymers 0.000 abstract description 22
- 239000011347 resin Substances 0.000 abstract description 22
- 230000008439 repair process Effects 0.000 abstract description 12
- 239000000758 substrate Substances 0.000 abstract description 7
- 230000007547 defect Effects 0.000 abstract 1
- 229910000679 solder Inorganic materials 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000011049 filling Methods 0.000 description 11
- 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 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 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
- 238000001879 gelation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 230000009974 thixotropic effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical class ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000009863 impact test Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 1
- DENMGZODXQRYAR-UHFFFAOYSA-N 2-(dimethylamino)ethanethiol Chemical compound CN(C)CCS DENMGZODXQRYAR-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NLSFWPFWEPGCJJ-UHFFFAOYSA-N 2-methylprop-2-enoyloxysilicon Chemical compound CC(=C)C(=O)O[Si] NLSFWPFWEPGCJJ-UHFFFAOYSA-N 0.000 description 1
- MZWXWSVCNSPBLH-UHFFFAOYSA-N 3-(3-aminopropyl-methoxy-methylsilyl)oxypropan-1-amine Chemical compound NCCC[Si](C)(OC)OCCCN MZWXWSVCNSPBLH-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 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
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011802 pulverized particle Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XQGWAPPLBJZCEV-UHFFFAOYSA-N triethoxy(propyl)silane;urea Chemical compound NC(N)=O.CCC[Si](OCC)(OCC)OCC XQGWAPPLBJZCEV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
- H01L21/563—Encapsulation of active face of flip-chip device, e.g. underfilling or underencapsulation of flip-chip, encapsulation preform on chip or mounting substrate
-
- 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
- H01L2224/10—Bump connectors; Manufacturing methods related thereto
- H01L2224/15—Structure, shape, material or disposition of the bump connectors after the connecting process
- H01L2224/16—Structure, shape, material or disposition of the bump connectors after the connecting process of an individual bump 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
- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
- H01L2224/732—Location after the connecting process
- H01L2224/73201—Location after the connecting process on the same surface
- H01L2224/73203—Bump and layer connectors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/02—Semiconductor bodies ; Multistep manufacturing processes therefor
- H01L29/06—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by their shape; characterised by the shapes, relative sizes, or dispositions of the semiconductor regions ; characterised by the concentration or distribution of impurities within semiconductor regions
- H01L29/0657—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by their shape; characterised by the shapes, relative sizes, or dispositions of the semiconductor regions ; characterised by the concentration or distribution of impurities within semiconductor regions characterised by the shape of the body
-
- 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
- H01L2924/00014—Technical content checked by a classifier the subject-matter covered by the group, the symbol of which is combined with the symbol of this group, being disclosed without further technical details
-
- 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
- H01L2924/01004—Beryllium [Be]
-
- 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
- H01L2924/01012—Magnesium [Mg]
-
- 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
- H01L2924/0102—Calcium [Ca]
-
- 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
- H01L2924/01087—Francium [Fr]
Definitions
- the present invention relates to a semiconductor package and a circuit board via bump electrode portions for connection of a semiconductor package such as a BGA (ball grid 'array) or a CSP (chip scale' package or chip 'size' package).
- a semiconductor package such as a BGA (ball grid 'array) or a CSP (chip scale' package or chip 'size' package).
- the present invention relates to a liquid epoxy resin composition that is used when a gap between a semiconductor package and a circuit board is filled and sealed with a resin in a surface mounting method for electrically connecting the opposing electrodes.
- liquid resin composition used for the underfill a one-component thermosetting resin composition mainly composed of epoxy resin or the like is generally used. After being hardened, there is a problem that it cannot be easily repaired from the viewpoint of not melting, having high adhesive strength, not decomposing, or being insoluble in a solvent. Therefore, once underfill is performed, for example, a mounting board on which a semiconductor package having a defective electrical connection is scrapped and must be discarded. This means that in recent years, it is necessary to avoid as much as possible the generation of waste that does not require recyclability for the preservation of the global environment, and it is possible to enable repair even after underfill. It is requested.
- an epoxy resin is used as a main agent, a capsule type curing agent is coated with a thermoplastic resin as a curing agent, and an acrylic resin is used as a repairing property imparting agent.
- An adhesive for bonding electronic parts using resin is disclosed (patent) Reference 1).
- the present applicant firstly reduced the solubility parameter (SP value) of the cured product by reducing the solubility parameter (SP value) of the cured product with a trifluoromethyl substituent or a fluorine substituent. Providing an excellent repairable 'underfill resin composition by successfully solvating with a specific solvent, and succeeding in causing swelling. ).
- Patent Document 1 JP-A-7-102225
- Patent Document 2 JP 2002-60594 A
- Patent Document 3 Japanese Patent Laid-Open No. 2002-60464
- the adhesive for joining electronic components described in Patent Document 1 has thixotropic properties and is therefore suitable for fluidity as an underfill. It is desirable for the fill to have flow characteristics that do not depend on the slip rate.
- the underfill resin composition described in Patent Documents 2 and 3 has a high curing temperature of about 150 ° C, and heat resistance of electronic parts such as crystal units and plastic parts as well as BGA and CSP. It was not enough to satisfy the low-temperature curability of 120 ° C or less, particularly preferably 100 ° C or less, which is necessary when components with poor performance are mounted together. In general, when trying to develop low-temperature curability, it is customary to add a large amount of curing agent or curing accelerator, but this impairs the pot life during underfill injection. I never liked it.
- the present invention has been made in view of such circumstances, has flow characteristics with little dependence on shear rate (small titasotropy), can be cured at low temperature, and is once underfilled. Even if it is an electronic component device that has a faulty electrical connection after it has been removed, it is possible to remove residues, and it is easy to repair and has a low-viscosity, one-component, solvent-free composition that also has excellent long-life time It is an object of the present invention to provide a liquid epoxy resin composition in which an electronic component device having a connected mounting structure is highly reliable.
- the liquid epoxy resin composition of the present invention is a state in which a connection electrode portion provided in a semiconductor device and a connection electrode portion provided in a circuit board are opposed to each other.
- the inventor of the present invention provides a liquid epoxy resin composition that is an underfill material for sealing a gap between a circuit board and a semiconductor device (semiconductor package).
- a liquid epoxy resin composition that is an underfill material for sealing a gap between a circuit board and a semiconductor device (semiconductor package).
- the cured product of a specific epoxy resin composition is solvated by a specific solvent and subsequently swells, resulting in a decrease in the film strength and a decrease in adhesive strength of the cured product that is a sealing resin. It was found that the body can be mechanically peeled off and the semiconductor knockout can be repaired.
- the above liquid phenolic resin acts as a curing agent for the liquid epoxy resin, and lowers the solubility parameter (SP value) of the cured product. Therefore, solvation with a specific solvent and subsequent swelling occur. Easily succeeded and developed repair sexuality.
- the solid dispersion type amine adduct curing accelerator powder particles [component (C)] and the inorganic filler [component (E)] coexist, the amine silane coupling agent [(D)
- the solid dispersion type amine adduct type curing accelerator powder particles (component (C)) are usually provided with flow characteristics that are less dependent on the shear rate (small titasotropy! /).
- the present inventors have found that it has excellent curing potential and long pot life, unlike the above-mentioned dissolution type curing accelerator.
- the present invention together with the components (A) and (B) used to seal the gap between the circuit board and the semiconductor device, promotes solid dispersion-type amine adduct system curing acceleration.
- Liquid epoxy resin composition containing agent powder particles [component (C)], an amine-based silane coupling agent [component (D)] and an inorganic filler [component (E)].
- the above liquid epoxy resin composition is a low viscosity liquid epoxy resin composition having a large effect of low slip rate dependency (low thixotropy), so that the gap filling property between the semiconductor device and the circuit board is high. Even after curing, it is easily solvated and swollen with a specific organic solvent at room temperature.
- the electronic component device obtained by resin sealing using the liquid epoxy resin composition of the present invention has excellent connection reliability, and even when a connection failure occurs due to misalignment between electrodes, An electronic component device having excellent repair properties can be obtained without discarding the electronic component device itself.
- the surface-coated with an amine-based silane coupling agent in particular, a spherical particle with an average particle diameter of 10 m or less, surface-coated with an amine-based silane coupling agent
- silica particles when silica particles are used, the liquid epoxy resin composition cured product will be more excellent in reducing thermal stress and improving mechanical strength due to a decrease in the coefficient of linear expansion.
- FIG. 1 is a cross-sectional view schematically showing a configuration of an electronic component device.
- the liquid epoxy resin composition of the present invention comprises liquid epoxy resin (component A) and liquid phenolic resin (component B), as well as solid dispersion type amine adduct curing accelerator powder particles (C component). ), An amine-based silane coupling agent (component D), and an inorganic filler (component E).
- liquid is 2 A liquid that exhibits fluidity at 5 ° C. That is, the viscosity at 25 ° C is in the range of 0. OlmPa's to LOOOOPa's. The viscosity can be measured using, for example, an EMD type rotational viscometer.
- the liquid epoxy resin (component A) is not particularly limited as long as it is a liquid epoxy resin containing two or more epoxy groups in one molecule.
- a liquid epoxy resin containing two or more epoxy groups in one molecule for example, bisphenol A type, Various liquid epoxy resins such as bisphenol F type, hydrogenated bisphenol A type, bisphenol AF type, phenol novolac type, and derivatives thereof, polyhydric alcohols and epichlorohydrin derivatives, and liquid epoxy resins derived therefrom and derivatives thereof.
- Glycidylamine type hydantoin type, aminophenol type, arlin type, toluidine type glycidyl type liquid epoxy resin and its derivatives (Practical Plastic Dictionary Editorial Committee, Practical Plastic Dictionary Materials, (First edition, 3rd edition, published on April 20, 1996, pages 211-225) and these liquid epoxy resins Liquid mixture of various glycidyl type solid-type epoxy ⁇ the like. These may be used alone or in combination of two or more.
- the liquid phenol resin (component B) functions as a curing agent for the liquid epoxy resin (component A), and is a liquid phenol having two or more hydroxyl groups in one molecule.
- a liquid phenol resin represented by the following general formula (1) is preferably used as long as it is a novolak.
- N is a positive integer from 0 to 5.
- a arylphenol represented by the formula (1) that exhibits a liquid state at 25 ° C.
- a low molecular weight compound of a copolymer of phenol / formaldehyde resin and phenol / formaldehyde resin is preferably used.
- the use of a liquid phenolic resin having a viscosity at 25 ° C. of 500 dPa's or less, particularly lOOdPa ⁇ s or less, is also preferably used from the viewpoint of reducing the viscosity of the one-component solventless epoxy resin composition.
- a mixture of liquid phenol resin represented by the following structural formulas ( ⁇ ) and ( ⁇ ) is preferably used.
- n is 0 or a positive integer
- m is 0 or a positive integer
- the blending ratio of the liquid epoxy resin (component A) and the liquid phenol resin (component B) is such that the liquid epoxy resin (component A) has one liquid group as described above. It is preferable to set the number of active hydrogens in phenol resin (component B) in the range of 0.4 to 1.6. More preferably, it is in the range of 0.6 to 1.4. That is, if the number of active hydrogens per epoxy group is less than 0.4 or exceeds 1.6, the glass transition temperature of the cured liquid epoxy resin composition tends to decrease, which is not preferable. Because.
- the solid dispersion type amine adduct type curing accelerator powder particles (C component) used together with the above A component and B component are produced, for example, according to a known method described in JP-A-7-196776. Things can be raised.
- the solid dispersion-type amine adduct curing accelerator powder particles (component C) are curing accelerators that are insoluble in the liquid epoxy resin (component A) at room temperature and are solubilized by heating. It functions as a curing accelerator.
- a reaction product of an amine compound and an epoxy compound (amine epoxy adduct), an amine compound and an isocyanate compound or a urea compound are examples of a reaction product of an amine compound and an epoxy compound (amine epoxy adduct), an amine compound and an isocyanate compound or a urea compound.
- room temperature usually refers to a range of about 10 to 40 ° C.
- the epoxy compound used to obtain the reaction product of the amine compound and the epoxy compound (amine epoxy adduct) is a liquid epoxy containing two or more epoxy groups in one molecule.
- amine epoxy adduct a liquid epoxy containing two or more epoxy groups in one molecule.
- bisphenol A type, bisphenol F type, hydrogenated bisphenol A type, bisphenol AF type as described in the previous liquid epoxy resin (component A).
- liquid epoxy resins such as phenol novolac type and derivatives thereof, polyhydric alcohol and epichlorohydrin derived liquid epoxy resin and derivatives thereof, glycidylamine type, hydantoin type, aminophenol type, -Various glycidyl type liquid epoxy resins such as phosphorus type and toluidine type and their derivatives (Edited by Practical Plastic Dictionary Editor, "Lustic Dictionary Material", first edition, third edition, published on April 20, 1996, pages 211 to 225) and liquid mixtures of these liquid epoxy resins and various glycidyl type solid epoxy resins. I can get lost. These may be used alone or in combination of two or more.
- the amine compound used in the production of the solid dispersion type amine adduct curing accelerator powder particles includes an active hydrogen capable of addition reaction with an epoxy group or an isocyanate group in one molecule.
- an active hydrogen capable of addition reaction with an epoxy group or an isocyanate group in one molecule.
- diethylenetriamine triethylenetetramine
- n-propylamine 2-hydroxyethylaminopropylamine
- cyclohexylamine dimethylaminopropylamine
- dibutylaminopropylamine dimethylaminoethylamine
- jetyla A primary or secondary amine having a tertiary amino group in the molecule such as minoetilamine, N-methylamine, N, N dimethylbenzylamine, amine compounds such as N-methylpiperazine, imidazole compounds, etc.
- examples of the isocyanate compound used in the production of the solid dispersion-type amine adduct curing accelerator powder particles include n-butyl isocyanate, isopropino isocyanate, phenol, and the like.
- -Monofunctional isocyanate compounds such as noreisocyanate and pendinoreisocyanate, hexamethylene diisocyanate, toluylene diisocyanate, 1, 5 naphthalene diisocyanate, diphenylenomethane 4, 4 '- And polyfunctional isocyanate compounds such as diisocyanate, isophorone diisocyanate, and xylylene diisocyanate. These may be used alone or in combination of two or more.
- the solid dispersion-type amine adduct curing accelerator powder particles (component C) of the present invention are, for example, a mixture of the above epoxy compound or isocyanate compound and each component of the above amine compound. It can be produced by reacting at room temperature to 200 ° C and then pulverizing the cooled and solidified material. Alternatively, it can be produced by reacting each of the above components in a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc., removing the solvent, and then similarly pulverizing the solid.
- the particle size of the pulverized particles is not particularly limited, but for example, the average particle size is preferably 10 to 20 m.
- the content of the solid dispersion-type amine adduct curing accelerator powder particles (component C) is not particularly limited, but a ratio at which a desired curing rate can be obtained with respect to liquid phenol resin (component B). It is preferable to set as appropriate. For example, the usage amount can be easily determined while measuring the gel time with a hot platen as an index of the curing rate. As an example, it is preferable to set it in the range of 10 to 50 parts, more preferably 15 to 30 parts, especially 100 parts by weight (hereinafter referred to as “parts”) of liquid phenol resin (component B). It is preferable to set it to 20 to 25 parts in that a fast curing reactivity at about 80 to 100 ° C. can be obtained.
- the amine-based silane coupling agent (D component) used together with the components A to C is not particularly limited as long as it is a silane coupling agent having a primary amino group or a secondary amino group.
- N-2 (aminoethyl) 3 aminopropyltriethoxysilane N-2 (aminoethyl) 3 aminopropylmethyldimethoxysilane, and N-2 (aminoethyl) 3 aminopropyltrimethoxysilane were used. It is preferable to use it because the effect of low shear rate dependency (low thixotropy) is large.
- the content of the amine-based silane coupling agent (component D) is preferably set in the range of 0.05 to 3.0 parts with respect to 100 parts of the inorganic filler (component E). More preferably, setting to 0.1 to 1.0 parts is also suitable for maintaining the pot life for a long time.
- the inorganic filler (E component) used together with the above components A to D includes silica powder such as synthetic silica and fused silica, alumina, silicon nitride, aluminum nitride, boron nitride, magnesium, calcium silicate, hydroxide Various powders such as magnesium, aluminum hydroxide, and titanium oxide are listed.
- silica powder such as synthetic silica and fused silica, alumina, silicon nitride, aluminum nitride, boron nitride, magnesium, calcium silicate, hydroxide
- Various powders such as magnesium, aluminum hydroxide, and titanium oxide are listed.
- it is particularly preferable to use spherical silica powder because the effect of reducing the viscosity of the liquid epoxy resin composition is large.
- those having an average particle size of 10 m or less are preferably used together with the maximum particle size, and those having an average particle size of 1 to 5 m are particularly preferably used.
- the maximum particle diameter and the average particle diameter can be measured using, for example, a laser diffraction / scattering particle size distribution analyzer.
- the inorganic filler (E component) it is preferable to use a material whose surface is coated with an amine-based silane coupling agent represented by the following general formula (2). More preferably, spherical silica particles with an average particle diameter of 10 m or less are coated, and particularly preferably, spherical silica particles with an average particle diameter of 1 to 5 m coated with the above surface are used.
- an amine-based silane coupling agent represented by coating the surface of the spherical silica particles with the above-mentioned amine-based silane coupling agent, interaction with liquid epoxy resin (component A) and the like such as wettability is achieved. Dispersibility is improved and viscosity is reduced.
- amine-based silane coupling agents represented by the above general formula (2) include N-2 (aminoethyl) 3 aminopropyl monomethyldimethoxysilane, N-2 (aminoethyl) 3 aminopropyl monotriethoxysilane. N-2 (aminoethyl) 3 aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane and the like. These may be used alone or in combination of two or more.
- the content of the inorganic filler (component E) is preferably set in the range of 10 to 70% by weight of the total liquid epoxy resin composition, particularly preferably 30 to 60% by weight. .
- the blending amount is less than 10% by weight, the effect of reducing the linear expansion coefficient of the cured liquid epoxy resin composition is small.
- the blending amount exceeds 70% by weight, the viscosity of the liquid epoxy resin composition is low. This is because the tendency to increase is not preferable.
- a reactive diluent can be appropriately blended for the purpose of reducing the viscosity or the like, but this reactive diluent may contain a volatile low-boiling compound.
- the liquid epoxy resin composition which is an underfill resin, should be used after removing in advance the volatile evaporative low-boiling compounds that cause voids in the sealed resin layer at a predetermined curing temperature. is there.
- the reactive diluent itself is volatile, voids are likely to occur in the sealing resin layer at a predetermined curing temperature of the liquid epoxy resin composition that is an underfill resin. Reactive diluents are limited in use.
- Examples of the reactive diluent include n-butyl daricidyl ether, allyl glycidyl ether, 2-ethyl hexyl glycidyl ether, styrene oxide, phenol glycidyl ether, cresyl glycidyl ether, lauryl glycidyl ether, p sec butylphenol glycidyl ether, norphenol glycidyl ether, strength glycidyl ether of rubinol, glycidyl metatalylate, burcyclohexene mono Epoxide, pinene oxide, glycidyl ether of tertiary carboxylic acid, diglycidyl ether, glycidyl ether of (poly) ethylene glycol, glycidyl ether of (poly) propylene glycol, bisphenol A with propylene oxide, bisphenol A -Type epoxy resin and
- the liquid epoxy resin composition of the present invention includes, in addition to the above components, flame retardants such as antimony trioxide, antimony pentoxide, antimony bromide, brominated epoxy resin, A low-stressing agent such as glycerin, a coloring agent, and the like can be appropriately blended without departing from the spirit of the present invention.
- flame retardants such as antimony trioxide, antimony pentoxide, antimony bromide, brominated epoxy resin
- a low-stressing agent such as glycerin, a coloring agent, and the like can be appropriately blended without departing from the spirit of the present invention.
- the liquid epoxy resin composition of the present invention can be produced, for example, as follows. That is, the liquid epoxy resin (component A), liquid phenol resin (component B), solid-dispersed amine adduct curing accelerator powder particles (component C), amine silane coupling agent (component D), and inorganic substance A predetermined amount of each component such as filler (E component) and other additives is blended as required, and this is mixed and dispersed under high shear force such as a three roll or homomixer, and sometimes under reduced pressure.
- the desired one-component solvent-free liquid epoxy resin composition can be produced by defoaming.
- connection electrode portions (solder bumps) in advance and a printed circuit board having connection electrode portions (solder pads) facing the solder bumps are connected by solder metal.
- a one-component, non-solvent liquid epoxy resin composition is filled and thermally cured to form a sealed resin layer. Seal with grease.
- the connection electrode portions (solder bumps) 3 provided on the semiconductor package 1 and the wiring circuit board 2 were provided.
- the semiconductor package 1 is mounted on the printed circuit board 2 with the connecting electrode portions (solder pads) 5 facing each other, and the gap between the wired circuit board 2 and the semiconductor package 1 is the liquid epoxy resin composition.
- An electronic component device that is sealed with a sealed resin layer 4 is produced.
- the liquid epoxy resin composition When the liquid epoxy resin composition is filled in the gap between the semiconductor package 1 and the printed circuit board 2, first, the liquid epoxy resin composition is filled in a syringe, and then the semiconductor package 1 of the semiconductor package 1 is filled.
- One end of the liquid epoxy resin composition is extruded and applied at a force of one dollar, and is filled using capillary action.
- filling and sealing on a hot plate heated to about 40 to 80 ° C reduces the liquid viscosity, making it easier to fill and seal. It becomes. Furthermore, if the wiring circuit board 2 is inclined, it becomes easier to fill and seal.
- the air gap distance between the semiconductor package 1 and the printed circuit board 2 in the electronic component device thus obtained is generally about 200 to 300 / ⁇ ⁇ .
- the semiconductor package 1 is not particularly limited as long as it has a connecting electrode portion (solder bump) 3 and can be mounted on the printed circuit board 2.
- BGA Ball 'grid' arrays and CSPs (chip 'scale' package or chip size 'package) are useful.
- the cured epoxy resin composition of the resin-encapsulated portion of the electronic component device obtained as described above swells with a specific organic solvent even after being cured, and the adhesive strength is reduced. The parts device can be repaired.
- the specific organic solvent is preferably a ketone solvent, a glycol diether solvent, a nitrogen-containing solvent, or the like. These may be used alone or in combination of two or more.
- ketone solvents include: acetophenone, isophorone, ethyl ⁇ -butyl ketone, diisoptyl ketone, jetyl ketone, cyclohexyl ketone, di- ⁇ propyl ketone, methyl oxide, methyl- ⁇ amyl ketone, methyl isobutyl ketone, methyl ethyl ketone, and methylcyclohexane.
- glycol gel solvent examples include ethylene glycol jetyl ether, Ethylene glycol dibutyl ether, ethylene glycolo-resin chineno ethenore, jetylene glycol oleetino retino chinenoate, diethylene glucono les chineno lee tenole, dimethylene glyconores butyleno ethenore, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether Etc. These may be used alone or in combination of two or more.
- nitrogen-containing solvent examples include N, N'-dimethylformamide, N, N'-dimethylacetamide, N-methyl-2-pyrrolidone, N, N'-dimethylsulfoxide, hexamethyl phosphortriamide, and the like. Is given. These may be used alone or in combination of two or more.
- a semiconductor package or a portion corresponding to the repair of a printed circuit board is heated using a hot platen or the like to remove the semiconductor package.
- the heating temperature at this time is a temperature of about + 50 ° C or higher from the glass transition temperature of the cured product of the liquid epoxy resin composition of the present invention, and the melting of the joining metal such as solder.
- the organic solvent is directly applied or the absorbent cotton is impregnated with the organic solvent, and the cured portion of the liquid epoxy resin composition of the wiring circuit board is contacted at room temperature, more preferably glass.
- the printed circuit board and the mounting portion can be reused.
- the semiconductor package to which the residue of the cured product of the liquid epoxy resin composition is adhered is reused by swelling and removing the cured product in the above organic solvent in a predetermined container at room temperature. can do.
- the entire portion of the wiring circuit board to be repaired is directly coated with the organic solvent or the absorbent cotton soaked with the organic solvent.
- the semiconductor package may be removed from the printed circuit board after the organic package is gradually infiltrated into the edge of the semiconductor package to swell the cured body to reduce the strength and adhesion of the cured body. it can.
- Epoxy resin c represented by the following structural formula (a)
- n is an integer of 0 or more. Purity 99%, viscosity 22dPa? S (25 ° C), epoxy equivalent 165 g, eq]
- TPP Triphenylphosphine
- the conduction failure rate immediately after sealing the resin of the electronic component device was measured. After that, using the thermal test equipment, the electronic component device was cycled at 30 ° CZ for 10 minutes and 125 ° C / 10 minutes. The electrical continuity after 1000 cycles was examined, and the continuity failure rate (%) was calculated for all 64 copper wiring pads (substrate side electrodes) of the above-mentioned glass epoxy wiring circuit board.
- the above-mentioned electronic component device force also peeled off the CSP package and returned to room temperature, but the cured epoxy resin composition remained in the connection part
- Absorbent cotton containing a mixed solvent of equal amounts of N, N′-dimethylformamide and diethylene glycol dimethyl ether was allowed to stand in the residue and left at room temperature (22 ° C.) for 1 hour. After that, remove the cotton wool and wipe it with methanol, peel off the cured epoxy resin composition, and re-peel the electronic component device into the pad part of the printed circuit board.
- the CSP package was mounted on the printed circuit board and the electrical continuity was examined. Thereafter, the resin was sealed in the same manner as described above, and the repair (rework) property was evaluated.
- the cured epoxy resin composition can be completely peeled off, and when the electrical connection is complete, it can be peeled with the cured body remaining slightly, but the electrical connection is complete. Yes, when the cured product remains slightly and can be peeled off, but when the electrical connection is incomplete, ⁇ , when the cured epoxy resin composition hardly peels off and the electrical connection is incomplete X.
- Viscosity (at 2 S O 345 500 280 50
- the liquid epoxy resin compositions of all the examples are highly preferable because of their low shear rate dependency (low thixotropy) and are combined with a low viscosity that increases the pot life. It can be seen that it is excellent as a one-component solvent-free liquid epoxy resin composition. It is clear that the seal is also excellent in repairability because the formed sealing resin layer has no conduction failure.
- the liquid epoxy resin composition of the comparative example had no problem with respect to the repair property with no conduction failure, but the liquid epoxy resin composition of Comparative Examples 1 to 6 was Because of the large dependency on the slip rate (thickness, etc.), the time required to fill the gap between the CSP package and the circuit board was extremely long.
- Comparative Example 7 products, the pot life was too short, which hindered filling. Furthermore, in Comparative Example 8, the viscosity was too low because no curing accelerator was used and no inorganic filler was contained, and the results of the drop impact test were extremely poor and the reliability was poor.
- the present invention relates to a semiconductor package and a circuit board via a bump electrode portion for connecting a semiconductor package such as a BGA (ball grid 'array) or a CSP (chip scale' package or chip 'size' package).
- a semiconductor package such as a BGA (ball grid 'array) or a CSP (chip scale' package or chip 'size' package).
- a liquid epoxy resin composition used for filling a gap between a semiconductor package and a circuit board and sealing the resin is provided.
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- Health & Medical Sciences (AREA)
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JP5045985B2 (ja) * | 2006-09-27 | 2012-10-10 | 日立化成工業株式会社 | エポキシ樹脂組成物及び電子部品装置 |
JP2008226926A (ja) * | 2007-03-08 | 2008-09-25 | Sumitomo Bakelite Co Ltd | 液状封止樹脂組成物、半導体装置および半導体装置の製造方法 |
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JPH07196776A (ja) * | 1994-01-07 | 1995-08-01 | Ajinomoto Co Inc | エポキシ樹脂組成物 |
JPH11263826A (ja) * | 1998-01-12 | 1999-09-28 | Shin Etsu Chem Co Ltd | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
JP2002060594A (ja) * | 2000-06-08 | 2002-02-26 | Nitto Denko Corp | 液状エポキシ樹脂組成物 |
JP2002128992A (ja) * | 2000-10-30 | 2002-05-09 | Matsushita Electric Works Ltd | エポキシ樹脂組成物、その製造方法及び半導体装置 |
JP2004123847A (ja) * | 2002-09-30 | 2004-04-22 | Toray Ind Inc | エポキシ樹脂組成物及び半導体装置 |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH07196776A (ja) * | 1994-01-07 | 1995-08-01 | Ajinomoto Co Inc | エポキシ樹脂組成物 |
JPH11263826A (ja) * | 1998-01-12 | 1999-09-28 | Shin Etsu Chem Co Ltd | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
JP2002060594A (ja) * | 2000-06-08 | 2002-02-26 | Nitto Denko Corp | 液状エポキシ樹脂組成物 |
JP2002128992A (ja) * | 2000-10-30 | 2002-05-09 | Matsushita Electric Works Ltd | エポキシ樹脂組成物、その製造方法及び半導体装置 |
JP2004123847A (ja) * | 2002-09-30 | 2004-04-22 | Toray Ind Inc | エポキシ樹脂組成物及び半導体装置 |
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