JPS6320321A - Epoxy resin composition - Google Patents
Epoxy resin compositionInfo
- Publication number
- JPS6320321A JPS6320321A JP16365486A JP16365486A JPS6320321A JP S6320321 A JPS6320321 A JP S6320321A JP 16365486 A JP16365486 A JP 16365486A JP 16365486 A JP16365486 A JP 16365486A JP S6320321 A JPS6320321 A JP S6320321A
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- epoxy resin
- group
- epoxy
- flavan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 15
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 15
- 239000004593 Epoxy Substances 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229930182497 flavan-3-ol Natural products 0.000 claims abstract description 5
- 229920001991 Proanthocyanidin Polymers 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- -1 methoxyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical group C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 abstract description 14
- XIMADJWJJOMVID-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromene-3,4-diol Chemical compound OC1C(O)C2=CC=CC=C2OC1C1=CC=CC=C1 XIMADJWJJOMVID-UHFFFAOYSA-N 0.000 abstract 1
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 abstract 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000007789 sealing Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 description 4
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- XFZJEEAOWLFHDH-NFJBMHMQSA-N procyanidin B2 Chemical compound C1([C@@H]2[C@H](O)[C@H](C3=C(O)C=C(O)C=C3O2)C=2C(O)=CC(O)=C3C[C@H]([C@H](OC3=2)C=2C=C(O)C(O)=CC=2)O)=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-NFJBMHMQSA-N 0.000 description 3
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 description 1
- LIPDUIOSIFXENT-UHFFFAOYSA-N 1,3,5-triazido-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=C(N=[N+]=[N-])C([N+]([O-])=O)=C(N=[N+]=[N-])C([N+]([O-])=O)=C1N=[N+]=[N-] LIPDUIOSIFXENT-UHFFFAOYSA-N 0.000 description 1
- FZQXMGLQANXZRP-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-(3-imidazol-1-ylpropyl)thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCN1C=NC=C1 FZQXMGLQANXZRP-UHFFFAOYSA-N 0.000 description 1
- DDHYZBVBQZYMTO-UHFFFAOYSA-N 1-(dimethylamino)pentan-1-ol Chemical compound CCCCC(O)N(C)C DDHYZBVBQZYMTO-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-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
- 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
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- SIQHSJOKAUDDLN-UHFFFAOYSA-N 2-methyl-1-propylimidazole Chemical compound CCCN1C=CN=C1C SIQHSJOKAUDDLN-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
- WMNWJTDAUWBXFJ-UHFFFAOYSA-N 3,3,4-trimethylheptane-2,2-diamine Chemical compound CCCC(C)C(C)(C)C(C)(N)N WMNWJTDAUWBXFJ-UHFFFAOYSA-N 0.000 description 1
- YJCSUBLMBRTUOX-UHFFFAOYSA-N 3,3,4-trimethylhexane-2,2-diamine Chemical compound CCC(C)C(C)(C)C(C)(N)N YJCSUBLMBRTUOX-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
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002350 Procyanidin B2 Polymers 0.000 description 1
- 229920000124 Prodelphinidin Polymers 0.000 description 1
- 229930182448 Prodelphinidin Natural products 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- FWLORMQUOWCQPO-UHFFFAOYSA-N benzyl-dimethyl-octadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 FWLORMQUOWCQPO-UHFFFAOYSA-N 0.000 description 1
- AFBPHRMRBXPVPX-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;acetate Chemical compound CC([O-])=O.CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 AFBPHRMRBXPVPX-UHFFFAOYSA-M 0.000 description 1
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 1
- GLROGUSVUGSGPO-UHFFFAOYSA-N bis(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1C2OC2CC(C)C1OC(=O)CCCCC(=O)OC1CC2OC2CC1C GLROGUSVUGSGPO-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 235000019241 carbon black Nutrition 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- YIFWXQBNRQNUON-UHFFFAOYSA-M dodecyl(trimethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCC[N+](C)(C)C YIFWXQBNRQNUON-UHFFFAOYSA-M 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- VUWDAOLDXOYMIZ-UHFFFAOYSA-N nonadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCC[NH3+] VUWDAOLDXOYMIZ-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】
【産業上の利用分野〕
本発明は、エポキシ樹脂組成物に係り、特に、金属、例
えば、アルミニウムの防蝕性にずくれた性能をもつ、樹
脂酸物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to epoxy resin compositions, and more particularly to resin oxides that have superior corrosion resistance to metals, such as aluminum.
樹脂封止型半導体装置は、主として、ノボラック型フェ
ノール樹脂を硬化剤としたエポキシ樹脂系組成物で封止
されている。しかし、この半導体装置を高置高湿下に放
置した場合、樹脂バルク中や、樹脂とリード線、素子と
の隙間を通じて外部の水分が、パッケージ内部に浸入し
、素子上のアルニウム（ＡＩ２と記す）配線、ボンディ
ングバンド部のＡＱを腐食し、断線させる問題がある。Resin-sealed semiconductor devices are mainly encapsulated with an epoxy resin composition using a novolac type phenol resin as a curing agent. However, if this semiconductor device is left at a high location and under high humidity, moisture from the outside will infiltrate into the package through the resin bulk and the gaps between the resin, lead wires, and elements, resulting in aluminum (denoted as AI2) on the elements. ) There is a problem in that the AQ of the wiring and bonding band portion is corroded and disconnected.
この対策として、樹脂バルク中の疎水化、素子表面のカ
ップリング剤処理、あるいは、樹脂硬化物の低応力化、
素材の高純度化（イオン性不純物の除去）などの対策が
とられてきた。Countermeasures include making the resin bulk hydrophobic, treating the element surface with a coupling agent, or reducing the stress of the cured resin.
Measures have been taken to improve the purity of the material (removal of ionic impurities).
しかし、セラミックス封止半導体導体装置が従来用いら
れてきた分野へも、その低コスト化を図る上から、樹脂
封止型半導体装置の用途拡大が進んでおり、樹脂封止型
半導体装置には、更に優れた耐湿信頼性の付与が必要と
なってきている。However, in order to reduce costs, the use of resin-encapsulated semiconductor devices is expanding into fields where ceramic-encapsulated semiconductor conductor devices have traditionally been used. It has become necessary to provide even better moisture resistance reliability.
本発明の目的は、高温高湿下で信頼性の高い動作が可能
な半導体装置を提供することにある。An object of the present invention is to provide a semiconductor device that can operate with high reliability under high temperature and high humidity conditions.
本発明の要旨は、
１、多官能エポキシ化合物と、一般式
％式％
〔式中、Ｒｚは水素または水酸基、Ｒｚ、 Ｒａ、 Ｒ
４は水素、水酸基またはメトキシル基、Ｒｓは水素、ガ
ロイル基、または、グリコビラジノル基である、〕で表
わされるフラバン−３−オール、または、フラバン−３
，４−ジオールを構成単位としたニないし十重量体の群
より選ばれた少なくとも一種のプロアントシアニジンと
を含むことを特徴とするエポキシ樹脂組成物、
２、多官能エポキシ化合物と、一般式
０式％
〔式中、Ｒ１は水素または水酸基、Ｒｘ 、 Ｒｓ 。The gist of the present invention is as follows: 1. A polyfunctional epoxy compound and a general formula % [wherein Rz is hydrogen or a hydroxyl group, Rz, Ra, R
4 is hydrogen, a hydroxyl group or a methoxyl group, Rs is hydrogen, a galloyl group, or a glycobyradinol group] or flavan-3
, an epoxy resin composition comprising at least one type of proanthocyanidin selected from the group of di- to deca-heavy compounds having 4-diol as a constituent unit; 2. a polyfunctional epoxy compound; and a polyfunctional epoxy compound having the general formula 0 % [In the formula, R1 is hydrogen or a hydroxyl group, Rx, Rs.
Ｒ４は水素、水酸基またはメトキシル基、Ｒ５は水素、
ガロイル基、または、グリコビラジノル基である。〕で
表わされるフラバン−３−オール、または、フラバン−
３，４−ジオールを構成単位としたニないし中量体の群
より選ばれた少なくととも一種のプロトシアニジンとを
含むエポキシ樹脂組成物を用いて、半導体素子及びリー
ド線の少なくとも一部を被覆、および／または封止成形
してなることを特徴とする半導体装置である。R4 is hydrogen, hydroxyl group or methoxyl group, R5 is hydrogen,
It is a galloyl group or a glycovirazinol group. ] Flavan-3-ol or flavan-3-ol represented by
At least a portion of the semiconductor element and the lead wires are coated with an epoxy resin composition containing at least one protocyanidin selected from the group of di- or intermediates having 3,4-diol as a constituent unit. This is a semiconductor device characterized by being formed by , and/or sealing molding.
本発明でいう多官能エポキシ化合物には、例えば、ビス
フェノールＡのグリシジルエーテル、ブタジエンジエポ
キサイド、３，４−エポキシシクロへキシルメチル−（
３，４−エポキシ）シクロヘキサンカルボキシレート、
ビニルシクロヘキサンジオキサイド、４，４′−ジ（１
，２−エポキシエチル）ジフェニルエーテル、２，２−
ビス（３，４−エポキシシクロヘキシル）プロパン、レ
ゾルシンのグリシジルエーテル、フロログルシーンのジ
グリシジルエーテル、メチルフロログルシンのジグリシ
ジルエーテル、ビス−（２，３−エポキシシクロペンチ
ル）エーテル、２− （３゜４−エポキシ）シクロヘキ
サン−５，５−スピロ（３，４−エポキシ）シクロヘキ
サン−ｍ−ジオキサン、ビス−（３，４−エポキシ−６
−メチルシクロヘキシル）アジペート、Ｎ ＋ Ｎ ’
ｍ−フェニレンビス（４，５−エポキシ−１，２−
シクロヘキサンジカボキシイミドなどの三官能のエポキ
シ化合物、パラアミノフェノールのトリグリシジルエー
テル、ポリアリルグリシジルエーテル、１．３．５−ト
リ（１，２−エポキシエチル）ベンゼン、２．２’、４
．４’−テトラグリシドキシベンゾフェノン、フェノー
ルホルムアルデヒドノボラック樹脂のポリグリシジルエ
ーテル、グリセリンのトリグリシジルエーテル、トリメ
チロールプロパンのトリグリシジルエーテなどの三官能
以上のエポキシ化合物、また、臭素化エポキシ等のハロ
ゲン化エポキシ化合物、あるいは、ヒダントインエポキ
シ化合物が用いられる。The polyfunctional epoxy compounds referred to in the present invention include, for example, glycidyl ether of bisphenol A, butadiene diepoxide, 3,4-epoxycyclohexylmethyl-(
3,4-epoxy)cyclohexane carboxylate,
Vinyl cyclohexane dioxide, 4,4'-di(1
,2-epoxyethyl)diphenyl ether, 2,2-
Bis(3,4-epoxycyclohexyl)propane, glycidyl ether of resorcinol, diglycidyl ether of phloroglucine, diglycidyl ether of methylphloroglucine, bis-(2,3-epoxycyclopentyl) ether, 2- (3゜4-epoxy)cyclohexane-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, bis-(3,4-epoxy-6
-methylcyclohexyl)adipate, N + N'
m-Phenylenebis(4,5-epoxy-1,2-
Trifunctional epoxy compounds such as cyclohexanedicaboximide, triglycidyl ether of para-aminophenol, polyallyl glycidyl ether, 1.3.5-tri(1,2-epoxyethyl)benzene, 2.2', 4
．． Tri- or higher functional epoxy compounds such as 4'-tetraglycidoxybenzophenone, polyglycidyl ether of phenol formaldehyde novolac resin, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, and halogenated epoxy such as brominated epoxy. or a hydantoin epoxy compound.
本発明において、 一般式 ％式％ 〔式中、Ｒ１は水素または水酸基、Ｒｚ 、 Ｒａ 。In the present invention, general formula %formula% [In the formula, R1 is hydrogen or a hydroxyl group, Rz, Ra.
Ｒ４は水素、水酸基またはメトキシル基、Ｒ５は水素、
ガロイル基またはグリコピラノシル基である。〕で表わ
されるフラバン−３−オール、またはフラバン−３，４
−ジオールを構成単位としたニないし中量体の群より選
ばれた少なくととも一種であるプロアントシアニジンと
は、例えば、カテキンガレート
などがある。上記化合物の一種以上を併用して用いるこ
とも出来る。R4 is hydrogen, hydroxyl group or methoxyl group, R5 is hydrogen,
It is a galloyl group or a glycopyranosyl group. ] Flavan-3-ol or flavan-3,4
- Proanthocyanidins, which are at least one type selected from the group of di- or intermediates having diol as a constituent unit, include, for example, catechin gallate. One or more of the above compounds can also be used in combination.
本発明のエポキシ樹脂組成物には公知の硬化剤が併用さ
れる。それには、垣内弘著；エポキシ樹脂（昭和４５年
９月発行）１０９〜１４９ページ、Ｌｅｅ、 Ｎｅｖｉ
ｌｌｅ著；Ｅｐｏｘｙ Ｒｅｓｉｎｓ（Ｍｅ Ｇｒａｙ
−ＨｌｌｌＢｏｏｋ Ｃｏｍｐａｎｙ Ｉｎｃ、 Ｎ
ｅｔ＋ Ｙｏｒｋ、 １９５７年発行）６３〜１４１ペ
ージ、Ｐ 、 Ｅ 、 Ｂｒｕｎｌｓ著； Ｅｐｏｘｙ
Ｒｅｓｉｎｓ Ｔｅｃｈｎｏｌｏｇｙ （Ｉｎｔｅｒｂ
ｃｉｅｎｃｅ Ｐｕｂｌｉｓｈｅｒｓ。A known curing agent is used in combination with the epoxy resin composition of the present invention. For that, Hiroshi Kakiuchi; Epoxy Resin (published September 1970) pages 109-149, Lee, Nevi
Epoxy Resins (Me Gray
-HllBook Company Inc, N
et+ York, 1957) pages 63-141, by P. E. Brunls; Epoxy
Resins Technology (Interb
science Publishers.
Ｎｅｗ Ｙｏｒｋ、 １９６８年発行）４５−１１１ペ
ージなどに記載の化合物であり、例えば、脂肪族ポリア
ミン、を含むアミン類、カルボン酸類、 （トリメリッ
ト酸トリグリセライド（リカレジン・ＴＮＴＡなど）を
含む）カルボン酸無水物類、脂肪族および芳香族ポリア
ミドオリゴマーおよびポリマー類、三フッ化ホウ素−ア
ミンコンプレックス類、フェノール樹脂、メラミン樹脂
、ウレア樹脂、ウレタン樹脂などの合成樹脂初期縮合物
類、その他、ジシアンジアミド、カルボン酸ヒドラジド
、ポリアミノマレイミド類などがある。New York, published in 1968), pages 45-111, etc., such as aliphatic polyamines, amines including carboxylic acids, carboxylic acid anhydrides (including trimellitic acid triglyceride (Recaresin, TNTA, etc.)) aliphatic and aromatic polyamide oligomers and polymers, boron trifluoride-amine complexes, synthetic resin initial condensates such as phenolic resins, melamine resins, urea resins, and urethane resins, others, dicyandiamide, carboxylic acid hydrazide , polyaminomaleimides, etc.
これら硬化剤は、用途、目的に応じて一種以上使用する
ことが出来る。One or more types of these curing agents can be used depending on the use and purpose.
特に、フェノールボラック樹脂は、硬化樹脂の金属イン
サートに対する密着性、成形時の作業性などの点から、
半導体封止用材料の硬化剤成分として、好適である。In particular, phenol borac resin is highly effective in terms of adhesion of the cured resin to metal inserts and workability during molding.
It is suitable as a curing agent component for semiconductor encapsulation materials.
樹脂組成物には、エポキシ化合物とノボラック型フェノ
ール樹脂の硬化反応を促進する効果が知られている公知
の触媒を使用することが出来る。For the resin composition, a known catalyst known to be effective in accelerating the curing reaction between an epoxy compound and a novolac type phenol resin can be used.
さらに、エポキシ樹脂組成物の硬化反応を促進するため
、各種の触媒を添加することができ、この触媒には、例
えば、トリエタノールアミン、テトラメチルブタンジア
ミン、テトラメチルペンタンジアミン、テトラメチルヘ
キサンジアミン、トリエチレンジアミン及びジメチルア
ニリン等の第三級アミン、ジメチルアミノエタノール及
びジメチルアミノペンタノール等のオキシアルキルアミ
ンならびにトリス（ジメチルアミノメチル）フェノール
及びメチルモルホリン等のアミン類を適用することがで
きる。Furthermore, in order to accelerate the curing reaction of the epoxy resin composition, various catalysts can be added, such as triethanolamine, tetramethylbutanediamine, tetramethylpentanediamine, tetramethylhexanediamine, Tertiary amines such as triethylenediamine and dimethylaniline, oxyalkylamines such as dimethylaminoethanol and dimethylaminopentanol, and amines such as tris(dimethylaminomethyl)phenol and methylmorpholine can be applied.
又、同じ目的で、触媒として、例えば、セチルトリメチ
ルアンモニウムブロマイド、セチルトリメチルアンモニ
ウムクロライド、ドデシルトリメチルアンモニウムアイ
オダイド、トリメチルドデシルアンモニウムクロライド
、ベンジルジメチルテトラデシルアンモニウムクロライ
ド、ペンジルメチルパルミチルアンモニウムクロライド
、アリルドデシルトリメチルアンモニウムブロマイド、
ベンジルジメチルステアリルアンモニウムプロマイト、
ステアリルメチルアンモニウムクロライド及びベンジル
ジメチルテトラデシルアンモニウムアセテート等の第四
級アンモニウム塩を適用することができ、更には、２−
ウンデシルイミダゾール、２−メチルイミダゾール、２
−エチルイミダゾール、２−ヘプタデシルイミダゾール
、２−メチル−４−エチルイミダゾール、１−ブチルイ
ミダゾール、１−プロピル−２−メチルイミダゾール、
１−ベンジル−２−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、ｌ−シアノエチル−２−フ
ェニルイミダゾール、１−アジン−２−メチルイミダゾ
ール及び１−アジン−２ウンデシルイミダゾール等のイ
ミダゾール化合物あるいは又、トリフェニルホスフィン
テトラフェニルボレート、トリエチルアミンテトラフェ
ニルボレート、Ｎ−メチルモルホリンテトラフェニルボ
レート、ピリジンテトラフェニルボレート２−一エチル
ー４−メチルイミダゾールテトラフェニルボレート及び
２−エチル−１，４−ジメチルイミダゾールテトラフェ
ニルボレート等のテトラフ二二ルボロン塩等が有用であ
る。For the same purpose, as a catalyst, for example, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, dodecyltrimethylammonium iodide, trimethyldodecylammonium chloride, benzyldimethyltetradecylammonium chloride, pendylmethylpalmitylammonium chloride, allyldodecyltrimethyl ammonium bromide,
benzyldimethylstearylammonium promite,
Quaternary ammonium salts such as stearylmethylammonium chloride and benzyldimethyltetradecylammonium acetate can be applied, as well as 2-
Undecylimidazole, 2-methylimidazole, 2
-ethylimidazole, 2-heptadecylimidazole, 2-methyl-4-ethylimidazole, 1-butylimidazole, 1-propyl-2-methylimidazole,
1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2
- imidazole compounds such as undecylimidazole, l-cyanoethyl-2-phenylimidazole, 1-azine-2-methylimidazole and 1-azine-2 undecylimidazole, or also triphenylphosphine tetraphenylborate, triethylamine tetraphenylborate, Tetrahinyl boron salts such as N-methylmorpholine tetraphenylborate, pyridine tetraphenylborate, 2-1ethyl-4-methylimidazole tetraphenylborate, and 2-ethyl-1,4-dimethylimidazole tetraphenylborate are useful.
これら触媒はその二種以上を併用することもでき、その
量は、多官能エポキシ化合物（Ａ） １００に対して、
重量比で、０．０１〜２０の範囲で用いればよい。These catalysts can also be used in combination of two or more, and the amount thereof is as follows:
It may be used in a weight ratio of 0.01 to 20.
本発明では樹脂組成物に、目的と用途に応じて、各種の
無機物質や添加剤を配合して用いることが出来る。それ
らの具体例は、ジルコン、シリカ、溶融石英ガラス、ア
ルミナ、水酸化アルミニウム、ガラス、石英ガラス、ケ
イ酸カルシウム、石コウ、炭酸カルシウム、マグネサイ
ト、クレー、カオリン、タルク、鉄粉、銅粉、マイカ、
アスベスト、炭化珪素、窒化ホウ素、二硫化モリブデン
、鉛化合物、鉛酸化物、亜鉛華、チタン白、カーボンブ
ラックなどの充填剤、あるいは、高級脂肪酸、ワックス
類などの離型剤、エポキシシラン、ビニルシラン、アミ
ノシラン、ボラン系化合物、アルコキシチタネート系化
合物、アルミニウムキレート化合物などのカップリング
剤などである。さらに、アンチモン、燐化合物、臭素や
塩素を含む公知の難燃化剤を用いることが出る。In the present invention, various inorganic substances and additives can be added to the resin composition depending on the purpose and use. Specific examples thereof include zircon, silica, fused silica glass, alumina, aluminum hydroxide, glass, quartz glass, calcium silicate, gypsum, calcium carbonate, magnesite, clay, kaolin, talc, iron powder, copper powder, mica,
Fillers such as asbestos, silicon carbide, boron nitride, molybdenum disulfide, lead compounds, lead oxide, zinc white, titanium white, carbon black, mold release agents such as higher fatty acids and waxes, epoxy silane, vinyl silane, Coupling agents such as aminosilane, borane compounds, alkoxytitanate compounds, and aluminum chelate compounds. Additionally, known flame retardants containing antimony, phosphorus compounds, bromine and chlorine may be used.
本発明では、半導体装置を封止するための装置、方法は
特に限定されず、例えば前述の成分からなる組成物をも
って、注型、トランスファ成形など公知の方法が適用で
きる。In the present invention, the apparatus and method for sealing the semiconductor device are not particularly limited, and for example, known methods such as casting and transfer molding can be applied using a composition comprising the above-mentioned components.
なお、本発明に使用される金属キレート化合物と金属ア
ルコレート系化合物とを成分とする組成物から形成され
た保護皮膜は、樹脂封止型のみでなく、ガラス融着セラ
ミック封止や半田融着セラミック封止など他の型の封止
方式による半導体装置にも、同様に適用できる。The protective film formed from the composition containing a metal chelate compound and a metal alcoholate compound used in the present invention can be used not only for resin sealing, but also for glass fusion ceramic sealing and solder fusion sealing. The present invention can be similarly applied to semiconductor devices using other types of sealing methods such as ceramic sealing.
次に実施例によって説明する。Next, an example will be explained.
〈実施例１〜５〉
多官能エポキシ化合物として、トリス（ヒドロキシフェ
ニル）メタンベースの多官能エポキシ化合物、ＸＤ−９
０５３（エポキシ当量、２２５、ダウ・ケミカル社製）
百重量部、
硬化剤として、二量体プロシアニジンＢ−２、二量体プ
ロデルフイニジン、二量体プロシアニジンＢ−１没食子
酸エステル、ガロカテキンガレートの四種類のプロマン
トシアニジン、並びに、ノボラック型フェノール樹脂Ｈ
Ｐ−６０７Ｎ （日立化成社製）、ポリーＰ−ヒドロキ
シスチレン（丸善石油社１！ＪＭレジン、平均分子量４
８００）を第１表に記した所定量、硬化促進剤として、
トリフェニルホスフイン二重量部、カップリング剤とし
て、エポキシシランＫＢＭ３０３ （信越化学社製）二
重置部、難燃剤として、付加型イミドコート赤すン四重
量部、離型剤として、ステアリン酸カルシウム−重量部
とへキストワックスＥ（ヘキストジャパン社１２）−重
量部、充填材として、溶融石英ガラス粉七十五重量パー
セント、着色剤として、カーボンブラック（キャボット
社製）二重置部を添加配合した。<Examples 1 to 5> As a polyfunctional epoxy compound, a tris(hydroxyphenyl)methane-based polyfunctional epoxy compound, XD-9
053 (epoxy equivalent, 225, manufactured by Dow Chemical Company)
100 parts by weight, as a curing agent, four types of promanthocyanidins: dimeric procyanidin B-2, dimeric prodelphinidin, dimeric procyanidin B-1 gallic acid ester, gallocatechin gallate, and novolak type. Phenolic resin H
P-607N (manufactured by Hitachi Chemical Co., Ltd.), poly P-hydroxystyrene (Maruzen Sekiyu Co., Ltd. 1! JM resin, average molecular weight 4
800) in the prescribed amount listed in Table 1 as a curing accelerator,
Two parts by weight of triphenylphosphine, two parts by weight of epoxysilane KBM303 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a coupling agent, four parts by weight of addition-type imide coated red sun as a flame retardant, and calcium stearate as a mold release agent. Parts by weight, Hoechst Wax E (Hoechst Japan Co., Ltd. 12) - parts by weight, 75% by weight of fused silica glass powder as a filler, and double parts of carbon black (manufactured by Cabot) as a coloring agent were added and blended. .
次いで、７０〜８５℃のへインチ径二本ロールで化分間
混練した後、粗粉砕して半導体封止用樹脂組成物を得た
。Next, the mixture was kneaded for a while using two inch-diameter rolls at 70 to 85°C, and then coarsely pulverized to obtain a resin composition for semiconductor encapsulation.
次いで該樹脂組成物は、２５６にビットＤ−ＲＡＭメモ
リＬＳＩの素子を充填した金型をセットしたトランスフ
ァ成形機により、１８０℃。Next, the resin composition was heated to 180° C. using a transfer molding machine equipped with a mold filled with BIT D-RAM memory LSI elements.
７０ｋｇｆ／ａＪ、１．５分の条件で成形された。Molding was carried out under the conditions of 70 kgf/aJ and 1.5 minutes.
得られた樹脂封止型半導体装置は、１２１℃。The temperature of the obtained resin-sealed semiconductor device was 121°C.
２気圧の過飽和水蒸気中（ＰＣＴ）に投入された後、所
定時間毎に取り出し、ＬＳＩの電圧的動作が正常である
か否かをチェックした。After being placed in supersaturated steam (PCT) at 2 atm, the LSI was taken out at predetermined time intervals to check whether the voltage operation of the LSI was normal.
く比較例−６〉
一封止用エポキシ樹脂組成物の作成−
多官能エポキシ化合物として、トリス（ヒドロキシフェ
ニル）メタンベースの多官能エポキシ化合物ＸＤ−９０
５３（ダウ、ゲミカル社製、エポキシ当量、２２５）百
重量部、硬化剤として、ノボラック型フェノール樹脂Ｈ
’Ｐ−６０７Ｎ （日立化成社製、軟化点８３℃）五十
五重量部、硬化促進剤として、トリエチルアミンテトラ
フェニルボレート（ＴＥＡ−Ｋ）三重置部、カップリン
グ剤として、エポキシシランＫＢＭ３０３ （信越化学
社製）二重置部、難燃材として、付加型イミドコート赤
すン五重量部、離型剤として、ステアリン酸カルシウム
−重量部とへキストワックスＥ（ヘキストジャパン社製
）−重量部、充填材として、溶融石英ガラス粉４９０重
量部、着色材として、カーボンブラック（キャボット社
製）二重置部を添加配合した。Comparative Example-6> Creation of epoxy resin composition for sealing- Tris(hydroxyphenyl)methane-based polyfunctional epoxy compound XD-90 as a polyfunctional epoxy compound
53 (manufactured by Dow, Gemical Co., Ltd., epoxy equivalent, 225) 100 parts by weight, novolak type phenolic resin H as a curing agent
'P-607N (manufactured by Hitachi Chemical Co., Ltd., softening point 83°C) 55 parts by weight, triethylaminetetraphenylborate (TEA-K) triple part as a curing accelerator, epoxysilane KBM303 (Shin-Etsu Chemical) as a coupling agent (manufactured by Hoechst Japan Co., Ltd.) double placement part, 5 parts by weight of addition-type imide coat Akasun as a flame retardant, calcium stearate - parts by weight and Hoechst Wax E (manufactured by Hoechst Japan) - parts by weight as mold release agents, filling 490 parts by weight of fused silica glass powder was added as a material, and carbon black (manufactured by Cabot Co., Ltd.) double layer was added as a colorant.
次いで、７０〜８５℃のへインチ径二本ロールで化分間
混練した後、粗粉砕して樹脂組成物を得た。Next, the mixture was kneaded for a while using two inch-diameter rolls at 70 to 85°C, and then coarsely pulverized to obtain a resin composition.
く追加実施例１〜４〉
５００ ｍ Ｑの三角フラスコ中に、２５０ ｍ Ｑの
Ｎ−メチルヒロリドンを採り、ガロカテキンガレートを
第２表の所定の配合量を加え、加熱攪拌して溶解し、四
種類のガロカテキンガレート溶液を作成した。Additional Examples 1 to 4 Into a 500 mQ Erlenmeyer flask, 250 mQ of N-methylhyrrolidone was added, and the predetermined amount of gallocatechin gallate shown in Table 2 was added, and dissolved by heating and stirring. , four types of gallocatechin gallate solutions were prepared.
次いで、これらのそれぞれの溶液に、付加型ポリイミド
としてケルイミドに６０１ （ローン・ブーラン社製
、ビスマレイミド・アミン付加物）、あるいは、アルミ
ニウムキレートカップリング剤ＡＬＣＨ−ＴＲ（用研フ
ァインケミカル社製）をそれぞれ別個に所定量添加して
溶解させ、被覆用組成物を得る。Next, to each of these solutions, 601 (bismaleimide amine adduct, manufactured by Lorne Boulin Co., Ltd.) or an aluminum chelate coupling agent ALCH-TR (manufactured by Yoken Fine Chemical Co., Ltd.) was added to each of these solutions. A predetermined amount is added separately and dissolved to obtain a coating composition.
次いで、２５６にビット［）−ＲＡＭメモリ用ＬＳＩ
（１６ピン）の素子及びリード線（ワイヤボンディン
グを含む）上に、上述の被覆用酸物の溶液を適下した。Next, 256 bits [)-RAM memory LSI
The above-described coating acid solution was applied onto the (16-pin) element and lead wires (including wire bonding).
その後、１００℃で１時間、２００℃で１時間、２５０
℃で３０分加熱を続け、素子上に３０〜６０μｍの厚さ
の被用膜を得た。After that, 1 hour at 100℃, 1 hour at 200℃, 250℃
Heating was continued for 30 minutes at °C to obtain a coating film with a thickness of 30 to 60 μm on the device.
次いで、ガロカテキンガレートを含む組成物で被覆され
たメモリ用ＬＳＩ素子は、比較例１のエポキシ樹脂組成
物で、トランスファ成形（１８０℃、７０ｋｇ／１ｆｆ
ｌ、１．５分成形）により封止され、樹脂封止型半導体
装置を得た。それぞれ百ヶのＬＳＩについて耐湿信頼性
を評価した。結果を第２表に記した。なお、比較の為に
ガロキンガレートを含まない樹脂組成物を用いたものも
比較例として表２に記載した。Next, the memory LSI element coated with the composition containing gallocatechin gallate was transfer-molded (180°C, 70kg/1ff) using the epoxy resin composition of Comparative Example 1.
1, 1.5 minute molding) to obtain a resin-sealed semiconductor device. Moisture resistance reliability was evaluated for 100 LSIs. The results are shown in Table 2. For comparison, a resin composition containing no galloquine gallate is also listed in Table 2 as a comparative example.
Claims (1)
Ｒ＿４は水素、水酸基またはメトキシル基、Ｒ＿５は水
素、ガロイル基はたはグリコピラシノル基である。〕で
表わされるフラバン−３−オールまたはフラバン−３，
４−ジオールを構成単位とした２−１０量体の群より選
ばれた少なくとも一種のプロアントシアニジンとを含む
ことを特徴とするエポキシ樹脂組成物。[Claims] 1. Polyfunctional epoxy compound and general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 is hydrogen or a hydroxyl group, R_2, R_3,
R_4 is hydrogen, a hydroxyl group or a methoxyl group, and R_5 is hydrogen, a galloyl group or a glycopyracinol group. ] flavan-3-ol or flavan-3,
An epoxy resin composition characterized by containing at least one proanthocyanidin selected from the group of 2-10-mers having 4-diol as a constituent unit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16365486A JPS6320321A (en) | 1986-07-14 | 1986-07-14 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16365486A JPS6320321A (en) | 1986-07-14 | 1986-07-14 | Epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6320321A true JPS6320321A (en) | 1988-01-28 |
Family
ID=15778046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16365486A Pending JPS6320321A (en) | 1986-07-14 | 1986-07-14 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6320321A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994029404A1 (en) * | 1993-06-14 | 1994-12-22 | Berkem | Polyphenol derivative compositions and preparation thereof |
| DE10132936B4 (en) * | 2001-07-06 | 2004-07-15 | Andreas Dr. Hensel | Use of galloylated proanthocyanidin |
-
1986
- 1986-07-14 JP JP16365486A patent/JPS6320321A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994029404A1 (en) * | 1993-06-14 | 1994-12-22 | Berkem | Polyphenol derivative compositions and preparation thereof |
| DE10132936B4 (en) * | 2001-07-06 | 2004-07-15 | Andreas Dr. Hensel | Use of galloylated proanthocyanidin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6320321A (en) | Epoxy resin composition | |
| JP2000109647A (en) | Semiconductor sealing epoxy resin composition and semiconductor device using same | |
| JPS6136854B2 (en) | ||
| JPH07206995A (en) | Epoxy resin composition and sealing material for semiconductor | |
| JP3994511B2 (en) | Epoxy resin composition for semiconductor encapsulation and semiconductor device using the same | |
| JPS6369255A (en) | Semiconductor device | |
| JPH11269349A (en) | Epoxy resin composition for sealing semiconductor and semiconductor device using the composition | |
| JPS62184012A (en) | Heat-resistant resin composition | |
| JPS621609B2 (en) | ||
| JPS62111453A (en) | Semiconductor device | |
| JPS63137919A (en) | Resin composition and semiconductor device sealed therewith | |
| JPS62100520A (en) | Epoxy resin composition | |
| JPH0567704A (en) | Semiconductor device | |
| JPS6351415A (en) | Epoxy resin composition and semiconductor device covered and/or sealed with epoxy composition | |
| JP3975381B2 (en) | Epoxy resin molding material for sealing and electronic component device | |
| JPH11269347A (en) | Epoxy resin composition for sealing semiconductor and semiconductor device using the composition | |
| JPS62171146A (en) | Resin seal type semiconductor device | |
| JPH02123123A (en) | Epoxy resin composition and use thereof | |
| JPH0582675A (en) | Semiconductor device | |
| JPS61269342A (en) | Resin sealed type semiconductor device | |
| JPS5868956A (en) | Resin composition for semiconductor sealing | |
| JPH05259315A (en) | Resin-sealed semiconductor device | |
| JP3539523B2 (en) | Epoxy resin molding material for sealing electronic parts and semiconductor device using the same | |
| JPS62209125A (en) | Epoxy resin composition for sealing semiconductor | |
| JPS6065020A (en) | Resin composition for semiconductor sealing |