CN112771094A - Resin composition for sealing, electronic component device, and method for manufacturing electronic component device - Google Patents
Resin composition for sealing, electronic component device, and method for manufacturing electronic component device Download PDFInfo
- Publication number
- CN112771094A CN112771094A CN201980063108.6A CN201980063108A CN112771094A CN 112771094 A CN112771094 A CN 112771094A CN 201980063108 A CN201980063108 A CN 201980063108A CN 112771094 A CN112771094 A CN 112771094A
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- resin composition
- sealing
- type epoxy
- curing agent
- 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
- 238000007789 sealing Methods 0.000 title claims abstract description 94
- 239000011342 resin composition Substances 0.000 title claims abstract description 87
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title description 17
- 239000003822 epoxy resin Substances 0.000 claims abstract description 133
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 133
- -1 ester compound Chemical class 0.000 claims abstract description 77
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 67
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 48
- 229920003986 novolac Polymers 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 10
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 8
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 6
- 229930003836 cresol Natural products 0.000 claims description 6
- 238000001723 curing Methods 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 24
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 21
- 239000011256 inorganic filler Substances 0.000 description 17
- 229910003475 inorganic filler Inorganic materials 0.000 description 17
- 238000000465 moulding Methods 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 13
- 239000007822 coupling agent Substances 0.000 description 12
- 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 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000003063 flame retardant Substances 0.000 description 10
- 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 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 239000005011 phenolic resin Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000003086 colorant Substances 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 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 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000001721 transfer moulding Methods 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- NADHCXOXVRHBHC-UHFFFAOYSA-N 2,3-dimethoxycyclohexa-2,5-diene-1,4-dione Chemical compound COC1=C(OC)C(=O)C=CC1=O NADHCXOXVRHBHC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 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
- UIXPTCZPFCVOQF-UHFFFAOYSA-N ubiquinone-0 Chemical compound COC1=C(OC)C(=O)C(C)=CC1=O UIXPTCZPFCVOQF-UHFFFAOYSA-N 0.000 description 4
- 229940005561 1,4-benzoquinone Drugs 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical group 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- ZEGDFCCYTFPECB-UHFFFAOYSA-N 2,3-dimethoxy-1,4-benzoquinone Natural products C1=CC=C2C(=O)C(OC)=C(OC)C(=O)C2=C1 ZEGDFCCYTFPECB-UHFFFAOYSA-N 0.000 description 2
- AIACLXROWHONEE-UHFFFAOYSA-N 2,3-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C=CC1=O AIACLXROWHONEE-UHFFFAOYSA-N 0.000 description 2
- SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 description 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical class [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 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
- 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
- 239000011521 glass Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 235000013872 montan acid ester Nutrition 0.000 description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- QJIMTLTYXBDJFC-UHFFFAOYSA-N (4-methylphenyl)-diphenylphosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJIMTLTYXBDJFC-UHFFFAOYSA-N 0.000 description 1
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 1
- FQJZPYXGPYJJIH-UHFFFAOYSA-N 1-bromonaphthalen-2-ol Chemical compound C1=CC=CC2=C(Br)C(O)=CC=C21 FQJZPYXGPYJJIH-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- BLBVJHVRECUXKP-UHFFFAOYSA-N 2,3-dimethoxy-1,4-dimethylbenzene Chemical group COC1=C(C)C=CC(C)=C1OC BLBVJHVRECUXKP-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
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-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
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- FXTKWBZFNQHAAO-UHFFFAOYSA-N 3-iodophenol Chemical compound OC1=CC=CC(I)=C1 FXTKWBZFNQHAAO-UHFFFAOYSA-N 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 description 1
- SSQQUEKFNSJLKX-UHFFFAOYSA-N 4-bromo-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(Br)=CC(C(C)(C)C)=C1O SSQQUEKFNSJLKX-UHFFFAOYSA-N 0.000 description 1
- IWJGMJHAIUBWKT-UHFFFAOYSA-N 4-bromo-2-methylphenol Chemical compound CC1=CC(Br)=CC=C1O IWJGMJHAIUBWKT-UHFFFAOYSA-N 0.000 description 1
- WMUWDPLTTLJNPE-UHFFFAOYSA-N 4-bromo-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Br WMUWDPLTTLJNPE-UHFFFAOYSA-N 0.000 description 1
- GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- LVSPDZAGCBEQAV-UHFFFAOYSA-N 4-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(Cl)C2=C1 LVSPDZAGCBEQAV-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000004206 montan acid ester Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- CGEXUOTXYSGBLV-UHFFFAOYSA-N phenyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OC1=CC=CC=C1 CGEXUOTXYSGBLV-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- PSEQWFPWQRZBOO-UHFFFAOYSA-M tetrahexylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC PSEQWFPWQRZBOO-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 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
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
-
- 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
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
A resin composition for sealing, which contains an epoxy resin comprising a polyfunctional epoxy resin and a difunctional epoxy resin and a curing agent comprising a reactive ester compound.
Description
Technical Field
The invention relates to a sealing resin composition, an electronic component device and a method for manufacturing the electronic component device.
Background
The amount of transmission loss generated by thermal conversion of a radio wave transmitted for communication in a dielectric medium is expressed as the product of the frequency and the square root of the relative dielectric constant and the dielectric loss tangent. In other words, since a transmission signal is easily converted into heat in proportion to the frequency, the higher the frequency band is, the lower the dielectric characteristics are required for the material of the communication member in order to suppress the transmission loss.
For example, patent documents 1 to 2 disclose thermosetting resin compositions containing an active ester resin as a curing agent for an epoxy resin, which can suppress the dielectric loss tangent of a cured product to be low.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2012 and 246367
Patent document 2: japanese patent laid-open No. 2014-114352
Disclosure of Invention
Problems to be solved by the invention
As a curing agent for an epoxy resin, an active ester compound is advantageous in that the dielectric properties of a cured product are suppressed to be lower than those of a phenol curing agent or an amine curing agent. However, a sealing resin composition containing an active ester compound as a curing agent for an epoxy resin tends to have poor moldability.
The embodiments of the present disclosure are completed based on the above-described situation.
The disclosed subject matter is to provide a sealing resin composition that achieves both flowability and curability during molding and that has a cured product with a low dielectric loss tangent, an electronic component device sealed using the sealing resin composition, and a method for manufacturing an electronic component device sealed using the sealing resin composition.
Means for solving the problems
Specific means for solving the above problems include the following means.
[1] A resin composition for sealing, which contains an epoxy resin comprising a polyfunctional epoxy resin and a difunctional epoxy resin and a curing agent comprising a reactive ester compound.
[2] The resin composition for sealing according to [1], wherein the polyfunctional epoxy resin contains at least 1 selected from the group consisting of a triphenylmethane type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a naphthalene diol aralkyl type epoxy resin, a naphthol aralkyl type epoxy resin and a dicyclopentadiene type epoxy resin.
[3] The resin composition for sealing according to [1] or [2], wherein the bifunctional epoxy resin comprises at least 1 selected from the group consisting of a bisphenol F type epoxy resin, a bisphenol A type epoxy resin, a biphenyl aralkyl type epoxy resin and a naphthalene type epoxy resin.
[4] The sealing resin composition according to any one of [1] to [3], wherein the mass ratio of the polyfunctional epoxy resin to the total amount of the polyfunctional epoxy resin and the difunctional epoxy resin is 50 to 95 mass%.
[5] An electronic component device, comprising: a support member; an element disposed on the support member; and the sealing resin composition according to any one of [1] to [4] for sealing the element.
[6] A method of manufacturing an electronic component device, comprising: disposing the element on the support member; and a step of sealing the element with the sealing resin composition according to any one of [1] to [4 ].
ADVANTAGEOUS EFFECTS OF INVENTION
The present disclosure provides a sealing resin composition which achieves both flowability and curability at the time of molding and in which the dielectric loss tangent of a cured product is low, an electronic component device sealed using the sealing resin composition, and a method for manufacturing an electronic component device sealed using the sealing resin composition.
Detailed Description
In the present disclosure, the term "step" includes a step that is independent from other steps, and also includes a step that is not clearly distinguished from other steps, as long as the purpose of the step is achieved.
In the present disclosure, a numerical range represented by "to" includes numerical values before and after "to" as a minimum value and a maximum value, respectively.
In the numerical ranges recited in the present disclosure, the upper limit or the lower limit recited in one numerical range may be replaced with the upper limit or the lower limit recited in another numerical range recited in a stepwise manner. In the numerical ranges disclosed in the present disclosure, the upper limit or the lower limit of the numerical range may be replaced with the values shown in the examples.
In the present disclosure, each ingredient may contain a plurality of the same substances. When a plurality of substances corresponding to each component are present in the composition, the content or content of each component refers to the total content or content of the plurality of substances present in the composition unless otherwise specified.
In the present disclosure, the particles corresponding to each ingredient may be contained in plural kinds. When a plurality of particles corresponding to each component are present in the composition, the particle diameter of each component is a value for a mixture of the plurality of particles present in the composition unless otherwise specified.
< sealing resin composition >
The sealing resin composition of the present disclosure contains an epoxy resin including a polyfunctional epoxy resin and a difunctional epoxy resin, and a curing agent including an active ester compound.
The active ester compound in the present disclosure means a compound having 1 or more ester groups reactive with an epoxy group in 1 molecule and having a curing action of an epoxy resin.
Conventionally, as a curing agent for an epoxy resin, a phenol curing agent, an amine curing agent, and the like have been generally used, but secondary hydroxyl groups are generated in the reaction of an epoxy resin with a phenol curing agent or an amine curing agent. In contrast, in the reaction of the epoxy resin and the active ester compound, an ester group is generated instead of the secondary hydroxyl group. Since the ester group is less polar than the secondary hydroxyl group, the sealing resin composition of the present disclosure can suppress the dielectric loss tangent of a cured product to be lower than a sealing resin composition containing only a curing agent that generates a secondary hydroxyl group as a curing agent.
However, a sealing resin composition containing an active ester compound as a curing agent for an epoxy resin tends to have poor moldability. The reason for this is presumed to be: since the reactivity of the active ester compound with the epoxy resin is lower than that of the phenol curing agent or the amine curing agent with the epoxy resin, the crosslinking density and the glass transition temperature after heat curing are low, and the curability at the time of molding is poor. In addition, it is presumed that: the sealing resin composition containing an active ester compound as a curing agent for an epoxy resin tends to have a lower flowability than a sealing resin composition containing another curing agent (for example, a phenol curing agent), which also has an influence.
In contrast, we speculate that: the sealing resin composition of the present disclosure can increase the crosslinking density and glass transition temperature after heat curing by using an active ester compound as a curing agent and including a polyfunctional epoxy resin, and thus has excellent curability during molding. In addition, the sealing resin composition of the present disclosure ensures fluidity during molding by using a difunctional epoxy resin in combination with a multifunctional epoxy resin.
Therefore, the sealing resin composition of the present disclosure can achieve both flowability and curability during molding, and as a result, has excellent moldability.
Here, the curability of the sealing resin composition of the present disclosure at the time of molding is a performance evaluated from hot hardness immediately after molding.
(epoxy resin)
The epoxy resin is not particularly limited in its kind as long as it has an epoxy group in its molecule. The polyfunctional epoxy resin is not particularly limited in kind as long as it has 3 or more epoxy groups in the molecule. The type of the bifunctional epoxy resin is not particularly limited as long as it is a resin having 2 epoxy groups in the molecule.
The number of epoxy groups in the polyfunctional epoxy resin is preferably 3 to 8, and more preferably 3 to 5.
Examples of the polyfunctional epoxy resin include: triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, phenol novolac type epoxy resin, dihydroxybenzene novolac type epoxy resin, cresol novolac type epoxy resin, glycidylamine type epoxy resin, naphthalene skeleton type epoxy resin, naphthalenediol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, and the like, and derivatives thereof. These polyfunctional epoxy resins may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The polyfunctional epoxy resin preferably contains at least 1 selected from the group consisting of a triphenylmethane type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a naphthalenediol aralkyl type epoxy resin, a naphthol aralkyl type epoxy resin and a dicyclopentadiene type epoxy resin from the viewpoint of crosslinking density.
The triphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by using a compound having a triphenylmethane skeleton as a raw material, and an epoxy resin obtained by glycidyletherifying a triphenylmethane type phenol resin is preferable.
Examples of the difunctional epoxy resin include: bisphenol F-type epoxy resins, bisphenol a-type epoxy resins, bisphenol S-type epoxy resins, bisphenol a novolac-type epoxy resins, biphenyl aralkyl-type epoxy resins, naphthalene-type epoxy resins, and the like, and derivatives thereof. These bifunctional epoxy resins may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The bifunctional epoxy resin preferably contains at least 1 selected from the group consisting of a bisphenol F type epoxy resin, a bisphenol a type epoxy resin, a biphenyl aralkyl type epoxy resin, and a naphthalene type epoxy resin from the viewpoint of fluidity. Among them, biphenyl type epoxy resins are more preferable from the viewpoint of fluidity.
Monofunctional epoxy resins may also be used together with multifunctional epoxy resins and difunctional epoxy resins. The monofunctional epoxy resin may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
From the viewpoint of satisfying both flowability and curability at the time of molding, the polyfunctional epoxy resin is preferably 50 to 95% by mass, more preferably 60 to 93% by mass, and still more preferably 70 to 90% by mass, based on the total mass of the epoxy resin.
From the viewpoint of satisfying both flowability and curability at the time of molding, the mass ratio of the polyfunctional epoxy resin in the total amount of the polyfunctional epoxy resin and the difunctional epoxy resin is preferably 50 to 95 mass%, more preferably 60 to 93 mass%, and still more preferably 70 to 90 mass%.
The epoxy equivalent (molecular weight/number of epoxy groups) of the epoxy resin is not particularly limited. From the viewpoint of a balance among various properties such as moldability, reflow resistance and electrical reliability, it is preferably from 80 to 500g/eq, more preferably from 90 to 200 g/eq.
The epoxy equivalent of the epoxy resin is set to a value determined by the method according to JISK 7236: 2009.
In the case where the epoxy resin is a solid, the softening point or melting point thereof is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably from 40 ℃ to 180 ℃, and more preferably from 50 ℃ to 130 ℃ from the viewpoint of handling properties in the production of the sealing resin composition.
The melting point of the epoxy resin is a value measured by Differential Scanning Calorimetry (DSC), and the softening point of the epoxy resin is a value measured by a Differential Scanning Calorimetry (DSC) method according to JIS K7234: 1986 (Ring and ball method).
The content of the epoxy resin in the sealing resin composition is preferably 0.5 to 50% by mass, and more preferably 2 to 30% by mass, from the viewpoints of strength, fluidity, heat resistance, moldability, and the like.
(curing agent)
The sealing resin composition of the present disclosure contains at least an active ester compound as a curing agent. The sealing resin composition of the present disclosure may contain a curing agent other than the active ester compound.
As described above, the sealing resin composition of the present disclosure can suppress the dielectric loss tangent of a cured product to be low by using an active ester compound as a curing agent.
In addition, the polar group in the cured product improves the water absorption of the cured product, and the active ester compound is used as the curing agent, so that the concentration of the polar group in the cured product can be suppressed, and the water absorption of the cured product can be suppressed. And, by suppressing the water absorption of the cured product, that is, by suppressing H as a polar molecule2The content of O can suppress the dielectric loss tangent of the cured product to a lower level. The water absorption of the cured product is preferably 0% to 0.35%, more preferably 0% to 0.30%, and still more preferably 0% to 0.28%. The water absorption of the cured product was the mass increase rate determined by the pressure cooker boiling test (121 ℃, 2.1 atm, 24 hours).
The kind of the active ester compound is not particularly limited as long as it has 1 or more ester groups reactive with epoxy groups in the molecule.
Examples of the active ester compound include: phenol ester compounds, thiophenol ester compounds, N-hydroxylamine ester compounds, esters of heterocyclic hydroxyl compounds, and the like.
Examples of the active ester compound include: an ester compound obtained from at least 1 of an aliphatic carboxylic acid and an aromatic carboxylic acid and at least 1 of an aliphatic hydroxy compound and an aromatic hydroxy compound. An ester compound containing an aliphatic compound as a component for polycondensation tends to have excellent compatibility with an epoxy resin because it has an aliphatic chain. Ester compounds containing an aromatic compound as a component for polycondensation tend to have excellent heat resistance because they have an aromatic ring.
Specific examples of the active ester compound include aromatic esters obtained by a condensation reaction of an aromatic carboxylic acid and a phenolic hydroxyl group. Among them, preferred are: an aromatic ester obtained by a condensation reaction of an aromatic carboxylic acid, wherein 2 to 4 hydrogen atoms of an aromatic ring are substituted with carboxyl groups, such as benzene, naphthalene, biphenyl, diphenylpropane, diphenylmethane, diphenyl ether, or diphenylsulfonic acid, and a phenolic hydroxyl group, is used as a starting material, and a mixture of an aromatic carboxylic acid component, wherein 1 hydrogen atom of the aromatic ring is substituted with a hydroxyl group, a monohydric phenol, wherein 2 to 4 hydrogen atoms of the aromatic ring are substituted with a hydroxyl group, and a polyhydric phenol, wherein 2 to 4 hydrogen atoms of the aromatic ring are substituted with a hydroxyl group, is used. That is, the aromatic ester preferably has a structural unit derived from the aromatic carboxylic acid component, a structural unit derived from the monohydric phenol, and a structural unit derived from the polyhydric phenol.
Specific examples of the active ester compound include: an active ester resin having a structure obtained by reacting a phenol resin having a molecular structure formed by bonding (Japanese) phenol compounds via an aliphatic cyclic hydrocarbon group, an aromatic dicarboxylic acid or a halide thereof, and an aromatic monohydroxy compound, as described in Japanese patent laid-open No. 2012-246367. As the active ester resin, a compound represented by the following structural formula (1) is preferable.
[ chemical formula 1]
In the structural formula (1), R1The alkyl group has 1 to 4 carbon atoms, X is a benzene ring, a naphthalene ring, a benzene ring or a naphthalene ring substituted by an alkyl group having 1 to 4 carbon atoms, or a biphenyl group, Y is a benzene ring, a naphthalene ring, or a benzene ring or a naphthalene ring substituted by an alkyl group having 1 to 4 carbon atoms, k is 0 or 1, n represents the average of the number of repetitions and is 0.25 to 1.5.
Specific examples of the compound represented by the structural formula (1) include the following exemplified compounds (1-1) to (1-10). t-Bu in the structural formula is tert-butyl.
[ chemical formula 2]
[ chemical formula 3]
Another specific example of the active ester compound includes a compound represented by the following structural formula (2) and a compound represented by the following structural formula (3) described in japanese patent application laid-open No. 2014-114352.
[ chemical formula 4]
In the structural formula (2), R1And R2Each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, Z represents an ester-forming structural site (Z1) or a hydrogen atom (Z2) selected from the group consisting of a benzoyl group, a naphthoyl group, a benzoyl group or naphthoyl group substituted with an alkyl group having 1 to 4 carbon atoms, and an acyl group having 2 to 6 carbon atoms, and at least 1 of Z represents an ester-forming structural site (Z1).
In the structural formula (3), R1And R2Each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, Z represents an ester-forming structural site (Z1) or a hydrogen atom (Z2) selected from the group consisting of a benzoyl group, a naphthoyl group, a benzoyl group or naphthoyl group substituted with an alkyl group having 1 to 4 carbon atoms, and an acyl group having 2 to 6 carbon atoms, and at least 1 of Z represents an ester-forming structural site (Z1).
Specific examples of the compound represented by the structural formula (2) include the following exemplified compounds (2-1) to (2-6).
[ chemical formula 5]
Specific examples of the compound represented by the structural formula (3) include the following exemplified compounds (3-1) to (3-6).
[ chemical formula 6]
As the active ester compound, commercially available products can be used. As the commercially available active ester compounds, examples of the active ester compounds having a dicyclopentadiene type diphenol structure include "EXB 9451", "EXB 9460S" and "HPC-8000-65T" (available from DIC); examples of the active ester compound having an aromatic structure include "EXB 9416-70 BK", "EXB-8" and "EXB-9425" (available from DIC); examples of the active ester compound containing an acetylate of phenol novolac include "DC 808" (manufactured by Mitsubishi Chemical corporation); examples of the active ester compound including a benzoyl compound of phenol novolac include "YLH 1026" (manufactured by Mitsubishi Chemical corporation).
The active ester compounds can be used alone in 1 kind, also can be combined with more than 2 kinds.
The ester group equivalent of the active ester compound is not particularly limited. From the viewpoint of a balance among various characteristics such as moldability, reflow resistance, and electrical reliability, it is preferably from 150 to 400g/eq, more preferably from 170 to 300g/eq, and still more preferably from 200 to 250 g/eq.
The ester group equivalent of the active ester compound is defined by the following formula in accordance with JIS K0070: 1992.
From the viewpoint of suppressing the dielectric loss tangent of the cured product to be low, the equivalent ratio (ester group/epoxy group) of the epoxy resin to the active ester compound is preferably 0.9 or more, more preferably 0.95 or more, and still more preferably 0.97 or more.
From the viewpoint of suppressing the unreacted components of the active ester compound to a small amount, the equivalent ratio (ester group/epoxy group) of the epoxy resin to the active ester compound is preferably 1.1 or less, more preferably 1.05 or less, and still more preferably 1.03 or less.
The curing agent may contain other curing agents than the active ester compound. In this case, the kind of the other curing agent is not particularly limited, and may be selected according to the desired characteristics of the sealing resin composition. Examples of the other curing agent include a phenol curing agent, an amine curing agent, an acid anhydride curing agent, a polythiol curing agent, a polyaminoamide curing agent, an isocyanate curing agent, a blocked isocyanate curing agent, and the like.
Specific examples of the phenol curing agent include: polyhydric phenol compounds such as resorcinol, catechol, bisphenol a, bisphenol F, and substituted or unsubstituted diphenols; phenol novolac resins obtained by condensing or co-condensing aldehyde compounds such as formaldehyde, acetaldehyde and propionaldehyde with an acidic catalyst, wherein the phenolic compounds are at least one selected from phenol compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol a, bisphenol F, phenylphenol and aminophenol, and naphthol compounds such as α -naphthol, β -naphthol and dihydroxynaphthalene; aralkyl phenol resins such as phenol aralkyl resins and naphthol aralkyl resins synthesized from the above phenolic compounds and dimethoxyp-xylene, bis (methoxymethyl) biphenyl and the like; p-xylene modified phenolic resin and m-xylene modified phenolic resin; melamine modified phenolic resin; terpene-modified phenolic resin; dicyclopentadiene type phenol resins and dicyclopentadiene type naphthol resins synthesized by copolymerization of the above-mentioned phenolic compounds with dicyclopentadiene; cyclopentadiene-modified phenol resin; polycyclic aromatic ring-modified phenol resins; biphenyl type phenol resin; a triphenylmethane-type phenol resin obtained by condensing or co-condensing the above phenolic compound with an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde under an acidic catalyst; a phenol resin obtained by copolymerizing two or more of these; and the like. These phenol curing agents may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The functional group equivalent (hydroxyl group equivalent in the case of a phenol curing agent) of the other curing agent is not particularly limited. From the viewpoint of a balance among various properties such as moldability, reflow resistance, and electrical reliability, it is preferably from 70g/eq to 1000g/eq, and more preferably from 80g/eq to 500 g/eq.
The functional group equivalent (hydroxyl group equivalent in the case of a phenol curing agent) of the other curing agent was determined by the following equation in accordance with JIS K0070: 1992.
In the case where the curing agent is a solid, the softening point or melting point thereof is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably from 40 ℃ to 180 ℃, and more preferably from 50 ℃ to 130 ℃ from the viewpoint of handling properties in the production of the resin composition for sealing.
The melting point or softening point of the curing agent is measured in the same manner as the melting point or softening point of the epoxy resin.
The equivalent ratio of the epoxy resin to the entire curing agent (active ester compound and other curing agent), that is, the ratio of the number of functional groups in the curing agent to the number of functional groups in the epoxy resin (number of functional groups in the curing agent/number of functional groups in the epoxy resin) is not particularly limited. From the viewpoint of suppressing the amount of unreacted components to a small amount, the amount is preferably set to a range of 0.5 to 2.0, and more preferably 0.6 to 1.3. From the viewpoint of moldability and reflow resistance, the range of 0.8 to 1.2 is more preferable.
From the viewpoint of suppressing the dielectric loss tangent of the cured product to be low, the content of the active ester compound with respect to the total mass of the active ester compound and the other curing agent is preferably 80 mass% or more, more preferably 85 mass% or more, and still more preferably 90 mass% or more.
From the viewpoint of suppressing the dielectric loss tangent of the cured product to be low, the content of the total of the epoxy resin and the active ester compound relative to the total mass of the epoxy resin, the active ester compound and the other curing agent is preferably 70 mass% or more, more preferably 80 mass% or more, and still more preferably 85 mass% or more.
(curing accelerators)
The sealing resin composition may contain a curing accelerator. The type of the curing accelerator is not particularly limited, and may be selected according to the type of the epoxy resin or the curing agent, the desired properties of the sealing resin composition, and the like.
Examples of the curing accelerator include: diazabicycloalkenes such as 1, 5-diazabicyclo [4.3.0] nonene-5 (DBN) and 1, 8-diazabicyclo [5.4.0] undecene-7 (DBU), and cyclic amidine compounds such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole and 2-heptadecylimidazole; derivatives of the above cyclic amidine compounds; phenol novolac salts of the above cyclic amidine compounds or derivatives thereof; compounds having intramolecular polarization obtained by adding a quinone compound such as maleic anhydride, 1, 4-benzoquinone, 2, 5-toluquinone, 1, 4-naphthoquinone, 2, 3-dimethylbenzoquinone, 2, 6-dimethylbenzoquinone, 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone, 2, 3-dimethoxy-1, 4-benzoquinone, phenyl-1, 4-benzoquinone, or a compound having a pi bond such as diazophenylmethane to these compounds; cyclic amidine (アミジニウム) compounds such as tetraphenylborate of DBU, tetraphenylborate of DBN, tetraphenylborate of 2-ethyl-4-methylimidazole and tetraphenylborate of N-methylmorpholine, and isocyanate-added compounds; isocyanate adducts of DBU, isocyanate adducts of DBN, isocyanate adducts of 2-ethyl-4-methylimidazole, and isocyanate adducts of N-methylmorpholine; tertiary amine compounds such as pyridine, triethylamine, triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, and tris (dimethylaminomethyl) phenol; derivatives of the above tertiary amine compounds; ammonium salt compounds such as tetra-n-butylammonium acetate, tetra-n-butylammonium phosphate, tetraethylammonium acetate, tetra-n-hexylammonium benzoate, tetrapropylammonium hydroxide and the like; tertiary phosphines such as triphenylphosphine, diphenyl (p-tolyl) phosphine, tri (alkylphenyl) phosphine, tri (alkoxyphenyl) phosphine, tri (alkyl-alkoxyphenyl) phosphine, tri (dialkylphenyl) phosphine, tri (trialkylphenyl) phosphine, tri (tetraalkylphenyl) phosphine, tri (dialkoxyphenyl) phosphine, tri (trialkoxyphenyl) phosphine, tri (tetraalkoxyphenyl) phosphine, trialkylphosphine, dialkylarylphosphine, and alkyldiarylphosphine; phosphine compounds such as complexes of the above tertiary phosphines with organic boron compounds; a compound having intramolecular polarization obtained by adding the tertiary phosphine or the phosphine compound to a compound having a pi bond such as maleic anhydride, 1, 4-benzoquinone, 2, 5-toluquinone, 1, 4-naphthoquinone, 2, 3-dimethylbenzoquinone, 2, 6-dimethylbenzoquinone, 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone, 2, 3-dimethoxy-1, 4-benzoquinone, phenyl-1, 4-benzoquinone, or the like, or diazophenylmethane; a halogenated phenol compound such as 4-bromophenol, 3-bromophenol, 2-bromophenol, 4-chlorophenol, 3-chlorophenol, 2-chlorophenol, 4-iodophenol, 3-iodophenol, 2-iodophenol, 4-bromo-2-methylphenol, 4-bromo-3-methylphenol, 4-bromo-2, 6-dimethylphenol, 4-bromo-3, 5-dimethylphenol, 4-bromo-2, 6-di-tert-butylphenol, 4-chloro-1-naphthol, 1-bromo-2-naphthol, 6-bromo-2-naphthol, 4-bromo-4' -hydroxybiphenyl, etc., followed by a dehydrohalogenation step, A compound having intramolecular polarization; tetra-substituted phosphonium such as tetraphenylphosphonium, tetra-p-tolylborate, etc. which are free from phenyl groups bonded to boron atoms; salts of tetraphenylphosphonium with phenolic compounds; salts of partial hydrolyzates of tetraalkylphosphonium and aromatic carboxylic acid anhydrides, and the like.
When the sealing resin composition contains a curing accelerator, the amount thereof is preferably 0.1 to 30 parts by mass, and more preferably 1 to 15 parts by mass, per 100 parts by mass of the resin component (the total amount of the epoxy resin and the curing agent). If the amount of the curing accelerator is 0.1 part by mass or more per 100 parts by mass of the resin component, the curing tends to be good in a short time. If the amount of the curing accelerator is 30 parts by mass or less per 100 parts by mass of the resin component, the curing rate tends not to be too high, and a good molded article tends to be obtained.
(inorganic Filler)
The sealing resin composition may contain an inorganic filler. The kind of the inorganic filler is not particularly limited. Specific examples thereof include inorganic materials such as fused silica, crystalline silica, glass, alumina, talc, clay, and mica. Inorganic filler materials having a flame retardant effect may also be used. Examples of the inorganic filler having a flame retardant effect include aluminum hydroxide, magnesium hydroxide, composite metal hydroxides such as composite hydroxide of magnesium and zinc, zinc borate, and the like.
Among the inorganic fillers, silica such as fused silica is preferable from the viewpoint of reducing the linear expansion coefficient, and alumina is preferable from the viewpoint of high thermal conductivity. The inorganic filler may be used alone in 1 kind, or may be used in combination in 2 or more kinds. Examples of the form of the inorganic filler include powder, beads obtained by spheroidizing the powder, and fibers.
When the inorganic filler is in the form of particles, the average particle diameter thereof is not particularly limited. For example, the average particle diameter is preferably 0.2 to 100. mu.m, more preferably 0.5 to 50 μm. When the average particle diameter is 0.2 μm or more, the viscosity of the sealing resin composition tends to be further suppressed from increasing. When the average particle diameter is 100 μm or less, the filling property tends to be further improved. The average particle size of the inorganic filler was determined as a volume average particle size (D50) by a laser scattering diffraction particle size distribution measuring apparatus.
The content of the inorganic filler contained in the sealing resin composition is not particularly limited. From the viewpoint of fluidity and strength, the volume of the entire sealing resin composition is preferably 30 to 90 vol%, more preferably 35 to 80 vol%, and still more preferably 40 to 70 vol%. If the content of the inorganic filler is 30 vol% or more of the entire sealing resin composition, the properties such as the thermal expansion coefficient, thermal conductivity, and elastic modulus of the cured product tend to be further improved. If the content of the inorganic filler is 90 vol% or less of the entire sealing resin composition, the increase in viscosity of the sealing resin composition is suppressed, the fluidity is further improved, and the moldability tends to be further improved.
[ various additives ]
The sealing resin composition may contain various additives such as a coupling agent, an ion exchanger, a release agent, a flame retardant, and a colorant, which are exemplified below, in addition to the above components. The sealing resin composition may contain, in addition to the additives exemplified below, various additives known in the art as needed.
(coupling agent)
The sealing resin composition may contain a coupling agent. The sealing resin composition preferably contains a coupling agent from the viewpoint of improving the adhesiveness between the resin component and the inorganic filler. Examples of the coupling agent include: known coupling agents such as silane-based compounds such as epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, vinyl silane, and disilazane, titanium-based compounds, aluminum chelate compounds, and aluminum/zirconium-based compounds.
When the sealing resin composition contains a coupling agent, the amount of the coupling agent is preferably 0.05 to 5 parts by mass, and more preferably 0.1 to 2.5 parts by mass, per 100 parts by mass of the inorganic filler. If the amount of the coupling agent is 0.05 parts by mass or more per 100 parts by mass of the inorganic filler, the adhesion to the frame tends to be further improved. If the amount of the coupling agent is 5 parts by mass or less based on 100 parts by mass of the inorganic filler, the moldability of the package tends to be further improved.
(ion exchanger)
The sealing resin composition may contain an ion exchanger. The sealing resin composition preferably contains an ion exchanger from the viewpoint of improving moisture resistance and high-temperature storage characteristics of an electronic component device provided with an element to be sealed. The ion exchanger is not particularly limited, and conventionally known ion exchangers can be used. Specifically, there may be mentioned hydrotalcite compounds, and hydrous oxides of at least 1 element selected from magnesium, aluminum, titanium, zirconium and bismuth. The ion exchanger may be used alone in 1 kind, or may be used in combination of 2 or more kinds. Among them, hydrotalcite represented by the following general formula (a) is preferable.
Mg(1-X)AlX(OH)2(CO3)X/2·mH2O……(A)
(0< X < 0.5, m is positive number)
When the sealing resin composition contains an ion exchanger, the content thereof is not particularly limited as long as it is a sufficient amount for capturing halogen ions or the like. For example, the amount is preferably 0.1 to 30 parts by mass, more preferably 1 to 10 parts by mass, per 100 parts by mass of the resin component (total amount of the epoxy resin curing agent).
(mold releasing agent)
The sealing resin composition may contain a release agent from the viewpoint of obtaining good releasability from a mold at the time of molding. The release agent is not particularly limited, and a conventionally known release agent can be used. Specifically, examples thereof include higher fatty acids such as carnauba wax, montanic acid, stearic acid, etc., higher fatty acid metal salts, ester-based waxes such as montanic acid esters, etc., and polyolefin-based waxes such as oxidized polyethylene, non-oxidized polyethylene, etc. The release agent may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
When the sealing resin composition contains a release agent, the amount thereof is preferably 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the resin component (the total amount of the epoxy resin and the curing agent). When the amount of the release agent is 0.01 parts by mass or more per 100 parts by mass of the resin component, the releasability tends to be sufficiently obtained. When the amount is 10 parts by mass or less, more excellent adhesiveness tends to be obtained.
(flame retardant)
The sealing resin composition may contain a flame retardant. The flame retardant is not particularly limited, and conventionally known flame retardants can be used. Specifically, there may be mentioned: organic or inorganic compounds containing a halogen atom, an antimony atom, a nitrogen atom or a phosphorus atom, metal hydroxides, and the like. The flame retardant may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
When the sealing resin composition contains a flame retardant, the amount thereof is not particularly limited as long as it is an amount sufficient to obtain a desired flame retardant effect. For example, the amount is preferably 1 to 30 parts by mass, and more preferably 2 to 20 parts by mass, per 100 parts by mass of the resin component (the total amount of the epoxy resin and the curing agent).
(coloring agent)
The sealing resin composition may contain a colorant. Examples of the colorant include known colorants such as carbon black, organic dyes, organic pigments, titanium oxide, red lead, and red iron oxide. The content of the colorant may be appropriately selected depending on the purpose and the like. The colorant may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
(method for producing sealing resin composition)
The method for producing the sealing resin composition is not particularly limited. Typical methods include: a method in which components are sufficiently mixed in a predetermined mixing amount by a mixer or the like, and then melt-kneaded by a grinding roll, an extruder or the like, cooled, and pulverized. More specifically, examples thereof include: a method of uniformly stirring and mixing predetermined amounts of the above components, kneading, cooling, and pulverizing the mixture by a kneader, a roll, an extruder, or the like heated to 70 to 140 ℃.
The sealing resin composition is preferably solid at normal temperature and normal pressure (e.g., 25 ℃ C., atmospheric pressure). The shape of the sealing resin composition in the case of being a solid is not particularly limited, and examples thereof include powder, granule, and sheet. From the viewpoint of handling properties, the size and mass of the sealing resin composition in the form of a sheet are preferably such that they meet the molding conditions of the package.
< electronic component device >
An electronic component device according to an embodiment of the present disclosure includes a support member, an element disposed on the support member, and a cured product of the sealing resin composition of the present disclosure sealing the element.
Examples of the electronic component device include: a device obtained by sealing an element portion obtained by mounting an element (active element such as a semiconductor chip, a transistor, a diode, or a thyristor, or a passive element such as a capacitor, a resistor, or a coil) on a support member such as a lead frame, a wired tape carrier, a wiring board, glass, a silicon wafer, or an organic substrate with a sealing resin composition.
More specifically, there may be mentioned: a typical resin-sealed IC such as DIP (Dual Inline Package), PLCC (Plastic Leaded Chip Carrier with leads), QFP (Quad Flat Package), SOP (Small Outline Package), SOJ (Small Outline J-lead Package), TSOP (Thin Small Outline Package), TQFP (Thin Quad Flat Package), and TQFP (Thin Quad Flat Package) has a structure in which an element is fixed to a lead frame, and a terminal portion of an element such as a bonding pad and the like is connected to a lead portion by wire bonding, a bump, and the like, and then sealed by transfer molding or the like using a sealing resin composition; a TCP (Tape Carrier Package) having a structure in which a device connected to a Tape Carrier by bumps is sealed with a sealing resin composition; a COB (Chip On Board) module, a hybrid IC, a multi-Chip module, and the like, which have a structure in which an element connected to a wiring formed On a support member by wire bonding, flip Chip bonding, solder, or the like is sealed with a sealing resin composition; BGA (Ball Grid Array), CSP (Chip Size Package), and MCP (Multi Chip Package) having a structure in which a device is mounted on the surface of a support member having terminals for connecting a wiring board formed on the back surface thereof, the device is connected to a wiring formed on the support member by bump or wire bonding, and then the device is sealed with a sealing resin composition; and the like. In addition, the sealing resin composition can be suitably used for a printed wiring board.
< method for producing electronic component device >
The method for manufacturing the electronic component device of the present disclosure includes: a step of disposing the element on the support member, and a step of sealing the element with the sealing resin composition of the present disclosure.
The method for carrying out each step is not particularly limited, and can be carried out by a usual method. In addition, the kind of the supporting member and the element used in the manufacture of the electronic component device is not particularly limited, and a supporting member and an element generally used in the manufacture of the electronic component device may be used.
Examples of a method for sealing an element using the sealing resin composition of the present disclosure include a low-pressure transfer molding method, an injection molding method, a compression molding method, and the like. Among them, low-pressure transfer molding is common.
Examples
The above embodiments will be specifically described below by way of examples, but the scope of the above embodiments is not limited to these examples.
< preparation of sealing resin composition >
The components shown below were mixed in the mixing ratios shown in table 1 to prepare sealing resin compositions of examples and comparative examples. The sealing resin composition is solid at normal temperature and pressure.
Epoxy resin 1 (multifunctional): triphenylmethane type epoxy resin having an epoxy equivalent of 167g/eq (Mitsubishi Chemical Co., Ltd., trade name "1032H 60")
Epoxy resin 2 (multifunctional): cresol novolac epoxy resin having an epoxy equivalent of 264g/eq (DIC corporation, trade name "HP-5600")
Epoxy resin 3 (multifunctional): naphthol aralkyl type epoxy resin, epoxy equivalent 170g/eq (New Nippon iron King chemical Co., Ltd., trade name "ESN-375")
Epoxy resin 4 (difunctional): biphenyl type epoxy resin having an epoxy equivalent of 192g/eq (Mitsubishi Chemical Co., Ltd., trade name "YX-4000")
Active ester compound 1: DIC corporation, trade name "EXB-8"
Active ester compound 2: DIC corporation, trade name "EXB-9425"
Phenol curing agent 1: phenol aralkyl resin, hydroxyl equivalent 175g/eq (product name "MEH 7800 SS" manufactured by Minghuaji Co., Ltd.)
Curing accelerator 1: triphenylphosphine/1, 4-benzoquinone adduct
Curing accelerator 2: imidazole Compound (product name "CURIZOL 2 MA-OK" available from Situo Kasei Co., Ltd.)
Filler 1: fused silica (DENKA, trade name "FB 9454 FC", volume average particle diameter 10 μm)
Coupling agent 1: n-phenyl-3-aminopropyltrimethoxysilane (trade name "KBM-573" available from shin Etsu chemical Co., Ltd.)
Coupling agent 2: 3-mercaptopropyltrimethoxysilane (trade name "KBM-803" of shin-Etsu chemical Co., Ltd.)
Mold release agent: montanic acid ester wax (Clariant Japan K.K., trade name "HW-E")
The colorant: carbon Black (Mitsubishi Chemical Co., Ltd., trade name "MA 600")
< evaluation of Properties of sealing resin composition >
(spiral flow)
The resin composition for sealing was molded at a mold temperature of 180 ℃ under a molding pressure of 6.9MPa for a curing time of 90 seconds using a mold for spiral flow measurement according to EMMI-1-66 to determine a flow distance (cm).
(hardness when heated)
The sealing resin composition was charged into a transfer molding machine and molded under conditions of a mold temperature of 180 ℃, a molding pressure of 6.9MPa, and a curing time of 90 seconds to obtain a disk-shaped molded article (diameter 40mm, thickness 5 mm). The molded article was used as a test piece, and the shore D hardness of the molded article was measured by using a shore D hardness tester within 10 seconds after the mold was released.
(glass transition temperature)
The sealing resin composition was charged into a transfer molding machine and molded at a mold temperature of 180 ℃ under a molding pressure of 6.9MPa for a curing time of 90 seconds to obtain a rod-shaped molded article (5 mm. times.5 mm. times.20 mm). Using this molded article as a test piece, TMA (thermomechanical Analysis) was carried out at a temperature increase rate of 5 ℃/min using a thermomechanical analyzer (NETZSCH Japan, trade name "TMA 4000 SE"), and The intersection of tangents before and after The inflection point of The obtained graph was defined as The glass transition temperature.
(relative permittivity and dielectric loss tangent)
The sealing resin composition was charged into a vacuum hand press, and was molded at a mold temperature of 175 ℃, a molding pressure of 6.9MPa, and a curing time of 600 seconds, and after-cured at 180 ℃ for 6 hours to obtain a sheet-like cured product (12.5 mm in length, 25mm in width, and 0.2mm in thickness). The plate-like cured product was used as a test piece, and the relative dielectric constant and the dielectric loss tangent at about 60GHz were measured at 25. + -. 3 ℃ using a dielectric constant measuring apparatus (Agilent Technologies, trade name: network analyzer N5227A).
(Water absorption)
The plate-like cured product immediately after production was put into a pressure cooker retort tester at 121 ℃/2.1 atm, and taken out after 24 hours to determine the rate of increase (%) from the mass immediately before the putting.
[ Table 1]
All documents, patent applications, and technical standards described in the present specification are incorporated by reference to the same extent as if each document, patent application, and technical standard was specifically and individually described, and are incorporated by reference into the present specification to the same extent.
The entire disclosure of japanese application No. 2018-182710, applied for 27.9.2018, is incorporated by reference into this specification.
Claims (6)
1. A resin composition for sealing, which contains:
an epoxy resin comprising a multifunctional epoxy resin and a difunctional epoxy resin; and
a curing agent comprising an active ester compound.
2. The sealing resin composition according to claim 1, wherein the polyfunctional epoxy resin contains at least 1 selected from the group consisting of a triphenylmethane type epoxy resin, a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a naphthalene diol aralkyl type epoxy resin, a naphthol aralkyl type epoxy resin, and a dicyclopentadiene type epoxy resin.
3. The sealing resin composition according to claim 1 or 2, wherein the difunctional epoxy resin contains at least 1 selected from the group consisting of a bisphenol F type epoxy resin, a bisphenol a type epoxy resin, a biphenyl aralkyl type epoxy resin, and a naphthalene type epoxy resin.
4. The sealing resin composition according to any one of claims 1 to 3, wherein the mass ratio of the polyfunctional epoxy resin to the total amount of the polyfunctional epoxy resin and the difunctional epoxy resin is 50 to 95 mass%.
5. An electronic component device, comprising:
a support member;
an element disposed on the support member; and
the sealing resin composition according to any one of claims 1 to 4 for sealing the element.
6. A method of manufacturing an electronic component device, comprising:
disposing the element on the support member; and
a step of sealing the element with the sealing resin composition according to any one of claims 1 to 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-182710 | 2018-09-27 | ||
| JP2018182710 | 2018-09-27 | ||
| PCT/JP2019/036837 WO2020066856A1 (en) | 2018-09-27 | 2019-09-19 | Sealing resin composition, electronic component device, and method for manufacturing electronic component device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112771094A true CN112771094A (en) | 2021-05-07 |
Family
ID=69952122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980063108.6A Pending CN112771094A (en) | 2018-09-27 | 2019-09-19 | Resin composition for sealing, electronic component device, and method for manufacturing electronic component device |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPWO2020066856A1 (en) |
| CN (1) | CN112771094A (en) |
| TW (1) | TW202024166A (en) |
| WO (1) | WO2020066856A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7487596B2 (en) | 2020-07-22 | 2024-05-21 | 株式会社レゾナック | Encapsulating resin composition, electronic component device, and method for producing electronic component device |
| WO2022124405A1 (en) * | 2020-12-11 | 2022-06-16 | 昭和電工マテリアルズ株式会社 | Resin composition for molding and high frequency device |
| CN116583548A (en) * | 2020-12-11 | 2023-08-11 | 株式会社力森诺科 | Resin composition for molding and electronic component device |
| JP6870778B1 (en) * | 2020-12-11 | 2021-05-12 | 昭和電工マテリアルズ株式会社 | Resin composition for molding and electronic component equipment |
| JP7460025B2 (en) | 2021-07-16 | 2024-04-02 | 住友ベークライト株式会社 | Resin composition for semiconductor encapsulation and semiconductor device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10168283A (en) * | 1996-12-13 | 1998-06-23 | Hitachi Chem Co Ltd | Epoxy resin molding material for sealing electronic component |
| CN102585438A (en) * | 2011-01-06 | 2012-07-18 | 日立化成工业株式会社 | Epoxy resin composition for encapsulation and electronic component device |
| TW201302835A (en) * | 2011-05-10 | 2013-01-16 | Ajinomoto Kk | Resin composition |
| JP2014036172A (en) * | 2012-08-10 | 2014-02-24 | Ajinomoto Co Inc | Resin composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002201358A (en) * | 2000-12-27 | 2002-07-19 | Hitachi Chem Co Ltd | Sealing material for electronic part, method for sealing electronic part, semiconductor package, and method for making semiconductor package |
| JP5664008B2 (en) * | 2010-08-10 | 2015-02-04 | 日立化成株式会社 | Resin composition, cured resin, wiring board and method for manufacturing wiring board |
| JP2013023666A (en) * | 2011-07-25 | 2013-02-04 | Sekisui Chem Co Ltd | Epoxy resin material, cured product, and plasma-roughened cured product |
| JP6195219B2 (en) * | 2013-06-21 | 2017-09-13 | 味の素株式会社 | Curable resin composition |
| US9257621B2 (en) * | 2013-09-10 | 2016-02-09 | Lg Innotek Co., Ltd. | Epoxy resin composition and light-emitting device package comprising the same |
| JP2018020040A (en) * | 2016-07-21 | 2018-02-08 | 株式会社三洋物産 | Game machine |
| JP7091618B2 (en) * | 2016-09-27 | 2022-06-28 | 住友ベークライト株式会社 | Capacitance type sensor encapsulation resin composition and capacitance type sensor |
-
2019
- 2019-09-19 JP JP2020549089A patent/JPWO2020066856A1/en active Pending
- 2019-09-19 WO PCT/JP2019/036837 patent/WO2020066856A1/en active Application Filing
- 2019-09-19 CN CN201980063108.6A patent/CN112771094A/en active Pending
- 2019-09-25 TW TW108134680A patent/TW202024166A/en unknown
-
2023
- 2023-12-27 JP JP2023221931A patent/JP2024026589A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10168283A (en) * | 1996-12-13 | 1998-06-23 | Hitachi Chem Co Ltd | Epoxy resin molding material for sealing electronic component |
| CN102585438A (en) * | 2011-01-06 | 2012-07-18 | 日立化成工业株式会社 | Epoxy resin composition for encapsulation and electronic component device |
| TW201302835A (en) * | 2011-05-10 | 2013-01-16 | Ajinomoto Kk | Resin composition |
| JP2014036172A (en) * | 2012-08-10 | 2014-02-24 | Ajinomoto Co Inc | Resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2024026589A (en) | 2024-02-28 |
| WO2020066856A1 (en) | 2020-04-02 |
| TW202024166A (en) | 2020-07-01 |
| JPWO2020066856A1 (en) | 2021-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112771094A (en) | Resin composition for sealing, electronic component device, and method for manufacturing electronic component device | |
| JP7452028B2 (en) | Encapsulating resin composition, electronic component device, and method for manufacturing electronic component device | |
| JP7388160B2 (en) | Encapsulating resin composition, electronic component device, and method for manufacturing electronic component device | |
| JP2024091744A (en) | Resin composition for encapsulation, electronic component device and method for manufacturing electronic component device | |
| JP2024149696A (en) | Encapsulating resin composition, electronic component device, and method for producing electronic component device | |
| JP7501818B2 (en) | Molding resin composition and electronic component device | |
| JP7505661B2 (en) | Molding resin composition and electronic component device | |
| WO2020262654A1 (en) | Sealing resin composition, electronic component device, and method for manufacturing electronic component device | |
| JP2020152825A (en) | Resin composition for sealing, electronic component device, and production method for electronic component device | |
| JP7443778B2 (en) | Encapsulating resin composition, electronic component device, and method for manufacturing electronic component device | |
| JP7491223B2 (en) | Encapsulating resin composition, electronic component device, and method for producing electronic component device | |
| JP7396290B2 (en) | Encapsulating resin composition, electronic component device, and method for manufacturing electronic component device | |
| JP2020122071A (en) | Sealing resin composition, electronic component device, and method for manufacturing same | |
| JP7487596B2 (en) | Encapsulating resin composition, electronic component device, and method for producing electronic component device | |
| TWI854997B (en) | Resin composition for sealing, electronic component device and method of manufacturing electronic component device | |
| WO2020189309A1 (en) | Resin composition for sealing, electronic component device, and production method for electronic component device | |
| JP2022021901A (en) | Sealing resin composition, electronic component device and method for producing electronic component device | |
| JP2022011184A (en) | Sealing resin composition and electronic component device | |
| JP2020050793A (en) | Sealing resin composition, electronic component device and method for producing electronic component device | |
| JP2024015914A (en) | Sealing resin composition, electronic component device and method for producing electronic component device | |
| JP2024081463A (en) | Sealing resin composition, electronic component device and method for producing electronic component device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information | ||
| CB02 | Change of applicant information |
Address after: Tokyo, Japan Applicant after: Lishennoco Co.,Ltd. Address before: Tokyo, Japan Applicant before: Showa electrical materials Co.,Ltd. |