CN114008105A - 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
- CN114008105A CN114008105A CN202080046323.8A CN202080046323A CN114008105A CN 114008105 A CN114008105 A CN 114008105A CN 202080046323 A CN202080046323 A CN 202080046323A CN 114008105 A CN114008105 A CN 114008105A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- active ester
- ester compound
- epoxy resin
- sealing
- 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
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- 238000007789 sealing Methods 0.000 title claims abstract description 96
- 239000011342 resin composition Substances 0.000 title claims abstract description 95
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- -1 ester compound Chemical class 0.000 claims abstract description 112
- 239000003822 epoxy resin Substances 0.000 claims abstract description 84
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 84
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 239000004848 polyfunctional curative Substances 0.000 claims description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 44
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 26
- 239000005011 phenolic resin Substances 0.000 description 23
- 150000002989 phenols Chemical class 0.000 description 23
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 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 18
- 239000011256 inorganic filler Substances 0.000 description 17
- 229910003475 inorganic filler Inorganic materials 0.000 description 17
- 239000002245 particle Substances 0.000 description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 14
- 125000004185 ester group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000007822 coupling agent Substances 0.000 description 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- 239000003063 flame retardant Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 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 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004891 communication Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000005350 fused silica glass Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001721 transfer moulding Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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 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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- 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
- 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 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
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- VXYLRHJJKXASIK-UHFFFAOYSA-N benzhydrylbenzene;phenol Chemical compound OC1=CC=CC=C1.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 VXYLRHJJKXASIK-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229930003836 cresol Natural products 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
- 235000014113 dietary fatty acids Nutrition 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
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-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
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000011777 magnesium Substances 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
- 238000005259 measurement Methods 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000006082 mold release agent Substances 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
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical group 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical group 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 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
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 150000003739 xylenols Chemical class 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
- 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
- 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
- MSJIPWGDQODKSK-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)phenyl]phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)O)C=C1 MSJIPWGDQODKSK-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
- 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
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
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- 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
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- 229910052570 clay Inorganic materials 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-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
- 238000006735 epoxidation reaction Methods 0.000 description 1
- DLPPMKSHLIOSFX-UHFFFAOYSA-N ethyl-(3-hydroxypropyl)-dimethylazanium Chemical compound CC[N+](C)(C)CCCO DLPPMKSHLIOSFX-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
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- 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 239000004615 ingredient Substances 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
- 238000011835 investigation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- 239000010445 mica Substances 0.000 description 1
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- 239000011259 mixed solution Substances 0.000 description 1
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- 239000004206 montan acid ester Substances 0.000 description 1
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- 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
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 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
- 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
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 150000004756 silanes Chemical class 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
- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G59/40—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
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- 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
-
- 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
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
-
- 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
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (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 and a curing agent containing an active ester compound, wherein the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.9 or less.
Description
Technical Field
The present invention relates to a sealing resin composition, an electronic component device, and a method for manufacturing an electronic component device.
Background
The transmission loss amount generated by the heat conversion of the radio wave transmitted for communication in the dielectric body is expressed as: the product of frequency, the square root of the relative dielectric constant, and the dielectric loss tangent. That is, since a transmission signal is easily heated in proportion to a frequency, a material of a communication member is required to have low dielectric characteristics in a high frequency band in order to suppress a 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, and describe that the dielectric loss tangent of a cured product can be suppressed to a low level.
[ Prior art documents ]
[ patent document ]
Patent document 1: japanese patent laid-open No. 2012-246367
Patent document 2: japanese patent laid-open No. 2014-114352
Disclosure of Invention
[ problems to be solved by the invention ]
In the field of message communication, radio waves are becoming higher in frequency with an increase in the number of channels and an increase in the amount of messages transmitted. Currently, 5th Generation Mobile Communication Technology (5G) is under investigation all over the world, and several frequency band candidates to be used are in a range of about 30GHz to 70 GHz. Since wireless communication will be mainstream in the future in such a high frequency band, a further reduction in dielectric loss tangent is required for a material used for manufacturing a communication member.
Further, these materials must satisfy process applicability in the fabrication steps of the package. For example, in the case of manufacturing a semiconductor package, a rewiring layer may be formed after a substrate and a chip are sealed with a sealing resin composition, and in this case, an alkaline solution may be used. However, the sealing resin composition using an active ester compound as a curing agent has room for improvement in resistance to a chemical liquid of an alkaline solution.
The present invention has been made in view of the above circumstances, and an object thereof is to provide a resin composition for sealing which can obtain a cured product having a low dielectric loss tangent and excellent chemical resistance, an electronic component device sealed by using the resin composition, and a method for manufacturing an electronic component device sealed by using the resin composition.
[ means for solving problems ]
Specific means for solving the problems include the following aspects.
< 1 > a sealing resin composition comprising an epoxy resin and a hardener comprising an active ester compound, wherein the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.9 or less.
< 2 > the resin composition for sealing according to < 1 > wherein the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.5 or more.
< 3 > the sealing resin composition according to < 1 > or < 2 > wherein the equivalent ratio of the whole hardener to the epoxy resin (whole hardener/epoxy resin) is 0.5 to 1.2.
< 4 > an electronic part device comprising: a support member, an element disposed on the support member, and a cured product of the sealing resin composition according to any one of < 1 > - < 3 > sealing the element.
< 5 > a method for manufacturing an electronic part device, comprising: a step of disposing an element on a support member, and a step of sealing the element with the sealing resin composition according to any one of < 1 > -to < 3 >.
[ Effect of the invention ]
The present disclosure provides a resin composition for sealing which can provide a cured product having a low dielectric loss tangent and excellent chemical resistance, an electronic component device sealed using the resin composition, and a method for manufacturing an electronic component device sealed using the electronic component device.
Detailed Description
In the present disclosure, the term "step" includes a step that is independent from other steps, and includes a step if the purpose of the step is achieved even when the step cannot be clearly distinguished from other steps.
In the numerical range expressed by the expression "to" in the present disclosure, the numerical values described before and after the expression "to" are included as the minimum value and the 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 the other numerical ranges recited in the present disclosure. In the numerical ranges disclosed in the present disclosure, the upper limit or the lower limit of the numerical range may be replaced by the values shown in the examples.
In the present disclosure, each ingredient may contain a plurality of compatible substances. When a plurality of substances corresponding to each component are present in the composition, the content or content of each component means the total content or content of the plurality of substances present in the composition unless otherwise specified.
In the present disclosure, a plurality of particles corresponding to each component may be contained. In the case where a plurality of particles corresponding to each component are present in the composition, the particle diameter of each component means a value concerning a mixture of the plurality of particles present in the composition unless otherwise specified.
In the present disclosure, the "active ester compound" refers to a compound having 1 or more ester groups (active ester groups) reactive with epoxy groups in 1 molecule and having a hardening effect of an epoxy resin.
< resin composition for sealing >
The sealing resin composition of the present disclosure is a sealing resin composition comprising: the epoxy resin composition contains an epoxy resin and a curing agent containing an active ester compound, wherein the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.9 or less.
The inventors of the present invention have studied and found that a cured product obtained by curing the sealing resin composition having the above-described structure has a low dielectric loss tangent and excellent chemical resistance. The reason is not necessarily clear, but is considered as follows.
First, the sealing resin composition of the present disclosure includes an active ester compound as a hardener. Phenol hardeners, amine hardeners, and the like, which are generally used as hardeners for epoxy resins, generate 2-staged hydroxyl groups in the reaction with the epoxy resins. On the other hand, in the reaction between the epoxy resin and the active ester compound, an ester group having a polarity lower than that of the 2-stage hydroxyl group is generated. Therefore, the sealing resin composition of the present disclosure can suppress the dielectric loss tangent of a cured product to be low as compared with a sealing resin composition containing only a curing agent generating a 2-stage hydroxyl group.
Further, the sealing resin composition of the present disclosure has superior chemical resistance liquid as compared to a sealing resin composition in which the equivalent ratio of the active ester compound to the epoxy resin exceeds 0.9. The reason is not necessarily clear, but is considered as follows.
In a sealing resin composition using an active ester compound as a curing agent for an epoxy resin, an ester group is generated in a cured product by a reaction between an epoxy group and an active ester group. The ester group is considered to be a cause of a decrease in the chemical resistance because it is hydrolyzed under alkaline conditions. In the sealing resin composition of the present disclosure, the number of active ester groups relative to epoxy groups is suppressed to a certain level or less. Therefore, it is considered that the formation of ester groups by the reaction of epoxy groups with active ester groups is suppressed, and good chemical resistance is maintained.
From the viewpoint of obtaining good resistance to chemical liquid, the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) in the sealing resin composition may be 0.8 or less, or may be 0.7 or less.
The lower limit value of the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) in the sealing resin composition is not particularly limited. From the viewpoint of reducing the dielectric loss tangent of the cured product, it may be 0.5 or more, or 0.6 or more.
The sealing resin composition of the present disclosure may contain only the active ester compound as the hardener, and may further contain hardeners other than the active ester compound (a phenol hardener, an amine hardener, an acid anhydride hardener, and the like). When the sealing resin composition contains an active ester compound as a curing agent and a curing agent other than the active ester compound, the equivalent ratio of the entire curing agent to the epoxy resin (the entire curing agent/the epoxy resin) is not particularly limited. For example, it may be in the range of 0.5 to 1.2.
In the sealing resin composition of the present disclosure, the active ester compound contains an epoxy group that does not react with an active ester group because the equivalent ratio of the active ester compound to the epoxy resin is 0.9 or less. The epoxy group which does not react with the active ester group may react with a functional group (hydroxyl group, etc.) of the curing agent other than the active ester compound, and also may cause a self-polymerization reaction of the epoxy group. The self-polymerization of the epoxy groups can precede the reaction of the epoxy groups with the active ester groups, resulting in ether linkages. The ether bond is not hydrolyzed under alkaline conditions, and thus good resistance to chemicals is maintained.
(epoxy resin)
The kind of the epoxy resin contained in the sealing resin composition of the present disclosure is not particularly limited.
Specific examples of the epoxy resin include: a novolak type epoxy resin (e.g., a phenol novolak type epoxy resin, an o-cresol novolak type epoxy resin, etc.) obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol a, and bisphenol F, and naphthol compounds such as α -naphthol, β -naphthol, and dihydroxynaphthalene, with an aliphatic aldehyde compound such as formaldehyde, acetaldehyde, and propionaldehyde in the presence of an acidic catalyst to obtain a novolak resin, and epoxidizing the novolak resin; triphenylmethane epoxy resins obtained by subjecting the above phenolic compounds and aromatic aldehyde compounds such as benzaldehyde and salicylaldehyde to condensation or cocondensation in the presence of an acidic catalyst to obtain triphenylmethane phenol resins and subjecting the triphenylmethane phenol resins to epoxidation; a co-polymerization type epoxy resin obtained by co-condensing the phenol compound, the naphthol compound and the aldehyde compound in the presence of an acidic catalyst to obtain a novolac resin and epoxidizing the novolac resin; diglycidyl ethers such as bisphenol a and bisphenol F, i.e., diphenylmethane type epoxy resins; diglycidyl ethers of alkyl-substituted or unsubstituted bisphenols, i.e., biphenyl-type epoxy resins; diglycidyl ethers of a diphenylethylene type epoxy resin; diglycidyl ethers of bisphenol S and the like, i.e., sulfur atom-containing epoxy resins; epoxy resins which are glycidyl ethers of alcohols such as butanediol, polyethylene glycol, and polypropylene glycol; glycidyl ester type epoxy resins which are glycidyl esters of polycarboxylic acid compounds such as phthalic acid, isophthalic acid and tetrahydrophthalic acid; glycidyl amine type epoxy resins, which are obtained by substituting an active hydrogen bonded to a nitrogen atom of aniline, diaminodiphenylmethane, isocyanuric acid, or the like with a glycidyl group; a dicyclopentadiene type epoxy resin obtained by epoxidizing a co-condensation resin of dicyclopentadiene and a phenol compound; alicyclic epoxy resins such as vinylcyclohexene diepoxide, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, and 2- (3, 4-epoxy) cyclohexyl-5, 5-spiro (3, 4-epoxy) cyclohexane-dioxane, which are obtained by epoxidizing an olefin bond in the molecule; glycidyl ether of p-xylene-modified phenol resin, namely p-xylene-modified epoxy resin; glycidyl ether of m-xylene-modified phenol resin, i.e., m-xylene-modified epoxy resin; glycidyl ethers of terpene-modified phenol resins, i.e., terpene-modified epoxy resins; the glycidyl ether of the dicyclopentadiene modified phenol resin is dicyclopentadiene modified epoxy resin; glycidyl ether of cyclopentadiene-modified phenol resin, namely cyclopentadiene-modified epoxy resin; glycidyl ether of the polycyclic aromatic ring modified phenol resin is polycyclic aromatic ring modified epoxy resin; glycidyl ethers of phenol resins containing naphthalene rings, namely naphthalene-type epoxy resins; halogenated phenol novolac type epoxy resins; p-phenylene bisphenol type epoxy resin; trimethylolpropane type epoxy resins; linear aliphatic epoxy resins obtained by oxidizing an olefin bond with a peroxy acid such as peroxyacetic acid; aralkyl type epoxy resins obtained by epoxidizing aralkyl type phenol resins such as phenol aralkyl resins and naphthol aralkyl resins; and so on. Further, epoxy resins such as epoxy resins of acrylic resins can be cited. These epoxy resins may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The epoxy equivalent (molecular weight/number of epoxy groups) of the epoxy resin is not particularly limited. From the viewpoint of balance among various properties such as moldability, reflow resistance and electrical reliability, it is preferably 100 to 1000g/eq, more preferably 150 to 500 g/eq.
The epoxy equivalent of the epoxy resin is determined by using a resin composition according to Japanese Industrial Standards (JIS) K7236: 2009 by the method.
The softening point or melting point of the epoxy resin is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably from 40 ℃ to 180 ℃, and from the viewpoint of handling properties in the production of the sealing resin composition, it is more preferably from 50 ℃ to 130 ℃.
The melting point or softening point of the epoxy resin is set to pass JIS K7234: 1986 and JIS K7233: 1986, the single cylinder rotational viscometer 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.
(hardening agent)
The sealing resin composition of the present disclosure contains at least an active ester compound as a hardener. The sealing resin composition of the present disclosure may include a hardener other than the active ester compound.
As described above, the resin composition for sealing of the present disclosure can suppress the dielectric loss tangent of a cured product to a low level by using an active ester compound as a curing agent.
In addition, the polar group in the cured product increases the water absorption of the cured product, and as a result, by using the active ester compound as the curing agent, the concentration of the polar group in the cured product can be suppressed, and the water absorption of the cured product can be suppressed. Further, by suppressing the water absorption of the cured product, that is, by suppressing the H which is a polar molecule2The content of O can further suppress the dielectric loss tangent of the cured product to a low 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 0.25%. Here, the water absorption of the cured product is a mass increase rate determined by a pressure cooker test (121 ℃, 2.1 atm, 24 hours).
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 a phenol ester compound, a thiophenol ester compound, an N-hydroxylamine ester compound, and an ester compound of a heterocyclic hydroxyl compound.
Examples of the active ester compound include ester compounds obtained from at least one of an aliphatic carboxylic acid and an aromatic carboxylic acid and at least one of an aliphatic hydroxy compound and an aromatic hydroxy compound. An ester compound having an aliphatic compound as a polycondensation component tends to have excellent compatibility with an epoxy resin because it has an aliphatic chain. An ester compound having an aromatic compound as a polycondensation component tends to have excellent heat resistance because it has 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 of an aromatic hydroxyl compound. Among them, preferred is an aromatic ester obtained by a condensation reaction of an aromatic carboxylic acid with a phenolic hydroxyl group of an aromatic hydroxy compound, wherein the aromatic carboxylic acid is a mixture of an aromatic carboxylic acid component obtained by substituting 2 to 4 of the hydrogen atoms of an aromatic ring such as benzene, naphthalene, biphenyl, diphenylpropane, diphenylmethane, diphenyl ether, or diphenylsulfonic acid with a carboxyl group, a 1-valent phenol obtained by substituting 1 of the hydrogen atoms of the aromatic ring with a hydroxyl group, and a polyhydric phenol obtained by substituting 2 to 4 of the hydrogen atoms of the aromatic ring with a hydroxyl group. That is, the aromatic ester preferably has a structural unit derived from the aromatic carboxylic acid component, a structural unit derived from the 1-valent phenol, and a structural unit derived from the polyhydric phenol.
Specific examples of the active ester compound include the following active ester resins described in japanese patent laid-open publication No. 2012-246367: the resin composition has a structure obtained by reacting a phenol resin having a molecular structure in which a phenol compound is formed by the nucleation of an aliphatic cyclic hydrocarbon group, an aromatic dicarboxylic acid or a halide thereof, and an aromatic monohydroxy compound. The active ester resin is preferably a compound represented by the following structural formula (1).
[ solution 1]
In the structural formula (1), R1Is an alkyl group having 1 to 4 carbon atoms, X is a benzene ring, a naphthalene ring, a benzene ring or a naphthalene ring substituted with 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 with an alkyl group having 1 to 4 carbon atoms, k is 0 or 1, and n represents an 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.
[ solution 2]
[ solution 3]
Specific examples of the active ester compound include 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.
[ solution 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 moiety (Z1) selected from the group consisting of a benzoyl group, a naphthoyl group, a benzoyl or naphthoyl group substituted with an alkyl group having 1 to 4 carbon atoms, and an acyl group having 2 to 6 carbon atoms, or a hydrogen atom (Z2), and at least one of Z represents an ester-forming structural moiety (Z1).
[ solution 5]
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 moiety (Z1) selected from the group consisting of a benzoyl group, a naphthoyl group, a benzoyl or naphthoyl group substituted with an alkyl group having 1 to 4 carbon atoms, and an acyl group having 2 to 6 carbon atoms, or a hydrogen atom (Z2), and at least one of Z represents an ester-forming structural moiety (Z1).
Specific examples of the compound represented by the structural formula (2) include the following exemplified compounds (2-1) to (2-6).
[ solution 6]
Specific examples of the compound represented by the structural formula (3) include the following exemplified compounds (3-1) to (3-6).
[ solution 7]
As the active ester compound, commercially available products can be used. As the commercially available active ester compounds, there may be mentioned "EXB 9451", "EXB 9460S" and "HPC-8000-65T" (manufactured by Diegon (DIC) Co., Ltd.) as active ester compounds having a dicyclopentadiene type diphenol structure; "EXB 9416-70 BK", "EXB-8", "EXB-9425" (manufactured by DIC Co., Ltd.) as an active ester compound having an aromatic structure; "DC 808" (manufactured by mitsubishi chemical corporation) which is an active ester compound containing an acetylated product of phenol novolac; "YLH 1026" (manufactured by Mitsubishi chemical corporation) which is an active ester compound containing a benzoyl compound of phenol novolak, and the like.
The active ester compounds can be used alone in 1 kind, also can be combined with more than 2 kinds.
The ester equivalent (molecular weight/active ester number) of the active ester compound is not particularly limited. From the viewpoint of balance among various properties 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 equivalent of the active ester compound is determined by the following equation in accordance with JIS K0070: 1992.
The hardener may contain other hardeners than the active ester compound. In this case, the kind of the other curing agent is not particularly limited, and can be selected according to the desired characteristics of the sealing resin composition. Examples of the other hardeners include a phenol hardener, an amine hardener, an acid anhydride hardener, a polythiol hardener, a polyaminoamide hardener, an isocyanate hardener, and a blocked isocyanate hardener.
Specific examples of the phenol curing agent include: polyhydric phenol compounds such as resorcinol, catechol, bisphenol a, bisphenol F, and substituted or unsubstituted bisphenols; a novolak-type phenol resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenolic 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, with aldehyde compounds such as formaldehyde, acetaldehyde, and propionaldehyde, under an acidic catalyst; 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 phenol resin, m-xylene-modified phenol resin; a melamine-modified phenol resin; terpene-modified phenol resin; dicyclopentadiene type phenol resins and dicyclopentadiene type naphthol resins synthesized from the above-mentioned phenolic compounds and dicyclopentadiene by copolymerization; a cyclopentadiene-modified phenol resin; polycyclic aromatic ring-modified phenol resins; a 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; phenol resins obtained by copolymerizing 2 or more of these. These phenol hardeners may be used alone in 1 kind, or may be used in combination with 2 or more kinds.
The functional group equivalent (hydroxyl group equivalent in the case of a phenol hardener) of the other hardener is not particularly limited. From the viewpoint of balance among various properties such as moldability, reflow resistance and electrical reliability, it is preferably from 70g/eq to 1000g/eq, 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 is determined by the following equation in accordance with JIS K0070: 1992.
The softening point or melting point of the hardener is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably from 40 ℃ to 180 ℃, and from the viewpoint of handling properties in the production of the sealing resin composition, it is more preferably from 50 ℃ to 160 ℃.
The melting point or softening point of the hardener is defined as a value obtained by JIS K7234: 1986 and JIS K7233: 1986, the single cylinder rotational viscometer method.
From the viewpoint of suppressing the dielectric loss tangent of the cured product to a low level, the content of the active ester compound relative to the total mass of the active ester compound and the other curing agent is preferably 50 mass% or more, more preferably 60 mass% or more, and still more preferably 70 mass% or more.
From the viewpoint of suppressing the dielectric loss tangent of the cured product to a low level, the total content of the epoxy resin and the active ester compound based on the total mass of the epoxy resin, the active ester compound, and the other curing agent is preferably 70 mass% or more, more preferably 75 mass% or more, and still more preferably 80 mass% or more.
(hardening accelerator)
The sealing resin composition may contain a hardening accelerator. The type of the curing accelerator is not particularly limited, and can 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 hardening accelerator include diazabicycloalkenes such as 1,5-Diazabicyclo [4.3.0] nonene-5 (1,5-Diazabicyclo [4.3.0] nonene-5, DBN) and 1,8-Diazabicyclo [5.4.0] undecene-7 (1,8-Diazabicyclo [5.4.0] undecene-7, DBU), and cyclic amidine compounds such as 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylhydroxyimidazole and 2-heptadecylimidazole; derivatives of the cyclic amidine compounds; a phenol novolac salt of the cyclic amidine compound or a derivative thereof; compounds having intramolecular polarization, which are obtained by adding a quinone compound such as maleic anhydride, 1, 4-benzoquinone, 2, 5-methoquinone, 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 bisazophenylmethane to these compounds; cyclic amidino compounds such as tetraphenylborate of DBU, tetraphenylborate of DBN, tetraphenylborate of 2-ethyl-4-methylimidazole and tetraphenylborate of N-methylmorpholine; tertiary amine compounds such as pyridine, triethylamine, triethylene diamine, benzyldimethylamine, trimethanolamine, dimethylaminomethanol, and tris (dimethylaminomethyl) phenol; derivatives of the 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 tertiary phosphine and an organic boron compound; a compound having intramolecular polarization obtained by adding the tertiary phosphine or the phosphine compound to a quinone compound such as maleic anhydride, 1, 4-benzoquinone, 2, 5-methoquinone, 1, 4-naphthoquinone, 2, 3-dimethylbenzoquinone, 2, 6-dimethylbenzoquinone, 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone, 2, 3-dimethoxy-1, 4-benzoquinone, or phenyl-1, 4-benzoquinone, or a compound having a pi bond such as bisazophenylmethane; reacting the tertiary phosphine or the phosphine compound with 4-bromophenol, 3-bromophenol, 2-bromophenol, 4-chlorophenol, 3-chlorophenol, 2-chlorophenol, 4-iodinated phenol, 3-iodinated phenol, 2-iodinated phenol, a compound having intramolecular polarization obtained by a dehydrohalogenation step after reacting a halogenated phenol compound such as 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.; tetra-substituted phosphonium such as tetraphenylphosphonium, tetra-substituted phosphonium having no phenyl group bonded to a boron atom such as tetra-p-tolylborate, and tetra-substituted borate; salts of tetraphenylphosphonium with phenol compounds, and the like.
When the sealing resin composition contains a curing accelerator, the amount thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 15 parts by mass, per 100 parts by mass of the resin component (total amount of the epoxy resin and the curing agent). When the amount of the curing accelerator is 0.1 part by mass or more per 100 parts by mass of the resin component, the resin tends to be cured well in a short time. If the amount of the curing accelerator is 30 parts by mass or less based on 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 of the present disclosure 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, aluminum nitride, boron nitride, talc, clay, and mica. An inorganic filler having a flame retardant effect may be used. Examples of the inorganic filler having a flame retardant effect include aluminum hydroxide, magnesium hydroxide, a composite metal hydroxide such as a 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 of 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 increase in viscosity of the sealing resin composition tends to be further suppressed. When the average particle diameter is 100 μm or less, the filling property tends to be further improved. The average particle diameter of the inorganic filler was determined as a volume average particle diameter (D50) by a particle size distribution measuring apparatus using a laser scattering diffraction method.
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 sealing resin composition is preferably 30 to 90% by volume, more preferably 35 to 85% by volume, and still more preferably 40 to 80% by volume. If the content of the inorganic filler is 30 vol% or more of the entire sealing resin composition, the properties of the cured product, such as the thermal expansion coefficient, thermal conductivity, and elastic modulus, tend to be further improved. If the content of the inorganic filler is 90 vol% or less of the entire sealing resin composition, the viscosity of the sealing resin composition tends to be inhibited from increasing, and the flowability and therefore the moldability tend to be improved.
[ various additives ]
The sealing resin composition may contain various additives such as coupling agents, ion exchangers, release agents, flame retardants, and colorants, 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 adhesion between the resin component and the inorganic filler. Examples of the coupling agent include known coupling agents such as silane compounds including epoxy silane, mercapto silane, amino silane, alkyl silane, ureido silane, vinyl silane, and disilazane, titanium compounds, aluminum chelate compounds, and aluminum/zirconium compounds.
When the sealing resin composition contains a coupling agent, the amount of the coupling agent is preferably 0.05 to 15 parts by mass, and more preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the inorganic filler. When 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. When the amount of the coupling agent is 15 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 including a sealed element. The ion exchanger is not particularly limited, and conventionally known ion exchangers can be used. Specifically, there may be mentioned hydrotalcite compounds, hydrous oxides of at least one element selected from the group consisting of magnesium, aluminum, titanium, zirconium and bismuth, and the like. The ion exchanger may be used alone in 1 kind, or in combination of 2 or more kinds. Among them, preferred is hydrotalcite represented by the following general formula (a).
MG(1-X)AlX(OH)2(CO3)X/2·mH2O……(A)
(X is more than 0 and less than or equal to 0.5, and m is a 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 ion plasma. 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 (the total amount of the epoxy resin and the 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. Specific examples thereof include carnauba wax, higher fatty acids such as montanic acid and stearic acid, higher fatty acid metal salts, ester waxes such as montanic acid esters, and polyolefin waxes such as oxidized polyethylene and non-oxidized polyethylene. The mold release agent can be used alone in 1 kind, also can be combined with more than 2 kinds.
When the sealing resin composition contains a release agent, the amount thereof is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the resin component (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, sufficient releasability tends to be obtained. When the amount is 10 parts by mass or less, more favorable adhesion 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 in combination of 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, lead tetraoxide, and red iron oxide. The content of the colorant can be appropriately selected depending on the purpose and the like. The colorant may be used alone in 1 kind, or in combination of 2 or more kinds.
(method for producing sealing resin composition)
The method for producing the sealing resin composition is not particularly limited. As a general method, a method of sufficiently mixing a predetermined amount of components by a mixer or the like, then melt-kneading the mixture by a mixing roll, an extruder or the like, cooling the mixture, and pulverizing the mixture can be mentioned. More specifically, for example, a method of uniformly stirring and mixing predetermined amounts of the above components, kneading the mixture with a kneader, a roll, an extruder or the like heated in advance to 70 to 140 ℃, cooling the mixture, and pulverizing the mixture can be mentioned.
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 a powder, a granule, and a tablet. From the viewpoint of handling properties, the size and mass of the sealing resin composition in the form of a pellet are preferably such that they meet the molding conditions for the package.
< electronic component device >
An electronic component device according to an embodiment of the present disclosure includes: an element, and a cured product of the sealing resin composition of the present disclosure sealing the element.
As an electronic component device, there is one in which an element section, which is obtained by mounting an element (an active element such as a semiconductor chip, a transistor, a diode, or a thyristor, a passive element such as a capacitor, a resistor, or a coil, or the like) on a support member such as a lead frame, a wired carrier tape, a wiring board, glass, a silicon wafer, or an organic substrate, is sealed with a sealing resin composition.
More specifically, a general resin-sealed Integrated Circuit (IC) having a structure in which an element is fixed to a lead frame, a terminal portion of the element such as a bonding pad and the lead portion are connected by wire bonding, a bump or the like, and then the element is sealed by transfer molding or the like using a sealing resin composition is exemplified, such as a Dual Inline Package (DIP), a Plastic Lead Chip Carrier (PLCC), a Quad Flat Package (QFP), a Small Outline Package (SOP), a Small Outline J-lead Package (SOJ), a Thin Small Outline Package (op), a Thin Quad Flat Package (TQFP); a Tape Carrier Package (TCP) having a structure in which a component connected by bumps is sealed on a Carrier Tape with a sealing resin composition; chip On Board (COB) modules, hybrid ICs, multi-Chip modules, and the like having a structure in which elements connected to wiring formed On a support member by wire bonding, flip Chip bonding, solder, or the like are sealed with a sealing resin composition; a Ball Grid Array (BGA) Package, a Chip Size Package (CSP), a Multi-Chip Package (MCP) Package, or the like having a structure in which an element is mounted on the surface of a support member having terminals for connecting a wiring board formed on the back surface thereof, the element and the wiring formed on the support member are connected to each other by bumps or wires, and the element is sealed with a sealing resin composition. In addition, the sealing resin composition can also be preferably used for a printed wiring board.
< method for manufacturing electronic component device >
The method for manufacturing an electronic component device of the present disclosure includes: a step of disposing an element on a 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 general method. The type of the supporting member and the element used for manufacturing the electronic component device is not particularly limited, and a supporting member and an element generally used for manufacturing the electronic component device can be used.
As a method for sealing an element using the sealing resin composition of the present disclosure, a low-pressure transfer molding method, an injection molding method, a compression molding method, and the like can be cited. Of these, low-pressure transfer molding is generally used.
[ examples ]
The embodiments are specifically described below by way of examples, but the scope of the embodiments is not limited to these examples.
< preparation of sealing resin composition >
The following components were mixed in the blending ratios (parts by mass) shown in table 1 to prepare sealing resin compositions of examples and comparative examples.
Epoxy resin 1: triphenylmethane type epoxy resin, epoxy equivalent 167g/eq (Mitsubishi chemical corporation, brand name "1032H 60")
Epoxy resin 2: biphenyl type epoxy resin, epoxy equivalent 186g/eq (Mitsubishi chemical corporation, trade name "YX-4000")
Hardening agent 1: active ester compound manufactured by DIC corporation
Hardener 2: phenol hardener manufactured by Minghe Kangsha Ltd, under the name "MEHC 7851-SS"
Hardening accelerator 1: 2-Ethyl-4-methylimidazole (four kingdoms chemical Co., Ltd.)
Hardening accelerator 2: triphenylphosphine/p-benzoquinone adduct
Coupling agent 1: 3-methacryloxypropyltrimethoxysilane (shin-Etsu chemical industries, Ltd., brand name "KBM-503")
Coupling agent 2: n-phenyl-3-aminopropyltrimethoxysilane (trade name "KBM-573" from shin-Etsu chemical industries, Ltd.)
Mold release agent: montanic acid ester wax (Clarian Japan Co., Ltd.; brand name "HW-E")
The colorant: carbon Black (Mitsubishi chemical corporation, brand name "MA 600")
Filler 1: fused silica (volume average particle diameter 6 μm)
Filler 2: fused silica (volume average particle diameter 0.6 μm)
Filler 3: fused silica (volume average particle diameter 11.2 μm)
< evaluation of Properties of sealing resin composition >
(measurement of relative dielectric constant and dielectric loss tangent)
The sealing resin composition was charged into a transfer molding machine, molded at a mold temperature of 175 ℃, a molding pressure of 2.5MPa and a curing time of 600 seconds, and cured at 175 ℃ for 6 hours to obtain a cured product in the form of a plate (12.5 mm in the vertical direction, 25mm in the horizontal direction, and about 0.2mm in the thickness). A plate-like cured product was used as a test piece, and the relative permittivity and the dielectric loss tangent at a temperature of 25. + -. 3 ℃ and 60GHz were measured using a dielectric constant measuring apparatus (Agilent, trade name "Circuit network Analyzer N5227A").
(spiral flow test)
The flow distance (inch) was determined by molding the sealing resin composition using a mold for spiral flow measurement according to EMMI-1-66 at a mold temperature of 180 ℃, a molding pressure of 6.9MPa, and a curing time of 120 seconds.
(drug resistance test)
The sealing resin composition was charged into a transfer molding machine, and the molding was carried out at a mold temperature of 180 ℃ and a molding pressure of 6.9MPa for a curing time of 90 seconds, followed by curing at 175 ℃ for 6 hours to obtain a cured product in the form of a rod (5 mm. times.5 mm. times.20 mm). A rod-shaped cured product was immersed in a mixed solution of dmso (dimethyl sulfoxide)/tmah (tetramethylammonium hydroxide, 25% AQ.) 92/8 (mass ratio) at 80 ℃ for 1 hour. The remaining rate (% by mass) was calculated from the mass of the test piece after 1 hour by the following formula, using the mass before immersion as a reference.
Residual ratio (% by mass) is (mass (g) after immersion)/mass (g) before immersion) x 100
[ Table 1]
As shown in table 1, the cured product of the sealing resin composition containing an active ester compound as a curing agent had a lower dielectric loss tangent value than the sealing resin composition of comparative example 1 containing no active ester compound as a curing agent.
The sealing resin composition of the example containing an active ester compound as a curing agent and having an equivalent ratio of the active ester compound to the epoxy resin of 0.9 or less was superior in chemical resistance to a cured product thereof, compared to the sealing resin composition of comparative example 2 having an equivalent ratio of the active ester compound to the epoxy resin of 1.0
The disclosure of japanese patent application No. 2019-118699 is incorporated by reference in its entirety into this specification.
All documents, patent applications and technical standards cited in the present specification are cited and incorporated in the present specification to the same extent as if each document, patent application and technical standard was specifically and individually described to be incorporated by reference.
Claims (5)
1. A resin composition for sealing, which contains an epoxy resin and a curing agent containing an active ester compound, wherein the equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.9 or less.
2. The sealing resin composition according to claim 1, wherein an equivalent ratio of the active ester compound to the epoxy resin (active ester compound/epoxy resin) is 0.5 or more.
3. The sealing resin composition according to claim 1 or 2, wherein an equivalent ratio of the entire hardener to the epoxy resin (entire hardener/epoxy resin) is 0.5 to 1.2.
4. An electronic part device comprising: a support member, a device disposed on the support member, and a cured product of the sealing resin composition according to any one of claims 1 to 3 sealing the device.
5. A method for manufacturing an electronic component device includes: a step of disposing an element on a support member, and a step of sealing the element with the sealing resin composition according to any one of claims 1 to 3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-118699 | 2019-06-26 | ||
| JP2019118699 | 2019-06-26 | ||
| PCT/JP2020/025356 WO2020262654A1 (en) | 2019-06-26 | 2020-06-26 | Sealing resin composition, electronic component device, and method for manufacturing electronic component device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114008105A true CN114008105A (en) | 2022-02-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080046323.8A Pending CN114008105A (en) | 2019-06-26 | 2020-06-26 | Resin composition for sealing, electronic component device, and method for manufacturing electronic component device |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2020262654A1 (en) |
| KR (1) | KR20220025804A (en) |
| CN (1) | CN114008105A (en) |
| TW (1) | TW202108655A (en) |
| WO (1) | WO2020262654A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023038035A1 (en) * | 2021-09-09 | 2023-03-16 | 株式会社レゾナック | Sealing resin composition, electronic component device, and method for manufacturing electronic component device |
| WO2023238951A1 (en) * | 2022-06-10 | 2023-12-14 | 株式会社レゾナック | Resin composition for molding and electronic component device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010111859A (en) * | 2008-10-07 | 2010-05-20 | Ajinomoto Co Inc | Epoxy resin composition |
| JP2012246367A (en) * | 2011-05-26 | 2012-12-13 | Dic Corp | Thermosetting resin composition, cured product thereof, semiconductor sealing material, prepreg, circuit board and buildup film |
| JP2015106698A (en) * | 2013-12-02 | 2015-06-08 | 味の素株式会社 | Method for manufacturing semiconductor device |
| JP2019006895A (en) * | 2017-06-23 | 2019-01-17 | 味の素株式会社 | Resin composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11349666A (en) * | 1998-06-05 | 1999-12-21 | Kanagawa University | Epoxy resin composition |
| JP2012246497A (en) * | 2012-09-04 | 2012-12-13 | Sekisui Chem Co Ltd | Resin film, laminate plate, and prepreg |
| JP6070134B2 (en) | 2012-12-07 | 2017-02-01 | Dic株式会社 | Active ester resin, curable resin composition, cured product thereof, and printed wiring board |
| JP6538429B2 (en) * | 2014-10-17 | 2019-07-03 | 太陽インキ製造株式会社 | Dry film, cured product and printed wiring board |
| JP7258453B2 (en) * | 2017-03-31 | 2023-04-17 | 住友ベークライト株式会社 | Thermosetting resin composition, resin film with carrier, prepreg, printed wiring board and semiconductor device |
| JP6512328B2 (en) * | 2018-03-19 | 2019-05-15 | 味の素株式会社 | Resin composition |
-
2020
- 2020-06-26 WO PCT/JP2020/025356 patent/WO2020262654A1/en active Application Filing
- 2020-06-26 CN CN202080046323.8A patent/CN114008105A/en active Pending
- 2020-06-26 KR KR1020227000610A patent/KR20220025804A/en unknown
- 2020-06-26 JP JP2021527800A patent/JPWO2020262654A1/ja active Pending
- 2020-06-29 TW TW109121855A patent/TW202108655A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010111859A (en) * | 2008-10-07 | 2010-05-20 | Ajinomoto Co Inc | Epoxy resin composition |
| JP2012246367A (en) * | 2011-05-26 | 2012-12-13 | Dic Corp | Thermosetting resin composition, cured product thereof, semiconductor sealing material, prepreg, circuit board and buildup film |
| JP2015106698A (en) * | 2013-12-02 | 2015-06-08 | 味の素株式会社 | Method for manufacturing semiconductor device |
| JP2019006895A (en) * | 2017-06-23 | 2019-01-17 | 味の素株式会社 | Resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2020262654A1 (en) | 2020-12-30 |
| KR20220025804A (en) | 2022-03-03 |
| WO2020262654A1 (en) | 2020-12-30 |
| TW202108655A (en) | 2021-03-01 |
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