CN117858924A - Curable resin composition and electronic component device - Google Patents
Curable resin composition and electronic component device Download PDFInfo
- Publication number
- CN117858924A CN117858924A CN202280057840.4A CN202280057840A CN117858924A CN 117858924 A CN117858924 A CN 117858924A CN 202280057840 A CN202280057840 A CN 202280057840A CN 117858924 A CN117858924 A CN 117858924A
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- Prior art keywords
- resin composition
- curable resin
- group
- tan
- temperature
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 168
- 229920005989 resin Polymers 0.000 claims abstract description 75
- 239000011347 resin Substances 0.000 claims abstract description 75
- 239000003822 epoxy resin Substances 0.000 claims description 117
- 229920000647 polyepoxide Polymers 0.000 claims description 117
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 86
- 239000004848 polyfunctional curative Substances 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 238000005259 measurement Methods 0.000 claims description 29
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- 238000007789 sealing Methods 0.000 claims description 4
- -1 polysiloxane Polymers 0.000 description 103
- 239000005011 phenolic resin Substances 0.000 description 75
- 125000004432 carbon atom Chemical group C* 0.000 description 52
- 239000003795 chemical substances by application Substances 0.000 description 51
- 239000000047 product Substances 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 36
- 239000011256 inorganic filler Substances 0.000 description 28
- 229910003475 inorganic filler Inorganic materials 0.000 description 28
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 26
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 24
- 239000002245 particle Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 23
- 125000003118 aryl group Chemical group 0.000 description 22
- 125000000962 organic group Chemical group 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 150000002989 phenols Chemical class 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 239000007822 coupling agent Substances 0.000 description 15
- 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 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- 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 13
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 13
- 229940005561 1,4-benzoquinone Drugs 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- 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 12
- 125000003277 amino group Chemical group 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000004593 Epoxy Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000004104 aryloxy group Chemical group 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
- 239000007795 chemical reaction product Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000007747 plating Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000003566 sealing material Substances 0.000 description 7
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000004780 naphthols Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 5
- 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 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
- 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 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 229930003836 cresol Natural products 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- 238000011282 treatment Methods 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
- 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 3
- BLBVJHVRECUXKP-UHFFFAOYSA-N 2,3-dimethoxy-1,4-dimethylbenzene Chemical group COC1=C(C)C=CC(C)=C1OC BLBVJHVRECUXKP-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
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- 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
- QXHLMWWPSWWKOK-UHFFFAOYSA-N 2,3-dimethylnaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(C)C(C)=CC2=C1 QXHLMWWPSWWKOK-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
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-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
- 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
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- 244000043261 Hevea brasiliensis Species 0.000 description 2
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- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 239000006185 dispersion Substances 0.000 description 2
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
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- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-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
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-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
- 125000006840 diphenylmethane group Chemical group 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
- XHWQYYPUYFYELO-UHFFFAOYSA-N ditridecyl phosphite Chemical compound CCCCCCCCCCCCCOP([O-])OCCCCCCCCCCCCC XHWQYYPUYFYELO-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052839 forsterite Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 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
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection 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
- 230000010354 integration Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 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
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 229910052863 mullite Inorganic materials 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 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 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
- XDHRVAHAGMMFMC-UHFFFAOYSA-N tris(2,4-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC=C1P(C=1C(=CC(C)=CC=1)C)C1=CC=C(C)C=C1C XDHRVAHAGMMFMC-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- CKKFLUXMIUUGAW-UHFFFAOYSA-N tris(2-propan-2-ylphenyl)phosphane Chemical compound CC(C)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(C)C)C1=CC=CC=C1C(C)C CKKFLUXMIUUGAW-UHFFFAOYSA-N 0.000 description 1
- GDKAFTKCUOBEDW-UHFFFAOYSA-N tris(2-tert-butylphenyl)phosphane Chemical compound CC(C)(C)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C GDKAFTKCUOBEDW-UHFFFAOYSA-N 0.000 description 1
- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- SPNVODOGUAUMCA-UHFFFAOYSA-N tris(4-ethoxy-2,6-dimethylphenyl)phosphane Chemical compound CC1=CC(OCC)=CC(C)=C1P(C=1C(=CC(OCC)=CC=1C)C)C1=C(C)C=C(OCC)C=C1C SPNVODOGUAUMCA-UHFFFAOYSA-N 0.000 description 1
- LQEKTSMTEYLBLJ-UHFFFAOYSA-N tris(4-ethoxyphenyl)phosphane Chemical compound C1=CC(OCC)=CC=C1P(C=1C=CC(OCC)=CC=1)C1=CC=C(OCC)C=C1 LQEKTSMTEYLBLJ-UHFFFAOYSA-N 0.000 description 1
- PCCAGZSOGFNURV-UHFFFAOYSA-N tris(4-ethylphenyl)phosphane Chemical compound C1=CC(CC)=CC=C1P(C=1C=CC(CC)=CC=1)C1=CC=C(CC)C=C1 PCCAGZSOGFNURV-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- JTOQWGJGVSYTTN-UHFFFAOYSA-N tris(4-propylphenyl)phosphane Chemical compound C1=CC(CCC)=CC=C1P(C=1C=CC(CCC)=CC=1)C1=CC=C(CCC)C=C1 JTOQWGJGVSYTTN-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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide 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
- C08G59/62—Alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
In a graph obtained by measuring dynamic viscoelasticity of a resin cured product of a curable resin composition, the graph has a vertical axis of tan delta and a horizontal axis of temperature of 30-260 ℃, wherein (1) the maximum tan delta temperature is less than 120 ℃, (2) the maximum tan delta temperature exceeds 0.400, and (3) the total tan delta value at each temperature of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ exceeds 0.400 or the total tan delta value at each temperature of 70 ℃, 80 ℃ and 90 ℃ exceeds 0.600.
Description
Technical Field
The present disclosure relates to a curable resin composition and an electronic component device.
Background
In recent years, high-density mounting of semiconductor elements has been advanced. With this, a surface-mount type package has been the mainstream of the resin-sealed semiconductor device with respect to the conventional pin-inserted type package. Surface-mounted integrated circuits (Integrated Circuit, IC), large-scale integrated circuits (Large Scale Integration, LSI) and the like are thin and small packages for improving the mounting density and reducing the mounting height. Therefore, the occupied area of the element with respect to the package becomes large, and the thickness of the package becomes extremely thin.
Further, these packages are different from the pin-inserted packages in mounting method. That is, since the lead-in package is soldered from the back surface of the wiring board after the lead is inserted into the wiring board, the package is not directly exposed to high temperature.
However, since the surface-mounted IC is temporarily fixed to the surface of the wiring board and is processed by a solder bath, a reflow apparatus, or the like, the package is directly exposed to a soldering temperature (reflow temperature). As a result, in the case of package moisture absorption, moisture absorption and vaporization occur at the time of reflow, and the generated vapor pressure acts as a peeling stress, and peeling between the sealing material and the supporting member such as an element and a lead frame occurs, which causes package cracking, electrical characteristics failure, and the like. Accordingly, it is desired to develop a sealing material which is excellent in adhesion to a support member and further excellent in solder heat resistance (reflow resistance).
As the sealing material, a curable resin composition containing an epoxy resin and a phenolic curing agent is known.
Disclosure of Invention
[ problem to be solved by the invention ]
The curable resin composition proposed in patent document 1 has room for further improvement in reflow resistance.
The present disclosure has been made in view of the above-described circumstances, and an object of the present disclosure is to provide a curable resin composition having excellent reflow resistance and an electronic component device including an element sealed with the curable resin composition.
[ means of solving the problems ]
Specific methods for achieving the above-described object are as follows.
<1> a curable resin composition, wherein in a graph obtained by measuring dynamic viscoelasticity of a resin cured product of the curable resin composition, the vertical axis is tan delta and the horizontal axis is a temperature of 30 ℃ to 260 ℃, (1) the temperature at which tan delta is maximum is less than 120 ℃, (2) the maximum value of tan delta exceeds 0.400, and (3) the sum of tan delta values at each temperature of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ exceeds 0.400.
<2> a curable resin composition, wherein in a graph obtained by measuring dynamic viscoelasticity of a resin cured product of the curable resin composition, the vertical axis is tan delta and the horizontal axis is a temperature of 30 ℃ to 260 ℃, the total tan delta value at each temperature of 70 ℃, 80 ℃ and 90 ℃ exceeds 0.600.
<3> the curable resin composition according to <1> or <2>, wherein when the maximum value of tan δ in the graph is 100, the tan δ value exceeds 60 at least at any of the temperatures of-10 ℃ at which tan δ is the maximum temperature.
<4> the curable resin composition according to any one of <1> to <3>, wherein the storage viscoelasticity at 260℃obtained by subjecting a resin cured product of the curable resin composition to dynamic viscoelasticity measurement is 450MPa or less.
<5> the curable resin composition according to any one of <1> to <4>, wherein the epoxy resin and the phenolic hardener are contained in an equivalent ratio of phenolic hydroxyl groups of the phenolic hardener to epoxy groups of the epoxy resin of 0.5 or more and less than 1.0.
<6> an electronic component device comprising an element and a resin cured product of the curable resin composition according to any one of <1> to <5> sealing the element.
<7> the electronic component device according to <6>, further comprising a support member having the element mounted on one surface thereof.
[ Effect of the invention ]
By the present disclosure, a curable resin composition having excellent reflow resistance and an electronic component device including an element sealed with the curable resin composition can be provided.
Drawings
Without any means for
Detailed Description
Hereinafter, embodiments for implementing the present disclosure will be described in detail. The present disclosure is not limited to the following embodiments. In the following embodiments, the constituent elements (including the element steps) are not necessarily required unless specifically indicated. The values and ranges are also the same and do not limit the disclosure.
In the present disclosure, the numerical values described before and after the use of the numerical values indicated by the "to" include the "to" values as the minimum value and the maximum value, respectively.
In the numerical ranges described in stages in the present disclosure, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in other stages. In the numerical ranges described in the present disclosure, the upper limit or the lower limit of the numerical ranges may be replaced with the values shown in the synthesis examples.
In the present disclosure, a plurality of compounds corresponding to the respective components may be contained. When a plurality of substances corresponding to the respective components are present in the composition, unless otherwise specified, the content or content of the respective components means the total content or content of the plurality of substances present in the composition.
In the present disclosure, a plurality of particles corresponding to each component may be contained. When a plurality of particles corresponding to each component are present in the composition, the particle diameter of each component refers to a value related to a mixture of the plurality of particles present in the composition unless otherwise specified.
In the present disclosure, "stacked" is used to mean that layers are stacked, and two or more layers may be combined or may be attached and detached.
In the expression of the group (radical) of the present disclosure, the expression of not recording substituted and unsubstituted includes both a group having no substituent and a group having a substituent.
In the present disclosure, regarding the number of structural units, an integer value is expressed for a single molecule, and a rational number is expressed as an average value as an aggregate of a plurality of molecules.
In the present disclosure, the carbon number refers to the total number of carbon atoms contained in the whole of a certain group, and when the group has no substituent, the number of carbon atoms forming the skeleton of the group is represented, and when the group has a substituent, the total number of carbon atoms forming the skeleton of the group added to the number of carbon atoms in the substituent is represented.
In the present disclosure, the dynamic viscoelasticity measurement of the resin cured product of the curable resin composition can be performed using a dynamic viscoelasticity measurement device (for example, manufactured by PerkinElmer, DMA 8000). For example, a rectangular resin cured product having a short side of 5mm×a long side of 50mm×a thickness of 2mm may be used in the test mode: 3 point bending mode, measurement temperature: 25-330 ℃, and the temperature rising speed is as follows: 10 ℃/min, test frequency: dynamic viscoelasticity measurement was performed under the condition of 1Hz, and the value of the stored viscoelasticity, the maximum value of tan delta, the temperature at which tan delta becomes the maximum value, and the like were determined from the obtained graphs (vertical axis: tan delta, horizontal axis: temperature).
The resin cured product is produced by: the curable resin composition was molded by a transfer molding machine under conditions of a mold temperature of 175℃and a molding pressure of 8.3MPa and a curing time of 120 seconds, and then post-curing was carried out at 175℃for 5 hours.
In the present disclosure, in the measurement of the coefficient of thermal expansion (Coefficient of Thermal Expansion, CTE) of a resin cured product of a curable resin composition, for example, it is aimed at The resin cured product of (2) is obtained by using a thermo-mechanical analysis device. The cured resin is produced as described above.
The measurement conditions were 15g of load, the measurement temperature was-50℃to 220℃and the heating rate was 5℃per minute.
As the thermo-mechanical analysis device, TMA/SS6100 manufactured by Seiko instruments (Seiko Instruments) Co., ltd.
In the present disclosure, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values obtained by conversion using a calibration curve of standard polystyrene under the following measurement conditions, and measured using the following gel permeation chromatography (Gel Permeation Chromatography, GPC) measurement apparatus. In addition, as standard polystyrene, five sample groups ("PStQuick MP-H" and "PStQuick B", manufactured by Tosoh Co., ltd.) were used in the preparation of the calibration curve.
Among them, as for a compound whose molecular weight is small and whose Mw or Mn cannot be accurately measured by GPC, a molecular weight obtained from the chemical structure of the compound is used as the Mw or Mn of the compound.
(GPC measurement apparatus)
GPC apparatus: high speed GPC apparatus "HCL-8320GPC", detector is differential refractometer or UV manufactured by Tosoh Co., ltd
Tubular column: TSKgel Super Multipore HZ-H (length of column: 15cm, inner diameter of column: 4.6 mm), manufactured by Tosoh Co., ltd
(measurement conditions)
Solvent: tetrahydrofuran (THF)
Measurement temperature: 40 DEG C
Flow rate: 0.35 mL/min
Sample concentration: 10mg/THF 5mL
Injection amount: 20 mu L
[ curable resin composition ]
< curable resin composition of the first aspect >
In the curable resin composition of the first aspect, in a graph obtained by measuring dynamic viscoelasticity of a resin cured product of the curable resin composition, the vertical axis is tan δ and the horizontal axis is 30 to 260 ℃, the temperature at which tan δ is maximum (so-called glass transition temperature) is less than 120 ℃, (2) the maximum value of tan δ exceeds 0.400, and (3) the sum of tan δ values at each temperature of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ exceeds 0.400.
The curable resin composition of the first aspect has excellent reflow resistance.
The reason why the effect is achieved by the curable resin composition of the first aspect is not clear, but is presumed as follows.
According to the curable resin composition of the first aspect, there is a tendency that an internal stress of a resin cured product generated at the time of reflow is relaxed, and in the curable resin composition of the first aspect, in a graph obtained by measuring a dynamic viscoelasticity of a resin cured product of the curable resin composition, a temperature in which a vertical axis is tan δ and a horizontal axis is 30 to 260 ℃, (1) a temperature at which tan δ becomes maximum (so-called glass transition temperature) is less than 120 ℃, (2) a maximum value of tan δ exceeds 0.400, and (3) a total of tan δ values at respective temperatures of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ exceeds 0.400. As a result, the adhesion between the resin cured product of the curable resin composition and the support member is improved, and therefore, excellent reflow resistance is presumed.
As a test for evaluating reflow resistance, a humidity sensitivity level (Moisture Sensitive Level, MSL) test is known as a standard of joint electronic equipment engineering council (Joint Electron Device Engineer Council, JEDEC).
According to the curable resin composition of the present disclosure, even after heating and humidification under conditions of 85 ℃ and relative humidity of 85% and 168 hours (corresponding to MSL grade 1), excellent reflow resistance was exhibited, which was surprising.
In view of reflow resistance of the curable resin composition of the first aspect, the temperature at which tan δ becomes maximum is preferably less than 110 ℃. the lower limit of the temperature at which tan δ is maximum is not particularly limited, and may be 50 ℃ or higher, for example.
In view of reflow resistance of the curable resin composition of the first aspect, the maximum value of tan δ is preferably more than 0.410. the upper limit of the maximum value of tan δ is not particularly limited, and may be 1.0 or less, for example.
The upper limit of the total tan δ value of the curable resin composition of the first embodiment is not particularly limited, and may be, for example, 2.0 or less at each temperature of 220 ℃, 230 ℃, 240 ℃ and 250 ℃.
In terms of reflow resistance of the curable resin composition of the first aspect, when the maximum value of tan δ is set to 100, the tan δ value at least any one of temperatures at which tan δ becomes maximum, namely-10 ℃, is preferably more than 60, more preferably more than 63, and even more preferably more than 65.
In view of reflow resistance of the curable resin composition of the first embodiment, the total tan δ value at each temperature of 70 ℃, 80 ℃ and 90 ℃ is preferably more than 0.600, more preferably more than 0.700. The upper limit of the total tan delta value at each of 70 ℃, 80 ℃ and 90 ℃ is not particularly limited, and may be set to 2.0 or less, for example.
In view of reflow resistance of the curable resin composition of the first aspect, storage viscoelasticity at 260 ℃ obtained by dynamic viscoelasticity measurement of a resin cured product of the curable resin composition is preferably 450MPa or less, more preferably 435MPa or less, and further preferably 420MPa or less. The lower limit of the storage modulus of elasticity is not particularly limited, and may be 150MPa or more, for example.
From the viewpoint of the following property with respect to the support member, the coefficient of thermal expansion (CTE 1) of the cured resin of the curable resin composition of the first aspect, as determined by the thermo-mechanical analysis, at a temperature lower than the glass transition temperature is preferably 15ppm/°c or less, more preferably 13ppm/°c or less, and still more preferably 10ppm/°c or less. The lower limit of the thermal expansion coefficient is not particularly limited, and may be set to 3 ppm/. Degree.C.
From the viewpoint of adhesion to a support member, the coefficient of thermal expansion (CTE 2) at a temperature equal to or higher than the glass transition temperature is preferably 10 ppm/DEG C to 45 ppm/DEG C, more preferably 12 ppm/DEG C to 40 ppm/DEG C, still more preferably 15 ppm/DEG C to 38 ppm/DEG C.
From the viewpoint of reflow resistance, the curable resin composition of the first aspect preferably contains the epoxy resin and the phenolic hardener in an equivalent ratio of phenolic hydroxyl groups of the phenolic hardener to epoxy groups of the epoxy resin of 0.5 or more and less than 1.0.
In the present disclosure, the equivalent ratio of phenolic hydroxyl groups (active hydrogen) of the phenolic hardener to epoxy groups of the epoxy resin (the number of moles of active hydrogen of the phenolic hardener per the number of moles of epoxy groups of the epoxy resin) can be determined as follows: the curable resin composition is subjected to 1 H-Nuclear magnetic resonance 1 H-Nuclear Magnetic Resonance, 1 H-NMR) and is determined from the integral ratio of the protons of the epoxy groups to the protons of the phenolic hydroxyl groups. In addition, the curable resin composition 1 H-NMR was measured under the following conditions.
(measurement conditions)
Measurement device: manufactured by Bruker (Bruker) company, AVANCE3 HD 400Nanobay
Measuring vehicle: dimethyl sulfoxide (dimethyl sulfoxide, DMSO) -d6 (0.7 ml)
Measurement temperature: 25 DEG C
· 1 H resonant frequency: 400MHz
Measurement mode: NPROTON
Cumulative number of times: 16 times
Relaxation time: 1 second
Hereinafter, various materials that can be contained in the curable resin composition of the first embodiment will be described.
(epoxy resin)
The curable resin composition of the first aspect may contain an epoxy resin. The type of the epoxy resin is not particularly limited as long as the epoxy resin is a resin having 2 or more epoxy groups in one molecule. In the present disclosure, the linear polysiloxane compound is not included in the epoxy resin.
Specific examples of the epoxy resin are described below, but the present invention is not limited thereto.
Specifically, there may be mentioned: a novolak type epoxy resin (phenol novolak type epoxy resin, 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, cresol, xylenol, resorcinol, catechol, bisphenol a, bisphenol F, etc., and a naphthol compound such as α -naphthol, β -naphthol, dihydroxynaphthalene, etc., with an aliphatic aldehyde compound such as formaldehyde, acetaldehyde, propionaldehyde, etc., in the presence of an acidic catalyst, and epoxidizing the novolak type epoxy resin; a triphenylmethane-type phenol resin obtained by condensing or co-condensing the phenol compound with an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde in the presence of an acidic catalyst, and epoxidizing the triphenylmethane-type phenol resin; a copolymerized epoxy resin obtained by co-condensing the phenol compound and the naphthol compound with an aldehyde compound in the presence of an acidic catalyst to obtain a novolak resin, and epoxidizing the novolak resin; diphenylmethane-type epoxy resins as diglycidyl ethers of bisphenol a, bisphenol F, and the like; biphenyl epoxy resins as diglycidyl ethers of alkyl-substituted or unsubstituted biphenols; a stilbene type epoxy resin as a diglycidyl ether of a stilbene (styrene) based phenol compound; sulfur atom-containing epoxy resins as diglycidyl ethers of bisphenol S and the like; epoxy resins as glycidyl ethers of alcohols such as butanediol, polyethylene glycol, polypropylene glycol, etc.; glycidyl ester type epoxy resins as glycidyl esters of polycarboxylic acid compounds such as phthalic acid, isophthalic acid, tetrahydrophthalic acid, etc.; glycidylamine-type epoxy resins obtained by substituting active hydrogen bonded to nitrogen atom such as aniline, diaminodiphenylmethane and isocyanuric acid with a glycidyl group; a dicyclopentadiene type epoxy resin obtained by epoxidizing a cocondensated resin of dicyclopentadiene and a phenol compound; alicyclic epoxy resins such as a bisepoxylated vinylcyclohexene, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, and 2- (3, 4-epoxy) cyclohexyl-5, 5-spiro (3, 4-epoxy) cyclohexane-m-dioxane, each obtained by epoxidizing an intramolecular olefin bond; para-xylene modified epoxy resins as glycidyl ethers of para-xylene modified phenol resins; meta-xylene modified epoxy resin as glycidyl ether of meta-xylene modified phenol resin; terpene-modified epoxy resins as glycidyl ethers of terpene-modified phenol resins; dicyclopentadiene modified epoxy resins as glycidyl ethers of dicyclopentadiene modified phenol resins; cyclopentadiene-modified epoxy resins as glycidyl ethers of cyclopentadiene-modified phenol resins; polycyclic aromatic ring-modified epoxy resins as glycidyl ethers of polycyclic aromatic ring-modified phenol resins; naphthalene type epoxy resins as glycidyl ethers of naphthalene ring-containing phenol resins; halogenated phenol novolac type epoxy resins; hydroquinone type epoxy resin; trimethylolpropane type epoxy resin; linear aliphatic epoxy resins obtained by oxidizing olefin bonds with peracids such as peracetic acid; aralkyl type epoxy resins obtained by epoxidizing aralkyl type phenol resins such as phenol aralkyl resins and naphthol aralkyl resins. Further, an aminophenol type epoxy resin which is a glycidyl ether of an aminophenol, and the like can be exemplified as the epoxy resin. One kind of these epoxy resins may be used alone, or two or more kinds may be used in combination.
The biphenyl type epoxy resin is not particularly limited as long as it is an epoxy resin having a biphenyl skeleton. For example, an epoxy resin represented by the following general formula (II) is preferable.
[ chemical 1]
In the formula (II), R 8 The hydrogen atom, the alkyl group having 1 to 12 carbon atoms, or the aromatic group having 4 to 18 carbon atoms may be the same or different. n is an average value and represents an integer of 0 to 10.
The stilbene type epoxy resin is not particularly limited as long as it is an epoxy resin having a stilbene skeleton. For example, an epoxy resin represented by the following general formula (III) is preferable.
[ chemical 2]
In the formula (III), R 9 R is R 10 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. n is an average value and represents an integer of 0 to 10.
The diphenylmethane epoxy resin is not particularly limited as long as it is an epoxy resin having a diphenylmethane skeleton. For example, an epoxy resin represented by the following general formula (IV) is preferable.
[ chemical 3]
In the formula (IV), R 11 R is R 12 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. n is an average value and represents an integer of 0 to 10.
The sulfur atom-containing epoxy resin is not particularly limited as long as it is an epoxy resin containing a sulfur atom. For example, an epoxy resin represented by the following general formula (V) can be mentioned.
[ chemical 4]
In the formula (V), R 13 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. n is an average value and represents an integer of 0 to 10.
The novolak type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidizing a novolak type phenol resin.
[ chemical 5]
In the formula (VI), R 14 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. R is R 15 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3. n is an average value and represents an integer of 0 to 10.
The dicyclopentadiene type epoxy resin is not particularly limited as long as it is an epoxy resin obtained by epoxidation of a compound having a dicyclopentadiene skeleton as a raw material.
[ chemical 6]
In the formula (VII), R 16 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3. n is an average value and represents an integer of 0 to 10.
The triphenylmethane type epoxy resin is not particularly limited as long as it is an epoxy resin using a compound having a triphenylmethane skeleton as a raw material.
[ chemical 7]
In the formula (VIII), R 17 R is R 18 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3, and k each independently represents an integer of 0 to 4. n is an average value and represents an integer of 0 to 10.
The copolymerized epoxy resin obtained by epoxidizing a novolak resin obtained from a naphthol compound and a phenol compound with an aldehyde compound is not particularly limited as long as it is an epoxy resin using a compound having a naphthol skeleton and a compound having a phenol skeleton as raw materials.
For example, an epoxy resin obtained by subjecting a novolac-type phenol resin using a compound having a naphthol skeleton and a compound having a phenol skeleton to glycidyl etherification is preferable, and an epoxy resin represented by the following general formula (IX) is more preferable.
[ chemical 8]
In the formula (IX), R 19 ~R 21 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3, j each independently represents an integer of 0 to 2, and k each independently represents an integer of 0 to 4. l and m are each an average value of 0 to 10, and (l+m) represents a number of 0 to 10. The terminal of the epoxy resin represented by the formula (IX) is either the following formula (IX-1) or formula (IX-2). In the formula (IX-1) and the formula (IX-2), R 19 ~R 21 Definition of i, j and k and R in formula (IX) 19 ~R 21 The definitions of i, j and k are the same. n is 1 (in the case of bonding via a methylene group) or 0 (in the case of bonding without a methylene group).
[ chemical 9]
The epoxy resin represented by the general formula (IX) may be: random copolymers having 1 structural unit and m structural units randomly, alternating copolymers having 1 structural unit and m structural units alternately, copolymers having 1 structural unit and m structural units regularly, block copolymers having 1 structural unit and m structural units in a block form, and the like. Any one of these may be used alone, or two or more may be used in combination.
The aralkyl type epoxy resin is not particularly limited as long as it is an epoxy resin using, as a raw material, a phenol resin synthesized from at least one selected from the group consisting of phenol compounds such as phenol and cresol and naphthol compounds such as naphthol and dimethylnaphthol, and dimethoxy-para-xylene, bis (methoxymethyl) biphenyl or derivatives of these. For example, an epoxy resin obtained by glycidyletherifying at least one selected from the group consisting of phenol compounds such as phenol and cresol and naphthol compounds such as naphthol and dimethylnaphthol with a phenol resin synthesized from dimethoxy paraxylene, bis (methoxymethyl) biphenyl or a derivative of these, and more preferably an epoxy resin represented by the following general formula (X) and general formula (XI) is preferable.
[ chemical 10]
In the formula (X) and the formula (XI), R 38 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. R is R 37 、R 39 ~R 41 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i is an integer of 0 to 3, k is an integer of 0 to 2, and l is an integer of 0 to 4. n is an average value and each independently is an integer of 0 to 10.
R in the general formulae (II) to (XI) 8 ~R 21 R is R 37 ~R 41 The term "may be the same or different, respectively" means, for example, 8 to 88R in the formula (II) 8 May be the same or different. With respect toOther R 9 ~R 21 R is R 37 ~R 41 It is also meant that the numbers of the respective compounds contained in the formulae may be the same or different. In addition, R 8 ~R 21 R is R 37 ~R 41 May be the same or different. For example, R 9 And R is R 10 May be the same or different.
The monovalent organic group having 1 to 18 carbon atoms in the general formulae (III) to (XI) is preferably an alkyl group or an aryl group.
N in the general formulae (II) to (XI) is an average value, and is preferably each independently in the range of 0 to 10. If n is 10 or less, the melt viscosity of the resin component is not excessively high, and the viscosity is reduced during melt molding of the curable resin composition, so that the occurrence of filling failure, deformation of the bonding wire (wire connecting element and lead wire), and the like tends to be suppressed. n is more preferably set to a range of 0 to 4.
From the viewpoint of reflow resistance of the curable resin composition of the first aspect, the epoxy resin is preferably a copolymerized epoxy resin (hereinafter, referred to as a specific copolymerized epoxy resin) including a structural unit derived from an alkylphenol and a structural unit derived from an alkoxynaphthalene. The following structural unit (a) can be mentioned as a structural unit derived from alkylphenol.
[ chemical 11]
In the structural unit, R A Each independently represents a monovalent alkyl group having 1 to 18 carbon atoms, preferably a monovalent alkyl group having 1 to 6 carbon atoms. X represents an integer of 1 to 3.
The following structural unit (b) is exemplified as the structural unit derived from alkoxynaphthalene.
[ chemical 12]
In the structural unit, R B Each independently represents a monovalent alkoxy group having 1 to 18 carbon atoms, preferably a monovalent alkoxy group having 1 to 6 carbon atoms. y represents an integer of 1 to 6.
In addition, the two bonding sites in the structural unit (b) may be present on the same ring of the naphthalene ring or may be present on two rings of the naphthalene ring, respectively.
The specific copolymerized epoxy resin may have the following structural unit (c).
In the following structural units, n is an integer of 1 to 10, preferably an integer of 2 to 8.
In the structural unit (c), the two bonding sites of the naphthalene ring may be present on the same ring of the naphthalene ring or may be present on two rings of the naphthalene ring, respectively.
[ chemical 13]
Examples of the structural unit satisfying the structural unit (c) include the following structural unit (d).
[ chemical 14]
Among the epoxy resins, the epoxy resin preferably contains a specific copolymerization type epoxy resin from the viewpoint of reflow resistance of the curable resin composition of the present disclosure.
In addition, the epoxy resin preferably contains a biphenyl type epoxy resin from the viewpoint of reflow resistance.
The epoxy equivalent of the epoxy resin is not particularly limited. The epoxy equivalent of the epoxy resin is preferably 40g/eq to 1000g/eq, more preferably 45g/eq to 500g/eq, and still more preferably 50g/eq to 350g/eq, from the viewpoint of balance of various properties such as moldability, heat resistance and electric reliability.
The epoxy equivalent of the epoxy resin was set to be as per Japanese Industrial Standard (Japanese Industrial Standards, JIS) K7236: 2009, a value measured by the method of the present invention.
The epoxy resin may be solid or liquid at 25 ℃. In the case where the epoxy resin is solid at 25 ℃, the softening point or melting point of the epoxy resin is not particularly limited.
The softening point or melting point of the epoxy resin is preferably 40 to 180 ℃ from the viewpoint of balance between moldability and heat resistance. In addition, from the viewpoint of workability in the production of the curable resin composition, the softening point or melting point of the epoxy resin is preferably 50 to 130 ℃.
In the present disclosure, the softening point means a softening point obtained by the method of JIS K7234: 1986, measured by the world method.
In the present disclosure, the melting point means that according to JIS K0064: 1992, values determined by visual-based methods.
The Mw of the epoxy resin is preferably 550 to 1050, more preferably 650 to 950, from the viewpoints of reflow resistance, moldability, heat resistance, and the like.
In addition, the Mn of the epoxy resin is preferably 250 to 800, more preferably 350 to 600, from the viewpoints of reflow resistance, moldability, heat resistance, and the like.
The content of the epoxy resin relative to the total mass of the curable resin composition is preferably 0.5 to 60% by mass, more preferably 2 to 50% by mass, and even more preferably 3 to 45% by mass, from the viewpoints of reflow resistance, strength, fluidity, moldability, and the like.
In the case where the epoxy resin contains a specific copolymerized epoxy resin, the content of the specific copolymerized epoxy resin is preferably 50 to 90% by mass, more preferably 55 to 80% by mass, and even more preferably 60 to 75% by mass based on the total mass of the epoxy resin, in terms of reflow resistance of the curable resin composition of the first aspect.
In terms of reflow resistance of the curable resin composition of the first aspect, when the epoxy resin includes a biphenyl type epoxy resin, the content of the biphenyl type epoxy resin relative to the total mass of the epoxy resin is preferably 5 to 40 mass%, more preferably 7 to 35 mass%, and even more preferably 10 to 30 mass%.
(phenolic hardener)
The curable resin composition of the first aspect may contain a phenolic hardener. The type of the phenolic hardener is not particularly limited, and may be selected from those generally used as a component of the curable resin composition. The phenolic hardener may be used alone or in combination of two or more.
Examples of the phenolic hardener include phenol resins and polyhydric phenol compounds having 2 or more phenolic hydroxyl groups in one molecule.
Specific examples of the phenolic hardener are described below, but the invention is not limited thereto.
Examples of the phenolic hardener include: polyhydric phenol compounds such as resorcinol, catechol, bisphenol a, bisphenol F, and substituted or unsubstituted biphenol; a novolak phenol resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol, cresol, xylenol, resorcinol, catechol, bisphenol a, bisphenol F, phenylphenol, aminophenol and other phenol compounds, α -naphthol, β -naphthol, dihydroxynaphthalene and other naphthol compounds, with an aldehyde compound such as formaldehyde, acetaldehyde, propionaldehyde and the like in the presence of an acidic catalyst; an aralkyl type phenol resin such as a phenol aralkyl resin synthesized from the phenolic compound and dimethoxyp-xylene, bis (methoxymethyl) biphenyl, etc.; para-xylene modified phenol resin and/or meta-xylene modified phenol resin; melamine modified phenol resins; terpene modified phenol resins; dicyclopentadiene type phenol resin and dicyclopentadiene type naphthol resin synthesized by copolymerizing the phenol compound and dicyclopentadiene; cyclopentadiene-modified phenol resins; polycyclic aromatic ring-modified phenol resins; biphenyl type phenol resins; a triphenylmethane-type phenol resin obtained by condensing or co-condensing the phenol compound with an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde in the presence of an acidic catalyst; triazine-type phenol resins such as 2- [4- [ (2-hydroxy-3- (2' -ethyl) hexyl) oxy ] -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine; and phenol resins obtained by copolymerizing two or more of these.
In view of reflow resistance of the curable resin composition of the first aspect, the phenolic hardener preferably includes one or more phenolic hardeners selected from the group consisting of an aralkyl type phenolic resin and a novolac type phenolic resin, and more preferably includes both phenolic hardeners. Hereinafter, the phenolic hardener will be described in more detail, but is not limited thereto.
The aralkyl type phenol resin is not particularly limited, and examples thereof include phenol resins synthesized from at least one selected from the group consisting of phenol compounds and naphthol compounds, dimethoxy-para-xylene, bis (methoxymethyl) biphenyl, and derivatives thereof.
Specific examples of the aralkyl type phenol resin include phenol resins represented by the following general formulae (XII) to (XIV).
In the formulae (XII) to (XIV), R 23 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. R is R 22 、R 24 、R 25 R is R 28 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. R is R 26 R is R 27 The hydroxyl group or the monovalent organic group having 1 to 18 carbon atoms may be the same or different. i is an integer of 0 to 3, j is an integer of 0 to 2, k is an integer of 0 to 4, and p is an integer of 0 to 4. n is an average value and each independently is an integer of 0 to 10.
For R in the general formula 22 The term "may be the same or different from each other" as used herein refers to, for example, i R in the general formula (XII) 22 May be the same or different from each other. In addition, R 22 R37 may be the same or different. For example, R 22 R is R 23 May be the same or different.
From the viewpoint of reflow resistance of the curable resin composition of the first aspect, the aralkyl type phenol resin is preferably a phenol resin represented by the general formula (XIII).
In view of reflow resistance of the curable resin composition of the first embodiment, in general formula (XIII), i and k are preferably both 0.
[ 15]
The aralkyl type phenol resin may be a copolymerized type phenol resin with other phenol resins. The copolymerizable phenol resins include: and copolymerized phenol resins of triphenylmethane type phenol resin and aralkyl type phenol resin, copolymerized phenol resins of salicylaldehyde type phenol resin and aralkyl type phenol resin, copolymerized phenol resins of novolak type phenol resin and aralkyl type phenol resin, and the like.
The dicyclopentadiene phenol resin is not particularly limited as long as it is a phenol resin obtained from a compound having a dicyclopentadiene skeleton as a raw material. For example, a phenol resin represented by the following general formula (XV) is preferable.
[ 16]
In the formula (XV), R 29 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3. n is an average value and represents an integer of 0 to 10.
The triphenylmethane type phenol resin is not particularly limited as long as it is a phenol resin obtained by using an aromatic aldehyde compound as a raw material. For example, the phenol resin represented by the following general formula (XVI) is preferable.
[ chemical 17]
/>
In the formula (XVI), R 30 R is R 31 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i is an integer of 0 to 3, and k is an integer of 0 to 4. n is an average value and is an integer of 0 to 10.
The copolymerized phenol resin of the triphenylmethane-type phenol resin and the aralkyl-type phenol resin is not particularly limited as long as it is a copolymerized phenol resin of a phenol resin obtained by using a compound having a benzaldehyde skeleton as a raw material and an aralkyl-type phenol resin. For example, the phenol resin represented by the following general formula (XVII) is preferable.
[ chemical 18]
In the formula (XVII), R 32 ~R 34 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i is an integer of 0 to 3, k is an integer of 0 to 4, and q is an integer of 0 to 5. 1 and m are each an average value and are each independently an integer of 0 to 11. Wherein the sum of l and m is an integer of 1 to 11.
The novolak type phenol resin is not particularly limited as long as it is a phenol resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol compounds and naphthol compounds with an aldehyde compound in the presence of an acidic catalyst. For example, the phenol resin represented by the following general formula (XVIII) is preferable.
[ chemical 19]
In the formula (XVIII), R 35 The monovalent organic groups each representing a hydrogen atom or a carbon number of 1 to 18 may be the same or different. R is R 36 The monovalent organic groups having 1 to 18 carbon atoms may be the same or different. i each independently represents an integer of 0 to 3. n is an average value and represents an integer of 0 to 10.
R in the general formulae (XII) to (XVIII) 22 ~R 36 The term "may be the same or different" as used herein refers to, for example, i R in formula (XII) 22 May be the same or different from each other. Concerning other R 23 ~R 36 It is also meant that the numbers of each contained in the formulae may be the same or different from each other. In addition, R 22 ~R 36 The two may be the same or different. For example, R 22 R is R 23 May be the same or different, R 30 R is R 31 May be the same or different.
In the general formulae (XII) to (XVIII), n is preferably an integer of 0 to 10. If the melt viscosity of the resin component is 10 or less, the melt viscosity of the curable resin composition is not excessively high, and the viscosity is also low during melt molding of the curable resin composition, and filling failure, deformation of bonding wires (wires connecting elements and leads), and the like are less likely to occur. The average n in one molecule is preferably set to a range of 0 to 4.
The hydroxyl equivalent of the phenolic hardener is not particularly limited. From the viewpoint of balance of various properties such as reflow resistance, formability, and electrical reliability, it is preferably 10g/eq to 1000g/eq, more preferably 30g/eq to 500g/eq.
Hydroxyl equivalent means based on the hydroxyl equivalent according to JIS K0070: 1992, a value calculated by measuring the obtained hydroxyl value.
In the case where the phenolic hardener is solid at 25 ℃, the softening point or melting point of the phenolic hardener is not particularly limited. The softening point or melting point of the phenolic hardener is preferably 40 to 180 ℃ from the viewpoint of moldability and heat resistance. In addition, from the viewpoint of workability in producing the curable resin composition, the softening point or melting point of the phenolic hardener is preferably 50 to 130 ℃.
From the viewpoint of reflow resistance of the curable resin composition of the first aspect, the content of the phenolic hardener relative to the total mass of the curable resin composition is preferably 0.5 to 40 mass%, more preferably 1 to 30 mass%, and even more preferably 2 to 20 mass%.
In terms of reflow resistance of the curable resin composition of the first aspect, when the phenol-based curing agent includes an aralkyl-type phenol resin, the content of the aralkyl-type phenol resin relative to the total mass of the phenol-based curing agent is preferably 60 to 95 mass%, and more preferably 65 to 90 mass%.
In terms of reflow resistance of the curable resin composition of the first aspect, when the phenolic hardener includes a novolac-type phenol resin, the content of the novolac-type phenol resin relative to the total mass of the phenolic hardener is preferably 5 to 40 mass%, and more preferably 10 to 30 mass%.
(various additives)
The curable resin composition of the first aspect may contain, in addition to the above-mentioned components, various additives such as a curing accelerator, an inorganic filler, a coupling agent, a stress-relaxing agent, a mold release agent, a colorant, a flame retardant, an ion exchanger, a resin other than an epoxy resin, and a curing agent other than a phenolic curing agent. The curable resin composition may contain various additives known in the art, as required, in addition to the additives exemplified below.
(hardening accelerator)
The curable resin composition of the first aspect may contain a curing accelerator. The type of the hardening accelerator is not particularly limited, and may be selected according to the type of the epoxy resin, desired properties of the curable resin composition, and the like.
The hardening accelerator preferably contains a phosphonium compound from the viewpoints of hardening properties and fluidity. Specific examples of the phosphonium compound include: three-stage phosphines such as triphenylphosphine, diphenyl (p-toluene) phosphine, tris (alkylphenyl) phosphine, tris (alkoxyphenyl) phosphine, tris (alkyl-alkoxyphenyl) phosphine, tris (dialkylphenyl) phosphine, tris (trialkylphenyl) phosphine, tris (tetraalkylphenyl) phosphine, tris (dialkoxyphenyl) phosphine, tris (trialkoxyphenyl) phosphine, tris (tetraalkoxyphenyl) phosphine, trialkylphosphine, dialkylarylphosphine, and alkyldiarylphosphine; a compound having intramolecular polarization, which is formed by adding a pi-bond-containing compound such as maleic anhydride, a quinone compound such as 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; a compound having an intramolecular polarization obtained by a dehydrohalogenation step after reacting a tertiary phosphine with 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 and the like; salts of tetra-substituted phosphonium such as tetraphenyl phosphonium and tetra-substituted boric acid esters such as tetra-p-toluene boric acid ester; salts of tetra-substituted phosphonium with anions after proton detachment from phenol compounds, salts of tetra-substituted phosphonium with anions after proton detachment from carboxylic acid compounds, and the like.
The phosphonium compound preferably contains a compound represented by the following general formula (I-1) (hereinafter, also referred to as a specific hardening accelerator).
[ chemical 20]
In the formula (I-1), R 1 ~R 3 Each independently is a hydrocarbon group of 1 to 18 carbon atoms, R 1 ~R 3 More than two of them can be mutually bonded to form a ring structure, R 4 ~R 7 Each independently is a hydrogen atom, a hydroxyl group or an organic group having 1 to 18 carbon atoms, R 4 ~R 7 More than two of them may be bonded to each other to form a ring structure.
R as the formula (I-1) 1 ~R 3 The "hydrocarbon group having 1 to 18 carbon atoms" described herein includes aliphatic hydrocarbon groups having 1 to 18 carbon atoms and aromatic hydrocarbon groups having 6 to 18 carbon atoms.
From the viewpoint of fluidity, the aliphatic hydrocarbon group having 1 to 18 carbon atoms is preferably 1 to 8 carbon atoms, more preferably 2 to 6 carbon atoms, and still more preferably 4 to 6 carbon atoms.
The aliphatic hydrocarbon group having 1 to 18 carbon atoms may be a linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms, or may be an alicyclic hydrocarbon group having 3 to 18 carbon atoms. From the viewpoint of ease of production, a linear or branched aliphatic hydrocarbon group is preferable.
Specific examples of the linear or branched aliphatic hydrocarbon group having 1 to 18 carbon atoms include: alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, decyl, and dodecyl, allyl, and vinyl groups. The linear or branched aliphatic hydrocarbon group may have a substituent or may not have a substituent. Examples of the substituent include: alkoxy groups such as methoxy, ethoxy, n-butoxy and t-butoxy, aryl groups such as phenyl and naphthyl, hydroxyl groups, amino groups, halogen atoms and the like. The linear or branched aliphatic hydrocarbon group may have two or more substituents, and the substituents may be the same or different. When the linear or branched aliphatic hydrocarbon group has a substituent, the total number of carbon atoms contained in the aliphatic hydrocarbon group and the substituent is preferably 1 to 18. From the viewpoint of hardenability, an unsubstituted alkyl group is preferable, an unsubstituted alkyl group having 1 to 8 carbon atoms is more preferable, and n-butyl, isobutyl, n-pentyl, n-hexyl, and n-octyl are more preferable.
Specific examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms include: cycloalkyl groups such as cyclopentyl, cyclohexyl and cycloheptyl, cycloalkenyl groups such as cyclopentenyl and cyclohexenyl, and the like. The alicyclic hydrocarbon group may have a substituent or may not have a substituent. Examples of the substituent include: alkyl groups such as methyl, ethyl, n-butyl and t-butyl, alkoxy groups such as methoxy, ethoxy, n-butoxy and t-butoxy, aryl groups such as phenyl and naphthyl, hydroxyl groups, amino groups, halogen atoms and the like. The alicyclic hydrocarbon group may have two or more substituents, and the substituents may be the same or different. When the alicyclic hydrocarbon group has a substituent, the total number of carbons contained in the alicyclic hydrocarbon group and the substituent is preferably 3 to 18. In the case where the alicyclic hydrocarbon group has a substituent, the position of the substituent is not particularly limited. From the viewpoint of hardenability, an unsubstituted cycloalkyl group is preferable, an unsubstituted cycloalkyl group having 4 to 10 carbon atoms is more preferable, and a cyclohexyl group, a cyclopentyl group and a cycloheptyl group are more preferable.
The aromatic hydrocarbon group having 6 to 18 carbon atoms is preferably 6 to 14 carbon atoms, more preferably 6 to 10 carbon atoms. The aromatic hydrocarbon group may have a substituent or may not have a substituent. Examples of the substituent include: alkyl groups such as methyl, ethyl, n-butyl and t-butyl, alkoxy groups such as methoxy, ethoxy, n-butoxy and t-butoxy, aryl groups such as phenyl and naphthyl, hydroxyl groups, amino groups, halogen atoms and the like. The aromatic hydrocarbon group may have two or more substituents, and the substituents may be the same or different. When the aromatic hydrocarbon group has a substituent, the total number of carbons contained in the aromatic hydrocarbon group and the substituent is preferably 6 to 18. In the case where the aromatic hydrocarbon group has a substituent, the position of the substituent is not particularly limited.
Specific examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include: phenyl, 1-naphthyl, 2-naphthyl, tolyl, dimethylphenyl, ethylphenyl, butylphenyl, tert-butylphenyl, methoxyphenyl, ethoxyphenyl, n-butoxyphenyl, tert-butoxyphenyl and the like. The position of the substituent in these aromatic hydrocarbon groups may be any of ortho, meta and para. From the viewpoint of fluidity, an unsubstituted aryl group having 6 to 12 carbon atoms or a substituent-containing aryl group having 6 to 12 carbon atoms is preferable, an unsubstituted aryl group having 6 to 10 carbon atoms or a substituent-containing aryl group having 6 to 10 carbon atoms is more preferable, and a phenyl group, a p-tolyl group and a p-methoxyphenyl group are more preferable.
R as the formula (I-1) 1 ~R 3 The term R as described 1 ~R 3 More than two of them can be mutually bonded to form a cyclic structure "means R 1 ~R 3 In (3) are bonded together to form a divalent or trivalent hydrocarbon group. As R at this time 1 ~R 3 Examples of (a) may be listed as follows: an alkylene group such as an ethylene group, a propylene group, a butylene group, a pentylene group, or a hexylene group, an alkenylene group such as an ethynylene group, a propynylene group, or a butynylene group, an aralkylene group such as a methylene phenylene group, an arylene group such as a phenylene group, or an naphthylene group, or an anthrylene group, which may be bonded to a phosphorus atom to form a cyclic structure. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom or the like.
As R in the general formula (I-1) 4 ~R 7 The term "C1-to-C9"18 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aliphatic hydrocarbyloxy group, an aromatic hydrocarbyloxy group, an acyl group, a hydrocarbyloxycarbonyl group, and an acyloxy group which may be substituted or unsubstituted and which may have 1 to 18 carbon atoms.
Examples of the aliphatic hydrocarbon group and the aromatic hydrocarbon group include R 1 ~R 3 Examples of the aliphatic hydrocarbon group and the aromatic hydrocarbon group are as described above.
Examples of the aliphatic hydrocarbyloxy group include: an oxygen atom-bonded structure to the aliphatic hydrocarbon group such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, a 2-butoxy group, a tert-butoxy group, a cyclopropoxy group, a cyclohexyloxy group, a cyclopentyloxy group, an allyloxy group, an ethyleneoxy group and the like; such aliphatic hydrocarbyloxy groups may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom or the like.
Examples of the aromatic hydrocarbyloxy group include: an oxygen group having a structure in which an oxygen atom is bonded to the aromatic hydrocarbon group such as a phenoxy group, methylphenoxy group, ethylphenoxy group, methoxyphenoxy group, butoxyphenoxy group, phenoxyphenoxy group and the like; such an aromatic hydrocarbyloxy group may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom or the like.
Examples of the acyl group include: aliphatic hydrocarbon carbonyl groups such as formyl, acetyl, ethylcarbonyl, butyryl, cyclohexylcarbonyl and allylcarbonyl, aromatic hydrocarbon carbonyl groups such as phenylcarbonyl and methylphenylcarbonyl; such aliphatic hydrocarbon carbonyl group or aromatic hydrocarbon carbonyl group may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a halogen atom or the like.
Examples of the hydrocarbon oxycarbonyl group include: aliphatic hydrocarbon oxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, allyloxycarbonyl and cyclohexyloxycarbonyl, aromatic hydrocarbon oxycarbonyl groups such as phenoxycarbonyl and methylphenoxycarbonyl, and groups in which these aliphatic hydrocarbon carbonyloxy groups and aromatic hydrocarbon carbonyloxy groups are further substituted with alkyl groups, alkoxy groups, aryl groups, aryloxy groups, amino groups, halogen atoms and the like.
Examples of the acyloxy group include: aliphatic hydrocarbon carbonyloxy groups such as methyl carbonyloxy, ethyl carbonyloxy, butyl carbonyloxy, allyl carbonyloxy and cyclohexyl carbonyloxy, aromatic hydrocarbon carbonyloxy groups such as phenyl carbonyloxy and methylphenyl carbonyloxy, and groups in which these aliphatic hydrocarbon carbonyloxy groups and aromatic hydrocarbon carbonyloxy groups are further substituted with alkyl groups, alkoxy groups, aryl groups, aryloxy groups, amino groups, halogen atoms and the like.
R as the general formula (I-1) 4 ~R 7 The term R as described 4 ~R 7 More than two of them can be mutually bonded to form a ring structure "means 2-4R 4 ~R 7 Bonding can form a 2-4-valent organic group as a whole. As R at this time 4 ~R 7 Examples of the method include: alkylene groups such as ethylene, propylene, butylene, pentylene, and hexylene, alkenylene groups such as ethynylene, propynylene, and butynylene, aralkylene groups such as methylenephenylene, substituents which may form a cyclic structure such as arylene groups such as phenylene, naphthylene, and anthrylene, and oxy groups and dioxy groups thereof. These substituents may be further substituted with an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an amino group, a hydroxyl group, a halogen atom or the like.
R as the general formula (I-1) 4 ~R 7 The method is not particularly limited. For example, it is preferable that each is independently selected from a hydrogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group. Among them, from the viewpoint of easiness in obtaining a raw material, a hydrogen atom, a hydroxyl group, an aryl group which is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group and an alkoxy group, or a chain or cyclic alkyl group is preferable. Examples of the aryl group which is unsubstituted or substituted with at least one selected from the group consisting of an alkyl group and an alkoxy group include: phenyl, p-tolyl, m-tolyl, o-tolyl, p-methoxyphenyl, and the like. Examples of the chain or cyclic alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, t-butyl, octyl, cyclohexyl, and the like. From the viewpoint of hardenability In terms of, R is preferred 4 ~R 7 All of which are hydrogen atoms, or R 4 ~R 7 At least one of them is a hydroxyl group and all the others are hydrogen atoms.
In the general formula (I-1), R is more preferable 1 ~R 3 More than 2 of them are alkyl groups with 1-18 carbon atoms or cycloalkyl groups with 3-18 carbon atoms, R 4 ~R 7 All hydrogen atoms or at least one hydroxyl group, and all the rest hydrogen atoms. Further preferably R 1 ~R 3 All of them are C1-18 alkyl or C3-18 cycloalkyl, R 4 ~R 7 All hydrogen atoms or at least one hydroxyl group, and all the rest hydrogen atoms.
From the viewpoint of rapid hardenability, the specific hardening accelerator preferably contains a compound represented by the following general formula (I-2).
[ chemical 21]
In the formula (I-2), R 1 ~R 3 Each independently is a hydrocarbon group of 1 to 18 carbon atoms, R 1 ~R 3 More than two of them can be mutually bonded to form a ring structure, R 4 ~R 6 Each independently is a hydrogen atom or an organic group having 1 to 18 carbon atoms, R 4 ~R 6 More than two of them may be bonded to each other to form a ring structure.
R in the formula (I-2) 1 ~R 6 Specific examples of (C) are respectively as described for R in the general formula (I-1) 1 ~R 6 The specific examples of (a) are the same, and the preferable ranges are also the same.
The specific hardening accelerator is obtainable, for example, as an adduct of a tertiary phosphine compound and a quinone compound.
Specific examples of the tertiary phosphine compound include: triphenylphosphine, tributylphosphine, dibutylphenylphosphine, butyldiphenylphosphine, ethyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris (4-ethylphenyl) phosphine, tris (4-n-propylphenyl) phosphine, tris (4-n-butylphenyl) phosphine, tris (isopropylphenyl) phosphine, tris (t-butylphenyl) phosphine, tris (2, 4-dimethylphenyl) phosphine, tris (2, 6-dimethylphenyl) phosphine, tris (2, 4, 6-trimethylphenyl) phosphine, tris (2, 6-dimethyl-4-ethoxyphenyl) phosphine, tris (4-methoxyphenyl) phosphine, tris (4-ethoxyphenyl) phosphine and the like. Triphenylphosphine and tributylphosphine are preferable from the viewpoint of moldability.
Specific examples of the quinone compound include: 1, 2-benzoquinone, 1, 4-benzoquinone, diphenoquinone, 1, 4-naphthoquinone, anthraquinone, and the like. From the viewpoint of moisture resistance and storage stability, 1, 4-benzoquinone is preferable.
Specific examples of the specific hardening accelerator include: an addition reaction product of triphenylphosphine and 1, 4-benzoquinone, an addition reaction product of tri-n-butylphosphine and 1, 4-benzoquinone, an addition reaction product of tricyclohexylphosphine and 1, 4-benzoquinone, an addition reaction product of dicyclohexylphenylphosphine and 1, 4-benzoquinone, an addition reaction product of cyclohexyldiphenylphosphine and 1, 4-benzoquinone, an addition reaction product of triisobutylphosphine and 1, 4-benzoquinone, an addition reaction product of tricyclopentylphosphine and 1, 4-benzoquinone, and the like.
The curable resin composition may contain a curing accelerator other than the phosphonium compound.
Specific examples of the hardening accelerator other than the phosphonium compound include: cyclic amidine compounds such as diazabicycloolefins such as 1,5-Diazabicyclo [4.3.0] nonene-5 (1, 5-diazabicycloo [4.3.0] nonene-5, DBN), 1,8-Diazabicyclo [5.4.0] undecene-7 (1, 8-diazabicycloo [5.4.0] undecene-7, DBU), 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-heptadecylimidazole; derivatives of the cyclic amidine compounds; a phenol novolac salt of the cyclic amidine compound or a derivative thereof; a compound having intramolecular polarization, which is formed 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 pi bond such as diazophenylmethane to these compounds; cyclic amidinium 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, triethylenediamine, benzyl dimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol, and the like; 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, and tetrapropylammonium hydroxide.
When the curable resin composition contains a specific curing accelerator as the curing accelerator, the content of the specific curing accelerator is preferably 30 mass% or more, more preferably 50 mass% or more, and still more preferably 70 mass% or more of the entire curing accelerator.
When the curable resin composition contains a curing accelerator, the amount of the curing accelerator 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. When the amount of the hardening accelerator is 0.1 part by mass or more based on 100 parts by mass of the resin component, the hardening accelerator tends to be satisfactorily cured in a short time. If the amount of the hardening accelerator is 30 parts by mass or less based on 100 parts by mass of the resin component, the hardening rate is not excessively high, and a good molded article tends to be obtained.
(inorganic filler)
The curable resin composition of the first aspect may contain an inorganic filler. The curable resin composition contains an inorganic filler, so that hygroscopicity of the curable resin composition tends to be reduced and strength in a cured state tends to be improved. When the curable resin composition is used as a sealing material for a semiconductor package, it is preferable to contain an inorganic filler.
The kind of the inorganic filler is not particularly limited. Specifically, there may be mentioned: silica such as spherical silica and crystalline silica, glass, alumina, calcium carbonate, zirconium silicate, calcium silicate, silicon nitride, aluminum nitride, boron nitride, beryllium oxide, zirconium oxide, zircon, forsterite, steatite, spinel, mullite, titanium oxide, talc, clay, mica, and other inorganic materials. Inorganic fillers having a flame retardant effect may also be used. Examples of the inorganic filler having a flame retardant effect include: composite metal hydroxides such as aluminum hydroxide, magnesium hydroxide, and composite hydroxide of magnesium and zinc, and zinc borate. Among them, spherical silica is preferable from the viewpoint of a decrease in linear expansion coefficient, and alumina is preferable from the viewpoint of high thermal conductivity. The inorganic filler may be used alone or in combination of two or more. The state of the inorganic filler may be: powder, particles to spheroidize the powder, fibers, and the like.
The inorganic filler may be used alone or in combination of two or more.
The shape of the inorganic filler is not particularly limited, and examples thereof include: powdery, spherical, fibrous, etc. The curable resin composition is preferably spherical in terms of fluidity and mold abrasion during molding.
The average particle diameter of the inorganic filler is not particularly limited. The volume average particle diameter of the inorganic filler is preferably 0.1 μm to 50 μm, more preferably 0.3 μm to 30 μm, and still more preferably 0.5 μm to 25 μm, from the viewpoint of balance of viscosity, filling property, and the like of the curable resin composition.
The average particle diameter of the inorganic filler can be measured as a volume average particle diameter (D50) by a laser diffraction scattering particle size distribution measuring apparatus.
The volume average particle diameter can be measured by a known method. As an example, an inorganic filler is extracted from a curable resin composition or a cured resin using an organic solvent, nitric acid, aqua regia, or the like, and sufficiently dispersed by an ultrasonic dispersing machine or the like to prepare a dispersion. The volume average particle diameter of the inorganic filler can be measured from the volume-based particle size distribution measured by a laser diffraction scattering particle size distribution measuring apparatus using the dispersion. Alternatively, the volume average particle diameter of the inorganic filler may be measured from a volume-based particle size distribution obtained by observing the obtained cross section with a scanning electron microscope by embedding the resin cured product in a transparent epoxy resin or the like and polishing the resin cured product to obtain the cross section. Further, the measurement can be performed as follows: a two-dimensional cross-sectional view of the resin cured product is continuously observed using a Focused Ion Beam (FIB) device (a Focused Ion Beam scanning electron microscope (Scanning Electron Microscope, SEM)) or the like, and a three-dimensional structure analysis is performed.
In the case where the curable resin composition contains an inorganic filler, the content of the inorganic filler is not particularly limited. The amount of the curable resin composition is preferably 30 to 90% by mass, more preferably 35 to 80% by mass, and still more preferably 40 to 70% by mass.
When the content of the inorganic filler is 30 mass% or more of the entire curable resin composition, the thermal expansion coefficient, thermal conductivity, elastic modulus, and other properties of the cured resin tend to be further improved.
If the content of the inorganic filler is 90 mass% or less of the entire curable resin composition, the viscosity of the curable resin composition is suppressed from rising, and the fluidity is further improved, so that the moldability tends to be further improved.
(coupling agent)
The curable resin composition of the first aspect may contain a coupling agent. The kind of the coupling agent is not particularly limited, and a known coupling agent can be used. Examples of the coupling agent include a silane coupling agent and a titanium coupling agent. The coupling agent may be used alone or in combination of two or more.
The silane coupling agent is not particularly limited as long as it is a compound other than the linear polysiloxane compound, and examples thereof include: 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, 3-glycidoxypropyl methyldiethoxysilane, 3-glycidoxypropyl methyldimethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-aminopropyl triethoxysilane, 3- (2-aminoethyl) aminopropyl trimethoxysilane, 3- (2-aminoethyl) aminopropyl triethoxysilane, 3-aminopropyl trimethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane, 3-mercaptopropyl triethoxysilane, 3-ureidopropyl triethoxysilane, octenyl trimethoxysilane, glycidoxctyl trimethoxysilane, methacryloxyoctyl trimethoxysilane, and the like.
Examples of the titanium coupling agent include: isopropyl triisostearoyl titanate, isopropyl tris (dioctyl pyrophosphate) titanate, isopropyl tris (N-aminoethyl) titanate, tetraoctyl bis (ditridecyl phosphite) titanate, tetra (2, 2-diallyloxymethyl-1-butyl) bis (ditridecyl phosphite) titanate, bis (dioctyl pyrophosphate) oxyacetate titanate, bis (dioctyl pyrophosphate) ethylene titanate, isopropyl trioctanoyl titanate, isopropyl isostearoyl titanate, isopropyl tri-dodecylbenzenesulfonyl titanate, isopropyl isostearoyl diacrylate titanate, isopropyl tris (dioctyl phosphate) titanate, isopropyl tricumylphenyl titanate, tetraisopropyl bis (dioctyl phosphite) titanate, and the like.
Among the coupling agents, the curable resin composition of the first aspect preferably contains at least one of 3-aminopropyl trimethoxysilane and 3-glycidoxypropyl trimethoxysilane from the viewpoint of reflow resistance.
When the curable resin composition contains a coupling agent, the content of the coupling agent is preferably 0.001 to 10 parts by mass, more preferably 0.01 to 8 parts by mass, and even more preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the inorganic filler contained in the curable resin composition, in terms of adhesion of the interface between the epoxy resin and the inorganic filler.
(stress relaxation agent)
The curable resin composition of the first aspect may contain a stress-relaxing agent such as silicone oil or silicone rubber particles. The curable resin composition contains a stress-relieving agent, thereby further reducing warpage of the package and occurrence of package cracks. The stress-relaxing agent may be a conventionally used known stress-relaxing agent (flexible agent). Specifically, as the stress-relaxing agent, there may be mentioned: thermoplastic elastomers such as silicone, styrene, olefin, urethane, polyester, polyether, polyamide, and polybutadiene, rubber particles such as Natural Rubber (NR), acrylonitrile-butadiene copolymer (acrylonitrile butadiene rubber, NBR), acrylic rubber, urethane rubber, and silicone powder, and rubber particles having a core-shell structure such as methyl methacrylate-styrene-butadiene copolymer (methyl methacrylate butadiene styrene, MBS), methyl methacrylate-silicone copolymer, and methyl methacrylate-butyl acrylate copolymer. The stress-relaxing agent may be used alone or in combination of two or more. Among them, silicone-based stress relaxation agents are preferable. As the silicone-based stress relaxation agent, there can be mentioned: silicone-based stress-relaxing agents having an epoxy group, silicone-based stress-relaxing agents having an amino group, silicone-based stress-relaxing agents obtained by modifying these with polyether, and the like.
When the curable resin composition contains a stress-relieving agent, the content of the stress-relieving agent is preferably 0.1 to 30 parts by mass, more preferably 1 to 5 parts by mass, based on 100 parts by mass of the epoxy resin contained in the curable resin composition.
(Release agent)
In the case of using a mold at the time of molding, the curable resin composition of the first aspect may contain a release agent from the viewpoint of releasability from the mold. The release agent is not particularly limited, and a previously known release agent may be used. As the release agent, there may be mentioned: and ester waxes such as palm wax (carnauba wax), higher fatty acids such as octacosanoic acid and stearic acid, higher fatty acid metal salts and octacosanoic acid esters, and polyolefin waxes such as oxidized polyethylene and nonoxidized polyethylene. The release agent may be used alone or in combination of two or more.
When the curable resin composition of the first aspect contains a release agent, the content of the release agent is preferably 0.01 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the epoxy resin contained in the curable resin composition. When the amount of the release agent is 0.01 parts by mass or more relative to 100 parts by mass of the resin component, releasability tends to be sufficiently obtained. When the amount is 15 parts by mass or less, a better releasability tends to be obtained.
(colorant)
The curable resin composition of the first aspect may contain a colorant. Examples of the coloring agent include: known colorants such as carbon black, organic dyes, organic pigments, titanium oxide, lead oxide, and iron oxide. The content of the colorant may be appropriately selected depending on the purpose and the like. The colorant may be used alone or in combination of two or more.
When the curable resin composition contains a colorant, the content of the colorant is preferably 0.01 to 5% by mass, more preferably 0.05 to 3% by mass, and still more preferably 0.01 to 1% by mass.
(flame retardant)
The curable resin composition of the first aspect may contain a flame retardant. The flame retardant is not particularly limited, and a previously known flame retardant may be used. Examples of the flame retardant include organic compounds or inorganic compounds containing halogen atoms, antimony atoms, nitrogen atoms or phosphorus atoms, metal hydroxides, and the like. The flame retardant may be used singly or in combination of two or more.
In the case where the curable resin composition of the first aspect contains a flame retardant, the content of the flame retardant is not particularly limited as long as it is a sufficient amount to obtain a desired flame retardant effect. The content of the flame retardant is preferably 1 to 300 parts by mass, more preferably 2 to 150 parts by mass, based on 100 parts by mass of the epoxy resin contained in the curable resin composition.
(ion exchanger)
The curable resin composition of the first aspect may contain an ion exchanger. When the curable resin composition is used as a sealing material for a semiconductor package, it is preferable to contain an ion exchanger in terms of improving the moisture resistance and the high-temperature storage characteristics of an electronic component device including a sealed element.
The ion exchanger is not particularly limited, and any known ion exchanger can be used. Specifically, hydrotalcite compounds, hydroxides containing at least one element selected from the group consisting of magnesium, aluminum, titanium, zirconium and bismuth, and the like are exemplified. The ion exchanger may be used alone or in combination of two or more. Specifically, the ion exchanger may be hydrotalcite represented by the following general formula (a).
Mg (1-X) Al X (OH) 2 (CO 3 ) X/2 ·mH 2 O……(A)
(0<X is less than or equal to 0.5, m is a positive number)
In the case where the curable resin composition of the first aspect contains an ion exchanger, the content of the ion exchanger is not particularly limited as long as it is a sufficient amount for capturing halogen ion plasma. The content of the ion exchanger is preferably 0.1 to 30 parts by mass, more preferably 1 to 5 parts by mass, based on 100 parts by mass of the epoxy resin contained in the curable resin composition.
(resins other than epoxy resins)
The curable resin composition of the first aspect may contain a resin other than an epoxy resin. The types of resins other than the epoxy resin are not particularly limited, and may be selected from those generally used as components of curable resin compositions. The resin other than the epoxy resin may be used singly or in combination of two or more.
Specific examples of the resin other than the epoxy resin are described below, but the present invention is not limited thereto.
Examples of the resin other than the epoxy resin include: thiol resins, urea resins, melamine resins, urethane resins, silicone resins, maleimide resins, unsaturated polyester resins, and the like.
(curing agent other than phenolic curing agent)
The curable resin composition of the first aspect may contain a curing agent other than the phenolic curing agent. The type of the curing agent other than the phenol curing agent is not particularly limited, and may be selected from those generally used as a component of the curable resin composition. The curing agent other than the phenol curing agent may be used singly or in combination of two or more.
Specific examples of the curing agent other than the phenolic curing agent are described below, but the present invention is not limited thereto.
Examples of the curing agent other than the phenolic curing agent include: amine-based hardeners, acid anhydride-based hardeners, polythiol-based hardeners, polyaminoamide-based hardeners, isocyanate-based hardeners, blocked isocyanate-based hardeners, and the like.
In the case where the hardener other than the phenol hardener includes an amine hardener, the active hydrogen equivalent of the amine hardener is not particularly limited. From the viewpoint of balance of various properties such as reflow resistance, formability, and electrical reliability, it is preferably 10g/eq to 1000g/eq, more preferably 30g/eq to 500g/eq.
The active hydrogen equivalent of the amine-based hardener means that based on the composition according to JIS K7237: 1995, the amine number obtained was measured.
When the curable resin composition contains a curing agent other than a phenolic curing agent, the content of the curing agent other than a phenolic curing agent relative to the total mass of the curable resin composition is not particularly limited, and is preferably 2 to 35 mass%, more preferably 5 to 30 mass%.
[ method for producing curable resin composition of first aspect ]
The method for producing the curable resin composition is not particularly limited. As a general method, the following methods are listed: after the components of a predetermined amount are sufficiently mixed by a mixer or the like, melt-kneading is performed by a mixing roll, an extruder or the like, and the mixture is cooled and pulverized. More specifically, the following methods are exemplified: the components are uniformly stirred and mixed in predetermined amounts, kneaded by a kneader, a roll, an extruder, etc. preheated to 70 to 140 ℃, cooled, and pulverized.
The curable resin composition is preferably solid at 25 ℃. In the case where the curable resin composition is solid at 25 ℃, the shape of the curable resin composition is not particularly limited, and examples thereof include powder, granule, tablet, and the like. From the viewpoint of handleability, the size and quality of the sheet-like curable resin composition are preferably such that they match the molding conditions of the package.
< curable resin composition of the second aspect >
In the curable resin composition according to the second aspect, in the graph obtained by measuring the dynamic viscoelasticity of the cured resin product of the curable resin composition, the sum of tan δ values at each temperature of 70 ℃, 80 ℃ and 90 ℃ exceeds 0.600, with the vertical axis being tan δ and the horizontal axis being a temperature of 30 ℃ to 260 ℃.
The curable resin composition of the second embodiment has excellent reflow resistance.
The reason why the effect is achieved by the curable resin composition of the second aspect is not clear, but is presumed as follows.
According to the curable resin composition of the second aspect, there is a tendency that the internal stress of the cured resin product generated during reflow is relaxed, and in the curable resin composition of the second aspect, in a graph obtained by dynamic viscoelasticity measurement of the cured resin product of the curable resin composition, the vertical axis is tan δ and the horizontal axis is a temperature of 30 to 260 ℃, the total tan δ value at each temperature of 70 ℃, 80 ℃ and 90 ℃ exceeds 0.600. As a result, the adhesion between the resin cured product of the curable resin composition and the support member is improved, and therefore, excellent reflow resistance is presumed.
According to the curable resin composition of the present disclosure, even after heating and humidification under conditions of 85 ℃ and relative humidity of 85% and 168 hours (corresponding to MSL grade 1), excellent reflow resistance was exhibited, which was surprising.
In view of reflow resistance of the curable resin composition of the second embodiment, the total tan δ value at each temperature of 70 ℃, 80 ℃ and 90 ℃ is preferably more than 0.700. The upper limit of the total tan delta value at each of 70 ℃, 80 ℃ and 90 ℃ is not particularly limited, and may be set to 2.0 or less, for example.
In view of reflow resistance of the curable resin composition of the second embodiment, the temperature at which tan δ becomes maximum is preferably less than 120 ℃, more preferably less than 110 ℃. the lower limit of the temperature at which tan δ is maximum is not particularly limited, and may be 50 ℃ or higher, for example.
In view of reflow resistance of the curable resin composition of the second embodiment, the maximum value of tan δ is preferably more than 0.400, more preferably more than 0.410. the upper limit of the maximum value of tan δ is not particularly limited, and may be 1.0 or less, for example.
In view of reflow resistance of the curable resin composition of the second embodiment, the total tan δ value at each temperature of 20 ℃, 230 ℃, 240 ℃ and 250 ℃ is preferably more than 0.400. The upper limit of the total tan delta values at the respective temperatures of 20 ℃, 230 ℃, 240 ℃ and 250 ℃ is not particularly limited, and may be set to 2.0 or less, for example.
In terms of reflow resistance of the curable resin composition of the second aspect, when the maximum value of tan δ is set to 100, the tan δ value at least any one of temperatures of-10 ℃ at which tan δ is maximum is preferably more than 60, more preferably more than 63, and even more preferably more than 65.
From the viewpoint of reflow resistance, the storage viscoelasticity at 260℃obtained by subjecting a resin cured product of the curable resin composition to dynamic viscoelasticity measurement is preferably 450MPa or less, more preferably 435MPa or less, and still more preferably 420MPa or less. The lower limit of the storage modulus of elasticity is not particularly limited, and may be 150MPa or more, for example.
The coefficient of thermal expansion (CTE 1) of the cured resin of the curable resin composition of the second aspect, as determined by thermal mechanical analysis, at a temperature below the glass transition temperature is preferably 15ppm/°c or less, more preferably 13ppm/°c or less, and even more preferably 10ppm/°c or less, from the viewpoint of the followability to the support member. The lower limit of the thermal expansion coefficient is not particularly limited, and may be set to 3 ppm/. Degree.C.
From the viewpoint of adhesion to a support member, the coefficient of thermal expansion (CTE 2) at a temperature equal to or higher than the glass transition temperature is preferably 10 ppm/DEG C to 45 ppm/DEG C, more preferably 12 ppm/DEG C to 40 ppm/DEG C, still more preferably 15 ppm/DEG C to 38 ppm/DEG C.
From the viewpoint of reflow resistance, the curable resin composition of the second aspect preferably contains the epoxy resin and the phenolic hardener in an equivalent ratio of phenolic hydroxyl groups of the phenolic hardener to epoxy groups of the epoxy resin of 0.5 or more and less than 1.0.
The curable resin composition of the second embodiment may contain various materials and the method for producing the curable resin composition of the second embodiment are the same as those of the curable resin composition of the first embodiment, and therefore description thereof is omitted here.
[ use of curable resin composition ]
The applications of the curable resin composition of the first aspect and the curable resin composition of the second aspect are not particularly limited, and the curable resin composition of the first aspect can be used as a sealing material for electronic component devices, for example, in various mounting techniques. The curable resin composition is preferably used for various applications such as resin molded articles for various modules, resin molded articles for motors, resin molded articles for vehicles, and sealing materials for protective materials for electronic circuits, and is preferably excellent in fluidity and curability.
[ electronic parts device ]
The electronic component device of the present disclosure includes an element, and a cured resin of the curable resin composition of the first form or the curable resin composition of the second form that seals the element.
The electronic component device may include a support member on which the element is mounted.
As the support member, there may be mentioned: lead frames, carrier tapes after wiring, wiring boards, glass, silicon wafers, organic substrates, and the like. The support member is preferably a lead frame in terms of adhesion to a resin cured product of the curable resin composition.
The surface of the lead frame may be roughened or may not be roughened, and is preferably an unglazed lead frame from the viewpoint of manufacturing cost, and is preferably a roughened lead frame from the viewpoint of adhesion.
The roughening method is not particularly limited, and examples thereof include: alkali treatment, silane coupling treatment, sand cushion treatment, plasma treatment, corona discharge treatment, and the like.
The lead frame may include a plating layer including at least one of Au, pd, and Ni on at least a portion of the surface.
The plating layer may be a single layer or a plurality of layers. Examples of the multilayered plating layer include a plating layer having a three-layer structure in which a Ni-plated layer, a Pd-plated layer, and an Au-plated layer are laminated from the lead frame side.
Examples of the three-layer lead frame include a lead frame obtained by plating a copper lead frame called PPF (preplated lead frame (Pre Plating Lead Flame)) with ni—pd—au.
The thickness of the plating layer is not particularly limited, but is preferably 5 μm or less, more preferably 4 μm or less, and further preferably 3 μm or less.
Examples of the element included in the electronic component device include: active devices such as silicon chips, transistors, diodes, thyristors, etc.; passive elements such as capacitors, resistors, coils, etc.
The specific configuration of the electronic component device is as follows, but is not limited thereto.
(1) A general resin-sealed IC such as a DIP Package (Dual Inline Package, DIP), a plastic lead chip carrier (Plastic Leaded Chip Carrier, PLCC), a quad flat Package (Quad Flat Package, QFP), a Small Outline Package (Small Outline Package, SOP), a Small Outline J-lead Package (SOJ), a thin Small Outline Package (Thin Small Outline Package, TSOP), a thin quad flat Package (Thin Quad Flat Package, TQFP), etc., which has a structure in which a terminal portion and a lead portion of an element such as a bonding pad are fixed to a lead frame and are connected by wire bonding, bumps, etc., and then sealed with a curable resin composition;
(2) A tape carrier package (Tape Carrier Package, TCP) having a structure in which a component connected to a tape carrier by a bump is sealed with a curable resin composition;
(3) A Chip On Board (COB) module, a hybrid IC, a polycrystalline module, or the like, which has 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 curable resin composition;
(4) Ball Grid Array (BGA), chip scale package (Chip Size Package, CSP), multi-chip package (Multi Chip Package, MCP), system in package (System in a Package, siP), and the like have a structure in which an element is mounted on a surface of a support member having wiring board connection terminals formed on a back surface thereof, the element is connected to wiring formed on the support member by bump or wire bonding, and then the element is sealed by a curable resin composition.
The method of sealing the element using the curable resin composition is not particularly limited, and a known method can be applied. As the sealing method, for example, low pressure transfer molding is generally used, and injection molding, compression molding, casting, or the like may be used.
Examples (example)
Hereinafter, the present disclosure will be specifically described with reference to examples, but the present disclosure is not limited to these examples. Unless otherwise specified, the numerical values in the table refer to "parts by mass".
(examples 1 to 7 and comparative examples 1 to 3)
After premixing (dry blending) the materials of the formulations shown in Table 1, they were kneaded by a biaxial roll (roll surface temperature: about 80 ℃ C.) for about 15 minutes, cooled and pulverized to prepare powdery curable resin compositions.
Details of the materials in table 1 are as follows. The equivalent ratio of phenolic hydroxyl groups of the phenolic hardener to epoxy groups of the epoxy resin in table 1 was determined by the above method.
Epoxy resin a: the copolymer epoxy resin has the following structural units, an epoxy equivalent of 250g/eq, a melt viscosity of 0.7 dPa.s at 150 ℃ and Mn of 350-600
[ chemical 22]
Epoxy resin B: biphenyl type epoxy resin, epoxy equivalent 196g/eq, softening point 106 ℃, trade name "YX-4000H", mn 350 manufactured by Mitsubishi chemical Co., ltd
Epoxy resin C: biphenyl aralkyl epoxy resin and epoxy equivalent 284g/eq
Phenolic hardener a: aralkyl type phenol resin, hydroxyl equivalent 106g/eq
Phenolic hardener B: triphenylmethane type phenol resin and hydroxyl equivalent weight of 95g/eq
Phenolic hardener C: aralkyl type phenol resin, hydroxyl equivalent 203g/eq
Phenolic hardener D: melamine modified phenol resin, hydroxyl equivalent weight 120g/eq, softening point: 90 DEG C
Phenolic hardener E: triazine-type phenol resin, 2- [4- [ (2-hydroxy-3- (2' -ethyl) hexyl) oxy ] -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, basf (BASF) company, trade name "Di Nu Bin (Tinuvin) (registered trademark) 405"
Phenolic hardener F: novolak-type phenol resin and hydroxyl equivalent 223g/eq
Phenolic hardener G: novolak-type phenol resin and hydroxyl equivalent 156g/eq
Hardening accelerator: addition reaction product of triphenylphosphine and 1, 4-benzoquinone
Coupling agent A: 3-aminopropyl trimethoxysilane
Coupling agent B: 3-glycidoxypropyl trimethoxysilane
Coupling agent C: linear polysiloxane, melting point: at the temperature of-70 ℃, the epoxy equivalent weight is 120g/eq to 150g/eq
Coupler D: tetrathioether di-triethoxysilane
Stress-relieving agent A: epoxy modified silicone resin
Stress-relieving agent B: indene-containing copolymers
Stress-relieving agent C: phenyl-containing silicone resin
Inorganic filler a: silica filler having an average particle diameter of 19.4. Mu.m
Inorganic filler B: silica filler having an average particle diameter of 0.6 μm
Inorganic filler C: silica filler having average particle diameter of 50nm or less
Inorganic filler D: magnesium and zinc-containing metal hydroxide having an average particle diameter of 1.2 μm
Evaluation of curable resin composition
The properties of the curable resin compositions produced in examples and comparative examples were evaluated by the following property tests. The evaluation results are shown in table 1.
The production of the cured resin product using the curable resin composition is performed as follows unless explicitly stated otherwise: after molding with a transfer molding machine at a mold temperature of 175℃and a molding pressure of 8.3MPa for 120 seconds, post-curing was performed at 175℃for 5 hours.
< evaluation of reflow resistance >
A28-pin Small Outline (SO) package (lead frame material: copper alloy, ni-Pd-Au plating processed product) having a die pad of 5.2mm.times.4.1 mm mounted with a silicon chip of 3.2mm.times.2 mm.times.0.37 mm was molded using a curable resin composition, and then post-cured at 175 ℃ for 5 hours.
The obtained molded article was visually confirmed to have no external cracks, and was confirmed to have no internal peeling by an ultrasonic flaw detector (FS-200 manufactured by hitachi corporation). The molded article was dried at 125℃for 12 hours, and then humidified at a temperature of 85℃and a relative humidity of 85% for 168 hours.
Then, according to the specification of JEDEC, the temperature condition was set to 260 ℃, reflow treatment was performed 3 times at the same temperature, and the presence or absence of cracks on the outside of the package was visually observed, and the presence or absence of peeling in the inside of the package was observed by an ultrasonic flaw detector. Reflow resistance was evaluated as a ratio of the number of packages in which any of cracking and peeling occurred to the number of packages tested. The evaluation results are summarized in Table 1.
(evaluation criterion)
A: crack and peeling were generated at 0%
B: crack and peeling generation exceeding 0% and less than 60%
C: crack and peeling are generated at 60% or more and less than 100%
D: crack and peel generation was 100%
< determination of tan. Delta. And storage modulus of elasticity >
Based on the above conditions, resin cured products of the curable resin compositions obtained in the examples and comparative examples were produced. The resin cured product was a rectangular resin cured product having a short side of 5mm, a long side of 50mm, and a thickness of 2 mm.
For the resin cured product, in test mode: 3 point bending mode, measurement temperature: 25-330 ℃, and the temperature rising speed is as follows: 10 ℃/min, test frequency: dynamic viscoelasticity was measured at 1Hz, and values of storage viscoelasticity were obtained from the obtained graphs (vertical axis: tan. Delta. And horizontal axis: temperature) and are summarized in Table 1.
The table is summarized by obtaining (1) a temperature at which tan δ is maximum (glass transition temperature), (2) a tan δ value at the glass transition temperature, (3) a total of tan δ values at respective temperatures of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ (in table 1, it is described as tan δ total 220 ℃ to 250 ℃), (4) a total of tan δ values at respective temperatures of 70 ℃, 80 ℃ and 90 ℃ (in table 1, it is described as tan δ total 70 ℃ to 90 ℃), and (5) a tan δ value at a temperature 10 degrees lower than the glass transition temperature (in table 1, it is described as tan δ ratio) when tan δ value at the glass transition temperature is 100.
< measurement of coefficient of thermal expansion (CTE 1)
Based on the above conditions, resin cured products of the curable resin compositions obtained in the examples and comparative examples were produced. The resin cured product is set asIs a cured resin product of (a).
Then, based on JIS K7197: 2012, and the inclination ratio of the strain of the cured resin with respect to the tangent line when the temperature is plotted is determined by a thermo-mechanical analysis method in a range of 10 to 30 ℃. The measurement results are summarized in Table 1.
The test load was reset to 15g, and the temperature rise rate was set to 5℃per minute.
Further, a TMA high-precision two-sample thermal analyzer (device name SS 6100) manufactured by fine instruments (Seiko Instruments) corporation was used for the measurement of the linear expansion coefficient.
< measurement of Water absorption >
Based on the above conditions, resin cured products of the curable resin compositions obtained in the examples and comparative examples were produced. The resin cured product was a rectangular cured product having a short side of 5.1mm, a long side of 20mm, and a thickness of 2 mm.
Then, the resin cured product was allowed to stand at a temperature of 85℃and a relative humidity of 85% for 168 hours.
The mass (g) of the resin hardening agent after standing was measured, and the increase rate (%) relative to the mass (g) of the resin hardening agent before standing was obtained. The results are summarized in Table 1.
< flowability evaluation (spiral flow) >
The curable resin compositions obtained in examples and comparative examples were molded using a mold for spiral flow measurement according to EMMI-1-66 under conditions of a mold temperature of 180 ℃, a molding pressure of 6.9MPa and a curing time of 90 seconds, and a flow distance (cm) was obtained. The measurement results are summarized in Table 1.
TABLE 1
From the results summarized in Table 1, it can be seen that: the curable resin composition obtained in examples was excellent in reflow resistance as compared with the curable resin composition obtained in comparative examples.
The entire disclosure of japanese patent application No. 2021-140407, filed on 8/30 of 2021, is incorporated herein by reference. All documents, patent applications, and technical specifications described in this specification are incorporated by reference into this specification to the same extent as if each document, patent application, and technical specification were specifically and individually indicated to be incorporated by reference.
Claims (7)
1. In a graph obtained by measuring dynamic viscoelasticity of a resin cured product of a curable resin composition, the graph has a vertical axis of tan delta and a horizontal axis of temperature of 30-260 ℃, wherein (1) the temperature at which tan delta is maximum is less than 120 ℃, and (2) the maximum value of tan delta exceeds 0.400, and (3) the total of tan delta values at each temperature of 220 ℃, 230 ℃, 240 ℃ and 250 ℃ exceeds 0.400.
2. In a graph in which the vertical axis is tan delta and the horizontal axis is 30 to 260 ℃ obtained by measuring dynamic viscoelasticity of a resin cured product of the curable resin composition, the total tan delta value at each temperature of 70 ℃, 80 ℃ and 90 ℃ exceeds 0.600.
3. The curable resin composition according to claim 1 or 2, wherein when the maximum value of tan δ in the graph is set to 100, the tan δ value exceeds 60 at least at any one of temperatures at which tan δ becomes maximum and at-10 ℃.
4. The curable resin composition according to any one of claims 1 to 3, wherein the storage viscoelasticity at 260℃obtained by dynamic viscoelasticity measurement of a resin cured product of the curable resin composition is 450MPa or less.
5. The curable resin composition according to any one of claims 1 to 4, wherein the epoxy resin and the phenolic hardener are contained in an equivalent ratio of phenolic hydroxyl groups of the phenolic hardener to epoxy groups of the epoxy resin of 0.5 or more and less than 1.0.
6. An electronic component device comprising an element and a resin cured product of the curable resin composition according to any one of claims 1 to 5 sealing the element.
7. The electronic component device according to claim 6, further comprising a support member on one of which the element is mounted.
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JP2021-140407 | 2021-08-30 | ||
PCT/JP2022/032271 WO2023032860A1 (en) | 2021-08-30 | 2022-08-26 | Curable resin composition and electronic component device |
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JPH06200121A (en) * | 1993-01-06 | 1994-07-19 | Nippon Steel Chem Co Ltd | Low-pressure transfer molding material for sealing semiconductor |
KR101557538B1 (en) * | 2012-12-24 | 2015-10-06 | 제일모직주식회사 | Epoxy resin composition for encapsulating semiconductor device and semiconductor device encapsulated by using the same |
KR101557537B1 (en) * | 2012-12-24 | 2015-10-06 | 제일모직주식회사 | Epoxy resin composition for encapsulating semiconductor device and semiconductor device encapsulated by using the same |
SG11202012017VA (en) * | 2018-06-12 | 2021-01-28 | Showa Denko Materials Co Ltd | Curable resin composition and electronic component device |
JP7322368B2 (en) * | 2018-09-14 | 2023-08-08 | 株式会社レゾナック | Curable resin composition and electronic component device |
JP7484081B2 (en) * | 2018-10-18 | 2024-05-16 | 株式会社レゾナック | Curable resin composition and electronic component device |
JP7269579B2 (en) * | 2018-10-19 | 2023-05-09 | 株式会社レゾナック | Epoxy resin composition and electronic component device |
JPWO2021075207A1 (en) * | 2019-10-16 | 2021-04-22 |
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