CN113195585A - Curable resin composition and electronic component device - Google Patents
Curable resin composition and electronic component device Download PDFInfo
- Publication number
- CN113195585A CN113195585A CN202080007052.5A CN202080007052A CN113195585A CN 113195585 A CN113195585 A CN 113195585A CN 202080007052 A CN202080007052 A CN 202080007052A CN 113195585 A CN113195585 A CN 113195585A
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- CN
- China
- Prior art keywords
- group
- bonded
- resin composition
- curable resin
- epoxy resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 87
- 239000003822 epoxy resin Substances 0.000 claims abstract description 140
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 139
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 73
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- -1 phenol compound Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 26
- 239000004305 biphenyl Substances 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 13
- 238000007789 sealing Methods 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003566 sealing material Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 description 45
- 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 35
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
- 239000011256 inorganic filler Substances 0.000 description 26
- 229910003475 inorganic filler Inorganic materials 0.000 description 26
- 125000000962 organic group Chemical group 0.000 description 25
- 239000002245 particle Substances 0.000 description 24
- 150000002989 phenols Chemical class 0.000 description 19
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000004848 polyfunctional curative Substances 0.000 description 15
- 229920003986 novolac Polymers 0.000 description 14
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 12
- 239000007822 coupling agent Substances 0.000 description 11
- 239000003063 flame retardant Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 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 10
- 239000004593 Epoxy Substances 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 239000000470 constituent Substances 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001721 transfer moulding Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical class [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- UIXPTCZPFCVOQF-UHFFFAOYSA-N ubiquinone-0 Chemical compound COC1=C(OC)C(=O)C(C)=CC1=O UIXPTCZPFCVOQF-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 2
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- XGINAUQXFXVBND-UHFFFAOYSA-N 1,2,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrimidine Chemical compound N1CC=CN2CCCC21 XGINAUQXFXVBND-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- QKUSYGZVIAWWPY-UHFFFAOYSA-N 1,3-dioxane;7-oxabicyclo[4.1.0]heptane Chemical compound C1COCOC1.C1CCCC2OC21 QKUSYGZVIAWWPY-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 1
- PJEKFSKIOOHJNR-UHFFFAOYSA-N 1h-indene;styrene Chemical compound C=CC1=CC=CC=C1.C1=CC=C2CC=CC2=C1 PJEKFSKIOOHJNR-UHFFFAOYSA-N 0.000 description 1
- ZEGDFCCYTFPECB-UHFFFAOYSA-N 2,3-dimethoxy-1,4-benzoquinone Natural products C1=CC=C2C(=O)C(OC)=C(OC)C(=O)C2=C1 ZEGDFCCYTFPECB-UHFFFAOYSA-N 0.000 description 1
- BLBVJHVRECUXKP-UHFFFAOYSA-N 2,3-dimethoxy-1,4-dimethylbenzene Chemical group COC1=C(C)C=CC(C)=C1OC BLBVJHVRECUXKP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MSJIPWGDQODKSK-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)phenyl]phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)O)C=C1 MSJIPWGDQODKSK-UHFFFAOYSA-N 0.000 description 1
- HRSLYNJTMYIRHM-UHFFFAOYSA-N 2-[[4-[3,5-dimethyl-4-(oxiran-2-ylmethoxy)phenyl]-2,6-dimethylphenoxy]methyl]oxirane Chemical group CC1=CC(C=2C=C(C)C(OCC3OC3)=C(C)C=2)=CC(C)=C1OCC1CO1 HRSLYNJTMYIRHM-UHFFFAOYSA-N 0.000 description 1
- OZRVXYJWUUMVOW-UHFFFAOYSA-N 2-[[4-[4-(oxiran-2-ylmethoxy)phenyl]phenoxy]methyl]oxirane Chemical group C1OC1COC(C=C1)=CC=C1C(C=C1)=CC=C1OCC1CO1 OZRVXYJWUUMVOW-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-O 2-ethyl-5-methyl-1h-imidazol-3-ium Chemical compound CCC=1NC(C)=C[NH+]=1 ULKLGIFJWFIQFF-UHFFFAOYSA-O 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-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
- 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
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052839 forsterite Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- NPEWZDADCAZMNF-UHFFFAOYSA-N gold iron Chemical compound [Fe].[Au] NPEWZDADCAZMNF-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 150000002460 imidazoles Chemical class 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
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- XMFOQHDPRMAJNU-UHFFFAOYSA-N lead(ii,iv) oxide Chemical compound O1[Pb]O[Pb]11O[Pb]O1 XMFOQHDPRMAJNU-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052863 mullite Inorganic materials 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 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
- 150000004965 peroxy acids Chemical class 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000010287 polarization Effects 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
- 229920000642 polymer 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
- 230000001737 promoting effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 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
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910000679 solder Inorganic materials 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
- ZRIUSVITVGWLSQ-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC1=CC=CC=C1 ZRIUSVITVGWLSQ-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 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
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052845 zircon 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
- C08G59/44—Amides
- C08G59/46—Amides together with other curing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
A curable resin composition comprising an epoxy resin and a curing agent, wherein the epoxy resin comprises an epoxy group-containing epoxy resin having an epoxy group bonded to an aromatic ring to which an electron-donating group is not bonded, and the curing agent comprises a curing agent having a hydroxyl group bonded to an aromatic ring to which an electron-donating group is bonded.
Description
Technical Field
The present invention relates to a curable resin composition and an electronic component device.
Background
With the miniaturization, weight reduction, and performance enhancement of electronic devices, the density of mounting has been increasing. Accordingly, the mainstream of the electronic component device is changed from the conventional pin insertion type package to the surface mounting type package such as an Integrated Circuit (IC) or a Large Scale Integrated Circuit (LSI). Further, diversification of sealing technologies such as System in a Package (SiP) and disposable sealing has been advanced (for example, see patent document 1).
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2018-107416
Disclosure of Invention
Problems to be solved by the invention
As sealing techniques have been diversified, components mounted on chips have been diversified, and depending on the type of component (sensor, inductor, or the like), the component is expected to be affected by heat generated when the sealing material is cured. Therefore, it is desirable to reduce the heating temperature for hardening the sealing material.
In view of the above circumstances, an object of the present invention is to provide a curable resin composition having excellent curability at low temperatures, and an electronic component device obtained using the same.
Means for solving the problems
Means for solving the above problems include the following embodiments.
< 1 > a curable resin composition comprising an epoxy resin and a curing agent, the epoxy resin comprising an epoxy group-containing epoxy resin having an epoxy group bonded to an aromatic ring to which an electron-donating group is not bonded, the curing agent comprising a curing agent having a hydroxyl group bonded to an aromatic ring to which an electron-donating group is bonded.
< 2 > the curable resin composition of < 1 >, wherein the electron-donating group is at least one selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an amino group and a methoxy group.
< 3 > the curable resin composition according to < 1 > or < 2 >, wherein the epoxy group-containing epoxy resin bonded to the aromatic ring to which an electron-donating group is not bonded has a biphenyl structure.
< 4 > the curable resin composition according to any one of < 1 > to < 3 >, wherein the curing agent having a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded has a structure obtained by novolak-converting a phenol compound to which the electron-donating group is bonded.
< 5 > the curable resin composition according to any one of < 1 > to < 4 >, wherein the curing agent having a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded has a structure obtained by novolak-converting a phenol compound to which the electron-donating group is bonded at an ortho position.
< 6 > the curable resin composition according to any one of < 1 > to < 5 >, further comprising an imidazole compound.
< 7 > the curable resin composition according to any one of < 1 > to < 6 > for use as a sealing material for electronic component devices.
< 8 > an electronic parts device comprising: an element; and a cured product of the curable resin composition according to any one of < 1 > -7 > sealing the element.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a curable resin composition having excellent curability at low temperatures and an electronic component device obtained using the same are provided.
Detailed Description
Hereinafter, a mode for carrying out the present invention will be described in detail. However, the present invention is not limited to the following embodiments. In the following embodiments, the constituent elements (including element steps) are not necessarily required unless otherwise explicitly indicated. The same is true for numerical values and ranges thereof, and the invention is not limited thereto.
In the present invention, the term "step" includes a step other than a step independent from other steps, as long as the purpose of the step is achieved, even when the step cannot be clearly distinguished from other steps.
In the present invention, numerical values before and after the "to" are included in the numerical range indicated by the "to" are used as the minimum value and the maximum value, respectively.
In the numerical ranges recited in the present invention, the upper limit or the lower limit recited in one numerical range may be replaced with the upper limit or the lower limit recited in another numerical range recited in a stepwise manner. In the numerical ranges, the upper limit or the lower limit of the numerical range may be replaced with the values shown in the examples.
In the present invention, the content or content of each component in the composition refers to the total content or content of a plurality of substances present in the composition, unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition.
In the present invention, the particle diameters of the respective components in the composition indicate values regarding a mixture of a plurality of types of particles present in the composition, unless otherwise specified, when a plurality of types of particles corresponding to the respective components are present in the composition.
< curable resin composition >
The curable resin composition of the present invention is a curable resin composition containing an epoxy resin and a curing agent, the epoxy resin containing an epoxy group-containing epoxy resin (hereinafter, also referred to as a specific epoxy resin) having an epoxy group bonded to an aromatic ring to which an electron-donating group is not bonded, the curing agent containing a curing agent having a hydroxyl group bonded to an aromatic ring to which an electron-donating group is bonded (hereinafter, also referred to as a specific curing agent).
The curable resin composition having the above-described structure has excellent curability at low temperatures (for example, 150 ℃ or lower). The reason for this is not necessarily clear, but it is considered that by reacting an epoxy group-containing group bonded to an aromatic ring to which an electron-donating group is not bonded with a hydroxyl group bonded to an aromatic ring to which an electron-donating group is bonded, the reactivity of the epoxy resin with the curing agent is improved, and the curing at low temperature is promoted.
The curable resin composition of the present invention has excellent curability at low temperatures as compared with conventional curable resin compositions, and is therefore useful, for example, as a sealing material for electronic component devices including components having poor heat resistance. Further, the effects of suppressing thermal shrinkage during curing and reducing warpage of the substrate can be expected.
In the present invention, the "electron-donating group" refers to a substituent having a property of increasing the activity of an aromatic ring bonded thereto, and the kind thereof is not particularly limited. Examples thereof include alkyl groups having 1 to 6 carbon atoms, amino groups, and methoxy groups.
In the present invention, an epoxy group-containing or hydroxyl group-containing group is not included in the "electron-donating group". When the epoxy resin or the curing agent is a polymer, the substituent does not include a structure corresponding to the main chain.
In the present invention, the "epoxy group-containing" refers to a substituent containing an epoxy group (oxirane structure). Specifically, the epoxy group is directly bonded to the aromatic ring, and the epoxy group is bonded to the aromatic ring via a hydrocarbon group having 1 to 3 carbon atoms (preferably a methylene group), a hydrocarbyloxy group having 1 to 3 carbon atoms (preferably a methyleneoxy group), or a hydrocarbylamino group having 1 to 3 carbon atoms.
In the present invention, the "aromatic ring having an epoxy group bonded thereto" includes a benzene ring and a condensed ring (e.g., naphthalene) having two or more benzene rings. In the case of a structure in which two or more benzene rings are linked by a single bond or the like (biphenyl structure or the like), a benzene ring directly bonded with an epoxy group is used as a structure in which an aromatic ring containing an epoxy group is bonded.
(epoxy resin)
The epoxy resin contained in the curable resin composition is not particularly limited as long as it contains a specific epoxy resin, and can be selected according to the desired characteristics of the curable resin composition.
The specific epoxy resin may have only an epoxy group containing group bonded to an aromatic ring to which an electron-donating group is not bonded as an epoxy group, or may have an epoxy group containing group bonded to an aromatic ring to which an electron-donating group is not bonded and an epoxy group containing group bonded to an aromatic ring to which an electron-donating group is bonded.
From the viewpoint of curability at low temperatures, the proportion of the specific epoxy resin in the epoxy resin is preferably 20% by mass or more, and more preferably 30% by mass or more of the entire epoxy resin. The upper limit of the proportion of the specific epoxy resin in the epoxy resin is not particularly limited. From the viewpoint of the balance of the properties of the cured product, the proportion of the specific epoxy resin in the epoxy resin may be 90 mass% or less, or may be 80 mass% or less of the entire epoxy resin.
From the viewpoint of reactivity at low temperatures, the specific epoxy resin preferably has a structure in which two aromatic rings are bonded by a single bond or a divalent linking group, more preferably has a structure in which two aromatic rings are bonded by a single bond or a divalent linking group (biphenyl structure), and as the biphenyl structure, it is more preferably has a structure represented by the following general formula (a). The specific epoxy resin having a biphenyl structure may further have a structure other than a biphenyl structure (e.g., a triphenylmethane structure).
[ solution 1]
In the general formula (a), at least one of the two represents a bonding site to an adjacent atom.
Specific examples of the epoxy resin include: a novolak-type epoxy resin (e.g., a phenol novolak-type epoxy resin, an o-cresol novolak-type epoxy resin, etc.) obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol a, and bisphenol F, and naphthol compounds such as α -naphthol, β -naphthol, and dihydroxynaphthalene, with an aliphatic aldehyde compound such as formaldehyde, acetaldehyde, and propionaldehyde under an acidic catalyst to obtain a novolak resin, and epoxidizing the novolak resin; a triphenylmethane type epoxy resin obtained by subjecting the phenolic compound and an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde to condensation or co-condensation in the presence of an acidic catalyst to obtain a triphenylmethane type phenol resin and epoxidizing the triphenylmethane type phenol resin; a co-polymerization type 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 novolac resin and epoxidizing the novolac resin; diphenylmethane-type epoxy resins as diglycidyl ethers of bisphenol a, bisphenol F, and the like; biphenyl type epoxy resins as diglycidyl ethers of alkyl-substituted or unsubstituted biphenols; a stilbene type epoxy resin as a diglycidyl ether of a stilbene (stilbene) type phenol compound; an epoxy resin containing a sulfur atom as a diglycidyl ether of bisphenol S or the like; epoxy resins as glycidyl ethers of alcohols such as butanediol, polyethylene glycol, and polypropylene glycol; glycidyl ester type epoxy resins as glycidyl esters of polycarboxylic acid compounds such as phthalic acid, isophthalic acid, and tetrahydrophthalic acid; glycidyl amine type epoxy resins obtained by replacing active hydrogen bonded to a nitrogen atom such as aniline, diaminodiphenylmethane, and isocyanuric acid with a glycidyl group; a dicyclopentadiene type epoxy resin obtained by epoxidizing a co-condensation resin of dicyclopentadiene and a phenol compound; alicyclic epoxy resins such as vinylcyclohexene dioxide diepoxide, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, and 2- (3, 4-epoxy) cyclohexyl-5, 5-spiro (3, 4-epoxy) cyclohexane-m-dioxane obtained by epoxidizing an olefin bond in the molecule; a p-xylene-modified epoxy resin as a glycidyl ether of the p-xylene-modified phenol resin; a m-xylene-modified epoxy resin which is a glycidyl ether of a m-xylene-modified phenol resin; terpene-modified epoxy resins as glycidyl ethers of terpene-modified phenol resins; a dicyclopentadiene-modified epoxy resin which is a glycidyl ether of a dicyclopentadiene-modified phenol resin; a cyclopentadiene-modified epoxy resin which is a glycidyl ether of a cyclopentadiene-modified phenol resin; a polycyclic aromatic ring-modified epoxy resin which is a glycidyl ether of the polycyclic aromatic ring-modified phenol resin; naphthalene type epoxy resins as glycidyl ethers of phenol resins containing naphthalene rings; halogenated phenol novolac type epoxy resins; p-phenylene bisphenol type epoxy resin; trimethylolpropane type epoxy resins; linear aliphatic epoxy resins obtained by oxidizing an olefin bond with a peracid 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, epoxy resins such as epoxy of silicone resin and epoxy of acrylic resin may be mentioned. These epoxy resins may be used alone or in combination of two or more.
From the viewpoint of balance between reflow resistance and fluidity, the epoxy resin is preferably an epoxy resin selected from the group consisting of biphenyl type epoxy resins, stilbene type epoxy resins, diphenylmethane type epoxy resins, sulfur atom containing type epoxy resins, novolac type epoxy resins, dicyclopentadiene type epoxy resins, triphenylmethane type epoxy resins, copolymerized type epoxy resins, and aralkyl type epoxy resins.
Specific examples of the biphenyl type epoxy resin include epoxy resins represented by the following general formula (II). In the epoxy resin represented by the following general formula (II), R8The 3,3',5,5' positions of the 4-and 4' -positions of the oxygen atom are methyl and the other R is8YX-4000H (trade name, Mitsubishi chemical corporation) which is a hydrogen atom, all of R84,4' -bis (2, 3-epoxypropoxy) biphenyl being a hydrogen atom, all R8In the case of a hydrogen atom and R8The 3,3',5,5' positions of the 4-and 4' -positions of the oxygen atom are methyl and the other R is8A mixed product in the case of a hydrogen atom, i.e., YL-6121H (trade name) or the like is available as a commercially available product.
[ solution 2]
In the formula (II), R8Each of which represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aromatic group having 4 to 18 carbon atoms (in the case of a specific epoxy resin, a hydrogen atom is preferable), and may be the same or different. n is an average value and represents a number of 0 to 10.
Specific examples of the stilbene type epoxy resin include epoxy resins represented by the following general formula (III).
[ solution 3]
In the formula (III), R9And R10The monovalent organic groups each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms (in the case of a specific epoxy resin, a hydrogen atom is preferable), and may be the same or different. n is an average value and represents a number of 0 to 10.
Specific examples of the diphenylmethane epoxy resin include epoxy resins represented by the following general formula (IV). In the epoxy resin represented by the following general formula (IV), R11Are each a hydrogen atom, R12The 3,3',5,5' positions of the 4-and 4' -positions of the oxygen atom are methyl and the other R is12YSLV-80XY (trade name, Nissian iron goddess chemical Co., Ltd.) or the like, which is a hydrogen atom, is available as a commercially available product.
[ solution 4]
In the formula (IV), R11R represents a hydrogen atom or a C1-18 monovalent organic group12The monovalent organic groups each represent a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms (in the case of a specific epoxy resin, a hydrogen atom is preferable), and may be the same or different. n is an average value and represents a number of 0 to 10.
Specific examples of the sulfur atom-containing epoxy resin include epoxy resins represented by the following general formula (V). In the epoxy resin represented by the following general formula (V), R13When the positions substituted by the oxygen atom are 4-position and 4' -position, the 3,3' -position is t-butyl, the 6,6' -position is methyl and the other R is13YSLV-120TE (trade name, Nippon iron-god chemical Co., Ltd.) or the like, which is a hydrogen atom, is available as a commercially available product.
[ solution 5]
In the formula (V), R13Represents a hydrogen atom or a carbon number1 to 18 monovalent organic groups (preferably hydrogen atoms in the case of a specific epoxy resin) may be the same or different. n is an average value and represents a number of 0 to 10.
Specific examples of the novolak type epoxy resin include epoxy resins represented by the following general formula (VI). In the epoxy resin represented by the following general formula (VI), R14All being hydrogen atoms, R15ESCN-190, ESCN-195 (sumitomo chemical corporation, trade name) which is methyl, i ═ 1; r14N-770, N-775 (trade name, dear-son (DIC) gmbh) all of which is a hydrogen atom, i ═ 0; having R14Moieties wherein all are hydrogen atoms, i-0, with i-1, R15is-CH (CH)3) -a styrene-modified phenol novolac type epoxy resin of Ph part, namely, YDAN-1000-10C (trade name, product name, yokuwa chemical corporation); having R14All being hydrogen atoms, i ═ 1, R15Moieties being methyl with i ═ 2, R15A benzyl-modified cresol novolak type epoxy resin in which one is a methyl group and one is a benzyl group, that is, HP-5600 (trade name, dear-son (DIC) corporation), and the like are available as commercially available products.
[ solution 6]
In the formula (VI), R14The hydrogen atom or monovalent organic group (preferably hydrogen atom) having 1 to 18 carbon atoms may be the same or different. R15The monovalent organic groups have 1 to 18 carbon atoms and may be the same or different. Each i independently represents an integer of 0 to 3 (preferably 0 in the case of a specific epoxy resin). n is an average value and represents a number of 0 to 10.
Specific examples of the dicyclopentadiene type epoxy resin include epoxy resins represented by the following general formula (VII). Among epoxy resins represented by the following general formula (VII), HP-7200 (trade name, Dean (DIC) corporation) having i ═ 0 is available as a commercially available product.
[ solution 7]
In the formula (VII), R16The monovalent organic groups have 1 to 18 carbon atoms and may be the same or different. Each i independently represents an integer of 0 to 3 (preferably 0 in the case of a specific epoxy resin). n is an average value and represents a number of 0 to 10.
Specific examples of the triphenylmethane type epoxy resin include epoxy resins represented by the following general formula (VIII). Among the epoxy resins represented by the following general formula (VIII), 1032H60 (trade name, Mitsubishi chemical corporation), EPPN-502H (trade name, Nippon chemical corporation) and the like, in which i is 0 and k is 0, are available as commercially available products.
[ solution 8]
In the formula (VIII), R17And R18The monovalent organic groups have 1 to 18 carbon atoms and may be the same or different. i independently represent an integer of 0 to 3 (preferably 0 in the case of a specific epoxy resin), and k independently represent an integer of 0 to 4 (preferably 0 in the case of a specific epoxy resin). n is an average value and represents a number of 0 to 10.
Specific examples of the co-polymerization type epoxy resin obtained by epoxidizing a novolac resin obtained from a naphthol compound, a phenol compound and an aldehyde compound include epoxy resins represented by the following general formula (IX). In the epoxy resin represented by the following general formula (IX), R21NC-7300 (trade name, Nippon chemical Co., Ltd.) or the like, which is a methyl group, i is 1, j is 0, and k is 0, is available as a commercially available product.
[ solution 9]
In the formula (IX), R19～R21The monovalent organic groups have 1 to 18 carbon atoms and may be the same or different. i independently represents an integer of 0 to 3 (preferably 0 in the case of a specific epoxy resin), j independently represents an integer of 0 to 2 (preferably 0 in the case of a specific epoxy resin), and k independently represents an integer of 0 to 4 (preferably 0 in the case of a specific epoxy resin). l and m are each an average value and are a number of 0 to 10, and (l + m) represents a number of 0 to 10. The epoxy resin represented by the formula (IX) has a terminal of either the following formula (IX-1) or formula (IX-2). In the formulae (IX-1) and (IX-2), R19～R21The definitions of i, j and k in (A) and R in formula (IX)19～R21I, j and k in (1) are as defined. n is 1 (in the case of bonding via methylene) or 0 (in the case of bonding without methylene).
[ solution 10]
Examples of the epoxy resin represented by the general formula (IX) include: a random copolymer randomly including 1 constituent unit and m constituent units, an alternating copolymer alternately including 1 constituent unit and m constituent units, a copolymer regularly including 1 constituent unit and m constituent units, a block copolymer including 1 constituent unit and m constituent units in a block form, and the like. Any of these may be used alone, or two or more of these may be used in combination.
Specific examples of the aralkyl type epoxy resin include epoxy resins represented by the following general formula (X) and general formula (XI). In the epoxy resin represented by the following general formula (X), i is 0 and R38NC-3000L (trade name, japan chemical corporation, ltd.) as a hydrogen atom in a mass ratio of 80: 20 i is 0 and R38Epoxy resins being hydrogen atoms with all R of the formula (II)8CER-3000 (trade name, manufactured by Nippon chemical Co., Ltd.) and the like, which is a mixture of epoxy resins that are hydrogen atoms, are available as commercially available products. In addition, the following general formula (X)I) Among the epoxy resins shown in the above, ESN-175 (trade name, Nissian iron-gold chemical Co., Ltd.) in which i is 0, j is 0, and k is 0, and the like are commercially available.
[ solution 11]
In the formulae (X) and (XI), R38The monovalent organic groups may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms. R37、R39～R41The monovalent organic groups have 1 to 18 carbon atoms and may be the same or different. i is independently an integer of 0 to 3 (preferably 0 in the case of a specific epoxy resin), j is independently an integer of 0 to 2 (preferably 0 in the case of a specific epoxy resin), k is independently an integer of 0 to 4 (preferably 0 in the case of a specific epoxy resin), and l is independently an integer of 0 to 6 (preferably 0 in the case of a specific epoxy resin). n is an average value and is a number of 0 to 10 independently.
With respect to R in the general formulae (II) to (XI)8～R21And R37～R41By "may be respectively the same or different" is meant for example 8 to 88R's in formula (II)8May be the same or different. With respect to the other R9～R21And R37～R41It means that the numbers of the compounds contained in the formulae may be the same or different. In addition, R8～R21And R37～R41May be the same or different. For example, R9And R10May be the same or different.
The 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 preferably ranges from 0 to 10 independently. When n is 10 or less, the melt viscosity of the resin component is not excessively high, the viscosity of the curable resin composition is reduced during melt molding, and the occurrence of filling failure, deformation of bonding wires (metal wires connecting the element and the lead), and the like tends to be suppressed. More preferably, n is set in the range of 0 to 4.
The epoxy equivalent of the epoxy resin is not particularly limited. The epoxy equivalent of the epoxy resin is preferably 100 to 1000g/eq, more preferably 150 to 500g/eq, from the viewpoint of a balance among various properties such as moldability, reflow resistance, and electrical reliability.
In the case where the epoxy resin is a solid, the softening point or the melting point thereof is not particularly limited. From the viewpoint of workability in the preparation of the curable resin composition, it is preferably from 50 ℃ to 130 ℃.
The melting point of the epoxy resin was measured by Differential Scanning Calorimetry (DSC), and the softening point of the epoxy resin was measured by a method (ring and ball method) based on Japanese Industrial Standards (JIS) K7234: 1986.
The content of the epoxy resin in the curable resin composition is preferably 0.5 to 50% by mass, and more preferably 2 to 30% by mass, from the viewpoint of strength, fluidity, heat resistance, moldability, and the like.
(hardening agent)
The curing agent contained in the curable resin composition is not particularly limited as long as it contains a specific curing agent, and it can be selected according to the desired characteristics of the curable resin composition.
The specific curing agent may have only a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded as a hydroxyl group, or may have a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded and a hydroxyl group bonded to the aromatic ring to which the electron-donating group is not bonded.
From the viewpoint of curing properties at low temperatures, the proportion of the specific curing agent in the curing agent is preferably 20% by mass or more, and more preferably 30% by mass or more, of the entire curing agent. The upper limit of the proportion of the specific hardener in the hardener is not particularly limited. From the viewpoint of the balance of the properties of the cured product, the proportion of the specific curing agent in the curing agent may be 90 mass% or less, or may be 80 mass% or less of the entire curing agent.
From the viewpoint of low-temperature rapid curing, the specific curing agent preferably has a structure obtained by novolak-converting a phenol compound to which an electron-donating group is bonded, and preferably has a structure obtained by novolak-converting a phenol compound to which an electron-donating group is bonded at an ortho position. The phenol compound having an electron-donating group bonded to an ortho position is novolak-formed, and examples thereof include those represented by the following general formula (B).
[ solution 12]
In the general formula (B), R1Each independently represents an electron-donating group, and n represents an integer of 0 to 10. In the general formula (B), R1Each independently preferably an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and more preferably a methyl group (having an o-cresol novolac structure).
As the curing agent, specifically, there can be mentioned: phenolic hardeners, amine hardeners, anhydride hardeners, polythiol hardeners, polyaminoamide hardeners, isocyanate hardeners, blocked isocyanate hardeners, and the like. From the viewpoint of both curability and pot life, at least one selected from the group consisting of a phenol curing agent, an amine curing agent, and an acid anhydride curing agent is preferable, and from the viewpoint of electrical reliability, a phenol curing agent is more preferable.
Examples of the phenol curing agent include a phenol resin and a polyphenol compound having two or more phenolic hydroxyl groups in 1 molecule. Specifically, there may be mentioned: polyhydric phenol compounds such as resorcinol, catechol, bisphenol a, bisphenol F, and substituted or unsubstituted biphenol; a novolak-type phenol resin obtained by condensing or co-condensing at least one phenolic compound selected from the group consisting of phenol compounds such as phenol, cresol, xylenol, resorcinol, catechol, bisphenol a, bisphenol F, phenylphenol, and aminophenol, and naphthol compounds such as α -naphthol, β -naphthol, and dihydroxynaphthalene, with aldehyde compounds such as formaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, and salicylaldehyde, under an acidic catalyst; aralkyl phenol resins such as phenol aralkyl resins and naphthol aralkyl resins synthesized from the above phenolic compounds and dimethoxyp-xylene, bis (methoxymethyl) biphenyl and the like; p-xylene and/or m-xylene modified phenol resins; a melamine-modified phenol resin; terpene-modified phenol resin; dicyclopentadiene type phenol resins and dicyclopentadiene type naphthol resins synthesized by copolymerization of the phenolic compounds with dicyclopentadiene; a cyclopentadiene-modified phenol resin; polycyclic aromatic ring-modified phenol resins; a biphenyl type phenol resin; a triphenylmethane type phenol resin obtained by condensing or co-condensing the phenolic compound with an aromatic aldehyde compound such as benzaldehyde or salicylaldehyde under an acidic catalyst; phenol resins obtained by copolymerizing two or more of these. These phenol hardeners may be used alone or in combination of two or more.
Among the phenol curing agents, from the viewpoint of reflow resistance, at least one selected from the group consisting of an aralkyl type phenol resin, a dicyclopentadiene type phenol resin, a triphenylmethane type phenol resin, a copolymerized type phenol resin of a benzaldehyde type phenol resin and an aralkyl type phenol resin, and a novolak type phenol resin is preferable. From the viewpoint of rapid hardening at low temperature, a novolak-type phenol resin is more preferable.
Specific examples of the aralkyl type phenol resin include phenol resins represented by the following general formulae (XII) to (XIV).
[ solution 13]
In the formulae (XII) to (XIV), R23The monovalent organic groups may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 18 carbon atoms. R22、R24、R25And R28The monovalent organic groups having 1 to 18 carbon atoms (in the case of a specific curing agent, electron donating groups are preferable) may be the same or different. R26And R27The monovalent organic groups may be the same or different and each represents a hydroxyl group or a C1-18 monovalent organic group. i each isIndependently an integer of 0 to 3, j independently an integer of 0 to 2, k independently an integer of 0 to 4, and p independently an integer of 0 to 4. n is an average value and is a number of 0 to 10 independently.
In the phenol resin represented by the general formula (XII), i is 0 and R23MEH-7851 (trade name, Ming and Kangsha Co., Ltd.) and the like, which are hydrogen atoms, are available as commercially available products.
Specific examples of the dicyclopentadiene type phenol resin include phenol resins represented by the following general formula (XV).
[ solution 14]
In the formula (XV), R29The monovalent organic groups having 1 to 18 carbon atoms (in the case of a specific curing agent, electron donating groups are preferable) may be the same or different. i independently represent an integer of 0 to 3. n is an average value and represents a number of 0 to 10.
Specific examples of the triphenylmethane type phenol resin include a phenol resin represented by the following general formula (XVI).
[ solution 15]
In the formula (XVI), R30And R31The monovalent organic groups having 1 to 18 carbon atoms (in the case of a specific curing agent, electron donating groups are preferable) 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 a number of 0 to 10.
Specific examples of the phenol resin of the copolymerization type of the benzaldehyde type phenol resin and the aralkyl type phenol resin include phenol resins represented by the following general formula (XVII).
[ solution 16]
In the formula (XVII), R32～R34A monovalent organic group having 1 to 18 carbon atoms (R in the case of a specific curing agent)32And R34Preferably electron-donating groups), which may be the same or different, respectively. i is independently an integer of 0 to 3, k is independently an integer of 0 to 4, and q is independently an integer of 0 to 5. l and m are average values and are each independently a number of 0 to 11. Wherein the sum of l and m is a number of 1 to 11.
Specific examples of the novolak-type phenol resin include a phenol resin represented by the following general formula (XVIII).
[ solution 17]
In the formula (XVIII), R35The hydrogen atom or monovalent organic group (preferably hydrogen atom) having 1 to 18 carbon atoms may be the same or different. R36The monovalent organic groups having 1 to 18 carbon atoms (in the case of a specific curing agent, electron donating groups are preferable) may be the same or different. i independently represent an integer of 0 to 3. n is an average value and represents a number of 0 to 10.
R in the general formula (XII) to (XVIII)22～R36The "may be the same or different" as defined in (A) means, for example, i R's in the formula (XII)22May be the same or different from each other. With respect to the other R23～R36It means that the numbers of the compounds contained in the formulae may be the same or different from each other. In addition, R22～R36Each may be the same or different. For example, R22And R23Either the same or different, R30And R31May be the same or different.
N in the general formulae (XII) to (XVIII) is preferably in the range of 0 to 10. If the viscosity is 10 or less, the melt viscosity of the resin component is not too high, and the viscosity of the curable resin composition during melt molding tends to be low. The average n in 1 molecule is preferably set to 0 to 4.
The functional group equivalent (hydroxyl group equivalent in the case of a phenolic hardener) of the hardener is not particularly limited. From the viewpoint of balance among various properties such as moldability, reflow resistance and electrical reliability, it is preferably from 70 to 1000g/eq, more preferably from 80 to 500 g/eq.
In the case where the hardening agent is a solid, the softening point or melting point thereof is not particularly limited. From the viewpoint of moldability and reflow resistance, it is preferably from 40 ℃ to 180 ℃, and from the viewpoint of workability in the production of the sealing resin composition, it is more preferably from 50 ℃ to 130 ℃.
The melting point or softening point of the curing agent is measured in the same manner as the melting point or softening point of the epoxy resin.
The equivalent ratio of the epoxy resin to the hardener, that is, the ratio of the number of functional groups in the hardener to the number of functional groups in the epoxy resin (the number of functional groups in the hardener/the number of functional groups in the epoxy resin) is not particularly limited. From the viewpoint of suppressing the amount of unreacted components to a small amount, the amount is preferably set to a range of 0.5 to 2.0, and more preferably set to a range of 0.6 to 1.3. From the viewpoint of moldability and reflow resistance, it is more preferably set to a range of 0.8 to 1.2.
(hardening accelerator)
The curable resin composition may also contain a curing accelerator. The type of the hardening accelerator is not particularly limited, and conventionally known hardening accelerators can be used. Examples thereof include: cyclic amidine compounds such as 1, 8-diaza-bicyclo (5,4,0) undecene-7, 1, 5-diaza-bicyclo (4,3,0) nonene, 5, 6-dibutylamino-1, 8-diaza-bicyclo (5,4,0) undecene-7 and the like; tertiary amine compounds such as triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris (dimethylaminomethyl) phenol, and the like; imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 2-phenyl-4, 5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 4-diamino-6- (2 '-methylimidazolyl- (1')) -ethyl-s-triazine, and 2-heptadecylimidazole; an organic phosphine compound such as trialkylphosphine (e.g., tributylphosphine), dialkylarylphosphine (e.g., dimethylphenylphosphine), alkyldiarylphosphine (e.g., methyldiphenylphosphine), triphenylphosphine, or an alkyl-substituted triphenylphosphine, and a compound having intramolecular polarization, which is obtained by adding a quinone compound such as maleic anhydride, 1, 4-benzoquinone, 2, 5-toluquinone, 1, 4-naphthoquinone, 2, 3-dimethylbenzoquinone, 2, 6-dimethylbenzoquinone, 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone, 2, 3-dimethoxy-1, 4-benzoquinone, or phenyl-1, 4-benzoquinone, diazophenylmethane, or a phenol resin to the organic phosphine compound; and derivatives of these. Further, there may be mentioned a phenylboronate such as 2-ethyl-4-methylimidazolium tetraphenylboronate and N-methylmorpholinium tetraphenylboronate. The hardening accelerator may be used alone or in combination of two or more.
From the viewpoint of promoting the reaction between the epoxy resin and the curing agent at low temperature, the curable resin composition preferably contains an imidazole compound.
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 (total of the epoxy resin and the curing agent). When the amount of the curing accelerator is 0.1 part by mass or more per 100 parts by mass of the resin component, the curing accelerator tends to be cured well in a short time. If the amount of the curing accelerator is 30 parts by mass or less based on 100 parts by mass of the resin component, a good molded article having a curing rate not too high tends to be obtained.
(inorganic Filler)
The curable resin composition may contain an inorganic filler. In particular, when the curable resin composition is used as a sealing material for semiconductor packages, it is preferable to contain an inorganic filler.
The kind of the inorganic filler is not particularly limited. Specifically, there may be mentioned: inorganic materials such as fused silica, 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 the like. Inorganic fillers having a flame retardant effect may also be used. Examples of the inorganic filler having a flame retardant effect include: and a composite metal hydroxide such as aluminum hydroxide, magnesium hydroxide, or a composite hydroxide of magnesium and zinc, zinc borate, and the like. Among them, fused silica is preferable from the viewpoint of a reduction in the 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. Examples of the state of the inorganic filler include powder, particles obtained by spheroidizing the powder, and fibers.
When the curable resin composition contains an inorganic filler, the content thereof is not particularly limited. From the viewpoint of fluidity and strength, the curable resin composition preferably has a volume of 30 to 90%, more preferably 35 to 80%, and still more preferably 40 to 70% of the entire curable resin composition. When the content of the inorganic filler is 30 vol% or more of the entire curable resin composition, the properties of the cured product, such as the thermal expansion coefficient, the thermal conductivity, and the elastic coefficient, tend to be further improved. When the content of the inorganic filler is 90 vol% or less of the entire curable resin composition, an increase in viscosity of the curable resin composition is suppressed, the flowability is further improved, and the moldability tends to be further improved.
The average particle diameter of the inorganic filler is not particularly limited. For example, the volume average particle diameter is preferably 0.2 to 10 μm, more preferably 0.5 to 5 μm. When the volume average particle diameter is 0.2 μm or more, the increase in viscosity of the curable resin composition tends to be further suppressed. When the volume average particle diameter is 10 μm or less, the filling property to narrow gaps tends to be further improved. The volume 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 of the inorganic filler in the curable resin composition or the cured product thereof can be measured by a known method. For example, an inorganic filler is extracted from a self-curable resin composition or a cured product using an organic solvent, nitric acid, aqua regia, or the like, and sufficiently dispersed by an ultrasonic disperser or the like to prepare a dispersion liquid. 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 embedding a cured product in a transparent epoxy resin or the like, polishing the cured product to obtain a cross section, and observing the obtained cross section with a scanning electron microscope. Further, the measurement can be performed as follows: two-dimensional cross-sectional observation of the cured product was continuously performed using an FIB device (focused ion beam SEM) or the like, and three-dimensional structural analysis was performed.
From the viewpoint of fluidity of the curable resin composition, the particle shape of the inorganic filler is preferably spherical rather than angular, and the particle size distribution of the inorganic filler is preferably distributed in a wide range.
[ various additives ]
The curable resin composition may contain, in addition to the above components, various additives such as a coupling agent, an ion exchanger, a mold release agent, a flame retardant, a colorant, and a stress relaxation agent, which are exemplified below. The curable resin composition may contain, in addition to the additives exemplified below, various additives known in the art as needed.
(coupling agent)
When the curable resin composition contains an inorganic filler, a coupling agent may be contained to improve the adhesion between the resin component and the inorganic filler. Examples of coupling agents include: known coupling agents such as silane-based compounds such as epoxysilane, mercaptosilane, aminosilane, alkylsilane, ureasilane and vinylsilane, titanium-based compounds, aluminum chelate compounds and aluminum/zirconium-based compounds.
When the curable resin composition contains a coupling agent, the amount of the coupling agent is preferably 0.05 to 5 parts by mass, more preferably 0.1 to 2.5 parts by mass, per 100 parts by mass of the inorganic filler. When the amount of the coupling agent is 0.05 parts by mass or more per 100 parts by mass of the inorganic filler, the adhesion to the frame (frame) tends to be further improved. When the amount of the coupling agent is 5 parts by mass or less based on 100 parts by mass of the inorganic filler, the moldability of the package tends to be further improved.
(ion exchanger)
The curable resin composition may contain an ion exchanger. In particular, when the curable resin composition is used as a molding material for sealing, it is preferable to contain an ion exchanger from the viewpoint of improving the moisture resistance and high-temperature storage characteristics of an electronic component device including a sealed element. The ion exchanger is not particularly limited, and conventionally known ion exchangers can be used. Specifically, there may be mentioned hydrotalcite compounds, hydroxides containing at least one element selected from the group consisting of magnesium, aluminum, titanium, zirconium and bismuth, and the like. The ion exchanger may be used alone or in combination of two or more. Among them, preferred is hydrotalcite represented by the following general formula (a).
Mg(1-X)AlX(OH)2(CO3)X/2·mH2O······(A)
(X is more than 0 and less than or equal to 0.5, and m is a positive number)
When the curable resin composition 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 ions or the like. For example, the amount 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.
(mold releasing agent)
The curable resin composition may contain a release agent from the viewpoint of obtaining good releasability from a mold at the time of molding. The release agent is not particularly limited, and conventionally known release agents can be used. Specific examples thereof include: and higher fatty acids such as carnauba wax (carnauba wax), octacosanoic acid, stearic acid, metal salts of higher fatty acids, ester waxes such as octacosanoic acid esters, polyolefin waxes such as oxidized polyethylene and non-oxidized polyethylene. The release agent may be used alone or in combination of two or more.
When the curable resin composition contains a release agent, the amount of the release agent is preferably 0.01 to 15 parts by mass, and more preferably 0.1 to 10 parts by mass, per 100 parts by mass of the resin component. When the amount of the release agent is 0.01 parts by mass or more per 100 parts by mass of the resin component, sufficient releasability tends to be obtained. When the amount is 15 parts by mass or less, more favorable adhesion tends to be obtained.
(flame retardant)
The curable resin composition may also contain a flame retardant. The flame retardant is not particularly limited, and conventionally known flame retardants can be used. Specifically, examples thereof include organic or inorganic compounds containing a halogen atom, an antimony atom, a nitrogen atom or a phosphorus atom, and metal hydroxides. One kind of the flame retardant may be used alone, or two or more kinds may be used in combination.
In the case where the curable resin composition contains a flame retardant, the amount of the flame retardant is not particularly limited as long as the amount is sufficient for obtaining a desired flame retardant effect. For example, the amount is preferably 1 to 300 parts by mass, more preferably 2 to 150 parts by mass, per 100 parts by mass of the resin component.
(coloring agent)
The curable resin composition may further contain a colorant. Examples of the colorant include known colorants such as carbon black, organic dyes, organic pigments, titanium oxide, red lead, and iron oxide. The content of the colorant can be appropriately selected depending on the purpose and the like. The colorant may be used alone or in combination of two or more.
(stress relaxation Agents)
The curable resin composition may contain a stress relaxation agent such as silicone oil or silicone rubber particles. By including a stress relaxation agent, the occurrence of warpage of the package and package cracks can be further reduced. As the stress relaxation agent, a commonly used known stress relaxation agent (flexibility agent) can be mentioned. Specifically, there may be mentioned thermoplastic elastomers such as silicone-based, styrene-based, olefin-based, urethane-based, polyester-based, polyether-based, polyamide-based, and polybutadiene-based elastomers, rubber particles such as Natural Rubber (NR), 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 (MBS), methyl Methacrylate-silicone copolymer, and methyl Methacrylate-butyl acrylate copolymer. The stress relaxation agent may be used alone or in combination of two or more. Among them, silicone-based stress relaxers are preferable. Examples of the silicone-based stress relaxation agent include a stress relaxation agent having an epoxy group, a stress relaxation agent having an amino group, and a stress relaxation agent obtained by polyether-modifying these.
(method for producing curable resin composition)
The method for preparing the curable resin composition is not particularly limited. The following methods can be mentioned as a general method: after the components are sufficiently mixed at a predetermined blending ratio by a mixer or the like, they are melt-kneaded by a grinding roll, an extruder or the like, cooled and pulverized. More specifically, for example, the following methods can be mentioned: the prescribed amounts of the above components are uniformly stirred and mixed, kneaded and cooled by a kneader, roll, extruder or the like heated in advance to 70 to 140 ℃, and pulverized.
The curable resin composition is preferably a solid at normal temperature and normal pressure (e.g., 25 ℃ C., atmospheric pressure). The shape of the curable resin composition in the case of a solid is not particularly limited, and examples thereof include powder, granule, and tablet. From the viewpoint of workability, the size and mass of the curable resin composition in the form of a sheet are preferably those according to the molding conditions of the package.
< electronic component device >
An electronic component device according to an embodiment of the present invention includes: an element; and a cured product of the curable resin composition for sealing the element.
As an electronic component device, there is exemplified an electronic component device in which an element section obtained by mounting an element (an active element such as a semiconductor chip, a transistor, a diode, or a thyristor, a passive element such as a capacitor, a resistor, or a coil, or the like) on a support member such as a lead frame, a wired carrier tape, a wiring board, glass, a silicon wafer, or an organic substrate is sealed with a curable resin composition.
More specifically, there may be mentioned: a general resin-sealed IC such as a Dual Inline Package (DIP), a Plastic Leaded Chip Carrier (PLCC), a Quad Flat Package (QFP), a Small Outline Package (SOP), a Small Outline J-lead Package (SOJ), a Thin Outline Package (TSOP), a Thin Quad Flat Package (TQFP), or the like, which has a structure in which after an element is fixed on a lead frame and a terminal portion and a lead portion of the element such as a bonding pad and the like are connected by wire bonding, a bump and the like, the terminal portion and the lead portion of the element are sealed by transfer molding or the like using a curable resin composition; a Tape Carrier Package (TCP) having a structure in which a component connected to a Carrier Tape by bumps is sealed with a curable resin composition; chip On Board (COB) modules, hybrid ICs, polycrystalline modules, and the like, which have a structure in which elements connected to wires formed On a support member by wire bonding, flip Chip bonding, solder, and the like are sealed with a curable resin composition; a Ball Grid Array (BGA), a Chip Size Package (CSP), a Multi-Chip Package (MCP), or the like, has a structure in which an element is mounted on a surface of a support member having terminals for wiring board connection formed on a back surface thereof, the element is connected to a wiring formed on the support member by bump or wire bonding, and then the element is sealed with a curable resin composition. In addition, a curable resin composition can also be preferably used for the printed wiring board.
Examples of the method for sealing the electronic component device with the curable resin composition include low-pressure transfer molding, injection molding, and compression molding. Of these, a low-pressure transfer molding method is generally used.
Further, a method called Molded Underfill (MUF) is exemplified. The mold underfill is a method of sealing a gap between the semiconductor chip and the substrate (underfill) and sealing an upper portion of the semiconductor chip (overmolding) at a time.
[ examples ]
The embodiments are specifically described below with reference to examples, but the scope of the embodiments is not limited to these examples.
[ preparation of curable resin composition ]
The following materials were mixed in the composition (parts by mass) shown in table 1, and roll-kneaded at a kneading temperature of 80 ℃ for 15 minutes to prepare a curable resin composition.
Epoxy resin 1: an epoxy group-containing triphenylmethane epoxy resin (product name: EPPN-501HY, manufactured by Nippon chemical Co., Ltd.) having an epoxy group bonded to an aromatic ring to which an electron donating group (methyl group) is bonded, an epoxy equivalent of 196g/eq, a melting point of 106 ℃ C
Epoxy resin 2: an epoxy group-containing biphenyl type epoxy resin (trade name "YX-4000H" from Mitsubishi chemical corporation) having an electron donating group (methyl group) bonded to an aromatic ring, an epoxy equivalent of 196g/eq, a melting point of 106 ℃ C
Epoxy resin 3: an epoxy resin having a biphenyl structure (25 mass%) to which an electron donating group is not bonded to an aromatic ring and a triphenylmethane structure (75 mass%) to which an electron donating group is not bonded to an aromatic ring (trade name "YL 6677") having an epoxy equivalent of 155g/eq to 170g/eq, a softening point of 60 ℃ to 100 DEG C
Epoxy resin 4: a mixture of 4,4' -biphenyldiylbis (glycidyl ether) and 3,3',5,5' -tetramethyl-4, 4' -bis (glycidyloxy) -1,1' -biphenyl (mass ratio 1: 1) (trade name "YL 6121" from Mitsubishi chemical corporation), an epoxy equivalent of 170g/eq to 180g/eq, a softening point of 60 ℃ to 100 DEG C
Hardening agent 1: a triphenylmethane type phenol resin (trade name "MEH 7500-3S" from Minghe Kaisha Co., Ltd.), having a hydroxyl group equivalent of 103g/eq, a softening point of 83 ℃ C., and having no electron donating group bonded to an aromatic ring having an epoxy group bonded thereto
Hardening agent 2: o-cresol novolac resin (trade name "MEH 5100-5S" from Minghe Kasei Co., Ltd.), hydroxyl equivalent weight of 116g/eq, softening point of 64 deg.C
Hardening agent 3: phenol novolac resin (trade name "HP-850N" from Hitachi chemical Co., Ltd.) having no electron donating group bonded to the aromatic ring, a hydroxyl equivalent of 106g/eq, and a softening point of 83 deg.C
Hardening accelerator 1: addition product of tributylphosphine and benzoquinone
Hardening accelerator 2: 2-phenyl-4-methylimidazole
Coupling agent 1: 3-methacryloxypropyltrimethoxysilane
Coupling agent 2: n-phenyl-3-aminopropyltrimethoxysilane
Mold release agent 1: octaconic acid ester
Colorant 1: carbon black
Stress relaxation agent 1: styrene-indene copolymer resin
Stress relaxation agent 2: liquid silicon having epoxy group and polyether group in side chain
Inorganic filler 1: spherical fused silica (volume average particle diameter 5 μm)
Inorganic filler 2: fine-ball fused silica (volume average particle diameter 0.5 μm)
[ evaluation of flowability ]
As an index for evaluation of fluidity, a swirling flow test was performed. Specifically, the flow distance (cm) of the curable resin composition at a curing time of 120 seconds/175 ℃ and a curing time of 600 seconds/130 ℃ was determined at a Molding pressure of 6.9MPa using a mold for vortex measurement conforming to Epoxy Molding Material Institute (EMMI) -1-66. The results are shown in Table 1.
[ evaluation of gel time ]
The curable resin composition 3g was measured at 175 ℃ and 130 ℃ using a curelastometer (currastometer) manufactured by JSR tirelin corporation, and the time taken until the torque curve rose was defined as the gel time (sec). The results are shown in Table 1.
[ evaluation of hardenability at Low temperature ]
Using an Epigg G-Line (apic G-Line) (MZ674-1) transfer molding machine, a Cu plate 240 mm. times.74 mm square was molded in a Mold Array Package (MAP) at a temperature and for a time shown in Table 1, assuming that the molding thickness of the curable resin composition was 500 μm (molding pressure 3 MPa). The appearance of the surface (strip surface) and the scrap (cut) of the formed strip was confirmed, and the hardenability at low temperature was evaluated according to the following criteria. The results are shown in Table 1.
A: the surface of the molded article on the substrate is sufficiently cured, and the residue portion is free from swelling and the like.
B: the surface of the molded article on the substrate has sufficient hardening properties, but the residue portion has swelling or the like.
C: an unhardened portion is produced.
[ Table 1]
As shown in table 1, the curable resin compositions of examples using the epoxy resin containing an epoxy group (part of the epoxy resin 3 and the epoxy resin 4) bonded to the aromatic ring to which the electron donating group is not bonded and the curing agent (curing agent 2) having a hydroxyl group bonded to the aromatic ring to which the electron donating group is bonded have better curing properties at low temperatures than the curable resin compositions of comparative examples which do not satisfy these conditions.
Furthermore, the curable resin compositions of examples 3 and 4 using an imidazole compound as a curing accelerator have better curability at low temperatures than the curable resin compositions of examples 1 and 2 using a curing accelerator different from an imidazole compound.
Claims (8)
1. A curable resin composition comprising an epoxy resin and a curing agent, wherein the epoxy resin comprises an epoxy group-containing epoxy resin having an epoxy group bonded to an aromatic ring to which an electron-donating group is not bonded, and the curing agent comprises a curing agent having a hydroxyl group bonded to an aromatic ring to which an electron-donating group is bonded.
2. The curable resin composition according to claim 1, wherein the electron-donating group is at least one selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an amino group and a methoxy group.
3. The curable resin composition according to claim 1 or 2, wherein the epoxy group-containing epoxy resin bonded to the aromatic ring to which an electron-donating group is not bonded has a biphenyl structure.
4. The curable resin composition according to any one of claims 1 to 3, wherein the curing agent having a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded has a structure obtained by novolak-converting a phenol compound to which the electron-donating group is bonded.
5. The curable resin composition according to any one of claims 1 to 4, wherein the curing agent having a hydroxyl group bonded to the aromatic ring to which the electron-donating group is bonded has a structure obtained by novolak-converting a phenol compound to which the electron-donating group is bonded at an ortho position.
6. The curable resin composition according to any one of claims 1 to 5, further comprising an imidazole compound.
7. The curable resin composition according to any one of claims 1 to 6, which is used as a sealing material for electronic component devices.
8. An electronic part device comprising: an element; and a cured product of the curable resin composition according to any one of claims 1 to 7 sealing the element.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-029777 | 2019-02-21 | ||
| JP2019029777 | 2019-02-21 | ||
| PCT/JP2020/005993 WO2020171004A1 (en) | 2019-02-21 | 2020-02-17 | Curable resin composition and electronic component device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113195585A true CN113195585A (en) | 2021-07-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202080007052.5A Pending CN113195585A (en) | 2019-02-21 | 2020-02-17 | Curable resin composition and electronic component device |
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|---|---|
| JP (2) | JP7533439B2 (en) |
| CN (1) | CN113195585A (en) |
| TW (1) | TW202035558A (en) |
| WO (1) | WO2020171004A1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006002139A (en) * | 2004-05-20 | 2006-01-05 | Nippon Kayaku Co Ltd | Phenolic resin, epoxy resin, and cured product of the same |
| US20080054234A1 (en) * | 2006-09-04 | 2008-03-06 | Chang Chun Plastics Co., Ltd. | Flame retardative resin composition |
| JP2008231239A (en) * | 2007-03-20 | 2008-10-02 | Dic Corp | Curable resin composition, cured product thereof, new phenol resin and method for producing the same |
| JP2009179764A (en) * | 2008-02-01 | 2009-08-13 | Sumitomo Bakelite Co Ltd | Semiconductor sealing resin composition and semiconductor device |
| US20120205822A1 (en) * | 2009-10-26 | 2012-08-16 | Yusuke Tanaka | Resin composition for encapsulating semiconductor and semiconductor device using the resin composition |
| US20140151091A1 (en) * | 2011-05-31 | 2014-06-05 | Daisuke Fujimoto | Primer layer for plating process, laminate for circuit board and production method for same, and multilayer circuit board and production method for same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268721A (en) * | 1985-05-24 | 1986-11-28 | Asahi Chem Ind Co Ltd | Curing agent for epoxy resin |
| JP2009231605A (en) * | 2008-03-24 | 2009-10-08 | Sekisui Chem Co Ltd | Adhesive and method of manufacturing bonded body |
| JP5463110B2 (en) * | 2009-09-24 | 2014-04-09 | ナミックス株式会社 | Coverlay film |
| JP5736718B2 (en) * | 2010-10-18 | 2015-06-17 | Jsr株式会社 | Radiation-sensitive resin composition, cured film and method for forming the same |
-
2020
- 2020-02-17 WO PCT/JP2020/005993 patent/WO2020171004A1/en active Application Filing
- 2020-02-17 JP JP2021501971A patent/JP7533439B2/en active Active
- 2020-02-17 CN CN202080007052.5A patent/CN113195585A/en active Pending
- 2020-02-19 TW TW109105367A patent/TW202035558A/en unknown
-
2024
- 2024-05-17 JP JP2024080887A patent/JP2024100861A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006002139A (en) * | 2004-05-20 | 2006-01-05 | Nippon Kayaku Co Ltd | Phenolic resin, epoxy resin, and cured product of the same |
| US20080054234A1 (en) * | 2006-09-04 | 2008-03-06 | Chang Chun Plastics Co., Ltd. | Flame retardative resin composition |
| JP2008231239A (en) * | 2007-03-20 | 2008-10-02 | Dic Corp | Curable resin composition, cured product thereof, new phenol resin and method for producing the same |
| JP2009179764A (en) * | 2008-02-01 | 2009-08-13 | Sumitomo Bakelite Co Ltd | Semiconductor sealing resin composition and semiconductor device |
| US20120205822A1 (en) * | 2009-10-26 | 2012-08-16 | Yusuke Tanaka | Resin composition for encapsulating semiconductor and semiconductor device using the resin composition |
| US20140151091A1 (en) * | 2011-05-31 | 2014-06-05 | Daisuke Fujimoto | Primer layer for plating process, laminate for circuit board and production method for same, and multilayer circuit board and production method for same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2024100861A (en) | 2024-07-26 |
| JP7533439B2 (en) | 2024-08-14 |
| JPWO2020171004A1 (en) | 2020-08-27 |
| WO2020171004A1 (en) | 2020-08-27 |
| TW202035558A (en) | 2020-10-01 |
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