JPWO2017188455A1 - エポキシ樹脂組成物及び電子部品装置 - Google Patents
エポキシ樹脂組成物及び電子部品装置 Download PDFInfo
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- JPWO2017188455A1 JPWO2017188455A1 JP2018514747A JP2018514747A JPWO2017188455A1 JP WO2017188455 A1 JPWO2017188455 A1 JP WO2017188455A1 JP 2018514747 A JP2018514747 A JP 2018514747A JP 2018514747 A JP2018514747 A JP 2018514747A JP WO2017188455 A1 JPWO2017188455 A1 JP WO2017188455A1
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- Prior art keywords
- epoxy resin
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- resin composition
- general formula
- mass
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 179
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 42
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 125000001424 substituent group Chemical group 0.000 claims abstract description 35
- 239000005011 phenolic resin Substances 0.000 claims abstract description 24
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims abstract description 14
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 phosphine compound Chemical group 0.000 claims description 48
- 239000011256 inorganic filler Substances 0.000 claims description 20
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 20
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 17
- 239000007822 coupling agent Substances 0.000 claims description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 84
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- 239000002994 raw material Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 14
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 13
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 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 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 8
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- 125000003700 epoxy group Chemical group 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 125000004434 sulfur atom Chemical group 0.000 description 8
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- 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 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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 6
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003860 storage Methods 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
- 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 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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- 229920001568 phenolic resin Polymers 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-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
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 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
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- DCWHTLFWGFZFJD-UHFFFAOYSA-N n-[3-[diethoxy(ethyl)silyl]propyl]-4-methoxyaniline Chemical compound CCO[Si](CC)(OCC)CCCNC1=CC=C(OC)C=C1 DCWHTLFWGFZFJD-UHFFFAOYSA-N 0.000 description 1
- AHLSHTSIRHIXOJ-UHFFFAOYSA-N n-[3-[diethoxy(ethyl)silyl]propyl]aniline Chemical compound CCO[Si](CC)(OCC)CCCNC1=CC=CC=C1 AHLSHTSIRHIXOJ-UHFFFAOYSA-N 0.000 description 1
- FIZALOOFPVCKRG-UHFFFAOYSA-N n-[3-[diethoxy(methyl)silyl]propyl]-4-methoxyaniline Chemical compound CCO[Si](C)(OCC)CCCNC1=CC=C(OC)C=C1 FIZALOOFPVCKRG-UHFFFAOYSA-N 0.000 description 1
- NQKOSCFDFJKWOX-UHFFFAOYSA-N n-[3-[diethoxy(methyl)silyl]propyl]aniline Chemical compound CCO[Si](C)(OCC)CCCNC1=CC=CC=C1 NQKOSCFDFJKWOX-UHFFFAOYSA-N 0.000 description 1
- ZVNKDTRPKUHGII-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]-4-methoxyaniline Chemical compound COC1=CC=C(NCCC[Si](C)(OC)OC)C=C1 ZVNKDTRPKUHGII-UHFFFAOYSA-N 0.000 description 1
- YZPARGTXKUIJLJ-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]aniline Chemical compound CO[Si](C)(OC)CCCNC1=CC=CC=C1 YZPARGTXKUIJLJ-UHFFFAOYSA-N 0.000 description 1
- CKVDDFGLMMACDH-UHFFFAOYSA-N n-[3-[ethyl(dimethoxy)silyl]propyl]-4-methoxyaniline Chemical compound CC[Si](OC)(OC)CCCNC1=CC=C(OC)C=C1 CKVDDFGLMMACDH-UHFFFAOYSA-N 0.000 description 1
- QKPXAVZCBOLFFL-UHFFFAOYSA-N n-[3-[ethyl(dimethoxy)silyl]propyl]aniline Chemical compound CC[Si](OC)(OC)CCCNC1=CC=CC=C1 QKPXAVZCBOLFFL-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 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
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical class NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
- XDHRVAHAGMMFMC-UHFFFAOYSA-N tris(2,4-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC=C1P(C=1C(=CC(C)=CC=1)C)C1=CC=C(C)C=C1C XDHRVAHAGMMFMC-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
- CKKFLUXMIUUGAW-UHFFFAOYSA-N tris(2-propan-2-ylphenyl)phosphane Chemical compound CC(C)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(C)C)C1=CC=CC=C1C(C)C CKKFLUXMIUUGAW-UHFFFAOYSA-N 0.000 description 1
- GDKAFTKCUOBEDW-UHFFFAOYSA-N tris(2-tert-butylphenyl)phosphane Chemical compound CC(C)(C)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C GDKAFTKCUOBEDW-UHFFFAOYSA-N 0.000 description 1
- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- SPNVODOGUAUMCA-UHFFFAOYSA-N tris(4-ethoxy-2,6-dimethylphenyl)phosphane Chemical compound CC1=CC(OCC)=CC(C)=C1P(C=1C(=CC(OCC)=CC=1C)C)C1=C(C)C=C(OCC)C=C1C SPNVODOGUAUMCA-UHFFFAOYSA-N 0.000 description 1
- LQEKTSMTEYLBLJ-UHFFFAOYSA-N tris(4-ethoxyphenyl)phosphane Chemical compound C1=CC(OCC)=CC=C1P(C=1C=CC(OCC)=CC=1)C1=CC=C(OCC)C=C1 LQEKTSMTEYLBLJ-UHFFFAOYSA-N 0.000 description 1
- JTOQWGJGVSYTTN-UHFFFAOYSA-N tris(4-propylphenyl)phosphane Chemical compound C1=CC(CCC)=CC=C1P(C=1C=CC(CCC)=CC=1)C1=CC=C(CCC)C=C1 JTOQWGJGVSYTTN-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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
Description
ビフェニレン型フェノールアラルキル樹脂、フェノールアラルキル樹脂、及びトリフェニルメタン型フェノール樹脂からなる群より選択される少なくとも1種を含む硬化剤と、
を含有するエポキシ樹脂組成物。
〔R1は、各々独立に、水素原子又は炭素数1〜6の一価の炭化水素基を示し、R2は式(a)で示される置換基を示し、mは0〜20の数を示し、pは0.5〜2.0を示し、R3は、各々独立に、水素原子又は炭素数1〜6の一価の炭化水素基を示す。〕
前記素子を封止する<1>〜<7>のいずれか1つに記載のエポキシ樹脂組成物の硬化物と、
を備える電子部品装置。
更に、本明細書において組成物中の各成分の含有率は、組成物中に各成分に該当する物質が複数存在する場合には、特に断らない限り、組成物中に存在する当該複数の物質の合計の含有率を意味する。
本明細書中に段階的に記載されている数値範囲において、一つの数値範囲で記載された上限値又は下限値は、他の段階的な記載の数値範囲の上限値又は下限値に置き換えてもよい。また、本明細書中に記載されている数値範囲において、その数値範囲の上限値又は下限値は、実施例に示されている値に置き換えてもよい。
本明細書において組成物中の各成分の粒子径は、組成物中に各成分に該当する粒子が複数種存在する場合、特に断らない限り、組成物中に存在する当該複数種の粒子の混合物についての値を意味する。
本発明の一実施形態に係るエポキシ樹脂組成物は、下記一般式(1)で示される化合物(以下、「特定エポキシ樹脂」ともいう)を含むエポキシ樹脂と、ビフェニレン型フェノールアラルキル樹脂、フェノールアラルキル樹脂、及びトリフェニルメタン型フェノール樹脂からなる群より選択される少なくとも1種を含む硬化剤(以下「特定の硬化剤」ともいう)と、を含有する。
また、溶融粘度が低くなることにより流動性が高くなって成形性に優れると考えられる。
エポキシ樹脂組成物は、エポキシ樹脂を含有する。エポキシ樹脂は、下記一般式(1)で示される化合物を含む。
(1)温度レンジを150℃に設定して、(2)試料0.15g〜0.25gをプレート上で溶融し、コーンを降ろし、温度コントロールランプの点滅を5回繰り返すまで放置する。(3)コーンの上下攪拌を約20秒行い、その後温度コントロールランプの点滅が5回繰り返されるまで放置する。(4)コーン回転後、約15秒後の値を読む。(5)値が同一になるまで(3)〜(4)の操作を繰り返し、その値を記録する。(6)同一ロットで3回以上(2)〜(5)の操作を繰り返し、その平均値を粘度とする。
100mLのフラスコにエポキシ樹脂を固形分が3g〜4gになるよう量り、酢酸20mL、臭化テトラエチルアンモニウム酢酸溶液(臭化テトラエチルアンモニウム100gと酢酸400mLの混合液)を10mL、クリスタルバイオレットを4滴〜5滴加える。この溶液を0.1mol/Lの過塩素酸酢酸溶液で滴定する。同様にブランクを滴定する。エポキシ当量は以下の式により算出する。
エポキシ樹脂組成物は硬化剤を含有する。硬化剤は、ビフェニレン型フェノールアラルキル樹脂、フェノールアラルキル樹脂、及びトリフェニルメタン型フェノール樹脂からなる群より選択される少なくとも1種を含む。
硬化剤は、更に特定の硬化剤以外に他の硬化剤を併用してもよい。全硬化剤中の特定の硬化剤の含有率は、30質量%以上であることが好ましく、50質量%以上であることがより好ましく、70質量%以上であることが更に好ましい。
ピリジン−塩化アセチル法を用い、硬化剤の水酸基をピリジン溶液中で塩化アセチル化した後にその過剰の試薬を水で分解し、生成した酢酸を水酸化カリウム及びエタノールを含む溶液で滴定して、水酸基当量を求める。
エポキシ樹脂組成物には、エポキシ樹脂と硬化剤の反応を促進させる観点から、必要に応じて硬化促進剤を用いてもよい。
硬化促進剤は、エポキシ樹脂組成物に一般に使用されているものを特に制限なく用いることができる。硬化促進剤としては、1,8−ジアザ−ビシクロ[5.4.0]ウンデセン−7、1,5−ジアザ−ビシクロ[4.3.0]ノネン、5,6−ジブチルアミノ−1,8−ジアザ−ビシクロ[5.4.0]ウンデセン−7等のシクロアミジン化合物;シクロアミジン化合物に無水マレイン酸、1,4−ベンゾキノン、2,5−トルキノン、1,4−ナフトキノン、2,3−ジメチルベンゾキノン、2,6−ジメチルベンゾキノン、2,3−ジメトキシ−5−メチル−1,4−ベンゾキノン、2,3−ジメトキシ−1,4−ベンゾキノン、フェニル−1,4−ベンゾキノン等のキノン化合物、ジアゾフェニルメタン、フェノール樹脂等のπ結合をもつ化合物を付加してなる分子内分極を有する化合物;ベンジルジメチルアミン、トリエタノールアミン、ジメチルアミノエタノール、トリス(ジメチルアミノメチル)フェノール等の3級アミン化合物;3級アミン化合物の誘導体;2−メチルイミダゾール、2−フェニルイミダゾール、2−フェニル−4−メチルイミダゾール等のイミダゾール化合物;イミダゾール化合物の誘導体;トリブチルホスフィン、メチルジフェニルホスフィン、トリフェニルホスフィン、トリス(4−メチルフェニル)ホスフィン、ジフェニルホスフィン、フェニルホスフィン等のホスフィン化合物;これらのホスフィン化合物に無水マレイン酸、上記キノン化合物、ジアゾフェニルメタン、フェノール樹脂等のπ結合をもつ化合物を付加してなる分子内分極を有するリン化合物;テトラフェニルホスホニウムテトラフェニルボレート、トリフェニルホスフィンテトラフェニルボレート、2−エチル−4−メチルイミダゾールテトラフェニルボレート、N−メチルモルホリンテトラフェニルボレート等のテトラフェニルボロン塩;テトラフェニルボロン塩の誘導体などが挙げられる。硬化促進剤は、これら1種を単独で用いても2種以上を組み合わせて用いてもよい。
エポキシ樹脂組成物は、更に、無機充填剤を含有してもよい。無機充填剤を含有すると、吸湿性の低減、線膨張係数の低減、熱伝導性の向上及び強度の向上の傾向がある。無機充填剤としては、溶融シリカ、結晶シリカ、アルミナ、ジルコン、珪酸カルシウム、炭酸カルシウム、チタン酸カリウム、炭化珪素、窒化珪素、窒化アルミ、窒化ホウ素、ベリリア、ジルコニア、ジルコン、フォステライト、ステアタイト、スピネル、ムライト、チタニア等の粉体、これらを球形化したビーズ、ガラス繊維などが挙げられる。更に、難燃効果のある無機充填剤としては、水酸化アルミニウム、水酸化マグネシウム、複合金属水酸化物、硼酸亜鉛、モリブデン酸亜鉛等が挙げられる。ここで、ホウ酸亜鉛としては、FB−290、FB−500(U.S.Borax社)、FRZ−500C(水澤化学工業株式会社)等が各々市販品として入手可能であり、モリブデン酸亜鉛としては、KEMGARD911B、911C、1100(Sherwin−Williams社)等が各々市販品として入手可能である。
エポキシ樹脂組成物は、更に、カップリング剤を含有してもよい。エポキシ樹脂組成物に無機充填剤を用いる場合、カップリング剤は樹脂成分と無機充填剤との接着性を高める傾向にある。カップリング剤としては、エポキシ樹脂組成物に一般に使用されているものを特に制限なく用いることができる。カップリング剤としては、1級、2級又は3級アミノ基を有するシラン化合物、エポキシシラン、メルカプトシラン、アルキルシラン、ウレイドシラン、ビニルシラン等の各種シラン化合物、チタン化合物、アルミニウムキレート化合物、アルミニウム及びジルコニウム含有化合物等が挙げられる。
エポキシ樹脂組成物は、難燃性の向上の観点から、更に、従来公知の難燃剤、特に環境対応、信頼性の観点からはノンハロゲン及びノンアンチモンの難燃剤を必要に応じて含有してもよい。難燃剤としては、赤リン、リン酸エステル、酸化亜鉛等の無機化合物、フェノール樹脂等の熱硬化性樹脂で被覆された赤リン、ホスフィンオキサイド等の樹脂被覆リン化合物、メラミン、メラミン誘導体、メラミン変性フェノール樹脂、トリアジン環を有する化合物、シアヌル酸誘導体、イソシアヌル酸誘導体等の窒素含有化合物、シクロホスファゼン等のリン、窒素含有化合物、水酸化アルミニウム、水酸化マグネシウム、複合金属水酸化物、酸化亜鉛、錫酸亜鉛、硼酸亜鉛、酸化鉄、酸化モリブデン、モリブデン酸亜鉛、ジシクロペンタジエニル鉄等の金属元素を含む化合物などが挙げられる。難燃剤は、これらの1種を単独で用いても、2種以上を組み合わせて用いてもよい。
エポキシ樹脂組成物は、反り低減の観点から、ケイ素含有重合物を含有してもよい。ケイ素含有重合物としては、下記の結合(c)及び(d)を有し、末端がR1、水酸基及びアルコキシ基からなる群より選択される基であり、エポキシ当量が500g/eq〜4000g/eqである化合物が好ましい。ケイ素含有重合物として、例えば、シリコーンレジンと呼ばれる分岐状ポリシロキサンが挙げられる。
エポキシ樹脂組成物は、IC等の半導体素子の耐湿性及び高温放置特性を向上させる観点から、必要に応じて下記組成式(XXXIII)で表される化合物及び下記組成式(XXXIV)で表される化合物からなる群より選択される少なくとも1種を含有してもよい。
(0<X≦0.5、mは正の数)
(0.9≦x≦1.1、0.6≦y≦0.8、0.2≦z≦0.4)
エポキシ樹脂組成物は、各種原材料を均一に分散混合できるのであれば、いかなる手法を用いて調製してもよい。一般的な調製方法として、所定の配合量の原材料をミキサー等によって充分混合した後、ミキシングロール、押出機、らいかい機、プラネタリミキサ等によって混合又は溶融混練し、冷却し、必要に応じて脱泡し、粉砕する方法等が挙げられる。また、エポキシ樹脂組成物は、必要に応じて成形条件に合うような寸法及び質量でタブレット化してもよい。
本発明の一実施形態に係る電子部品装置は、素子と、前記素子を封止する前述のエポキシ樹脂組成物の硬化物と、を備える。本実施形態のエポキシ樹脂組成物を封止材として用いて、素子を封止する方法としては、低圧トランスファ成形法が一般的であるが、インジェクション成形法、圧縮成形法等も挙げられる。エポキシ樹脂組成物の付与方法として、ディスペンス方式、注型方式、印刷方式等を用いてもよい。
特定エポキシ樹脂は以下のように合成できる。
原料フェノールノボラック樹脂を酸触媒であるp−トルエンスルホン酸を用いて原料ベンジル基含有化合物と反応させ、まず特定のフェノールノボラック樹脂を得る。この時、前述の硬化剤における水酸基当量の測定方法と同様にして水酸基当量を測定し、この値から一般式(1)におけるpの値求める。
次に上記で得られた特定のフェノールノボラック樹脂をエピクロルヒドリンにてエポキシ化する。得られた樹脂のエポキシ当量、軟化点及び150℃の溶融粘度を以下の表1に示す。なお、得られた特定エポキシ樹脂は、一般式(1)におけるR2がベンジル基(R3が水素原子)であった。
下記成分をそれぞれ表2及び3に示す質量部で配合し、混練温度80℃、混練時間10分の条件でロール混練を行い、実施例1〜4、比較例1〜8を作製した。
・エポキシ樹脂1:エポキシ当量240g/eq、軟化点55℃、一般式(1)で示される化合物であり、p=0.6のエポキシ樹脂
・エポキシ樹脂2:エポキシ当量263g/eq、軟化点58℃、一般式(1)で示される化合物であり、p=0.9のエポキシ樹脂
・エポキシ樹脂3:エポキシ当量264g/eq、軟化点60℃、一般式(1)で示される化合物であり、p=1.0のエポキシ樹脂
・エポキシ樹脂4:エポキシ当量265g/eq、軟化点61℃、一般式(1)で示される化合物であり、p=1.1のエポキシ樹脂
・エポキシ樹脂5:エポキシ当量251g/eq、軟化点60℃、2−メトキシナフタレンとオルソクレゾールノボラック型エポキシ樹脂の共重合物(DIC株式会社、商品名HP−5000)
・エポキシ樹脂6:エポキシ当量190g/eq、融点59℃、オルソクレゾールノボラック型エポキシ樹脂(DIC株式会社、商品名N−500P−1)
・硬化剤1:水酸基当量175g/eq、軟化点70℃のフェノールアラルキル樹脂(明和化成株式会社、商品名MEH−7800SS)
・硬化剤2:水酸基当量106g/eq、軟化点82℃のノボラック型フェノール樹脂(日立化成株式会社、商品名HP−850N)
・硬化促進剤1:トリフェニルホスフィンと1,4−ベンゾキノンの付加物
・エポキシシラン:γ−グリシドキシプロピルトリメトキシシラン
・球状溶融シリカ:平均粒径14.5μm、比表面積2.8m2/g
・カルナバワックス(クラリアント社)
・カーボンブラック(三菱化学株式会社、商品名MA−600)
EMMI−1−66に準じたスパイラルフロー測定用金型を用いて、エポキシ樹脂組成物をトランスファ成形機により、金型温度180℃、成形圧力6.9MPa、硬化時間90秒の条件で成形し、流動距離(cm)を求めた。
エポキシ樹脂組成物を上記(1)の成形条件で直径50mm×厚さ3mmの円板に成形し、成形後直ちにショアD型硬度計を用いて測定した。
厚さ1/32インチ(0.8mm)の試験片を成形する金型を用いて、エポキシ樹脂組成物を上記(1)の成形条件で成形して、更に180℃で5時間後硬化を行い、UL−94試験法に従って難燃性を評価した。
(4.1)Cuリードフレーム
8mm×10mm×0.4mmのシリコンチップを搭載した外形寸法20mm×14mm×2mmの80ピンフラットパッケージ(QFP)(リードフレーム材質:銅合金、ダイパッド部上面及びリード先端銀メッキ処理品)を、エポキシ樹脂組成物を用いて上記(3)の条件で成形、後硬化して作製し、85℃、85%RHの条件で加湿して所定時間経過したものを240℃、10秒の条件でリフロー処理を行い、クラックの有無を目視で観察し、試験パッケージ数(5個)に対するクラック発生パッケージ数で評価した。
リードフレームにPPF(コア材質:銅合金、三層(Ni/Pd/Au)メッキ処理品)を用いた以外は(4.1)と同様にして評価を実施した。
5μm厚の酸化ケイ素膜上に線幅10μm、厚さ1μmのアルミ配線を施した6mm×6mm×0.4mmのテスト用シリコンチップを搭載した外形寸法20mm×14mm×2.7mmの80ピンフラットパッケージ(QFP)を、エポキシ樹脂組成物を用いて上記(3)の条件で成形、後硬化して作製し、前処理を行った後、加湿して所定時間経過したものについてアルミ配線腐食による断線不良を調べ、試験パッケージ数(10個)に対する不良パッケージ数で評価した。
5μm厚の酸化ケイ素膜上に線幅10μm、厚さ1μmのアルミ配線を施した5mm×9mm×0.4mmのテスト用シリコンチップを、部分銀メッキを施した42アロイのリードフレーム上に銀ペーストを用いて搭載し、サーモニック型ワイヤボンダにより、200℃でチップのボンディングパッドとインナリードをAu線にて接続した16ピン型DIP(Dual Inline Package)を、エポキシ樹脂組成物を用いて上記(3)の条件で成形、後硬化して作製して、200℃の高温槽中に保管し、所定時間経過したものを取り出して導通試験を行い、試験パッケージ数(10個)に対する導通不良パッケージ数で、高温放置特性を評価した。
特定の硬化剤を用いない比較例1〜4では、実施例1〜4に比べてスパイラルフローが小さく、成型性に劣っていた。また、特定の硬化剤を用いる実施例1〜4に比べて、特定の硬化剤を用いない比較例1〜4では、Cuリードフレームにおける耐リフロー性(特に、72h及び96h)も若干劣っていた。
本明細書に記載された全ての文献、特許出願、及び技術規格は、個々の文献、特許出願、及び技術規格が参照により取り込まれることが具体的且つ個々に記された場合と同程度に、本明細書中に参照により取り込まれる。
Claims (8)
- 下記一般式(1)で示される化合物を含むエポキシ樹脂と、
ビフェニレン型フェノールアラルキル樹脂、フェノールアラルキル樹脂、及びトリフェニルメタン型フェノール樹脂からなる群より選択される少なくとも1種を含む硬化剤と、
を含有するエポキシ樹脂組成物。
〔R1は、各々独立に、水素原子又は炭素数1〜6の一価の炭化水素基を示し、R2は式(a)で示される置換基を示し、mは0〜20の数を示し、pは0.5〜2.0を示し、R3は、各々独立に、水素原子又は炭素数1〜6の一価の炭化水素基を示す。〕 - 更に、硬化促進剤を含有する請求項1に記載のエポキシ樹脂組成物。
- 前記硬化促進剤が、第三ホスフィン化合物とキノン化合物との付加物を含む請求項2に記載のエポキシ樹脂組成物。
- 更に、無機充填剤を含有する請求項1〜請求項3のいずれか1項に記載のエポキシ樹脂組成物。
- 前記無機充填剤の含有率が、60質量%〜95質量%である請求項4に記載のエポキシ樹脂組成物。
- 更に、カップリング剤を含有する請求項1〜請求項5のいずれか1項に記載のエポキシ樹脂組成物。
- 前記カップリング剤が、2級アミノ基を有するシランカップリング剤を含む請求項6に記載のエポキシ樹脂組成物。
- 素子と、
前記素子を封止する請求項1〜請求項7のいずれか1項に記載のエポキシ樹脂組成物の硬化物と、
を備える電子部品装置。
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WO2024128191A1 (ja) * | 2022-12-16 | 2024-06-20 | 株式会社レゾナック | 硬化性樹脂組成物及び電子部品装置 |
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JPH1025335A (ja) * | 1996-07-11 | 1998-01-27 | Hitachi Chem Co Ltd | 半導体素子用封止材及びそれを用いた半導体装置 |
JP2003064164A (ja) * | 2001-08-28 | 2003-03-05 | Sumikin Air Water Chemical Inc | フェノール系重合体、その製法及びその用途 |
WO2013125620A1 (ja) * | 2012-02-23 | 2013-08-29 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
WO2014073557A1 (ja) * | 2012-11-12 | 2014-05-15 | Dic株式会社 | フェノール性水酸基含有樹脂、エポキシ樹脂、硬化性樹脂組成物、その硬化物、及び半導体封止材料 |
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JPH0753791B2 (ja) | 1987-09-04 | 1995-06-07 | 東レ株式会社 | 半導体封止用樹脂組成物 |
JP3440449B2 (ja) | 1997-06-24 | 2003-08-25 | 京セラケミカル株式会社 | 封止用樹脂組成物および半導体封止装置 |
JP2000103940A (ja) | 1998-09-25 | 2000-04-11 | Toshiba Chem Corp | エポキシ樹脂組成物および半導体封止装置 |
JP3819220B2 (ja) | 2000-06-26 | 2006-09-06 | 京セラケミカル株式会社 | 封止用樹脂組成物および半導体封止装置 |
JP5906673B2 (ja) * | 2010-11-26 | 2016-04-20 | 日立化成株式会社 | 封止用エポキシ樹脂成形材料、及びこの成形材料で封止した素子を備えた電子部品装置 |
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JPH1025335A (ja) * | 1996-07-11 | 1998-01-27 | Hitachi Chem Co Ltd | 半導体素子用封止材及びそれを用いた半導体装置 |
JP2003064164A (ja) * | 2001-08-28 | 2003-03-05 | Sumikin Air Water Chemical Inc | フェノール系重合体、その製法及びその用途 |
WO2013125620A1 (ja) * | 2012-02-23 | 2013-08-29 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
WO2014073557A1 (ja) * | 2012-11-12 | 2014-05-15 | Dic株式会社 | フェノール性水酸基含有樹脂、エポキシ樹脂、硬化性樹脂組成物、その硬化物、及び半導体封止材料 |
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KR102127589B1 (ko) | 2020-06-26 |
TW201807057A (zh) | 2018-03-01 |
KR20180136494A (ko) | 2018-12-24 |
CN109071780B (zh) | 2022-04-08 |
CN109071780A (zh) | 2018-12-21 |
MY196654A (en) | 2023-04-27 |
PH12018502283A1 (en) | 2019-07-08 |
JP7343978B2 (ja) | 2023-09-13 |
SG11201809513UA (en) | 2018-11-29 |
TWI724162B (zh) | 2021-04-11 |
WO2017188455A1 (ja) | 2017-11-02 |
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