WO2018116757A1 - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
- Publication number
- WO2018116757A1 WO2018116757A1 PCT/JP2017/042549 JP2017042549W WO2018116757A1 WO 2018116757 A1 WO2018116757 A1 WO 2018116757A1 JP 2017042549 W JP2017042549 W JP 2017042549W WO 2018116757 A1 WO2018116757 A1 WO 2018116757A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- epoxy resin
- resin composition
- epoxy
- naphthalene
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 118
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 118
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000004593 Epoxy Substances 0.000 claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- -1 glycidyloxy group Chemical group 0.000 claims abstract description 67
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims description 122
- 239000011347 resin Substances 0.000 claims description 122
- 239000000463 material Substances 0.000 claims description 38
- 239000004065 semiconductor Substances 0.000 claims description 31
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 239000003566 sealing material Substances 0.000 claims description 22
- 239000012783 reinforcing fiber Substances 0.000 claims description 19
- 239000011888 foil Substances 0.000 claims description 17
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 14
- 125000005336 allyloxy group Chemical group 0.000 claims description 13
- 239000011256 inorganic filler Substances 0.000 claims description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 12
- 230000003014 reinforcing effect Effects 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
- 238000000465 moulding Methods 0.000 abstract description 13
- 125000004104 aryloxy group Chemical group 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 57
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 36
- 238000001723 curing Methods 0.000 description 34
- 239000004643 cyanate ester Substances 0.000 description 33
- 239000010410 layer Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 28
- 239000003063 flame retardant Substances 0.000 description 26
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- 150000001336 alkenes Chemical class 0.000 description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 19
- 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 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920003986 novolac Polymers 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000000835 fiber Substances 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000010030 laminating Methods 0.000 description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- 229920000877 Melamine resin Polymers 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 239000011889 copper foil Substances 0.000 description 6
- 239000005350 fused silica glass Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- 125000001302 tertiary amino group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000004917 carbon fiber Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 150000007973 cyanuric acids Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 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 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 3
- 238000001721 transfer moulding Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
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- 229940007718 zinc hydroxide Drugs 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
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- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 2
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910000416 bismuth oxide Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [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
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- MWSPFHZPVVWJCO-UHFFFAOYSA-M hydron;methyl(trioctyl)azanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC MWSPFHZPVVWJCO-UHFFFAOYSA-M 0.000 description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 description 2
- 229960001545 hydrotalcite Drugs 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 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
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- 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
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
- C08J5/08—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials glass fibres
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- 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
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- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- 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
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- C08K3/02—Elements
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- 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
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
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- 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
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- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
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- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/05—Insulated conductive substrates, e.g. insulated metal substrate
- H05K1/056—Insulated conductive substrates, e.g. insulated metal substrate the metal substrate being covered by an organic insulating layer
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/46—Manufacturing multilayer circuits
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- 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
- C08K3/02—Elements
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- C08K2003/0806—Silver
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- 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
- C08K3/02—Elements
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- C08K2003/085—Copper
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/001—Conductive additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
Definitions
- the present invention relates to an epoxy resin composition.
- the present invention also relates to a resin material, a semiconductor encapsulating material, a semiconductor device, a prepreg, a circuit board, a buildup film, a fiber reinforced composite material, and a fiber reinforced resin molded article using an epoxy resin composition.
- Epoxy resin compositions are used for adhesives, molding materials, paints, photoresist materials, developer materials, etc., and cured products have excellent heat resistance and moisture resistance. Widely used in the electrical and electronic fields.
- Patent Document 1 discloses a polyhydric glycidyl compound (A) having a glycidyl group and a glycidyl ether group bonded to the same aromatic ring in the molecule, and a phenolic curing having no substituent at the ortho position of the phenolic hydroxyl group.
- a curable resin composition containing an agent (B) is described.
- Patent Document 2 describes an alkoxysilyl-based epoxy compound having at least one alkoxysilyl group and at least two epoxy groups.
- This flip chip connection method is a so-called reflow method semiconductor mounting method in which solder balls are arranged between a wiring board and a semiconductor, and the whole is heated and melt bonded. For this reason, the wiring board itself is exposed to a high heat environment during solder reflow, warping occurs due to the thermal contraction of the wiring board, and a large stress is generated in the solder balls connecting the wiring board and the semiconductor, resulting in poor wiring connection. There was a case. In order to suppress such warpage of the wiring board, a sealing material having a high thermal elastic modulus and a high shrinkage rate is required as the sealing material.
- the reflow processing temperature is increased due to the shift to lead-free solder, and improvement of solder crack resistance (reflow resistance) is required.
- cured material is calculated
- One of the objects of the present invention is to provide an epoxy resin composition having an excellent balance of shrinkage ratio during curing molding, heat resistance of the cured product, and thermal elastic modulus of the cured product.
- Another object of the present invention is to provide a resin material, a semiconductor sealing material, a semiconductor device, a prepreg, a circuit board, a build-up film, a fiber-reinforced composite material using the above epoxy resin composition or a cured product thereof. And providing a fiber-reinforced resin molded article.
- One aspect of the present invention relates to an epoxy resin composition containing a naphthalene type epoxy compound and a curing agent for epoxy resin.
- the naphthalene-type epoxy compound contains a naphthalene ring, at least one group (A) selected from the group consisting of an allyl group and a glycidyl group directly bonded to the naphthalene ring, and the naphthalene ring directly.
- this epoxy resin composition contains a naphthalene type epoxy compound having a rigid naphthalene ring as a core structure, excellent heat resistance is imparted to the cured product. Moreover, since this naphthalene type epoxy compound has not only an epoxy-containing group (glycidyl group, glycidyloxy group) but also an olefin-containing group (allyl group, allyloxy group), only a crosslinking reaction between epoxy-containing groups. In addition, a crosslinked structure can be formed by a crosslinking reaction between olefin-containing groups, and a cured product having a complicated crosslinked structure can be formed.
- This complicated cross-linked structure is considered to increase the shrinkage rate of the epoxy resin composition during curing and the thermal elastic modulus of the cured product.
- the naphthalene type epoxy compound has a group (A) and a group (B) having different bonding modes to the naphthalene ring, and the cross-linking structure is further complicated by the difference in the bonding mode, and at the time of curing molding. It is considered that the shrinkage ratio and the thermal modulus of the cured product are further improved.
- the naphthalene type epoxy compound may have both the glycidyl group and the glycidyloxy group.
- the group (A) may be bonded to a position adjacent to the group (B) of the naphthalene ring.
- Another aspect of the present invention relates to a resin material containing a cured product of the above epoxy resin composition.
- Still another aspect of the present invention relates to a semiconductor sealing material containing the epoxy resin composition, wherein the epoxy resin composition further contains an inorganic filler.
- Still another aspect of the present invention relates to a semiconductor device including a sealing material containing a cured product of the semiconductor sealing material.
- Still another aspect of the present invention relates to a prepreg that is a semi-cured product of an impregnated base material containing a reinforcing base material and the epoxy resin composition impregnated in the reinforcing base material.
- Still another aspect of the present invention relates to a circuit board comprising a metal foil and a cured resin layer containing a cured product of the epoxy resin composition provided on the metal foil.
- Still another aspect of the present invention relates to a buildup film containing the above epoxy resin composition.
- Still another aspect of the present invention relates to a fiber-reinforced composite material containing a cured product of the above epoxy resin composition and reinforcing fibers.
- Still another aspect of the present invention relates to a conductive paste containing the epoxy resin composition and conductive particles.
- an epoxy resin composition having an excellent balance of shrinkage ratio during curing molding, heat resistance of a cured product, and thermal elastic modulus of the cured product.
- the epoxy resin composition according to the present embodiment contains a naphthalene type epoxy compound and an epoxy resin curing agent.
- the naphthalene type epoxy compound includes a naphthalene ring, at least one group (A) selected from the group consisting of an allyl group and a glycidyl group directly bonded to the naphthalene ring, and an allyloxy group directly bonded to the naphthalene ring. And at least one group (B) selected from the group consisting of glycidyloxy groups.
- the naphthalene-type epoxy compound includes at least one epoxy-containing group selected from the group consisting of a glycidyl group and a glycidyloxy group directly bonded to the naphthalene ring, and an allyl group and an allyloxy group directly bonded to the naphthalene ring. And at least one olefin-containing group selected.
- the epoxy resin composition according to the present embodiment contains a naphthalene type epoxy compound having a rigid naphthalene ring as a core structure, the cured product is excellent in heat resistance.
- this naphthalene type epoxy compound has not only an epoxy-containing group but also an olefin-containing group, a crosslinked structure is formed not only by a crosslinking reaction between epoxy-containing groups but also by a crosslinking reaction between olefin-containing groups.
- a cured product having a complicated cross-linked structure can be formed. This complicated cross-linked structure is considered to increase the shrinkage rate of the epoxy resin composition during curing and the thermal elastic modulus of the cured product.
- the naphthalene type epoxy compound has a group (A) and a group (B) having different bonding modes to the naphthalene ring, and the cross-linking structure is further complicated due to the difference in the bonding mode, and at the time of curing molding. It is considered that the shrinkage rate and the thermal modulus of the cured product are further improved.
- the naphthalene type epoxy compound includes a naphthalene ring, at least one group (A) selected from the group consisting of an allyl group and a glycidyl group directly bonded to the naphthalene ring, and an allyloxy group and a glycidyloxy group directly bonded to the naphthalene ring. And at least one group (B) selected from the group consisting of: The group (A) is bonded to the naphthalene ring with a carbon atom, and the group (B) is bonded to the naphthalene ring with an oxygen atom.
- the allyl group is a group represented by the following formula (1-1), and the allyloxy group is a group represented by the following formula (1-2).
- the wavy line in the formulas (1-1) and (1-2) means that it is directly bonded to the naphthalene ring.
- the glycidyl group is a group in which the olefin portion of the allyl group is epoxidized
- the glycidyloxy group is a group in which the olefin portion of the allyloxy group is epoxidized.
- the naphthalene type epoxy compound at least one of the group (A) and the group (B) is at least one epoxy-containing group selected from the group consisting of a glycidyl group and a glycidyloxy group.
- the naphthalene type epoxy compound has a function of curing the epoxy resin composition by a reaction between the epoxy-containing group and the epoxy resin curing agent.
- the naphthalene type epoxy compound at least one of the group (A) and the group (B) is at least one olefin-containing group selected from the group consisting of an allyl group and an allyloxy group. Since the naphthalene type epoxy compound has not only an epoxy-containing group but also an olefin-containing group, a cured product having a complicated cross-linked structure can be formed.
- the naphthalene type epoxy compound may be a kind of compound having the above characteristics, or may be a mixture of plural kinds of compounds.
- the ratio C 2 / C 1 + 2 of the total number C 2 of olefin-containing groups to the total number C 1 + 2 of epoxy-containing groups and olefin-containing groups may be, for example, 0.1 or more, preferably 0 .2 or more, for example, 0.9 or less, preferably 0.8 or less.
- Increasing the ratio C 2 / C 1 + 2 tends to increase the shrinkage rate at the time of curing molding and the thermal modulus of the cured product, and decreasing the ratio C 2 / C 1 + 2 reduces the glass transition temperature of the cured product. Tend to be higher.
- the naphthalene type epoxy compound it is preferable that at least one of the groups (A) is a glycidyl group and at least one of the groups (B) is a glycidyloxy group. That is, the naphthalene type epoxy compound preferably has a glycidyl group and a glycidyloxy group that are directly bonded to the naphthalene ring. Such a naphthalene type epoxy compound has an epoxy-containing group having a different bonding mode to the naphthalene ring, and can form a complicated cross-linked structure resulting from this bonding mode.
- the group (A) is preferably bonded to a position adjacent to the group (B) of the naphthalene ring.
- the group (A) when the group (B) is bonded to the 1-position of the naphthalene ring, the group (A) is preferably bonded to the 2-position of the naphthalene ring.
- the group (A) when the group (B) is bonded to the 2-position of the naphthalene ring, the group (A) is preferably bonded to the 1- or 3-position of the naphthalene ring, and preferably bonded to the 1-position. More preferred.
- Such a naphthalene type epoxy compound is excellent in productivity because the raw material compound can be easily synthesized by the method described in Synlett, 2006, 14, 2211.
- the naphthalene type epoxy compound has two or more groups (A) in the molecule.
- the number of groups (A) is preferably 2 to 4, more preferably 2 to 3.
- the naphthalene type epoxy compound has two or more groups (B) in the molecule.
- the number of groups (B) is preferably 2 to 4, more preferably 2 to 3.
- the naphthalene type epoxy compound preferably has two or more epoxy-containing groups in the molecule.
- the number of epoxy-containing groups is preferably 2 to 4, more preferably 2 to 3.
- the naphthalene ring of the naphthalene type epoxy compound may be condensed with another ring.
- a group other than the groups (A) and (B) (hereinafter also referred to as other groups) may be further bonded to the naphthalene ring of the naphthalene type epoxy compound.
- Other groups should just be groups which do not inhibit hardening of an epoxy resin composition.
- Examples of other groups include halogeno groups (for example, fluoro groups, chloro groups, bromo groups, iodo groups, etc.), alkoxy groups (for example, alkoxy groups having 1 to 10 carbon atoms), aryloxy groups (for example, carbon numbers) 6-10 aryloxy groups), acyl groups (eg, acyl groups having 1-10 carbon atoms), acyloxy groups (eg, acyloxy groups having 1-10 carbon atoms), hydrocarbon groups (eg, 1-20 carbon atoms). Hydrocarbon group) and the like.
- halogeno groups for example, fluoro groups, chloro groups, bromo groups, iodo groups, etc.
- alkoxy groups for example, alkoxy groups having 1 to 10 carbon atoms
- aryloxy groups for example, carbon numbers 6-10 aryloxy groups
- acyl groups eg, acyl groups having 1-10 carbon atoms
- acyloxy groups eg, acyloxy groups having
- some or all of the hydrogen atoms of the group may be substituted with a halogeno group, and a secondary amino group, a tertiary amino group, an oxy group, and a carbonyl group are contained inside the group. At least one selected from the group consisting of groups may be inserted.
- At least one selected from the group consisting of a secondary amino group, a tertiary amino group, an oxy group and a carbonyl group may be inserted” means that a C—C bond or C Between the —H bond, a secondary or tertiary amino group (—NR—), an oxy group (—O—), a carbonyl group (—C ( ⁇ O) —), an amide group (— It means that C ( ⁇ O) NR—), oxycarbonyl group (—OC ( ⁇ O) —) or the like may be inserted.
- alkoxy group examples include a methoxy group, an ethoxy group, and a t-butoxy group.
- examples of the group in which at least one selected from the group consisting of a secondary amino group, a tertiary amino group, an oxy group, and a carbonyl group is inserted in the alkoxy group include, for example, a methoxyethoxy group, methylcarboxyl group, and the like. Group, ethylcarboxy group and the like.
- aryloxy group examples include a phenoxy group and a tolyloxy group.
- group in which at least one selected from the group consisting of a secondary amino group, a tertiary amino group, an oxy group, and a carbonyl group is inserted in the aryloxy group include, for example, a methoxyphenoxy group, an ethoxyphenoxy group , T-butoxyphenoxy group and the like.
- acyl group examples include an acetyl group, a propionyl group, and a benzoyl group.
- acyloxy group examples include an acetyloxy group, a propionyloxy group, and a benzoyloxy group.
- the hydrocarbon group examples include a saturated hydrocarbon group and an unsaturated hydrocarbon group.
- the saturated hydrocarbon group and the unsaturated hydrocarbon group may be linear, branched or cyclic, respectively. That is, the hydrocarbon group includes an alkyl group (for example, methyl group, t-butyl group, n-hexyl group, etc.), a cycloalkyl group (for example, cyclohexyl group, etc.), an alkynyl group (for example, ethynyl group, propynyl group, etc.).
- an alkyl group for example, methyl group, t-butyl group, n-hexyl group, etc.
- a cycloalkyl group for example, cyclohexyl group, etc.
- an alkynyl group for example, ethynyl group, propynyl group, etc.
- An alkenyl group eg, ethenyl group, propenyl group, etc.
- an aryl group eg, phenyl group, benzyl group, tolyl group, etc.
- Examples of the group in which at least one selected from the group consisting of a secondary amino group, a tertiary amino group, an oxy group and a carbonyl group is inserted in the hydrocarbon group include, for example, a methoxymethyl group, 2-methoxy group An ethoxymethyl group etc. are mentioned.
- R 1 represents a group other than the group (A) and the group (B).
- J represents an integer of 0 to 6
- k, l, m and n each independently represents an integer of 0 to 7, j + k + l + m + n is 2 or more and 8 or less, k + m is 1 or more and 7 or less, and l + n Is from 1 to 7, k + 1 is from 1 to 7, and m + n is from 1 to 7.
- K and l are each preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 or 2. Further, at least one of k and l is preferably 2, and the other is more preferably 1 or 2. Further, k + m is preferably 2 to 4, more preferably 2 to 3, and still more preferably 2. L + n is preferably 2 to 4, more preferably 2 to 3, and still more preferably 2.
- naphthalene type epoxy compounds include 1-glycidyloxy-5-allyloxy-2,6-diglycidylnaphthalene, 1-glycidyloxy-5-allyloxy-2-glycidyl-6-allylnaphthalene, 1-glycidyloxy- Examples include 5-allyloxy-2,6-diallylnaphthalene and 1,5-diallyloxy-2,6-diglycidylnaphthalene.
- the production method of the naphthalene type epoxy compound is not particularly limited.
- a naphthalene type epoxy is prepared by preparing a raw material compound having a naphthalene ring and an allyl group and an allyloxy group directly bonded to the naphthalene ring, and epoxidizing a part of the allyl group and the allyloxy group in the raw material compound.
- Compounds can be produced.
- the content of the naphthalene type epoxy compound in the epoxy resin composition may be, for example, 10% by mass or more, preferably 20% by mass or more, and more preferably 30% by mass or more.
- the curing agent for epoxy resin is not particularly limited as long as it is a component capable of crosslinking the epoxy-containing groups of the naphthalene type epoxy compound.
- curing agent for epoxy resins examples include various known curing agents such as amine compounds, amide compounds, acid anhydride compounds, phenol compounds, and the like.
- examples of the amine compound include diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, imidazole, BF 3 -amine complex, and guanidine derivative.
- examples of the amide compounds include polyamide resins synthesized from dimer of dicyandiamide and linolenic acid and ethylenediamine.
- acid anhydride compounds include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, methyl And hexahydrophthalic anhydride.
- the phenolic compounds include phenol novolac resin, cresol novolac resin, aromatic hydrocarbon formaldehyde resin modified phenol resin, dicyclopentadiene phenol addition type resin, phenol aralkyl resin (Zylok resin), naphthol aralkyl resin, triphenylol methane.
- Resin tetraphenylolethane resin, naphthol novolak resin, naphthol-phenol co-condensed novolak resin, naphthol-cresol co-condensed novolak resin, biphenyl-modified phenol resin (polyphenolic hydroxyl group-containing compound in which phenol nuclei are linked by bismethylene groups) , Biphenyl-modified naphthol resins (polyvalent naphthol compounds in which phenol nuclei are linked by bismethylene groups), aminotriazine-modified phenol resins (melamine, Polyphenolic hydroxyl group-containing compounds in which phenol nuclei are linked with nzoguanamine, etc., alkoxy group-containing aromatic ring-modified novolak resins (polyphenolic hydroxyl group-containing compounds in which phenol nuclei and alkoxy group-containing aromatic rings are linked with formaldehyde), etc. And a polyhydric phenolic hydroxyl group-containing compound.
- the content of the curing agent for epoxy resin in the epoxy resin composition may be, for example, 0.001% by mass or more, preferably 0.01% by mass or more, and more preferably 0.1% by mass or more. Is more preferable.
- curing agent for epoxy resins in an epoxy resin composition may be 90 mass% or less, for example, it is preferable that it is 80 mass% or less, and it is more preferable that it is 70 mass% or less.
- the epoxy resin composition may further contain components other than the naphthalene type epoxy compound and the epoxy resin curing agent.
- the epoxy resin composition may further contain a thermosetting resin other than the naphthalene type epoxy compound.
- thermosetting resin examples include a cyanate ester resin, a resin having a benzoxazine structure, a maleimide compound, an active ester resin, a vinyl benzyl compound, an acrylic compound, and a copolymer of styrene and maleic anhydride.
- the amount used is not particularly limited as long as the above-described effects are not impaired, and for example, it is preferably less than 50% by mass based on the total amount of the epoxy resin composition. .
- cyanate ester resin examples include bisphenol A type cyanate ester resin, bisphenol F type cyanate ester resin, bisphenol E type cyanate ester resin, bisphenol S type cyanate ester resin, bisphenol sulfide type cyanate ester resin, phenylene ether type cyanate ester resin, Naphthylene ether type cyanate ester resin, biphenyl type cyanate ester resin, tetramethylbiphenyl type cyanate ester resin, polyhydroxynaphthalene type cyanate ester resin, phenol novolac type cyanate ester resin, cresol novolac type cyanate ester resin, triphenylmethane type cyanate ester Resin, tetraphenylethane type cyanate ester resin, di Clopentadiene-phenol addition reaction type cyanate ester resin, phenol aralkyl type cyanate ester resin, naphthol novolak type cyanate ester resin, napht
- cyanate ester resins bisphenol A-type cyanate ester resins, bisphenol F-type cyanate ester resins, bisphenol E-type cyanate ester resins, and polyhydroxynaphthalene-type cyanate ester resins are particularly preferred in that a cured product having excellent heat resistance can be obtained.
- a naphthylene ether type cyanate ester resin or a novolak type cyanate ester resin is preferably used, and a dicyclopentadiene-phenol addition reaction type cyanate ester resin is preferred in that a cured product having excellent dielectric properties can be obtained.
- the resin having a benzoxazine structure is not particularly limited.
- a reaction product of bisphenol F, formalin, and aniline (Fa type benzoxazine resin), a reaction product of diaminodiphenylmethane, formalin, and phenol (P— d-type benzoxazine resin), reaction product of bisphenol A, formalin and aniline, reaction product of dihydroxydiphenyl ether, formalin and aniline, reaction product of diaminodiphenyl ether, formalin and phenol, dicyclopentadiene-phenol addition resin and formalin Reaction product of phenol and aniline, reaction product of phenolphthalein, formalin and aniline, reaction product of diphenyl sulfide, formalin and aniline.
- Fa type benzoxazine resin a reaction product of bisphenol F, formalin, and aniline
- P— d-type benzoxazine resin reaction product of bisphenol A, formalin and aniline
- maleimide compounds include compounds represented by the following formulas (i) to (iii).
- a maleimide compound may be used individually by 1 type, and may use 2 or more types together.
- R represents an s-valent organic group
- ⁇ and ⁇ each independently represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group, and s represents an integer of 1 or more.
- R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group or an alkoxy group, s represents an integer of 1 to 3, and t represents an average of 0 to 10 repeating units. It is.
- R represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group or an alkoxy group, s represents an integer of 1 to 3, and t represents an average of 0 to 10 repeating units. It is.
- the active ester resin is not particularly limited, but generally an ester group having high reaction activity, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, is contained in one molecule.
- a compound having two or more is preferably used.
- the active ester resin is preferably one obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound.
- an active ester resin obtained from a carboxylic acid compound or a halide thereof and a hydroxy compound is preferred, and an active ester resin obtained from a carboxylic acid compound or a halide thereof and a phenol compound and / or a naphthol compound is preferred. More preferred.
- the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and the like, or a halide thereof.
- phenol compounds or naphthol compounds include hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, dihydroxydiphenyl ether, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m -Cresol, p-cresol, catechol, ⁇ -naphthol, ⁇ -naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin Benzenetriol, dicyclopentadiene-phenol addition resin, and the like.
- the active ester resin examples include an active ester resin containing a dicyclopentadiene-phenol addition structure, an active ester resin containing a naphthalene structure, an active ester resin that is an acetylated product of phenol novolac, and a benzoylated product of phenol novolac.
- An active ester resin or the like is preferable, and among them, an active ester resin including a dicyclopentadiene-phenol addition structure and an active ester resin including a naphthalene structure are more preferable in terms of excellent peel strength. More specifically, examples of the active ester resin containing a dicyclopentadiene-phenol addition structure include compounds represented by the following general formula (iv).
- R represents a phenyl group or a naphthyl group
- u represents 0 or 1
- n represents 0.05 to 2.5 on the average of repeating units.
- R is preferably a naphthyl group
- u is preferably 0, and n is from 0.25 to 1.5. preferable.
- the epoxy resin composition according to this embodiment is cured only with a naphthalene type epoxy compound and a curing agent for epoxy resin, but a curing accelerator may be used in combination.
- Curing accelerators include tertiary amine compounds such as imidazole and dimethylaminopyridine; phosphorus compounds such as triphenylphosphine; boron trifluoride amine complexes such as boron trifluoride and boron trifluoride monoethylamine complexes; thiodipropion Organic acid compounds such as acids; benzoxazine compounds such as thiodiphenol benzoxazine and sulfonyl benzoxazine; sulfonyl compounds and the like. These may be used alone or in combination of two or more.
- the amount of these catalysts is preferably in the range of 0.001 to 15% by mass based on the total amount of the epoxy resin composition.
- the epoxy resin composition according to this embodiment may contain a flame retardant for the purpose of obtaining high flame retardancy. Thereby, it uses suitably for the use as which high flame retardance is calculated
- a flame retardant a non-halogen flame retardant containing substantially no halogen atom is preferable.
- non-halogen flame retardants include phosphorus flame retardants, nitrogen flame retardants, silicone flame retardants, inorganic flame retardants, and organic metal salt flame retardants. These may be used alone or a plurality of flame retardants of the same system may be used, or different types of flame retardants may be used in combination.
- the phosphorous flame retardant can be either inorganic or organic.
- the inorganic compounds include red phosphorus, monoammonium phosphate, diammonium phosphate, triammonium phosphate, ammonium phosphates such as ammonium polyphosphate, and inorganic nitrogen-containing phosphorus compounds such as phosphate amide. .
- Red phosphorus is preferably subjected to surface treatment for the purpose of preventing hydrolysis and the like
- examples of the surface treatment method include (i) magnesium hydroxide, aluminum hydroxide, zinc hydroxide, titanium hydroxide, A method of coating with an inorganic compound such as bismuth oxide, bismuth hydroxide, bismuth nitrate, or a mixture thereof; (ii) inorganic compounds such as magnesium hydroxide, aluminum hydroxide, zinc hydroxide, titanium hydroxide; and phenol resins (Iii) A coating of an inorganic compound such as magnesium hydroxide, aluminum hydroxide, zinc hydroxide, or titanium hydroxide with a thermosetting resin such as a phenol resin. Examples of the method include heavy coating treatment.
- Organic phosphorus compounds include, for example, general-purpose organic phosphorus compounds such as phosphate ester compounds, phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphorane compounds, organic nitrogen-containing phosphorus compounds, and 9,10-dihydro- 9-oxa-10-phosphaphenanthrene-10-oxide, 10- (2,5-dihydrooxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (2,7-dihydro And cyclic organic phosphorus compounds such as oxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide and derivatives obtained by reacting them with compounds such as epoxy resins and phenol resins.
- general-purpose organic phosphorus compounds such as phosphate ester compounds, phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphorane compounds, organic nitrogen-containing phosphorus
- the compounding amount of the phosphorus-based flame retardant is appropriately selected depending on the type of the phosphorus-based flame retardant, the other components of the epoxy resin composition, the desired degree of flame retardancy, and the like.
- red phosphorus is used as a non-halogen flame retardant, it is preferably blended in the range of 0.1 to 2.0% by mass on the basis of the total amount. It is preferably blended in the range of 10.0% by mass, and more preferably in the range of 0.5 to 6.0% by mass.
- hydrotalcite magnesium hydroxide
- boron compound boron compound
- zirconium oxide black dye
- calcium carbonate calcium carbonate
- zeolite zinc molybdate, activated carbon, etc.
- activated carbon etc.
- nitrogen-based flame retardants include triazine compounds, cyanuric acid compounds, isocyanuric acid compounds, phenothiazines, and the like, and triazine compounds, cyanuric acid compounds, and isocyanuric acid compounds are preferable.
- triazine compound examples include melamine, acetoguanamine, benzoguanamine, melon, melam, succinoguanamine, ethylene dimelamine, melamine polyphosphate, triguanamine, and the like, for example, (1) guanylmelamine sulfate, melem sulfate, melam sulfate (2) Cocondensates of phenols such as phenol, cresol, xylenol, butylphenol and nonylphenol with melamines such as melamine, benzoguanamine, acetoguanamine and formguanamine and formaldehyde, (3) (2) A mixture of a co-condensate and a phenol resin such as a phenol formaldehyde condensate, (4) those obtained by further modifying (2) or (3) above with paulownia oil, isomerized linseed oil, or the like.
- Examples of the cyanuric acid compound include cyanuric acid and cyanuric acid melamine.
- the amount of the nitrogen-based flame retardant is appropriately selected depending on the type of the nitrogen-based flame retardant, the other components of the epoxy resin composition, the desired degree of flame retardancy, and the like.
- the epoxy resin composition Is preferably blended in the range of 0.05 to 10% by mass, more preferably in the range of 0.1 to 5% by mass.
- a metal hydroxide, a molybdenum compound, or the like may be used in combination.
- the silicone flame retardant is not particularly limited as long as it is an organic compound containing a silicon atom, and examples thereof include silicone oil, silicone rubber, and silicone resin.
- the compounding amount of the silicone flame retardant is appropriately selected depending on the type of the silicone flame retardant, the other components of the epoxy resin composition, the desired degree of flame retardancy, and the like.
- the epoxy resin composition It is preferable to blend in the range of 0.05 to 20% by mass on the basis of the total amount.
- inorganic flame retardant examples include metal hydroxide, metal oxide, metal carbonate compound, metal powder, boron compound, and low melting point glass.
- metal hydroxide examples include aluminum hydroxide, magnesium hydroxide, dolomite, hydrotalcite, calcium hydroxide, barium hydroxide, and zirconium hydroxide.
- metal oxide examples include zinc molybdate, molybdenum trioxide, zinc stannate, tin oxide, aluminum oxide, iron oxide, titanium oxide, manganese oxide, zirconium oxide, zinc oxide, molybdenum oxide, cobalt oxide, bismuth oxide, Examples thereof include chromium oxide, nickel oxide, copper oxide, and tungsten oxide.
- metal carbonate compound examples include zinc carbonate, magnesium carbonate, calcium carbonate, barium carbonate, basic magnesium carbonate, aluminum carbonate, iron carbonate, cobalt carbonate, and titanium carbonate.
- metal powder examples include aluminum, iron, titanium, manganese, zinc, molybdenum, cobalt, bismuth, chromium, nickel, copper, tungsten, and tin.
- Examples of the boron compound include zinc borate, zinc metaborate, barium metaborate, boric acid, and borax.
- low-melting-point glass examples include Shipley (Bokusui Brown), hydrated glass SiO 2 —MgO—H 2 O, PbO—B 2 O 3 system, ZnO—P 2 O 5 —MgO system, P 2 O 5 — Glassy compounds such as B 2 O 3 —PbO—MgO, P—Sn—O—F, PbO—V 2 O 5 —TeO 2 , Al 2 O 3 —H 2 O, lead borosilicate, etc. Can be mentioned.
- the compounding amount of the inorganic flame retardant is appropriately selected according to the type of the inorganic flame retardant, the other components of the epoxy resin composition, the desired degree of flame retardancy, etc.
- the total amount is preferably 0.05 to 20% by mass, more preferably 0.5 to 15% by mass.
- Organic metal salt flame retardants include, for example, ferrocene, acetylacetonate metal complexes, organometallic carbonyl compounds, organocobalt salt compounds, organosulfonic acid metal salts, metal atoms and aromatic compounds or heterocyclic compounds in ionic bonds or coordination. Examples include a bonded compound.
- the amount of the organic metal salt flame retardant is appropriately selected according to the type of the organic metal salt flame retardant, the other components of the epoxy resin composition, the desired degree of flame retardancy, etc. It is preferable to blend in the range of 0.005 to 10% by mass based on the total amount of the resin composition.
- an inorganic filler may be blended as necessary.
- the inorganic filler include fused silica, crystalline silica, alumina, silicon nitride, and aluminum hydroxide.
- fused silica When the blending amount of the inorganic filler is particularly large, it is preferable to use fused silica.
- the fused silica can be used in either a crushed shape or a spherical shape. However, in order to increase the blending amount of the fused silica and suppress an increase in the melt viscosity of the molding material, it is preferable to mainly use a spherical shape.
- the filling rate is preferably high, and particularly preferably 20% by mass or more based on the total amount of the epoxy resin composition (including the inorganic filler). Moreover, the filling rate of an inorganic filler may be 95 mass% or less on the basis of the total amount of an epoxy resin composition, for example. Moreover, when using for uses, such as an electrically conductive paste, electroconductive fillers, such as silver powder and copper powder, can be used.
- various compounding agents such as a silane coupling agent, a mold release agent, a pigment, and an emulsifier, can be added to the epoxy resin composition as necessary.
- the epoxy resin composition according to the present embodiment is excellent in the shrinkage rate at the time of curing and molding, the heat resistance of the cured product, and the thermal modulus of the cured product. For this reason, the epoxy resin composition, the cured product of the epoxy resin composition, and the resin material containing the cured product can be suitably used for various applications.
- the epoxy resin composition is made of a semiconductor sealing material, a semiconductor device, a prepreg, a circuit board (printed circuit board, build-up board, etc.), a build-up film, a fiber-reinforced composite material, and a fiber-reinforced resin molded product. It can be applied to a conductive paste or the like.
- the semiconductor sealing material which concerns on this embodiment contains the above-mentioned epoxy resin composition.
- the epoxy resin composition contains an inorganic filler and may further contain other compounding agents.
- the semiconductor sealing material is obtained by, for example, melt-mixing a naphthalene type epoxy compound, a curing agent for epoxy resin, and an inorganic filler (if necessary, other compounding agents) using an extruder, kneader, roll, or the like. May be prepared.
- the inorganic filler usually fused silica is used. Further, when used as a high thermal conductive semiconductor encapsulant used in power transistors, power ICs, etc., it may be highly filled using crystalline silica, alumina, silicon nitride or the like having higher thermal conductivity.
- the filling rate of the inorganic filler is preferably, for example, 30 to 95 parts by mass with respect to 100 parts by mass of the epoxy resin composition. Moreover, from the viewpoint of improving flame retardancy, moisture resistance and solder crack resistance, and reducing the linear expansion coefficient, the filling rate of the inorganic filler is 70 parts by mass with respect to 100 parts by mass of the epoxy resin composition. The above is more preferable, and 80 parts by mass or more is more preferable.
- a semiconductor device includes a sealing material containing a cured product of the above-described semiconductor sealing material.
- the method for forming the sealing material is not particularly limited.
- the semiconductor sealing material is molded using a casting molding machine, a transfer molding machine, an injection molding machine, etc., and is at 50 to 200 ° C. for 2 to 10 hours. And a method of heating.
- the configuration of the semiconductor device other than the sealing material is not particularly limited, and may be a known configuration. That is, the semiconductor device according to this embodiment may be obtained by replacing the sealing material in a known semiconductor device with the above-described sealing material.
- the prepreg according to the present embodiment is a semi-cured product of an impregnated base material containing a reinforcing base material and the above-described epoxy resin composition impregnated in the reinforcing base material.
- the method for producing the prepreg is not particularly limited.
- an epoxy resin composition that has been varnished with an organic solvent is used as a reinforcing substrate (paper, glass cloth, glass nonwoven fabric, aramid paper, aramid cloth, glass mat, glass roving). And a method of heating at a heating temperature (for example, 50 to 170 ° C.) according to the solvent type used.
- the ratio of the epoxy resin composition and the reinforcing base material is not particularly limited, but it is preferable to adjust so that, for example, the resin content in the prepreg is 20 to 60% by mass.
- organic solvent used here examples include methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, methoxypropanol, cyclohexanone, methyl cellosolve, ethyl diglycol acetate, propylene glycol monomethyl ether acetate, and the like.
- the kind and amount of the organic solvent can be appropriately selected depending on the application. For example, when a printed circuit board is produced from a prepreg, it is preferable to use a polar solvent having a boiling point of 160 ° C. or lower, such as methyl ethyl ketone, acetone, dimethylformamide, and the nonvolatile content is 40% by mass to 80% by mass. It is preferable to use in proportion.
- Circuit board The circuit board concerning this embodiment is provided with metal foil and the cured resin layer provided on metal foil, and the cured resin layer contains the hardened material of the above-mentioned epoxy resin composition.
- Specific examples of the circuit board according to the present embodiment include a printed circuit board and a build-up board.
- a printed circuit board according to the present embodiment includes a metal foil and a cured resin layer provided on the metal foil.
- the cured resin layer may be composed of a cured product of the prepreg described above. That is, the cured resin layer may include a cured product of the epoxy resin composition and a reinforcing substrate.
- metal foil copper foil is mentioned, for example, and copper foil is preferable.
- the printed circuit board according to the present embodiment is not particularly limited in the configuration other than the above, and may further include, for example, a configuration included in a known printed circuit board.
- the manufacturing method of the printed circuit board is not particularly limited.
- the method for producing a printed circuit board may include a step of laminating the above-described prepreg and copper foil and thermocompression bonding at 170 to 300 ° C. for 10 minutes to 3 hours under a pressure of 1 to 10 MPa.
- the build-up substrate according to the present embodiment includes a metal foil and a cured resin layer provided on the metal foil, and the cured resin layer includes a cured product of the above-described epoxy resin composition. Yes.
- metal foil copper foil is mentioned, for example, and copper foil is preferable.
- the build-up substrate according to the present embodiment is not particularly limited in the configuration other than the above, and may further include, for example, a configuration included in a known build-up substrate.
- the manufacturing method of the build-up board is not particularly limited.
- the method for manufacturing a build-up substrate may include the following steps 1 to 3.
- step 1 first, the above-described epoxy resin composition appropriately blended with rubber, filler or the like is applied to a circuit board using a spray coating method, a curtain coating method, or the like, and then cured.
- step 1 a cured resin layer containing a cured product of the epoxy resin composition is formed on the circuit board.
- the circuit board on which the epoxy resin composition has been applied is subjected to drilling, such as predetermined through-hole portions, as necessary, then treated with a roughening agent, and the surface is made uneven by washing with hot water. Forming and plating a metal such as copper.
- step 2 a metal foil is formed on the cured resin layer.
- step 3 the operations of step 1 and step 2 are sequentially repeated as desired, and a resin insulating layer (cured resin layer) and a conductor layer having a predetermined circuit pattern are alternately built up to form a build-up substrate. .
- the through-hole portion is formed after, for example, the outermost resin insulating layer is formed.
- a resin-coated metal foil obtained by semi-curing an epoxy resin composition on a metal foil is heat-pressed on a circuit board at 170 to 300 ° C. A roughened surface may be formed. This eliminates the plating process.
- the build-up film according to the present embodiment contains the above-described epoxy resin composition.
- the buildup film according to the present embodiment may include a base film and a resin layer containing the above-described epoxy resin composition provided on the base film.
- the buildup film may further include a protective film on the surface of the resin layer opposite to the base film.
- the build-up film is softened under the lamination temperature conditions (usually 70 to 140 ° C.) in the vacuum laminating method, and has a fluidity that allows resin filling in the via hole or through hole of the circuit board when laminating to the circuit board ( It is important to show the resin flow), and it is preferable that the epoxy resin composition contains each component so as to exhibit such characteristics.
- the diameter of the through hole of the circuit board is usually 0.1 to 0.5 mm, and the depth is usually 0.1 to 1.2 mm, and the build-up film can fill such a through hole with a resin. It is preferable. In addition, when laminating on both surfaces of the circuit board, it may be filled up to about 1/2 the depth of the through hole.
- the manufacturing method of the build-up film is not particularly limited.
- a method for producing a build-up film there is a method in which an epoxy resin composition is applied on a base film and then dried to form a resin layer.
- the epoxy resin composition may be formed into a varnish by blending an organic solvent and applied onto the base film.
- the organic solvent can be dried by heating, hot air blowing, or the like.
- organic solvent examples include ketones such as acetone, methyl ethyl ketone and cyclohexanone, acetates such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, and carbitols such as cellosolve and butyl carbitol.
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- acetates such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate
- carbitols such as cellosolve and butyl carbitol.
- Aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc. are preferably used, and the
- the thickness of the resin layer usually needs to be equal to or greater than the thickness of the conductor layer of the circuit board. Since the thickness of the conductor layer of the circuit board is usually in the range of 5 to 70 ⁇ m, the resin layer preferably has a thickness of 10 to 100 ⁇ m.
- the resin layer may be protected with a protective film.
- a protective film By protecting with a protective film, it is possible to prevent dust from adhering to the surface of the resin layer and scratches.
- the base film and the protective film are resin films such as polyolefins such as polyethylene, polypropylene, and polyvinyl chloride, polyethylene terephthalate (hereinafter sometimes abbreviated as “PET”), polyesters such as polyethylene naphthalate, polycarbonate, and polyimide. It may be. Further, the base film and the protective film may be release paper, metal foil (for example, copper foil, aluminum foil, etc.) and the like. The base film and the protective film may be subjected to a surface treatment such as a mud treatment, a corona treatment, or a mold release treatment.
- the thickness of the support film is not particularly limited, but is usually 10 to 150 ⁇ m, preferably 25 to 50 ⁇ m.
- the thickness of the protective film is not particularly limited, but is preferably 1 to 40 ⁇ m.
- the base film may be peeled after the build-up film is laminated on the circuit board or after the resin layer is cured by heat curing to form a resin insulating layer. If the base film is peeled after the resin layer of the build-up film is heated and cured, adhesion of dust and the like in the curing process can be prevented. When peeling a base film after hardening of a resin layer, it is preferable that a mold release process is given to the base film beforehand.
- the use of the build-up film is not limited, and can be used, for example, for manufacturing a multilayer printed circuit board.
- the build-up film is peeled off and then laminated on one or both sides of the circuit board so that the resin layer is in direct contact with the circuit board.
- Lamination can be performed by, for example, a vacuum laminating method.
- the laminating method may be a batch method or a continuous method using a roll. If necessary, the build-up film and the circuit board may be heated (preheated) before lamination.
- the laminating conditions are preferably a pressure bonding temperature (lamination temperature) of 70 to 140 ° C.
- Fiber Reinforced Composite Material A fiber reinforced composite material according to this embodiment contains a cured product of the above-described epoxy resin composition and reinforcing fibers.
- the fiber reinforced composite material according to the present embodiment may be a composite material obtained by impregnating an epoxy resin composition into a reinforcing fiber and cured, and a composite material obtained by dispersing reinforcing fibers in the epoxy resin composition and curing the composite material. Also good.
- the method for producing the fiber reinforced composite material is not particularly limited.
- the fiber reinforced composite material can be produced by impregnating a reinforced fiber base material composed of reinforcing fibers with a varnish of an epoxy resin composition and then performing a polymerization reaction.
- the curing temperature of the polymerization reaction is preferably 50 to 250 ° C., for example, and is preferably cured at 50 to 100 ° C. to form a tack-free cured product, and further treated at 120 to 200 ° C.
- the reinforcing fiber is not particularly limited, and may be a twisted yarn, an untwisted yarn, an untwisted yarn or the like, and an untwisted yarn and an untwisted yarn are preferable from the viewpoint of achieving both moldability and mechanical strength of the fiber-reinforced resin molded product.
- the form of the reinforcing fiber is not particularly limited, and for example, a fiber in which the fiber direction is aligned in one direction, a woven fabric, or the like can be used.
- the woven fabric can be freely selected from plain weaving, satin weaving, and the like according to the site and use.
- Examples of the material of the reinforcing fiber include carbon fiber, glass fiber, aramid fiber, boron fiber, alumina fiber, silicon carbide fiber and the like because they are excellent in mechanical strength and durability. These two or more types may be used in combination. it can. Among these, carbon fiber is preferable because the strength of the molded product is particularly favorable. Various carbon fibers such as polyacrylonitrile, pitch, and rayon can be used. Among these, a polyacrylonitrile-based one that can easily obtain a high-strength carbon fiber is preferable.
- the amount of reinforcing fibers used when a reinforced varnish made of reinforcing fibers is impregnated into a fiber reinforced composite material is such that the volume content of the reinforcing fibers in the fiber reinforced composite material is in the range of 40% to 85%. Is preferred.
- Fiber-reinforced resin molded article according to the fiber-reinforced resin molded article may be one that contains a fiber-reinforced composite materials described above.
- the fiber-reinforced resin molded product according to this embodiment can also be referred to as a molded product containing reinforcing fibers and a cured product of the above-described epoxy resin composition.
- the manufacturing method of the fiber reinforced resin molded product is not particularly limited.
- a fiber-reinforced resin molded product can be obtained by heat-curing a composite material containing the above-described epoxy resin composition and reinforcing fibers.
- the fiber reinforced resin molded product may be manufactured by a hand lay-up method or a spray-up method in which a fiber aggregate is spread on a mold and multiple varnishes of an epoxy resin composition are laminated.
- the fiber reinforced resin molded product is a flexible mold that can be formed by stacking and molding a reinforcing fiber substrate made of reinforcing fibers while impregnating varnish using a male mold or a female mold, and allowing pressure to act on the molded product.
- the fiber reinforced resin molded product is composed of an epoxy resin composition varnish, a reinforcing fiber mixed into a sheet, molded into a sheet, and compression molded with a mold.
- a prepreg in which reinforcing fibers are impregnated with varnish is produced by a method such as an RTM method in which varnish is injected, and this is baked and hardened with a large autoclave or the like.
- the amount of reinforcing fiber in the fiber reinforced resin molded product is preferably 40 to 70% by mass, and particularly preferably 50 to 70% by mass from the viewpoint of strength.
- Electrically conductive paste which concerns on this embodiment contains the above-mentioned epoxy resin composition and electroconductive particle.
- the conductive particles include silver particles and copper particles.
- the conductive paste can be used for applications such as a resin paste for circuit connection and an anisotropic conductive adhesive. You may select suitably the electroconductive particle of an electrically conductive paste according to these uses.
- Example 1 104 parts by mass of epoxy compound A-1, 85 parts by mass of curing agent (manufactured by DIC Corporation, TD-2131: phenol novolac resin, hydroxyl group equivalent: 104 g / eq), curing accelerator (manufactured by Hokuko Chemical Co., Ltd., triphenyl) 3 parts by mass of phosphine), 800 parts by mass of fused silica (manufactured by Electrochemical Co., Ltd., spherical silica FB-560), silane coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd., ⁇ -glycidoxytriethoxyxysilane KBM-403) 3 parts by mass, Carnauba wax (manufactured by Electrochemical Co., Ltd., PEARL WAX No. 1-P) and 2 parts by mass of carbon black (Mitsubishi Chemical, # 2600), Was melt-kneaded for 5 minutes at a temperature of 90
- the obtained epoxy resin composition was pulverized into a disk shape of ⁇ 50 mm ⁇ 3 (t) mm in a transfer molding machine at a pressure of 70 kg / cm 2 , a temperature of 175 ° C., and a time of 180 seconds. And further cured at 180 ° C. for 5 hours to obtain a cured molded product of the epoxy resin composition.
- a cured molded product of the epoxy resin composition was cut into a size of 0.8 mm in thickness, 5 mm in width, and 54 mm in length, and this was used as test piece 1.
- a viscoelasticity measuring device DMA: solid viscoelasticity measuring device “RSAII” manufactured by Rheometric Co., Ltd., rectangular tension method: frequency 1 Hz, heating rate 3 ° C./min
- the temperature (the tan ⁇ change rate is the largest) was measured as the glass transition temperature, and the storage elastic modulus at 260 ° C. was measured as the thermal elastic modulus.
- the shrinkage rate at the time of molding was measured by the following method.
- an epoxy resin composition is injection-molded using a transfer molding machine (KTS-15-1.5C, manufactured by Kotaki Seiki Co., Ltd.) under conditions of a mold temperature of 150 ° C., a molding pressure of 9.8 MPa, and a curing time of 600 seconds.
- a test piece having a length of 110 mm, a width of 12.7 mm, and a thickness of 1.6 mm was produced. Thereafter, the test piece was post-cured at 175 ° C. for 5 hours, and the inner diameter of the mold cavity was measured.
- the outer diameter of the post-cure test piece was measured at room temperature (25 ° C.). Vertical dimension of the mold at 25 ° C. (hereinafter referred to as mold dimension at 25 ° C.), vertical dimension of the test piece after post-cure (hereinafter referred to as cured product dimension at 25 ° C.), mold at 175 ° C.
- the shrinkage rate was calculated from the vertical dimension (hereinafter referred to as 175 ° C. mold dimension) by the following formula.
- Shrinkage rate (%) ⁇ (25 ° C. mold size) ⁇ (25 ° C. cured product size) ⁇ / (175 ° C. mold size) ⁇ 100 (%)
- Example 2 An epoxy resin composition was prepared and evaluated in the same manner as in Example 1 except that 120 parts by mass of epoxy compound A-2 was used instead of epoxy compound A-1 and the amount of the curing agent was 69 parts by mass. . The evaluation results are shown in Table 1.
- Example 1 except that 122 parts by mass of a compound represented by the following formula (EPICLON 850-S manufactured by DIC Corporation) was used in place of the epoxy compound A-1 and the amount of the curing agent was 67 parts by mass.
- An epoxy resin composition was prepared and evaluated in the same manner as described above. The evaluation results are shown in Table 1.
- Example 1 except that 109 parts by mass of a compound represented by the following formula (EPICLON HP-4032D manufactured by DIC Corporation) was used in place of the epoxy compound A-1 and the amount of the curing agent was 80 parts by mass.
- An epoxy resin composition was prepared and evaluated in the same manner as described above. The evaluation results are shown in Table 1.
- the epoxy resin composition according to the present invention can be suitably used for applications such as semiconductor sealing materials, semiconductor devices, prepregs, circuit boards, build-up films, fiber reinforced composite materials, fiber reinforced resin molded products, and conductive pastes. it can.
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Abstract
Description
本実施形態に係るエポキシ樹脂組成物は、ナフタレン型エポキシ化合物とエポキシ樹脂用硬化剤とを含有する。
ナフタレン型エポキシ化合物は、ナフタレン環と、ナフタレン環に直接結合するアリル基及びグリシジル基からなる群より選択される少なくとも一種の基(A)と、ナフタレン環に直接結合するアリルオキシ基及びグリシジルオキシ基からなる群より選択される少なくとも一種の基(B)と、を有している。基(A)は、ナフタレン環に炭素原子で結合しており、基(B)は、ナフタレン環に酸素原子で結合している。
エポキシ樹脂用硬化剤は特に限定されず、ナフタレン型エポキシ化合物が有するエポキシ含有基同士を架橋可能な成分であればよい。
エポキシ樹脂組成物は、ナフタレン型エポキシ化合物及びエポキシ樹脂用硬化剤以外の他の成分を更に含有していてよい。
本実施形態に係るエポキシ樹脂組成物は、硬化成形時の収縮率、硬化物の耐熱性、及び硬化物の熱時弾性率に優れている。このため、エポキシ樹脂組成物、エポキシ樹脂組成物の硬化物、及び、当該硬化物を含む樹脂材料は、それぞれ様々な用途に好適に用いることができる。例えば、本実施形態では、エポキシ樹脂組成物を、半導体封止材料、半導体装置、プリプレグ、回路基板(プリント回路基板、ビルドアップ基板等)、ビルドアップフィルム、繊維強化複合材料、繊維強化樹脂成形品、導電ペースト等に適用することができる。
本実施形態に係る半導体封止材料は、上述のエポキシ樹脂組成物を含有している。エポキシ樹脂組成物は無機充填材を含んでおり、更に他の配合剤を含んでいてもよい。半導体封止材料は、例えば、ナフタレン型エポキシ化合物、エポキシ樹脂用硬化剤及び無機充填材(必要に応じて更に他の配合剤)を、押出機、ニーダ、ロール等を用いて溶融混合することにより調製してよい。無機充填剤としては、通常、溶融シリカが用いられる。また、パワートランジスタ、パワーIC等に使用される高熱伝導半導体封止材として用いる場合は、より熱伝導率の高い、結晶シリカ、アルミナ、窒化ケイ素などを用い、高充填化してもよい。
本実施形態に係る半導体装置は、上述の半導体封止材料の硬化物を含有する封止材を備えている。封止材の形成方法は特に限定されず、例えば、半導体封止材料を、注型成形機、トランスファー成形機、射出成形機等を用いて成形し、50~200℃で2~10時間の間、加熱する方法が挙げられる。
本実施形態に係るプリプレグは、補強基材と、当該補強基材に含浸させた上述のエポキシ樹脂組成物と、を含有する含浸基材の半硬化物である。プリプレグの製造方法は特に限定されず、例えば、有機溶剤を配合してワニス化したエポキシ樹脂組成物を、補強基材(紙、ガラス布、ガラス不織布、アラミド紙、アラミド布、ガラスマット、ガラスロービング布等)に含浸したのち、用いた溶剤種に応じた加熱温度(例えば、50~170℃)で加熱する方法が挙げられる。エポキシ樹脂組成物と補強基材の割合は特に限定されないが、例えば、プリプレグ中の樹脂分が20~60質量%となるように調整することが好ましい。
本実施形態に係る回路基板は、金属箔と、金属箔上に設けられた硬化樹脂層と、を備えており、硬化樹脂層は、上述のエポキシ樹脂組成物の硬化物を含んでいる。本実施形態に係る回路基板の具体例としては、プリント回路基板、ビルドアップ基板等が挙げられる。
本実施形態に係るプリント回路基板は、金属箔と、金属箔上に設けられた硬化樹脂層とを備えている。本実施形態において、例えば、硬化樹脂層は、上述のプリプレグの硬化物から構成されていてよい。すなわち、硬化樹脂層は、エポキシ樹脂組成物の硬化物と補強基材とを含んでいてよい。金属箔としては、例えば銅箔が挙げられ、銅箔が好ましい。
本実施形態に係るビルドアップ基板は、金属箔と、金属箔上に設けられた硬化樹脂層とを備えており、硬化樹脂層は、上述のエポキシ樹脂組成物の硬化物を含んでいる。金属箔としては、例えば銅箔が挙げられ、銅箔が好ましい。
本実施形態に係るビルドアップフィルムは、上述のエポキシ樹脂組成物を含有する。本実施形態に係るビルドアップフィルムは、基材フィルムと、基材フィルム上に設けられた上述のエポキシ樹脂組成物を含有する樹脂層と、を備えていてもよい。ビルドアップフィルムは、樹脂層の基材フィルムと反対側の面上に、保護フィルムを更に備えていてもよい。
本実施形態に係る繊維強化複合材料は、上述のエポキシ樹脂組成物の硬化物と強化繊維とを含有している。本実施形態に係る繊維強化複合材料は、強化繊維にエポキシ樹脂組成物が含浸させ、硬化した複合材料であってよく、エポキシ樹脂組成物中に強化繊維を分散させ、硬化した複合材料であってもよい。
本実施形態に係る繊維強化樹脂成形品は、上述の繊維強化複合材料を含有するものであってよい。本実施形態に係る繊維強化樹脂成形品は、強化繊維と、上述のエポキシ樹脂組成物の硬化物と、を含有する成形品ということもできる。
本実施形態に係る導電ペーストは、上述のエポキシ樹脂組成物と、導電性粒子とを含有している。導電性粒子としては、例えば銀粒子、銅粒子等が挙げられる。
Synlett,2006,14,2211.に記載の方法を参考に、1,5-ジヒドロキシナフタレンを原料として、下記式で表される1,5-ジアリルオキシ-2,6-ジアリルナフタレンを合成した。
2.0Lナスフラスコに、タングステン酸ナトリウム二水和物(26.6g、80.6mmol)、メチルトリ-n-オクチルアンモニウム硫酸水素塩(38.5g、82.7mmol)、メチレンジホスホン酸(3.5g、19.9mmol)、硫酸ナトリウム(102.5g、721.8mmol)、及び、1,5-ジアリルオキシ-2,6-ジアリルナフタレン(80.3g、250.6mmol)をトルエン(500ml)に溶解させた。次いで、30%過酸化水素水(192.3g、1.70mol)を加え、40℃で16時間反応させた。反応後、トルエン(1000ml)を加え、有機層を分離し、蒸留水(500ml)で3回分液洗浄し、減圧下で溶媒留去して、褐色固体のエポキシ化合物A-1(75.3g)を得た。
オレフィン含有基の転化率(%)=(1-未反応のオレフィン含有基の合計量(mol)/原料化合物のオレフィン含有基の合計量(mol))×100
エポキシ含有基の収率(%)=(生成したエポキシ含有基の合計量(mol)/原料化合物のオレフィン含有基の合計量(mol))×100
エポキシ化選択率(%)=(エポキシ含有基の収率/オレフィン含有基の転化率)×100
2.0Lナスフラスコに、タングステン酸ナトリウム二水和物(26.6g、80.6mmol)、メチルトリ-n-オクチルアンモニウム硫酸水素塩(38.5g、82.7mmol)、メチレンジホスホン酸(3.5g、19.9mmol)、硫酸ナトリウム(102.5g、721.8mmol)、及び、1,5-ジアリルオキシ-2,6-ジアリルナフタレン(80.3g、250.6mmol)をトルエン(500ml)に溶解させた。次いで、30%過酸化水素水(147.3g、1.1mol)を加え、40℃で16時間反応させた。反応後、トルエン(1000ml)を加え、有機層を分離し、蒸留水(500ml)で3回分液洗浄し、減圧下で溶媒留去して、褐色固体のエポキシ化合物A-2(65.4g)を得た。
エポキシ化合物A-1を104質量部、硬化剤(DIC株式会社製、TD-2131:フェノールノボラック樹脂、水酸基当量:104g/eq)を85質量部、硬化促進剤(北興化学株式会社製、トリフェニルホスフィン)を3質量部、溶融シリカ(電気化学株式会社製、球状シリカ FB-560)を800質量部、シランカップリング剤(信越化学工業株式会社製、γ-グリシドキシトリエトキシキシシラン KBM-403)を3質量部、カルナウバワックス(電気化学株式会社製、PEARL WAX No.1-P)を2質量部、カーボンブラック(三菱化学製、#2600)を3質量部配合したのち、2本ロールを用いて90℃の温度で5分間溶融混練して目的のエポキシ樹脂組成物を得た。
次に、得られたエポキシ樹脂組成物を粉砕したものを、トランスファー成形機にて、圧力70kg/cm2、温度175℃、時間180秒でφ50mm×3(t)mmの円板状に成形し、180℃で5時間さらに硬化して、エポキシ樹脂組成物の硬化成形物を得た。
成形時の収縮率は、以下の方法で測定した。まず、トランスファー成形機(コータキ精機製、KTS-15-1.5C)を用いて、金型温度150℃、成形圧力9.8MPa、硬化時間600秒の条件下で、エポキシ樹脂組成物を注入成形して、縦110mm、横12.7mm、厚さ1.6mmの試験片を作製した。その後、試験片を175℃で5時間ポストキュアするとともに、金型キャビティの内径寸法を測定した。最後に、ポストキュア後の試験片の外径寸法を室温(25℃)で測定した。25℃での金型の縦方向の寸法(以下、25℃の金型寸法)、ポストキュア後の試験片の縦方向の寸法(以下、25℃の硬化物寸法)、175℃での金型の縦方向の寸法(以下、175℃の金型寸法)から、以下の式により収縮率を算出した。
収縮率(%)={(25℃の金型寸法)-(25℃の硬化物寸法)}/(175℃の金型寸法)×100(%)
エポキシ化合物A-1に代えてエポキシ化合物A-2を120質量部用い、硬化剤の量を69質量部としたこと以外は、実施例1と同様にしてエポキシ樹脂組成物を調製し、評価した。評価結果を表1に示す。
エポキシ化合物A-1に代えて、下記式で表される化合物(DIC株式会社製、EPICLON 850-S)を122質量部用い、硬化剤の量を67質量部としたこと以外は、実施例1と同様にしてエポキシ樹脂組成物を調製し、評価した。評価結果を表1に示す。
エポキシ化合物A-1に代えて、下記式で表される化合物(DIC株式会社製、EPICLON HP-4032D)を109質量部用い、硬化剤の量を80質量部としたこと以外は、実施例1と同様にしてエポキシ樹脂組成物を調製し、評価した。評価結果を表1に示す。
エポキシ化合物A-1に代えて、下記式で表される4官能型(非特許文献Synlett,2006,14,2211.を参考に、ビスフェノールAから合成した化合物)を98質量部用い、硬化剤の量を91質量部としたこと以外は、実施例1と同様にしてエポキシ樹脂組成物を調製し、評価した。評価結果を表1に示す。
Claims (11)
- ナフタレン型エポキシ化合物とエポキシ樹脂用硬化剤とを含有するエポキシ樹脂組成物であって、
前記ナフタレン型エポキシ化合物が、ナフタレン環と、前記ナフタレン環に直接結合するアリル基及びグリシジル基からなる群より選択される少なくとも一種の基(A)と、前記ナフタレン環に直接結合するアリルオキシ基及びグリシジルオキシ基からなる群より選択される少なくとも一種の基(B)と、を有し、且つ、前記アリル基及び前記アリルオキシ基のうち少なくとも一種と、前記グリシジル基及び前記グリシジルオキシ基のうち少なくとも一種と、を有する、
エポキシ樹脂組成物。 - 前記ナフタレン型エポキシ化合物が、前記グリシジル基及び前記グリシジルオキシ基の両方を有する、請求項1に記載のエポキシ樹脂組成物。
- 前記基(A)が、前記ナフタレン環の前記基(B)と隣接する位置に結合している、請求項1又は2に記載のエポキシ樹脂組成物。
- 請求項1~3のいずれか一項に記載のエポキシ樹脂組成物の硬化物を含有する、樹脂材料。
- 請求項1~3のいずれか一項に記載のエポキシ樹脂組成物を含み、
前記エポキシ樹脂組成物が無機充填材を更に含有する、半導体封止材料。 - 請求項5に記載の半導体封止材料の硬化物を含有する封止材を備える、半導体装置。
- 補強基材と、前記補強基材に含浸させた請求項1に記載のエポキシ樹脂組成物と、を含有する含浸基材の半硬化物である、プリプレグ。
- 金属箔と、前記金属箔上に設けられた請求項1に記載のエポキシ樹脂組成物の硬化物を含有する硬化樹脂層と、を備える、回路基板。
- 請求項1に記載のエポキシ樹脂組成物を含有する、ビルドアップフィルム。
- 請求項1に記載のエポキシ樹脂組成物の硬化物と強化繊維とを含有する、繊維強化複合材料。
- 請求項1に記載のエポキシ樹脂組成物と導電性粒子とを含有する、導電ペースト。
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JP2020015864A (ja) * | 2018-07-27 | 2020-01-30 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板、半導体チップパッケージ、及び半導体装置 |
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