JP6350776B1 - エポキシ樹脂組成物 - Google Patents
エポキシ樹脂組成物 Download PDFInfo
- Publication number
- JP6350776B1 JP6350776B1 JP2018512447A JP2018512447A JP6350776B1 JP 6350776 B1 JP6350776 B1 JP 6350776B1 JP 2018512447 A JP2018512447 A JP 2018512447A JP 2018512447 A JP2018512447 A JP 2018512447A JP 6350776 B1 JP6350776 B1 JP 6350776B1
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- JP
- Japan
- Prior art keywords
- group
- epoxy resin
- resin composition
- epoxy
- naphthalene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 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 116
- 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 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- -1 glycidyloxy group Chemical group 0.000 claims abstract description 69
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 17
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 15
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims description 121
- 239000011347 resin Substances 0.000 claims description 121
- 239000000463 material Substances 0.000 claims description 40
- 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 23
- 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 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
- 239000000047 product Substances 0.000 description 55
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 38
- 238000001723 curing Methods 0.000 description 33
- 239000004643 cyanate ester Substances 0.000 description 33
- 239000010410 layer Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 27
- 239000003063 flame retardant Substances 0.000 description 26
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- 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 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000835 fiber Substances 0.000 description 15
- 229920003986 novolac Polymers 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 238000004519 manufacturing process Methods 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000010030 laminating Methods 0.000 description 8
- 230000001681 protective effect Effects 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
- 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
- 239000002966 varnish Substances 0.000 description 7
- 229920000877 Melamine resin Polymers 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
- 239000002994 raw material 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
- 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
- 150000002989 phenols Chemical class 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000012360 testing method Methods 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
- 125000004104 aryloxy group Chemical group 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
- 229910052757 nitrogen Inorganic materials 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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000003475 lamination Methods 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 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
- 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
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- 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
- 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
- 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- 229910052719 titanium Inorganic materials 0.000 description 1
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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
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- 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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- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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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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- 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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- C08K7/04—Fibres or whiskers inorganic
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- H—ELECTRICITY
- 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
-
- 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
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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 (10)
- 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両方を有する、
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に記載のエポキシ樹脂組成物。
- 請求項1〜2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1〜2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4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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JPH0543658A (ja) * | 1991-08-13 | 1993-02-23 | Shin Etsu Chem Co Ltd | 熱硬化性樹脂組成物 |
JPH0586156A (ja) * | 1991-09-30 | 1993-04-06 | Nippon Kayaku Co Ltd | 新規ノボラツク型化合物、樹脂、及びその製造法 |
JPH07258241A (ja) * | 1994-03-24 | 1995-10-09 | Dai Ichi Kogyo Seiyaku Co Ltd | グリシジルエーテル化合物及びエポキシ樹脂組成物 |
JP2014531473A (ja) * | 2011-08-25 | 2014-11-27 | コリア インスティチュート オブ インダストリアル テクノロジー | アルコキシシリル基を有するエポキシ化合物、その製造方法、それを含む組成物と硬化物及びその用途 |
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US5290882A (en) * | 1991-08-13 | 1994-03-01 | Shin-Etsu Chemical Co., Ltd. | Thermosetting resin compositions |
WO2010099029A1 (en) * | 2009-02-27 | 2010-09-02 | Cytec Technology Corp. | Epoxy compositions with improved mechanical performance |
MY156448A (en) * | 2010-07-30 | 2016-02-26 | Dainippon Ink & Chemicals | Curable resin composition, cured product thereof, phenol resin, epoxy resin, and semiconductor encapsulating material |
EP2933257B1 (en) | 2012-09-17 | 2017-07-26 | Korea Institute Of Industrial Technology | Epoxy compound having alkoxysilyl group, method for preparing same, composition comprising same, cured product made therefrom, and use thereof |
JP5859949B2 (ja) * | 2012-09-27 | 2016-02-16 | 三ツ星ベルト株式会社 | 導電性組成物 |
JP6114037B2 (ja) * | 2013-01-07 | 2017-04-12 | 旭化成株式会社 | エポキシ樹脂用硬化剤及びエポキシ樹脂組成物 |
CN103408510B (zh) * | 2013-07-26 | 2015-12-09 | 深圳先进技术研究院 | 含萘液晶环氧树脂化合物,其制备方法及组合物 |
JP6511760B2 (ja) * | 2013-10-02 | 2019-05-15 | 三菱ケミカル株式会社 | エポキシ化合物の製造方法及びエポキシ化反応用触媒組成物 |
JP6529245B2 (ja) | 2013-11-27 | 2019-06-12 | 昭和電工株式会社 | 硬化性樹脂組成物 |
CN104163912B (zh) * | 2014-02-12 | 2016-09-14 | 安徽善孚新材料科技股份有限公司 | 一种双重网络交联型环氧树脂及其制备方法 |
JP2015172144A (ja) * | 2014-03-12 | 2015-10-01 | パナソニックIpマネジメント株式会社 | プリプレグ、金属張積層板、プリント配線板 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPH0543658A (ja) * | 1991-08-13 | 1993-02-23 | Shin Etsu Chem Co Ltd | 熱硬化性樹脂組成物 |
JPH0586156A (ja) * | 1991-09-30 | 1993-04-06 | Nippon Kayaku Co Ltd | 新規ノボラツク型化合物、樹脂、及びその製造法 |
JPH07258241A (ja) * | 1994-03-24 | 1995-10-09 | Dai Ichi Kogyo Seiyaku Co Ltd | グリシジルエーテル化合物及びエポキシ樹脂組成物 |
JP2014531473A (ja) * | 2011-08-25 | 2014-11-27 | コリア インスティチュート オブ インダストリアル テクノロジー | アルコキシシリル基を有するエポキシ化合物、その製造方法、それを含む組成物と硬化物及びその用途 |
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CN110088164B (zh) | 2021-07-27 |
TWI752114B (zh) | 2022-01-11 |
CN110088164A (zh) | 2019-08-02 |
TW201831551A (zh) | 2018-09-01 |
KR20190093187A (ko) | 2019-08-08 |
KR102283388B1 (ko) | 2021-08-02 |
JPWO2018116757A1 (ja) | 2018-12-20 |
WO2018116757A1 (ja) | 2018-06-28 |
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