JP2016204626A - 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 - Google Patents
組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 Download PDFInfo
- Publication number
- JP2016204626A JP2016204626A JP2015255473A JP2015255473A JP2016204626A JP 2016204626 A JP2016204626 A JP 2016204626A JP 2015255473 A JP2015255473 A JP 2015255473A JP 2015255473 A JP2015255473 A JP 2015255473A JP 2016204626 A JP2016204626 A JP 2016204626A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- compound
- composition
- composition according
- group
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 191
- -1 cured article Substances 0.000 title claims abstract description 125
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 112
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 112
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 47
- 239000004065 semiconductor Substances 0.000 title claims description 11
- 239000011229 interlayer Substances 0.000 title claims description 9
- 239000012774 insulation material Substances 0.000 title 1
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000000732 arylene group Chemical group 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 47
- 239000000047 product Substances 0.000 claims description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000004202 carbamide Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 10
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 229930185605 Bisphenol Natural products 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910005965 SO 2 Inorganic materials 0.000 claims description 6
- 239000011810 insulating material Substances 0.000 claims description 6
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 150000004714 phosphonium salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 7
- 238000002156 mixing Methods 0.000 description 23
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 8
- 239000003063 flame retardant Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical group C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 229910002026 crystalline silica Inorganic materials 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011521 glass Substances 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
- 239000012778 molding material Substances 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 235000014380 magnesium carbonate Nutrition 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- HEUDNCPBUYZJDR-UHFFFAOYSA-N 1,1-dimethyl-3-(2-methylphenyl)urea Chemical compound CN(C)C(=O)NC1=CC=CC=C1C HEUDNCPBUYZJDR-UHFFFAOYSA-N 0.000 description 1
- QTERLAXNZRFFMZ-UHFFFAOYSA-N 1,1-dimethyl-3-(4-methylphenyl)urea Chemical compound CN(C)C(=O)NC1=CC=C(C)C=C1 QTERLAXNZRFFMZ-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 1
- PESXPUCWMKUMSI-UHFFFAOYSA-N 3-[2-(dimethylcarbamoylamino)phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC=C1NC(=O)N(C)C PESXPUCWMKUMSI-UHFFFAOYSA-N 0.000 description 1
- KDQTUCKOAOGTLT-UHFFFAOYSA-N 3-[3-(dimethylcarbamoylamino)-4-methylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(C)C(NC(=O)N(C)C)=C1 KDQTUCKOAOGTLT-UHFFFAOYSA-N 0.000 description 1
- HGVQBXSOAUVVNX-UHFFFAOYSA-N 4-[(2,4-diamino-5-methylphenyl)methyl]-6-methylbenzene-1,3-diamine Chemical compound C1=C(N)C(C)=CC(CC=2C(=CC(N)=C(C)C=2)N)=C1N HGVQBXSOAUVVNX-UHFFFAOYSA-N 0.000 description 1
- USBRHIZNALIOEI-UHFFFAOYSA-N 4-[(4-hydroxy-3-prop-2-enylphenyl)methyl]-2-prop-2-enylphenol Chemical compound C1=C(CC=C)C(O)=CC=C1CC1=CC=C(O)C(CC=C)=C1 USBRHIZNALIOEI-UHFFFAOYSA-N 0.000 description 1
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical group C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
- GIGYUDLDUWARIU-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-methyl-5-prop-2-enylphenyl)propan-2-yl]-2-methyl-6-prop-2-enylphenol Chemical compound C=CCC1=C(O)C(C)=CC(C(C)(C)C=2C=C(CC=C)C(O)=C(C)C=2)=C1 GIGYUDLDUWARIU-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical group C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012803 melt mixture Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IUURMAINMLIZMX-UHFFFAOYSA-N tris(2-nonylphenyl)phosphane Chemical compound CCCCCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCCCCC)C1=CC=CC=C1CCCCCCCCC IUURMAINMLIZMX-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/506—Amines heterocyclic containing only nitrogen as a heteroatom having one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
-
- 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
- C08K3/34—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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/21—Urea; Derivatives thereof, e.g. biuret
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
- C08K5/3447—Five-membered rings condensed with carbocyclic rings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Insulating Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
本発明は、さらに別の態様として、上記の本発明に係る熱硬化性組成物の硬化物を提供する。
本発明の一実施形態に係る組成物(以下、この組成物を「本組成物」ともいう。)は、上記の一般式(1)で表されるマレイミド化合物(A)、上記の一般式(2)で表される芳香族アミン化合物(B)、および上記の一般式(3)で表されるフェノール化合物(C)を含有する。一実施形態において、本組成物は、上記のマレイミド化合物(A)、芳香族アミン化合物(B)、およびフェノール化合物(C)を含む組成物の溶融混合体である。
マレイミド化合物(A)の具体例としては、N,N’−4,4’−ジフェニルメタンビスマレイミド、N,N’−m−フェニレンビスマレイミド、N,N’−4,4’−ジフェニルエーテルビスマレイミド、N,N’−m−キシレンビスマレイミドなどを挙げることができる。
本組成物が上記の溶融混合体である場合において、マレイミド化合物(A)由来のマレイミド基の総数が、芳香族アミン化合物(B)由来の一級アミノ基とフェノール化合物(C)由来のアリル基との総数の1.5倍以上2.5倍以下となる成分混合比で、溶融混合が行われてもよい。このような条件で溶融混合が行われることにより、本組成物を成分として含む熱硬化性組成物の硬化物の耐熱特性を向上させることができる場合がある。上記の成分混合比は、1.8以上2.2以下であることが好ましく、1.9以上2.1以下であることがより好ましい。
ニルアラルキル型エポキシ樹脂、フェノール、ナフトールなどのキシリレン結合によるアラルキル樹脂のエポキシ化物などから選ばれる芳香環の多い多官能型エポキシ樹脂を使用するのが好ましい。
4,4’−(ジメチルメチレン)ビス[2−(2−プロペニル)フェノール]30.8g(0.10モル)(大和化成工業社製、DABPA、水酸基当量159g/eq、)、1,3-フェニレンジアミン10.8g(0.10モル)、および4,4’−ジフェニルメタンビスマレイミド143.2g(0.40モル)を150℃で20分間攪拌後常温冷却することより、混合生成物として均質な赤褐色のガラス状溶融物184.5g(混合生成物1)が得られた。
ICI溶融粘度計により測定した150℃における混合生成物1の溶融粘度は480mPa・sであった。また混合生成物1の水酸基当量は、DABPAの水酸基当量およびその成分濃度から924g/eqと算出された。本実施例1で得られた混合生成物1を組成物1とし、硬化剤として用いた場合には「硬化剤1」と称する場合もある。
下記一般式(6)で示されるエポキシ樹脂(日本化薬社製「NC3000」フェノールビフェニルアラルキル型、エポキシ当量275g/eq)、実施例1で得られた硬化剤1、溶融シリカ、およびイミダゾール系硬化促進剤(四国化成社製「キュアゾール C11Z−A」)からなる硬化促進剤を表2に示す割合(表2中の数値は質量部、以下同じ。)で配合し、充分に混合した後、85±3℃の2本ロールで3分間混練し、冷却、粉砕することにより成形用組成物をエポキシ樹脂組成物として得た。トランスファー成形機でこのエポキシ樹脂組成物を圧力100kgf/cm2で175℃2分間成形した後、230℃6時間のポストキュアを行い、ガラス転移温度測定用、350℃重量減少率測定用、および難燃性試験用のテストピースを調製し、その評価を行った。その結果を表2に示した。
(式中、Gはグリシジル基、nは1〜10の自然数)
表2に示される配合割合で、イミダゾール系硬化促進剤(四国化成社製「キュアゾール C11Z−A」)およびウレア系硬化促進剤(サンアプロ社製「U−CAT 3513N」)からなる硬化促進剤を用いたこと以外は、実施例2と同様にして成形用組成物を調製しエポキシ樹脂組成物として得た。その評価を行った結果を表2に示す。
イミダゾール系硬化促進剤に代えて、表2に示される配合割合で、ウレア系硬化促進剤(サンアプロ社製「U−CAT 3512T」)を用いたこと以外は、実施例2と同様にして成形用組成物を調製しエポキシ樹脂組成物として得た、その評価を行った結果を表2に示す。
表2に示される配合割合で、実施例1と同様にして成形用組成物を調製し、組成物1(硬化物1)を主たる硬化成分とする熱硬化性組成物として得た。その評価を行った結果を表2に示す。なお、表2では、実施例5により製造された熱硬化性組成物は、表示の都合上、エポキシ樹脂組成物のように示されているが、エポキシ基を有する成分を含有していない。
フェノールノボラック変性トリフェノールメタン樹脂18.8g(エア・ウォーター社製「HE910C−10」、水酸基当量100g/eq)2,7−ジヒドロキシナフタレン9.6g(0.06モル)を150℃で30分間溶融混合したのち、液温を120℃に下げて4,4’−ジフェニルメタンビスマレイミド71.6g(0.20モル)を添加した。これを同温で30分間攪拌後常温冷却することより、混合生成物2として均質な黒褐色のガラス状溶融物100.0gが得られた。
ICI溶融粘度計により測定した150℃における混合生成物2の溶融粘度は80mPa・sであった。また混合生成物2の水酸基当量は、アセチル化逆滴定法による測定の結果295g/eqであった。本比較例1で得られた混合生成物2を硬化剤2とする。
実施例1により作製した硬化剤1および比較例1により作製した硬化剤2の物性を表1に示した。
上記一般式(6)で示されるエポキシ樹脂、比較例1で得られた硬化剤2、溶融シリカ、およびイミダゾール系硬化促進剤(四国化成社製「キュアゾール C11Z−A」)を表2に示される割合で配合し、以下、実施例2と同様にして成形用組成物を調製しエポキシ樹脂組成物として得た。その評価を行った結果を表2に示す。
エポキシ樹脂組成物等2.5gをタブレットにして、高下式フローテスター(温度175℃、オリフィス径1mm、長さ1mm)にて測定した。
TMA(熱機械分析装置)を用いて、エポキシ樹脂組成物等のテストピースの線膨張係数を昇温速度10℃/分で測定し、線膨張係数の変曲点をガラス転移温度とした。
TGA(熱重量分析装置)を用いて、エポキシ樹脂組成物等のテストピースを昇温速度10℃/分で加熱して350℃に到達したときの重量減少率を測定した。この重量減少率が低いほど、高温下低分解特性に優れるといえる。
厚み1.6mm×幅10mm×長さ135mmのエポキシ樹脂組成物等のサンプル(1例あたり5枚)を用い、UL−94Vに準拠して残炎時間を測定し評価した。各サンプルに対して2回の接炎を行って測定された残炎時間のうち、最長の時間をFmax(単位:秒間)とし、5枚のサンプルに対する試験による残炎時間の合計をFtotal(単位:秒間)とした。これらの評価結果を表2に示す。
また本発明により、高難燃性、高耐熱性、および高温下での低熱分解性を満たす新規の、エポキシ樹脂硬化剤を用いたエポキシ樹脂組成物およびその硬化物、ならびに熱硬化性組成物およびその硬化物が提供される。
本発明により、特にエポキシ樹脂硬化剤として有用であり、とりわけ半導体・パワーデバイス封止用、層間絶縁材料として用いた場合に、難燃性、硬化性、より高耐熱性に優れた、エポキシ樹脂組成物を形成することができる組成物およびそのエポキシ樹脂組成物、ならびに熱硬化性組成物を形成することができる組成物およびその熱硬化性組成物が提供される。
Claims (21)
- 下記一般式(1)で表されるマレイミド化合物(A)、下記一般式(2)で表される芳香族アミン化合物(B)、および下記一般式(3)で表されるフェノール化合物(C)を含有する組成物。
(式(2)中、Ar2は一級アミノ基を0〜2個の範囲で含み、炭化水素の置換基が存在してよい炭素数6〜12のアリーレン基であり、X2は直接結合、炭素数1〜6の2価の炭化水素基、O、S、またはSO2であり、qは0〜2の整数である。)
- 150℃溶融粘度が50mPa・s以上1000mPa・s以下であり、かつ水酸基当量が300g/eq以上1500g/eq以下である、請求項1に記載の組成物。
- 前記マレイミド化合物(A)と前記芳香族アミン化合物(B)との反応生成物をさらに含有する、請求項1または2に記載の組成物。
- 前記反応生成物は、前記マレイミド化合物(A)と前記芳香族アミン化合物(B)とのマイケル付加物である、請求項4に記載の組成物。
- 前記マレイミド化合物(A)、前記芳香族アミン化合物(B)、および前記フェノール化合物(C)を含む組成物の溶融混合体である、請求項1から4のいずれか一項に記載の組成物。
- 前記マレイミド化合物(A)由来のマレイミド基に基づく部分構造の総数は、前記芳香族アミン化合物(B)由来の一級アミノ基に基づく部分構造と前記フェノール化合物(C)由来のアリル基に基づく部分構造との総数の1.5倍以上2.5倍以下である、請求項1から5のいずれか一項に記載の組成物。
- 前記フェノール化合物(C)が、下記一般式(4)で示されるビスフェノール化合物(C1)を含む、請求項1から6のいずれか一項に記載の組成物。
(式(4)中、R4およびR5はそれぞれ独立に炭素数1〜4の炭化水素基であり、R6およびR7はそれぞれ独立に水素原子、メチル基、フェニル基であり、cおよびdはそれぞれ独立に0〜3の整数である。) - 前記マレイミド化合物(A)は、前記一般式(1)におけるpが0または1である、請求項1から7のいずれか一項に記載の組成物。
- 前記芳香族アミン化合物(B)は、下記一般式(5)で表されるフェニレンジアミン化合物(B1)である、請求項1から8のいずれか一項に記載の組成物。
- 請求項1から9のいずれかに記載される組成物を含むエポキシ樹脂硬化剤。
- 請求項10に記載されるエポキシ樹脂硬化剤とエポキシ樹脂とを含むエポキシ樹脂組成物。
- さらに硬化促進剤を含む、請求項11に記載のエポキシ樹脂組成物。
- 前記硬化促進剤が、イミダゾール系化合物、ウレア系化合物、およびホスホニウム塩からなる群から選ばれる一種または二種以上を含む、請求項12に記載のエポキシ樹脂組成物。
- 前記硬化促進剤が、イミダゾール系化合物およびウレア系化合物を含む、請求項13に記載のエポキシ樹脂組成物。
- さらに無機充填材を含む、請求項11から14のいずれか一項に記載のエポキシ樹脂組成物。
- 請求項11から15のいずれかに記載されるエポキシ樹脂組成物の硬化物。
- 請求項1から9のいずれかに記載される組成物を含む熱硬化性組成物。
- さらに無機充填材を含む、請求項17に記載の熱硬化性組成物。
- 請求項17または18に記載される熱硬化性組成物の硬化物。
- 請求項11から15のいずれかに記載されるエポキシ樹脂組成物または請求項17または18に記載される熱硬化性組成物で封止された半導体装置。
- 請求項11から15のいずれかに記載されるエポキシ樹脂組成物または請求項17または18に記載される熱硬化性組成物を含有する層間絶縁材料。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW105110535A TWI693250B (zh) | 2015-04-27 | 2016-04-01 | 組成物、環氧樹脂固化劑、環氧樹脂組成物、熱固化性組成物、固化物、半導體裝置以及層間絕緣材料 |
CN201610245333.XA CN106084184B (zh) | 2015-04-27 | 2016-04-19 | 组合物、环氧树脂固化剂、环氧树脂组合物、热固性组合物、固化物、半导体装置以及层间绝缘材料 |
KR1020160049928A KR20160127665A (ko) | 2015-04-27 | 2016-04-25 | 조성물, 에폭시 수지 경화제, 에폭시 수지 조성물, 열경화성 조성물, 경화물, 반도체 장치 및 층간 절연 재료 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015090428 | 2015-04-27 | ||
JP2015090428 | 2015-04-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016204626A true JP2016204626A (ja) | 2016-12-08 |
JP6546527B2 JP6546527B2 (ja) | 2019-07-17 |
Family
ID=57488894
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015255473A Active JP6546527B2 (ja) | 2015-04-27 | 2015-12-26 | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP6546527B2 (ja) |
KR (1) | KR20160127665A (ja) |
CN (1) | CN106084184B (ja) |
TW (1) | TWI693250B (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018135494A (ja) * | 2017-02-24 | 2018-08-30 | 信越化学工業株式会社 | 光半導体用熱硬化性エポキシ樹脂組成物及び半導体装置 |
WO2018235751A1 (ja) * | 2017-06-22 | 2018-12-27 | エア・ウォーター株式会社 | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 |
JP2019156909A (ja) * | 2018-03-08 | 2019-09-19 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
JP2022031285A (ja) * | 2018-03-08 | 2022-02-18 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
WO2024064047A1 (en) * | 2022-09-19 | 2024-03-28 | Henkel Ag & Co. Kgaa | Resin composition for die attach film with excellent performance with large die applications |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101955754B1 (ko) * | 2016-02-16 | 2019-03-07 | 삼성에스디아이 주식회사 | 반도체 소자 밀봉용 에폭시 수지 조성물 및 이를 이용하여 밀봉된 반도체 소자 |
CN112334513B (zh) * | 2018-09-12 | 2023-08-08 | 日本化药株式会社 | 马来酰亚胺树脂、硬化性树脂组合物及其硬化物 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2518554A1 (fr) * | 1981-12-23 | 1983-06-24 | Ciba Geigy Ag | Melanges thermodurcissables a base de polyimides qui contiennent des catalyseurs de polymerisation et qui se conservent bien |
EP0383174A2 (en) * | 1989-02-17 | 1990-08-22 | Cytec Technology Corp. | Toughened thermosetting structural materials |
JPH07268074A (ja) * | 1994-03-31 | 1995-10-17 | Toagosei Co Ltd | 熱硬化性樹脂組成物 |
JP2013199627A (ja) * | 2012-02-23 | 2013-10-03 | Hitachi Chemical Co Ltd | 半導体封止用熱硬化性樹脂組成物およびそれを用いた半導体装置 |
JP2014196465A (ja) * | 2013-03-05 | 2014-10-16 | エア・ウォーター株式会社 | エポキシ樹脂の硬化剤、製法、およびその用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0597965A (ja) | 1991-10-04 | 1993-04-20 | Mitsui Toatsu Chem Inc | エポキシ樹脂組成物 |
JP3349963B2 (ja) | 1998-10-21 | 2002-11-25 | 日本電気株式会社 | 難燃性エポキシ樹脂組成物及びそれを用いた半導体装置 |
JP5030297B2 (ja) * | 2007-05-18 | 2012-09-19 | 日本化薬株式会社 | 積層板用樹脂組成物、プリプレグ及び積層板 |
CN102167825B (zh) * | 2011-03-11 | 2012-09-05 | 南京航空航天大学 | 用于微径拉挤成型工艺的双马来酰亚胺树脂及其制备方法 |
CN104530430B (zh) * | 2015-01-09 | 2017-02-01 | 西北工业大学 | 一种高韧性阻燃型双马来酰亚胺树脂及其制备方法 |
-
2015
- 2015-12-26 JP JP2015255473A patent/JP6546527B2/ja active Active
-
2016
- 2016-04-01 TW TW105110535A patent/TWI693250B/zh not_active IP Right Cessation
- 2016-04-19 CN CN201610245333.XA patent/CN106084184B/zh not_active Expired - Fee Related
- 2016-04-25 KR KR1020160049928A patent/KR20160127665A/ko not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2518554A1 (fr) * | 1981-12-23 | 1983-06-24 | Ciba Geigy Ag | Melanges thermodurcissables a base de polyimides qui contiennent des catalyseurs de polymerisation et qui se conservent bien |
JPS58117219A (ja) * | 1981-12-23 | 1983-07-12 | チバ−ガイギ−・アクチエンゲゼルシヤフト | ポリイミドをベ−スとし、重合触媒を含有する貯蔵安定な熱硬化性混合物 |
EP0383174A2 (en) * | 1989-02-17 | 1990-08-22 | Cytec Technology Corp. | Toughened thermosetting structural materials |
JPH03197559A (ja) * | 1989-02-17 | 1991-08-28 | Basf Corp | 繊維強化プリプレグの製造に適した熱硬化性ビスマレイミド樹脂系 |
JPH07268074A (ja) * | 1994-03-31 | 1995-10-17 | Toagosei Co Ltd | 熱硬化性樹脂組成物 |
JP2013199627A (ja) * | 2012-02-23 | 2013-10-03 | Hitachi Chemical Co Ltd | 半導体封止用熱硬化性樹脂組成物およびそれを用いた半導体装置 |
JP2014196465A (ja) * | 2013-03-05 | 2014-10-16 | エア・ウォーター株式会社 | エポキシ樹脂の硬化剤、製法、およびその用途 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018135494A (ja) * | 2017-02-24 | 2018-08-30 | 信越化学工業株式会社 | 光半導体用熱硬化性エポキシ樹脂組成物及び半導体装置 |
WO2018235751A1 (ja) * | 2017-06-22 | 2018-12-27 | エア・ウォーター株式会社 | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 |
JP2019006867A (ja) * | 2017-06-22 | 2019-01-17 | エア・ウォーター株式会社 | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 |
KR20200022379A (ko) | 2017-06-22 | 2020-03-03 | 에아.워타 가부시키가이샤 | 조성물, 에폭시 수지 경화제, 에폭시 수지 조성물, 열경화성 조성물, 경화물, 반도체 장치, 및 층간 절연 재료 |
KR102570300B1 (ko) | 2017-06-22 | 2023-08-24 | 에아.워타 가부시키가이샤 | 조성물, 에폭시 수지 경화제, 에폭시 수지 조성물, 열경화성 조성물, 경화물, 반도체 장치, 및 층간 절연 재료 |
JP2019156909A (ja) * | 2018-03-08 | 2019-09-19 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
JP2022031285A (ja) * | 2018-03-08 | 2022-02-18 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
JP7272405B2 (ja) | 2018-03-08 | 2023-05-12 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
WO2024064047A1 (en) * | 2022-09-19 | 2024-03-28 | Henkel Ag & Co. Kgaa | Resin composition for die attach film with excellent performance with large die applications |
Also Published As
Publication number | Publication date |
---|---|
JP6546527B2 (ja) | 2019-07-17 |
CN106084184B (zh) | 2020-05-01 |
CN106084184A (zh) | 2016-11-09 |
TW201638175A (zh) | 2016-11-01 |
KR20160127665A (ko) | 2016-11-04 |
TWI693250B (zh) | 2020-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6546527B2 (ja) | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 | |
JP6192523B2 (ja) | エポキシ樹脂の硬化剤、製法、およびその用途 | |
JP5209556B2 (ja) | エポキシ樹脂組成物および成形物 | |
JP5079721B2 (ja) | エポキシ樹脂組成物および成形物 | |
JP6052868B2 (ja) | エポキシ樹脂の硬化剤、製法、およびその用途 | |
JP3509236B2 (ja) | エポキシ樹脂組成物及び半導体封止材料 | |
JP5681151B2 (ja) | エポキシ樹脂組成物および成形物 | |
JP5302147B2 (ja) | 封止用エポキシ樹脂組成物および硬化物 | |
JP4407885B2 (ja) | フェノキシシラン化合物、その製法、並びにそれを含むエポキシ樹脂組成物及びその硬化物 | |
JP5946329B2 (ja) | フェノール系オリゴマー、その製法及び用途 | |
JP6867894B2 (ja) | 組成物、エポキシ樹脂硬化剤、エポキシ樹脂組成物、熱硬化性組成物、硬化物、半導体装置、および層間絶縁材料 | |
JP5199847B2 (ja) | エポキシ樹脂組成物および成形物 | |
JP2006249139A (ja) | 半導体封止用エポキシ樹脂組成物 | |
JP2006117881A (ja) | エポキシ樹脂用添加剤、その組成物及びその用途 | |
JP4435342B2 (ja) | エポキシ樹脂組成物及び半導体封止用エポキシ樹脂組成物 | |
TWI835960B (zh) | 密封組成物及半導體裝置 | |
JP2003041118A (ja) | 半導体封止材用樹脂組成物 | |
JP2912468B2 (ja) | 樹脂組成物 | |
JPH04224859A (ja) | 樹脂組成物 | |
JPS6159328B2 (ja) | ||
JP2023093972A (ja) | エポキシ樹脂組成物および硬化物 | |
JP2023066807A (ja) | エポキシ樹脂組成物および硬化物 | |
JP2023118298A (ja) | エポキシ樹脂組成物および硬化物 | |
JPH03192113A (ja) | 半導体封止用樹脂組成物 | |
JP2010059261A (ja) | 難燃性成形用樹脂組成物および成形品 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180614 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190226 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190228 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190423 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190515 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190611 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190621 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6546527 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |