WO2011108588A1 - 硬化性樹脂組成物、及びその硬化物 - Google Patents
硬化性樹脂組成物、及びその硬化物 Download PDFInfo
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- WO2011108588A1 WO2011108588A1 PCT/JP2011/054767 JP2011054767W WO2011108588A1 WO 2011108588 A1 WO2011108588 A1 WO 2011108588A1 JP 2011054767 W JP2011054767 W JP 2011054767W WO 2011108588 A1 WO2011108588 A1 WO 2011108588A1
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- group
- resin composition
- curable resin
- epoxy resin
- alicyclic epoxy
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 105
- 239000003822 epoxy resin Substances 0.000 claims abstract description 130
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 130
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 79
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 74
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 39
- 239000004065 semiconductor Substances 0.000 claims abstract description 34
- -1 saturated aliphatic cyclic acid anhydride Chemical class 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 47
- 230000003287 optical effect Effects 0.000 claims description 44
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 37
- 239000004593 Epoxy Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 238000007789 sealing Methods 0.000 claims description 11
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- 238000005538 encapsulation Methods 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 2
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- 238000002156 mixing Methods 0.000 description 20
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- FWHUTKPMCKSUCV-UHFFFAOYSA-N 1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-carboxylic acid Chemical compound C1C(C(=O)O)CCC2C(=O)OC(=O)C12 FWHUTKPMCKSUCV-UHFFFAOYSA-N 0.000 description 7
- 239000003463 adsorbent Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 6
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- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
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- 150000002736 metal compounds Chemical class 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- QLPMKRZYJPNIRP-UHFFFAOYSA-M methyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC QLPMKRZYJPNIRP-UHFFFAOYSA-M 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 229910003465 moissanite Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- VGPSLAHKKFPLBQ-UHFFFAOYSA-N phosphane;tris(2-methylphenyl)phosphane Chemical class P.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C VGPSLAHKKFPLBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- JSSXHAMIXJGYCS-UHFFFAOYSA-N piperazin-4-ium-2-carboxylate Chemical compound OC(=O)C1CNCCN1 JSSXHAMIXJGYCS-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-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
- DCAFJGSRSBLEPX-UHFFFAOYSA-N tris(2,3-dibutylphenyl) phosphite Chemical compound CCCCC1=CC=CC(OP(OC=2C(=C(CCCC)C=CC=2)CCCC)OC=2C(=C(CCCC)C=CC=2)CCCC)=C1CCCC DCAFJGSRSBLEPX-UHFFFAOYSA-N 0.000 description 1
- OOZKMYBQDPXENQ-UHFFFAOYSA-N tris(2,3-diethylphenyl) phosphite Chemical compound CCC1=CC=CC(OP(OC=2C(=C(CC)C=CC=2)CC)OC=2C(=C(CC)C=CC=2)CC)=C1CC OOZKMYBQDPXENQ-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- QFGXDXGDZKTYFD-UHFFFAOYSA-N tris[2,3-di(propan-2-yl)phenyl] phosphite Chemical compound CC(C)C1=CC=CC(OP(OC=2C(=C(C(C)C)C=CC=2)C(C)C)OC=2C(=C(C(C)C)C=CC=2)C(C)C)=C1C(C)C QFGXDXGDZKTYFD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000013191 viscoelastic testing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- MFXMOUUKFMDYLM-UHFFFAOYSA-L zinc;dihydrogen phosphate Chemical compound [Zn+2].OP(O)([O-])=O.OP(O)([O-])=O MFXMOUUKFMDYLM-UHFFFAOYSA-L 0.000 description 1
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- 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
- H01L23/296—Organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Definitions
- Patent Document 4 an epoxy resin having an organopolysiloxane structure having a high crosslinking density (containing silicon atoms having three bonded oxygen atoms in a proportion exceeding 40 mol% per all silicon atoms). Attempts have been made to use alicyclic epoxy resins in combination. However, the composition described in Patent Document 4 has a high crosslinking density of the organopolysiloxane and a high content of the alicyclic epoxy resin, so that the cured product becomes too hard although it has excellent adhesion. It has been found that stress is easily applied to the chip when the LED is sealed. Further, it has been found that this causes a problem that illuminance deterioration during lighting is severe.
- LEDs using silicone resins or silicone-modified epoxy resins are generally poor in gas permeability resistance. Therefore, when a silicone resin or a silicone-modified epoxy resin is used as the LED sealing material, coloring on the LED chip is not a problem, but there is a problem that internal components are deteriorated and coloring occurs. . In particular, when used in a living environment, various compounds are floating, and the penetration of such compounds into the interior triggers problems.
- Patent Documents 5 and 6 use techniques such as coating a gas permeation-resistant protective agent and coating a metal part with an inorganic material. In addition to an increase in productivity and productivity, there is a problem in that light extraction efficiency is deteriorated due to a difference in refractive index between the covering portion and the sealant.
- the present invention has been made in view of the above prior art, and the object thereof is a curable resin capable of providing a cured product satisfying various physical properties required as an electrical semiconductor material application, particularly as an optical semiconductor sealing material. It is to provide a composition, specifically, it has excellent curability, adhesiveness, light resistance, heat resistance and gas permeability resistance, and resin stress to a chip when used as an LED sealing material.
- An object of the present invention is to provide a curable resin composition that can provide a cured product that is low in illuminance and does not cause illuminance deterioration.
- (2) Contains an epoxycyclohexyl group-containing organopolysiloxane (A), an alicyclic epoxy resin (B) and an acid anhydride (C), and includes an epoxycyclohexyl group-containing organopolysiloxane (A) and an alicyclic epoxy resin ( A curable resin composition, wherein the amount of the alicyclic epoxy resin (B) in the total amount of B) is 2 to 40% by weight.
- the content of the alicyclic epoxy resin (B) in the total amount of the epoxycyclohexyl group-containing organopolysiloxane (A) and the alicyclic epoxy resin (B) is 10 ⁇ (epoxycyclohexyl group-containing organopolysiloxane ( The curable resin composition according to (1) or (2), wherein the weight average molecular weight of A) / (epoxy equivalent of epoxycyclohexyl group-containing organopolysiloxane (A)) is not more than wt%. (4) The curable resin composition according to any one of (1) to (3) above, further comprising a polyvalent carboxylic acid (D).
- the above polyvalent carboxylic acid (D) is a compound obtained by reacting a bi- to hexafunctional polyhydric alcohol having 5 or more carbon atoms with a saturated aliphatic cyclic acid anhydride.
- Curable resin composition as described in (4).
- the epoxysiloxane group-containing organopolysiloxane (A) is a chain-like silicone moiety comprising dimethyl-substituted, diphenyl-substituted or a mixture thereof, and a three-dimensional condensate moiety having an epoxycyclohexyl group (silsesquioxane moiety).
- the curable resin composition according to any one of the above (1) to (6) which is a block-type compound having: (8) A cured product obtained by curing the curable resin composition according to any one of (1) to (7) above.
- a curable resin composition for optical semiconductor encapsulation comprising the curable resin composition according to any one of (1) to (7) above.
- An optical semiconductor device obtained by curing and sealing with the curable resin composition for optical semiconductor encapsulation described in (9) above.
- the curable resin composition of the present invention is useful for electrical and electronic material applications, particularly as an optical semiconductor sealing material, and has excellent curability, adhesiveness, light resistance, heat resistance, and gas permeability resistance, and an LED sealing material.
- the resin When used as a hardened material, the resin has little resin stress on the chip and does not cause illuminance deterioration.
- the curable resin composition of the present invention contains an epoxycyclohexyl group-containing organopolysiloxane (A), an alicyclic epoxy resin (B), and an acid anhydride (C).
- the epoxycyclohexyl group-containing organopolysiloxane (A) is an epoxy resin having an epoxycyclohexyl group in at least its molecule, and is generally synthesized by a sol-gel reaction using trialkoxysilane having an epoxycyclohexyl group as a raw material. Can do.
- Japanese Unexamined Patent Publication No. 2004-256609 Japanese Unexamined Patent Publication No.
- the block type siloxane compound (A1) is produced using, for example, an alkoxysilane compound (a) represented by the general formula (1) and a silicone oil (b) represented by the general formula (2) as raw materials as described below. If necessary, the alkoxysilane compound (c) represented by the general formula (3) can be used as a raw material.
- the chain silicone part of the block type siloxane compound (A1) is formed from silicone oil (b), and the three-dimensional network silsesquioxane part is alkoxysilane (a) (and, if necessary, alkoxysilane (c )).
- each raw material will be described in detail.
- the alkoxysilane compound (a) is represented by the following formula (1).
- X in the general formula (1) is not particularly limited as long as it is an organic group having an epoxycyclohexyl group.
- ⁇ - (3,4-epoxycyclohexyl) ethyl group ⁇ - (3,4-epoxycyclohexyl) propyl group
- ⁇ - (3,4-epoxycyclohexyl) propyl group ⁇ - (3,4-epoxycyclohexyl) propyl group
- ⁇ - (3,4-epoxycyclohexyl) examples thereof include an alkyl group having 1 to 5 carbon atoms substituted with a cyclohexyl group having an epoxy group such as a butyl group.
- an alkyl group having 1 to 3 carbon atoms substituted with a cyclohexyl group having an epoxy group is preferable, and a ⁇ - (3,4-epoxycyclohexyl) ethyl group is particularly preferable.
- a plurality of R 2 may be the same or different and each represents a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms.
- R 2 is preferably a methyl group or an ethyl group, and particularly preferably a methyl group, from the viewpoint of reaction conditions such as compatibility and reactivity.
- alkoxysilane (a) examples include ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltriethoxysilane, and the like. 3,4-epoxycyclohexyl) ethyltrimethoxysilane is preferred.
- These alkoxysilane compounds (a) may be used independently, may use 2 or more types, and can also be used together with the alkoxysilane (c) mentioned later.
- Silicone oil (b) is represented by the following formula (2)
- a plurality of R 3 may be the same or different from each other, and may be an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, or an alkenyl having 2 to 10 carbon atoms. Indicates a group.
- m represents the number of repetitions.
- alkyl group having 1 to 10 carbon atoms examples include linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, amyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, octyl group, 2-ethylhexyl Group, nonyl group, decyl group and the like.
- methyl group, ethyl group, cyclohexyl group and n-propyl group are preferable in consideration of light resistance.
- the aryl group having 6 to 14 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, and a xylyl group.
- the alkenyl group having 2 to 10 carbon atoms include alkenyl groups such as vinyl group, 1-methylvinyl group, allyl group, propenyl group, butenyl group, pentenyl group and hexenyl group.
- R 3 is preferably a methyl group, a phenyl group, a cyclohexyl group or an n-propyl group from the viewpoints of light resistance and heat resistance, and particularly preferably a methyl group or a phenyl group.
- those having a phenyl group in at least a part of the substituents are particularly preferable from the viewpoint of compatibility.
- m represents an average value of 3 to 200, preferably 3 to 100, more preferably 3 to 50.
- m represents an average value of 3 to 200, preferably 3 to 100, more preferably 3 to 50.
- the weight average molecular weight (Mw) of the silicone oil (b) is preferably in the range of 300 to 18,000 (measured by gel permeation chromatography (GPC)).
- GPC gel permeation chromatography
- those having a molecular weight of 300 to 10,000 are preferable in consideration of the elastic modulus at a low temperature, and those having a molecular weight of 300 to 5,000 are more preferable in consideration of compatibility at the time of forming the composition. 1,000 is preferred.
- the weight average molecular weight is less than 300, the properties of the chain silicone portion of the characteristic segment are difficult to be obtained, and the properties as a block type may be impaired.
- the molecular weight exceeds 18,000 a severe layer separation structure is formed.
- the molecular weight of the silicone oil (b) can be calculated by polystyrene conversion and weight average molecular weight (Mw) measured under the following conditions using GPC.
- the kinematic viscosity of the silicone oil (b) is preferably in the range of 10 to 200 cSt, more preferably 30 to 90 cSt.
- the viscosity is less than 10 cSt, the viscosity of the block type siloxane compound (A1) becomes too low and may not be suitable as an optical semiconductor sealing agent.
- the viscosity exceeds 200 cSt, the viscosity of the block type siloxane compound (A1) Is unfavorable because it tends to cause an adverse effect on workability.
- preferable silicone oil (b) examples include the following product names.
- PRX413 and BY16-873 are manufactured by Toray Dow Corning Silicone
- X-21-5841 and KF-9701 are manufactured by Shin-Etsu Chemical
- XC96-723, TSR160, YR3370 and YF3800 are manufactured by Momentive.
- XF3905 YF3057, YF3807, YF3802, YF3897, YF3804, XF3905, manufactured by Gelest, DMS-S12, DMS-S14, DMS-S15, DMS-S21, DMS-S27, DMS-S31, DMS-S32, DMS -S33, DMS-S35, DMS-S42, DMS-S45, DMS-S51, PDS-0332, PDS-1615, PDS-9931 and the like.
- PRX413, BY16-873, X-21-5841, KF-9701, XC96-723, YF3800, YF3804, DMS-S12, DMS-S14, DMS-S15, DMS-S21 PDS-1615 is preferred.
- X-21-5841, XC96-723, YF3800, YF3804, DMS-S14, and PDS-1615 are particularly preferable from the viewpoint of molecular weight in order to give the silicone site flexibility.
- These silicone oils (b) may be used alone or in combination of two or more.
- the alkoxysilane (c) has a structure of the following formula (3).
- preferable alkoxysilane (c) include methyltrimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, and phenyltriethoxysilane. Of these, methyltrimethoxysilane and phenyltrimethoxysilane are preferred.
- alkoxysilane (a) which is a silicon compound having an alkoxy group as production step (ii) (and alkoxysilane (c) added if necessary), and alkoxy of the silicone oil obtained in production step (i)
- a method for producing a block-type siloxane compound (A1) by passing water through the silane-modified product (d) and subjecting it to a hydrolytic condensation reaction between alkoxy groups.
- a production step (ii) an alkoxy group in the molecule is obtained by performing a hydrolysis-condensation reaction between alkoxy groups by adding water of alkoxysilane (a) (and alkoxysilane (c) added as necessary).
- silsesquioxane (e) which has this is performed. Then, through a reaction of silicone oil (b) and silsesquioxane (e) as a production step (i), a step of dealcoholization condensation reaction of the alkoxy group and silanol group remaining in the silsesquioxane structure, A method for producing a block-type siloxane compound (A1).
- a silicone oil is obtained by a dealcoholization condensation reaction between a silicone oil (b) having a silanol group at the terminal and an alkoxysilane (a) (and an alkoxysilane (c) added as necessary).
- the dealcohol condensation of the silicone oil (b) and the alkoxysilane (a) (and the alkoxysilane (c) added if necessary) is performed, and the terminal of the silicone oil is obtained.
- the body (d) is considered to exist in a structure represented by the following formula (4).
- R 2 , R 3 and m have the same meaning as described above, and R 6 represents X and / or R 4. )
- a second-stage reaction (production step (ii)) is performed in which water is added as it is to hydrolyze and condense alkoxy groups.
- the following reactions (I) to (III) occur.
- (I) A condensation reaction between alkoxy groups of the alkoxysilane (a) remaining in the system (and the alkoxysilane (c) added if necessary).
- (II) A condensation reaction between the alkoxy groups of the alkoxysilane-modified product (d) obtained in the production step (i) and the alkoxysilane (a) (and the alkoxysilane (c) added as necessary).
- the production of the block type siloxane compound (A1) can be carried out without a catalyst, but if it is no catalyst, the reaction proceeds slowly, and it is preferably carried out in the presence of a catalyst from the viewpoint of shortening the reaction time.
- a catalyst any compound that exhibits acidity or basicity can be used.
- the acidic catalyst include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, and organic acids such as formic acid, acetic acid and oxalic acid.
- Examples of basic catalysts include sodium hydroxide, potassium hydroxide, lithium hydroxide, alkali metal hydroxides such as cesium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.
- the catalyst As a method for adding the catalyst, it is added directly or used in a state dissolved in a soluble solvent or the like. Among them, it is preferable to add the catalyst in a state in which the catalyst is dissolved in advance in alcohols such as methanol, ethanol, propanol and butanol. At this time, adding as an aqueous solution using water or the like causes the condensation of the alkoxysilane (a) (and the alkoxysilane (c) to be added as necessary) unilaterally as described above, The silsesquioxane oligomer produced thereby and the silicone oil (b) may not be compatible with each other and may become cloudy.
- alcohols such as methanol, ethanol, propanol and butanol.
- the production of the block type siloxane compound (A1) can be carried out without solvent or in a solvent. Moreover, a solvent can also be added in the middle of a manufacturing process.
- the solvent for use is not particularly limited as long as it is a solvent that dissolves alkoxysilane (a), alkoxysilane (c), silicone oil (b), and alkoxysilane-modified product (d).
- reaction in alcohols is preferable from the viewpoint of reaction control, and methanol and ethanol are more preferable.
- the amount of solvent used is not particularly limited as long as the reaction proceeds smoothly, but alkoxysilane (a) (and alkoxysilane (c) added as necessary), a compound of silicone oil (b) Usually, about 0 to 900 parts by weight is used with respect to 100 parts by weight.
- the reaction temperature is usually 20 to 160 ° C., preferably 40 to 140 ° C., particularly preferably 50 to 150 ° C., depending on the amount of catalyst.
- the reaction time is usually 1 to 40 hours, preferably 5 to 30 hours, in each production step.
- the catalyst is removed by quenching and / or washing with water as necessary.
- a solvent that can be separated from water.
- Preferred solvents include ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclopentanone, esters such as ethyl acetate, butyl acetate, ethyl lactate and isopropyl butanoate, hydrocarbons such as hexane, cyclohexane, toluene and xylene. Can be illustrated.
- the catalyst may be removed only by washing with water, but the reaction is carried out under acidic or basic conditions. It is preferable to remove the adsorbent by filtration after adsorbing the catalyst using Any compound that exhibits acidity or basicity can be used for the neutralization reaction.
- the compound exhibiting acidity include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, and organic acids such as formic acid, acetic acid and oxalic acid.
- Examples of compounds showing basicity include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide and cesium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
- Inorganic bases such as alkali metal carbonates, phosphoric acid, sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, phosphates such as polyphosphoric acid, sodium tripolyphosphate, ammonia, triethylamine, diethylenetriamine, n-butylamine, Organic bases such as dimethylaminoethanol, triethanolamine, and tetramethylammonium hydroxide can be used.
- inorganic bases or inorganic acids are preferable because they can be easily removed from the product, and phosphates that can more easily adjust the pH to near neutral are more preferable.
- adsorbent examples include activated clay, activated carbon, zeolite, inorganic / organic synthetic adsorbent, ion exchange resin, and the like, and specific examples include the following products.
- activated clay for example, Toshin Kasei Co., Ltd., activated clay SA35, SA1, T, R-15, E, Nikkanite G-36, G-153, G-168 are manufactured by Mizusawa Chemical Co., Ltd. Galeon Earth, Mizuka Ace, etc. are listed.
- a synthetic adsorbent for example, Kyoward 100, 200, 300, 400, 500, 600, 700, 1000, 2000 manufactured by Kyowa Chemical Co., Ltd., Amberlist 15JWET, 15DRY, manufactured by Rohm and Haas Co., Ltd. 16WET, 31WET, A21, Amberlite IRA400JCl, IRA403BLCl, IRA404JCl, Dow Chemical Co., Dowex 66, HCR-S, HCR-W2, MAC-3, and the like.
- the adsorbent is added to the reaction solution, followed by treatment such as stirring and heating to adsorb the catalyst, and then the adsorbent is filtered and the residue is washed with water to remove the catalyst and adsorbent.
- the molecular weight is the equivalent ratio of alkoxysilane (a) (and optionally added alkoxysilane (c)) to silicone oil (b), the molecular weight of silicone oil (b), the amount of water added during the reaction, The reaction time and reaction temperature can be adjusted.
- the weight average molecular weight is a polystyrene equivalent weight average molecular weight (Mw) measured using GPC (gel permeation chromatography) under the following conditions.
- the ratio of silicon atoms bonded to three oxygens derived from silsesquioxane in the block type siloxane compound (A1) to the total silicon atoms is preferably 8 to 30 mol%, more preferably 8 to 25 mol%.
- the ratio of silicon atoms bonded to three oxygens derived from silsesquioxane with respect to all silicon atoms is less than 8 mol%, the characteristics of the chain silicone sites appear and the cured product tends to be too soft. .
- it exceeds 30 mol% the characteristic of the silsesquioxane structure site
- the epoxycyclohexyl group-containing organopolysiloxane (A) and the block type siloxane compound (A1) in the present invention preferably include a phenyl skeleton in the structure.
- the phenyl skeleton is introduced into the block-type siloxane compound (A1), it is contained in at least one of silicone oil (b) and alkoxysilane (a) (and alkoxysilane (c) added if necessary). It only has to be.
- the strength and refractive index of the cured product are improved.
- the refractive index the light extraction efficiency is improved when used as an optical semiconductor sealing material.
- the phenyl skeleton also has an effect of filling a space between molecules and preventing gas permeation.
- epoxy resins include esterification reaction of cyclohexene carboxylic acid and alcohols or esterification reaction of cyclohexene methanol and carboxylic acids (Tetrahedron vol.36 p.2409 (1980), Tetrahedron Letter p.4475 (1980), etc.) Described), or Tyschenko reaction of cyclohexene aldehyde (method described in Japanese Patent Application Laid-Open No. 2003-170059, Japanese Patent Application Laid-Open No.
- Examples of carboxylic acids include, but are not limited to, oxalic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, adipic acid, and cyclohexanedicarboxylic acid.
- the acetal compound by the acetal reaction of a cyclohexene aldehyde derivative and an alcohol form is mentioned.
- these epoxy resins include ERL-4221, UVR-6105, ERL-4299 (all trade names, all manufactured by Dow Chemical), Celoxide 2021P, Epolide GT401, EHPE3150, EHPE3150CE (all trade names, all Daicel) (Chemical Industry) and dicyclopentadiene diepoxide, and the like, but are not limited to these (Reference: Review Epoxy Resin Basic Edition I p76-85). These may be used alone or in combination of two or more.
- a compound having an epoxycyclohexane structure is also preferable from the viewpoint of improving gas permeability resistance.
- the epoxy equivalent (measured by the method described in JIS K-7236) of the alicyclic epoxy resin (B) is 100 to 500 g / eq. And preferably 100 to 300 g / eq. Are more preferred.
- the content of the alicyclic epoxy resin (B) is less than 1.5% by weight, the resulting cured product is brittle, has a high linear expansion coefficient, and has poor adhesion, and as an optical semiconductor sealing material Inferior to suitability.
- the content of the alicyclic epoxy resin (B) is more preferably 1.7 to 20% by weight, and particularly preferably 1.8 to 20% by weight. Further, when the content of the alicyclic epoxy resin is increased, the content of the alicyclic epoxy resin (B) is more preferably 5 to 20% by weight, particularly preferably 10 to 20% by weight.
- the quantity ratio can be determined by the epoxy equivalent of each other.
- the dispersibility of the epoxy group contained in the organopolysiloxane (A) it has been found that a cured product having a balance between hardness and flexibility and excellent light extraction efficiency can be obtained.
- the epoxy group dispersibility of the epoxycyclohexyl group-containing organopolysiloxane (A) refers to the weight average molecular weight of the epoxycyclohexyl group-containing organopolysiloxane (A) and the epoxycyclohexyl group-containing organopolysiloxane (A). It means a value divided by an epoxy equivalent (amount of resin containing 1 g equivalent of epoxy (unit: g / eq.)), Whereby the average of epoxy groups contained in one molecule of epoxycyclohexyl group-containing organopolysiloxane (A) The amount can be estimated.
- the flexibility derived from the chain silicone moiety is effectively expressed, the cured product has a better balance between hardness and flexibility, and has improved light extraction efficiency. It is possible to obtain According to the above formula, the greater the amount of epoxy groups per molecule, the greater the amount of alicyclic epoxy resin (B) introduced. On the other hand, the smaller the amount of epoxy groups per molecule, the smaller the amount of alicyclic epoxy resin (B) introduced.
- the ratio P calculated from the above formula is desirably 40 or less (that is, the maximum content of the alicyclic epoxy resin (B) is 40% by weight or less). However, the ratio P is an amount within the range of 1.5 to 40% by weight described above. Preferably, the alicyclic epoxy resin (B) is 1.5 to 20% by weight and the ratio P is 40 or less.
- the curable resin composition of the present invention contains an acid anhydride (C) as a curing agent.
- the acid anhydride (C) is excellent in transparency and is excellent in workability because it is liquid.
- Specific examples of acid anhydrides include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, hexahydrophthalic anhydride Acid, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2,2,1] heptane-2,3-dicarboxylic anhydride, methylbicyclo [2,2,1] heptane-2,3- And acid anhydrides such as dicarboxylic acid anhydride and cyclohexane-1,2,4-tricarboxylic acid-1,
- hexahydrophthalic anhydride methylhexahydrophthalic anhydride, cyclohexane-1,2,4-tricarboxylic acid- 1,2-anhydride is preferable, and methylhexahydrophthalic anhydride and cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride are particularly preferable.
- the amount of the acid anhydride (C) used in the curable resin composition of the present invention is preferably 0.7 to 1.2 equivalents relative to 1 equivalent of the epoxy groups of all epoxy resins. When less than 0.7 equivalent or more than 1.2 equivalent with respect to 1 equivalent of epoxy group, curing may be incomplete and good cured properties may not be obtained. When used in combination with a curing agent such as a polyvalent carboxylic acid to be described later, the total amount of the curing agent used is preferably within the above range.
- the acid anhydride (C) is preferably used in combination with the polyvalent carboxylic acid (D) which is another curing agent, and the content when used in combination with the polyvalent carboxylic acid (D) described later is It is desirable to be determined by a ratio, and the range of the following formula is preferable.
- W1 / (W1 + W2) 0.05-0.70 (W1 represents a blended part by weight of the polyvalent carboxylic acid (D), and W2 represents a blended part by weight of the acid anhydride (C).)
- the range of W1 / (W1 + W2) is more preferably 0.05 to 0.60, still more preferably 0.10 to 0.55, and particularly preferably 0.15 to 0.4.
- the polyvalent carboxylic acid (D) used in the present invention is desirably a compound having at least two or more carboxyl groups and having an aliphatic hydrocarbon group as a main skeleton.
- the polyvalent carboxylic acid is not only a polyvalent carboxylic acid having a single structure, but also a mixture of a plurality of compounds having different substituent positions or different substituents, that is, a polyvalent carboxylic acid composition. In the present invention, they are collectively referred to as a polyvalent carboxylic acid.
- a bi- to hexa-functional carboxylic acid is particularly preferable, and a compound obtained by reacting a bi- to hexa-functional polyhydric alcohol having 5 or more carbon atoms with an acid anhydride is more preferable.
- the polycarboxylic acid whose said acid anhydride is a saturated aliphatic cyclic acid anhydride is preferable.
- the bi- to hexafunctional polyhydric alcohol is not particularly limited as long as it is a compound having an alcoholic hydroxyl group, but ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol.
- 2-ethyl-2 -Branched chain structures such as butyl-1,3-propanediol, neopentyl glycol, 2,4-diethylpentanediol, 1,4-cyclohexanedimethanol, tricyclodecane dimethanol, norbornenediol, carbinol-modified silicone oil Or ring Concrete, more preferably polyhydric alcohols having a siloxane structure.
- carbinol-modified silicone oil is specifically the following formula (4A)
- R 8 represents an alkylene group having 1 to 10 carbon atoms
- R 7 represents a methyl group or a phenyl group
- p represents an average value of 1 to 100.
- a plurality of Q's represent at least one of a hydrogen atom, a methyl group and a carboxyl group.
- P is a chain-like, cyclic aliphatic group having 2 to 20 carbon atoms derived from the aforementioned polyhydric alcohol. .
- m is preferably from 1 to 7, particularly preferably from 2 to 6.
- the ratio of phosphorus atom to zinc atom is preferably 1.2 to 2.3, more preferably 1.3 to 2.0. . Particularly preferred is 1.4 to 1.9. That is, in a particularly preferred form, the amount of phosphate ester (or phosphate derived from phosphate ester) is 2.0 moles or less per mole of zinc ion, and not a simple ionic structure, some molecules are ion-bonded (or arranged). Those having a structure related by coordinate bond are preferred.
- Such a zinc salt and / or zinc complex can also be obtained, for example, by the technique described in Japanese Patent Publication No. 2003-51495.
- the content of the zinc salt and / or the zinc complex (E) is zinc relative to the total amount of the epoxycyclohexyl group-containing organopolysiloxane (A) and the alicyclic epoxy resin (B).
- the salt and / or zinc complex (E) is 0.01 to 8% by weight, more preferably 0.05 to 5% by weight, and further 0.1 to 4% by weight. Further, it is particularly preferably 0.1 to 2% by weight.
- the curable resin composition of the present invention when used in an optical material, particularly an optical semiconductor encapsulant, it contains a hindered amine compound as a light stabilizer and a phosphorus compound as an antioxidant as particularly preferable components. That is preferred.
- the light stabilizer is used in an amount of 0.005 to 5 by weight with respect to the total amount of the epoxycyclohexyl group-containing organopolysiloxane (A) and the alicyclic epoxy resin (B). % By weight, more preferably 0.01 to 4% by weight, and 0.1 to 2% by weight.
- the phosphorus compound is used in an amount of 0.005 to 5 by weight with respect to the total amount of the epoxycyclohexyl group-containing organopolysiloxane (A) and the alicyclic epoxy resin (B). % By weight, more preferably 0.01 to 4% by weight, and 0.1 to 2% by weight.
- the curable resin composition of the present invention includes an epoxycyclohexyl group-containing organopolysiloxane (A) and an alicyclic epoxy resin (B) as an epoxy resin, and an acid anhydride (C) and a polyvalent carboxylic acid (D) as a curing agent. It is preferable to contain.
- the curable resin composition of the present invention comprises an epoxycyclohexyl group-containing organopolysiloxane (A) and an alicyclic epoxy resin (B) as an epoxy resin, and an acid anhydride (C) and a polyvalent carboxylic acid (as a curing agent). D) It is preferable to contain a zinc salt and / or a zinc complex (E) as an additive.
- the curable resin composition of the present invention preferably contains a hindered amine light stabilizer and a phosphorus-containing antioxidant as additives. These can be used in combination with other epoxy resins, curing agents and various additives described below.
- epoxy resin component other epoxy resins that can be used in combination with the epoxycyclohexyl group-containing organopolysiloxane (A) and the alicyclic epoxy resin (B) include novolac type epoxy resins, bisphenol A type epoxy resins, biphenyl type epoxy resins, A triphenylmethane type epoxy resin, a phenol aralkyl type epoxy resin, etc. are mentioned.
- curing agents that can be used include amines and polyamide compounds (diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, polyamide resin synthesized from ethylenediamine and dimer of linolenic acid, etc.) , Reaction product of acid anhydride and silicone alcohol (phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, anhydrous Nadic acid, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2,2,1] heptane-2,3-dicarboxylic anhydride, methylbicyclo [2,2,2,
- the curable resin composition of the present invention may contain various additives and auxiliary materials as listed below.
- the curable resin composition of the present invention may contain a phosphorus-containing compound as a flame retardant component.
- the phosphorus-containing compound may be a reactive type or an additive type.
- a binder resin can be blended with the curable resin composition of the present invention as required.
- the binder resin include butyral resins, acetal resins, acrylic resins, epoxy-nylon resins, NBR-phenol resins, epoxy-NBR resins, polyamide resins, polyimide resins, and silicone resins.
- the blending amount of the binder resin is preferably in a range that does not impair the flame retardancy and heat resistance of the cured product, and is usually 0.1% relative to 100 parts by weight of the epoxy resin component and the curing agent component contained in the curable resin composition. 05 to 50 parts by weight, preferably 0.05 to 20 parts by weight are used as necessary.
- a silane coupling agent a release agent such as stearic acid, palmitic acid, zinc stearate, and calcium stearate, various compounding agents such as pigments, and various thermosetting resins are added to the curable resin composition of the present invention. can do.
- the particle size of the inorganic filler used is transparent by using a nano-order level filler. It is possible to supplement the mechanical strength and the like without hindering.
- the addition amount thereof is 1 to 80 parts by weight, preferably 5 parts per 100 parts by weight of the organic component such as epoxycyclohexyl group-containing organopolysiloxane (A). ⁇ 60 parts by weight is preferred.
- silica fine powder also called Aerosil or Aerosol
- a thixotropic agent can be added.
- silica fine powder include Aerosil 50, Aerosil 90, Aerosil 130, Aerosil 200, Aerosil 300, Aerosil 380, Aerosil OX50, Aerosil TT600, Aerosil R972, Aerosil R974, AerosilR202, AerosilR202, AerosilR202 Aerosil R805, RY200, RX200 (made by Nippon Aerosil Co., Ltd.), etc. are mentioned.
- TINUVIN 328, TINUVIN 234, TINUVIN 326, TINUVIN 120, TINUVIN 477, TINUVIN 479, CHIMASSORB 2020FDL, CHIMASSORB 119FL, and the like are manufactured by Ciba Specialty Chemicals.
- the obtained curable resin composition of the present invention When the obtained curable resin composition of the present invention is in a liquid state, potting, casting, impregnating the base material, pouring the curable resin composition into a mold, casting, and curing by heating Let Further, when the obtained curable resin composition of the present invention is solid, it is molded using a cast after casting or a transfer molding machine, and further cured by heating. In addition, what is necessary is just to add and mix the hardening accelerator, an amine compound, a phosphorus containing compound, a phenol compound, binder resin, an inorganic filler, etc. which are arbitrary components at the said mixing process. The curing temperature and time are 80 to 200 ° C. and 2 to 10 hours.
- the curable resin composition of the present invention is dissolved in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc. to obtain a curable resin composition varnish, glass fiber,
- a prepreg obtained by impregnating a base material such as carbon fiber, polyester fiber, polyamide fiber, alumina fiber, paper, etc. and heat-dried is subjected to hot press molding to obtain a cured product of the curable resin composition of the present invention. can do.
- the curable resin composition of the present invention is used as a sealing material for an optical semiconductor such as a high-intensity white LED, or a die bond material, an epoxy resin, a curing agent, a coupling agent, an antioxidant, a light stabilizer, etc.
- An epoxy resin composition is prepared by thoroughly mixing the additives, and is used as a sealing material or for both a die bond material and a sealing material.
- a mixing method a kneader, a three-roll, a universal mixer, a planetary mixer, a homomixer, a homodisper, a bead mill or the like is used to mix at room temperature or warm.
- the curable resin composition of the present invention is applied by dispenser, potting, or screen printing, and then heated by placing the semiconductor chip thereon. Curing can be performed to bond the semiconductor chip.
- methods such as hot air circulation, infrared rays and high frequency can be used.
- the curable resin composition of the present invention can be used for general applications in which curable resins such as epoxy resins are used.
- curable resins such as epoxy resins
- adhesives examples include civil engineering, architectural, automotive, general office and medical adhesives, as well as electronic material adhesives.
- adhesives for electronic materials include interlayer adhesives for multilayer substrates such as build-up substrates, die bonding agents, semiconductor adhesives such as underfills, BGA reinforcing underfills, anisotropic conductive films ( ACF) and an adhesive for mounting such as anisotropic conductive paste (ACP).
- sealing agents potting, dipping, transfer mold sealing for capacitors, transistors, diodes, light-emitting diodes, ICs, LSIs, potting sealings for ICs, LSIs such as COB, COF, TAB, flip chip
- underfill for QFP, BGA, CSP, etc., and sealing can be used.
- the cured product obtained in the present invention can be used for various applications including optical component materials.
- the optical material refers to general materials used for applications that allow light such as visible light, infrared light, ultraviolet light, X-rays, and lasers to pass through the material. More specifically, in addition to LED sealing materials such as lamp type and SMD type, the following may be mentioned. It is a peripheral material for liquid crystal display devices such as a substrate material, a light guide plate, a prism sheet, a deflection plate, a retardation plate, a viewing angle correction film, an adhesive, and a film for a liquid crystal such as a polarizer protective film in the liquid crystal display field.
- color PDP plasma display
- antireflection films antireflection films
- optical correction films housing materials
- front glass protective films front glass replacement materials
- adhesives and LED displays that are expected as next-generation flat panel displays
- LED molding materials LED sealing materials, front glass protective films, front glass substitute materials, adhesives, and substrate materials for plasma addressed liquid crystal (PALC) displays, light guide plates, prism sheets, deflection plates , Phase difference plate, viewing angle correction film, adhesive, polarizer protective film, front glass protective film in organic EL (electroluminescence) display, front glass substitute material, adhesive, and various in field emission display (FED) Film substrate
- PLC plasma addressed liquid crystal
- VD video disc
- CD / CD-ROM CD-R / RW
- DVD-R / DVD-RAM MO / MD
- PD phase change disc
- disc substrate materials for optical cards Pickup lenses, protective films, sealing materials, adhesives and the like.
- optical equipment field they are still camera lens materials, finder prisms, target prisms, finder covers, and light receiving sensor parts. It is also a photographic lens and viewfinder for video cameras.
- optical components they are fiber materials, lenses, waveguides, element sealing materials, adhesives and the like around optical switches in optical communication systems.
- optical passive components and optical circuit components there are lenses, waveguides, LED sealing materials, CCD sealing materials, adhesives, and the like.
- OEIC optoelectronic integrated circuit
- automotive lamp reflectors In the field of automobiles and transport equipment, automotive lamp reflectors, bearing retainers, gear parts, anti-corrosion coatings, switch parts, headlamps, engine internal parts, electrical parts, various interior and exterior parts, drive engines, brake oil tanks, and automotive defenses Rusted steel plate, interior panel, interior material, wire harness for protection / bundling, fuel hose, automobile lamp, glass substitute.
- it is a multilayer glass for railway vehicles.
- they are toughness imparting agents for aircraft structural materials, engine peripheral members, protective / bundling wire harnesses, and corrosion-resistant coatings.
- it In the construction field, it is interior / processing materials, electrical covers, sheets, glass interlayers, glass substitutes, and solar cell peripheral materials. For agriculture, it is a house covering film.
- optical / electronic functional organic materials include organic EL element peripheral materials, organic photorefractive elements, optical amplification elements that are light-to-light conversion devices, optical arithmetic elements, substrate materials around organic solar cells, fiber materials, elements Sealing material, adhesive and the like.
- each physical property value in an Example was measured with the following method.
- GPC gel permeation chromatography
- Various conditions of GPC Manufacturer Shimadzu Corporation Column: Guard column SHODEX GPC LF-G LF-804 (3) Flow rate: 1.0 ml / min. Column temperature: 40 ° C
- Solvent THF (tetrahydrofuran)
- Detector RI (differential refraction detector)
- Epoxy equivalent Measured by the method described in JIS K-7236.
- the epoxy equivalent of the obtained compound (S-1) was 605 g / eq.
- the weight average molecular weight was 2120, and the appearance was a colorless and transparent liquid resin.
- the value of the ratio P was 35, and the ratio of silicon atoms bonded to three oxygens derived from silsesquioxane to all silicon atoms was about 18 mol%.
- the epoxy equivalent of the obtained compound (S-3) was 636 g / eq.
- the weight average molecular weight was 2090, and the appearance was a colorless and transparent liquid resin.
- the value of the ratio P was 33, and the ratio of silicon atoms bonded to three oxygens derived from silsesquioxane to all silicon atoms was about 17 mol%.
- the curing condition is 140 ° C. ⁇ 5 hours after 110 ° C. ⁇ 2 hours of preliminary curing.
- the curing agent composition (H-1) obtained in Synthesis Example 6 was synthesized.
- Curing agent composition (H-2) obtained in Example 7 phosphate ester zinc complex (C-2) as curing accelerator, hindered amine (L-1) as light stabilizer, antioxidant (O-1
- the curable resin compositions of Examples 4 to 6 and Comparative Example 5 were obtained by blending at a blending ratio (parts by weight) shown in Table 3 below and defoaming for 20 minutes. Furthermore, the obtained curable resin composition was cured in the following manner, and the transmittance and light resistance were evaluated.
- the curable resin composition of the present invention exhibited high illuminance retention even in an accelerated test in which an excessive current was passed at high temperature and high humidity, and had high characteristics as an LED.
- the curable resin compositions of Examples 9 to 11 and Comparative Examples 6 and 7 were obtained by blending at a blending ratio (parts by weight) shown in Table 5 below and performing defoaming for 20 minutes. It was.
- the curable resin compositions of the examples do not discolor the lead frame silver plating as compared with the curable resin compositions of the comparative examples (containing a polysiloxane compound and an acid anhydride). It was found that it was excellent in long-term corrosion gas resistance.
- Synthesis example B To a flask equipped with a stirrer, a reflux condenser, a stirrer, and a Dean-Stark tube, while purging with nitrogen, 150 parts of toluene and 2,4-diethyl-1,5-pentanediol (Kyowa Hakko Chemical Co., Ltd. Kyowa All PD9) ) 80 parts, 126 parts of 3-cyclohexenecarboxylic acid and 2 parts of paratoluenesulfonic acid were added, and the reaction was carried out under heating and refluxing for 10 hours while removing water.
- the diolefin compound of the present invention is washed twice with 50 parts of a 10% aqueous sodium hydrogen carbonate solution, the organic layer obtained is washed twice with 50 parts of water, and then the organic solvent is concentrated with a rotary evaporator. 187 parts of (D-1) was obtained.
- the shape was liquid, the purity by gas chromatography was 96%, and the result of analysis by gel permeation chromatography confirmed that the purity was> 98%.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
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JP2011256326A (ja) * | 2010-06-11 | 2011-12-22 | Nippon Kayaku Co Ltd | 硬化性樹脂組成物およびその硬化物 |
JP2012077219A (ja) * | 2010-10-04 | 2012-04-19 | Nippon Steel Chem Co Ltd | エポキシシリコーン樹脂含有硬化性樹脂組成物 |
JP2012087249A (ja) * | 2010-10-21 | 2012-05-10 | Nippon Kayaku Co Ltd | 硬化性樹脂組成物およびその硬化物 |
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JP2014056924A (ja) * | 2012-09-12 | 2014-03-27 | Hitachi Chemical Co Ltd | 半導体装置の製造方法及びそれに用いる熱硬化性樹脂組成物並びにそれらにより得られる半導体装置 |
JP2014080587A (ja) * | 2012-09-21 | 2014-05-08 | Nippon Kayaku Co Ltd | 透明接着材料 |
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JP2011256326A (ja) * | 2010-06-11 | 2011-12-22 | Nippon Kayaku Co Ltd | 硬化性樹脂組成物およびその硬化物 |
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JP2013057001A (ja) * | 2011-09-08 | 2013-03-28 | Mitsubishi Chemicals Corp | 熱硬化性樹脂組成物、半導体デバイス用部材、及びそれを用いた半導体デバイス |
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JP2014056924A (ja) * | 2012-09-12 | 2014-03-27 | Hitachi Chemical Co Ltd | 半導体装置の製造方法及びそれに用いる熱硬化性樹脂組成物並びにそれらにより得られる半導体装置 |
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JPWO2015056723A1 (ja) * | 2013-10-16 | 2017-03-09 | 日本化薬株式会社 | 硬化性樹脂組成物およびその硬化物 |
KR102188989B1 (ko) * | 2013-10-16 | 2020-12-09 | 닛뽄 가야쿠 가부시키가이샤 | 경화성 수지 조성물 및 그 경화물 |
WO2016052212A1 (ja) * | 2014-10-02 | 2016-04-07 | 株式会社ダイセル | ナノインプリント用光硬化性組成物 |
JP2016164254A (ja) * | 2015-02-10 | 2016-09-08 | 株式会社ダイセル | 光学材料用硬化性エポキシ樹脂組成物 |
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JP5878862B2 (ja) | 2016-03-08 |
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TWI538959B (zh) | 2016-06-21 |
CN102791760A (zh) | 2012-11-21 |
TW201137044A (en) | 2011-11-01 |
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