WO2011016356A1 - アクリレート系組成物 - Google Patents
アクリレート系組成物 Download PDFInfo
- Publication number
- WO2011016356A1 WO2011016356A1 PCT/JP2010/062551 JP2010062551W WO2011016356A1 WO 2011016356 A1 WO2011016356 A1 WO 2011016356A1 JP 2010062551 W JP2010062551 W JP 2010062551W WO 2011016356 A1 WO2011016356 A1 WO 2011016356A1
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- WO
- WIPO (PCT)
- Prior art keywords
- meth
- group
- acrylate
- component
- composition
- Prior art date
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- -1 acrylate compound Chemical class 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 229920002545 silicone oil Polymers 0.000 claims abstract description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 6
- 239000004065 semiconductor Substances 0.000 claims description 19
- 239000003566 sealing material Substances 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 14
- 229920001195 polyisoprene Polymers 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 239000005062 Polybutadiene Substances 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 229920002857 polybutadiene Polymers 0.000 claims description 7
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000686 lactone group Chemical group 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000000565 sealant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 35
- 238000011156 evaluation Methods 0.000 description 19
- 239000003963 antioxidant agent Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000010954 inorganic particle Substances 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
- 229910002601 GaN Inorganic materials 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [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])* 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
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- YAGPRJYCDKGWJR-UHFFFAOYSA-N 2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxy-n,n-bis[2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyethyl]ethanamine Chemical compound O1C2=C(C(C)(C)C)C=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP1OCCN(CCOP1OC2=C(C=C(C=C2C=2C=C(C=C(C=2O1)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)CCOP(OC1=C(C=C(C=C11)C(C)(C)C)C(C)(C)C)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C YAGPRJYCDKGWJR-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- PVGPIIDONDPCTG-UHFFFAOYSA-N C1CO1.CC1(C)CO[SiH2]O1 Chemical compound C1CO1.CC1(C)CO[SiH2]O1 PVGPIIDONDPCTG-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- DCTLJGWMHPGCOS-UHFFFAOYSA-N Osajin Chemical compound C1=2C=CC(C)(C)OC=2C(CC=C(C)C)=C(O)C(C2=O)=C1OC=C2C1=CC=C(O)C=C1 DCTLJGWMHPGCOS-UHFFFAOYSA-N 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004283 Sodium sorbate Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- VBQCFYPTKHCPGI-UHFFFAOYSA-N 1,1-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CCCCC1 VBQCFYPTKHCPGI-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- WAVTZYKJTMZICQ-UHFFFAOYSA-N 2-(2-methylbutan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCC(C)(C)OOC(C)(C)OC(O)=O WAVTZYKJTMZICQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- IEQWWMKDFZUMMU-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CCOC(=O)C=C IEQWWMKDFZUMMU-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- XRIRVAYMWUMXBR-UHFFFAOYSA-N 2-hydroperoxypentane Chemical compound CCCC(C)OO XRIRVAYMWUMXBR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- RTEZVHMDMFEURJ-UHFFFAOYSA-N 2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)C(C)(C)C RTEZVHMDMFEURJ-UHFFFAOYSA-N 0.000 description 1
- RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 1
- CHUZUQHNICURQV-UHFFFAOYSA-N 2-tert-butylperoxy-5-(2-tert-butylperoxypropan-2-yl)-2-methyloctane Chemical compound CC(C)(C)OOC(C)(C)C(CCC)CCC(C)(C)OOC(C)(C)C CHUZUQHNICURQV-UHFFFAOYSA-N 0.000 description 1
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- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000001802 myricyl 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])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
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- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/048—Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0203—Containers; Encapsulations, e.g. encapsulation of photodiodes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0232—Optical elements or arrangements associated with the device
- H01L31/02325—Optical elements or arrangements associated with the device the optical elements not being integrated nor being directly associated with the device
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- 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
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- 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
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/12—Passive devices, e.g. 2 terminal devices
- H01L2924/1204—Optical Diode
- H01L2924/12044—OLED
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Definitions
- the present invention relates to a composition containing an acrylate compound, and more particularly to a composition suitably used as a raw material for a sealing material, a lens and the like and a cured product thereof.
- optical semiconductor devices each having a light-emitting element with an LED (light-emitting diode) chip having a pn bond formed by a semiconductor layer grown on a crystal substrate and using this junction region as a light-emitting layer Widely used in display devices and display devices.
- this optical semiconductor device include a visible light emitting device and a high-temperature operating electronic device using a gallium nitride compound semiconductor such as GaN, GaAlN, InGaN, and InAlGaN. Recently, blue light emitting diodes and ultraviolet light emitting diodes are used. Development is progressing in this field.
- An optical semiconductor device including an LED chip as a light emitting element includes an LED chip mounted on a light emitting surface side of a lead frame, and electrically connecting the LED chip and the lead frame by wire bonding. It is sealed with a resin that also functions as a lens.
- white LEDs have attracted attention as a new light source, and it is said that the market will greatly expand in the future, mainly for lighting applications.
- YAG phosphor is applied to a GaN bare chip, and the blue light emission of GaN and the yellow light emission of the phosphor are mixed to emit white light, and the red, green and blue chips are packaged in one package to emit white light.
- a method of combining a plurality of phosphor materials using an ultraviolet LED chip as a light source has been developed for improving the hue. Furthermore, in order to use an LED for lighting applications, etc., it is required to improve its durability.
- an epoxy resin is often used as a sealing material used when sealing a light emitting element such as an LED (light emitting diode) chip.
- Epoxy resins are used because of their transparency and good processability.
- most epoxy resins for sealing LEDs are composed of bisphenol A glycidyl ether and methylhexahydrophthalic anhydride, an amine-based or phosphorus-based curing accelerator.
- these components generate carbonyl groups by absorption of ultraviolet light, they have the disadvantage of absorbing visible light and turning yellow.
- a method using a hydrogenated bisphenol A glycidyl ether Non-Patent Document 1 has been proposed, but the performance is not sufficient.
- Silicone resins are widely used to improve yellowing due to ultraviolet light and brightness reduction. Silicone resin is excellent in transparency in the ultraviolet region, and yellowing due to ultraviolet light and a decrease in transmittance are extremely small. However, the silicone resin has a problem that the light extraction efficiency is low because the refractive index is low, and the adhesion with the lead frame and the reflector is poor because the polarity is low. Further, in a surface mount type LED, soldering by a reflow soldering method is performed. In the reflow furnace, since it is exposed to heat at 260 ° C. for about 10 seconds, the conventional epoxy resin or silicone resin may be deformed or cracked by heat.
- Patent Document 1 discloses that a polymer excellent in optical properties, heat resistance and water resistance can be obtained by homopolymerizing or copolymerizing an alicyclic acrylic acid ester or methacrylic acid ester having 10 or more carbon atoms. It is disclosed. As a use of this polymer, a sealing material for a light emitting diode is described, but an improvement in adhesion and the like is further required. Patent Document 2 describes a transparent sealing material for optical semiconductors that provides a cured product that is stable against ultraviolet rays and heat, hardly causes yellowing, and has excellent adhesion. However, this cured product may be inferior in adhesion to the surrounding base material (reflecting material resin or metal frame), and further technical development has been demanded.
- the present invention has been made in view of the above circumstances, and is a composition suitably used as a raw material for a sealing material, a lens, and the like, and while maintaining the conventional level of transparency and heat resistance, It aims at providing the composition which gives the hardened
- the present invention has been completed based on such findings. That is, the present invention 1.
- the component (A) is a long-chain alkyl (meth) acrylate selected from (meth) acrylates having an alkyl group having 12 or more carbon atoms, and / or the polyalkylene glycol (meth) acrylate having a number average molecular weight of 400 or more.
- the component (A) is a long-chain alkyl (meth) acrylate selected from hydrogenated polybutadiene di (meth) acrylate and hydrogenated polyisoprene di (meth) acrylate, and / or polyethylene glycol di (meta) having a number average molecular weight of 400 or more.
- the component (B) is a (meth) acrylate compound in which one or more alicyclic hydrocarbon groups selected from an adamantyl group, norbornyl group, isobornyl group, dicyclopentanyl group and cyclohexyl group are ester-bonded. 3.
- the polar component (C) is selected from a hydroxyl group, an epoxy group, a glycidyl ether group, a tetrahydrofurfuryl group, an isocyanate group, a carboxyl group, an alkoxysilyl group, a phosphate ester group, a lactone group, an oxetane group and a tetrahydropyranyl group.
- composition according to any one of 1 to 4 which is a (meth) acrylate compound having a group, 6). Based on the sum of component (A), component (B) and component (C), component (A) is 10 to 90% by mass, component (B) is 5 to 90% by mass, component (C) is 0.5 1 to 5 in which the amount of the component (D) is 0.01 to 10 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (C).
- a lens using the cured product as described in 7 above, and The lens according to 10 is a lens for a semiconductor field or an optical field.
- the present invention is a composition that is suitably used as a raw material for a sealing material, a lens, and the like, and has excellent transparency and heat resistance, and adhesion to a substrate around a reflector resin, a metal frame, or the like.
- cured material which is excellent in is provided.
- composition of the present invention comprises (A) (meth) acrylate-modified silicone oil, long-chain alkyl (meth) acrylate, and one or more (meth) acrylate compounds selected from polyalkylene glycol (meth) acrylates having a number average molecular weight of 400 or more. , (B) (meth) acrylate compound in which an alicyclic hydrocarbon group having 6 or more carbon atoms is ester-bonded, (C) (meth) acrylic acid or (meth) acrylate compound having a polar group, and (D) initiation of radical polymerization It contains an agent.
- Component (meth) acrylate-modified silicone oil is a compound having an acryl group and / or a methacryl group at the end and containing a dialkylpolysiloxane in the skeleton.
- the (meth) acrylate-modified silicone oil of component (A) is a modified product of dimethylpolysiloxane in many cases, but the alkyl in the dialkylpolysiloxane skeleton is replaced with a methyl group or an alkyl group other than a methyl group. All or some of the groups may be substituted. Examples of the alkyl group other than the methyl group include an ethyl group and a propyl group.
- polydialkylsiloxane having an acryloxyalkyl terminal or a methacryloxyalkyl terminal can be used.
- (3-acryloxy-2-hydroxypropyl) -terminated polydimethylsiloxane and acryloxy-terminated ethylene oxide dimethylsiloxane-ethylene oxide ABA block copolymer are preferably used because of transparency after curing.
- the long chain alkyl (meth) acrylate as the component (A) is a (meth) acrylate containing a long chain alkyl group.
- the long-chain alkyl group include alkyl groups having 12 or more carbon atoms. Specifically, for example, dodecyl group, lauryl group, tetradecyl group, hexadecyl group, octadecyl group (including stearyl group), eicosyl group, triacontyl Group, tetracontyl group and the like.
- the alkyl group having 12 or more carbon atoms may be an alkyl group derived from a hydride of a polymer such as polybutadiene or polyisoprene. Excellent adhesion can be obtained by using a (meth) acrylate containing an alkyl group having 12 or more carbon atoms.
- Specific examples of the long-chain alkyl (meth) acrylate include hydrogenated polybutadiene such as hydrogenated polybutadiene di (meth) acrylate and hydrogenated polyisoprene (meth) acrylate, and acrylic or methacrylic compounds having a hydrogenated polyisoprene skeleton, or Examples include stearyl methacrylate. Among these, hydrogenated polybutadiene di (meth) acrylate and hydrogenated polyisoprene di (meth) acrylate are preferable in terms of adhesion.
- the polyalkylene glycol (meth) acrylate having a number average molecular weight of 400 or more as the component (A) is polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, ethoxylated trimethylol. Examples thereof include propane tri (meth) acrylate and ethoxylated pentaerythritol tetra (meth) acrylate.
- a polyalkylene glycol (meth) acrylate having a number average molecular weight of 400 or more excellent toughness and adhesion can be obtained.
- the maximum value of the number average molecular weight is not particularly limited, but a number average molecular weight of 10,000 or less is preferable from the viewpoint of compatibility with the component (B).
- the component (A) at least one selected from the (meth) acrylate-modified silicone oils, at least one selected from the long-chain alkyl (meth) acrylates, or the number average molecular weight of 400 or more.
- At least one selected from polyalkylene glycol (meth) acrylates of the above, or (meth) acrylate-modified silicone oil, long-chain alkyl (meth) acrylate and polyalkylene having a number average molecular weight of 400 or more You may select and combine suitably from glycol (meth) acrylate.
- the component (A) is usually 10 to 90% by mass, preferably 15 to 80% by mass, based on the sum of the components (A), (B) and (C).
- the adhesiveness and toughness which were excellent by making (A) component 10 mass% or more are obtained.
- the alicyclic hydrocarbon group of the (meth) acrylate compound in which the alicyclic hydrocarbon group having 6 or more carbon atoms of the component (B) is ester-bonded includes a cyclohexyl group, a 2-decahydronaphthyl group, an adamantyl group, 1- Methyladamantyl group, 2-methyladamantyl group, biadamantyl group, dimethyladamantyl group, norbornyl group, 1-methyl-norbornyl group, 5,6-dimethyl-norbornyl group, isobornyl group, tetracyclo [4.4.12, 5.17,10] dodecyl group, 9-methyl-tetracyclo [4.4.0.12,5.17,10] dodecyl group, bornyl group, dicyclopentanyl group and the like, and from the viewpoint of heat resistance Among them, cyclohexyl group, adamantyl group, norbornyl
- the (meth) acrylate compound as the component (B) the (meth) acrylate having the alicyclic hydrocarbon group, for example, cyclohexyl acrylate, cyclohexyl methacrylate, 1-adamantyl (meth) acrylate, norbornyl (meth) acrylate, Isobonyl (meth) acrylate, dicyclopentanyl (meth) acrylate, etc. are mentioned.
- the component (B) one type of the (meth) acrylate compound may be used, or two or more types may be used in combination.
- excellent heat resistance can be obtained by using an alicyclic hydrocarbon group having 6 or more carbon atoms.
- the ester substituent is an alicyclic hydrocarbon group and does not contain aromatics, it is difficult to cause deterioration due to ultraviolet rays.
- the component (B) is usually 5 to 90% by mass, preferably 10 to 80% by mass, based on the sum of the components (A), (B) and (C). By setting the component (B) to 5% by mass or more, excellent rigidity, heat resistance, and transparency can be obtained.
- component (C) acrylic acid or methacrylic acid or a (meth) acrylate compound having a polar group is used. Since the component (C) has polarity, it forms a hydrogen bond with a metal surface having polarity in the same manner, thereby improving adhesion. Further, the wettability is improved by the presence of the polar group.
- an alkylene glycol group may be concerned with adhesion
- (meth) acrylate compounds having polar groups include (meth) acrylate compounds in which substituents containing atoms other than carbon and hydrogen are ester-bonded.
- substituents include hydroxyl groups, epoxy groups, glycidyl ether groups, tetrahydro groups.
- substituents include a furfuryl group, an isocyanate group, a carboxyl group, an alkoxysilyl group, a phosphate ester group, a lactone group, an oxetane group, a tetrahydropyranyl group, and an amino group.
- At least one selected from the (meth) acrylic acid or at least one selected from the (meth) acrylate compounds having the polar group may be used. Or you may select and combine suitably from the said (meth) acrylic acid and the (meth) acrylate compound which has a polar group.
- the component (C) is usually 0.5 to 50% by mass, preferably 1 to 40% by mass, based on the sum of the components (A), (B) and (C). .
- the component (C) is 0.5% by mass or more, excellent adhesion to a resin material or a metal material that comes into contact with the encapsulant when the optical semiconductor is encapsulated is exhibited.
- Component radical polymerization initiators include ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, 1,1,3,3-tetra Hydroperoxides such as methylbutyl hydroperoxide, cumene hydroperoxide, t-butyl hydroperoxide, diisobutyryl peroxide, bis-3,5,5-trimethylhexanol peroxide, lauroyl peroxide, benzoyl peroxide, Diacyl peroxides such as m-toluylbenzoyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butyl) Ruoxy) hexane, 1,3-bis (t-butylperoxyisopropyl) hexane,
- Irgacure 651 (Irgacure 651, Ciba Specialty Chemicals, Trademark), Irgacure 184 (Irgacure 184, Ciba Specialty Chemicals, Trademark), Darocur 1173 (DAROCUR1173, Ciba Specialty Chemicals, Trademark)
- Irgacure 2959 (Irgacure 2959, Ciba Specialty Chemicals, Trademark)
- Irgacure 127 (Irgacure 127, Ciba Specialty Chemicals, Trademark)
- Irgacure 907 (Irgacure 907, Ciba Specialty Chemicals, Trademark)
- Irgacure 36ur Ciba Specialty Chemicals, Inc.
- Irgacure 379 (Ir acure 379, Ciba Specialty Chemicals, Inc., Darocur TPO (
- the radical polymerization initiator of component (D) may be used alone, or a plurality of radical polymerization initiators may be used in combination.
- the amount of use is usually 0.01 to 10 parts by mass, preferably 0.1 to 5.0 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (C). is there.
- the composition of the present invention may contain inorganic particles and phosphors as the component (E) in addition to the components (A) to (D).
- inorganic particles can be used, and specific examples thereof include silica particles such as quartz, silicic anhydride, fused silica and crystalline silica, alumina, zirconia and titanium oxide.
- inorganic particles that are used or proposed as fillers for conventional sealing materials such as epoxy resins can be used.
- the inorganic particles may be appropriately subjected to surface treatment, and examples thereof include alkylation treatment, trimethylsilylation treatment, silicone treatment, and treatment with a coupling agent.
- YAG fluorescent substance, silicate fluorescent substance, etc. can be used as fluorescent substance for white LED.
- the inorganic particles and phosphors of component (E) may be used alone, or a plurality of compounds may be used in combination.
- the amount used is usually 1 to 100 parts by mass, preferably 10 to 50 parts by mass, with respect to 100 parts by mass in total of the components (A), (B) and (C).
- composition of the present invention one or more other (meth) acrylate compounds [(meth) acrylate compounds other than the components (A) to (C)] are added as the component (F) for imparting strength.
- Component (meth) acrylate compounds include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol (meth) acrylate, 1,6-hexanediol di (meth) Acrylate, 1,9-nonanediol di (meth) acrylate, neopentyldiol di (meth) acrylate, polyethylene glycol di (meth) acrylate having a number average molecular weight of less than 400, polypropylene glycol di (meth) acrylate, methoxypolyethylene methacrylate, etc.
- Component (meth) acrylate compound may be used alone, or a plurality of compounds may be used in combination.
- the content is usually 100 parts by mass or less, preferably 50 parts by mass or less, with respect to 100 parts by mass in total of the component (A), the component (B) and the component (C).
- antioxidants examples include phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, vitamin antioxidants, lactone antioxidants, amine antioxidants, and the like.
- phenolic antioxidants examples include Irganox 1010 (Irganox 1010, Ciba Specialty Chemicals, Trademark), Irganox 1076 (Irganox 1076, Ciba Specialty Chemicals, Trademark), Irganox 1330 (Irganox 1330, Ciba Specialty Chemicals, Trademark) ), Irganox 3114 (Irganox 3114, Ciba Specialty Chemicals, Trademark), Irganox 3125 (Irganox 3125, Ciba Specialty Chemicals, Trademark), Irganox 3790 (Irganox 3790, Ciba Specialty Chemicals, Trademark) B90, Cyanox (Cyanox 1790, trade name, Cyanamid Co., Ltd.), Sumilizer GA-80 SumilizerGA-80, Sumitomo Chemical Co., trademark) can be exemplified commercially available products such as.
- Examples of phosphorus antioxidants include Irgafos 168 (Irgafos 168, Ciba Specialty Chemicals, Inc.), Irgafos 12 (Irgafos 12, Ciba Specialty Chemicals, Inc.), Irgafos 38 (Irgafos 38, Ciba Specialty Chemicals, Inc.) Trademark), ADK STAB 329K (ADKSTAB 329K, ADEKA, trademark), ADK STAB PEP36 (ADKSTAB PEP36, ADEKA, trademark), ADK STAB PEP-8 (ADKSTAB PEP-8, ADEKA, trademark), Sardstab P-EPQ (Clariant) Trademark), Weston 618 (Weston 618, GE, trademark), Weston 619G (Weston 619G, GE, trademark), Weston 624 (Weston-624, GE Corporation, trademark) can be mentioned a commercially available product, such as.
- sulfur-based antioxidant examples include DSTP (Yoshitomi, Trademark), DLTP (Yoshitomi, Trademark), DLTOIB (Yoshitomi, Trademark), DMTP (Yoshitomi, Trademark), Examples include commercially available products such as Seenox 412S (Cypro Kasei Co., Ltd., Trademark), Cyanox 1212 (Cyanamide Corp., Trademark), and Sumilizer TP-D (Sumilizer TP-D, Sumitomo Chemical Co., Ltd.).
- vitamin antioxidants examples include tocopherol, Irganox E201 (Irganox E201, Ciba Specialty Chemicals, trademark, compound name; 2,5,7,8-tetramethyl-2 (4 ′, 8 ′, 12′-trimethyl) There are commercial products such as tridecyl) coumarone-6-ol).
- lactone antioxidant those described in JP-A-7-233160 and JP-A-7-247278 can be used.
- HP-136 Ciba Specialty Chemicals, trademark, compound name; 5,7-di-t-butyl-3- (3,4-dimethylphenyl) -3H-benzofuran-2-one
- amine-based antioxidants examples include commercially available products such as Irgastab FS042 (Ciba Specialty Chemicals, Trademark) and GENOX EP (Crimpton, Trademark, Compound Name: Dialkyl-N-methylamine oxide).
- antioxidants may be used alone or in combination with a plurality of compounds.
- the content is usually 0.005 to 5 parts by mass, preferably 0.02 to 2 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (C).
- ADK STAB LA-52, LA-57, LA-62, LA-63, LA-67, LA-68, LA-77, LA-82, LA-87 manufactured by ADEKA are available as trade names.
- These light stabilizers may be used alone or in combination with a plurality of compounds.
- the content thereof is usually 0.005 to 5 parts by mass, preferably 0.002 to 2 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (C).
- the composition of the present invention gives a cured product by heat treatment at a temperature higher than the temperature at which radicals are generated from the component (D) (in the case of a radical photopolymerization initiator, by irradiation with light).
- the curing conditions may be appropriately adopted in consideration of the decomposition characteristics of the initiator.
- a cured product obtained by curing the composition of the present invention is preferably used as a sealing material or a lens material. Examples of the sealing material include a sealing material for optical semiconductors and a sealing material for light receiving elements.
- Examples of elements to be sealed include light emitting diode (LED) chips, semiconductor lasers, photodiodes, photointerrupters, photocouplers, A phototransistor, an electroluminescence element, a CCD, a solar cell, and the like can be given.
- Examples of the lens include a lens for a semiconductor field and a lens for an optical field.
- Two sheets of polyphthalamide resin (Amodel A-4122NL, Solvay Advanced Polymer Co., Ltd.) (25 mm in width, 100 mm in length, 2 mm in thickness) were stacked by 1.25 cm and obtained in the examples or comparative examples on the overlapping portions.
- a test piece coated with the composition and cured, and two silver-plated metal plates (width 10 mm, length 75 mm, thickness 0.15 mm) are stacked 2 cm, and the composition is applied to the overlapping portion and cured.
- a tensile tester Autograph AG-10 with a thermostatic bath manufactured by Shimadzu Corporation was used. Measurement temperature 23 ° C., humidity 50%, tensile speed 20 mm / min, tensile load load cell 10 kN.
- Example 1 As component (A) [long chain alkyl (meth) acrylate], hydrogenated polybutadiene diacrylate (trade name SPBDA-S30 manufactured by Osaka Organic Chemical Industry Co., Ltd., 5 g), as component (B), 1-adamantyl methacrylate (Idemitsu Kosan) Product name: adamantate M-104) 5 g, (C) component, 2-hydroxyethyl methacrylate (Tokyo Chemical Industry Co., Ltd.) 0.5 g, (D) component 1,1-bis ( t-Hexylperoxy) cyclohexane (manufactured by NOF Corporation, trade name: Perhexa HC) 0.1 g was used, and these were mixed to obtain a composition.
- component (A) [long chain alkyl (meth) acrylate], hydrogenated polybutadiene diacrylate (trade name SPBDA-S30 manufactured by Osaka Organic Chemical Industry Co., Ltd., 5 g), as component (B
- This composition was poured into a cell formed by sandwiching a Teflon (registered trademark) spacer having a thickness of 3 mm between two steel plates and an aluminum plate having a thickness of 0.3 mm between the steel plate and the spacers, and then in an oven at 110 ° C. After heating at 160 ° C. for 1 hour, and then cooling to room temperature, a colorless and transparent plate-like cured product having a thickness of 3 mm was obtained. Moreover, the test piece for an adhesive test was obtained by making it harden
- Example 2 As the component (C), a composition and a cured product were obtained in the same manner as in Example 1 except that methacrylic acid (manufactured by Wako Pure Chemical Industries, Ltd.) was used. Table 1 shows the evaluation results of the obtained cured product.
- Example 3 As the component (C), a composition and a cured product were obtained in the same manner as in Example 1 except that glycidyl methacrylate (manufactured by Wako Pure Chemical Industries, Ltd.) was used. Table 1 shows the evaluation results of the obtained cured product.
- Example 4 A composition and a cured product were obtained in the same manner as in Example 1 except that 2-isocyanatoethyl methacrylate (trade name: Karenz MOI, manufactured by Showa Denko KK) was used as the component (C). Table 1 shows the evaluation results of the obtained cured product.
- 2-isocyanatoethyl methacrylate trade name: Karenz MOI, manufactured by Showa Denko KK
- Example 5 A composition and a cured product were obtained in the same manner as in Example 1 except that 3-methacryloxypropyltrimethoxysilane (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as the component (C). Table 1 shows the evaluation results of the obtained cured product.
- 3-methacryloxypropyltrimethoxysilane trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.
- Example 6 As a component (C), a composition and a cured product were obtained in the same manner as in Example 1 except that tetrahydrofurfuryl methacrylate (trade name: SR203 manufactured by Sartomer) was used. Table 1 shows the evaluation results of the obtained cured product.
- Example 7 As the component (C), a composition and a cured product were obtained in the same manner as in Example 1 except that 0.1 g of KAYAMER PM-21 (trade name) of Nippon Kayaku Co., Ltd., which is a methacrylate having a phosphate ester structure, was used. Obtained. Table 1 shows the evaluation results of the obtained cured product.
- Example 8 A composition and a cured product were obtained in the same manner as in Example 3 except that hydrogenated polyisoprene acrylate (manufactured by Osaka Organic Chemical Industry, trade name SPIDA) was used as the component (A). Table 1 shows the evaluation results of the obtained cured product.
- hydrogenated polyisoprene acrylate manufactured by Osaka Organic Chemical Industry, trade name SPIDA
- Example 9 A composition and a cured product were obtained in the same manner as in Example 5 except that hydrogenated polyisoprene diacrylate (trade name SPIDA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) was used as the component (A). Table 1 shows the evaluation results of the obtained cured product.
- hydrogenated polyisoprene diacrylate trade name SPIDA, manufactured by Osaka Organic Chemical Industry Co., Ltd.
- Comparative Example 1 A composition and a cured product were obtained in the same manner as in Example 1 except that the component (C) was not used. Table 1 shows the evaluation results of the obtained cured product.
- Example 10 Component [polyalkylene glycol (meth) acrylate having a number average molecular weight of 400 or more], polyethylene glycol # 400 dimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name: NK ester 9G), 5 g, (B) component , 1-adamantyl methacrylate (made by Idemitsu Kosan Co., Ltd., trade name: adamantate M-104) 5 g, (C) component as 2-hydroxyethyl methacrylate (Tokyo Chemical Industry Co., Ltd.) 0.5 g As a component, 0.1 g of 1,1-bis (t-hexylperoxy) cyclohexane (manufactured by NOF Corporation, trade name: Perhexa HC) was used, and these were mixed to obtain a composition.
- a component 0.1 g of 1,1-bis (t-hexylperoxy) cyclohexane (man
- This composition was poured into a cell prepared by sandwiching a Teflon (registered trademark) spacer having a thickness of 3 mm between two steel plates and an aluminum plate having a thickness of 0.3 mm between the steel plate and the spacers, and then in an oven at 110 ° C. After heating at 160 ° C. for 1 hour, and then cooling to room temperature, a colorless and transparent plate-like cured product having a thickness of 3 mm was obtained. Moreover, the test piece for an adhesive test was obtained by making it harden
- Example 11 (C) As a component, the composition and hardened
- Example 12 A composition and a cured product were obtained in the same manner as in Example 10 except that glycidyl methacrylate (manufactured by Wako Pure Chemical Industries, Ltd.) was used as the component (C). The evaluation results of the obtained cured product are shown in Table 2.
- Example 13 A composition and a cured product were obtained in the same manner as in Example 10 except that 2-isocyanatoethyl methacrylate (trade name: Karenz MOI, manufactured by Showa Denko KK) was used as the component (C). The evaluation results of the obtained cured product are shown in Table 2.
- 2-isocyanatoethyl methacrylate trade name: Karenz MOI, manufactured by Showa Denko KK
- Example 14 A composition and a cured product were obtained in the same manner as in Example 10 except that 3-methacryloxypropyltrimethoxysilane (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.) was used as the component (C). The evaluation results of the obtained cured product are shown in Table 2.
- Example 15 As the component (C), a composition and a cured product were obtained in the same manner as in Example 10 except that tetrahydrofurfuryl methacrylate (trade name: SR203 manufactured by Sartomer) was used. The evaluation results of the obtained cured product are shown in Table 2.
- Example 16 A composition and a cured product were obtained in the same manner as in Example 10 except that 0.1 g of KAYAMER PM-21 (trade name) of Nippon Kayaku Co., Ltd., which is a methacrylate having a phosphate ester structure, was used as the component (C). Obtained. The evaluation results of the obtained cured product are shown in Table 2.
- Comparative Example 2 A composition and a cured product were obtained in the same manner as in Example 10 except that the component (C) was not used. The evaluation results of the obtained cured product are shown in Table 2.
- composition that provides a cured product that is excellent in transparency and heat resistance and has excellent adhesion to a surrounding substrate such as a reflector resin or a metal frame.
- the composition of the present invention is suitably used as a raw material for sealing materials such as light emitting elements and light receiving elements in optical semiconductor devices, and lenses used in the semiconductor field and optical field.
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Abstract
Description
この光半導体装置の例としては、例えば、GaN、GaAlN、InGaNおよびInAlGaN等の窒化ガリウム系化合物半導体を用いた可視光発光デバイスや高温動作電子デバイスがあり、最近では、青色発光ダイオード、紫外発光ダイオードの分野で開発が進んでいる。
LEDチップを発光素子として備える光半導体装置は、リードフレームの発光面側にLEDチップを搭載して、LEDチップとリードフレームとをワイヤボンディングにより電気的に接続して、さらに、発光素子の保護およびレンズ機能を兼ねた樹脂により封止されている。
また、表面実装タイプのLEDにおいては、リフローはんだ方式によるはんだ付けが行われる。リフロー炉内では、260℃の熱に約10秒間曝されるため、従来のエポキシ樹脂やシリコーン樹脂では熱による変形、割れが発生することがある。
特許文献2には、紫外線や熱に対して安定で黄変が発生しにくく、かつ、密着性にも優れた硬化物を与える光半導体用の透明封止材料等が記載されている。しかしながら、この硬化物は周りの基材(反射材樹脂や金属フレーム)との密着性に劣る場合があり、さらなる技術開発が求められていた。
すなわち本発明は、
1.(A)(メタ)アクリレート変性シリコーンオイル、長鎖アルキル(メタ)アクリレートおよび数平均分子量400以上のポリアルキレングリコール(メタ)アクリレートから選ばれる一種以上の(メタ)アクリレート化合物、(B)炭素数6以上の脂環式炭化水素基がエステル結合した(メタ)アクリレート化合物、(C)(メタ)アクリル酸又は極性基を有する(メタ)アクリレート化合物並びに(D)ラジカル重合開始剤を含むことを特徴とする組成物、
2.前記(A)成分が炭素数12以上のアルキル基を有する(メタ)アクリレートから選ばれる長鎖アルキル(メタ)アクリレート、および/又は前記数平均分子量400以上のポリアルキレングリコール(メタ)アクリレートである前記1に記載の組成物、
3.前記(A)成分が、水素化ポリブタジエンジ(メタ)アクリレートおよび水素化ポリイソプレンジ(メタ)アクリレートから選ばれる長鎖アルキル(メタ)アクリレート、および/又は数平均分子量400以上のポリエチレングリコールジ(メタ)アクリレートである前記1または2に記載の組成物、
4.前記(B)成分が、アダマンチル基、ノルボルニル基、イソボニル基、ジシクロペンタニル基およびシクロヘキシル基から選ばれる一種以上の脂環式炭化水素基がエステル結合した(メタ)アクリレート化合物である前記1~3のいずれかに記載の組成物、
5.前記(C)成分が、水酸基、エポキシ基、グリシジルエーテル基、テトラヒドロフルフリル基、イソシアネート基、カルボキシル基、アルコキシシリル基、リン酸エステル基、ラクトン基、オキセタン基およびテトラヒドロピラニル基から選ばれる極性基を有する(メタ)アクリレート化合物である前記1~4のいずれかに記載の組成物、
6.(A)成分、(B)成分および(C)成分の合計を基準として、(A)成分が10~90質量%、(B)成分が5~90質量%、(C)成分が0.5~50質量%であり、(A)成分、(B)成分および(C)成分の合計100質量部に対して、(D)成分の量が0.01~10質量部である前記1~5のいずれかに記載の組成物、
7.前記1~6のいずれかに記載の組成物を硬化して得られる硬化物、
8.前記7に記載の硬化物を用いた封止材、
9.光半導体用または受光素子用の封止材である前記8に記載の封止材、
10.前記7に記載の硬化物を用いたレンズ、および
11.半導体分野用または光学分野用のレンズである前記10に記載のレンズ
を提供するものである。
これらの中では、硬化後の透明性から、(3-アクリロキシ-2-ヒドロキシプロピル)末端ポリジメチルシロキサンおよびアクリロキシ末端エチレンオキシドジメチルシロキサン-エチレンオキシドABAブロック共重合体が好適に用いられる。
長鎖アルキル(メタ)アクリレートの具体例としては、水素化ポリブタジエンジ(メタ)アクリレート、水素化ポリイソプレンジ(メタ)アクリレート等の水素化ポリブタジエンや水素化ポリイソプレン骨格を有するアクリルまたはメタクリル化合物、あるいはステアリルメタクリレート等が挙げられる。
これらの中では、密着性の点で、水素化ポリブタジエンジ(メタ)アクリレート、水素化ポリイソプレンジ(メタ)アクリレートが好ましい。
本発明においては脂環式炭化水素基の炭素数が6以上のものを用いることにより優れた耐熱性が得られる。また、エステル置換基が脂環式炭化水素基であり、芳香族等を含有しないので紫外線による劣化を引き起こしにくい。
本発明においては、(C)成分として、前記(メタ)アクリル酸の中から選ばれる少なくとも一種、又は前記極性基を有する(メタ)アクリレート化合物の中から選ばれる少なくとも一種を用いても良いし、或いは、前記の(メタ)アクリル酸および極性基を有する(メタ)アクリレート化合物の中から適当に選び組み合わせてもよい。
また、白色LED用の蛍光体として、YAG蛍光体、シリケート蛍光体等を使用できる。
(E)成分の無機粒子や蛍光体は、単独で使用してもよく、また、複数の化合物を併用してもよい。その使用量は、(A)成分、(B)成分および(C)成分の合計100質量部に対して、通常、1~100質量部、好ましくは10~50質量部である。
イオウ系酸化防止剤としては、例えばDSTP(ヨシトミ)(吉富社、商標)、DLTP(ヨシトミ)(吉富社、商標)、DLTOIB(吉富社、商標)、DMTP(ヨシトミ)(吉富社、商標)、Seenox 412S(シプロ化成社、商標)、Cyanox 1212(サイアナミド社、商標)、スミライザーTP-D(SumilizerTP-D、住友化学社、商標)などの市販品を挙げることができる。
ラクトン系酸化防止剤としては、特開平7-233160号公報、特開平7-247278号公報に記載されているものを使用できる。また、HP-136(チバ・スペシャリティ・ケミカルズ社、商標、化合物名;5,7-ジ-t-ブチル-3-(3,4-ジメチルフェニル)-3H-ベンゾフラン-2-オン)などがある。
アミン系酸化防止剤としては、イルガスタブFS042(チバ・スペシャリティ・ケミカルズ社、商標)、GENOX EP(クロンプトン社、商標、化合物名;ジアルキル-N-メチルアミンオキサイド)などの市販品を挙げることができる。
本発明の組成物を硬化して得られる硬化物は封止材やレンズの材料として好ましく用いられる。
封止材としては光半導体用封止材や受光素子用封止材が挙げられ、封止される素子としては、例えば発光ダイオード(LED)チップ、半導体レーザー、フォトダイオード、フォトインタラプタ、フォトカプラ、フォトトランジスタ、エレクトロルミネッセンス素子、CCD、太陽電池等が挙げられる。
レンズとしては、半導体分野用レンズや光学分野用のレンズが挙げられる。
なお、各実施例および比較例において得られた硬化物の物性評価方法は以下の通りである。また数平均分子量はNMRにより測定した。
試料として厚み3mmの試験片を用いてJIS K7105に準拠して測定した。測定装置はHGM-2DP(スガ試験機株式会社)を用いた。140℃の恒温槽に試験片を100時間置き、その前後の全光線透過率を測定した。
(2)密着性試験
光半導体の封止を想定して密着性試験を行った。すなわち封止樹脂と接触する反射材樹脂(ポリアミド樹脂)およびリードフレームの金属に対する密着性を以下のように評価した。
ポリフタルアミド樹脂(アモデル A-4122NL、ソルベイアドバンスドポリマー株式会社)の板(幅25mm、長さ100mm、厚み2mm)2枚を1.25cm重ねて、重なる部分に実施例または比較例で得られた組成物を塗布して硬化させた試験片、および銀メッキした金属板(幅10mm、長さ75mm、厚み0.15mm)2枚を2cm重ねて、重なる部分に前記組成物を塗布して硬化させた試験片を用いてJIS K6850に準拠して測定した。測定装置は、(株)島津製作所製恒温槽付引張試験機オートグラフAG-10を用いた。測定温度23℃、湿度50%、引張り速度20mm/分、引張り荷重 ロードセル 10kN。
(A)成分〔長鎖アルキル(メタ)アクリレート〕として、水素化ポリブタジエンジアクリレート(大阪有機化学工業株式会社製、商品名SPBDA-S30)5g、(B)成分として、1-アダマンチルメタクリレート(出光興産株式会社製、商品名:アダマンテートM-104)5g、(C)成分として、2-ヒドロキシエチルメタクリレート(東京化成工業株式会社製)0.5g、(D)成分として、1,1-ビス(t-ヘキシルペルオキシ)シクロヘキサン(日本油脂株式会社製、商品名:パーヘキサHC)0.1gを使用し、これらを混合して組成物を得た。
この組成物を、2枚の鋼板に3mm厚みのテフロン(登録商標)製スペーサと鋼板とスペーサの間に厚み0.3mmのアルミ板を挟みこんで作成したセルに流し込み、オーブンにて、110℃で3時間、次いで160℃で1時間加熱を行った後、室温に冷却することで、無色透明な厚み3mmの板状硬化物を得た。また、同じ条件にて硬化させることにより、密着性試験用の試験片を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、メタクリル酸(和光純薬工業製)を用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、グリシジルメタクリレート(和光純薬工業製)を用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、2-イソシアナトエチルメタクリレート(昭和電工株式会社製 商品名:カレンズMOI)を用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業製 商品名:KBM-503)を用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、テトラヒドロフルフリルメタクリレート(サートマー製 商品名:SR203)を用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分として、リン酸エステル構造を持つメタクリレートである日本化薬株式会社のKAYAMER PM-21(商品名)を0.1g用いた以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(A)成分として、水素化ポリイソプレンジアクリレート(大阪有機化学工業社製、商品名SPIDA)を用いた以外は実施例3と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(A)成分として、水素化ポリイソプレンジアクリレート(大阪有機化学工業社製、商品名SPIDA)を用いた以外は実施例5と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(C)成分を用いなかった以外は実施例1と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第1表に示す。
(A)成分〔数平均分子量400以上のポリアルキレングリコール(メタ)アクリレート〕として、ポリエチレングリコール#400ジメタクリレート(新中村化学工業株式会社製、商品名:NKエステル 9G)5g、(B)成分として、1-アダマンチルメタクリレート(出光興産株式会社製、商品名:アダマンテートM-104)5g、(C)成分として、2-ヒドロキシエチルメタクリレート(東京化成工業株式会社製)0.5gに、(D)成分として、1,1-ビス(t-ヘキシルペルオキシ)シクロヘキサン(日本油脂株式会社製、商品名:パーヘキサHC)0.1gを使用し、これらを混合して組成物を得た。
この組成物を、2枚の鋼板に3mm厚みのテフロン(登録商標)製スペーサと鋼板とスペーサの間に厚み0.3mmのアルミ板を挟みこんで作成したセルに流し込み、オーブンにて、110℃で3時間、次いで160℃で1時間加熱を行った後、室温に冷却することで、無色透明な厚み3mmの板状硬化物を得た。また、同じ条件で硬化させることにより、密着性試験用の試験片を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、メタクリル酸(和光純薬工業製)を用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、グリシジルメタクリレート(和光純薬工業製)を用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、2-イソシアナトエチルメタクリレート(昭和電工株式会社製 商品名:カレンズMOI)を用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業製 商品名:KBM-503)を用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、テトラヒドロフルフリルメタクリレート(サートマー製 商品名:SR203)を用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分として、リン酸エステル構造を持つメタクリレートである日本化薬株式会社のKAYAMER PM-21(商品名)を0.1g用いた以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
(C)成分を用いなかった以外は実施例10と同様にして組成物および硬化物を得た。得られた硬化物の評価結果を第2表に示す。
Claims (11)
- (A)(メタ)アクリレート変性シリコーンオイル、長鎖アルキル(メタ)アクリレートおよび数平均分子量400以上のポリアルキレングリコール(メタ)アクリレートから選ばれる一種以上の(メタ)アクリレート化合物、(B)炭素数6以上の脂環式炭化水素基がエステル結合した(メタ)アクリレート化合物、(C)(メタ)アクリル酸又は極性基を有する(メタ)アクリレート化合物並びに(D)ラジカル重合開始剤を含むことを特徴とする組成物。
- 前記(A)成分が炭素数12以上のアルキル基を有する(メタ)アクリレートから選ばれる長鎖アルキル(メタ)アクリレート、および/又は前記数平均分子量400以上のポリアルキレングリコール(メタ)アクリレートである請求項1に記載の組成物。
- 前記(A)成分が、水素化ポリブタジエンジ(メタ)アクリレートおよび水素化ポリイソプレンジ(メタ)アクリレートから選ばれる長鎖アルキル(メタ)アクリレート、および/又は数平均分子量400以上のポリエチレングリコールジ(メタ)アクリレートである請求項1または2に記載の組成物。
- 前記(B)成分が、アダマンチル基、ノルボルニル基、イソボニル基、ジシクロペンタニル基およびシクロヘキシル基から選ばれる一種以上の脂環式炭化水素基がエステル結合した(メタ)アクリレート化合物である請求項1~3のいずれかに記載の組成物。
- 前記(C)成分が、水酸基、エポキシ基、グリシジルエーテル基、テトラヒドロフルフリル基、イソシアネート基、カルボキシル基、アルコキシシリル基、リン酸エステル基、ラクトン基、オキセタン基およびテトラヒドロピラニル基から選ばれる極性基を有する(メタ)アクリレート化合物である請求項1~4のいずれかに記載の組成物。
- (A)成分、(B)成分および(C)成分の合計を基準として、(A)成分が10~90質量%、(B)成分が5~90質量%、(C)成分が0.5~50質量%であり、(A)成分、(B)成分および(C)成分の合計100質量部に対して、(D)成分の量が0.01~10質量部である請求項1~5のいずれかに記載の組成物。
- 請求項1~6のいずれかに記載の組成物を硬化して得られる硬化物。
- 請求項7に記載の硬化物を用いた封止材。
- 光半導体用または受光素子用の封止材である請求項8に記載の封止材。
- 請求項7に記載の硬化物を用いたレンズ。
- 半導体分野用または光学分野用のレンズである請求項10に記載のレンズ。
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KR1020127002986A KR101728925B1 (ko) | 2009-08-04 | 2010-07-26 | 아크릴레이트계 조성물 |
US13/388,545 US20120142867A1 (en) | 2009-08-04 | 2010-07-26 | Acrylate composition |
JP2011525854A JP5798033B2 (ja) | 2009-08-04 | 2010-07-26 | アクリレート系組成物 |
CN201080035277.8A CN102471416B (zh) | 2009-08-04 | 2010-07-26 | 丙烯酸酯类组合物 |
EP10806355.3A EP2463316B1 (en) | 2009-08-04 | 2010-07-26 | Acrylate composition |
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EP (1) | EP2463316B1 (ja) |
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KR (1) | KR101728925B1 (ja) |
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WO2013027640A1 (ja) * | 2011-08-19 | 2013-02-28 | 出光興産株式会社 | アクリレート系組成物 |
JP2013049757A (ja) * | 2011-08-30 | 2013-03-14 | Fujifilm Corp | 硬化性組成物およびこれを用いたled素子 |
JP2014189758A (ja) * | 2013-03-28 | 2014-10-06 | Nippon Shokubai Co Ltd | 不飽和カルボニル変性共役ジエン系ポリマーを用いたエネルギー線硬化型樹脂組成物 |
US20150086777A1 (en) * | 2012-03-16 | 2015-03-26 | Toray Industries, Inc. | Laminated film and method for producing same |
JP2015071726A (ja) * | 2013-10-04 | 2015-04-16 | スリーボンドファインケミカル株式会社 | 光硬化性封止剤組成物 |
KR101758570B1 (ko) * | 2012-03-06 | 2017-07-14 | 삼성에스디아이 주식회사 | 광경화 조성물, 이를 포함하는 장벽층 및 이를 포함하는 봉지화된 장치 |
JP2019515076A (ja) * | 2016-05-11 | 2019-06-06 | モメンティブ・パフォーマンス・マテリアルズ・コリア・カンパニー・リミテッドMomentive Performance Materials Korea Co.,Ltd | 有機電子素子封止材用組成物およびこれを用いて形成された封止材 |
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JP5775525B2 (ja) * | 2010-10-25 | 2015-09-09 | 出光興産株式会社 | (メタ)アクリレート系組成物 |
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WO2013027640A1 (ja) * | 2011-08-19 | 2013-02-28 | 出光興産株式会社 | アクリレート系組成物 |
CN103732640A (zh) * | 2011-08-19 | 2014-04-16 | 出光兴产株式会社 | 丙烯酸酯系组合物 |
JP2013049757A (ja) * | 2011-08-30 | 2013-03-14 | Fujifilm Corp | 硬化性組成物およびこれを用いたled素子 |
KR101758570B1 (ko) * | 2012-03-06 | 2017-07-14 | 삼성에스디아이 주식회사 | 광경화 조성물, 이를 포함하는 장벽층 및 이를 포함하는 봉지화된 장치 |
US20150086777A1 (en) * | 2012-03-16 | 2015-03-26 | Toray Industries, Inc. | Laminated film and method for producing same |
US9771491B2 (en) * | 2012-03-16 | 2017-09-26 | Toray Industries, Inc. | Laminated film and method for producing same |
JP2014189758A (ja) * | 2013-03-28 | 2014-10-06 | Nippon Shokubai Co Ltd | 不飽和カルボニル変性共役ジエン系ポリマーを用いたエネルギー線硬化型樹脂組成物 |
JP2015071726A (ja) * | 2013-10-04 | 2015-04-16 | スリーボンドファインケミカル株式会社 | 光硬化性封止剤組成物 |
JP2019515076A (ja) * | 2016-05-11 | 2019-06-06 | モメンティブ・パフォーマンス・マテリアルズ・コリア・カンパニー・リミテッドMomentive Performance Materials Korea Co.,Ltd | 有機電子素子封止材用組成物およびこれを用いて形成された封止材 |
Also Published As
Publication number | Publication date |
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EP2463316A4 (en) | 2014-01-22 |
US20120142867A1 (en) | 2012-06-07 |
KR20120052275A (ko) | 2012-05-23 |
EP2463316B1 (en) | 2016-06-08 |
EP2463316A1 (en) | 2012-06-13 |
JPWO2011016356A1 (ja) | 2013-01-10 |
TWI523871B (zh) | 2016-03-01 |
KR101728925B1 (ko) | 2017-04-20 |
TW201122001A (en) | 2011-07-01 |
CN102471416B (zh) | 2014-11-26 |
JP5798033B2 (ja) | 2015-10-21 |
CN102471416A (zh) | 2012-05-23 |
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