JP5075680B2 - 光素子用封止材および光素子封止体 - Google Patents
光素子用封止材および光素子封止体 Download PDFInfo
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- JP5075680B2 JP5075680B2 JP2008051570A JP2008051570A JP5075680B2 JP 5075680 B2 JP5075680 B2 JP 5075680B2 JP 2008051570 A JP2008051570 A JP 2008051570A JP 2008051570 A JP2008051570 A JP 2008051570A JP 5075680 B2 JP5075680 B2 JP 5075680B2
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- 230000003287 optical effect Effects 0.000 title claims description 129
- 239000003566 sealing material Substances 0.000 title claims description 63
- 238000007789 sealing Methods 0.000 title claims description 29
- -1 silane compound Chemical class 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 75
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims description 59
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 51
- 229910000077 silane Inorganic materials 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 31
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 25
- 239000008393 encapsulating agent Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 150000004292 cyclic ethers Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 235000011007 phosphoric acid Nutrition 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000005011 phenolic resin Substances 0.000 description 8
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 150000003016 phosphoric acids Chemical class 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
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- 239000012153 distilled water Substances 0.000 description 2
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 2
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 description 1
- QRVASEIATBVCRN-UHFFFAOYSA-N (2,4-ditert-butyl-4-methylcyclohexa-1,5-dien-1-yl) dihydrogen phosphite Chemical compound P(O)(O)OC1=C(CC(C=C1)(C)C(C)(C)C)C(C)(C)C QRVASEIATBVCRN-UHFFFAOYSA-N 0.000 description 1
- FGHOOJSIEHYJFQ-UHFFFAOYSA-N (2,4-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=C(OP(O)O)C(C(C)(C)C)=C1 FGHOOJSIEHYJFQ-UHFFFAOYSA-N 0.000 description 1
- GGRBEFVMJHQWFG-UHFFFAOYSA-N (2-phenyl-1h-imidazol-5-yl)methanol Chemical compound OCC1=CNC(C=2C=CC=CC=2)=N1 GGRBEFVMJHQWFG-UHFFFAOYSA-N 0.000 description 1
- CVBWTNHDKVVFMI-LBPRGKRZSA-N (2s)-1-[4-[2-[6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)Br)=CC2=C1OCO2 CVBWTNHDKVVFMI-LBPRGKRZSA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
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- SWYZNMNIUXTWTF-UHFFFAOYSA-N (4-chlorophenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(Cl)C=C1 SWYZNMNIUXTWTF-UHFFFAOYSA-N 0.000 description 1
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
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- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- KVENDAGPVNAYLY-UHFFFAOYSA-N tribromo(ethyl)silane Chemical compound CC[Si](Br)(Br)Br KVENDAGPVNAYLY-UHFFFAOYSA-N 0.000 description 1
- KBSUPJLTDMARAI-UHFFFAOYSA-N tribromo(methyl)silane Chemical compound C[Si](Br)(Br)Br KBSUPJLTDMARAI-UHFFFAOYSA-N 0.000 description 1
- PQZRTKDQUBMHQJ-UHFFFAOYSA-N tribromo(oxiran-2-ylmethyl)silane Chemical compound Br[Si](Br)(Br)CC1CO1 PQZRTKDQUBMHQJ-UHFFFAOYSA-N 0.000 description 1
- HPTIEXHGTPSFDC-UHFFFAOYSA-N tribromo(phenyl)silane Chemical compound Br[Si](Br)(Br)C1=CC=CC=C1 HPTIEXHGTPSFDC-UHFFFAOYSA-N 0.000 description 1
- BMJRPFUOHCHOOB-UHFFFAOYSA-N tribromo-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound Br[Si](Br)(Br)CCCOCC1CO1 BMJRPFUOHCHOOB-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- SILWZLRRQOSOQD-UHFFFAOYSA-N tributoxy(oxiran-2-ylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CC1CO1 SILWZLRRQOSOQD-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ISCVFOODKHAEBC-UHFFFAOYSA-N trichloro(oxiran-2-ylmethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC1CO1 ISCVFOODKHAEBC-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- ABADVTXFGWCNBV-UHFFFAOYSA-N trichloro-(4-chlorophenyl)silane Chemical compound ClC1=CC=C([Si](Cl)(Cl)Cl)C=C1 ABADVTXFGWCNBV-UHFFFAOYSA-N 0.000 description 1
- XBWRLPTYWJUPKS-UHFFFAOYSA-N trichloro-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound Cl[Si](Cl)(Cl)CCCOCC1CO1 XBWRLPTYWJUPKS-UHFFFAOYSA-N 0.000 description 1
- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-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
- OKDJUBJTKGOTCQ-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC1CO1 OKDJUBJTKGOTCQ-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
- NNNBKZHPEASMSV-UHFFFAOYSA-N triethoxy-(2-methoxyphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1OC NNNBKZHPEASMSV-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- SEAZOECJMOZWTD-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethyl)silane Chemical compound CO[Si](OC)(OC)CC1CO1 SEAZOECJMOZWTD-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- IUURMAINMLIZMX-UHFFFAOYSA-N tris(2-nonylphenyl)phosphane Chemical compound CCCCCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCCCCC)C1=CC=CC=C1CCCCCCCCC IUURMAINMLIZMX-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
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- C—CHEMISTRY; METALLURGY
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Description
従来、光素子用封止材としては、耐熱性等に優れる硬化物が得られる透明エポキシ樹脂を主成分とするものが知られている。
(1)分子内に、式(A)
リン酸系触媒の存在下、式(1):R1Si(OR3)p(X1)3−p(式中、R1は前記と同じ意味を表し、R3は炭素数1〜6のアルキル基を表し、X1はハロゲン原子を表し、pは0〜3の整数を表す。)で表されるシラン化合物(1)と、式(2):R2Si(OR4)q(X2)3−q(式中、R2は前記と同じ意味を表し、R4は炭素数1〜6のアルキル基を表し、X2はハロゲン原子を表し、qは0〜3の整数を表す。)で表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=5:95〜100:0の割合で、縮合させて得られたものを主成分とする光素子用封止材。
(3)前記リン酸系触媒が、式(3)
(4)前記リン酸系触媒が、式(4)
(5)前記ポリシルセスキオキサン化合物が、重量平均分子量が1,000〜5,000の化合物であることを特徴とする(1)〜(4)のいずれかに記載の光素子用封止材。
(6)光素子が、前記(1)〜(5)のいずれかに記載の光素子用封止材の硬化物により封止されてなる光素子封止体。
本発明の光素子封止体は、本発明の光素子用封止材を用いているので、耐久性、耐熱性に優れている。
1)光素子用封止材
本発明の光素子用封止材は、分子内に、前記式(A)で表される繰り返し単位を有するラダー型構造のポリシルセスキオキサン化合物(以下、「ポリシルセスキオキサン化合物(A)」ということがある。)であって、式(1):R1Si(OR3)p(X1)3−pで表されるシラン化合物(1)と、式(2):R2Si(OR4)q(X2)3−qで表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=5:95〜100:0の割合で用いて、リン酸系触媒の存在下に縮合させて得られたものを主成分とすることを特徴とする。
本発明に用いるシラン化合物(1)において、式(1)中、R1は反応性官能基を有する基を表す。
R1の反応性官能基を有する基としては、式:−Y−Z(式中、Yは2価の連結基を表し、Zは反応性官能基を表す。)で示される基が挙げられる。
グリシドキシ基、2−グリシドキシエチル基、3−グリシドキシプロピル基、4−グリシドキシブチル基、2−(3,4−エポキシシクロヘキシル)エチル基、2−[2−(3,4−エポキシシクロヘキシルメトキシ)エトキシ)エチル基等が挙げられる。
pは0〜3の整数を表す。pが2以上のとき、複数の式:OR3で表される基同士は同一であっても相異なっていてもよく、(3−p)が2以上のとき、複数のX1同士は同一であっても相異なっていてもよい。
2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリプロポキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリブトキシシラン、
3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリプロポキシシラン、3−メタクリロキシプロピルトリブトキシシラン、
ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリプロポキシシラン、ビニルトリブトキシシラン、
3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、3−メルカプトプロピルトリプロポキシシラン、3−メルカプトプロピルトリブトキシシラン等のトリアルコキシシラン化合物類;
3−グリシドキシプロピルトリクロロシラン、3−グリシドキシプロピルクロロジメトキシシラン、3−グリシドキシプロピルジクロロメトキシシラン、3−グリシドキシプロピルクロロジエトキシシラン、3−グリシドキシプロピルジクロロエトキシシラン、3−グリシドキシプロピルトリブロモシラン、
3−メタクリロキシプロピルトリクロロシラン、3−メタクリロキシプロピルクロロジメトキシシラン、3−メタクリロキシプロピルジクロロメトキシシラン、3−メタクリロキシプロピルクロロジエトキシシラン、3−メタクリロキシプロピルジクロロエトキシシラン、3−メタクリロキシプロピルトリブロモシラン、
本発明に用いるシラン化合物(2)において、前記式(2)中、R2は、炭素数1〜20のアルキル基、又は置換基を有していてもよいフェニル基を表す。
qは0〜3の整数を表す。qが2以上のとき、複数の式:OR4で表される基同士は同一であっても相異なっていてもよく、(3−q)が2以上のとき、複数のX2同士は同一であっても相異なっていてもよい。
本発明においては、前記シラン化合物(1)とシラン化合物(2)との縮合反応における触媒としてリン酸系触媒を用いる。リン酸系触媒を用いることで、耐クラック性、耐熱性に優れる硬化物を得ることができるポリシルセスキオキサン化合物を合成することができる。
これらの中でも、式(3)又は式(4)
式(3)中、R5、R6、R7はそれぞれ独立して、水素原子、炭素数1〜8のアルキル基、又は置換基を有していてもよいフェニル基を表す。ただし、R5、R6、R7のうち、少なくとも一つは水素原子である。また、式(4)中、R8、R9、R10、R11はそれぞれ独立して、水素原子、炭素数1〜8のアルキル基、または置換基を有していてもよいフェニル基を表す。ただし、R8、R9、R10、R11のうち、少なくとも一つは水素原子である。
これらの中でも、水、芳香族炭化水素類、及びこれらの混合溶媒が好ましく、水とトルエンの混合溶媒が特に好ましい。
溶媒の使用量は、溶媒1リットルあたり、シラン化合物の総モル量が、通常0.1mol〜10mol、好ましくは0.5mol〜10molとなる量である。
得られるポリシルセスキオキサン化合物(A)は、前記式(A)で表される繰り返し単位を有するラダー型構造を有する。
前記式(A)中、l、m、nはそれぞれ独立して、0又は任意の自然数を表す。ただし、l及びnがともに0である場合は除かれる。
すなわち、得られるポリシルセスキオキサン化合物(A)は、式(a)で表される繰り返し単位の一種のみからなるホモポリマー、式(a)で表される繰り返し単位の二種以上からなる共重合体、式(a)〜(c)の繰り返し単位からなる共重合体等のいずれであってもよい(なお、本発明においては、前記(c)で表される繰り返し単位は、上下180°回転した形で結合していてもよい。)。
酸化防止剤としては、例えば、フェノール系、硫黄系、リン系酸化防止剤等が挙げられる。
紫外線吸収剤としては、例えば、フェニルサリシレート、p−t−ブチルフェニルサリシレート、p−オクチルフェニルサリシレート等のサリチル酸類;2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、2−ヒドロキシ−4−ドデシルオキシベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノン等のベンゾフェノン類;2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−tert−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジtert−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−tert−ブチル−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジtert−ブチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジtert−アミルフェニル)ベンゾトリアゾール、2−{(2’−ヒドロキシ−3’,3’’,4’’,5’’,6’’−テトラヒドロフタルイミドメチル)−5’−メチルフェニル}ベンゾトリアゾール等のベンゾトリアゾール類;ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)[{3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル}メチル]ブチルマロネート等のヒンダードアミン類;等が挙げられる。
光安定剤としては、例えば、ポリ[{6−(1,1,3,3,−テトラメチルブチル)アミノ−1,3,5−トリアジン−2,4−ジイル}{(2,2,6,6−テトラメチル−4−ピペリジン)イミノ}ヘキサメチレン{(2,2,6,6−テトラメチル−4−ピペリジン)イミノ}]等のヒンダードアミン類が挙げられる。
希釈剤としては、例えば、グリセリンジグリシジルエーテル、ブタンジオールジグリシジルエーテル、ジグリシジルアニリン、ネオペンチルグリコールグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル、アルキレンジグリシジルエーテル、ポリグリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテル、4−ビニルシクロヘキセンモノオキサイド、ビニルシクロヘキセンジオキサイド、メチル化ビニルシクロヘキセンジオキサイド等が挙げられる。これらの希釈剤は1種単独で、あるいは2種以上を組み合わせて使用することができる。
シランカップリング剤としては、例えば、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン等が挙げられる。
これらは1種単独で、あるいは2種以上を組み合わせて用いることができる。
これらは1種単独で、あるいは2種以上を組み合わせて用いることができる。
また、本発明の光素子用封止材の硬化物が耐熱性に優れることは、例えば、光素子用封止材の硬化物を、高温下で長時間(例えば、150℃で100時間)置き、透過率の低下がほとんど見られないことで確認することができる。
本発明の光素子封止体は、光素子が、本発明の光素子用封止材の硬化物により封止されてなるものである。
すなわち、Lamp型のLED封止体(10A)は、図2(a)、(b)に示す、ランプ形状の凹部を有する鋳型(2)を使用して製造することができる。なお、図2(a)は鋳型(2)のX−Y方向の断面図、図2(b)は鋳型(2)の上面図である。
攪拌子を入れた200mlのナス型フラスコに、フェニルトリメトキシシラン(東京化成工業社製)3.97g(20mmol)、3−グリシドキシプロピルトリメトキシシラン(東京化成工業社製)4.73g(20mmol)、トルエン20ml、及び蒸留水10mlを仕込んだ後、全容を撹拌しながら、リン酸(関東化学社製)0.10g(1mmol)を加え、室温で16時間さらに撹拌を継続した。反応終了後、反応混合物に飽和炭酸水素ナトリウム水溶液を加えて中和した。しばらく静置した後、トルエン及び水を除去し、残留物を蒸留水にて2回洗浄した。得られた残留物を2−ブタノン100mlに溶解させ、無水硫酸マグネシウムで乾燥した。無水硫酸マグネシウムをろ別後、ろ液を多量のn−ヘキサン中に滴下して再沈殿させた。n−ヘキサンを除去後、沈殿物をテトラヒドロフラン(THF)に溶解して回収し、エバポレーターでTHFを減圧留去し、真空乾燥することにより、ポリシルセスキオキサン化合物を得た。添加剤を加えず、この化合物単独で光素子用封止材とした。
実施例1において、触媒として、リン酸の代わりにフェニルリン酸(東京化成工業社製)0.18g(1mmol)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりにリン酸ジフェニル(東京化成工業社製)0.25g(1mmol)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりにメチレンジホスホン酸(東京化成工業社製)0.09g(0.5mmol)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、フェニルトリメトキシシラン及び3−グリシドキシプロピルトリメトキシシランの使用量を、フェニルトリメトキシシラン5.95g(30mmol)、3−グリシドキシプロピルトリメトキシシラン2.36g(10mmol)とした他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、フェニルトリメトキシシラン3.97g(20mmol)及び3−グリシドキシプロピルトリメトキシシラン4.73g(20mmol)の代わりに、フェニルトリメトキシシラン5.95g(30mmol)、3−メタクリロイロキシプロピルトリメトキシシラン(東京化成工業社製)2.48g(10mmol)を用いた以外は実施例1と同様に反応を行った。反応終了後、反応溶液に飽和炭酸水素ナトリウム水溶液を添加して中和した後、トルエン層を分取した。有機層を無水硫酸マグネシウムで乾燥し、硫酸マグネシウムをろ別した。得られたろ液を多量のn−ヘキサン中に滴下して再沈殿させた。n−ヘキサンを除去後、沈殿物をTHFに溶解させて回収し、エバポレーターでTHFを除去した後、残留物を真空乾燥して、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、フェニルトリメトキシシラン3.97g(20mmol)及び3−グリシドキシプロピルトリメトキシシラン4.73g(20mmol)の代わりに、フェニルトリメトキシシラン5.95g(30mmol)、3−メルカプトプロピルトリメトキシシラン(東京化成工業社製)1.96g(10mmol)を用いた以外は実施例1と同様に反応を行った。反応終了後、反応溶液に飽和炭酸水素ナトリウム水溶液を添加して中和した後、トルエン層を分取した。有機層を無水硫酸マグネシウムで乾燥し、硫酸マグネシウムをろ別した。得られたろ液を多量のn−ヘキサン中に滴下して再沈殿させた。n−ヘキサンを除去後、沈殿物をTHFに溶解させて回収し、エバポレーターでTHFを除去した後、残留物を真空乾燥して、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
20mlのガラス製サンプル管に、実施例1で得たポリシルセスキオキサン化合物(1)3gに、酸化防止剤として、ペンタエリスリトールテトラキス[3−(3’,5’−ジ−tert−ブチル−4’−ヒドロキシフェニル)プロピオネート](別名:テトラキス−[メチレン−3−(3’,5’−ジ−t−ブチル−4’−ヒドロキシフェニル)プロピオネート]メタン)(東京化成工業社製)0.03gを添加し、全容を十分に混合して、光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりにメタンスルホン酸(東京化成工業社製)0.10g(1mmol)を用いた他は、実施例1と同様にしてポリシルセスキオキサン化合物を得た。添加剤を加えず、単独で光素子用封止材とした。
実施例1において、触媒として、リン酸の代わりに硝酸(関東化学社製)0.06g(1mmol)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりに塩酸(関東化学社製)0.10g(1mmol、塩化水素として換算)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりにトリエチルアミン(関東化学社製)0.10g(1mmol)を用いた他は、実施例1と同様にして、ポリシルセスキオキサン化合物及び光素子用封止材を得た。
実施例1において、触媒として、リン酸の代わりに水酸化テトラメチルアンモニウム10重量%水溶液(アルドリッチ社製)0.91g(1mmol,水酸化テトラメチルアンモニウム換算)を用いた他は、実施例1と同様にしてポリシルセスキオキサン化合物の製造を試みたが、ゲル化して、目的物を得ることができなかった。
20mlのガラス製サンプル管に、3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート(アルドリッチ社製)2g、2,2−ビス(4−グリシジルオキシフェニル)プロパン(東京化成工業社製)1g、4−メチルシクロヘキサン−1,2−ジカルボン酸無水物(東京化成工業社製)3g、及びトリフェニルホスフィン(関東化学社製)0.03gを添加し、全容を十分に混合して、エポキシ樹脂組成物よりなる光素子用封止材を得た。
測定結果を第1表に示す。
重量平均分子量(Mw)は、テトラヒドロフラン(THF)を溶媒とするゲル・パーミエーション・クロマトグラフィー(GPC)による標準ポリスチレン換算値として測定した。
カラム:TSKgelGMHXL→TSKgelGMHXL→TSKgel2000HXL
溶媒:THF
測定温度:40℃
流速:1ml/分
検出器:示差屈折計
実施例1〜7、及び比較例1〜5で得たポリシルセスキオキサン化合物、並びに実施例8及び比較例6で得た樹脂組成物のそれぞれを、長さ25mm、幅20mm、厚さ1mmとなるように鋳型に流し込み、125℃で6時間加熱して硬化させ、試験片をそれぞれ作製した。得られた試験片を150℃のオーブンに24時間入れた後、試験片の状態を目視にて確認し、クラックが観察されなかった場合を○、クラックが観察された場合を×として評価した。結果を下記第1表に示す。
実施例1〜7、及び比較例1〜5で得たポリシルセスキオキサン化合物、並びに実施例8及び比較例6で得た樹脂組成物のそれぞれを、長さ25mm、幅20mm、厚さ1mmとなるように鋳型に流し込み、125℃で6時間加熱して硬化させ、試験片をそれぞれ作製した。得られた試験片につき、分光光度計(MPC−3100、島津製作所社製)にて、400nm、450nm、500nmの初期透過率を求めた。
初期透過率を測定した各試験片を150℃のオーブンに100時間投入し、再度400nm、450nm、500nmの加熱後透過率を求めた。測定結果を下記第1表に示す。
比較例3の光素子用封止材は、耐クラック性及び耐熱性に劣っていた。
比較例4のポリシルセスキオキサン化合物は重量平均分子量が8800と大きく、成形加工をすることができなかった。
比較例5の場合には、反応混合物がゲル化して、目的物を得ることができなかった。
比較例6の光素子用封止材は、特に400nmの光に対する透明性が低く、また、耐熱試験後の透過率の低下も大きかった。
Claims (6)
- 分子内に、式(A)
リン酸系触媒の存在下、式(1):R1Si(OR3)p(X1)3−p(式中、R1は前記と同じ意味を表し、R3は炭素数1〜6のアルキル基を表し、X1はハロゲン原子を表し、pは0〜3の整数を表す。)で表されるシラン化合物(1)と、式(2):R2Si(OR4)q(X2)3−q(式中、R2は前記と同じ意味を表し、R4は炭素数1〜6のアルキル基を表し、X2はハロゲン原子を表し、qは0〜3の整数を表す。)で表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=5:95〜100:0の割合で、縮合させて得られたものを主成分とする光素子用封止材。 - 前記ポリシルセスキオキサン化合物が、前記式(A)中、R1が、反応性環状エーテル基、アルケニル基、メタクリロイル基、アクリロイル基、またはメルカプト基を有する基である化合物であることを特徴とする請求項1に記載の光素子用封止材。
- 前記ポリシルセスキオキサン化合物が、重量平均分子量が1,000〜5,000の化合物であることを特徴とする請求項1〜4のいずれかに記載の光素子用封止材。
- 光素子が、請求項1〜5のいずれかに記載の光素子用封止材の硬化物により封止されてなる光素子封止体。
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JP4365771B2 (ja) * | 2004-11-26 | 2009-11-18 | 東亞合成株式会社 | 硬化性組成物 |
JP2006328231A (ja) * | 2005-05-26 | 2006-12-07 | Nagase Chemtex Corp | 光素子用封止樹脂組成物 |
JP2007009080A (ja) * | 2005-06-30 | 2007-01-18 | Nagase Chemtex Corp | 光学コーティング組成物 |
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JP2008266585A (ja) | 2008-11-06 |
TWI421282B (zh) | 2014-01-01 |
US20110288257A1 (en) | 2011-11-24 |
US8470953B2 (en) | 2013-06-25 |
KR20080088441A (ko) | 2008-10-02 |
KR101412945B1 (ko) | 2014-06-26 |
US20080249278A1 (en) | 2008-10-09 |
US8026332B2 (en) | 2011-09-27 |
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