JP5425406B2 - ポリシルセスキオキサン化合物からなる成形材料、封止材および光素子封止体 - Google Patents
ポリシルセスキオキサン化合物からなる成形材料、封止材および光素子封止体 Download PDFInfo
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- JP5425406B2 JP5425406B2 JP2008051568A JP2008051568A JP5425406B2 JP 5425406 B2 JP5425406 B2 JP 5425406B2 JP 2008051568 A JP2008051568 A JP 2008051568A JP 2008051568 A JP2008051568 A JP 2008051568A JP 5425406 B2 JP5425406 B2 JP 5425406B2
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- 230000003287 optical effect Effects 0.000 title claims description 91
- 150000001875 compounds Chemical class 0.000 title claims description 57
- 239000003566 sealing material Substances 0.000 title claims description 54
- 229920000734 polysilsesquioxane polymer Polymers 0.000 title claims description 46
- 239000012778 molding material Substances 0.000 title claims description 39
- 238000007789 sealing Methods 0.000 title claims description 24
- -1 silane compound Chemical class 0.000 claims description 107
- 229910000077 silane Inorganic materials 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000008393 encapsulating agent Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- 238000002834 transmittance Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- FZTPAOAMKBXNSH-UHFFFAOYSA-N 3-trimethoxysilylpropyl acetate Chemical compound CO[Si](OC)(OC)CCCOC(C)=O FZTPAOAMKBXNSH-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- HYFWOBSAALCFRS-UHFFFAOYSA-N 3-trimethoxysilylpropyl benzoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C1=CC=CC=C1 HYFWOBSAALCFRS-UHFFFAOYSA-N 0.000 description 3
- BBKDTSUKGUBWBP-UHFFFAOYSA-N 3-trimethoxysilylpropyl pentanoate Chemical compound CCCCC(=O)OCCC[Si](OC)(OC)OC BBKDTSUKGUBWBP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000012044 organic layer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- PWYXVVREDGESBB-UHFFFAOYSA-N Allyl valerate Chemical compound CCCCC(=O)OCC=C PWYXVVREDGESBB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 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
- 239000002131 composite material Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- GSKJMEQNVZJJIL-UHFFFAOYSA-N dichloromethoxy(propyl)silane Chemical compound C(CC)[SiH2]OC(Cl)Cl GSKJMEQNVZJJIL-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 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
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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
- 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 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 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
- VNFXPOAMRORRJJ-UHFFFAOYSA-N (4-octylphenyl) 2-hydroxybenzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1OC(=O)C1=CC=CC=C1O VNFXPOAMRORRJJ-UHFFFAOYSA-N 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- 229940117900 2,2-bis(4-glycidyloxyphenyl)propane Drugs 0.000 description 1
- STHGLRYNMROMHZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-11-methyl-3-(8-methylnonyl)dodecane-1,3-diol Chemical compound C(CCCCCCC(C)C)C(O)(C(CO)(CO)CO)CCCCCCCC(C)C STHGLRYNMROMHZ-UHFFFAOYSA-N 0.000 description 1
- OOLRKFOQCFQRGU-UHFFFAOYSA-N 2,2-dichloroethoxy(3-trityloxypropyl)silane Chemical compound C1(=CC=CC=C1)C(OCCC[SiH2]OCC(Cl)Cl)(C1=CC=CC=C1)C1=CC=CC=C1 OOLRKFOQCFQRGU-UHFFFAOYSA-N 0.000 description 1
- HXWIPNSVUABLTP-UHFFFAOYSA-N 2,2-dichloroethoxy(oxiran-2-ylmethyl)silane Chemical compound C(C1CO1)[SiH2]OCC(Cl)Cl HXWIPNSVUABLTP-UHFFFAOYSA-N 0.000 description 1
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- JZYKVBRBIWTMEB-UHFFFAOYSA-N triethoxy(3-triethylsilyloxypropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCO[Si](CC)(CC)CC JZYKVBRBIWTMEB-UHFFFAOYSA-N 0.000 description 1
- XFPXEXSXVSCKQC-UHFFFAOYSA-N triethoxy(3-trityloxypropyl)silane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC[Si](OCC)(OCC)OCC)C1=CC=CC=C1 XFPXEXSXVSCKQC-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
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-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
- PGBUIPONYKQQMF-UHFFFAOYSA-N triethoxy-[3-(2-methoxyethoxymethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCOCCOC PGBUIPONYKQQMF-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- YOGRNCSVLDKNCY-UHFFFAOYSA-N trimethoxy(2-trimethylsilyloxyethyl)silane Chemical compound CO[Si](OC)(OC)CCO[Si](C)(C)C YOGRNCSVLDKNCY-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
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-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
- YFFNIIAVGWYOQJ-UHFFFAOYSA-N trimethoxy-[3-(methoxymethoxy)propyl]silane Chemical compound COCOCCC[Si](OC)(OC)OC YFFNIIAVGWYOQJ-UHFFFAOYSA-N 0.000 description 1
- SAKLXMOLLSWVHU-UHFFFAOYSA-N trimethoxy-[3-[(2-methylpropan-2-yl)oxy]propyl]silane Chemical compound CO[Si](OC)(OC)CCCOC(C)(C)C SAKLXMOLLSWVHU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 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
- 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
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/02—Containers; Seals
- H01L23/10—Containers; Seals characterised by the material or arrangement of seals between parts, e.g. between cap and base of the container or between leads and walls of the container
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/133—Rod-like building block
- C08G2261/1336—Ladder-type, e.g. ladder-poly-p-phenylenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/4805—Shape
- H01L2224/4809—Loop shape
- H01L2224/48091—Arched
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(I)
(5)硬化剤を含まないことを特徴とする(1)〜(4)のいずれかに記載の成形材料。
(6)(1)〜(5)のいずれかに記載の成形材料を用いることを特徴とする封止材。
(7)光素子用封止材であることを特徴とする(6)に記載の封止材。
本発明の第3によれば、下記(8)の光素子封止体が提供される。
(8)光素子が、(7)に記載の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、本発明の成形材料を用いているので、耐熱性に優れ、長期にわたって使用した場合であっても、着色劣化が少ない。
1)成形材料
本発明の成形材料は、分子内に、前記式(I)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(I)」ということがある。)を主成分とすることを特徴とする。
Aは水酸基の保護基を表す。水酸基の保護基としては、特に制約はなく、水酸基の保護基として知られている公知の保護基が挙げられる。例えば、アセチル基、プロピオニル基、ベンゾイル基等のアシル系の保護基;トリメチルシリル基、トリエチルシリル基、tert−ブチルジメチルシリル基、t−ブチルジフェニルシリル基などのシリル系の保護基;メトキシメチル基、メトキシエトキシメチル基、1−エトキシエチル基、テトラヒドロピラン−2−イル基、テトラヒドロフラン−2−イル基などのアセタール系の保護基;tert−ブトキシカルボニル基などのアルコキシカルボニル系の保護基;メチル基、エチル基、t−ブチル基、オクチル基、アリル基、トリフェニルメチル基、ベンジル基、p−メトキシベンジル基、フルオレニル基、トリチル基、ベンズヒドリル基等のエーテル系の保護基;等が挙げられる。
これらの中でも、耐熱性に優れ、長期にわたって着色劣化が少ない成形材料が得られることから、アシル系の保護基が好ましく、アセチル基が特に好ましい。
これらの中でも、R1としては、式:R5C(=O)−O−(CH2)3−(式中、R5は、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、t−ブチル基、n−ペンチル基等の炭素数1〜6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。ここで、置換基を有していてもよいフェニル基の置換基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、イソブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、イソオクチル基等のアルキル基;フッ素原子、塩素原子、臭素原子等のハロゲン原子;メトキシ基、エトキシ基等のアルコキシ基;が挙げられる。)で表される基が好ましく、前記R5がメチル基である3−アセトキシプロピル基〔CH3C(=O)−O−(CH2)3−〕が特に好ましい。
ポリシルセスキオキサン化合物(I)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、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。)。
前記式(1)中、R3は、炭素数1〜6のアルキル基を表す。炭素数1〜6のアルキル基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、イソブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基等が挙げられる。これらの中でも、経済性、取り扱い容易性等の観点から、メチル基、エチル基が好ましい。
pは0〜3のいずれかの整数を表す。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。
これらのシラン化合物は一種単独で、あるいは2種以上を組み合わせて用いることができる。
qは0〜3のいずれかの整数を表す。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。
フェニルトリクロロシラン、フェニルクロロジメトキシシラン、フェニルジクロロメトキシシラン、フェニルトリブロモシラン、フェニルクロロメトキシエトキシシラン、4−クロロフェニルトリクロロシラン、フェニルトリクロロシラン、2−メトキシフェニルトリクロロシラン;等の置換基を有していてもよいフェニルシラン化合物類;
メチルトリクロロシラン、メチルクロロジメトキシシラン、メチルジクロロメトキシシラン、メチルトリブロモシラン、メチルクロロジエトキシシラン、エチルトリクロロシラン、エチルクロロジメトキシシラン、エチルジクロロメトキシシラン、エチルトリブロモシラン、n−プロピルトリクロロシラン、n−プロピルクロロジメトキシシラン、n−プロピルジクロロメトキシシラン等のアルキルシラン化合物類;
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、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、
これらのシラン化合物は一種単独で、あるいは2種以上を組み合わせて用いることができる。
酸触媒としては、塩酸、硫酸、硝酸、りん酸等の無機酸;メタンスルホン酸、トリフルロロメタンスルホン酸、ベンゼンスルホン酸、p−トルエンスルホン酸、酢酸、トリフルオロ酢酸等の有機酸;が挙げられる。
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、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピ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、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。
本発明の光素子封止体は、光素子が、本発明の光素子用の封止材(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(12)を使用して製造することができる。なお、図2(a)は鋳型(12)のX−Y方向の断面図、図2(b)は鋳型(12)の上面図である。
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
攪拌子を入れた200mlのナス型フラスコに、シラン化合物(2)としてフェニルトリメトキシシラン(東京化成工業社製)3.97g(20mmol)、シラン化合物(1)として3−アセトキシプロピルトリメトキシシラン(アヅマックス社製)4.45g(20mmol)、溶媒としてトルエン20ml、及び蒸留水10mlを仕込んだ後、全容を撹拌しながら、触媒としてリン酸(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(重量平均分子量(Mw)=2,400)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(重量平均分子量(Mw)=2,500)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(東京化成工業社製)0.10g(1mmol)を用いた他は、実施例1と同様に反応させた。反応混合物に、酢酸エチル50ml及びTHF50mlを添加した後、0.1N塩酸を加えて中和した。しばらく静置した後、有機層を回収し、蒸留水にて2回洗浄し、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(重量平均分子量(Mw)=6,500)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、フェニルトリメトキシシラン及び3−アセト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−アセトキシプロピルトリメトキシシラン2.22g(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(重量平均分子量(Mw)=2,900)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−アセト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1.98g(10mmol)、3−アセトキシプロピルトリメトキシシラン6.67g(30mmol)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(重量平均分子量(Mw)=1,800)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−アセト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3.97g(20mmol)、3−アセトキシプロピルトリメトキシシラン4.00g(18mmol)とし、さらに、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)0.47g(2mmol)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(重量平均分子量(Mw)=2,500)及び光素子用封止材を得た。
温度計及び塩化カルシウム管を備え付けた50mlの2口ナスフラスコに攪拌子を入れ、吉草酸アリル(アルドリッチ社製)5.13g(40mmol)、及び白金触媒(商品名:BY 24-835、東レ・ダウコーニング社製)0.2gを仕込んだ後、全容を攪拌しながら反応温度が50℃を超えないようにしながら、トリメトキシシラン(東京化成工業社製)4.89g(40mmol)をゆっくりと加えた。その後さらに白金触媒を0.2g添加し、室温で6時間反応させた。反応終了後、反応液をクーゲルロール蒸留装置にて減圧蒸留を行うことにより、シラン化合物(1)である吉草酸3−トリメトキシシリルプロピルを8.12g得た。
製造例1において、吉草酸アリル40mmolに代えて、安息香酸アリル(東京化成工業社製)6.49g(40mmol)を用いた以外は製造例1と同様に操作を行い、シラン化合物(1)である安息香酸3−トリメトキシシリルプロピルを7.97g得た。
実施例1において、シラン化合物(1)として、3−アセトキシプロピルトリメトキシシラン4.45g(20mmol)に代えて、製造例1で合成した吉草酸3−トリメトキシシリルプロピル5.01g(20mmol)を用いた以外は、実施例1と同様に反応させた。その後、反応液に酢酸エチル50mlを添加し、飽和炭酸水素ナトリウム水溶液にて反応溶液を中和した後、有機層を分取した。有機層を蒸留水にて2回洗浄した後、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、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、エバポレータでTHFを除去後、得られた残留物を真空乾燥することにより、目的とするポリシルセスキオキサン化合物(重量平均分子量(Mw)=2,800)及び光素子用封止材を得た。
実施例7において、シラン化合物(1)として、吉草酸3−トリメトキシシリルプロピル5.01g(20mmol)に代えて、製造例2で合成した安息香酸3−トリメトキシシリルプロピル5.69g(20mmol)を用いた以外は、実施例7と同様にして、ポリシルセスキオキサン化合物(重量平均分子量(Mw)=3,100)及び光素子用封止材を得た。
実施例1において、シラン化合物(1)である3−アセトキシプロピルトリメトキシシランの代わりに、3−グリシドキシプロピルトリメトキシシラン4.73g(20mmol)を用い、りん酸の代わりにメタンスルホン酸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(重量平均分子量(Mw)=2,200)及び光素子用封止材を得た。
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。
ポリシルセスキオキサン化合物を、長さ25mm、幅20mm、厚さ1mmとなるように鋳型に流し込み、135℃で12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、波長365nm、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時間及び500時間投入し、再度、波長365nm、400nm、450nm、500nmの加熱後透過率を求めた。
波長400nmにおける初期透過率が、85%以上のものを○、70%以上85%未満のものを△、70%未満のものを×、と評価した。
波長400nmにおける初期透過率と、150℃、500時間の加熱後透過率から、下記式の値を算出し、70以上のものを○、50以上70未満のものを△、50未満のものを×、と評価した。
比較例2の光素子用封止材は、初期透過率(特に波長365nm、400nmにおける透過率)が劣り、耐熱試験後の透過率の低下も大きかった。
Claims (7)
- 分子内に、式(I)
前記ポリシルセスキオキサン化合物が、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)]=25:75〜60:40の割合で、縮合させて得られたものであることを特徴とする成形材料。 - 前記ポリシルセスキオキサン化合物が、前記式(I)中、R1が、式:R5C(=O)−O−(CH2)3−(式中、R5は炭素数1〜6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。)で示される基の化合物であることを特徴とする請求項1に記載の成形材料。
- 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1,000〜10,000の化合物であることを特徴とする請求項1または2に記載の成形材料。
- 硬化剤を含まないことを特徴とする請求項1〜3のいずれかに記載の成形材料。
- 請求項1〜4のいずれかに記載の成形材料を用いることを特徴とする封止材。
- 光素子用封止材であることを特徴とする請求項5に記載の封止材。
- 光素子が、請求項6に記載の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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TW097119854A TWI429687B (zh) | 2007-06-29 | 2008-05-29 | A molding material formed of a polytrimisiloxane compound, a sealing material, and an optical element sealing body |
US12/213,283 US8481669B2 (en) | 2007-06-29 | 2008-06-17 | Molding material comprising polysilsesquioxane compound, sealing material, and sealed optical element |
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