JP6350887B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP6350887B2 JP6350887B2 JP2017042557A JP2017042557A JP6350887B2 JP 6350887 B2 JP6350887 B2 JP 6350887B2 JP 2017042557 A JP2017042557 A JP 2017042557A JP 2017042557 A JP2017042557 A JP 2017042557A JP 6350887 B2 JP6350887 B2 JP 6350887B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- chemical formula
- sio
- polyorganosiloxane
- positive number
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 123
- 239000000126 substance Substances 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000003700 epoxy group Chemical group 0.000 claims description 36
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001923 cyclic compounds Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 14
- 239000004065 semiconductor Substances 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 150000003377 silicon compounds Chemical class 0.000 claims description 14
- 239000002954 polymerization reaction product Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- 238000001723 curing Methods 0.000 description 18
- 150000002430 hydrocarbons Chemical group 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 15
- -1 cyclic siloxane compound Chemical class 0.000 description 14
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000003566 sealing material Substances 0.000 description 10
- 230000035939 shock Effects 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 238000006459 hydrosilylation reaction Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004954 Polyphthalamide Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920006375 polyphtalamide Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- VSIKJPJINIDELZ-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octakis-phenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VSIKJPJINIDELZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CXYAFFSHJZNAKZ-UHFFFAOYSA-N C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C.C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C Chemical compound C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C.C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C CXYAFFSHJZNAKZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005417 glycidoxyalkyl group Chemical group 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- GRGVQLWQXHFRHO-AATRIKPKSA-N (e)-3-methylpent-3-en-1-yne Chemical compound C\C=C(/C)C#C GRGVQLWQXHFRHO-AATRIKPKSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- XWERKWVETTXNQX-UHFFFAOYSA-N 2,3-dimethyl-1,4-dioxine Chemical compound CC1=C(C)OC=CO1 XWERKWVETTXNQX-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GTCVHDLNCRYGPU-UHFFFAOYSA-N C[N+](C)(C)C.C(=C)[Si](O[Si](C)(C)C)(C)C=C Chemical compound C[N+](C)(C)C.C(=C)[Si](O[Si](C)(C)C)(C)C=C GTCVHDLNCRYGPU-UHFFFAOYSA-N 0.000 description 1
- RCXOWABOBJOXSI-UHFFFAOYSA-N C[SiH]1O[SiH](O[SiH](O[SiH](O1)C)C)C.C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C Chemical compound C[SiH]1O[SiH](O[SiH](O[SiH](O1)C)C)C.C[Si]1(O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)C RCXOWABOBJOXSI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- QQQCWVDPMPFUGF-ZDUSSCGKSA-N alpinetin Chemical compound C1([C@H]2OC=3C=C(O)C=C(C=3C(=O)C2)OC)=CC=CC=C1 QQQCWVDPMPFUGF-ZDUSSCGKSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001444 catalytic combustion detection Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- DIIUFWYILXGGIL-UHFFFAOYSA-N ethynylcyclohexane Chemical compound [C]#CC1CCCCC1 DIIUFWYILXGGIL-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
- C09J183/14—Adhesives based on 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; Adhesives based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Led Device Packages (AREA)
- Silicon Polymers (AREA)
Description
(R1R2SiO2/2)
(R3 2SiO2/2)
(R4 3SiO1/2)a(R4 2SiO2/2)b(R4SiO3/2)c(SiO4/2)d
(R5R6 2SiO1/2)e(R7R8SiO2/2)f(R9 2SiO2/2)g(R10SiO3/2)h
[RjSiO3/2]
[RkRl 2SiO1/2]p[RmSiO3/2]q
(RnRo 2Si)2O
(R11 3SiO1/2)a(R11 2SiO2/2)b(R11SiO3/2)c(SiO4/2)d
R12 3SiO(R12 2SiO)nSiR12 3
(R13 3SiO1/2)a(R13 2SiO2/2)b(R13SiO3/2)c(SiO2)d
(R14 3SiO1/2)a(R14 2SiO2/2)b(R14SiO3/2)c(SiO4/2)d
ポリフタルアミド(PPA)で製造された7030 LEDパッケージを使用して素子特性を評価する。具体的に、ポリフタルアミドコップ内に硬化性組成物をディスフェンシングし、70℃で30分間維持した後、さらに150℃で1時間維持して硬化させて、表面実装型LEDを製造する。その後、下記提示された方法によってテストを進行する。
LEDを200Lのガラス瓶の容器に入れ、硫黄粉末0.2gをさらに投入した後、70℃で40時間維持した後、光束を測定し、初期光束に比べて光束の低下率を測定し、下記基準によって評価する。
A: 初基輝度に比べて輝度減少率が15%以下の場合
B: 初基に比べて輝度減少率が15%を超過し、20%以下の場合
C: 初基に比べて輝度減少率が20%を超過する場合
LEDを85℃及び85%の相対湿度の条件で維持した状態で30mAの電流を流しながら500時間動作させる。次いで、動作前の初基輝度に対して動作後の輝度減少率を測定し、下記基準で評価する。
A:初基輝度に比べて輝度減少率が5%以下の場合
B:初基に比べて輝度減少率が5%を超過し、7%以下の場合
C:初基に比べて輝度の減少率が7%を超過する場合
それぞれ下記の化学式A〜Eで表示される化合物を混合して、ヒドロシリル化反応によって硬化する硬化性組成物を製造した(配合量:化学式A:70g、化学式B:200g、化学式C:20g、化学式D:50g、化学式E:4g).上記で化学式Aのポリオルガノシロキサンは、オクタメチルシクロテトラシロキサン(octamethylcyclotetrasiloxane)及びオクタフェニルシクロテトラシロキサン(octaphenylcyclotetrasiloxane)の混合物をジビニルテトラメチルジシロキサン(divinyltetramethyldisiloxane)と混合した状態で触媒であるテトラメチルアンモニウムヒドロキシド(TMAH;tetramethylammonium hydroxide)存在の下に約115℃の温度で約20時間反応させて製造した。その後、公知の精製方法でGPCで測定した分子量800以下の環状化合物(上記化学式6でRa及びRbが共にメチル基であり、Rcは、フェニル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約7%となるようにした後に、硬化性組成物の製造に使用した。化学式Aのポリオルガノシロキサン以外の他の化合物は、公知の合成法で製造した。次いで、上記組成物にPt(0)の含量が10ppmになる量で触媒(Platinum(0)−1、3−divinyl−1、1、3、3−tetramethyldisiloxane)を配合し、均一に混合し、硬化性組成物を製造した。
(ViMe2SiO1/2)2(Me2SiO2/2)18(Ph2SiO2/2)14
[化学式B]
(ViMe2SiO1/2)2(MePhSiO2/2)0.1(PhSiO3/2)6
[化学式C]
(HMe2SiO1/2)2(MePhSiO2/2)1.5
[化学式D]
(HMe2SiO1/2)2(Ph2SiO2/2)1.5
[化学式E]
(ViMe2SiO1/2)2(EpSiO3/2)3(MePhSiO2/2)20
実施例1と同一の方式で硬化性組成物を製造した。但し、化学式Aのポリオルガノシロキサンの場合、合成反応後に精製工程を通じてGPCで測定された分子量800以下の環状化合物(上記化学式6でRa及びRbが共にメチル基であり、Rcは、フェニル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約5%になるようにした。
実施例1と同一の方式で硬化性組成物を製造した。但し、化学式Aのポリオルガノシロキサンの場合、合成反応後に精製工程を通じてGPCで測定された分子量800以下の環状化合物(上記化学式6でRa及びRbが共にメチル基であり、Rcは、フェニル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約2%になるようにした。
それぞれ下記の化学式F、B、D及びEで表示される化合物を混合し、ヒドロシリル化反応によって硬化する硬化性組成物を製造した(配合量:化学式F:70g、化学式B:200g、化学式D:70g、化学式E:4g).上記で化学式Fのポリオルガノシロキサンは、オクタメチルシクロテトラシロキサン(octamethylcyclotetrasiloxane)及びオクタフェニルシクロテトラシロキサン(octaphenylcyclotetrasiloxane)の混合物をジビニルテトラメチルジシロキサン(divinyltetramethyldisiloxane)と混合した状態で触媒であるテトラメチルアンモニウムヒドロキシド(TMAH;tetramethylammonium hydroxide)の存在の下に約115℃の温度で約20時間反応させて製造した。その後、公知の精製方法でGPCで測定した分子量800以下の環状化合物(上記化学式6でRa及びRbが共にメチル基であり、Rcは、フェニル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約2%になるようにした後に、硬化性組成物の製造に使用した。化学式Fのポリオルガノシロキサン以外の他の化合物は、公知の合成法で製造した。次いで、上記組成物にPt(0)の含量が10ppmになる量で触媒(Platinum(0)−1、3−divinyl−1、1、3、3−tetramethyldisiloxane)を配合し、均一に混合して硬化性組成物を製造した。
(ViMe2SiO1/2)2(Me2SiO2/2)14(Ph2SiO2/2)16
[化学式B]
(ViMe2SiO1/2)2(MePhSiO2/2)0.1(PhSiO3/2)6
[化学式D]
(HMe2SiO1/2)2(Ph2SiO2/2)1.5
[化学式E]
(ViMe2SiO1/2)2(EpSiO3/2)3(MePhSiO2/2)20
下記の化学式G、B、C、D及びEで表示される化合物を混合し、ヒドロシリル化反応によって硬化する硬化性組成物を製造した(配合量:化学式G:70g、化学式B:200g、化学式C:20g、化学式D:50g、化学式E:4g)。上記で化学式Gのポリオルガノシロキサンは、オクタメチルシクロテトラシロキサン(octamethylcyclotetrasiloxane)及びテトラメチルテトラフェニルシクロテトラシロキサン(tetramethyltetraphenylcyclotetrasiloxane)の混合物をジビニルテトラメチルジシロキサン(divinyltetramethyldisiloxane)と混合した状態で触媒であるテトラメチルアンモニウムヒドロキシド(TMAH;tetramethylammonium hydroxide)の存在の下に反応させて製造した。その後、公知の精製方法でGPCで測定した分子量800以下の環状化合物(上記化学式6に該当する化合物は含まず、上記化学式6でRa及びRbが共にメチル基であり、2個のRcのうち一つは、フェニル基であり、他の一つは、メチル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約7%になるようにした後に、硬化性組成物の製造に使用した。化学式Gのポリオルガノシロキサン以外の他の化合物は、公知の合成法で製造した。次いで、上記組成物にPt(0)の含量が10ppmになる量で触媒(Platinum(0)−1、3−divinyl−1、1、3、3−tetramethyldisiloxane)を配合し、均一に混合して硬化性組成物を製造した。
(ViMe2SiO1/2)2(Me2SiO2/2)4(MePhSiO2/2)20
[化学式B]
(ViMe2SiO1/2)2(MePhSiO2/2)0.1(PhSiO3/2)6
[化学式C]
(HMe2SiO1/2)2(MePhSiO2/2)1.5
[化学式D]
(HMe2SiO1/2)2(Ph2SiO2/2)1.5
[化学式E]
(ViMe2SiO1/2)2(EpSiO3/2)3(MePhSiO2/2)20
実施例1と同一の方式で硬化性組成物を製造した。但し、化学式Aのポリオルガノシロキサンの場合、合成反応後に精製工程を通じてGPCで測定された分子量800以下の環状化合物(上記化学式6でRa及びRbが共にメチル基であり、Rcは、フェニル基であり、m及びnがそれぞれ0〜4の範囲内であり、m+nが1〜8の範囲内である化合物を含む)の重量の比率が約15%となるようにした。
Claims (11)
- 下記化学式5の平均組成式を有し、R5はアルケニル基、R6はアルキル基、R7及びR8はそれぞれ独立にアルキル基またはアリール基、R9はアリール基、eは正の数、fは正の数、gは正の数、hは0である線形構造ポリオルガノシロキサン;
下記化学式5の平均組成式を有し、R5はアルケニル基、R6はアルキル基、R7及びR8はそれぞれ独立にアルキル基またはアリール基、R10はアリール基、eは正の数、fは正の数、gは0、hは 正の数である部分架橋構造ポリオルガノシロキサン;
下記化学式5の平均組成式を有し、R5はアルケニル基、R6はアルキル基、R7及びR8はそれぞれ独立にアルキル基またはアリール基、R10はエポキシ基、eは正の数、fは正の数、gは0、hは 正の数である部分架橋構造ポリオルガノシロキサン;
重量平均分子量が800以下の環状化合物;及び
ケイ素原子に結合している水素原子を含むケイ素化合物を含み、
上記環状化合物は下記化学式6で表示される化合物を含み、
上記環状化合物の比率は0重量%超過〜7重量%以下である、硬化性組成物:
[化学式5]
(R5R6 2SiO1/2)e(R7R8SiO2/2)f(R9 2SiO2/2)g(R10SiO3/2)h
- 部分架橋構造または線形構造ポリオルガノシロキサンに含まれる全体官能基に対して全体アリール基のモル比率が30%〜60%である、請求項1に記載の硬化性組成物。
- 環状化合物の重量平均分子量が750以下である、請求項1に記載の硬化性組成物。
- 混合物は下記化学式10または下記化学式11の平均組成式を有するポリオルガノシロキサンをさらに含む、請求項4または5に記載の硬化性組成物:
[化学式10]
[RjSiO3/2]
[化学式11]
[RkRl 2SiO1/2]p[RmSiO3/2]q
上記化学式10及び11で、Rj、Rk及びRmはそれぞれ独立にエポキシ基または1価炭化水素基、Rlは炭素数1〜4のアルキル基、pは1〜3、qは1〜10である。 - 下記化学式13の平均組成式を有するポリオルガノシロキサンをさらに含む、請求項1に記載の硬化性組成物:
[化学式13]
(R11 3SiO1/2)a(R11 2SiO2/2)b(R11SiO3/2)c(SiO4/2)d
上記化学式13で、R11はそれぞれ独立にエポキシ基または1価炭化水素基、R11のうち少なくとも一つはアルケニル基、R11のうち少なくとも一つはアリール基、aは正の数、bは0または正の数、cは正の数、dは0または正の数、b/(b+c+d)は0.65未満、c/(c+d)は0.8以上である。 - 下記化学式14の化合物または下記化学式15の平均組成式を有する化合物をさらに含む、請求項1に記載の硬化性組成物:
[化学式14]
R12 3SiO(R12 2SiO)nSiR12 3
[化学式15]
(R13 3SiO1/2)a(R13 2SiO2/2)b(R13SiO3/2)c(SiO2)d
上記化学式14及び15で、R12はそれぞれ独立に水素または1価の炭化水素基、R12のうち少なくとも2個は水素原子、R12のうち少なくとも一つはアリール基、nは1〜100、R13はそれぞれ独立に水素または1価の炭化水素基、R13のうち少なくとも2個は水素原子、R13のうち少なくとも一つはアリール基、aは正の数、bは0または正の数、cは正の数、dは0または正の数である。 - 硬化した請求項1に記載の硬化性組成物で封止された光半導体。
- 請求項9に記載の光半導体をバックライトユニットに含む液晶ディスプレイ。
- 請求項9に記載の光半導体を含む照明器具。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20120082689 | 2012-07-27 | ||
KR10-2012-0082689 | 2012-07-27 | ||
KR10-2013-0089714 | 2013-07-29 | ||
KR1020130089714A KR101560044B1 (ko) | 2012-07-27 | 2013-07-29 | 경화성 조성물 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015524192A Division JP2015528046A (ja) | 2012-07-27 | 2013-07-29 | 硬化性組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017141448A JP2017141448A (ja) | 2017-08-17 |
JP6350887B2 true JP6350887B2 (ja) | 2018-07-04 |
Family
ID=50264925
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015524192A Pending JP2015528046A (ja) | 2012-07-27 | 2013-07-29 | 硬化性組成物 |
JP2017042557A Active JP6350887B2 (ja) | 2012-07-27 | 2017-03-07 | 硬化性組成物 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015524192A Pending JP2015528046A (ja) | 2012-07-27 | 2013-07-29 | 硬化性組成物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9355926B2 (ja) |
EP (1) | EP2878635B1 (ja) |
JP (2) | JP2015528046A (ja) |
KR (1) | KR101560044B1 (ja) |
CN (1) | CN104508048B (ja) |
TW (1) | TWI510554B (ja) |
WO (1) | WO2014017883A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105542706A (zh) * | 2015-12-18 | 2016-05-04 | 杭州福斯特光伏材料股份有限公司 | 一种高折射率led灯丝封装胶 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2919883A (en) * | 1958-12-11 | 1960-01-05 | Bendix Aviat Corp | Liquid damped vibration isolator |
US3983298A (en) * | 1975-04-18 | 1976-09-28 | Dow Corning Corporation | Polyorganosiloxane pressure sensitive adhesives and articles therefrom |
JPS6043872B2 (ja) * | 1979-09-29 | 1985-09-30 | 信越化学工業株式会社 | 熱硬化性オルガノポリシロキサン組成物 |
EP0797612B1 (de) * | 1994-12-12 | 1999-01-13 | Hüls Silicone Gesellschaft mit beschränkter Haftung | Verfahren zur herstellung von im wesentlichen cyclenfreien polyorgano-siloxanen und organofunktionellen siloxanen |
JP3241338B2 (ja) | 1998-01-26 | 2001-12-25 | 日亜化学工業株式会社 | 半導体発光装置 |
JP2001196151A (ja) | 2000-01-12 | 2001-07-19 | Takazono Sangyo Kk | 発熱体装置及び発熱体温度制御方法 |
JP2002226551A (ja) | 2001-01-31 | 2002-08-14 | Matsushita Electric Ind Co Ltd | 発光ダイオード |
JP3962898B2 (ja) * | 2001-12-17 | 2007-08-22 | 信越化学工業株式会社 | 線状オルガノシロキサンポリマーの製造方法 |
US7160972B2 (en) * | 2003-02-19 | 2007-01-09 | Nusil Technology Llc | Optically clear high temperature resistant silicone polymers of high refractive index |
JP4908736B2 (ja) * | 2003-10-01 | 2012-04-04 | 東レ・ダウコーニング株式会社 | 硬化性オルガノポリシロキサン組成物および半導体装置 |
JP5392805B2 (ja) * | 2005-06-28 | 2014-01-22 | 東レ・ダウコーニング株式会社 | 硬化性オルガノポリシロキサン樹脂組成物および光学部材 |
JP4684835B2 (ja) | 2005-09-30 | 2011-05-18 | 信越化学工業株式会社 | シリコーンゴム硬化物の表面タック性を低減する方法、半導体封止用液状シリコーンゴム組成物、シリコーンゴム封止型半導体装置、及び該半導体装置の製造方法 |
JP4872296B2 (ja) | 2005-09-30 | 2012-02-08 | 日亜化学工業株式会社 | シリコーンゴム封止型発光装置、及び該発光装置の製造方法 |
US8017246B2 (en) * | 2007-11-08 | 2011-09-13 | Philips Lumileds Lighting Company, Llc | Silicone resin for protecting a light transmitting surface of an optoelectronic device |
JP5972512B2 (ja) * | 2008-06-18 | 2016-08-17 | 東レ・ダウコーニング株式会社 | 硬化性オルガノポリシロキサン組成物及び半導体装置 |
JP2010013503A (ja) * | 2008-07-01 | 2010-01-21 | Showa Highpolymer Co Ltd | 硬化性樹脂組成物およびオプトデバイス |
DE102008032176A1 (de) | 2008-07-09 | 2010-01-14 | Henkel Ag & Co. Kgaa | Polymerisierbare Zusammensetzung |
JP5469874B2 (ja) * | 2008-09-05 | 2014-04-16 | 東レ・ダウコーニング株式会社 | 硬化性オルガノポリシロキサン組成物、光半導体素子封止剤および光半導体装置 |
WO2010050625A1 (en) * | 2008-10-31 | 2010-05-06 | Dow Corning Toray Co., Ltd. | Curable organopolysiloxane composition, optical semiconductor element sealant, and optical semiconductor device |
JP5499774B2 (ja) * | 2009-03-04 | 2014-05-21 | 信越化学工業株式会社 | 光半導体封止用組成物及びそれを用いた光半導体装置 |
DE102009027486A1 (de) * | 2009-07-06 | 2011-01-13 | Wacker Chemie Ag | Verfahren zur Herstellung von Siliconbeschichtungen und Siliconformkörpern aus durch Licht vernetzbaren Siliconmischungen |
CN102712812B (zh) * | 2010-01-25 | 2015-09-16 | Lg化学株式会社 | 可固化组合物 |
JP2012052035A (ja) * | 2010-09-01 | 2012-03-15 | Shin-Etsu Chemical Co Ltd | 付加硬化型シリコーン組成物、該組成物からなる光学素子封止材、及び該光学素子封止材の硬化物により光学素子が封止された半導体装置 |
JP5524017B2 (ja) * | 2010-10-08 | 2014-06-18 | 信越化学工業株式会社 | 付加硬化型シリコーン組成物、及び該組成物の硬化物により半導体素子が被覆された半導体装置 |
JP5323037B2 (ja) * | 2010-12-14 | 2013-10-23 | 積水化学工業株式会社 | 光半導体装置用封止剤及びそれを用いた光半導体装置 |
EP2662410B1 (en) * | 2011-01-06 | 2018-09-19 | LG Chem, Ltd. | Curable composition |
CN103987786B (zh) * | 2011-11-25 | 2018-06-08 | Lg化学株式会社 | 可固化组合物 |
EP2784104B1 (en) * | 2011-11-25 | 2020-06-17 | LG Chem, Ltd. | Production method of an organopolysiloxane |
JP6108132B2 (ja) * | 2012-07-27 | 2017-04-05 | エルジー・ケム・リミテッド | 硬化性組成物 |
JP6066385B2 (ja) * | 2012-07-27 | 2017-01-25 | エルジー・ケム・リミテッド | 硬化性組成物 |
JP2015524503A (ja) * | 2012-07-27 | 2015-08-24 | エルジー・ケム・リミテッド | 硬化性組成物 |
-
2013
- 2013-07-29 CN CN201380039953.2A patent/CN104508048B/zh active Active
- 2013-07-29 JP JP2015524192A patent/JP2015528046A/ja active Pending
- 2013-07-29 TW TW102127089A patent/TWI510554B/zh active
- 2013-07-29 EP EP13823114.7A patent/EP2878635B1/en active Active
- 2013-07-29 WO PCT/KR2013/006794 patent/WO2014017883A1/ko active Application Filing
- 2013-07-29 KR KR1020130089714A patent/KR101560044B1/ko active IP Right Grant
- 2013-09-18 US US14/030,562 patent/US9355926B2/en active Active
-
2017
- 2017-03-07 JP JP2017042557A patent/JP6350887B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
EP2878635A4 (en) | 2016-01-06 |
EP2878635A1 (en) | 2015-06-03 |
KR101560044B1 (ko) | 2015-10-15 |
CN104508048A (zh) | 2015-04-08 |
EP2878635B1 (en) | 2020-10-21 |
US20140031510A1 (en) | 2014-01-30 |
TWI510554B (zh) | 2015-12-01 |
CN104508048B (zh) | 2017-08-25 |
JP2015528046A (ja) | 2015-09-24 |
WO2014017883A1 (ko) | 2014-01-30 |
TW201420680A (zh) | 2014-06-01 |
US9355926B2 (en) | 2016-05-31 |
JP2017141448A (ja) | 2017-08-17 |
KR20140015216A (ko) | 2014-02-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5907262B2 (ja) | 硬化性組成物 | |
JP5850446B2 (ja) | 硬化性組成物 | |
JP6108132B2 (ja) | 硬化性組成物 | |
JP6203189B2 (ja) | 硬化性組成物 | |
JP5805883B2 (ja) | 硬化性組成物 | |
JP5871413B2 (ja) | 硬化性組成物 | |
JP2016506069A (ja) | 発光ダイオード | |
JP5885368B2 (ja) | 硬化性組成物 | |
JP6237881B2 (ja) | 硬化性組成物 | |
JP5831959B2 (ja) | 硬化性組成物 | |
JP6066385B2 (ja) | 硬化性組成物 | |
JP6237879B2 (ja) | 硬化性組成物 | |
JP6432844B2 (ja) | 硬化性組成物 | |
JP5893212B2 (ja) | 硬化性組成物 | |
JP6237880B2 (ja) | 硬化性組成物 | |
JP5987221B2 (ja) | 硬化性組成物 | |
JP6350887B2 (ja) | 硬化性組成物 | |
JP5893209B2 (ja) | 硬化性組成物 | |
KR20130058641A (ko) | 경화성 조성물 | |
JP6256780B2 (ja) | 硬化性組成物 | |
KR101591184B1 (ko) | 경화성 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20171218 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180313 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180514 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180523 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6350887 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |