WO2016031731A1 - 硬化性組成物、硬化物、硬化性組成物の使用方法、及び光デバイス - Google Patents
硬化性組成物、硬化物、硬化性組成物の使用方法、及び光デバイス Download PDFInfo
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- WO2016031731A1 WO2016031731A1 PCT/JP2015/073609 JP2015073609W WO2016031731A1 WO 2016031731 A1 WO2016031731 A1 WO 2016031731A1 JP 2015073609 W JP2015073609 W JP 2015073609W WO 2016031731 A1 WO2016031731 A1 WO 2016031731A1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229960003493 octyltriethoxysilane Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
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- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
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- 229910052714 tellurium Inorganic materials 0.000 description 1
- UGXIHAMFFYPBCW-UHFFFAOYSA-N tert-butyl 3-(dichloromethoxysilyl)propyl carbonate Chemical compound C(C)(C)(C)OC(=O)OCCC[SiH2]OC(Cl)Cl UGXIHAMFFYPBCW-UHFFFAOYSA-N 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
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- OWNXEGRCIOMNSN-UHFFFAOYSA-N tribromo(3-bromopropyl)silane Chemical compound BrCCC[Si](Br)(Br)Br OWNXEGRCIOMNSN-UHFFFAOYSA-N 0.000 description 1
- AKZFRSVAIXEQQT-UHFFFAOYSA-N tribromo(3-chloropropyl)silane Chemical compound ClCCC[Si](Br)(Br)Br AKZFRSVAIXEQQT-UHFFFAOYSA-N 0.000 description 1
- GNFASNGPRPMXAG-UHFFFAOYSA-N tribromo(3-phenylmethoxypropyl)silane Chemical compound Br[Si](Br)(Br)CCCOCC1=CC=CC=C1 GNFASNGPRPMXAG-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
- RWRKNKVDHIEKHS-UHFFFAOYSA-N tribromo(propyl)silane Chemical compound CCC[Si](Br)(Br)Br RWRKNKVDHIEKHS-UHFFFAOYSA-N 0.000 description 1
- SSZIBXDZTVQYGY-UHFFFAOYSA-N tribromo-[3-(methoxymethoxy)propyl]silane Chemical compound COCOCCC[Si](Br)(Br)Br SSZIBXDZTVQYGY-UHFFFAOYSA-N 0.000 description 1
- OOPKJVYUAXPGHS-UHFFFAOYSA-N tributoxy(3-chloropropyl)silane Chemical compound CCCCO[Si](CCCCl)(OCCCC)OCCCC OOPKJVYUAXPGHS-UHFFFAOYSA-N 0.000 description 1
- QPCISYCRQISSKN-UHFFFAOYSA-N tributoxy(3-fluoropropyl)silane Chemical compound CCCCO[Si](CCCF)(OCCCC)OCCCC QPCISYCRQISSKN-UHFFFAOYSA-N 0.000 description 1
- VPRMDTDSWWDQHO-UHFFFAOYSA-N tributoxy(3-isocyanatopropyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCN=C=O VPRMDTDSWWDQHO-UHFFFAOYSA-N 0.000 description 1
- GBXOGFTVYQSOID-UHFFFAOYSA-N trichloro(2-methylpropyl)silane Chemical compound CC(C)C[Si](Cl)(Cl)Cl GBXOGFTVYQSOID-UHFFFAOYSA-N 0.000 description 1
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 1
- OPMAXPVCTSDVDC-UHFFFAOYSA-N trichloro(3-fluoropropyl)silane Chemical compound FCCC[Si](Cl)(Cl)Cl OPMAXPVCTSDVDC-UHFFFAOYSA-N 0.000 description 1
- XXZCMCZRRPRXAM-UHFFFAOYSA-N trichloro(3-iodopropyl)silane Chemical compound Cl[Si](Cl)(Cl)CCCI XXZCMCZRRPRXAM-UHFFFAOYSA-N 0.000 description 1
- GPHYWIXZJBGHPO-UHFFFAOYSA-N trichloro(6-methylheptyl)silane Chemical compound CC(C)CCCCC[Si](Cl)(Cl)Cl GPHYWIXZJBGHPO-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
- KWDQAHIRKOXFAV-UHFFFAOYSA-N trichloro(pentyl)silane Chemical compound CCCCC[Si](Cl)(Cl)Cl KWDQAHIRKOXFAV-UHFFFAOYSA-N 0.000 description 1
- NYQDBZQWFXNBRZ-UHFFFAOYSA-N trichloro-(2-chlorophenyl)silane Chemical compound ClC1=CC=CC=C1[Si](Cl)(Cl)Cl NYQDBZQWFXNBRZ-UHFFFAOYSA-N 0.000 description 1
- QDGORAVIRGNDBW-UHFFFAOYSA-N trichloro-(2-ethoxyphenyl)silane Chemical compound CCOC1=CC=CC=C1[Si](Cl)(Cl)Cl QDGORAVIRGNDBW-UHFFFAOYSA-N 0.000 description 1
- NNWMTCDMYFZDHA-UHFFFAOYSA-N trichloro-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](Cl)(Cl)Cl)C=C1 NNWMTCDMYFZDHA-UHFFFAOYSA-N 0.000 description 1
- UXRBHEQFVKYHRG-UHFFFAOYSA-N triethoxy(3-fluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCF UXRBHEQFVKYHRG-UHFFFAOYSA-N 0.000 description 1
- PBCOGINAGIMDDC-UHFFFAOYSA-N triethoxy(3-phenylmethoxypropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1=CC=CC=C1 PBCOGINAGIMDDC-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 group CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- NNNBKZHPEASMSV-UHFFFAOYSA-N triethoxy-(2-methoxyphenyl)silane Chemical group 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
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- ZESWBFKRPIRQCD-UHFFFAOYSA-N trimethoxy-(4-methoxyphenyl)silane Chemical group COC1=CC=C([Si](OC)(OC)OC)C=C1 ZESWBFKRPIRQCD-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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
-
- 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
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/14—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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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Definitions
- the present invention relates to a curable composition capable of obtaining a cured product having excellent peel resistance and heat resistance and high adhesive strength, a cured product obtained by curing the composition, and the composition as an adhesive for optical elements. Or it is related with the method used as a sealing material for optical elements, and an optical device.
- curable compositions have been improved in various ways depending on applications, and have been widely used in industry as raw materials for optical parts and molded articles, adhesives, coating agents, and the like.
- the curable composition has attracted attention as a composition for optical element fixing materials such as an optical element adhesive and an optical element sealing material when producing an optical element sealing body.
- the optical element examples include various lasers such as a semiconductor laser (LD), light emitting elements such as a light emitting diode (LED), a light receiving element, a composite optical element, and an optical integrated circuit.
- LD semiconductor laser
- LED light emitting diode
- a composite optical element a composite optical element
- optical integrated circuit an optical integrated circuit
- the cured product of the composition for optical element fixing materials is exposed to higher energy light or higher temperature heat generated from the optical element for a long time, and deteriorates and peels off. Or a problem that the adhesive strength is reduced.
- Patent Documents 1 to 3 an optical element fixing material composition containing a polysilsesquioxane compound as a main component is disclosed in Patent Document 4, and a hydrolyzate / polycondensate of a silane compound is disclosed in Patent Document 4.
- a member for a semiconductor light emitting device to be used has been proposed.
- the cured products such as the compositions and members described in Patent Documents 1 to 4 sometimes have difficulty in obtaining peeling resistance and heat resistance while maintaining sufficient adhesive force. Therefore, development of the curable composition which is excellent in peeling resistance and heat resistance, and can obtain the hardened
- JP 2004-359933 A JP 2005-263869 A JP 2006-328231 A JP 2007-1212975 A (US2009008673A1)
- the present invention has been made in view of the situation of such prior art, and is excellent in peel resistance (delamination resistance) and heat resistance, and a curable composition from which a cured product having high adhesive strength can be obtained, It is an object to provide a cured product obtained by curing a composition, a method of using the composition as an optical element adhesive or an optical element sealing material, and an optical device.
- the present inventors As a result of intensive studies to solve the above problems, the present inventors, as described below, have a composition containing a specific silane compound (co) polymer, fine particles and a silane coupling agent in a specific ratio. The present inventors have found that the cured product has excellent peel resistance and heat resistance and has high adhesive strength, and has completed the present invention.
- the curable composition characterized by containing.
- X 0 represents a halogen atom, a cyano group, or a group represented by the formula: OG (wherein G represents a hydroxyl-protecting group), and D represents a single bond or a substituent. Or a divalent organic group having 1 to 20 carbon atoms and having no substituent.
- R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- R 2 represents an alkyl group having 1 to 20 carbon atoms or a phenyl group having or not having a substituent.
- Z 1 to Z 4 each independently represent a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom.
- m and n each independently represent a positive integer.
- o, p, q, and r each independently represent 0 or a positive integer.
- R 3 good .Z 5 also represents an alkyl group. All plurality of R 3 are different or mutually the same number of 1 to 10 carbon atoms, hydroxyl group, alkoxy having 1 to 10 carbon atoms A group or a halogen atom, s represents a positive integer, and t and u each independently represents 0 or a positive integer.
- the total amount of the component (A), the component (B), the component (C), and the component (D) is 50 to 100 based on the entire component excluding the diluent of the curable composition.
- cured material which is excellent in peeling resistance and heat resistance, and has high adhesive force can be obtained.
- the curable composition of this invention can be used when forming an optical element fixing material, and can be used especially suitably as an adhesive for optical elements and a sealing material for optical elements.
- the cured product of the present invention is excellent in peeling resistance and heat resistance and has a high adhesive force in fixing an optical element.
- the present invention will be described in detail by dividing it into 1) a curable composition, 2) a cured product, 3) a method for using the curable composition, and 4) an optical device.
- Component (A) The component (A) used in the curable composition of the present invention is a silane compound copolymer (a-1) represented by the formula (a-1) or a formula (a-2). It is a silane compound (co) polymer (a-2) represented.
- Silane compound copolymer (a-1) In the formula (a-1), X 0 represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a cyano group; or a group represented by the formula: OG. G represents a hydroxyl-protecting group. There is no restriction
- acyl protecting groups for example, acyl protecting groups; silyl protecting groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, t-butyldiphenylsilyl group; methoxymethyl group, methoxyethoxymethyl group, 1-ethoxyethyl group
- An acetal type protective group such as tetrahydropyran-2-yl group or tetrahydrofuran-2-yl group
- an alkoxycarbonyl type protective group such as t-butoxycarbonyl group
- ether-based protecting groups such as allyl group, triphenylmethyl group, benzyl group, p-methoxybenzyl group, fluorenyl group, trityl group, and benzhydryl group.
- G an acyl-type protecting group is preferable
- the acyl-based protecting group is specifically a group represented by the formula: —C ( ⁇ O) R 5 .
- R 5 is a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, isobutyl group, s- butyl, t- butyl group, n- 1 carbon atoms such as pentyl-6 Or a phenyl group having a substituent or not having a substituent.
- Examples of the substituent of the phenyl group having a substituent represented by R 5 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n -Alkyl groups such as pentyl group, n-hexyl group, n-heptyl group, n-octyl group and isooctyl group; halogen atoms such as fluorine atom, chlorine atom and bromine atom; alkoxy groups such as methoxy group and ethoxy group; Can be mentioned.
- a chlorine atom a group represented by the formula: OG ′ (wherein G ′ is an acyl group) And a group selected from a cyano group, a group selected from a chlorine atom, an acetoxy group and a cyano group is more preferable, and a cyano group is particularly preferable.
- D represents a single bond or a divalent organic group having 1 to 20 carbon atoms which has a substituent or does not have a substituent.
- the divalent organic group having 1 to 20 carbon atoms include an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, an alkynylene group having 2 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, And a divalent group having 7 to 20 carbon atoms and a combination of (an alkylene group, an alkenylene group, or an alkynylene group) and an arylene group.
- Examples of the alkylene group having 1 to 20 carbon atoms include methylene group, ethylene group, propylene group, trimethylene group, tetramethylene group, pentamethylene group and hexamethylene group.
- Examples of the alkenylene group having 2 to 20 carbon atoms include vinylene group, propenylene group, butenylene group and pentenylene group.
- Examples of the alkynylene group having 2 to 20 carbon atoms include an ethynylene group and a propynylene group.
- Examples of the arylene group having 6 to 20 carbon atoms include an o-phenylene group, an m-phenylene group, a p-phenylene group, and a 2,6-naphthylene group.
- alkylene group having 1 to 20 carbon atoms, alkenylene group having 2 to 20 carbon atoms, and alkynylene group having 2 to 20 carbon atoms may have include a halogen atom such as a fluorine atom and a chlorine atom.
- Alkoxy groups such as methoxy group and ethoxy group; alkylthio groups such as methylthio group and ethylthio group; alkoxycarbonyl groups such as methoxycarbonyl group and ethoxycarbonyl group;
- Examples of the substituent of the arylene group having 6 to 20 carbon atoms include cyano group; nitro group; halogen atom such as fluorine atom, chlorine atom and bromine atom; alkyl group such as methyl group and ethyl group; methoxy group, ethoxy group and the like An alkylthio group such as a methylthio group or an ethylthio group; These substituents may be bonded at arbitrary positions in groups such as an alkylene group, an alkenylene group, an alkynylene group, and an arylene group, and a plurality of them may be bonded in the same or different manner.
- a divalent group consisting of a combination of a substituted or non-substituted group (alkylene group, alkenylene group or alkynylene group) and a substituted or non-substituted arylene group , At least one of the above-mentioned substituents or no substituents (an alkylene group, an alkenylene group, or an alkynylene group) and at least one of the arylene groups having the above-mentioned substituents or no substituents. Examples include groups bonded in series. Specific examples include groups represented by the following formula.
- D is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 6 carbon atoms, and a methylene group or an ethylene group is preferable because a cured product having high adhesive strength can be obtained. Particularly preferred.
- R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- alkyl group having 1 to 6 carbon atoms of R 1 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and n-pentyl group. And n-hexyl group.
- R 1 is preferably a hydrogen atom.
- R 2 represents an alkyl group having 1 to 20 carbon atoms or a phenyl group having a substituent or not having a substituent.
- Examples of the alkyl group having 1 to 20 carbon atoms represented by R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n -Pentyl group, n-hexyl group, n-octyl group, isooctyl group, n-nonyl group, n-decyl group, n-dodecyl group and the like.
- Examples of the substituent of the phenyl group having a substituent of R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n- Examples thereof include alkyl groups such as pentyl group, n-hexyl group, n-heptyl group, n-octyl group and isooctyl group; alkoxy groups such as methoxy group and ethoxy group; halogen atoms such as fluorine atom and chlorine atom.
- phenyl group of R 2 having a substituent or not having a substituent include a phenyl group, a 2-chlorophenyl group, a 4-methylphenyl group, a 3-ethylphenyl group, and 2,4-dimethyl. Examples thereof include a phenyl group and a 2-methoxyphenyl group.
- R 2 is more preferably an alkyl group having 1 to 6 carbon atoms, or a phenyl group having or not having a substituent, and particularly an alkyl group having 1 to 6 carbon atoms or a phenyl group. preferable.
- Z 1 to Z 4 each independently represent a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom.
- the alkoxy group having 1 to 10 carbon atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, t-butoxy group, pentyloxy group, hexyloxy group and octyloxy group.
- the halogen atom include a chlorine atom and a bromine atom.
- Z 1 to Z 4 are preferably each independently a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms.
- M and n each independently represent a positive integer.
- o, p, q, and r each independently represent 0 or a positive integer.
- the production method of the silane compound copolymer (a-1) is not particularly limited, but is represented by the formula (1): R 1 —CH (X 0 ) —D—Si (OR 4 ) v (X 1 ) 3-v
- the silane compound (1) and the silane compound (2) represented by the formula (2): R 2 Si (OR 5 ) w (X 2 ) 3-w are preferably condensed.
- “condensation” is used in a broad concept including hydrolysis and polycondensation reactions (the same applies hereinafter).
- OR 4 or X 1 of the silane compound (1) remains in the silane compound copolymer (a-1) when the dehydration and dealcohol condensation reaction is not performed.
- OR 4 or X 1 that was not subjected to the condensation reaction, it remained as (CHR 1 X 0 -D-SiZ 1 O 2/2 ) in the formula (a-1) and was not subjected to the condensation reaction.
- OR 4 or X 1 it remains as (CHR 1 X 0 -D-SiZ 3 2 O 1/2 ) in the formula (a-1).
- silane compound (2) when OR 5 or X 2 is not subjected to dehydration and dealcohol condensation reaction, it remains in the silane compound copolymer (a-1).
- OR 5 or X 2 that has not undergone condensation reaction it remains as (R 2 SiZ 2 O 2/2 ) in formula (a-1), and OR 5 or X 2 that has not undergone condensation reaction is In the case of two, it remains as (R 2 SiZ 4 2 O 1/2 ) in the formula (a-1).
- R 1, X 0, and D are as defined above.
- R 4 represents an alkyl group having 1 to 10 carbon atoms, X 1 represents a halogen atom, and v represents an integer of 0 to 3.
- Examples of the alkyl group having 1 to 10 carbon atoms of R 4 include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, Examples thereof include an n-pentyl group and an n-hexyl group.
- Examples of the halogen atom for X 1 include a fluorine atom, a chlorine atom, and a bromine atom.
- OR 4 may be the same or different.
- (3-v) is 2 or more, X 1 may be the same or different.
- silane compound (1) examples include chloromethyltrimethoxysilane, bromomethyltriethoxysilane, 2-chloroethyltripropoxysilane, 2-bromoethyltributoxysilane, 3-chloropropyltrimethoxysilane, 3-chloro Propyltriethoxysilane, 3-chloropropyltripropoxysilane, 3-chloropropyltributoxysilane, 3-bromopropyltrimethoxysilane, 3-bromopropyltriethoxysilane, 3-bromopropyltripropoxysilane, 3-bromopropyltri Butoxysilane, 3-fluoropropyltrimethoxysilane, 3-fluoropropyltriethoxysilane, 3-fluoropropyltripropoxysilane, 3-fluoropropyltributoxysilane, 3-iodopropylto Methoxysilane, 2-chlor
- trialkoxysilane compounds are preferred as the silane compound (1) because a cured product having better adhesion can be obtained.
- Trialkoxysilane compounds having a 3-chloropropyl group, 3- Trialkoxysilane compounds having an acetoxypropyl group, trialkoxysilane compounds having a 2-cyanoethyl group, or trialkoxysilane compounds having a 3-cyanopropyl group are more preferred, trialkoxysilane compounds having a 2-cyanoethyl group Are particularly preferred.
- R 2 represents the same meaning as described above.
- R 5 represents the same alkyl group having 1 to 10 carbon atoms as R 4
- X 2 represents the same halogen atom as X 1
- w represents an integer of 0 to 3.
- the ORs 5 may be the same or different.
- (3-w) is 2 or more, X 2 may be the same or different.
- silane compound (2) examples include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-butyltriethoxysilane, i-butyltrimethoxy.
- Alkyltrialkoxysilane compounds such as silane, n-pentyltriethoxysilane, n-hexyltrimethoxysilane, i-octyltriethoxysilane, dodecyltrimethoxysilane, methyldimethoxyethoxysilane, methyldiethoxymethoxysilane;
- Alkyl halogenoalkoxysilanes such as methylchlorodimethoxysilane, methyldichloromethoxysilane, methyldichloromethoxysilane, methylchlorodiethoxysilane, ethylchlorodimethoxysilane, ethyldichloromethoxysilane, n-propylchlorodimethoxysilane, n-propyldichloromethoxysilane Compounds; Alkyltrihalogenosilane compounds such as methyltrichloros
- silane compounds (2) can be used singly or in combination of two or more.
- silane compound (2) alkyltrialkoxysilane compounds having 1 to 6 carbon atoms and phenyltrialkoxysilane compounds having a substituent or not having a substituent are preferable.
- the method for condensing the silane compound is not particularly limited, and examples thereof include a method in which the silane compound (1) and the silane compound (2) are dissolved in a solvent, a predetermined amount of catalyst is added, and the mixture is stirred at a predetermined temperature.
- the catalyst used may be either an acid catalyst or a base catalyst.
- an acid catalyst and a base catalyst can be used in combination.
- a basic catalyst may be added to the reaction solution to make it basic, and the condensation reaction may be further performed under basic conditions.
- the acid catalyst examples include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid; organic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic acid, and trifluoroacetic acid; It is done.
- inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid
- organic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, acetic acid, and trifluoroacetic acid
- Base catalysts include ammonia (water), trimethylamine, triethylamine, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, aniline, picoline, 1, Organic bases such as 4-diazabicyclo [2.2.2] octane and imidazole; quaternary ammonium salt hydroxides such as tetramethylammonium hydroxide and tetraethylammonium hydroxide; sodium methoxide, sodium ethoxide, sodium t-butoxide, Metal alkoxides such as potassium t-butoxide; metal hydrides such as sodium hydride and calcium hydride; metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; sodium carbonate, potassium carbonate and magnesium carbonate Sodium hydrogen carbonate, metal bicarbonates such as potassium bicarbonate; metal carbonates such as Siumu like
- the amount of the catalyst used is usually in the range of 0.1 mol% to 10 mol%, preferably 1 mol% to 5 mol%, based on the total molar amount of the silane compound used.
- a solvent may be used as necessary.
- the solvent to be used can be appropriately selected according to the type of the silane compound. For example, water; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate and methyl propionate; ketones such as acetone, methyl ethyl ketone, methyl i-butyl ketone and cyclohexanone And alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, i-butyl alcohol, s-butyl alcohol and t-butyl alcohol. These solvents can be used alone or in combination of two or more.
- the amount of the solvent used is such that the total molar amount of the silane compound per liter of solvent is usually 0.1 mol to 10 mol, preferably 0.5 mol to 10 mol.
- the temperature at which the silane compound is condensed (reacted) is usually in the temperature range from 0 ° C. to the boiling point of the solvent used, preferably in the range of 20 ° C. to 100 ° C. If the reaction temperature is too low, the progress of the condensation reaction may be insufficient. On the other hand, if the reaction temperature is too high, it is difficult to suppress gelation. The reaction is usually completed in 30 minutes to 20 hours.
- an acid catalyst is used, an alkaline aqueous solution such as sodium hydrogen carbonate is added to the reaction solution.
- an acid such as hydrochloric acid. Summing is carried out, and the salt produced at that time is removed by filtration or washing with water, etc., and the desired silane compound (co) polymer can be obtained.
- R 3 represents an alkyl group having 1 to 10 carbon atoms.
- the alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n- Examples include hexyl group, n-octyl group, n-nonyl group and the like.
- an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 1 to 3 carbon atoms is more preferable.
- a plurality of R 3 may be all the same or different.
- Z 5 represents a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom as in Z 1 to Z 4 .
- s represents a positive integer, and t and u each independently represent 0 or a positive integer.
- the method for producing the silane compound (co) polymer (a-2) is not particularly limited.
- a silane compound (3) represented by the formula (3): R 3 Si (OR 6 ) x (X 3 ) 3-x is converted into the same method as the method for producing the silane compound copolymer (a-1).
- the product can be produced by condensation.
- R 3 represents the same meaning as described above.
- R 6 represents the same alkyl group having 1 to 10 carbon atoms as R 4
- X 3 represents the same halogen atom as X 1
- x represents an integer of 0 to 3.
- the ORs 6 may be the same or different.
- X 3 may be the same or different.
- silane compound (3) examples include methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltripropoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, Alkyltrialkoxy such as n-propyltripropoxysilane, n-propyltributoxysilane, n-butyltrimethoxysilane, isobutyltrimethoxysilane, n-pentyltrimethoxysilane, n-hexyltrimethoxysilane, isooctyltriethoxysilane Silane compounds;
- a silane compound (3) can be used individually by 1 type or in combination of 2 or more types.
- silane compound (co) polymer (A) silane compound copolymer (a-1) or silane compound (co) polymer (a-2)
- these are random copolymers
- Any copolymer such as a block copolymer, a graft copolymer, and an alternating copolymer may be used.
- the structure of the silane compound (co) polymer (A) may be any of a ladder structure, a double-decker structure, a cage structure, a partially cleaved cage structure, a cyclic structure, and a random structure. Good.
- the mass average molecular weight (Mw) of the silane compound (co) polymer (A) is usually 800 to 30,000, preferably 1,000 to 2,500 in the case of the silane compound copolymer (a-1).
- the range is preferably from 1,200 to 2,000.
- the silane (co) compound polymer (a-2) it is usually in the range of 800 to 50,000, preferably 3,000 to 30,000, more preferably 5,000 to 15,000.
- the molecular weight distribution (Mw / Mn) of the silane compound (co) polymer (A) is not particularly limited, but in the case of the silane compound copolymer (a-1), it is usually 1.0 to 3.0, preferably 1 The range is from 1 to 2.0. In the case of the silane compound (co) polymer (a-2), it is usually in the range of 1.0 to 10.0, preferably 1.1 to 6.0. By being in the said range, the hardened
- the mass average molecular weight (Mw) and the number average molecular weight (Mn) can be determined, for example, as standard polystyrene conversion values by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent (the same applies below). .)
- the silane compound (co) polymer (A) can be used alone or in combination of two or more.
- the curable composition of this invention contains the microparticles
- the fine particles there are no particular restrictions on the fine particles, metal; metal oxide; mineral; metal carbonate such as calcium carbonate and magnesium carbonate; metal sulfate such as calcium sulfate and barium sulfate; metal hydroxide such as aluminum hydroxide; silicic acid Examples thereof include metal silicates such as aluminum, calcium silicate and magnesium silicate; silica; silicone; metal oxide whose surface is coated with silicone; inorganic fine particles such as acrylic beads; and organic fine particles such as acrylic beads.
- the metal refers to Group 1 (excluding H), Group 2 to 11, Group 12 (excluding Hg), Group 13 (excluding B), Group 14 (excluding C and Si) in the periodic table, An element belonging to Group 15 (excluding N, P, As and Sb) or Group 16 (excluding O, S, Se, Te and Po).
- the silica may be any of dry silica, wet silica, and organically modified silica, and may be a mixture of two or more of these.
- metal oxide examples include titanium oxide, alumina, boehmite, chromium oxide, nickel oxide, copper oxide, titanium oxide, zirconium oxide, indium oxide, zinc oxide, and composite oxides thereof.
- the metal oxide fine particles include sol particles composed of these metal oxides.
- Examples of minerals include smectite and bentonite.
- Examples of the smectite include montmorillonite, beidellite, hectorite, saponite, stevensite, nontronite, and soconite.
- silica, silicone, metal oxide, or metal oxide fine particles whose surface is coated with silicone is preferable, and silica, silicone, or Further, fine particles of metal oxide whose surface is coated with silicone are more preferable, and fine particles of titanium oxide or aluminum oxide whose surface is coated with silicone are particularly preferable.
- the shape of the fine particles may be any of spherical, chain-like, needle-like, plate-like, piece-like, rod-like, and fiber-like, but is preferably spherical.
- the spherical shape means a substantially spherical shape including a polyhedron shape that can be approximated to a spherical shape, a spheroidal shape, an oval shape, a confetti shape, an eyebrow shape, and the like.
- the average primary particle diameter of the fine particles is more than 0.04 ⁇ m and not more than 8 ⁇ m. When it is larger than 0.04 ⁇ m, the effect of adding fine particles can be obtained.
- the dispersibility of the curable composition obtained as it is 8 micrometers or less becomes a favorable thing.
- the average primary particle size is preferably 0.06 to 7 ⁇ m, more preferably 0.3 to 6 ⁇ m, and particularly preferably 1 to 4 ⁇ m from the viewpoint of achieving both peel resistance and dispersibility.
- the average primary particle size is determined by measuring the particle size distribution by the laser scattering method using a laser diffraction / scattering particle size distribution measuring device (for example, product name “LA-920” manufactured by Horiba, Ltd.). Two or more kinds of these fine particles may be used in combination.
- the amount of component (B) used is usually such that the proportion of component (A) and component (B) used is the mass ratio of component (A) to component (B) (component (A): component (B)).
- the amount is from 100: 0.3 to 100: 20, preferably from 100: 0.5 to 100: 15, and more preferably from 100: 0.8 to 100: 12.
- the amount of the component (B) used is less than the above range, it is difficult to obtain the intended peeling resistance effect, and when it is more than the above range, the adhesive strength decreases, which is not preferable.
- the curable composition of this invention contains the silane coupling agent which has a nitrogen atom in a molecule
- numerator deoxysilylator
- the silane coupling agent (C) is not particularly limited as long as it has a nitrogen atom in the molecule.
- Examples thereof include trialkoxysilane compounds represented by the following formula (c-1), dialkoxyalkylsilane compounds represented by the formula (c-2), dialkoxyarylsilane compounds, and the like.
- R a represents an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, or a t-butoxy group.
- the plurality of R a may be all the same or different.
- R b represents an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, or a t-butyl group; or a phenyl group, a 4-chlorophenyl group, a 4- An aryl group having a substituent or not having a substituent, such as a methylphenyl group;
- R c represents a C 1-10 organic group having a nitrogen atom. R c may further be bonded to a group containing another silicon atom. Specific examples of the organic group having 1 to 10 carbon atoms of R c include N-2- (aminoethyl) -3-aminopropyl group, 3-aminopropyl group, N- (1,3-dimethyl-butylidene) amino. Examples thereof include a propyl group, 3-ureidopropyltriethoxysilane, N-phenyl-aminopropyl group and the like.
- the compound in the case where R c is an organic group bonded to another group containing a silicon atom includes an isocyanurate skeleton. And an isocyanurate-based silane coupling agent bonded to another silicon atom, and an urea-based silane coupling agent bonded to another silicon atom via a urea skeleton.
- silane coupling agent (C) an isocyanurate-based silane coupling agent and a urea-based silane coupling agent are preferable from the viewpoint of obtaining a cured product having higher adhesive force.
- those having 4 or more alkoxy groups bonded to silicon atoms are preferred. Having 4 or more alkoxy groups bonded to silicon atoms means that the total count of alkoxy groups bonded to the same silicon atom and alkoxy groups bonded to different silicon atoms is 4 or more.
- a compound represented by the following formula (c-3) is a urea-based silane cup having 4 or more alkoxy groups bonded to silicon atoms.
- the ring agent include compounds represented by the following formula (c-4).
- t1 to t5 each independently represents an integer of 1 to 10, preferably an integer of 1 to 6, and particularly preferably 3.
- Specific examples of the compound represented by the formula (c-3) include 1,3,5-N-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3,5, -N-tris (3- Triethoxysilylpropyl) isocyanurate, 1,3,5, -N-tris (3-trii-propoxysilylpropyl) isocyanurate, 1,3,5, -N-tris (3-tributoxysilylpropyl) isocyanate 1,3,5-N-tris [(tri (C1-6) alkoxy) silyl (C1-10) alkyl] isocyanurate such as nurate; 1,3,5, -N-tris (3-ditoxymethylsilylpropyl) isocyanurate, 1,3,5, -N-tris (3-dimethoxyethylsilylpropyl) isocyanurate, 1,3,5,- N-tris (3-dimethoxy i-propylsilylpropyl) isocyan
- Specific examples of the compound represented by the formula (c-4) include N, N′-bis (3-trimethoxysilylpropyl) urea, N, N′-bis (3-triethoxysilylpropyl) urea, N N, N′-bis (3-tripropoxysilylpropyl) urea, N, N′-bis (3-tributoxysilylpropyl) urea, N, N′-bis (2-trimethoxysilylethyl) urea, N′-bis [(tri (C1-6) alkoxysilyl) (C1-10) alkyl] urea; N, N′-bis (3-dimethoxymethylsilylpropyl) urea, N, N′-bis (3-dimethoxyethylsilylpropyl) urea, N, N′-bis (3-diethoxymethylsilylpropyl) urea, etc.
- the component (C) of the present invention includes 1,3,5-N-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3,5-N-tris (3-triethoxysilylpropyl).
- Isocyanurate hereinafter referred to as “isocyanurate compound”
- N, N′-bis (3-trimethoxysilylpropyl) urea N, N′-bis (3-triethoxysilylpropyl) urea
- the use ratio of both is preferably 100: 1 to 100: 200 in terms of the mass ratio of (isocyanurate compound) and (urea compound).
- the isocyanurate compound is used alone or in combination with the urea compound.
- the component (A) and the component (C) are mixed at a mass ratio of the component (A) to the component (C) (component (A): component (C)) 100: 0. It is preferably contained in a ratio of 3 to 100: 40, more preferably in a ratio of 100: 1 to 100: 30, and further preferably in a ratio of 100: 3 to 100: 25.
- a ratio of 3 to 100: 40 it is possible to obtain a curable composition from which a cured product having excellent heat resistance and high adhesive strength can be obtained.
- silane coupling agent (D) Component
- silane coupling agent (D) a silane coupling agent having an acid anhydride structure in the molecule
- the silane coupling agent (D) is an organosilicon compound having both a group (Q) having an acid anhydride structure and a hydrolyzable group (R e ) in one molecule. Specifically, it is a compound represented by the following formula (d).
- Q represents an acid anhydride structure
- R d represents an alkyl group having 1 to 6 carbon atoms, or a phenyl group having or not having a substituent
- R e having 1 to 6 represents an alkoxy group or a halogen atom
- i and k represent an integer of 1 to 3
- j represents an integer of 0 to 2
- i + j + k 4.
- R d may be the same or different.
- k is 2 or 3
- among a plurality of R e may be different from each be the same.
- i is 2 or 3
- the plurality of Qs may all be the same or different.
- Q is the following formula
- examples of the alkoxy group having 1 to 6 carbon atoms represented by R e include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, and a t-butoxy group.
- examples of the halogen atom include a chlorine atom and a bromine atom.
- Examples of the alkyl group having 1 to 6 carbon atoms of R d include the same groups as those exemplified as the alkyl group having 1 to 6 carbon atoms represented by R 1. Examples of the phenyl group that does not include the same groups as those exemplified for R 2 above. Among these, as the compound represented by the formula (d), the following formula (d-1)
- h is preferably 2 to 8, more preferably 2 or 3, and particularly preferably 3.
- silane coupling agent represented by the formula (d-1) examples include 2- (trimethoxysilyl) ethyl succinic anhydride, 2- (triethoxysilyl) ethyl succinic anhydride, 3- (trimethoxy Tri (carbon number 1-6) alkoxysilyl (carbon number 2-8) alkyl succinic anhydride, such as silyl) propyl succinic anhydride, 3- (triethoxysilyl) propyl succinic anhydride; Di (C 1-6) alkoxymethylsilyl (C 2-8) alkyl succinic anhydride, such as 2- (dimethoxymethylsilyl) ethyl succinic anhydride; (C1-C6) alkoxydimethylsilyl (C2-C8) alkyl succinic anhydride, such as 2- (methoxydimethylsilyl) ethyl succinic anhydride;
- Trihalogenosilyl (2 to 8 carbon atoms) alkyl succinic anhydride such as 2- (trichlorosilyl) ethyl succinic anhydride, 2- (tribromosilyl) ethyl succinic anhydride; Dihalogenomethylsilyl (2-8 carbon atoms) alkyl succinic anhydride, such as 2- (dichloromethylsilyl) ethyl succinic anhydride; And halogenodimethylsilyl (having 2 to 8 carbon atoms) alkyl succinic anhydride such as 2- (chlorodimethylsilyl) ethyl succinic anhydride.
- a component can be used individually by 1 type or in combination of 2 or more types.
- the component (A) and the component (D) are mixed at a mass ratio of the component (A) to the component (D) (component (A): component (D)) 100: 0. It is preferably contained in a ratio of 01 to 100: 30, more preferably in a ratio of 100: 0.1 to 100: 10.
- the cured product of the curable composition of the present invention has excellent heat resistance, adhesiveness, and peel resistance.
- the curable composition of the present invention preferably further contains a diluent for the purpose of imparting fluidity.
- a diluent for example, diethylene glycol monobutyl ether acetate, glycerin diglycidyl ether, butanediol diglycidyl ether, diglycidyl aniline, neopentyl glycol glycidyl ether, cyclohexane dimethanol diglycidyl ether, alkylene diglycidyl ether, polyglycol diglycidyl ether Polypropylene glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, 4-vinylcyclohexene monooxide, vinylcyclohexene dioxide, methylated vinylcyclohexene dioxide, and the like.
- diluents can be used alone or in combination of two or more.
- the amount of the diluent used is preferably 50 to 100% by mass, more preferably 60 to 90% by mass, and 70 to 85% by mass of the solid content of the curable composition of the present invention. Is more preferable.
- the total amount of (A) component, (B) component, (C) component, and (D) component is the diluent of a curable composition.
- the content is preferably 50 to 100% by mass, more preferably 60 to 100% by mass, based on the total components removed.
- the total amount of the component (A), the component (B), the component (C), and the component (D) is within the above range, so that the curable composition of the present invention is more excellent in heat resistance and adhesiveness. It will be a thing.
- the curable composition of the present invention may further contain other components in addition to the above components as long as the object of the present invention is not impaired.
- other components include an antioxidant, an ultraviolet absorber, and a light stabilizer.
- An antioxidant is added to prevent oxidative degradation during heating.
- examples of the antioxidant include phosphorus antioxidants, phenolic antioxidants, sulfur antioxidants and the like.
- Examples of phosphorus antioxidants include phosphites and oxaphosphaphenanthrene oxides.
- phenolic antioxidants include monophenols, bisphenols, and high-molecular phenols.
- sulfur-based antioxidant include dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, and the like.
- antioxidants can be used singly or in combination of two or more.
- the usage-amount of antioxidant is 10 mass% or less normally with respect to (A) component.
- the ultraviolet absorber is added for the purpose of improving the light resistance of the resulting cured product.
- examples of the ultraviolet absorber include salicylic acids, benzophenones, benzotriazoles, hindered amines and the like.
- An ultraviolet absorber can be used individually by 1 type or in combination of 2 or more types.
- the usage-amount of a ultraviolet absorber is 10 mass% or less normally with respect to (A) component.
- the light stabilizer is added for the purpose of improving the light resistance of the resulting cured product.
- the light stabilizer include poly [ ⁇ 6- (1,1,3,3, -tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl ⁇ ⁇ (2,2,6 , 6-tetramethyl-4-piperidine) imino ⁇ hexamethylene ⁇ (2,2,6,6-tetramethyl-4-piperidine) imino ⁇ ] and the like.
- These light stabilizers can be used alone or in combination of two or more.
- the total amount of these other components (excluding the diluent) is usually 20% by mass or less based on the component (A).
- the curable composition of the present invention is prepared by, for example, blending the components (A) to (D) and, if necessary, a diluent and other components in a predetermined ratio, and mixing and defoaming by a known method. Obtainable.
- the curable composition of the present invention obtained as described above, a cured product having excellent peel resistance and heat resistance and high adhesive strength can be obtained. Therefore, the curable composition of the present invention is suitably used as a raw material for optical parts and molded articles, an adhesive, a coating agent, and the like. In particular, since the problem relating to deterioration of the optical element fixing material accompanying the increase in luminance of the optical element can be solved, the curable composition of the present invention can be suitably used as an optical element fixing composition. .
- the second of the present invention is a cured product obtained by curing the curable composition of the present invention.
- Heat curing is mentioned as a method of hardening the curable composition of this invention.
- the heating temperature for curing is usually 100 to 200 ° C., and the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
- cured material of this invention has high adhesive force, and is excellent in peeling resistance and heat resistance. Therefore, the hardened
- the cured product obtained by heating the curable composition of the present invention is excellent in peel resistance.
- the sapphire chip is pressure-bonded and cured by heat treatment at 170 ° C. for 2 hours, and then the sealing material is poured into the cup and heated at 150 ° C. for 1 hour. Process to obtain a cured specimen.
- This test piece was exposed to an environment of 85 ° C. and 85% RH for 168 hours, then pre-heated at 160 ° C. and treated by IR reflow with a maximum temperature of 260 ° C. for 1 minute, and then a heat cycle tester The test is allowed to stand at ⁇ 40 ° C. and + 100 ° C.
- the sealing material is removed, and it is examined whether or not the elements are peeled off together.
- the probability of peeling is usually 45% or less, more preferably 25% or less.
- the cured product obtained by curing the curable composition of the present invention has a high adhesive force, for example, by measuring the adhesive force as follows. That is, the curable composition is applied to the mirror surface of the silicon chip, and the coated surface is placed on the adherend and pressure-bonded, and then heated and cured. This is left for 30 seconds on a measurement stage of a bond tester that has been heated to a predetermined temperature (for example, 23 ° C., 100 ° C.) in advance, and in a horizontal direction (shearing) with respect to the adhesion surface from a position 50 ⁇ m high from the adherend. Direction) and measure the adhesive force between the test piece and the adherend.
- a predetermined temperature for example, 23 ° C., 100 ° C.
- the adhesive strength of the cured product is preferably 60 N / 2 mm ⁇ or more at 23 ° C., more preferably 80 N / 2 mm ⁇ or more, and particularly preferably 100 N / 2 mm ⁇ or more.
- the adhesive strength of the cured product is preferably 40 N / 2 mm ⁇ or more at 100 ° C., more preferably 50 N / 2 mm ⁇ or more, and particularly preferably 60 N / 2 mm ⁇ or more.
- the third aspect of the present invention is a method of using the curable composition of the present invention as a composition for an optical element fixing material such as an optical element adhesive or an optical element sealing material. It is.
- optical elements include light emitting elements such as LEDs and LDs, light receiving elements, composite optical elements, and optical integrated circuits.
- the curable composition of this invention can be used conveniently as an adhesive agent for optical elements.
- the composition is applied to one or both adhesive surfaces of a material to be bonded (such as an optical element and its substrate), followed by pressure bonding. Then, the method of making it heat-cure and adhere
- Main substrate materials for bonding optical elements include glass such as soda lime glass and heat-resistant hard glass; ceramics; iron, copper, aluminum, gold, silver, platinum, chromium, titanium, and alloys of these metals , Metals such as stainless steel (SUS302, SUS304, SUS304L, SUS309, etc.); polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ethylene-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetheretherketone , Synthetic resins such as polyethersulfone, polyphenylene sulfide, polyetherimide, polyimide, polyamide, acrylic resin, norbornene resin, cycloolefin resin, glass epoxy resin, etc. .
- the heating temperature at the time of heat curing is usually 100 to 200 ° C. although it depends on the curable composition used.
- the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
- the curable composition of this invention can be used suitably as a sealing material of an optical element sealing body.
- the composition is molded into a desired shape to obtain a molded body containing the optical element, and then heated.
- cure are mentioned.
- the method for molding the curable composition of the present invention into a desired shape is not particularly limited, and a known molding method such as a normal transfer molding method or a casting method can be employed.
- the heating temperature at the time of heat curing is usually 100 to 200 ° C. although it depends on the curable composition used.
- the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
- the obtained optical element encapsulant uses the curable composition of the present invention, it has excellent peel resistance and heat resistance, and has high adhesive strength.
- the 4th of this invention is an optical device which uses the curable composition of this invention as an adhesive agent for optical element fixing materials, or a sealing material for optical element fixing materials.
- the optical device of the present invention is obtained by mounting the optical element on a support substrate using the curable composition of the present invention as an adhesive or sealing material for fixing the optical element. For this reason, the optical element is fixed with a high adhesive force and has excellent durability.
- optical elements include light emitting elements such as LEDs and LDs, light receiving elements, composite optical elements, and optical integrated circuits.
- the mass average molecular weight (Mw) and number average molecular weight (Mn) of the silane compound (co) polymer obtained in the following production examples were standard polystyrene equivalent values, and measured with the following apparatus and conditions.
- the reaction solution was concentrated to 50 ml with an evaporator, 100 ml of ethyl acetate was added to the concentrate, and neutralized with a saturated aqueous sodium hydrogen carbonate solution. After leaving still for a while, the organic layer was fractionated. Next, the organic layer was washed twice with distilled water and then dried over anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated to 50 ml with an evaporator, and the resulting concentrate was dropped into a large amount of n-hexane to precipitate, and the precipitate was separated by decantation.
- the obtained precipitate was dissolved in methyl ethyl ketone (MEK) and collected, and the solvent was distilled off under reduced pressure using an evaporator. The residue was vacuum dried to obtain 13.5 g of a silane compound copolymer (A1).
- MEK methyl ethyl ketone
- the silane compound copolymer (A1) had a weight average molecular weight (Mw) of 1,870 and a molecular weight distribution (Mw / Mn) of 1.42.
- IR spectrum data of the silane compound copolymer (A1) are shown below. Si—Ph: 698 cm ⁇ 1 , 740 cm ⁇ 1 , Si—O: 1132 cm ⁇ 1 , —CN: 2259 cm ⁇ 1
- Example 1 To 100 parts (parts by mass, the same shall apply hereinafter) of the silane compound copolymer (A1) obtained in Production Example 1, As the component (B), 1 part of a silicone filler having an average primary particle size of 0.5 ⁇ m (manufactured by Nikko Spain Corporation, MSP-SN05), As component (C), 10 parts of 1,3,5-N-tris [3- (trimethoxysilyl) propyl] isocyanurate, As component (D), 1 part of 3- (trimethoxysilyl) propyl succinic anhydride, and Diethylene glycol monobutyl ether acetate was added so that the solid concentration would be 80%, and the entire volume was thoroughly mixed and defoamed to obtain curable composition 1.
- a silicone filler having an average primary particle size of 0.5 ⁇ m manufactured by Nikko Spain Corporation, MSP-SN05
- As component (C) 10 parts of 1,3,5-N-tris [3- (trimethoxysilyl)
- Example 1 Comparative Examples 1 to 13
- the type of silane compound (co) polymer as component (A) the type of component (B), the amount used (parts), the amount used (parts) of component (C), the amount of components (D)
- the curable compositions 2 to 33 of Examples 2 to 33 and the curable properties of Comparative Examples 1 to 13 were the same as Example 1 except that the amount used (parts) was changed as described in Table 1 below. Compositions 1r to 13r were obtained.
- types of component (B): B1 to B9 represent the following.
- Each of the curable compositions 1 to 33 and 1r to 13r is applied to a mirror surface of a 2 mm square silicon chip so that the thickness is about 2 ⁇ m, and the coated surface is placed on an adherend (silver plated copper plate). Placed and crimped. Then, it heated and hardened at 170 degreeC for 2 hours, and the adherend with a test piece was obtained. The obtained adherend with a test piece was left on a measurement stage of a bond tester (series 4000, manufactured by Daisy) heated in advance to a predetermined temperature (23 ° C., 100 ° C.) for 30 seconds, and 50 ⁇ m from the adherend.
- a bond tester series 4000, manufactured by Daisy
- the LED lead frame (product name: 5050 D / G PKG LEADFRAME manufactured by Enomoto Co., Ltd.) is coated with curable compositions 1-33, 1r-13r about 0.4 mm ⁇ , and then a 0.5 mm square sapphire chip is applied. Crimped. Then, after being cured by heat treatment at 170 ° C. for 2 hours, a sealing material (manufactured by Shin-Etsu Chemical Co., Ltd., product name: EG6301) was poured into the cup and heated at 150 ° C. for 1 hour to obtain a test piece. . This test piece is exposed to an environment of 85 ° C.
- the cured products of the curable compositions of Comparative Examples 1 to 13 often have an adhesive strength of 70 N / 2 mm ⁇ or less, and in particular at 100 ° C., all except for Comparative Examples 6 and 7 are from 45 N / 2 mm ⁇ . It was low and inferior in adhesive strength. In addition, except for Comparative Example 5, the evaluation of peel resistance was low. Although the curable composition of Comparative Example 5 had a peel resistance evaluation of B, the adhesive strength at 100 ° C. was 18.85 N / 2 mm ⁇ , and the adhesive strength and heat resistance were poor.
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Abstract
Description
また、硬化性組成物は、光素子封止体を製造する際に、光素子用接着剤や光素子用封止材等の光素子固定材用組成物としても注目を浴びてきている。
しかしながら、特許文献1~4に記載された組成物や部材等の硬化物であっても、十分な接着力を保ちつつ、耐剥離性、耐熱性を得るのは困難な場合があった。
従って、耐剥離性及び耐熱性に優れ、かつ、高い接着力を有する硬化物が得られる硬化性組成物の開発が切望されている。
(A)下記式(a-1)
下記式(a-2)
で示されるシラン化合物(共)重合体
(B)平均一次粒子径が0.04μm超、8μm以下の微粒子
(C)分子内に窒素原子を有するシランカップリング剤
(D)分子内に酸無水物構造を有するシランカップリング剤
〔3〕前記(B)成分が、シリコーンで表面が被覆された酸化チタン又は酸化アルミニウムの微粒子である〔1〕に記載の硬化性組成物。
〔4〕前記(A)成分の質量平均分子量が800~30,000である、〔1〕に記載の硬化性組成物。
〔5〕前記(A)成分が、式(a-1)中、(m+o+q)と(n+p+r)とが、(m+o+q):(n+p+r)=5:95~60:40の割合の化合物である、〔1〕に記載の硬化性組成物。
〔7〕前記(A)成分と、(B)成分と、(C)成分と、(D)成分の合計量が、硬化性組成物の希釈剤を除いた成分全体に対して、50~100質量%であることを特徴とする、〔1〕に記載の硬化性組成物。
〔8〕前記硬化性組成物の固形分濃度が、50~100質量%であることを特徴とする、〔6〕に記載の硬化性組成物。
〔9〕光素子固定材用組成物である〔1〕に記載の硬化性組成物。
〔11〕光素子固定材である〔10〕に記載の硬化物。
〔13〕前記〔1〕に記載の硬化性組成物を、光素子固定材用封止材として使用する方法。
〔14〕前記〔1〕に記載の硬化性組成物を、光素子固定材用接着剤又は光素子固定材用封止材として用いてなる光デバイス。
本発明の硬化性組成物は、光素子固定材を形成する際に使用することができ、特に、光素子用接着剤、及び光素子用封止材として好適に使用することができる。
本発明の硬化物は、光素子固定において、耐剥離性及び耐熱性に優れ、かつ、高い接着力を有する。
本発明の硬化性組成物は、下記(A)~(D)成分を有する硬化性組成物であって、(A)成分と(B)成分とを、(A)成分と(B)成分の質量比で、〔(A)成分:(B)成分〕=100:0.3~100:20の割合で含有することを特徴とする。
(A)下記式(a-1)又は、下記式(a-2)で示されるシラン化合物(共)重合体
(C)分子内に窒素原子を有するシランカップリング剤
(D)分子内に酸無水物構造を有するシランカップリング剤
本発明の硬化性組成物に用いる(A)成分は、前記式(a-1)で表されるシラン化合物共重合体(a-1)、又は、式(a-2)で表されるシラン化合物(共)重合体(a-2)である。
前記式(a-1)中、X0は、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;シアノ基;又は式:OGで表される基;を表す。
G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、t-ブチルジメチルシリル基、t-ブチルジフェニルシリル基等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-イル基等のアセタール系の保護基;t-ブトキシカルボニル基等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、Gとしては、アシル系の保護基が好ましい。
炭素数1~20の2価の有機基としては、炭素数1~20のアルキレン基、炭素数2~20のアルケニレン基、炭素数2~20のアルキニレン基、炭素数6~20のアリーレン基、(アルキレン基、アルケニレン基、又はアルキニレン基)とアリーレン基との組み合わせからなる炭素数7~20の2価の基等が挙げられる。
炭素数2~20のアルケニレン基としては、ビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基等が挙げられる。
炭素数2~20のアルキニレン基としては、エチニレン基、プロピニレン基等が挙げられる。
炭素数6~20のアリーレン基としては、o-フェニレン基、m-フェニレン基、p-フェニレン基、2,6-ナフチレン基等が挙げられる。
これらの置換基は、アルキレン基、アルケニレン基、アルキニレン基及びアリーレン基等の基において任意の位置に結合していてよく、同一若しくは相異なって複数個が結合していてもよい。
これらの中でも、R1としては水素原子が好ましい。
R2で表される炭素数1~20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、s-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-オクチル基、イソオクチル基、n-ノニル基、n-デシル基、n-ドデシル基等が挙げられる。
これらの中でも、Z1~Z4はそれぞれ独立して、ヒドロキシル基又は炭素数1~6のアルコキシ基が好ましい。
シラン化合物(2)についても同様に、OR5又はX2が、脱水及び脱アルコール縮合反応されなかった場合は、シラン化合物共重合体(a-1)に残存する。縮合反応されなかったOR5又はX2が1つだった場合は、式(a-1)において(R2SiZ2O2/2)として残存し、縮合反応されなかったOR5又はX2が2つだった場合は、式(a-1)において(R2SiZ4 2O1/2)として残存する。
前記式(1)中、R1、X0、及びDは、前記と同じ意味を表す。R4は炭素数1~10のアルキル基を表し、X1はハロゲン原子を表し、vは0~3の整数を表す。
X1のハロゲン原子としては、フッ素原子、塩素原子、及び臭素原子等が挙げられる。
vが2以上のとき、OR4同士は同一であっても相異なっていてもよい。また、(3-v)が2以上のとき、X1同士は同一であっても相異なっていてもよい。
2-クロロエチルジクロロメトキシシラン、2-ブロモエチルジクロロエトキシシラン、3-クロロプロピルジクロロメトキシシラン、3-フルオロプロピルジクロロメトキシシラン、3-クロロプロピルジクロロエトキシシラン、3-クロロプロピルクロロジエトキシシラン、3-ブロモプロピルジクロロエトキシシラン等の、X0がハロゲン原子であるジハロゲノアルコキシシラン化合物類;
クロロメチルトリクロロシラン、
3-ブロモプロピルトリブロモシラン、3-ブロモプロピルトリクロロシラン、3-フルオロプロピルトリクロロシラン、3-クロロプロピルトリクロロシラン、3-クロロプロピルトリブロモシラン、3-アイオドプロピルトリクロロシラン、等の、X0がハロゲン原子であるトリハロゲノシラン化合物類;
これらのシラン化合物(1)は一種単独で、或いは二種以上を組み合わせて用いることができる。
前記式(2)中、R2は前記と同じ意味を表す。R5は前記R4と同様の炭素数1~10のアルキル基を表し、X2は前記X1と同様のハロゲン原子を表し、wは0~3の整数を表す。
wが2以上のとき、OR5同士は同一であっても相異なっていてもよい。また、(3-w)が2以上のとき、X2同士は同一であっても相異なっていてもよい。
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、メチルジクロロメトキシシラン、メチルクロロジエトキシシラン、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、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ハロゲノアルコキシシラン化合物類;
メチルトリクロロシラン、メチルトリブロモシラン、エチルトリクロロシラン、エチルトリブロモシラン、n-プロピルトリクロロシラン等のアルキルトリハロゲノシラン化合物類;
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、フェニルクロロメトキシエトキシシラン、フェニルクロロジエトキシシラン、フェニルジクロロエトキシシラン等の、置換基を有する、又は置換基を有さないフェニルハロゲノアルコキシシラン化合物類;
フェニルトリクロロシラン、フェニルトリブロモシラン、4-メトキシ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-エトキシフェニルトリクロロシラン、2-クロロフェニルトリクロロシラン等の、置換基を有する、又は置換基を有さないフェニルトリハロゲノシラン化合物;が挙げられる。
これらのシラン化合物(2)は一種単独で、或いは二種以上を組み合わせて用いることができる。
これらの中でも、シラン化合物(2)としては、炭素数1~6のアルキルトリアルコキシシラン化合物類、置換基を有する、又は置換基を有さないフェニルトリアルコキシシラン化合物類が好ましい。
また、酸触媒と塩基触媒を組み合わせて用いることもできる。例えば、酸触媒の存在下、シラン化合物の縮合反応を行った後に、反応液に塩基触媒を添加して塩基性とし、塩基性条件下に、さらに縮合反応を行ってもよい。
前記式(a-2)中、R3は炭素数1~10のアルキル基を表す。炭素数1~10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、イソブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-オクチル基、n-ノニル基等が挙げられる。これらの中でも、炭素数1~6のアルキル基が好ましく、炭素数1~3のアルキル基がより好ましい。複数のR3はすべて同一であっても相異なっていてもよい。
Z5は、前記Z1~Z4と同様の、ヒドロキシル基、炭素数1~10のアルコキシ基、又は、ハロゲン原子を示す。
sは正の整数を示し、t、uはそれぞれ独立して、0又は正の整数を示す。
式(3)中、R3は前記と同じ意味を表す。R6は、前記R4と同様の、炭素数1~10のアルキル基を表し、X3は前記X1と同様のハロゲン原子を表し、xは0~3の整数を表す。
xが2以上のとき、OR6同士は同一であっても相異なっていてもよい。また、(3-x)が2以上のとき、X3同士は同一であっても相異なっていてもよい。
シラン化合物(3)は一種単独で、或いは二種以上を組み合わせて用いることができる。
質量平均分子量(Mw)および数平均分子量(Mn)は、例えば、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求めることができる(以下にて同じである。)。
本発明の硬化性組成物は、(B)成分として、平均一次粒子径が0.04μm超、8μm以下の微粒子を含む。
微粒子としては、特に制限はなく、金属;金属酸化物;鉱物;炭酸カルシウム、炭酸マグネシウム等の金属炭酸塩;硫酸カルシウム、硫酸バリウム等の金属硫酸塩;水酸化アルミニウム等の金属水酸化物;珪酸アルミニウム、珪酸カルシウム、珪酸マグネシウム等の金属珪酸塩;シリカ;シリコーン;シリコーンで表面が被覆された金属酸化物;等の無機微粒子;アクリルビーズ等の有機微粒子;等が挙げられる。
スメクタイトとしては、例えば、モンモリロナイト、バイデライト、ヘクトライト、サポナイト、スチブンサイト、ノントロナイト、ソーコナイト等が挙げられる。
平均一次粒子径としては、耐剥離性と分散性を両立させる観点から、0.06~7μmがより好ましく、0.3~6μmがさらに好ましく、1~4μmが特に好ましい。
平均一次粒子径は、レーザー回折・散乱式粒度分布測定装置(例えば堀場製作所社製、製品名「LA-920」)等を用いて、レーザー散乱法による粒度分布の測定を行うことにより求められる。
これらの微粒子は2種類以上を併用してもよい。
本発明の硬化性組成物は、(C)成分として、分子内に窒素原子を有するシランカップリング剤(以下、「シランカップリング剤(C)」ということがある。)を含む。
Rb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、t-ブチル基等の炭素数1~6のアルキル基;又は、フェニル基、4-クロロフェニル基、4-メチルフェニル基等の、置換基を有する、又は置換基を有さないアリール基;を表す。
Rcの炭素数1~10の有機基の具体例としては、N-2-(アミノエチル)-3-アミノプロピル基、3-アミノプロピル基、N-(1,3-ジメチル-ブチリデン)アミノプロピル基、3-ウレイドプロピルトリエトキシシラン、N-フェニル-アミノプロピル基等が挙げられる。
ケイ素原子に結合したアルコキシ基を4以上有するとは、同一のケイ素原子に結合したアルコキシ基と、異なるケイ素原子に結合したアルコキシ基との総合計数が4以上という意味である。
t1~t5はそれぞれ独立して、1~10の整数を表し、1~6の整数であるのが好ましく、3であるのが特に好ましい。
1,3,5,-N-トリス(3-ジトキシメチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジメトキシエチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジメトキシi-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジメトキシn-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジメトキシフェニルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジエトキシメチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジエトキシエチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジエトキシi-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジエトキシn-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジエトキシフェニルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジi-プロポキシメチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジi-プロポキシエチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジi-プロポキシi-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジi-プロポキシn-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジi-プロポキシフェニルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジブトキシメチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジブトキシエチルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジブトキシi-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジブトキシn-プロピルシリルプロピル)イソシアヌレート、1,3,5,-N-トリス(3-ジブトキシフェニルシリルプロピル)イソシアヌレート等の1,3,5-N-トリス〔(ジ(炭素数1~6)アルコキシ)シリル(炭素数1~10)アルキル〕イソシアヌレート;等が挙げられる。
N,N’-ビス(3-ジメトキシメチルシリルプロピル)ウレア、N,N’-ビス(3-ジメトキシエチルシリルプロピル)ウレア、N,N’-ビス(3-ジエトキシメチルシリルプロピル)ウレア等のN,N’-ビス〔(ジ(炭素数1~6)アルコキシ(炭素数1~6)アルキルシリル(炭素数1~10)アルキル)ウレア;
N,N’-ビス(3-ジメトキシフェニルシリルプロピル)ウレア、N,N’-ビス(3-ジエトキシフェニルシリルプロピル)ウレア等のN,N’-ビス〔(ジ(炭素数1~6)アルコキシ(炭素数6~20)アリールシリル(炭素数1~10)アルキル)ウレア;等が挙げられる。
これらの中でも、本発明の(C)成分としては、1,3,5-N-トリス(3-トリメトキシシリルプロピル)イソシアヌレート、1,3,5-N-トリス(3-トリエトキシシリルプロピル)イソシアヌレート(以下、「イソシアヌレート化合物」という。)、N,N’-ビス(3-トリメトキシシリルプロピル)ウレア、N,N’-ビス(3-トリエトキシシリルプロピル)ウレア(以下、「ウレア化合物」という。)、及び、前記イソシアヌレート化合物とウレア化合物との組み合わせを用いるのが好ましい。
また、ウレア化合物の使用割合は、前記(A)成分100質量部に対して、20質量部以下であるのが好ましく、15質量部以下であるのがより好ましい。ウレア化合物単独で用いる場合も、イソシアヌレート化合物と併用して用いる場合においても同様である。
このような割合で(A)成分及び(C)成分を用いることにより、耐熱性に優れ、高い接着力を有する硬化物が得られる硬化性組成物を得ることができる。
本発明の硬化性組成物は、(D)成分として、分子内に酸無水物構造を有するシランカップリング剤(以下、「シランカップリング剤(D)」ということがある。)を含む。
Qとしては、下記式
式(d)中、Reの炭素数1~6のアルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、t-ブトキシ基等が挙げられる。
ハロゲン原子としては、塩素原子、臭素原子等が挙げられる。
なかでも、式(d)で表される化合物としては、下記式(d-1)
で表される化合物が好ましい。式中、hは2~8であるのが好ましく、2又は3であるのがより好ましく、3であるのが特に好ましい。
2-(ジメトキシメチルシリル)エチル無水コハク酸等の、ジ(炭素数1~6)アルコキシメチルシリル(炭素数2~8)アルキル無水コハク酸;
2-(メトキシジメチルシリル)エチル無水コハク酸等の、(炭素数1~6)アルコキシジメチルシリル(炭素数2~8)アルキル無水コハク酸;
2-(ジクロロメチルシリル)エチル無水コハク酸等の、ジハロゲノメチルシリル(炭素数2~8)アルキル無水コハク酸;
2-(クロロジメチルシリル)エチル無水コハク酸等の、ハロゲノジメチルシリル(炭素数2~8)アルキル無水コハク酸;等が挙げられる。
(D)成分は一種単独で、或いは二種以上を組み合わせて用いることができる。
このような割合で(A)成分及び(D)成分を用いることにより、本発明の硬化性組成物の硬化物は、耐熱性、接着性、かつ、耐剥離性に優れるものとなる。
希釈剤としては、例えば、ジエチレングリコールモノブチルエーテルアセテート、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。
これらの希釈剤は一種単独で、或いは二種以上を組み合わせて用いることができる。
希釈剤の使用量は、本発明の硬化性組成物の固形分濃度を50~100質量%とするのが好ましく、60~90質量%とするのがより好ましく、70~85質量%とするのがさらに好ましい。
他の成分としては、酸化防止剤、紫外線吸収剤、光安定剤等が挙げられる。
紫外線吸収剤としては、サリチル酸類、ベンゾフェノン類、ベンゾトリアゾール類、ヒンダードアミン類等が挙げられる。
紫外線吸収剤は一種単独で、或いは二種以上を組み合わせて用いることができる。
紫外線吸収剤の使用量は、(A)成分に対して、通常、10質量%以下である。
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等が挙げられる。
これらの光安定剤は一種単独で、或いは二種以上を組み合わせて用いることができる。
これらの他の成分(希釈剤を除く)の総使用量は、(A)成分に対して、通常、20質量%以下である。
したがって、本発明の硬化性組成物は、光学部品や成形体の原料、接着剤、コーティング剤等として好適に使用される。特に、光素子の高輝度化に伴う、光素子固定材の劣化に関する問題を解決することができることから、本発明の硬化性組成物は、光素子固定用組成物として好適に使用することができる。
本発明の第2は、本発明の硬化性組成物を硬化してなる硬化物である。
本発明の硬化性組成物を硬化する方法としては加熱硬化が挙げられる。硬化するときの加熱温度は、通常、100~200℃であり、加熱時間は、通常10分から20時間、好ましくは30分から10時間である。
したがって、本発明の硬化物は、光素子の高輝度化に伴う劣化に関する問題を解決し、光素子固定材として好適に使用することができる。例えば、光学部品や成形体の原料、接着剤、コーティング剤等として好適に使用される。
LEDリードフレームに、硬化性組成物を塗布した上に、サファイアチップを圧着し、170℃で2時間加熱処理して硬化させた後、封止材をカップ内に流し込み、150℃で1時間加熱処理して硬化物の試験片を得る。この試験片を85℃、85%RHの環境に168時間曝したのち、プレヒート160℃で、最高温度が260℃になる加熱時間1分間のIRリフローにて処理を行い、次いで、熱サイクル試験機にて、-40℃及び+100℃で各30分放置する試験を1サイクルとして、300サイクル実施する。その後、封止材を除去し、その際に素子が一緒に剥がれるか否かを調べる。本発明の硬化物においては、剥離する確率は通常45%以下、より好ましくは25%以下である。
硬化物の接着力は、23℃において60N/2mm□以上であることが好ましく、80N/2mm□以上であることがより好ましく、100N/2mm□以上であることが特に好ましい。また硬化物の接着力は、100℃において40N/2mm□以上であることが好ましく、50N/2mm□以上であることがより好ましく、60N/2mm□以上であることが特に好ましい。
本発明の第3は、本発明の硬化性組成物を、光素子用接着剤又は光素子用封止材等の光素子固定材用組成物として使用する方法である。
光素子としては、LED、LD等の発光素子、受光素子、複合光素子、光集積回路等が挙げられる。
本発明の硬化性組成物は、光素子用接着剤として好適に使用することができる。
本発明の硬化性組成物を光素子用接着剤として使用する方法としては、接着の対象とする材料(光素子とその基板等)の一方又は両方の接着面に該組成物を塗布し、圧着した後、加熱硬化させ、接着の対象とする材料同士を強固に接着させる方法が挙げられる。
本発明の硬化性組成物は、光素子封止体の封止材として好適に用いることができる。
本発明の硬化性組成物を光素子用封止材として使用する方法としては、例えば、該組成物を所望の形状に成形して、光素子を内包した成形体を得た後、そのものを加熱硬化させることにより光素子封止体を製造する方法等が挙げられる。
本発明の硬化性組成物を所望の形状に成形する方法としては、特に限定されるものではなく、通常のトランスファー成形法や、注型法等の公知のモールド法を採用できる。
本発明の第4は、本発明の硬化性組成物を、光素子固定材用接着剤又は光素子固定材用封止材として用いてなる光デバイスである。
本発明の光デバイスは、本発明の硬化性組成物を、光素子固定用の接着剤又は封止材として用い、光素子を支持体基板上に実装して得られるものである。そのため、光素子が高い接着力で固定された、耐久性に優れたものとなっている。
光素子としては、LED、LD等の発光素子、受光素子、複合光素子、光集積回路等が挙げられる。
下記製造例で得たシラン化合物(共)重合体の質量平均分子量(Mw)及び数平均分子量(Mn)は、標準ポリスチレン換算値とし、以下の装置及び条件にて測定した。
装置名:HLC-8220GPC、東ソー社製
カラム:TSKgelGMHXL、TSKgelGMHXL、及び、TSKgel2000HXLを順次連結したもの
溶媒:テトラヒドロフラン
注入量:80μl
測定温度:40℃
流速:1ml/分
検出器:示差屈折計
製造例で得たシラン化合物(共)重合体のIRスペクトルは、フーリエ変換赤外分光光度計(Spectrum100、パーキンエルマー社製)を使用して測定した。
300ml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、以下にて同じ)20.2g(102mmol)と、2-シアノエチルトリメトキシシラン(アヅマックス社製、以下にて同じ)3.15g(18mmol)、並びに、溶媒として、アセトン96ml及び蒸留水24mlを仕込んだ後、内容物を攪拌しながら、触媒としてリン酸(関東化学社製、以下にて同じ)0.15g(1.5mmol)を加え、25℃でさらに16時間攪拌を継続した。
シラン化合物共重合体(A1)のIRスペクトルデータを以下に示す。
Si-Ph:698cm-1,740cm-1,Si-O:1132cm-1,-CN:2259cm-1
300mlのナス型フラスコに、メチルトリエトキシシラン(信越化学工業社製、製品名:KBE-13)71.37g(400mmol)を仕込んだ後、蒸留水21.6mlに35%塩酸0.10g(シラン化合物の合計量に対して0.25mol%)を溶解した水溶液を撹拌しながら加え、全容を30℃にて2時間、次いで70℃に昇温して5時間撹拌したのち、酢酸プロピルを140g入れ撹拌した。ここに、28%アンモニア水0.12g(シラン化合物の合計量に対して0.5mol%)を撹拌しながら加え、全容を70℃に昇温して3時間さらに撹拌した。反応液に精製水を加え、分液し、水層のpHが7になるまでこの操作を繰り返した。有機層をエバポレーターで濃縮し、濃縮物を真空乾燥することにより、シラン化合物重合体(A2)を55.7g得た。このものの質量平均分子量(MW)は7800、分子量分布(PDI)は4.52であった。
シラン化合物重合体(A2)のIRスペクトルデータを以下に示す。
Si-CH3:1272cm-1,1409cm-1,Si-O:1132cm-1
製造例1で得たシラン化合物共重合体(A1)100部(質量部、以下同じ)に、
(B)成分として、平均一次粒子径が0.5μmのシリコーンフィラー(日興リカ社製、MSP-SN05)1部、
(C)成分として、1,3,5-N-トリス〔3-(トリメトキシシリル)プロピル〕イソシアヌレート10部、
(D)成分として、3-(トリメトキシシリル)プロピルコハク酸無水物1部、及び、
固形分濃度が80%になるようにジエチレングリコールモノブチルエーテルアセテートを添加し、全容を十分に混合、脱泡することにより硬化性組成物1を得た。
実施例1において、(A)成分としてのシラン化合物(共)重合体の種類、(B)成分の種類、使用量(部)、(C)成分の使用量(部)、(D)成分の使用量(部)を、下記表1に記載した通りに変更した以外は、実施例1と同様にして、実施例2~33の硬化性組成物2~33、比較例1~13の硬化性組成物1r~13rを得た。
下記表中、(B)成分の種類:B1~B9は以下を表す。
・B2:シリコーン系微粒子(平均一次粒子径:0.8μm)、日興リカ社製、MSP-SN08
・B3:シリコーン系微粒子(平均一次粒子径:2μm)、モメンティブ・パフォーマンス・マテ・リアルズ・ジャパン合同会社製、トスパール120
・B4:シリコーン系微粒子(平均一次粒子径:4.5μm)、モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製、トスパール145
・B5:シリコーンで表面を被覆された酸化アルミニウム(平均一次粒子径:6μm)、日興リカ社製、MSP-AK06
・B6:シリコーンで表面を被覆された酸化チタン(平均一次粒子径:4μm)、日興リカ社製、MSP-TK04
・B7:シリコーンで表面を被覆された酸化チタン(平均一次粒子径:4μm)、日興リカ社製、MSP-TS04
・B8:シリコーン系微粒子(平均一次粒子径:5μm)、日興リカ社製、MSP-3500
・B9:シリカ系微粒子(平均一次粒子径:0.07μm)、トクヤマ社製、シルフィル NSS-5N
測定結果及び評価を下記表1に示す。
2mm角のシリコンチップのミラー面に、硬化性組成物1~33、1r~13rのそれぞれを、厚さが約2μmになるよう塗布し、塗布面を被着体(銀メッキ銅板)の上に載せ圧着した。その後、170℃で2時間加熱して硬化させて試験片付被着体を得た。得られた試験片付被着体を、予め所定温度(23℃、100℃)に加熱したボンドテスター(シリーズ4000、デイジ社製)の測定ステージ上に30秒間放置し、被着体から50μmの高さの位置より、スピード200μm/sで接着面に対し水平方法(せん断方向)に応力をかけ、23℃及び100℃における、試験片と被着体との接着強度(N/2mm□)を測定した。
LEDリードフレーム(エノモト社製、製品名:5050 D/G PKG LEADFRAME)に、硬化性組成物1~33、1r~13rを、0.4mmφ程度塗布した上に、0.5mm角のサファイアチップを圧着した。その後、170℃で2時間加熱処理して硬化させた後、封止材(信越化学工業社製、製品名:EG6301)をカップ内に流し込み、150℃で1時間加熱して試験片を得た。
この試験片を85℃、85%RHの環境に168時間曝したのち、プレヒート160℃で、最高温度が260℃になる加熱時間1分間のIRリフロー(リフロー炉:相模理工社製、製品名「WL-15-20DNX型」)にて処理を行った。その後、熱サイクル試験機にて、-40℃及び+100℃で各30分放置する試験を1サイクルとして、300サイクル実施した。その後、封止材を除去する操作を行い、その際に素子が一緒に剥がれるか否かを調べた。この試験を、各硬化性組成物につきそれぞれ12回行った。
下記表1に、素子が一緒に剥がれた回数を数え、剥離発生率が25%以下であれば「A」、25%より大きく50%以下であれば「B」、50%より大きければ「C」と評価した。
一方、比較例1~13の硬化性組成物の硬化物は、接着強度が70N/2mm□以下のものが多く、特に、100℃においては、比較例6,7以外はすべて45N/2mm□より低く、接着強度に劣るものであった。また、比較例5以外は、すべて耐剥離性の評価は低いものであった。比較例5の硬化性組成物は、耐剥離性の評価はBであったものの、100℃における接着強度が18.85N/2mm□と、接着力、耐熱性に劣っていた。
Claims (14)
- 下記(A)~(D)成分を有する硬化性組成物であって、(A)成分と(B)成分とを、(A)成分と(B)成分の質量比で、〔(A)成分:(B)成分〕=100:0.3~100:20の割合で含有することを特徴とする硬化性組成物。
(A)下記式(a-1)
下記式(a-2)
で示されるシラン化合物(共)重合体
(B)平均一次粒子径が0.04μm超、8μm以下の微粒子
(C)分子内に窒素原子を有するシランカップリング剤
(D)分子内に酸無水物構造を有するシランカップリング剤 - 前記(B)成分が、シリカ、シリコーン、及びシリコーンで表面が被覆された金属酸化物、から選ばれる少なくとも1種の微粒子である請求項1に記載の硬化性組成物。
- 前記(B)成分が、シリコーンで表面が被覆された酸化チタン又は酸化アルミニウムの微粒子である請求項1に記載の硬化性組成物。
- 前記(A)成分の質量平均分子量が800~30,000である、請求項1に記載の硬化性組成物。
- 前記(A)成分が、前記式(a-1)中、(m+o+q)と(n+p+r)とが、(m+o+q):(n+p+r)=5:95~60:40の割合の化合物である、請求項1に記載の硬化性組成物。
- さらに、希釈剤を含有する請求項1に記載の硬化性組成物。
- 前記(A)成分と、(B)成分と、(C)成分と、(D)成分の合計量が、硬化性組成物の希釈剤を除いた成分全体に対して、50~100質量%であることを特徴とする、請求項1に記載の硬化性組成物。
- 前記硬化性組成物の固形分濃度が、50~100質量%であることを特徴とする、請求項1に記載の硬化性組成物。
- 光素子固定材用組成物である請求項1に記載の硬化性組成物。
- 請求1に記載の硬化性組成物を硬化してなる硬化物。
- 光素子固定材である請求項10に記載の硬化物。
- 請求項1に記載の硬化性組成物を、光素子固定材用接着剤として使用する方法。
- 請求項1に記載の硬化性組成物を、光素子固定材用封止材として使用する方法。
- 請求項1に記載の硬化性組成物を、光素子固定材用接着剤又は光素子固定材用封止材として用いてなる光デバイス。
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JP2017122216A (ja) | 2017-07-13 |
KR102354544B1 (ko) | 2022-01-21 |
US10266734B2 (en) | 2019-04-23 |
US20170275513A1 (en) | 2017-09-28 |
JP6064094B2 (ja) | 2017-01-18 |
EP3187547B1 (en) | 2018-12-05 |
EP3187547A1 (en) | 2017-07-05 |
TWI696662B (zh) | 2020-06-21 |
EP3187547A4 (en) | 2018-04-25 |
CN106574116B (zh) | 2020-07-14 |
CN106574116A (zh) | 2017-04-19 |
TW201612247A (en) | 2016-04-01 |
MY179602A (en) | 2020-11-11 |
JPWO2016031731A1 (ja) | 2017-04-27 |
KR20170046648A (ko) | 2017-05-02 |
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