JP6307465B2 - 縮合硬化型シリコーン組成物および半導体装置 - Google Patents
縮合硬化型シリコーン組成物および半導体装置 Download PDFInfo
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- JP6307465B2 JP6307465B2 JP2015060906A JP2015060906A JP6307465B2 JP 6307465 B2 JP6307465 B2 JP 6307465B2 JP 2015060906 A JP2015060906 A JP 2015060906A JP 2015060906 A JP2015060906 A JP 2015060906A JP 6307465 B2 JP6307465 B2 JP 6307465B2
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- 239000003085 diluting agent Substances 0.000 description 1
- GHDURCSNTWOYKH-UHFFFAOYSA-N dimethoxy-(2,3,4,5,6-pentafluorophenyl)silane Chemical compound FC1=C(C(=C(C(=C1[SiH](OC)OC)F)F)F)F GHDURCSNTWOYKH-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- RRZRBCXJMZVTAF-UHFFFAOYSA-N dimethoxy-phenyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](OC)(OC)C1=CC=CC=C1 RRZRBCXJMZVTAF-UHFFFAOYSA-N 0.000 description 1
- DYPVADKXJPHQCY-UHFFFAOYSA-N dimethoxymethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound COC(OC)[SiH2]CCCOCC1CO1 DYPVADKXJPHQCY-UHFFFAOYSA-N 0.000 description 1
- CLVPEDBHXVFIHB-UHFFFAOYSA-N dimethoxysilyloxy-methyl-diphenylsilane Chemical compound C1(=CC=CC=C1)[Si](O[SiH](OC)OC)(C)C1=CC=CC=C1 CLVPEDBHXVFIHB-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical class C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000006355 external stress Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910021505 gold(III) hydroxide Inorganic materials 0.000 description 1
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical compound O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- PFEAZKFNWPIFCV-UHFFFAOYSA-N hydroxy-[hydroxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(O)O[Si](C)(C)O PFEAZKFNWPIFCV-UHFFFAOYSA-N 0.000 description 1
- IGUXCTSQIGAGSV-UHFFFAOYSA-K indium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[In+3] IGUXCTSQIGAGSV-UHFFFAOYSA-K 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910021514 lead(II) hydroxide Inorganic materials 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XKINWJBZPLWKCW-UHFFFAOYSA-N methoxy-[methoxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound CO[Si](C)(C)O[Si](C)(C)OC XKINWJBZPLWKCW-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 1
- 229910021508 nickel(II) hydroxide Inorganic materials 0.000 description 1
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WKMKTIVRRLOHAJ-UHFFFAOYSA-N oxygen(2-);thallium(1+) Chemical compound [O-2].[Tl+].[Tl+] WKMKTIVRRLOHAJ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 150000004980 phosphorus peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- UJPWWRPNIRRCPJ-UHFFFAOYSA-L strontium;dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Sr+2] UJPWWRPNIRRCPJ-UHFFFAOYSA-L 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910003438 thallium oxide Inorganic materials 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-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
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- 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
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Silicon Polymers (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Led Device Packages (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
Description
(A)下記式(1−1)または(1−2)で示される分岐状オルガノポリシロキサン
(B)下記式(2)で表され、網状構造を有するオルガノポリシロキサン、
該オルガノポリシロキサンの量は(A)成分100質量部に対して5〜900質量部である、及び
(C)縮合触媒 触媒量。
さらに本発明は該シリコーン組成物の硬化物を備えた半導体装置を提供する。
(A)分岐状ポリオルガノシロキサン
本発明の組成物は、下記式(1−1)または(1−2)で表される、シロキサン単位数1〜4個からなる分岐鎖を有する分岐状オルガノポリシロキサンを含有することを特徴とする。
上記分岐状オルガノポリシロキサンは、下記式(3)で示される片末端ケイ素原子に二つの加水分解性基が結合したオルガノシロキサンを分岐鎖導入のための原料とし、該オルガノシロキサンを縮合反応させることを特徴とする製造方法により得られる。該縮合反応は触媒存在下で行われるのが好ましい。
本発明の組成物はさらに、網目構造を有するオルガノポリシロキサンを含有することができる。該オルガノポリシロキサンは下記式(2)で表される。
(C)縮合触媒は、上記(A)成分及び任意で(B)成分の縮合反応を進行させるものであれば特に限定されず、従来公知のものであってよい。該縮合触媒としては、例えば、スズ、鉛、アンチモン、鉄、カドミウム、バリウム、マンガン、亜鉛、クロム、コバルト、ニッケル、アルミニウム、マグネシウム、ハフニウム、ガリウム又はゲルマニウム及びジルコニウムなどの金属を含む縮合触媒が挙げられる。これらの金属はアルコキシ化、エステル化、キレート化されていて良い。例えば、ジブチルスズジオクトエート、ジブチルスズジアセテート、ジブチルスズジマレエート、ジブチルスズジラウレート、及びブチルスズ2−エチルヘキソエートなどのアルキルスズエステル化合物等の有機スズ金属触媒、及び、鉄、コバルト、マンガン、鉛、及び亜鉛の2−エチルへキソエート、及びアルミニウムビスエチルアセトアセテート・モノアセチルアセトネート等のアルミキレートが挙げられる。
蛍光体は、特に制限されるものでなく、従来公知の蛍光体を使用すればよい。例えば、半導体素子、特に窒化物系半導体を発光層とする半導体発光ダイオードからの光を吸収し、異なる波長の光に波長変換するものであることが好ましい。このような蛍光体としては、例えば、Eu、Ce等のランタノイド系元素で主に賦活される窒化物系蛍光体・酸窒化物系蛍光体、Eu等のランタノイド系、Mn等の遷移金属系の元素により主に賦活されるアルカリ土類金属ハロゲンアパタイト蛍光体、アルカリ土類金属ホウ酸ハロゲン蛍光体、アルカリ土類金属アルミン酸塩蛍光体、アルカリ土類金属ケイ酸塩蛍光体、アルカリ土類金属硫化物蛍光体、アルカリ土類金属チオガレート蛍光体、アルカリ土類金属窒化ケイ素蛍光体、ゲルマン酸塩蛍光体、又は、Ce等のランタノイド系元素で主に賦活される希土類アルミン酸塩蛍光体、希土類ケイ酸塩蛍光体又はEu等のランタノイド系元素で主に賦活される有機及び有機錯体蛍光体、Ca−Al−Si−O−N系オキシ窒化物ガラス蛍光体等から選ばれる1種以上であることが好ましい。
無機充填材としては、例えば、シリカ、ヒュームドシリカ、ヒュームド二酸化チタン、アルミナ、炭酸カルシウム、ケイ酸カルシウム、二酸化チタン、酸化第二鉄、及び酸化亜鉛等を挙げることができる。これらは、1種単独でまたは2種以上を併せて使用することができる。無機充填材の配合量は特に制限されないが、(A)成分及び(B)成分の合計100質量部あたり20質量部以下、好ましくは0.1〜10質量部の範囲で適宜配合すればよい。
本発明のシリコーン組成物は、接着性を付与するため、必要に応じて接着助剤を含有してよい。接着助剤としては、例えば、一分子中にケイ素原子に結合した水素原子、アルケニル基、アルコキシ基、エポキシ基から選ばれる官能性基を少なくとも2種、好ましくは3種有するオルガノシロキサンオリゴマーが挙げられる。該オルガノシロキサンオリゴマーは、ケイ素原子数4〜50個であることが好ましく、より好ましくは4〜20個である。また、接着助剤として、下記一般式(7)で示されるオルガノオキシシリル変性イソシアヌレート化合物、及びその加水分解縮合物(オルガノシロキサン変性イソシアヌレート化合物)を使用することができる。
[その他の添加剤]
本発明のシリコーン組成物には、上記成分のほかに、その他の添加剤を配合することができる。その他の添加剤としては、例えば、老化防止剤、ラジカル禁止剤、難燃剤、界面活性剤、オゾン劣化防止剤、光安定剤、増粘剤、可塑剤、酸化防止剤、熱安定剤、導電性付与剤、帯電防止剤、放射線遮断剤、核剤、リン系過酸化物分解剤、滑剤、顔料、金属不活性化剤、物性調整剤、有機溶剤等が挙げられる。これらの任意成分は、一種を単独で用いても二種以上を併用してもよい。
[GPC測定条件]
展開溶媒:テトラヒドロフラン
流速:0.6mL/min
カラム:TSK Guardcolumn SuperH−L
TSKgel SuperH4000(6.0mmI.D.×15cm×1)
TSKgel SuperH3000(6.0mmI.D.×15cm×1)
TSKgel SuperH2000(6.0mmI.D.×15cm×2)
(いずれも東ソー社製)
カラム温度:40℃
試料注入量:20μL (試料濃度:0.5wt%−テトラヒドロフラン溶液)
検出器:示差屈折率計(RI)
1,1−ジフェニル−1,3−ジメチル−3,3−ジメトキシジシロキサン63.7g(0.2mol)、ポリメチルフェニルシロキサン−ω,ω−ジオール(Mw=537.43)1198.5g(2.23mol)を攪拌し、60℃に調節した。その後、Sr(OH)2・8H2Oを2.0g加え、3時間反応を行った。得られた生成物から、濾過により触媒を除去し、メタノールと水を減圧留去することで、下記式で表されオイル状の分岐状オルガノポリシロキサンを得た。Mw=6,332であった。29Si−NMRスペクトルから、下記式においてnは平均42であり、mは平均1.3であった。
1,1,3,3−テトラフェニル−1,5−ジメチル−5,5−ジメトキシトリシロキサン524.1g(1mol)とポリメチルフェニルシロキサン−ω,ω−ジオール(Mw=537.43)1381.2g(2.57mol)を混合し、攪拌しながら80℃に調節した。その後、Sr(OH)2・8H2Oを12g加え、発生するメタノールを留去しながら80℃で12時間反応を行った。得られた生成物から、濾過により触媒を除去し、メタノールと水を減圧留去することで、下記式で表されるオイル状の分岐状オルガノポリシロキサンを得た。Mw=10,416であった。29Si−NMRから、下記式においてnは平均54であり、mは平均5.8であった。
1,1−ジフェニル−1,3−ジメチル−3,3−ジメトキシジシロキサン955.5g(3mol)に水142.6gを加え、攪拌しながらSr(OH)2・8H2Oを12g加えた。その後、発生するメタノールを留去しながら80℃で12時間反応を行った。得られた生成物から水とメタノールを留去し、濾過により触媒を除去することで、下記式で表されオイル状である分岐状オルガノポリシロキサンを得た。Mw=4302であった。29Si−NMRから、下記式においてmは平均15であった。
1,1−ジフェニル−1,3−ジメチル−3,3−ジメトキシジシロキサン63.7g(0.2mol)、ポリメチルフェニルシロキサン−ω,ω−ジオール(Mw=537.43)1198.5g(2.23mol)を攪拌し、80℃に調節した。その後、Sr(OH)2・8H2Oを4.0g加え、メタノールを留去しながら3時間反応を行った。得られた生成物にテトラメトキシシラン152.2g(1.0mol)を加え、続けて12時間反応を行った。濾過により触媒を除去し、メタノールと水、未反応のテトラメトキシシランを減圧留去することで、下記式で表されオイル状である分岐状オルガノポリシロキサンを得た。Mw=7,844であった。29Si−NMRスペクトルから、下記式においてnは平均50であり、mは平均1.6であった。
1,1−ジフェニル−1,3−ジメチル−3,3−ジメトキシジシロキサン127.4g(0.4mol)とポリジメチルシロキサン−ω,ω−ジオール(Mw=1498)749.0g(0.5mol)を混合し、攪拌しながら80℃に調節した。その後、Sr(OH)2・8H2Oを12g加え、発生するメタノールを留去しながら80℃で12時間反応を行った。得られた生成物から、濾過により触媒を除去し、メタノールと水を減圧留去することで下記分岐状シリコーンオイルを合成した。Mw=10,129であった。29Si−NMRから、nは平均116であり、mは平均4.7であった。
1,1,1,3−テトラメチル−3,3−ジメトキシジシロキサン 194.4g(1mol)とポリジメチルシロキサン−ω,ω−ジオール(Mw=1498)749.0g(0.5mol)を混合し、攪拌しながら80℃に調節した。その後、Sr(OH)2・8H2Oを12g加え、発生するメタノールを留去しながら80℃で12時間反応を行った。得られた生成物から、濾過により触媒を除去し、メタノールと水を減圧留去することで、下記式で表され、オイル状である分岐状オルガノポリシロキサンを得た。Mw=21,008であった。29Si−NMRから、下記式においてnは平均230であり、mは平均26であった。
オクタメチルシクロテトラシロキサン1483g(5mol)とトリメトキシシラン272.5g(2mol)、水酸化カリウム8.9g水119gを加え、80℃で8時間、発生するメタノールを留去しながら反応を行った。次いで、混合物をオートクレープに移し、140℃密閉系で12時間反応を行った後、80℃まで冷却し、酢酸10.1gで中和した。その後、水洗と減圧留去を行うことで、下記式で表されるオイル状の分岐状オルガノポリシロキサンを得た。Mw=17,657であった。29Si−NMRから、下記式においてn及びn’は各々平均108であり、mは平均19であった。
(A’−8)下記式で表される直鎖状オルガノポリシロキサン(信越化学工業株式会社製)
(A’−10)下記式で表される直鎖状オルガノポリシロキサン(信越化学工業株式会社製)
(B−1)下記式で表される、M単位とT単位で構成されたメチルフェニル系シリコーンレジン(信越化学工業株式会社製、SiOH量=1.5wt%、SiOCH3量=3.0wt%、50wt%キシレン溶液)
(R5 3SiO1/2)r(R6SiO3/2)t(OR7)w
式中、R5はメチル基であり、R6はフェニル基であり、R7は水素原子またはメチル基であり、重量平均分子量は3505であり、r/(r+t)=0.25であり、t/(r+t)=0.75である。
wはSiOH及びSiOCH3の合計量が4.5wt%となる値である。
(B−2)下記式で表される、M単位とQ単位で構成されたメチル系シリコーンレジン(信越化学工業株式会社製、SiOH量=1.2wt%、60wt%トルエン溶液)
(R5 3SiO1/2)r(SiO4/2)u(OH)w
式中、R5はメチル基であり、重量平均分子量は6082であり、r/(r+u)=0.43であり、u/(r+u)=0.57である。wはSiOH量が1.2wt%となる値である。
(C)縮合触媒:アルミキレートD(アルミニウムビスエチルアセトアセテート・モノアセチルアセトネート、川研ファインケミカル株式会社製)
(A−1)成分を100質量部と(B−1)成分を固形分として250質量部混合した後、溶媒を減圧留去した。その後、混合物を室温付近まで十分に冷却し、(C)縮合触媒を(A−1)成分及び(B−1)成分の合計100質量部に対して0.1質量部となる量で加えて混合し、シリコーン組成物を調製した。
各成分の組成及び配合量を表1に記載の通り変更した他は実施例1を繰返し、シリコーン組成物を得た。全ての組成物において(C)縮合触媒の量はオルガノポリシロキサン及びシリコーンレジンの合計100質量部に対して0.1質量部である。
50mm径×10mm厚のアルミシャーレに調製したシリコーン組成物を流し込み、60℃×1時間、100℃×1時間、150℃×12時間の順でステップキュアして硬化物を得た。得られた硬化物の硬さ(デュロメータTypeAもしくはTypeD)をJIS K 6253−3:2012に記載の方法に準拠して測定した。結果を表1及び2に記載する。
50mm×20mm×1mm厚のスライドガラス2枚の間に凹型の1mm厚テフロンスペーサーを挟み、それらを固定した後、シリコーン組成物を流し込み、60℃×1時間、100℃×1時間、150℃×12時間の順でステップキュアしてサンプルを作製した。得られたサンプルの450nmにおける光透過率を分光光度計 U−4100(株式会社日立ハイテクノロジーズ製)にて測定した。結果を表1及び2に記載する。
上記(2)で作製した硬化物に、温度調節機能付きレーザー照射装置(光源:日亜化学株式会社製UV−LED、オーブン:ESPEC STH−120、検出器:ADVANTEST R8240)を用いて、120℃にて440nmのレーザー光(出力:250mW/mm2)を1,000時間照射した。初期(0時間)の440nmにおける透過率を100%として、レーザーを1,000時間照射した後の透過率を表1及び表2に記載する。
150mm×200mm×2mm厚の凹型テフロン金型にシリコーン組成物を流し込み、60℃×1時間、100℃×1時間、さらに150℃×12時間の順でステップキュアして作製した硬化物の貯蔵弾性率(MPa)を、DMA Q800(TAインスツルメント株式会社製)により、−140℃〜150℃の範囲で測定し、得られた貯蔵弾性率の値から導き出されるTanδの値をプロットしたグラフから得られるピークトップの温度をガラス転移温度:Tgとした。測定条件は、20mm長×5mm幅×1mm厚のサンプル、昇温速度5℃/min、マルチ周波数モード、引っ張りモード、振幅15μmで行った。結果を表1及び2に記載する。
Tiger3528パッケージ(信越化学株式会社製)にシリコーン組成物をディスペンスし、60℃×1時間、100℃×1時間、150℃×12時間の順でステップキュアし、硬化物でパッケージを封止した試験体を製造した。該試験体の20個について、−50℃〜140℃、1000回のサーマルサイクル試験(TCT)を行い、封止物にクラックが生じた試験体の数を計測した。結果を表1及び2に記載する。
実施例1および実施例6、比較例1の樹脂組成物を150mm×200mm×2mm厚の凹型テフロン金型にそれぞれ流し込み、60℃×1時間、100℃×1時間、150℃×12時間の順でステップキュアして、各々の試験サンプルを作製した。得られたサンプルをJIS K 7129に準拠して、Lyssy法(装置名L80−5000、Lyssy社製)により水蒸気透過率を測定した。各硬化物の水蒸気透過率は以下の通りであった。
実施例1:16g・m2/day
実施例6:51g・m2/day
比較例1:16g・m2/dayであった。
実施例1及び比較例1の組成物に含まれる(A)成分及び(B)成分は共に芳香族基を有する。一方、実施例6の組成物に含まれる(A)成分及び(B)成分はいずれも芳香族基を有さない。上記結果に示す通り、より低いガス透過性を有する硬化物を得るためには(A)成分及び(B)成分が芳香族基を有する方が好ましい。
Claims (9)
- 下記(A)成分、(B)成分及び(C)成分を含む縮合硬化型シリコーン組成物
(A)下記式(1−1)または(1−2)で示される分岐状オルガノポリシロキサン
(B)下記式(2)で表され、網状構造を有するオルガノポリシロキサン、
該オルガノポリシロキサンの量は(A)成分100質量部に対して5〜900質量部である、及び
(C)縮合触媒 触媒量。 - 式(1−1)または式(1−2)においてx=0である、請求項1記載の縮合硬化型シリコーン組成物。
- R1で示される基の少なくとも1つが炭素数6〜12の芳香族炭化水素基である、請求項1又は2記載の縮合硬化型シリコーン組成物。
- 上記(A)分岐状オルガノポリシロキサンが、ケイ素原子に結合する1価芳香族炭化水素基を、ケイ素原子に結合する全置換基の合計個数のうち3%以上で有する、請求項1〜3のいずれか1項に記載の縮合硬化型シリコーン組成物。
- 式(1−1)及び式(1−2)において3≦a+b≦300である、請求項1〜4のいずれか1項記載の縮合硬化型シリコーン組成物。
- LED素子封止用である、請求項1〜5のいずれか1項記載の縮合硬化型シリコーン組成物。
- 請求項1〜6のいずれか1項記載の縮合硬化型シリコーン組成物を硬化して得られる硬化物を備える半導体装置。
- 前記半導体装置が半導体素子を備え、該半導体素子は前記硬化物で被覆されている、請求項7記載の半導体装置。
- 半導体素子が発光素子である、請求項8記載の半導体装置。
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