JP2015529713A - ポリカルボシランおよびヒドロシリコーンを含んでなるled封入剤用硬化性組成物 - Google Patents
ポリカルボシランおよびヒドロシリコーンを含んでなるled封入剤用硬化性組成物 Download PDFInfo
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- JP2015529713A JP2015529713A JP2015524588A JP2015524588A JP2015529713A JP 2015529713 A JP2015529713 A JP 2015529713A JP 2015524588 A JP2015524588 A JP 2015524588A JP 2015524588 A JP2015524588 A JP 2015524588A JP 2015529713 A JP2015529713 A JP 2015529713A
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- polycarbosilane
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- organopolysiloxane
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- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
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- 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
- C08L83/16—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- 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
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- 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
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- C08G77/04—Polysiloxanes
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Abstract
Description
(A)下記一般式:
で示されるオルガノポリシロキサン;
(B)下記平均単位式:
で示されるオルガノポリシロキサン;
(C)一分子中に平均して少なくとも2個のケイ素結合アリール基と平均して少なくとも2個のケイ素結合水素原子とを有するオルガノポリシロキサン;および
(D)ヒドロシリル化反応触媒。この組成物は良好なギャップ充填性および硬化性を特徴としており、硬化すると、高い屈折率、高い光透過率、および様々な基材との強い接着性を有する硬化体を生じる。
で示される少なくとも1つのポリカルボシランA、
(B)下記式(2):
で示される少なくとも1つのオルガンポリシロキサンB、および
(C)少なくとも1つの触媒
を含んでなる硬化性組成物、特にLED封入剤用透明組成物に関する。
で示されるアミノシランを含んでなる。そのような化合物は、本発明の硬化性組成物の結合性ポリマー成分に対してだけでなく広い範囲の極性および非極性表面に対して高い親和性を本質的に示し、従って、それぞれの場合に、結合または封入される基材と硬化組成物との特に安定な接着の形成に寄与する。
以下のように評価を行った。
下記実施例では、重量平均分子量値(g/mol)は、ゲル浸透クロマトグラフィー(GPC)を用いて測定されるポリスチレン換算値である。
ビニル含量は、Chinese Chemical Industry Standard HG/T 3312-2000に従って滴定した。
水素含量は、Feng S. Y.; Zhang, J.; Li, M. J.; Zhu, Q. Z.; Organosilicon Polymer and Application Thereof, 第400〜401頁;Chemical Industry Pressに記載されているように滴定した。
透過率は、紫外可視分光分析装置Lambda 650S(PerkinElmer Corporation製)によって測定した。透過率は、300nm〜800nmの範囲について測定し、450nmでの値を透過率として記録した。
透過性は、50℃/100%RH(RH=相対湿度)で、Mocon Permatran-W(登録商標)モデル3/33によって測定した。
ジビニルジメチルシラン(CAS:10519-87-6)をRuilijie Chemical Companyから購入した。ジフェニルシラン(CAS:775-12-2)、およびトリビニルメチルシラン(CAS:18244-95-6)をGelestから購入した。白金触媒SIP6832.2(環式メチルビニルシロキサン中白金濃度2.0〜2.3%、CAS:68585-32-0)をGelestから購入した。HPM-502(100mPas・Sの粘度、1359g/molの重量平均分子量、6.06mmol/gの水素含量および35.4重量%のフェニル含量を有するヒドリド末端メチルヒドロシロキサン−フェニルメチルシロキサンコポリマー)を、Gelestから購入した。
乾いた清浄な100mL容二ツ口丸底フラスコに、9.22gのジフェニルシラン、6.16gのジビニルジメチルシラン、0.008gの白金触媒SIP 6832.2および6.28gのキシレンを添加した。マグネチックスターラーを入れ、フラスコに止め具および冷却器をかぶせた。混合物を撹拌しながら75℃に加熱し、この温度で1時間保持し、次いで130℃で6時間更に加熱した。115℃および20mbarで1時間、その後135℃および5mbarで更に1時間回転蒸発することにより、未反応モノマーを除去した。得られた液体は3072g/molの重量平均分子量を有しており、そのビニル含量は0.65mmol/gであった。得られたポリマーは、下記平均式を有していた。
乾いた清浄な100mL容二ツ口丸底フラスコに、9.22gのジフェニルシラン、7.44gのトリビニルメチルシラン、0.016gの白金触媒SIP 6832.2および6.28gのトルエンを添加した。マグネチックスターラーを入れ、フラスコに止め具および冷却器をかぶせた。混合物を撹拌しながら75℃に加熱し、この温度で1時間保持し、次いで130℃で6時間更に加熱した。115℃および20mbarで1時間、その後135℃および5mbarで更に1時間回転蒸発することにより、未反応モノマーを除去した。得られた液体ポリマーは分岐構造を有しており、1662g/molの重量平均分子量を有しており、そのビニル含量は3.6mmol/gであった。
100gの合成例1のビニルポリカルボシラン、21.5gのオルガノハイドロジェンポリシロキサンHPM-502、0.001gの白金触媒SIP6832.2および0.001gの阻害剤3,5−ジメチル−1−ヘキシン−3−オールを混合した。得られた混合物を150℃で2時間加熱し、硬化生成物を得た。透過性、亀裂、接着/積層、450nmでの初期透明性(450nmでのT(初期))、および150℃で100時間生成物を熱処理した後の450nmでの透明性(450nmでのT(150℃、100時間))について、生成物を評価した。結果を表1に示す。
100gの合成例2のビニルポリカルボシラン、55gのオルガノハイドロジェンポリシロキサンHPM-502、0.001gの白金触媒SIP6832.2および0.001gの阻害剤3,5−ジメチル−1−ヘキシン−3−オールを混合した。得られた混合物を150℃で2時間加熱し、硬化生成物を得た。透過性、亀裂、接着/積層、450nmでの初期透明性(450nmでのT(初期))、および150℃で100時間生成物を熱処理した後の450nmでの透明性(450nmでのT(150℃、100時間))について、生成物を評価した。結果を表1に示す。
Dow Corningから6636の商品名で市販されている高RI(屈折率)封入材料の2つの成分AおよびBを、A:B=1:2の重量比で混合し、70℃で1時間、120℃で1時間、および最後に150℃で1時間加熱した。透過性、亀裂、接着/積層、450nmでの初期透明性(450nmでのT(初期))、および150℃で100時間生成物を熱処理した後の450nmでの透明性(450nmでのT(150℃、100時間))について、得られた硬化生成物を評価した。結果を表1に示す。
Claims (11)
- 下記式(1):
で示される少なくとも1つのポリカルボシランA、
(B)下記式(2):
で示される少なくとも1つのオルガンポリシロキサンB、および
(C)少なくとも1つの触媒
を含んでなる硬化性組成物。 - T+Qが0より大きい、式(1)で示されるポリカルボシランAを含んでなる、請求項1に記載の組成物。
- ポリカルボシランAの重量平均分子量が100〜300,000g/mol、好ましくは1,000〜50,000g/molである、請求項1に記載の組成物。
- D’が0より大きい、式(2)で示されるオルガノポリシロキサンBを含んでなる、請求項1に記載の組成物。
- ポリカルボシランAおよびオルガノポリシロキサンBは、0.5〜10、好ましくは1.0〜3.0のSi−H/Si−ビニルモル比をもたらす各々の量で存在する、請求項1に記載の組成物。
- オルガノポリシロキサンBの重量平均分子量が、1,000〜300,000g/mol、好ましくは10,000〜100,000g/molである、請求項1に記載の組成物。
- 触媒は白金族金属触媒からなる群から選択される1つ以上である、請求項1に記載の組成物。
- 触媒金属の含量が硬化性組成物の総重量に基づいて1〜500ppm、好ましくは2〜100ppmの範囲になるような量で触媒は存在する、請求項1に記載の組成物。
- 組成物は、成分1および成分2からなる二成分組成物であり、成分1は、ポリカルボシランAおよび存在する触媒の全量を含んでなり、成分2は、存在するオルガノポリシロキサンBの全量および場合により更なるポリカルボシランAを含んでなる、請求項1に記載の組成物。
- 請求項1〜9のいずれかに記載の硬化性組成物を加熱することにより得られる硬化生成物。
- 半導体封入材料および/または電子素子包装材料としての、請求項1〜9のいずれかに記載の組成物の使用。
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JP5176976B2 (ja) * | 2009-01-21 | 2013-04-03 | Jsr株式会社 | 硬化性組成物 |
US8026331B2 (en) * | 2009-04-21 | 2011-09-27 | The United States Of America As Represented By The Secretary Of The Navy | Polymers made from polyhedral oligomeric silsesquioxanes and diacetylene-containing compounds |
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2012
- 2012-08-02 CN CN201280074976.2A patent/CN104662098A/zh active Pending
- 2012-08-02 KR KR20157002623A patent/KR20150037952A/ko not_active Application Discontinuation
- 2012-08-02 JP JP2015524588A patent/JP2015529713A/ja active Pending
- 2012-08-02 EP EP12882183.2A patent/EP2880095B1/en not_active Not-in-force
- 2012-08-02 WO PCT/CN2012/079587 patent/WO2014019195A1/en active Application Filing
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2013
- 2013-06-14 TW TW102121024A patent/TW201406864A/zh unknown
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2015
- 2015-01-30 US US14/609,984 patent/US9359478B2/en not_active Expired - Fee Related
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JPH07233260A (ja) * | 1993-12-28 | 1995-09-05 | Kanegafuchi Chem Ind Co Ltd | 反応性ケイ素系高分子、及びそれを用いた硬化性組成物 |
JPH10140009A (ja) * | 1996-11-06 | 1998-05-26 | Kanegafuchi Chem Ind Co Ltd | 電気絶縁材料用熱硬化性樹脂組成物 |
JPH10152616A (ja) * | 1996-11-25 | 1998-06-09 | Kanegafuchi Chem Ind Co Ltd | 電気絶縁材料用熱硬化性樹脂組成物 |
JPH1180362A (ja) * | 1997-08-29 | 1999-03-26 | Toray Dow Corning Silicone Co Ltd | シルフェニレンシルアルキレンポリマーの製造方法 |
JP2012052045A (ja) * | 2010-09-02 | 2012-03-15 | Shin-Etsu Chemical Co Ltd | 低ガス透過性シリコーン樹脂組成物及び光半導体装置 |
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KR20150037952A (ko) | 2015-04-08 |
EP2880095A1 (en) | 2015-06-10 |
US9359478B2 (en) | 2016-06-07 |
WO2014019195A1 (en) | 2014-02-06 |
CN104662098A (zh) | 2015-05-27 |
EP2880095A4 (en) | 2016-01-13 |
US20150148510A1 (en) | 2015-05-28 |
EP2880095B1 (en) | 2017-03-29 |
TW201406864A (zh) | 2014-02-16 |
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