JP5922463B2 - 硬化性シリコーン組成物、その硬化物、および光半導体装置 - Google Patents
硬化性シリコーン組成物、その硬化物、および光半導体装置 Download PDFInfo
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- JP5922463B2 JP5922463B2 JP2012079251A JP2012079251A JP5922463B2 JP 5922463 B2 JP5922463 B2 JP 5922463B2 JP 2012079251 A JP2012079251 A JP 2012079251A JP 2012079251 A JP2012079251 A JP 2012079251A JP 5922463 B2 JP5922463 B2 JP 5922463B2
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
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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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- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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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
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- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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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
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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Description
(A)(A1)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水酸基およびケイ素原子結合水素原子を有さないオルガノポリシロキサン、または該(A1)成分と(A2)平均単位式:
(R1 2R2SiO1/2)a(R1 3SiO1/2)b(SiO4/2)c(HO1/2)d
{式中、R1は同じかまたは異なる炭素原子数1〜10のアルキル基であり、R2はアルケニル基であり、a、b、cおよびdはいずれも、a+b+c=1、a/(a+b)=0.15〜0.35、c/(a+b+c)=0.53〜0.62、d/(a+b+c)=0.005〜0.03を満たす正数である。}
で表される分岐鎖状オルガノポリシロキサンの混合物 100質量部、
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノポリシロキサン{(A)成分中のアルケニル基1モルに対して、本成分中のケイ素原子結合水素原子が0.1〜10モルとなる量}、
(C)一般式:
R3R4Si(OR5)2
(式中、R3はグリシドキシアルキル基、エポキシシクロヘキシルアルキル基、エポキシアルキル基、アクリロキシアルキル基、またはメタクリロキシアルキル基であり、R4は炭素原子数1〜6のアルキル基であり、R5は炭素原子数1〜4のアルキル基である。)
で表されるジオルガノジアルコキシシラン 0.01〜10質量部、
(D)一分子中に少なくとも1個のケイ素原子結合水酸基を有し、ケイ素原子結合水素原子を有さない直鎖状オルガノシロキサンオリゴマー 0.01〜10質量部、および
(E)触媒量のヒドロシリル化反応用触媒
から少なくともなる。
(A)成分は本組成物の主剤であり、(A1)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水酸基およびケイ素原子結合水素原子を有さないオルガノポリシロキサン、または該(A1)成分と(A2)平均単位式:
(R1 2R2SiO1/2)a(R1 3SiO1/2)b(SiO4/2)c(HO1/2)d
で表される分岐鎖状オルガノポリシロキサンの混合物である。
(R1 2R2SiO1/2)a(R1 3SiO1/2)b(SiO4/2)c(HO1/2)d
で表される。式中、R1は同じかまたは異なる炭素原子数1〜10のアルキル基であり、具体的には、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、シクロペンチル基、シクロヘキシル基が例示され、好ましくは、メチル基である。式中、R2はアルケニル基であり、ビニル基、アリル基、イソプロペニル基、ブテニル基、ヘキセニル基、シクロヘキセニル基が例示され、好ましくは、ビニル基である。式中、a、b、cおよびdはいずれも、a+b+c=1、a/(a+b)=0.15〜0.35、c/(a+b+c)=0.53〜0.62、d/(a+b+c)=0.005〜0.03を満たす正数である。本組成物に十分な硬化性を付与するため、a/(a+b)は0.2〜0.3の範囲内の数であることが好ましい。本組成物の硬化物に十分な硬さや機械的強度を付与するため、c/(a+b+c)は0.55〜0.60の範囲内の数であることが好ましい。本組成物の硬化物に十分な接着性や機械的強度を付与するため、d/(a+b+c)は0.01〜0.025の範囲内の数であることが好ましい。
R3R4Si(OR5)2
で表されるジオルガノジアルコキシシランである。式中、R3は、3−グリシドキシプロピル基、4−グリシドキシブチル基等のグリシドキシアルキル基;2−(3,4−エポキシシクロヘキシル)エチル基、3−(3,4−エポキシシクロヘキシル)プロピル基等のエポキシシクロヘキシルアルキル基;5,6−エポキシヘキシル基、9,10−エポキシデシル基等のエポキシアルキル基;3−アクリロキシプロピル基、4−アクリロキシブチル基等のアクリロキシアルキル基;または3−メタクリロキシプロピル基、4−メタクリロキシブチル基等のメタクリロキシアルキル基である。式中、R4は炭素原子数1〜6のアルキル基であり、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基が例示され、好ましくは、メチル基である。式中、R5は炭素原子数1〜4のアルキル基であり、メチル基、エチル基、プロピル基、ブチル基が例示され、好ましくは、メチル基、エチル基である。
本発明の光半導体装置は、光半導体素子、および該素子を封止または接着してなる上記組成物の硬化物からなることを特徴とする。この光半導体素子としては、発光ダイオード(LED)、半導体レーザ、フォトダイオード、フォトトランジスタ、固体撮像、フォトカプラー用発光体と受光体が例示され、好ましくは、発光ダイオード(LED)である。
硬化性シリコーン組成物を150℃で1時間加熱して硬化物を作製した。この硬化物の硬さをJIS K 6253に規定されたタイプAデュロメータを用いて測定した。
硬化性シリコーン組成物を150℃で1時間加熱して、光路長1.0mmの硬化物を作製した。この硬化物の波長450nmにおける光透過率を測定した。
2枚のポリフタルアミド(PPA)樹脂板(幅25mm、長さ50mm、厚さ1mm)間にポリテトラフルオロエチレン樹脂製スペーサ(幅10mm、長さ20mm、厚さ1mm)を挟み込み、その隙間に硬化性シリコーン組成物を充填し、クリップで留め、150℃の熱風循環式オーブン中で1時間加熱して前記組成物を硬化させた。室温に冷却後、クリップとスペーサを外した試験片を引張試験機により水平反対方向に引張って、硬化物の接着力を測定した。
次の成分を表1に示す組成で均一に混合して硬化性シリコーン組成物を調製した。なお、式中、Viはビニル基を表し、Meはメチル基を示す。また、表中、SiH/Viは、硬化性シリコーン組成物において、(A−1)〜(A−4)成分中のビニル基の合計1モルに対する(B−1)〜(B−2)成分中のケイ素原子結合水素原子の合計モル数を示し、光線透過率の変化率は、初期の光線透過率に対する高温高湿処理後の光線透過率の変化率を示し、接着力の変化率は、初期の接着力に対する高温高湿処理後の接着力の変化率を示す。
(A−2)成分:粘度11,000mPa・sの分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルポリシロキサン(ビニル基の含有量=0.14質量%)
(A−3)成分:25℃において白色固体状で、トルエン可溶性である、平均単位式:
(ViMe2SiO1/2)0.13(Me3SiO1/2)0.45(SiO4/2)0.42(HO1/2)0.01
で表されるオルガノポリシロキサンレジン(ビニル基の含有量=3.4質量%)
(A−4)成分:25℃において白色固体状で、トルエン可溶性である、平均単位式:
(ViMe2SiO1/2)0.15(Me3SiO1/2)0.38(SiO4/2)0.47(HO1/2)0.01
で表されるオルガノポリシロキサン(ビニル基の含有量=4.2質量%)
(B−1)成分:粘度5mPa・sの分子鎖両末端トリメチルシロキシ基封鎖ジメチルシロキサン・メチルハイドロジェンシロキサン共重合体(ケイ素原子結合水素原子の含有量=1.4質量%)
(B−2)成分:粘度20mPa・sの分子鎖両末端トリメチルシロキシ基封鎖ポリメチルハイドロジェンシロキサン(ケイ素原子結合水素原子含有量=1.57質量%)
(C−1)成分:3−グリシドキシプロピルトリメトキシシラン
(C−2)成分:3−グリシドキシプロピルメチルジメトキシシラン
(C−3)成分:3−グリシドキシプロピルメチルジエトキシシラン
(C−4)成分:3−アクリロキシプロピルメチルジメトキシシラン
(D−1)成分:粘度40mPa・sであり、分子鎖両末端がケイ素原子結合水酸基で封鎖されたジメチルシロキサン・メチルビニルシロキサン共重合オリゴマー
(E−1)成分:白金の1,3−ジビニルテトラメチルジシロキサン錯体の1,3−ジビニルテトラメチルジシロキサン溶液(白金金属の含有量=4,000ppm)
(F−1)成分:3,5−ジメチル−1−オクチン−3−オール
2 インナーリード
3 ダイパッド
4 接着材
5 発光ダイオード(LED)チップ
6 ボンディングワイヤ
7 封止材
Claims (4)
- (A)(A1)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水酸基およびケイ素原子結合水素原子を有さないオルガノポリシロキサン、または該(A1)成分と(A2)平均単位式:
(R1 2R2SiO1/2)a(R1 3SiO1/2)b(SiO4/2)c(HO1/2)d
{式中、R1は同じかまたは異なる炭素原子数1〜10のアルキル基であり、R2はアルケニル基であり、a、b、cおよびdはいずれも、a+b+c=1、a/(a+b)=0.15〜0.35、c/(a+b+c)=0.53〜0.62、d/(a+b+c)=0.005〜0.03を満たす正数である。}
で表される分岐鎖状オルガノポリシロキサンの混合物 100質量部、
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノポリシロキサン{(A)成分中のアルケニル基1モルに対して、本成分中のケイ素原子結合水素原子が0.1〜10モルとなる量}、
(C)一般式:
R3R4Si(OR5)2
(式中、R3はグリシドキシアルキル基、エポキシシクロヘキシルアルキル基、エポキシアルキル基、アクリロキシアルキル基、またはメタクリロキシアルキル基であり、R4は炭素原子数1〜6のアルキル基であり、R5は炭素原子数1〜4のアルキル基である。)
で表されるジオルガノジアルコキシシラン 0.01〜10質量部、
(D)一分子中に少なくとも1個のケイ素原子結合水酸基を有し、ケイ素原子結合水素原子を有さない直鎖状オルガノシロキサンオリゴマー 0.01〜10質量部、および
(E)触媒量のヒドロシリル化反応用触媒
から少なくともなる、光半導体素子を封止あるいは接着するための硬化性シリコーン組成物。 - (A)成分が(A1)成分と(A2)成分の混合物であり、(A)成分中の(A2)成分の含有量が60質量%以下である、請求項1記載の硬化性シリコーン組成物。
- 光半導体素子、および該素子を封止または接着してなる請求項1または2記載の硬化性シリコーン組成物の硬化物からなる光半導体装置。
- 光半導体素子が発光ダイオードである、請求項3記載の光半導体装置。
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US20150069456A1 (en) | 2015-03-12 |
JP2013209454A (ja) | 2013-10-10 |
KR20140145177A (ko) | 2014-12-22 |
TW201402656A (zh) | 2014-01-16 |
WO2013146334A1 (en) | 2013-10-03 |
TWI567112B (zh) | 2017-01-21 |
CN104204100A (zh) | 2014-12-10 |
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