JP7222569B2 - 硬化性シリコーン組成物及び光半導体装置 - Google Patents
硬化性シリコーン組成物及び光半導体装置 Download PDFInfo
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- JP7222569B2 JP7222569B2 JP2022016324A JP2022016324A JP7222569B2 JP 7222569 B2 JP7222569 B2 JP 7222569B2 JP 2022016324 A JP2022016324 A JP 2022016324A JP 2022016324 A JP2022016324 A JP 2022016324A JP 7222569 B2 JP7222569 B2 JP 7222569B2
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Description
(A)平均組成式:
R11 aSiO(4-a)/2
(式中、R11は非置換又はハロゲン置換の一価炭化水素基、アルコキシ基、もしくは水酸基を表し、ただし、一分子中、少なくとも2個のR11はアルケニル基であり、全R11の少なくとも5モル%はアリール基であり、aは0.6~2.2の数である。)
で表されるオルガノポリシロキサン、
(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し、水素原子以外のケイ素原子結合基の少なくとも5モル%がアリール基であ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0.1~5モルとなる量}、
(C)平均単位式:
(R21SiO3/2)b(R22SiO3/2)c(R23 2SiO2/2)d(R23 3SiO1/2)e(XO1/2)f
{式中、R21はアリール基、R22はアルケニル基、R23は独立して、アルキル基、アルケニル基、アリール基、又はエポキシ含有有機基を表し、ただし、一分子中のR21、R22及びR23の合計に対して、少なくとも5モル%がアルケニル基であり、少なくとも15モル%がアリール基であり、少なくとも10モル%がエポキシ含有有機基であり、Xは水素原子又はアルキル基であり、b~fは、それぞれ、b~eの合計を1としたとき、bは正の数、cは正の数、dは0又は正の数、eは0又は正の数、fは0~0.02の数、かつ、c/bは0.1~5の数、b+cは0.2~0.8の数である。}
で表されるオルガノポリシロキサン{(A)成分と(B)成分の合計100質量部に対して0.1~20質量部}、及び
(D)本組成物の硬化を促進する量のヒドロシリル化反応用触媒
から少なくともなることを特徴とする。
R12 3SiO(R12 2SiO)mSiR12 3
(式中、R12は独立して、非置換又はハロゲン置換の一価炭化水素基を表し、ただし、一分子中、少なくとも2個のR12はアルケニル基であり、全R12の少なくとも5モル%がアリール基であり、mは5~1,000の整数である。)
で表される直鎖状のオルガノポリシロキサン及び/又は平均単位式:
(R12SiO3/2)g(R12 2SiO2/2)h(R12 3SiO1/2)i(SiO4/2)j(YO1/2)k
{式中、R12は前記と同じであり、ただし、一分子中、少なくとも2個のR12はアルケニル基であり、全R12の少なくとも5モル%がアリール基であり、Yは水素原子又はアルキル基であり、g~kは、それぞれ、g~jの合計を1としたとき、gは正の数、hは0又は正の数、iは0又は正の数、jは0~0.3の数、kは0~0.4の数、かつ、h/gは0~10の数、i/gは0~5の数である。}
で表される分岐鎖状のオルガノポリシロキサンであることが好ましい。
R31 3SiO(R31 2SiO)nSiR31 3
(式中、R31は独立して、脂肪族不飽和結合を有さない非置換もしくはハロゲン置換の一価炭化水素基、又は水素原子を表し、ただし、一分子中、少なくとも2個のR31は水素原子であり、水素原子を除く全R31の少なくとも5モル%がアリール基であり、nは1~1,000の整数である。)
で表される直鎖状のオルガノポリシロキサン及び/又は平均単位式:
(R31SiO3/2)p(R31 2SiO2/2)q(R31 3SiO1/2)r(SiO4/2)s(ZO1/2)t
{式中、R31は前記と同じであり、ただし、一分子中、少なくとも2個のR31は水素原子であり、水素原子を除く全R31の少なくとも5モル%がアリール基であり、Zは水素原子又はアルキル基であり、p~tは、それぞれ、p~sの合計を1としたとき、pは正の数、qは0又は正の数、rは0又は正の数、sは0~0.3の数、tは0~0.4の数、かつ、q/pは0~10の数、r/pは0~5の数である。}
で表される分岐鎖状のオルガノポリシロキサンであることが好ましい。
(A)成分は、平均組成式:
R11 aSiO(4-a)/2
で表されるオルガノポリシロキサンである。
R12 3SiO(R12 2SiO)mSiR12 3
で表される直鎖状のオルガノポリシロキサン及び/又は平均単位式:
(R12SiO3/2)g(R12 2SiO2/2)h(R12 3SiO1/2)i(SiO4/2)j(YO1/2)k
で表される分岐鎖状のオルガノポリシロキサンが好ましい。
R31 3SiO(R31 2SiO)nSiR31 3
で表される直鎖状のオルガノポリシロキサン及び/又は平均単位式:
(R31SiO3/2)p(R31 2SiO2/2)q(R31 3SiO1/2)r(SiO4/2)s(ZO1/2)t
で表される分岐鎖状のオルガノポリシロキサンが好ましい。
(R21SiO3/2)b(R22SiO3/2)c(R23 2SiO2/2)d(R23 3SiO1/2)e(XO1/2)f
で表されるオルガノポリシロキサンである。
本発明の光半導体装置は、上記の硬化性シリコーン組成物の硬化物により光半導体素子を封止してなることを特徴とする。このような本発明の光半導体装置としては、発光ダイオード(LED)、フォトカプラー、CCDが例示される。また、光半導体素子としては、発光ダイオード(LED)チップ、固体撮像素子が例示される。
(a1):平均式:
ViMe2SiO(MePhSiO)23SiMe2Vi
で表され、平均組成式:
Me1.08Ph0.92Vi0.08SiO0.96
で表される分子鎖両末端ジメチルビニルシロキシ基封鎖メチルフェニルポリシロキサン(フェニル基の含有量=44.2モル%)
(a2):平均式:
ViMe2SiO(Me2SiO)200(Ph2SiO)50SiMe2Vi
で表され、平均組成式:
Me1.60Ph0.40Vi0.01SiO1.00
で表される分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルジフェニルポリシロキサン(フェニル基の含有量=19.8モル%)
(a3):平均式:
ViPh2SiO(Me2SiO)11.3SiPh2Vi
で表され、平均組成式:
Me1.70Ph0.30Vi0.15SiO0.93
で表される分子鎖両末端ジフェニルビニルシロキシ基封鎖ジメチルポリシロキサン(フェニル基の含有量=14.0モル%)
(a4):一分子中に少なくとも2個のビニル基を有し、平均単位式:
(Me2ViSiO1/2)0.25(PhSiO3/2)0.75
で表され、平均組成式:
Me0.50Ph0.75Vi0.25SiO1.25
で表されるオルガノポリシロキサン(フェニル基の含有量=50.0モル%)
(a5):一分子中に少なくとも2個のビニル基を有し、平均単位式:
(Me2ViSiO1/2)0.11(Me3SiO1/2)0.14(MeSiO3/2)0.53(PhSiO3/2)0.22
で表され、平均組成式:
Me1.17Ph0.22Vi0.11SiO1.25
で表されるオルガノポリシロキサン(フェニル基の含有量=14.7モル%)
(a6):一分子中に少なくとも2個のビニル基を有し、平均単位式:
(Me2ViSiO1/2)0.20(PhSiO3/2)0.80
で表され、平均組成式:
Me0.40Ph0.80Vi0.20SiO1.30
で表されるオルガノポリシロキサン(フェニル基の含有量=57.1モル%)
(b1):式:
HMe2SiO(Ph2SiO)SiMe2H
で表されるオルガノトリシロキサン(フェニル基の含有量=33.3モル%)
(b2):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し、平均単位式:
(HMe2SiO1/2)0.60(PhSiO3/2)0.40
で表されるオルガノポリシロキサン(フェニル基の含有量=25.0モル%)
(c1):粘度が4,800mPa・sであり、平均単位式:
(ViSiO3/2)0.21(PhSiO3/2)0.31(EpMeSiO2/2)0.48
で表されるオルガノポリシロキサン(ビニル基の含有量=14.2モル%、フェニル基の含有量=21.0モル%、3-グリシドキシプロピル基の含有量=32.4モル%)
(c2):粘度が6,000mPa・sであり、平均単位式:
(ViSiO3/2)0.24(PhSiO3/2)0.27(EpMeSiO2/2)0.49
で表されるオルガノポリシロキサン(ビニル基の含有量=16.1モル%、フェニル基の含有量=18.1モル%、3-グリシドキシプロピル基の含有量=32.9モル%)
(c3):粘度が7,000mPa・sであり、平均単位式:
(ViSiO3/2)0.15(PhSiO3/2)0.31(EpMeSiO2/2)0.54
で表されるオルガノポリシロキサン(ビニル基の含有量=9.7モル%、フェニル基の含有量=20.1モル%、3-グリシドキシプロピル基の含有量=35.1モル%)
(c4):粘度が19,000mPa・sであり、平均単位式:
(PhSiO3/2)0.53(EpMeSiO2/2)0.29(Me2ViSiO1/2)0.18
で表されるオルガノポリシロキサン(ビニル基の含有量=10.9モル%、フェニル基の含有量=32.1モル%、3-グリシドキシプロピル基の含有量=17.6モル%)
(d):白金金属の含有量が約4質量%である、白金の1,3-ジビニル-1,1,3,3-テトラメチルジシロキサン錯体の1,3-ジビニル-1,1,3,3-テトラメチルジシロキサン溶液
(e1):1-エチニルシクロヘキサン-1-オール
(e2):平均式:
(MeViSiO)4
で表される環状メチルビニルポリシロキサン
硬化性シリコーン組成物の屈折率を、アッベ式屈折率計を用いて25℃で測定した。なお、光源として、可視光(589nm)を用いた。
硬化性シリコーン組成物の調製直後の25℃における粘度(mPa・s)を回転粘度計(トキメック株式会社製のE型粘度計VISCONIC EMD)を使用して測定した。また、25℃において、その粘度が5万mPa・sに達するまでの時間を測定した。
実施例1-5及び比較例1、2の硬化性シリコーン組成物 各5gに、緑蛍光体(INTEMATIX製の製品名:GAL530) 1.035g、赤色蛍光体(INTEMATIX製の製品名:ER6535) 0.082g加えて均一に混合して、7種の硬化性シリコーン組成物を調製した。これらの硬化性シリコーン組成物を、図1に示すような光半導体装置に注入し、150℃で2時間硬化させて光半導体装置を作製した。これらの光半導体装置の光取り出し効率を、積分球を用いた全放射束測定装置を使用して放射束測定を行った。
表1に示した組成で硬化性シリコーン組成物を調製した。なお、表1中の「SiH/Vi」は、(A)成分中のビニル基の合計1モルに対する、(B)成分中のケイ素原子結合水素原子の合計モル数の値を表す。また、この硬化性シリコーン組成物の特性およびこの組成物を用いて作製した光半導体装置の特性を表1に示した。
2 リードフレーム
3 リードフレーム
4 ボンディングワイヤ
5 枠材
6 硬化性シリコーン組成物の硬化物
Claims (5)
- (A)平均組成式:
R11 aSiO(4-a)/2
(式中、R11は非置換又はハロゲン置換の一価炭化水素基、アルコキシ基、もしくは水酸基を表し、ただし、一分子中、少なくとも2個のR11はアルケニル基であり、全R11の5モル%~50.0モル%がフェニル基であり、aは0.6~2.2の数である。)
で表されるオルガノポリシロキサン、
(B)
(B-1)一般式:
R 31 3 SiO(R 31 2 SiO) n SiR 31 3
(式中、R 31 は独立して、脂肪族不飽和結合を有さない非置換もしくはハロゲン置換の一価炭化水素基、又は水素原子を表し、ただし、一分子中、少なくとも2個のR 31 は水素原子であり、水素原子以外の全R 31 の少なくとも5モル%がアリール基であり、nは1~1,000の整数である。)
で表される直鎖状のオルガノポリシロキサン及び
(B-2)平均単位式:
(R 31 SiO 3/2 ) p (R 31 2 SiO 2/2 ) q (R 31 3 SiO 1/2 ) r (SiO 4/2 ) s (ZO 1/2 ) t
{式中、R 31 は前記と同じであり、ただし、一分子中、少なくとも2個のR 31 は水素原子であり、水素原子以外の全R 31 の少なくとも5モル%がアリール基であり、Zは水素原子又はアルキル基であり、p~tは、それぞれ、p~sの合計を1としたとき、pは正の数、qは0又は正の数、rは0又は正の数、sは0~0.3の数、tは0~0.4の数、かつ、q/pは0~10の数、r/pは0~5の数である。}
で表される分岐鎖状のオルガノポリシロキサン、
からな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0.1~5モルとなる量}、
(C)平均単位式:
(R21SiO3/2)b(R22SiO3/2)c(R23 2SiO2/2)d(R23 3SiO1/2)e(XO1/2)f
{式中、R21はアリール基、R22はアルケニル基、R23は独立して、アルキル基、アルケニル基、アリール基、又はエポキシ含有有機基を表し、ただし、一分子中のR21、R22及びR23の合計に対して、少なくとも5モル%がアルケニル基であり、15モル%~25モル%がフェニル基であり、少なくとも10モル%がエポキシ含有有機基であり、Xは水素原子又はアルキル基であり、b~fは、それぞれ、b~eの合計を1としたとき、bは正の数、cは正の数、dは0又は正の数、eは0又は正の数、fは0~0.02の数、かつ、c/bは0.1~5の数、b+cは0.2~0.8の数である。}
で表されるオルガノポリシロキサン{(A)成分と(B)成分の合計100質量部に対して0.1~20質量部}、及び
(D)本組成物の硬化を促進する量のヒドロシリル化反応用触媒
を少なくとも含んでなる硬化性シリコーン組成物。 - (A)成分が、一般式:
R12 3SiO(R12 2SiO)mSiR12 3
(式中、R12は独立して、非置換又はハロゲン置換の一価炭化水素基を表し、ただし、一分子中、少なくとも2個のR12はアルケニル基であり、全R12の5モル%~50.0モル%がフェニル基であり、mは5~1,000の整数である。)
で表される直鎖状のオルガノポリシロキサン及び/又は平均単位式:
(R12SiO3/2)g(R12 2SiO2/2)h(R12 3SiO1/2)i(SiO4/2)j(YO1/2)k
{式中、R12は前記と同じであり、ただし、一分子中、少なくとも2個のR12はアルケニル基であり、全R12の5モル%~50.0モル%がフェニル基であり、Yは水素原子又はアルキル基であり、g~kは、それぞれ、g~jの合計を1としたとき、gは正の数、hは0又は正の数、iは0又は正の数、jは0~0.3の数、kは0~0.4の数、かつ、h/gは0~10の数、i/gは0~5の数である。}
で表される分岐鎖状のオルガノポリシロキサンである、請求項1に記載の硬化性シリコーン組成物。 - (C)成分が、25℃において100~20,000mPa・sの粘度を有する、請求項1に記載の硬化性シリコーン組成物。
- さらに、(E)ヒドロシリル化反応抑制剤を、(A)成分~(C)成分の合計100質量部に対して0.0001~5質量部含有する、請求項1乃至3のいずれか1項に記載の硬化性シリコーン組成物。
- 請求項1乃至4のいずれか1項に記載の硬化性シリコーン組成物の硬化物により被覆されている光半導体素子を含んでなる光半導体装置。
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JPWO2012157330A1 (ja) * | 2011-05-17 | 2014-07-31 | 積水化学工業株式会社 | 光半導体装置用封止剤及び光半導体装置 |
CN102977554B (zh) * | 2012-11-06 | 2015-02-04 | 中科院广州化学有限公司 | 一种led封装用环氧/有机硅共固化复合材料及其制备方法 |
KR101676520B1 (ko) * | 2013-10-24 | 2016-11-15 | 제일모직주식회사 | 유기발광소자 봉지용 조성물 및 이를 사용하여 제조된 유기발광소자 표시장치 |
WO2016136245A1 (ja) * | 2015-02-27 | 2016-09-01 | 東レ・ダウコーニング株式会社 | オルガノポリシロキサン、その製造方法、および硬化性シリコーン組成物 |
JP6707369B2 (ja) * | 2015-03-30 | 2020-06-10 | ダウ・東レ株式会社 | シリコーン材料、硬化性シリコーン組成物、および光デバイス |
JP2017145358A (ja) * | 2016-02-19 | 2017-08-24 | 株式会社ダイセル | 硬化性シリコーン樹脂組成物及びその硬化物 |
DE102016206823A1 (de) * | 2016-04-21 | 2017-10-26 | Man Diesel & Turbo Se | Zentrifuge sowie Einsatz und Bodenelement für eine Zentrifuge |
JP6519531B2 (ja) * | 2016-06-03 | 2019-05-29 | 信越化学工業株式会社 | 付加硬化性シリコーン樹脂組成物及び光半導体装置用ダイアタッチ材 |
CN106380862A (zh) * | 2016-10-26 | 2017-02-08 | 三友(天津)高分子技术有限公司 | 紫外发光二极管封装用有机聚硅氧烷组合物及制备方法 |
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WO2019078046A1 (ja) | 2019-04-25 |
TW201917173A (zh) | 2019-05-01 |
JP2022158926A (ja) | 2022-10-17 |
US20200299510A1 (en) | 2020-09-24 |
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