JP6384046B2 - 光反射性異方性導電接着剤及び発光装置 - Google Patents
光反射性異方性導電接着剤及び発光装置 Download PDFInfo
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- JP6384046B2 JP6384046B2 JP2013253023A JP2013253023A JP6384046B2 JP 6384046 B2 JP6384046 B2 JP 6384046B2 JP 2013253023 A JP2013253023 A JP 2013253023A JP 2013253023 A JP2013253023 A JP 2013253023A JP 6384046 B2 JP6384046 B2 JP 6384046B2
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Description
本発明は、発光素子を配線板に異方性導電接続するために使用する光反射性異方性導電接着剤であって、熱硬化性樹脂組成物、導電粒子及び光反射性絶縁粒子を含有する光反射性異方性導電接着剤である。まず、バインダーである熱硬化性樹脂組成物について説明する。
(ジグリシジルイソシアヌリル変性環状ポリシロキサン)
本発明において、熱硬化性樹脂組成物は、式(1)で表されるジグリシジルイソシアヌリル変性環状ポリシロキサンと、エポキシ樹脂用硬化剤とを含有する。式(1)で表されるジグリシジルイソシアヌリル変性環状ポリシロキサンを含有することにより、熱や光により異方性導電接着剤が変色してしまうことを防止でき、しかも実用上十分なダイシェア強度を実現することができる。
式(1)で表されるジグリシジルイソシアヌリル変性環状ポリシロキサンは、以下の反応式に示すように、式(a)のハイドロジェン環状ポリシロキサンと、式(b)の1−アリル−3,5−ジグリシジルイソシアヌレートとを、窒素などの不活性ガス雰囲気下、適当な溶媒中で、好ましくは無溶媒で均一に混合した後、ハイドロシリル化を触媒可能な白金触媒の存在下で、好ましくは室温〜150℃に加熱し、ハイドロシリレーション反応させることにより製造することができる。反応混合物からは、常法(濃縮処理・カラム処理等)により式(1)の化合物を単離することができる。なお、反応式中の置換基は、既に式(1)に関連して説明したとおりである。
ここで、ハイドロシリレーション反応の際の白金触媒の濃度は、20ppm以下、好ましくは15ppm以下、特に好ましくは10ppm以下である。なお、白金触媒の好ましい下限濃度は、少なくとも1.0ppmである。白金触媒の濃度がこの範囲であれば、ハイドロシリレーション反応をスムーズに進行させ、また、光反射性異方性導電接着剤の熱や光による着色を、接着性を損なわずに抑制することができる。この白金触媒の濃度は、反応開始時点のハイドロジェン環状ポリシロキサンと末端不飽和アルケニル基を有するエポキシ基含有イソシアヌレートとの混合物中の濃度である。具体的には、白金触媒の濃度(Pt)は、ハイドロジェン環状ポリシロキサンや末端不飽和アルケニル基を有するエポキシ基含有イソシアヌレートに対し非常に微量であるため、ハイドロジェン環状ポリシロキサンの質量をW1、末端不飽和アルケニル基を有するエポキシ基含有イソシアヌレートの質量をW2、使用された白金触媒の固形分の質量をW3としたときに、以下の数式で定義される。通常は、“ppm”単位で表現される。
ハイドロシリル化を触媒可能な白金触媒としては、マイナスの電荷を帯びた錯体、0価、2価または4価の白金化合物および白金コロイドが挙げられる。マイナスの電荷を帯びた錯体としては、白金カルボニルクラスターアニオン化合物、例えば、[Pt3(CO)6]2−、[Pt3(CO)6]2 2−、[Pt3(CO)6]4 2−が例示される。0価の白金化合物としては、白金(0)ジビニルテトラメチルジシロキサン錯体、白金(0)テトラビニルテトラメチルシクロテトラシロキサン錯体、白金(0)エチレン錯体、白金(0)スチレン錯体が例示される。2価の白金化合物としては、Pt(II)Cl2,Pt(II)Br2、ビス(エチレン)Pt(II)Cl2、(1,5−シクロオクタジエン)Pt(II)Cl2、白金(II)アセチルアセトナート、ビス(ベンゾニトリル)Pt(II)Cl2が例示される。4価の白金化合物としては、Pt(IV)Cl4、H2Pt(IV)Cl6、Na2Pt(IV)Cl6、K2Pt(IV)Cl6が例示される。中でも、カールステッド(Karstedt)白金触媒(1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン白金(0)錯体)を好ましく使用できる。これらは、必要に応じてキシレンなどの溶媒に溶解させた溶液として使用することができる。
熱硬化性樹脂組成物は、式(1)のジグリシジルイソシアヌリル変性環状ポリシロキサンの他に、発明の効果を損なわない範囲で、複素環系エポキシ化合物や脂環式エポキシ化合物や水素添加エポキシ化合物などを含有することができる。
エポキシ樹脂用硬化剤としては、公知のエポキシ樹脂用硬化剤を使用することができる。例えば、アミン系硬化剤、ポリアミド系硬化剤、酸無水物系硬化剤、イミダゾール系硬化剤、ポリメルカプタン系硬化剤、ポリスルフィド系硬化剤、三フッ化ホウ素−アミン錯体系硬化剤、ジシアンジアミド、有機酸ヒドラジッド等の中から選択して使用することができる。中でも、光透過性、耐熱性等の観点から酸無水物系硬化剤を好ましく使用することができる。
本発明の光反射性異方性導電接着剤が含有する光反射性絶縁粒子は、異方性導電接着剤に入射した光を外部に反射するためのものである。
本発明の光反射性異方性導電接着剤を構成する導電粒子としては、異方性導電接続用の従来の導電粒子において用いられている金属の粒子を利用することができる。例えば、金、ニッケル、銅、銀、半田、パラジウム、アルミニウム、それらの合金、それらの多層化物(例えば、ニッケルメッキ/金フラッシュメッキ物)等を挙げることができる。中でも、金、ニッケル、銅は、導電粒子を茶色としてしまうことから、本発明の効果を他の金属材料よりも享受することができる。
観点からみると、コア粒子1の粒径に対し、小さすぎると反射率の低下が著しくなり、大
きすぎると導通不良が生ずるので、好ましくは0.5〜50%、より好ましくは1〜25
%である。
本発明の光反射性異方性導電接着剤は、以上説明した光反射性絶縁粒子と導電粒子と熱硬化性樹脂組成物とを、常法に従って均一に混合することにより製造することができる。また、光反射性異方性導電接着フィルムとする場合には、それらをトルエン等の溶媒とともに分散混合し、剥離処理したPETフィルムに所期の厚さとなるように塗布し、約80℃程度の温度で乾燥すればよい。
本発明の光反射性異方性導電接着剤の反射特性は、発光素子の発光効率を向上させるために、光反射性異方性導電接着剤の硬化物の波長450nmの光に対する反射率(JIS K7105)が、少なくとも30%であることが望ましい。このような反射率とするためには、使用する光反射性絶縁粒子の反射特性や配合量、熱硬化性樹脂組成物の配合組成などを適宜調整すればよい。通常、反射特性の良好な光反射性絶縁粒子の配合量を増量すれば、反射率も増大する傾向がある。
次に、本発明の発光装置について図2を参照しながら説明する。発光装置200は、基板21上の接続端子22と、発光素子としてLED素子23のn電極24とp電極25とのそれぞれに形成された接続用のバンプ26との間に、前述の本発明の光反射性異方性導電接着剤を塗布し、基板21とLED素子23とがフリップチップ実装されている発光装置である。ここで、光反射性異方性導電接着剤の硬化物100は、光反射性絶縁粒子や導電粒子、好ましくは光反射性導電粒子10が熱硬化性樹脂組成物の硬化物11中に分散してなるものである。なお、必要に応じて、LED素子23の全体を覆うように透明モールド樹脂で封止してもよい。また、LED素子23に従来と同様に光反射層を設けてもよい。
従って、発光効率の低下を防止することができる。
窒素気流中、還流冷却管と磁気撹拌子とを備えた100ml三口フラスコに、29.82g(104.36mmol)の1−アリル−3,5−ジグリシジルイソシアヌレート(MADGIC、四国化成工業(株))と、5.11g(21.25mmol)の1,3,5,7−テトラメチルシクロテトラシロキサン(Gelest Inc.)とを投入し、混合物を80℃で均一に溶融するまで撹拌した。続いて、この溶融混合物に2%Karstedt白金触媒溶液(キシレン溶液)を以下の濃度となるように添加し、撹拌しながら140℃になるまで加熱し、溶融混合物の温度が140℃に到達してから、その温度を6時間保持して、1−アリル−3,5−ジグリシジルイソシアヌレートと1,3,5,7−テトラメチルシクロテトラシロキサンとを反応させた。
(側鎖型のジグリシジルイソシアヌリル変性ポリシロキサンの製造)
窒素気流中、還流冷却管と磁気撹拌子とを備えた1000ml三口フラスコに、235.21g(836.25mmol)の1−アリル−3,5−ジグリシジルイソシアヌレート(MADGIC、四国化成工業(株))と、125.00g(442.27mmol)の1,1,1,3,5,7,7,7−オクタメチルテトラシロキサン(東京化成工業(株))]とを投入し、混合物を80℃で均一に溶融するまで撹拌した。続いて、この溶融混合物に2%Karstedt白金触媒溶液(キシレン溶液)を表1の量[μL]で添加し、撹拌しながら140℃になるまで加熱し、溶融混合物の温度が140℃に到達してから、その温度を6時間保持して、1−アリル−3,5−ジグリシジルイソシアヌレートと1,1,1,3,5,7,7,7−オクタメチルテトラシロキサンとを反応させた。なお、反応時の白金触媒濃度の計算値を表1に示す。
表2に示す配合組成の成分を、エポキシ基/酸無水物の官能基数の比が1/1.1となるように、エポキシ化合物と酸無水物系硬化剤とを配合し、均一に混合することにより光反射性異方性導電接着剤を調製した。
得られた光反射性異方性導電接着剤のダイシェア強度を以下に説明するように測定した。また、光反射性異方性導電接着剤から光反射性絶縁粒子と導電粒子とを除いた残りの熱硬化性樹脂組成物について、以下に説明するように、耐熱試験と耐熱光試験とを行った。得られた結果を表3に示す。
金バンプ(高10μm、径80μm、ピッチ190μm)が形成された10μm厚の銀ベタ電極を有するLED用ガラスエポキシ基板(特注品、関西電子工業(株))に、径が4mmとなるように光反射性異方性導電接着剤を塗布し、そこへ0.3mm角のフリップチップ型LED素子(GM35R460G、昭和電工(株))を載せ、フリップチップ型LED素子が表側となるようにガラスエポキシ基板を80℃に保持されたホットプレートに置き、2分間加熱してLED素子をLED用ガラスエポキシ基板に仮固定した。このLED素子が仮固定されたLED用ガラスエポキシ基板を熱圧着装置に適用し、LED素子に80gf/chipの圧力を印加しながら230℃で15秒間熱圧着処理を行うことにより、LED用ガラスエポキシ基板にLED素子が実装されたLED装置を作成した。
1mm高さのスペーサが四隅に配置された2枚のアルミニウム平板(長100mm×幅50.0mm×厚0.500mm)で熱硬化性樹脂組成物を挟み、まず120℃で30分加熱し、続いて140℃で1時間加熱することにより硬化樹脂シートを作成した。
耐熱試験に供した硬化樹脂シートと同様の硬化樹脂シートを作成し、それを、温度120℃で光強度16mW/cm2に設定された熱光試験機(スーパーウインミニ、ダイプラ・ウィンテス(株);メタルハライドランプ使用)内に1000時間放置し、得られた硬化樹脂シートを、150℃に設定されたオーブン内に1000時間放置し、外観着色の有無を観察すると共に、放置前後の分光特性(L*、a*、b*)を、分光測色計(CM−3600d、コニカミノルタ(株))を用いて測定し、得られた測定値から色差(ΔE)を算出した。実用上、ΔEは30以下であることが望まれる。併せて耐熱光試験後の外観の着色の有無を目視観察し、着色が観察されなかった場合を良好「○」と評価し、観察された場合を不良「×」と評価した。
2 無機粒子
3 光反射層
4 熱可塑性樹脂
10、20 光反射性導電粒子
11 熱硬化性樹脂組成物の硬化物
21 基板
22 接続端子
23 LED素子
24 n電極
25 p電極
26 バンプ
100 光反射性異方性導電接着剤の硬化物
200 発光装置
Claims (14)
- 発光素子を配線板に異方性導電接続するために使用する光反射性異方性導電接着剤であって、熱硬化性樹脂組成物、導電粒子及び光反射性絶縁粒子を含有し、
熱硬化性樹脂組成物が、式(1)
で表されるジグリシジルイソシアヌリル変性環状ポリシロキサンと、エポキシ樹脂用硬化剤とを含有し、
式(1)の該ジグリシジルイソシアヌリル変性環状ポリシロキサンは、式(a)のハイドロジェン環状ポリシロキサンと、式(b)の1−アリル−3,5−ジグリシジルイソシアヌレートとを、無溶媒で均一に混合した後、20ppm以下の白金触媒の存在下で、無溶媒で、室温から150℃までの温度で、ハイドロシリレーション反応させることにより得られるものであり、
当該ジグリシジルイソシアヌリル変性環状ポリシロキサンの白金含有量が、20ppm以下である
ことを特徴とする光反射性異方性導電接着剤。
(式中、R、n、及びSiとOとを結ぶ円弧は、式(1)で説明したとおりである。) - Rがメチル基であり、nが4である請求項1記載の光反射性異方性導電接着剤。
- 熱硬化性樹脂組成物が、式(1)のジグリシジルイソシアヌリル変性環状ポリシロキサン100質量部に対し、エポキシ樹脂用硬化剤を50〜120質量部含有する請求項1又は2記載の光反射性異方性導電接着剤。
- エポキシ樹脂用硬化剤が、酸無水物系硬化剤である請求項1〜3のいずれかに記載の光反射性異方性導電接着剤。
- 熱硬化性樹脂組成物が、更にイミダゾール系硬化促進剤を含有する請求項4記載の光反射性異方性導電接着剤。
- 熱硬化性樹脂組成物が、酸無水物系硬化剤100質量部に対し、イミダゾール系硬化促進剤を0.20〜2.00質量部含有する請求項5記載の光反射性異方性導電接着剤。
- 光反射性絶縁粒子が、酸化チタン、窒化ホウ素、酸化亜鉛及び酸化アルミニウムからなる群より選択される少なくとも一種の無機粒子である請求項1〜6のいずれかに記載の光反射性異方性導電接着剤。
- 光反射性絶縁粒子の屈折率(JIS K7142)が、熱硬化性樹脂組成物の硬化物の屈折率(JIS K7142)よりも大きい請求項1〜7のいずれかに記載の光反射性異方性導電接着剤。
- 光反射性絶縁粒子が、鱗片状又は球状金属粒子の表面を絶縁性樹脂で被覆した樹脂被覆金属粒子である請求項1〜8のいずれかに記載の光反射性異方性導電接着剤。
- 光反射性異方性導電接着剤が、光反射性絶縁粒子を1〜50体積%で含有している請求項1〜9のいずれかに記載の光反射性異方性導電接着剤。
- 導電粒子が、金属材料で被覆されているコア粒子と、その表面に酸化チタン粒子、窒化ホウ素粒子、酸化亜鉛粒子又は酸化アルミニウム粒子から選択された少なくとも一種の無機粒子から形成された光反射層とからなる光反射性導電粒子である請求項1〜10のいずれかに記載の光反射性異方性導電接着剤。
- 熱硬化性樹脂組成物100質量部に対する光反射性導電粒子の配合量が、1〜100質量部である請求項11記載の光反射性異方性導電接着剤。
- 請求項1〜12のいずれかに記載の光反射性異方性導電接着剤を介して、発光素子がフリップチップ方式で配線板に実装されている発光装置。
- 発光素子が、発光ダイオードである請求項13記載の発光装置。
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JP5139857B2 (ja) * | 2008-03-27 | 2013-02-06 | 新日鉄住金化学株式会社 | エポキシシリコーン樹脂を含む硬化性樹脂組成物 |
JP5557324B2 (ja) * | 2010-09-01 | 2014-07-23 | 信越化学工業株式会社 | ダイボンド剤及び光半導体装置 |
WO2012124724A1 (ja) * | 2011-03-16 | 2012-09-20 | ソニーケミカル&インフォメーションデバイス株式会社 | 光反射性異方性導電接着剤及び発光装置 |
JP5958107B2 (ja) * | 2012-06-15 | 2016-07-27 | デクセリアルズ株式会社 | 光反射性異方性導電接着剤及び発光装置 |
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