JP6942718B2 - 3次元シリコン貫通配線(tsv)パッケージ用のアンダーフィルフィルム用の樹脂組成物及びその調製に有用な組成物 - Google Patents
3次元シリコン貫通配線(tsv)パッケージ用のアンダーフィルフィルム用の樹脂組成物及びその調製に有用な組成物 Download PDFInfo
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- JP6942718B2 JP6942718B2 JP2018544765A JP2018544765A JP6942718B2 JP 6942718 B2 JP6942718 B2 JP 6942718B2 JP 2018544765 A JP2018544765 A JP 2018544765A JP 2018544765 A JP2018544765 A JP 2018544765A JP 6942718 B2 JP6942718 B2 JP 6942718B2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 21
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Description
本発明によれば、以下:
(i)マレイミド、ナジイミド、又はイタコンイミド、
(ii)エポキシ樹脂、
(iii)強靭化剤、及び
(iv)充填材
を含むが、ただし、前記組成物は、アクリレート樹脂を実質的に含有せず;
ここで:
前記マレイミド、ナジイミド、又はイタコンイミドは、モノマー又はオリゴマーであり、かつ、ラジカル硬化してポリマーネットワークを形成することができ;
前記エポキシ樹脂は、硬化して3次元ポリマーネットワークとなることができる熱硬化性樹脂であり;
前記強靭化剤は、前記組成物の材料の脆性を低減し、かつその耐衝撃性を向上させ;かつ
前記充填材は、得られる組成物の熱膨張係数(CTE)を調節し;かつ
ここで、前記組成物は、硬化すると:
示差走査熱量計(DSC)オンセットが100℃〜205℃であり;
溶融粘度が200ポアズ〜40,000ポアズの範囲であり、かつ
Aresレオメーターによって、10Radの周波数で、10℃/分の昇温速度(ramp rate)で、直径1インチかつ1mm厚のサンプルを使用して測定されるゲル化温度が130℃〜180℃である、組成物が提供される。
mは、1〜15であり、
pは、0〜15であり、
各R2は、水素又は低級アルキル(C1−5など)から独立して選択され、そして
Jは、有機基又はオルガノシロキサン基、及びその2種以上の組み合わせを含む、一価又は多価の基である)
を有する化合物である。
−典型的には約6から最大約500個の範囲の炭素原子を有するヒドロカルビル又は置換ヒドロカルビル種であって、該ヒドロカルビル種は、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、アリール、アルキルアリール、アリールアルキル、アリールアルケニル、アルケニルアリール、アリールアルキニル、又はアルキニルアリールから選択されるが、ただし、Jが2以上の異なる種の組み合わせを含む場合のみ、Jはアリールであることができる;
−典型的には約6から最大約500個の炭素原子を有するヒドロカルビレン又は置換ヒドロカルビレン種であって、該ヒドロカルビレン種は、アルキレン、アルケニレン、アルキニレン、シクロアルキレン、シクロアルケニレン、アリーレン、アルキルアリーレン、アリールアルキレン、アリールアルケニレン、アルケニルアリーレン、アリールアルキニレン、又はアルキニルアリーレンから選択される、
−典型的には約6から最大約500個の範囲の炭素原子を有する複素環又は置換複素環種、
−ポリシロキサン、又は
−ポリシロキサン−ポリウレタンブロックコポリマー、並びに、
以下から選択されるリンカーを有する、上記の1又は複数の組み合わせ:共有結合、−O−、−S−、−NR−、−NR−C(O)−、−NR−C(O)−O−、−NR−C(O)−NR−、−S−C(O)−、−S−C(O)−O−、−S−C(O)−NR−、−O−S(O)2−、−O−S(O)2−O−、−O−S(O)2−NR−、−O−S(O)−、−O−S(O)−O−、−O−S(O)−NR−、−O−NR−C(O)−、−O−NR−C(O)−O−、−O−NR−C(O)−NR−、−NR−O−C(O)−、−NR−O−C(O)−O−、−NR−O−C(O)−NR−、−O−NR−C(S)−、−O−NR−C(S)−O−、−O−NR−C(S)−NR−、−NR−O−C(S)−、−NR−O−C(S)−O−、−NR−O−C(S)−NR−、−O−C(S)−、−O−C(S)−O−、−O−C(S)−NR−、−NR−C(S)−、−NR−C(S)−O−、−NR−C(S)−NR−、−S−S(O)2−、−S−S(O)2−O−、−S−S(O)2−NR−、−NR−O−S(O)−、−NR−O−S(O)−O−、−NR−O−S(O)−NR−、−NR−O−S(O)2−、−NR−O−S(O)2−O−、−NR−O−S(O)2−NR−、−O−NR−S(O)−、−O−NR−S(O)−O−、−O−NR−S(O)−NR−、−O−NR−S(O)2−O−、−O−NR−S(O)2−NR−、−O−NR−S(O)2−、−O−P(O)R2−、−S−P(O)R2−、又は−NR−P(O)R2−(式中、各Rは、独立して、水素、アルキル、又は置換アルキルである)。
(A)以下の構造に包含されるエポキシ成分:
Yは、存在しても、又は存在しなくてもよく、そしてYが存在する場合、Yは、直接結合、CH2、CH(CH3)2、C=O、又はSであり、
ここでのR1は、アルキル、アルケニル、ヒドロキシ、カルボキシ、及びハロゲンであり、そして
ここでのxは、1〜4である);
(B)以下の構造に包含されるエポキシ官能化アルコキシシラン:
R1は、オキシラン含有部分構造であり、そして
R2は、1〜10個の炭素原子を有する、アルキル若しくはアルコキシ置換アルキル、アリール、又はアラルキル基である);及び
(C)成分(A)と成分(B)との反応生成物。
R1は、オキシラン含有部分構造であり、その例としては、2−(エトキシメチル)オキシラン、2−(プロポキシメチル)オキシラン、2−(メトキシメチル)オキシラン、及び2−(3−メトキシプロピル)オキシランが挙げられ、そして
R2は、1〜10個の炭素原子を有する、アルキル若しくはアルコキシ置換アルキル、アリール、又はアラルキル基である)。
Yは、存在しても、又は存在しなくてもよく、そしてYが存在する場合、Yは、直接結合、CH2、CH(CH3)2、C=O、又はSであり、
R1は、アルキル、アルケニル、ヒドロキシ、カルボキシ、又はハロゲンであり、そして
xは、1〜4である)
が挙げられる。
Zは、−O−(CH2)3−O−Ph−CH2−Ph−O−(CH2−CH(OH)−CH2−O−Ph−CH2−Ph−O−)n−CH2−オキシランであり、そして
nは、約1〜4の範囲に入る)
を有する。
− 金属表面の酸化物と反応して、溶融金属の濡れを促進し、また
− 高温表面を被覆することによって酸素バリアとして作用して、その酸化を防止する。
少なくとも15重量%の前記エポキシ樹脂、
少なくとも1重量%の前記マレイミド、ナジイミド、又はイタコンイミド、
少なくとも5重量%の前記強靭化剤、及び
少なくとも40重量%の前記充填材
を含む。
少なくとも1重量%のフラクシング剤、及び/又は
少なくとも0.2重量%の接着促進剤
をさらに含んでもよい。
約5〜最大40重量%の範囲の前記エポキシ樹脂、
約1〜最大25重量%の範囲の前記マレイミド、ナジイミド、又はイタコンイミド、
約5〜最大25重量%の範囲の前記強靭化剤、及び
約10〜最大80重量%の範囲の前記充填材
を含む。
少なくとも1、最大約10重量%のフラクシング剤、及び/又は
少なくとも0.1、最大約2重量%の接着促進剤
をさらに含んでもよい。
Claims (16)
- 組成物であって:
(i)少なくとも1重量%〜最大25重量%の範囲のマレイミド、ナジイミド、又はイタコンイミド;
(ii)少なくとも1重量%〜最大20重量%の範囲のエポキシ樹脂;
(iii)少なくとも5重量%〜最大25重量%の範囲の強靭化剤;
(iv)少なくとも40重量%〜最大80重量%の範囲のシリカ;及び
ラジカル開始剤
を含むが、ただし、前記組成物は、アクリレート樹脂を実質的に含有せず;
ここで:
前記マレイミド、ナジイミド、又はイタコンイミドは、モノマー又はオリゴマーであり、かつ、ラジカル硬化してポリマーネットワークを形成することができ、
該マレイミド、ナジイミド、又はイタコンイミドは、それぞれ以下の構造:
mは、1〜15であり、
pは、0〜15であり、
各R 2 は、水素又はC 1−5 アルキルから独立して選択され、そして
Jは、有機基又はオルガノシロキサン基、及びそれらの2種以上の組み合わせを含む、一価又は多価の基である)
を有し;
前記エポキシ樹脂は、硬化して3次元ポリマーネットワークとなることができる熱硬化性樹脂であり、1又は複数のエポキシ基を有するポリマー骨格を含み;
前記強靭化剤は、前記組成物の材料の脆性を低減し、かつその耐衝撃性を向上させ、
該強靭化剤は、エピクロロヒドリンとビスフェノールAとの中〜高分子量熱可塑性ポリマーであり、該強靭化剤は、ポリヒドロキシルエーテルの構造を有し、かつ、末端ヒドロキシル基及びその骨格に沿った反復ヒドロキシル基を有するフェノキシ樹脂であり;かつ
前記シリカは、得られる組成物の熱膨張係数(CTE)を調節し;かつ
ここで、前記組成物は、硬化する時に:
示差走査熱量計(DSC)オンセットが100℃〜205℃である、組成物。 - DSCオンセット温度(℃)とDSCピーク温度(℃)との差であるデルタT(℃)が20℃未満である、請求項1に記載の組成物。
- 前記エポキシ樹脂が、ビスフェノールAエポキシ樹脂、ビスフェノールFエポキシ樹脂、ナフタレンエポキシ樹脂、ノボラックエポキシ樹脂、シロキサン−変性エポキシ樹脂、脂環式エポキシ樹脂、ビフェニルエポキシ樹脂、DCPDエポキシ樹脂、又は変性エポキシ樹脂、及びこれらの任意の2種以上の組み合わせから選択される、請求項1又は2に記載の組成物。
- Jが、以下から選択される一価又は多価の基である、請求項1〜6のいずれか1項に記載の組成物:
−典型的には6から最大500個の範囲の炭素原子を有するヒドロカルビル又は置換ヒドロカルビル種であって、該ヒドロカルビル種は、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、アリール、アルキルアリール、アリールアルキル、アリールアルケニル、アルケニルアリール、アリールアルキニル、又はアルキニルアリールから選択されるが、ただし、Jが2以上の異なる種の組み合わせを含む場合のみ、Jはアリールであることができる;
−典型的には6から最大500個の炭素原子を有するヒドロカルビレン又は置換ヒドロカルビレン種であって、該ヒドロカルビレン種は、アルキレン、アルケニレン、アルキニレン、シクロアルキレン、シクロアルケニレン、アリーレン、アルキルアリーレン、アリールアルキレン、アリールアルケニレン、アルケニルアリーレン、アリールアルキニレン、又はアルキニルアリーレンから選択される、
−典型的には6から最大500個の範囲の炭素原子を有する複素環又は置換複素環種、
−ポリシロキサン、又は
−ポリシロキサン−ポリウレタンブロックコポリマー、並びに、
以下から選択されるリンカーを有する、上記の1又は複数の組み合わせ:共有結合、−O−、−S−、−NR−、−NR−C(O)−、−NR−C(O)−O−、−NR−C(O)−NR−、−S−C(O)−、−S−C(O)−O−、−S−C(O)−NR−、−O−S(O)2−、−O−S(O)2−O−、−O−S(O)2−NR−、−O−S(O)−、−O−S(O)−O−、−O−S(O)−NR−、−O−NR−C(O)−、−O−NR−C(O)−O−、−O−NR−C(O)−NR−、−NR−O−C(O)−、−NR−O−C(O)−O−、−NR−O−C(O)−NR−、−O−NR−C(S)−、−O−NR−C(S)−O−、−O−NR−C(S)−NR−、−NR−O−C(S)−、−NR−O−C(S)−O−、−NR−O−C(S)−NR−、−O−C(S)−、−O−C(S)−O−、−O−C(S)−NR−、−NR−C(S)−、−NR−C(S)−O−、−NR−C(S)−NR−、−S−S(O)2−、−S−S(O)2−O−、−S−S(O)2−NR−、−NR−O−S(O)−、−NR−O−S(O)−O−、−NR−O−S(O)−NR−、−NR−O−S(O)2−、−NR−O−S(O)2−O−、−NR−O−S(O)2−NR−、−O−NR−S(O)−、−O−NR−S(O)−O−、−O−NR−S(O)−NR−、−O−NR−S(O)2−O−、−O−NR−S(O)2−NR−、−O−NR−S(O)2−、−O−P(O)R2−、−S−P(O)R2−、又は−NR−P(O)R2−(式中、各Rは、独立して、水素、アルキル、又は置換アルキルである) - Jが、オキシアルキル、チオアルキル、アミノアルキル、カルボキシアルキル、オキシアルケニル、チオアルケニル、アミノアルケニル、カルボキシアルケニル、オキシアルキニル、チオアルキニル、アミノアルキニル、カルボキシアルキニル、オキシシクロアルキル、チオシクロアルキル、アミノシクロアルキル、カルボキシシクロアルキル、オキシシクロアルケニル、チオシクロアルケニル、アミノシクロアルケニル、カルボキシシクロアルケニル、複素環、オキシ複素環、チオ複素環、アミノ複素環、カルボキシ複素環、オキシアリール、チオアリール、アミノアリール、カルボキシアリール、ヘテロアリール、オキシヘテロアリール、チオヘテロアリール、アミノヘテロアリール、カルボキシヘテロアリール、オキシアルキルアリール、チオアルキルアリール、アミノアルキルアリール、カルボキシアルキルアリール、オキシアリールアルキル、チオアリールアルキル、アミノアリールアルキル、カルボキシアリールアルキル、オキシアリールアルケニル、チオアリールアルケニル、アミノアリールアルケニル、カルボキシアリールアルケニル、オキシアルケニルアリール、チオアルケニルアリール、アミノアルケニルアリール、カルボキシアルケニルアリール、オキシアリールアルキニル、チオアリールアルキニル、アミノアリールアルキニル、カルボキシアリールアルキニル、オキシアルキニルアリール、チオアルキニルアリール、アミノアルキニルアリール、又はカルボキシアルキニルアリール、オキシアルキレン、チオアルキレン、アミノアルキレン、カルボキシアルキレン、オキシアルケニレン、チオアルケニレン、アミノアルケニレン、カルボキシアルケニレン、オキシアルキニレン、チオアルキニレン、アミノアルキニレン、カルボキシアルキニレン、オキシシクロアルキレン、チオシクロアルキレン、アミノシクロアルキレン、カルボキシシクロアルキレン、オキシシクロアルケニレン、チオシクロアルケニレン、アミノシクロアルケニレン、カルボキシシクロアルケニレン、オキシアリーレン、チオアリーレン、アミノアリーレン、カルボキシアリーレン、オキシアルキルアリーレン、チオアルキルアリーレン、アミノアルキルアリーレン、カルボキシアルキルアリーレン、オキシアリールアルキレン、チオアリールアルキレン、アミノアリールアルキレン、カルボキシアリールアルキレン、オキシアリールアルケニレン、チオアリールアルケニレン、アミノアリールアルケニレン、カルボキシアリールアルケニレン、オキシアルケニルアリーレン、チオアルケニルアリーレン、アミノアルケニルアリーレン、カルボキシアルケニルアリーレン、オキシアリールアルキニレン、チオアリールアルキニレン、アミノアリールアルキニレン、カルボキシアリールアルキニレン、オキシアルキニルアリーレン、チオアルキニルアリーレン、アミノアルキニルアリーレン、カルボキシアルキニルアリーレン、ヘテロアリーレン、オキシヘテロアリーレン、チオヘテロアリーレン、アミノヘテロアリーレン、カルボキシヘテロアリーレン、ヘテロ原子含有二価若しくは多価環状部分構造、オキシヘテロ原子含有二価若しくは多価環状部分構造、チオヘテロ原子含有二価若しくは多価環状部分構造、アミノヘテロ原子含有二価若しくは多価環状部分構造、又はカルボキシヘテロ原子含有二価若しくは多価環状部分構造である、請求項1〜6のいずれか1項に記載の組成物。
- シアネートエステル樹脂、ベンゾオキサジン、芳香族エステル、芳香族アルケン、芳香族アルキン、芳香族ニトリル、又はこれらの任意の2種以上の組み合わせをさらに含む、請求項1〜8のいずれか1項に記載の組成物。
- 少なくとも1重量%のフラクシング剤、及び/又は
少なくとも0.1重量%の接着促進剤
のうちの1又は複数をさらに含む、請求項1〜9のいずれか1項に記載の組成物。 - シリカが、平均粒径が0.1μm以上1μm未満のシリカと0.1μm未満のシリカとを含む、請求項1〜10のいずれか1項に記載の組成物。
- (i)前記マレイミド、ナジイミド、又はイタコンイミド;
(ii)前記エポキシ樹脂;
(iii)前記強靭化剤;
(iv)前記シリカ;
ラジカル開始剤;
フラクシング剤;
シランカップリング剤;及び
任意にイミダゾール系硬化剤
からなる、請求項1〜11のいずれか1項に記載の組成物。 - 請求項1〜12のいずれか1項に記載の組成物の硬化の反応生成物を含むアンダーフィルフィルム。
- アンダーフィルフィルムの調製方法であって、前記方法は、請求項1〜12のいずれか1項に記載の組成物を、好適な基板に塗布した後に硬化させることを含む、方法。
- 好適な基板に接着された請求項13に記載のアンダーフィルフィルムを備えた物品。
- 前記物品が、フリップチップパッケージ、スタックダイ、ハイブリッドメモリキューブ、又はTSVデバイスである、請求項15に記載の物品。
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PCT/US2016/061098 WO2017087228A1 (en) | 2015-11-17 | 2016-11-09 | Resin compositions for underfill film for three dimensional through silica via (tsv) packages and compositions useful for the preparation thereof |
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KR (1) | KR20180083873A (ja) |
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EP0812340A1 (en) * | 1995-12-27 | 1997-12-17 | Hexcel Corporation | Epoxy resin(s) with curing agent and toughener |
US5717034A (en) | 1996-07-29 | 1998-02-10 | Quantum Materials, Inc. | Perfluorinated hydrocarbon polymer-filled adhesive formulations and uses therefor |
JP2004307859A (ja) * | 2003-04-05 | 2004-11-04 | Rohm & Haas Electronic Materials Llc | 電子デバイス製造 |
US7378523B2 (en) | 2005-08-25 | 2008-05-27 | National Starch And Chemical Investment Holding Corporation | Quinolinols as fluxing and accelerating agents for underfill compositions |
US20070152311A1 (en) * | 2005-12-30 | 2007-07-05 | Saikumar Jayaraman | Chip-packaging compositions including bis-maleimides, packages made therewith, and methods of assembling same |
US7314778B2 (en) * | 2005-12-30 | 2008-01-01 | Intel Corporation | Wafer-level processing of chip-packaging compositions including bis-maleimides |
US20100007018A1 (en) * | 2006-12-08 | 2010-01-14 | Derek Wyatt | Process for coating a bumped semiconductor wafer |
KR20090101336A (ko) * | 2006-12-08 | 2009-09-25 | 헨켈 아게 운트 코. 카게아아 | 범프 부착 반도체 웨이퍼의 코팅 방법 |
US8586650B2 (en) * | 2007-09-14 | 2013-11-19 | Henkel US IP LLC | Thermally conductive composition |
JP2009155399A (ja) * | 2007-12-25 | 2009-07-16 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物並びにこれを用いたプリプレグ及び積層板 |
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JP2010229227A (ja) * | 2009-03-26 | 2010-10-14 | Sekisui Chem Co Ltd | エポキシ樹脂組成物、シート状成形体、プリプレグ、硬化体及び積層板 |
TWI540170B (zh) * | 2009-12-14 | 2016-07-01 | Ajinomoto Kk | Resin composition |
CN101857789B (zh) * | 2010-05-26 | 2013-01-09 | 上海大学 | 光电器件封装用环氧倍半硅氧烷/环氧树脂杂化胶及其制备方法 |
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WO2015102978A1 (en) * | 2014-01-02 | 2015-07-09 | Henkel IP & Holding GmbH | Film containing nano-particulate filler |
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WO2017087228A1 (en) | 2017-05-26 |
KR20180083873A (ko) | 2018-07-23 |
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