JP2007522672A - ハイブリッドオキサゾリン化合物で基板に取り付けられた半導体ダイ - Google Patents

ハイブリッドオキサゾリン化合物で基板に取り付けられた半導体ダイ Download PDF

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JP2007522672A
JP2007522672A JP2006553103A JP2006553103A JP2007522672A JP 2007522672 A JP2007522672 A JP 2007522672A JP 2006553103 A JP2006553103 A JP 2006553103A JP 2006553103 A JP2006553103 A JP 2006553103A JP 2007522672 A JP2007522672 A JP 2007522672A
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functional group
group
electron
oxazoline
compound
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Inventor
ムサ，オサマ・エム
サン，ルシ
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ナショナル スターチ アンド ケミカル インベストメント ホールディング コーポレイション
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Publication of JP2007522672A publication Critical patent/JP2007522672A/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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Abstract

オキサゾリン官能基及び電子受容性又は電子供与性官能基を含む化合物を含む組成物で基板に取り付けられた半導体ダイのアセンブリを作製する。電子供与性官能基としてはスチレン基、シンナミル基及びビニルエーテル基が挙げられる。電子受容性官能基としてはマレイミド基、アクリレート基、フマレート基及びマレエート基が挙げられる。化合物の例として下記構造式（Ｉ）のものが挙げられる。
【化１】

Description

発明の詳細な説明
発明の分野
本発明はオキサゾリン官能基と電子受容性又は電子供与性官能基との両者を有する化合物を含む硬化性又は硬化された組成物で基板に取り付けられた半導体ダイのアセンブリに関する。
発明の背景
半導体パッケージ及びマイクロ電子デバイスの製造のために、組み立て工程において接着組成物及び封止組成物を使用することが必要である。代表的な組成物としては、ラジカル硬化性組成物、電子供与／電子受容系などが挙げられる。これらは特定の用途において常に最大限の性能を発揮するわけではなく、半導体製造産業において未だ高性能の材料が求められている。
発明の概要
本発明は、オキサゾリン官能基及び電子受容性又は電子供与性官能基を含む化合物を含む組成物で基板に取り付けられ又は支持された半導体ダイのアセンブリに関する。この組成物は硬化性の状態で施され、in situで硬化される。電子供与性官能基としてはスチレン基、シンナミル基及びビニルエーテル基が挙げられる。電子受容性官能基としてはマレイミド基、アクリレート基、フマレート基及びマレエート基が挙げられる。
発明の詳細な記述
オキサゾリン類は窒素原子、酸素原子及び１つの二重結合を有する５員複素環化合物である。この二重結合は３つの位置の内の一つに位置することができるので、３つの異なるオキサゾリン環：２−オキサゾリン（最も一般的）、３−オキサゾリン及び４−オキサゾリン、の存在を可能にしている。オキサゾリン類はカチオン性開環単独重合を起こし、電子受容／電子供与系はフリーラジカル重合を起こす。従って、１分子あたり少なくとも一つのオキサゾリン基と一つの電子供与性又は電子受容性官能基を有する化合物は熱と放射線の両方で二種類の硬化反応を起こすことができる。
ここで使用する組成物はオキサゾリン及び電子受容性又は電子供与性官能基を有する化合物、硬化剤及び充填材を含む。電子受容性官能基が存在する組成物では硬化剤は場合によって採用される。組成物はブレンドし又はミリングして調製されたペーストや、当業者に知られている標準フィルム作製技術によって作製されたフィルムとすることができる。
組成物はオキサゾリン及び電子受容性又は電子供与性官能基を有する化合物から主になるが、オキサゾリン及び電子受容性又は電子供与性官能基を有する化合物は１以上の他の硬化性樹脂に対する接着促進剤としてより少ない量で使用されることもできる。接着促進剤として使用される場合、組成物中における使用量は有効量であり、配合物の０．００５〜２０．０重量％の範囲とすることができる。
接着促進剤として使用する場合、その主成分は例えばエポキシ、ビニルエーテル、チオレン、シンナミル及びスチレン系出発化合物から誘導される樹脂、フマレート、マレエート、アクリレート、マレイミド、シアネートエステル、オキセタン、フェノール、アミノ樹脂、プロパルギルエーテル、ベンゾシクロブテン及びベンゾオキサジンなどを含む他の好適な硬化性樹脂である。
好適な硬化剤は、組成物を硬化するために有効量で存在する熱開始剤及び光開始剤である。一般に、それらの量は組成物中の総有機材料（即ち、全ての無機充填材を除く）の０．１重量％〜３０重量％、好ましくは１重量％〜２０重量％の範囲である。
好ましいラジカル開始剤としては、ブチルペルオクトエート、ジクミルペルオキシドなどのペルオキシド類、２，２’−アゾビス（２−メチル−プロパンニトリル）、２，２’−アゾビス（２−メチル−ブタンニトリル）などのアゾ化合物などが挙げられる。好ましいカチオン性開始剤としては、ヨードニウム、オキソニウム、スルホニウム、スルホキソニウム、種々の他のオニウム塩などが挙げられる。他の好適なカチオン性開始剤としては、アリールスルホネートエステル（例えば、メチル−ｐ−トルエンスルホネート）、メチルトリフルオロメタンスルホネートなどのルイス酸触媒及びアルキル化剤などが挙げられる。光開始剤の好適なシリーズは、Ciba Speciality ChemicalsによってIrgacure又はRhodorsil 2074の商標で販売されている。いくつかの配合物において熱開始剤及び光開始剤の両方を好ましく用いることができる。その硬化プロセスは照射後加熱又は加熱後照射のいずれかによって開始することができる。
硬化性組成物は６０℃〜２５０℃の温度範囲内で硬化し、硬化反応は３秒〜３時間の範囲内で行う。実際の硬化プロファイルはその成分により変化し、作業者の過度の実験なしに決定することができる。
好適な充填材は導電性又は非導電性であり得る。導電性充填材としては、カーボンブラック、グラファイト、金、銀、銅、白金、パラジウム、ニッケル、アルミニウム、炭化珪素、窒化ホウ素、ダイアモンド、アルミナなどが挙げられる。非導電性充填材としては、バーミキュライト、マイカ、ウォラストナイト、炭酸カルシウム、チタニア、砂、ガラス、フューズドシリカ（fused silica）、フュームドシリカ（fumed silica）、硫酸バリウム及びハロゲン化エチレンポリマー（例えば、テトラフルオロエチレン、トリフルオロエチレン、ビニリデンフルオライド、ビニルフルオライド、ビニリデンクロライド、ビニルクロライド）の粒子などが挙げられる。一般に充填材は配合物の２０重量％〜９０重量％の量で存在する。
これら組成物はダイ及び基板の間のアンダーフィルとして基板に半導体ダイを取り付けるためあるいは半導体ダイを支持するために有用である。典型的な基板は、例えば、銅、銀、金、ニッケル、合金（４２Ｆｅ／５８Ｎｉ合金など）、銀でコートした銅、パラジウムでコートした銅などの金属；例えば、ポリイミド、ポリアミド、ポリエステルなどの有機材料；セラミック；複合材又は積層体（印刷配線基板など）から作製される。
代表的なダイ取り付け操作において、ペースト状又はフィルム状の接着材がリードフレームのセンターパドルなどの基板上に置かれ、シリコンダイをその接着材に熱及び圧力をかけて接触させる。正確なプロセス及びプロセスのパラメータは操作ごとに異なってもよい。これらのパラメータ及びプロセスは当業者に知られており、本発明の一部を構成しない。
代表的なアンダーフィル操作において、金属又はポリマーのソルダーを使用して、ダイ上の電気端子と基板上の対応する電気端子との間に接続が形成される。ソルダーのバンプが基板の端子上に置かれ、その端子は整列され、接触され、得られたアセンブリが加熱されてソルダーが再流動する。ダイと基板との間に隙間が形成され、その隙間はポリマーの封止材又はアンダーフィルで充填されて相互接続が強化される。アンダーフィルのためのプロセスにはいくつかのバリエーションがあり、例えば、ソルダーの再流動後あるいはソルダーの再流動と同時にアンダーフィル封止を行うことができる。これらのプロセスは当業者に知られており、本発明の一部を構成しない。
本発明の要旨は半導体ダイを基板に取り付け又は支持させるためのダイ取り付け又はアンダーフィル封止材としてオキサゾリン化合物を使用することである。
オキサゾリン化合物を合成する種々の経路が以下の合成経路を参照することにより考えられる。例えば、
Figure 2007522672
のスチレン及びオキサゾリン官能基の両方を有する化合物を調製するためには、Zerrouki, A. Ainser, A. Arsac, N.Mignard及びB.Marculescu, Polymer Bulletin, 42, 535, 1999の手順が使用できる。はじめにビニルベンジルクロライドをシアン化ナトリウムと反応させ、シアン化ビニルベンジルを得、その後それをエタノールアミンと反応させビニルベンジルオキサゾリンを得る。
例えば、
Figure 2007522672
のマレイミド及びオキサゾリン官能基の両方を有する化合物を調製するためには、無水マレイン酸(アセトニトリル中)を６−アミノカプロン酸（酢酸中）と反応させてアミック酸付加体を得る。この付加体を脱水して閉環させ、マレイミドを形成する。この反応の手順は当業界で知られている。生成物である６−マレイミドカプロン酸は、その後２−（３−ヒドロキシ−２−プロピル）−２−オキサゾリン（８０℃に加熱したトルエン中）と、触媒量の硫酸で反応させて、ワークアップし、生成物を単離する。
例えば、
Figure 2007522672
のシンナミル及びオキサゾリン官能基の両方を有する化合物を調製するためには、過剰量の５０％NaOH及び触媒量の硫酸水素テトラブチルアンモニウム中の２−（３−ヒドロキシ−２−プロピル）−２−オキサゾリンをトルエン中のシンナミルクロライドとはじめ５３℃で反応させ、その後７５℃で数時間反応させる。反応液を室温まで放冷し、有機層を抽出し、ブラインで３回洗浄する。単離した有機層はMgSO4で乾燥し、ろ過し、溶媒を減圧下除去して生成物を得る。
例えば、
Figure 2007522672
のスチレン及びオキサゾリン官能基の両方を有する化合物を調製するためには、３−イソプロペニル−α，α−ジメチルベンジルイソシアネート（ｍ−ＴＭＩ）及び２−（３−ヒドロキシ−２−プロピル）−２−オキサゾリンをトルエンに溶解し、窒素下、触媒量のジブチル錫ジラウレートと６０℃で数時間反応させる。反応液を室温まで放冷し、溶媒を減圧下除去して生成物を得る。
例えば、
Figure 2007522672
のアクリレート及びオキサゾリン官能基の両方を有する化合物を調製するためには、２−（３−ヒドロキシ−２−プロピル）−２−オキサゾリン及びトリエチルアミンを乾燥塩化メチレン中で０℃で混合する。乾燥塩化メチレン中に溶解した適切な当量のアクリロイルクロライドを注意深く加え、その混合物を数時間反応させる。溶媒を留去し、粗生成物をへキサン／酢酸エチルの勾配を使用してカラムクロマトグラフィーにより精製する。
例えば、
Figure 2007522672
のビニルエーテル及びオキサゾリン官能基の両方を有する化合物を調製するためには、過剰量の５０％NaOH及び触媒量の硫酸水素テトラブチルアンモニウム中の２−（３−ヒドロキシ−２−プロピル）−２−オキサゾリンをトルエン中の２−クロロエチルビニルエーテルとはじめ５３℃で反応させ、その後７５℃で数時間反応させる。反応液を室温まで放冷し、有機層を抽出し、ブラインで３回洗浄する。単離した有機層はMgSO4で乾燥し、ろ過し、溶媒を減圧下除去して生成物を得る。
例えば、
Figure 2007522672
のマレエート及びオキサゾリン官能基の両方を有する化合物を調製するためには、２−イソプロペニル−２−オキサゾリン及び２−メルカプトエタノールをトルエン中で７０℃で反応させる。トルエン中のアゾジイソブチロニトリル(AIBN)の溶液をその混合物に加え、反応を７０℃で数時間続ける。２−イソプロペニル−２−オキサゾリン／２−メルカプトエタノール付加体を減圧下溶媒を除去後に得る。この２−イソプロペニル−２−オキサゾリン／２−メルカプトエタノール付加体はその後窒素下でジメトキシエタン３００mＬ中の無水マレイン酸と７０℃で１時間反応させる。冷却後、反応液をヘプタンに注ぐ。得られた生成物を減圧下４０℃で２４時間乾燥する。

Claims (10)

  1. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物を含む組成物で基板に取り付けられた半導体ダイのアセンブリ。
  2. 電子供与性官能基がスチレン基、シンナミル基及びビニルエーテル基からなる群から選ばれる、請求項１に記載のアセンブリ。
  3. 電子受容性官能基がマレイミド基、アクリレート基、フマレート基及びマレエート基からなる群から選ばれる、請求項１に記載のアセンブリ。
  4. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子供与性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  5. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子受容性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  6. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子供与性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  7. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子供与性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  8. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子受容性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  9. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子供与性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
  10. オキサゾリン官能基及び電子受容性又は電子供与性官能基を有する化合物が電子受容性官能基を含み、下記構造：
    Figure 2007522672
     を有する、請求項１に記載のアセンブリ。
JP2006553103A 2004-02-17 2004-02-17 ハイブリッドオキサゾリン化合物で基板に取り付けられた半導体ダイ Pending JP2007522672A (ja)

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