JP2016518511A - ポリイミド及びポリアミド酸エステルポリマーを製造する改良されたプロセス - Google Patents
ポリイミド及びポリアミド酸エステルポリマーを製造する改良されたプロセス Download PDFInfo
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- JP2016518511A JP2016518511A JP2016514154A JP2016514154A JP2016518511A JP 2016518511 A JP2016518511 A JP 2016518511A JP 2016514154 A JP2016514154 A JP 2016514154A JP 2016514154 A JP2016514154 A JP 2016514154A JP 2016518511 A JP2016518511 A JP 2016518511A
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
Description
本願は、2013年5月17日に出願された米国特許仮出願第61/824,529号の優先権を主張し、その内容は、その全体を参照することによって本明細書に援用される。
いくつかの実施形態では、少なくとも一つの極性非プロトン性重合溶媒中にポリイミド又はポリアミド酸エステルを含有する有機溶液を提供する工程は、少なくとも一つの極性非プロトン性重合溶媒中で、適切な出発試薬を使用してポリイミド又はポリアミド酸エステルを形成することにより、そのようにして得られたポリイミド又はポリアミド酸エステルを分離することなく実行することができる。
工程1における、重合、イミド化、及び/又はエステル化反応の後、工程1において形成された反応混合物は、少なくとも一つ(例えば二つ、三つ、又はそれ以上)の精製溶媒を用いて希釈して、ポリイミド又はポリアミド酸エステルを含有する、希釈された有機溶液を形成することができる。精製溶媒は、溶媒、又は二つ以上の溶媒の組み合わせであってもよく、これらの溶媒は、極性非プロトン性重合溶媒よりも極性が低く且つ重合溶媒よりも25℃での水溶性が低い。理論に拘束されるのを望むものではないが、精製溶媒の二つの鍵となる機能は、(1)溶液中にPI又はPAEポリマーを維持すること、及び(2)水及び/又は添加剤を含有する水溶液との二相混合物を形成することであると考えられる。本開示の文脈では、二相混合物は、明確に区別できる分離した二相(例えば、明確に区別できる二つの液相)を含有する混合物を指す。
PI又はPAEポリマーを精製溶媒中で希釈したら、この希釈された有機溶液を、水及び/又は添加剤(例えば、酸又は塩基)を含有する水溶液を用いた洗浄に付して、洗浄された有機溶液を得ることができる。理論に拘束されるのを望むものではないが、この工程は、重合溶媒、重合副生成物、触媒、残留モノマー、及び他の不純物を、ポリマー含有有機相から水相へ除去することにより、PI又はPAEポリマーを精製することができると考えられる。
PI又はPAEポリマーを含有する有機溶液を、水性媒質(例えば水)により洗浄した後には、有機溶液中の精製溶媒の少なくとも一部(例えば、実質的にすべて)は、除去されて、又は少なくとも一つの分離溶媒と交換されて、精製されたPI又はPAEポリマーを含有する溶液(すなわち、精製されたポリマー溶液)を得ることができる。
a)本明細書に記載の精製されたPI又はPAEポリマー溶液を基体に塗布し、塗膜付き基体を形成する工程、
b)塗膜付き基体を(例えば、第1のベーク工程において温度T1で)ベークして、精製されたPI又はPAEポリマー溶液中の溶媒の少なくとも一部(例えば実質的にすべて)を除去する工程;及び
c)塗膜を前記基体から(例えば、機械的な力、又は化学処理を適用することにより)剥離して、自立膜を得る工程、
を含むことができる。
6FDA: 2,2’−ビス(3,4−ジカルボキシフェニル)ヘキサフルオロプロパン二無水物
DAPI: 4,4’−[1,4−フェニレン−ビス(1−メチルエチリデン)]ビスアニリン
BTDA: 3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物
PMDA: ピロメリット酸二無水物
ODA: 4,4’−オキシジアニリン
ODPA: 4,4’−オキシジフタル酸無水物
DAM: 1,3−ジアミノメシチレン
HEMA: ヒドロキシエチルメタクリレート
NMP: N−メチルピロリジノン
GBL: ガンマ−ブチロラクトン
DMSO: ジメチルスルホキシド
PIポリマーの例を、一つのジアミン及び一つの二無水物を使用して調製し、この場合には分離溶媒(すなわちラクトン)は、精製溶媒(すなわち、エステルとケトン)とは異なっていた。水の、使用したポリマーに対する比は、46:1であった。
エンドキャップされたPIポリマーの例を、一つのジアミンと一つの二無水物を使用して調製し、この場合には分離溶媒(すなわちラクトン)は、精製溶媒(すなわちエステルとケトン)とは異なっていた。洗浄水溶液の、使用したポリマーに対する比は、48:1であった。
エンドキャップされたPIポリマーの例を、一つのジアミンと一つの二無水物を使用して調製し、この場合には分離溶媒(すなわち、ラクトン)は、精製溶媒(すなわちエステルとケトン)とは異なっていた。水の、使用したポリマーに対する比は、48:1であった。
エンドキャップされたPIポリマーの例を、二つのジアミンと一つの二無水物を使用して調製し、この場合には分離溶媒(すなわちケトン)は、精製溶媒(すなわちケトンと芳香族炭化水素)の一方と同一であった。水の、使用したポリマーに対する比は、21:1であった。
エンドキャップされたPIポリマーの例を、二つのジアミンと二つの二無水物を使用して調製し、この場合には分離溶媒(すなわちケトン)は、精製溶媒(すなわちケトンと芳香族炭化水素)の一方と同一であった。水の、使用したポリマーに対する比は、20:1であった。
エンドキャップされていないPIポリマーの例を、一つのジアミンと一つの二無水物を使用して調製し、この場合には分離溶媒(すなわちラクトン)は、精製溶媒(すなわちエステルとケトン)とは異なっていた。水の、使用したポリマーに対する比は、46:1であった。
PAEポリマーの例を、一つのジアミンと一つの二無水物を使用して調製し、この場合には分離溶媒(すなわち、ラクトンとスルホキシド)は、精製溶媒(すなわちエステルとケトン)とは異なっていた。水の、使用したポリマーに対する比は、69:1であった。
実施例7において製造した反応混合物の一部を、以下の従来方法により精製した。水の、使用したポリマーに対する比は、492:1であった。
実施例4において製造した反応混合物の一部を、以下の従来方法により精製した。
実施例6において製造した反応混合物の一部を、以下の従来方法により精製した。
実施例1において得られた100部のポリマー溶液と、1.5部の(3−トリエトキシシリル)プロピルコハク酸無水物を含む混合物を調製し、1.0ミクロンのフィルターを使用することによりろ過する。組成物をシリコンウェーハ上にスピン塗布し、厚さ10ミクロンの塗膜を形成する。塗布済みウェーハは、120℃で3分間、ベークする。塗膜の欠陥と膜の亀裂は、光学顕微鏡によりチェックする。
熱硬化性組成物を、実施例2において得られた100部のポリマー溶液、8.5部のジペンタエリスリトールヘキサキス(3−メルカプトプロピオネート)、0.5部のN−メチルジシクロヘキシルアミン、及び4.5部のガンマ−グリシドキシプロピルトリエトキシシランを混合することにより調製する。組成物を、1.0ミクロンのフィルターを使用することによりろ過する。組成物をシリコンウェーハ上にスピン塗布して、厚さ10ミクロンの塗膜を形成する。塗布済みウェーハを、125℃で5分間、ベークする。塗膜の欠陥と膜の亀裂は、光学顕微鏡によりチェックする。膜を、N2雰囲気下、対流式オーブン中、200℃で1時間、加熱する。得られた膜を、膜の欠陥に関して光学顕微鏡により再びチェックする。膜を各種溶媒(PGMEA、GBL、及びアセトン)に浸漬して、その溶媒耐性を評価する。
熱硬化性組成物を、実施例3において得られた100部のポリマー溶液、7部のトリメチロールプロパントリス(4−スルファニルシクロヘキサンカルボキシレート)、0.7部のトリエチルアミン、及び3部の(3−トリエトキシシリルプロピル)−t−ブチルカルバメートを混合することにより調製する。組成物を、1.0ミクロンのフィルターを使用することによりろ過する。組成物をシリコンウェーハ上にスピン塗布し、厚さ12ミクロンの塗膜を形成する。塗布済みウェーハを、130℃で4分間、ベークする。塗膜の欠陥と膜の亀裂を、光学顕微鏡によりチェックする。膜を、N2雰囲気下、対流式オーブン中、220℃で1時間、加熱する。得られた膜を、膜の欠陥に関して光学顕微鏡により再びチェックする。膜を各種溶媒(PGMEA、GBL、及びアセトン)に浸漬して、その溶媒耐性を評価する。
感光性組成物を、実施例4において得られた100部のポリマー溶液、20部のテトラエチレングリコールジメタクリレート、及び1.5部のNCI−831(商品名、株式会社ADEKAから入手可能)を混合することにより調製する。組成物を、0.2ミクロンのフィルターを使用することによりろ過し、シリコンウェーハ上にスピン塗布して、厚さ約9ミクロンの塗膜を形成する。塗布済みウェーハを、105℃で3分間、ベークする。感光性ポリイミド膜を、広帯域UV露光装置(Carl Suss MA−56)を用い、露光用の所望のパターンを有するマスクを通して露光する。
Claims (30)
- 少なくとも一つの極性非プロトン性重合溶媒中にポリイミド又はポリアミド酸エステルを含有する有機溶液を提供すること;
前記少なくとも一つの重合溶媒よりも極性が低く且つ前記少なくとも一つの重合溶媒よりも25℃での水溶性が低い少なくとも一つの精製溶媒を前記有機溶液に加えて、希釈された有機溶液を形成すること;
前記希釈された有機溶液を、水又は水溶液を用いて洗浄して、洗浄された有機溶液を得ること;及び
前記洗浄された有機溶液中の前記少なくとも一つの精製溶媒の少なくとも一部を除去して、精製されたポリイミド又はポリアミド酸エステルを含有する溶液を得ること、
を含む、ポリマーを精製するプロセス。 - 前記少なくとも一つの重合溶媒が、ジメチルホルムアミド、ジメチルアセトアミド、N−ホルミルモルホリン、N−メチルピロリジノン、N−エチルピロリジノン、ジメチルスルホキシド、ガンマ−ブチロラクトン、ヘキサメチルリン酸トリアミド、テトラヒドロフラン、メチルテトラヒドロフラン、1,4−ジオキサン、又はそれらの混合物を含む、請求項1に記載のプロセス。
- 前記少なくとも一つの重合溶媒が、少なくとも一つの水混和性溶媒を含む、請求項1に記載のプロセス。
- 前記少なくとも一つの精製溶媒が、エステル、エーテル、ケトン、少なくとも一つのハライドにより置換されていてもよい炭化水素、又はそれらの混合物を含む、請求項1に記載のプロセス。
- 前記少なくとも一つの精製溶媒が、酢酸メチル、酢酸エチル、酢酸n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸イソブチル、酢酸sec−ブチル、酢酸シクロへキシル、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート、酢酸テトラヒドロフルフリル、ギ酸プロピル、ギ酸ブチル、ギ酸イソブチル、ギ酸ペンチル、ε−カプロラクトン、ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジシクロヘキシルエーテル、シクロペンチルメチルエーテル、メチルtert−ブチルエーテル、エチルtert−ブチルエーテル、アニソール、フェニルエチルエーテル、ジフェニルエーテル、1,2−ジメトキシプロパン、1,2−ジメトキシエタン、2−ブタノン、2−ペンタノン、3−ペンタノン、メチルイソブチルケトン、エチルイソブチルケトン、メチルイソプロピルケトン、シクロペンタノン、シクロヘキサノン、アセトフェノン、イソホロン、メシチルオキシド、ベンゼン、トルエン、キシレン、エチルベンゼン、クロロベンゼン、1,2−ジクロロベンゼン、α,α,α−トリフルオロトルエン、ペンタン、ヘキサン、へプタン、オクタン、シクロヘキサン、メチルシクロヘキサン、シクロヘキセン、又はそれらの混合物を含む、請求項4に記載のプロセス。
- 前記少なくとも一つの精製溶媒が、少なくとも一つの水非混和性溶媒を含む、請求項1に記載のプロセス。
- 少なくとも一つの精製溶媒を加えることが、前記少なくとも一つの精製溶媒よりも水溶性が高い少なくとも一つの精製共溶媒を加えることをさらに含む、請求項1に記載のプロセス。
- 前記少なくとも一つの精製共溶媒が、アセトン、ガンマ−ブチロラクトン、フラン、テトラヒドロフラン、メチルテトラヒドロフラン、テトラヒドロフルフリルメチルエーテル、1,4−ジオキサン、又はそれらの混合物を含む、請求項7に記載のプロセス。
- 前記少なくとも一つの精製共溶媒が、少なくとも一つの水混和性溶媒を含む、請求項8に記載のプロセス。
- 前記水溶液が添加剤を含む、請求項1に記載のプロセス。
- 前記希釈された有機溶液を洗浄することが、水又は水溶液を前記希釈された有機溶液に加えることを含む、請求項1に記載のプロセス。
- 前記希釈された有機溶液を洗浄することが、有機相及び水相を有する混合物を形成することをさらに含む、請求項11に記載のプロセス。
- 前記希釈された有機溶液を洗浄することが、前記水相を除去することをさらに含む、請求項12に記載のプロセス。
- 前記希釈された溶液を洗浄することにより、前記希釈された有機溶液中の前記少なくとも一つの重合溶媒又は別の不純物が実質的に除去される、請求項1に記載のプロセス。
- 前記除去工程が、少なくとも一つの分離溶媒を前記洗浄された有機溶液に加えることを含む、請求項1に記載のプロセス。
- 前記少なくとも一つの分離溶媒は、前記少なくとも一つの精製溶媒の沸点よりも高い沸点を有する、請求項15に記載のプロセス。
- 前記少なくとも一つの分離溶媒が、ケトン、エステル、炭化水素、スルホキシド、エーテル、又はそれらの混合物を含む、請求項15に記載のプロセス。
- 前記少なくとも一つの分離溶媒が、メチルエチルケトン、メチルイソブチルケトン、2−へプタノン、シクロペンタノン、シクロヘキサノン、キシレン、ガンマ−ブチロラクトン、ジメチルスルホキシド、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、乳酸エチル、又はそれらの混合物を含む、請求項17に記載のプロセス。
- 前記少なくとも一つの分離溶媒が、前記少なくとも一つの精製溶媒とは異なる、請求項15に記載のプロセス。
- 前記少なくとも一つの分離溶媒が、前記少なくとも一つの精製溶媒と同一である、請求項15に記載のプロセス。
- 前記少なくとも一つの精製溶媒の少なくとも一部が、蒸発又は蒸留により除去される、請求項1に記載のプロセス。
- 前記少なくとも一つの極性非プロトン性重合溶媒中にポリイミド又はポリアミド酸エステルを含有する有機溶液が、ポリイミド又はポリアミド酸エステルを分離することなく、重合反応から得られる、請求項1に記載のプロセス。
- 前記除去工程の後に、前記精製されたポリイミド又はポリアミド酸エステルを含有する溶液を濃縮することをさらに含む、請求項1に記載のプロセス。
- 請求項1のプロセスにより得られる、精製されたポリマー。
- 少なくとも一つの極性非プロトン性重合溶媒中にポリイミド又はポリアミド酸エステルを含有する有機溶液を提供すること;
前記少なくとも一つの重合溶媒よりも極性が低く且つ前記少なくとも一つの重合溶媒よりも25℃での水溶性が低い少なくとも一つの精製溶媒を前記有機溶液に加えて、希釈された有機溶液を形成すること;
前記希釈された有機溶液を、水又は水溶液を用いて洗浄して、洗浄された有機溶液を得ること;
前記洗浄された有機溶液中の前記少なくとも一つの精製溶媒の少なくとも一部を除去して、精製されたポリイミド又はポリアミド酸エステルを含有する溶液を得ること;及び
前記精製されたポリイミド又はポリアミド酸エステルを含有する溶液を基体上に塗布して、膜を形成すること、
を含む、基体上に膜を調製するプロセス。 - 前記除去工程が、少なくとも一つの分離溶媒を前記洗浄された有機溶液に加えることを含む、請求項25に記載のプロセス。
- 前記塗布工程が、インクジェット印刷、スピン塗布、スプレー塗布、ディップ塗布、ローラー塗布、又は動的表面張力塗布により実行される、請求項25に記載のプロセス。
- 前記膜を前記基体から除去することをさらに含む、請求項25に記載のプロセス。
- 請求項28のプロセスにより得られる自立膜。
- 半導体基体と、前記半導体基体上に請求項25のプロセスにより調製した膜と、を含む物品。
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