JP2018106152A - ケイ素含有下層を使用する方法 - Google Patents
ケイ素含有下層を使用する方法 Download PDFInfo
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Abstract
【解決手段】(a)ポリマー主鎖にペンダントしている縮合性ケイ素含有部分を有する1つ以上の第1の不飽和モノマーを重合単位として含む1つ以上のポリマーの1つ以上の縮合物及び/または加水分解物を含む組成物で基板をコーティングして、コーティング層を形成すること、(b)コーティング層を硬化させてポリマー下層を形成すること、(c)ポリマー下層上にフォトレジストの層を配設すること、(d)フォトレジスト層をパターン状に露光して潜像を形成すること、(e)潜像を現像して中にレリーフ画像を有するパターン形成されたフォトレジスト層を形成すること、(f)レリーフ画像を基板に転写すること、(g)湿式剥離によってポリマー下層を除去すること、を含む、方法。
【選択図】なし
Description
水(156g)中の塩酸(6.15gの12.1N)を、メチルトリメトキシシラン(99.80g)、フェニルトリメトキシシラン(50.41g)、ビニルトリメトキシシラン(62.75g)、テトラエチルオルトシリケート(294g)、及び2−プロパノール(467g)の混合物に10分かけて加えた。その反応混合物を室温で1時間撹拌し、24時間加熱して還流し、室温まで冷却した。その溶液をプロピレングリコールモノエチルエーテル(PGEE)(800g)で希釈し、低沸点の反応混合物成分を減圧下で除去した。得られた溶液をPGEEで希釈して、比較ポリマー1(Mw=9000Da)の最終10重量%溶液を得た。
1,3−ジオキソラン(304g)中に溶解されたtert−ブチルメタクリレート(tBMA)、(173g)、ガンマ−ブチロラクトン(GBLMA)、(166g)、及び3−(トリメトキシシリル)プロピルメタクリレート(TMSPMA)、(60.6g)の溶液と、2:1v/vテトラヒドロフラン/アセトニトリル(60.6g)中に溶解されたV−65開始剤(60.6g)の溶液の両方を、窒素ブランケット下、75℃で、3−ジオキソラン(710g)に対して2時間かけて滴加した。添加後、その反応溶液を75℃でさらに2時間保持し、室温まで冷却し、ヘプタン:MTBE(1:1v/v、14L)中に沈殿させた。沈殿したポリマーを真空ろ過により回収し、24時間真空オーブンで乾燥させて、ポリマー1(tBMA/GBLMA/TMSPMA50/40/10)を白色固体(271g、68%)として得た。Mwはポリスチレン標準に対するGPCにより決定され、5700Daであることが判明した。
実施例1からのポリマー1(15g、91.5mmol)及び35gのテトラヒドロフラン(THF)を、熱電対、オーバーヘッドスターラー、水冷コンデンサー、添加漏斗、N2供給ライン、バブラー、及び加熱マントルを備えた250mLの三つ口丸底フラスコに入れた。その混合物を、すべてのポリマーが溶解するまで室温で撹拌した。別の容器では、塩酸(0.122g、1.235mmol)及びDI水(0.816g、45.2mmol)を一緒に混合した。その酸性水溶液を周囲温度で10分間かけて添加漏斗を介して反応器に入れた。その混合物を室温で1時間撹拌した。次いで、温度を63±2℃に30分間にわたって調整して還流を開始した。その溶液を還流温度で4時間撹拌した。その反応混合物を、撹拌を続けながら一晩室温まで冷却した。次に、その溶液を、PGEEで希釈し、減圧下、ロータリーエバポレーターで濃縮して縮合ポリマー1を得た。その溶液を、1時間ローリングすることによってAmberlite(商標)IRN150イオン交換樹脂(最終重量10重量%)で処理し、0.2μmのポリテトラフルオロエチレン(PTFE)フィルターを使用してろ過し、そして−10℃のプラスチック容器中に保存した。縮合ポリマー1を分析すると、Mwは51,000Da及びPDIは4.3であった。
以下の表2に報告するポリマー2〜13を、以下の表1に掲げたモノマーを使用して実施例1の手順に従って合成した。使用された各モノマーの量を表2にmol%で示す。ポリマー2〜12は20〜99%の収率で単離され、表2に報告したMwを有していた。
12g(70.4mmol)のポリマー4を、28gのTHF及び0.094g(0.95mmol)のHClと組み合わせた以外は、実施例2の一般的手順を繰り返し、そして0.628g(34.8mmol)のDI水を使用した。縮合ポリマー4を分析すると、Mwは39,000Da及びPDIは2.8であった。
ポリマー3をTHFと組み合わせて縮合ポリマー3を得た以外は実施例2の一般的手順を繰り返した。
ポリマー1を、実施例3からのポリマー4〜13のそれぞれで置き換える以外は実施例2の一般的手順を繰り返し、それぞれ縮合ポリマー4〜13が提供されることが予期される。
Claims (16)
- (a)ポリマー主鎖にペンダントしている縮合性ケイ素含有部分を有する1つ以上の第1の不飽和モノマーを重合単位として含む1つ以上のポリマーの1つ以上の縮合物及び/または加水分解物を含む組成物で基板をコーティングして、コーティング層を形成することと、(b)前記コーティング層を硬化させてポリマー下層を形成することと、(c)前記ポリマー下層上にフォトレジストの層を配設することと、(d)前記フォトレジスト層をパターン状に露光して潜像を形成することと、(e)前記潜像を現像して中にレリーフ画像を有するパターン形成されたフォトレジスト層を形成することと、(f)前記レリーフ画像を前記基板に転写することと、(g)湿式剥離によって前記ポリマー下層を除去することと、を含む、方法。
- 前記縮合性ケイ素含有部分が、式
- Lが2価の連結基である、請求項2に記載の方法。
- 前記2価の連結基が、酸素及びケイ素から選択される1個以上のヘテロ原子を含む、請求項3に記載の方法。
- 前記2価の連結基が、1〜20個の炭素原子及び場合により1個以上のヘテロ原子を有する有機ラジカルである、請求項3に記載の方法。
- 前記2価の連結基が式−C(=O)−O−L1−を有し、式中L1は単結合または1〜20個の炭素原子を有する有機ラジカルである、請求項2に記載の方法。
- 少なくとも1つの第1の不飽和モノマーが、式(2)
- 前記オリゴマーが、重合単位として、縮合性ケイ素含有部分を有していない1つ以上の第2の不飽和モノマーをさらに含む、請求項1に記載の方法。
- 少なくとも1つの第2の不飽和モノマーが、酸性プロトンを有し、−5〜13の水中pKaを有する、請求項8に記載の方法。
- 少なくとも1つの第2の不飽和モノマーが、式(4)
- 前記オリゴマーが、発色団部分を有する1つ以上の第3の不飽和モノマーを重合単位としてさらに含む、請求項1に記載の方法。
- 少なくとも1つの第3のモノマーが、前記ポリマー主鎖からペンダントしている発色団部分を有する、請求項11に記載の方法。
- 前記発色団部分が、ピリジル、フェニル、ナフチル、アセナフチル、フルオレニル、カルバゾリル、アントラセニル、フェナントリル、ピレニル、コロネニル、テトラセニル、ペンタセニル、テトラフェニル、ベンゾテトラセニル、トリフェニレニル、及びペリレニルから選択される、請求項12に記載の方法。
- ポリマー主鎖にペンダントしている縮合性ケイ素含有部分を有する1つ以上の第1の不飽和モノマーと、縮合性ケイ素含有部分を有していない1つ以上の追加の不飽和モノマーとを重合単位として含むポリマーの縮合物及び/または加水分解物であって、少なくとも1つの追加のモノマーが、酸分解性基、ラクトン部分を有する1価の有機残基、またはそれらの組み合わせから選択されるペンダント部分を含む、ポリマーの縮合物及び/または加水分解物と、1つ以上の溶媒とを含む、組成物。
- 少なくとも1つの追加のモノマーが、式(4)
- ピリジル、フェニル、ナフチル、アセナフチル、フルオレニル、カルバゾリル、アントラセニル、フェナントリル、ピレニル、コロネニル、テトラセニル、ペンタセニル、テトラフェニル、ベンゾテトラセニル、トリフェニレニル、及びペリレニルから選択される発色団部分を含む少なくとも1つの追加のモノマーをさらに含む、請求項14に記載の組成物。
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