JP2016139123A - オーバーコートされたフォトレジストと共に使用するためのコーティング組成物 - Google Patents
オーバーコートされたフォトレジストと共に使用するためのコーティング組成物 Download PDFInfo
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- JP2016139123A JP2016139123A JP2015243934A JP2015243934A JP2016139123A JP 2016139123 A JP2016139123 A JP 2016139123A JP 2015243934 A JP2015243934 A JP 2015243934A JP 2015243934 A JP2015243934 A JP 2015243934A JP 2016139123 A JP2016139123 A JP 2016139123A
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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Landscapes
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- Textile Engineering (AREA)
- Architecture (AREA)
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- Materials For Photolithography (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
Abstract
【解決手段】フォトレジストレリーフ像を形成するための方法であって、a)基材上に、1)マトリックスポリマー及び2)表面エネルギー調整剤を含むコーティング組成物の層を塗布することと、b)前記コーティング組成物層の上にフォトレジスト組成物の層を塗布することと、を含み、前記表面エネルギー調整剤は、以下の式(I)に対応する構造を含み、式中、A及びBはそれぞれ独立して、水素、任意に置換されたアルキル、または任意に置換されたアリールであり、X及びYはそれぞれ独立して、水素、任意に置換されたアルキル、または任意に置換された炭素環式アリールであり、nは正の整数である、前記方法。
【選択図】なし
Description
下地コーティング組成物と用いるためのフォトレジストは典型的にポリマーと1つ以上の酸発生剤とを含む。一般的に好ましいのはポジ型レジストであり、レジストポリマーはレジスト組成物にアルカリ性の水溶解性を与える官能基を有する。例えば、好まれるのは、ヒドロキシルまたはカルボキシレートなどの極性官能基、またはリソグラフィ加工のときにかかる極性部分を遊離させることができる酸不安定基を含む、ポリマーである。好ましくは、ポリマーは、水性アルカリ溶液で現像可能なレジストを行うのに十分な量でレジスト組成物に用いられる。
使用において、本発明のコーティング組成物は、スピンコーティングなどの多種多様の方法の任意のものによって、コーティング層として基材に塗布される。一般的にコーティング組成物は基材上に、約0.02〜0.5μmの乾燥層厚さ、好ましくは約0.04〜0.20μmの乾燥層厚さで塗布される。基材は好適に、フォトレジストを伴う処理に用いられる任意の基材である。例えば、基材は、ケイ素、二酸化ケイ素、またはアルミニウム−酸化アルミニウムマイクロ電子ウェハであり得る。ガリウムヒ素、炭化ケイ素、セラミック、石英、または銅基材もまた使用してもよい。液晶ディスプレイまたは他のフラットパネルディスプレイ用途のための基材、例えばガラス基材、インジウムスズ酸化物でコーティングされた基材なども、好適に使用される。光学及び光学電子デバイス(例えば、導波管)のための基材もまた、使用可能である。
本明細書において「マトリックスポリマー1」または単に「ポリマー1」と称されるポリマーを以下のように調製する。14gのジブチル3,3’−(5−(2−(tert−ブトキシ)−2−オキソエチル)−2,4,6−トリオキソ−1,3,5−トリアジナン−1,3−ジイル)ジプリピオネート、27gのトリス−(2−ヒドロキシエチル)イソシアヌレート、触媒量のp−トルエンスルホン酸一水和物、及び33gのアニソールを反応器に装填した。反応を加熱し、還流した。反応が完了した後に、反応溶液を冷却及び希釈した。溶液を、十分な量のアルコール溶剤に添加して、ブフナー漏斗で濾過することで収集して、空気乾燥し、次に真空下で乾燥させた。得られたポリマーは標準ポリスチレン単位で9000の重量平均分子量を有した。
本明細書において「マトリックスポリマー2」または単に「ポリマー2」と称されるポリマーを以下のように調製する。17gのトリス−(2−カルボキシエチル)イソシアヌレート、23gのトリス−(2−ヒドロキシエチル)イソシアヌレート、触媒量のp−トルエンスルホン酸一水和物、及び33gのアニソールを反応器に装填した。反応が完了した後、反応溶液を冷却及び希釈した。ポリマーを、十分な量のイソプロピルアルコールに滴下することで沈殿させ、ブフナー漏斗で濾過することで収集して、空気乾燥し、次に真空下で乾燥させた。得られたポリマーは標準ポリスチレン単位で7000の重量平均分子量を有した。
本明細書において「マトリックスポリマー3」または単に「ポリマー3」と称されるポリマーを以下のように調製する。15gのN−アリル−ビス(2−カルボキシルエチル)イソシアヌレート、27gのトリス−(2−ヒドロキシエチル)イソシアヌレート、触媒量のp−トルエンスルホン酸一水和物(PTSA)、及び30gのアニソールを、反応器に装填した。反応が完了した後、反応溶液を冷却及び希釈した。ポリマーを、十分な量のアルコール溶剤に滴下することで沈殿させ、ブフナー漏斗で濾過することで収集して、空気乾燥し、次に真空下で乾燥させた。得られたポリマーは標準ポリスチレン単位で19000の重量平均分子量を有した。
以下の量の材料をそれぞれ秤量して好適な容器に入れる:1)48.14gのスチレンモノマー(液体)、2)1.86gの2−ヒドロキシエチルメタクリレートモノマー(液体)。
以下の表1に要約された以下の実施例5〜31及び比較例1〜4では、特定の成分及び架橋剤(テトラメトキシメチルグリコウリル、TMGU)ならびに酸硬化触媒を混ぜることで、下地コーティング組成物を調製した。水静的接触角(水SCA)を、以下に記載する水静的接触角測定プロトコル(Water Static Contact Angle Measurement Protocol)によって、コーティング組成物それぞれについて求めた。
0.812gのポリマー1(上記実施例1で調製されたもの)、0.03gのPEG300(上記のように300のMnを有するポリ(エチレングリコール))、0.15gのTMGUを架橋剤として、及び0.008gのpTSA・NH3を熱酸触媒として混合して、この混合物に99gのHBMを溶剤として添加した。次に、溶液を0.45gmのPTFEフィルタを通して濾過した。
0.752gのポリマー1(上記実施例1で調製されたもの)、0.09gのPEG1500(上記のように1500のMnを有するポリ(エチレングリコール))、0.15gのTMGUを架橋剤として、及び0.008gのpTSA・NH3を熱酸触媒として混合して、この混合物に99gのHBMを溶剤として添加した。次に、溶液を0.45μmのPTFEフィルタを通して濾過した。
0.692gのポリマー2(上記実施例2で調製されたもの)、0.15gのPEGME750(上記のように750のMnを有するポリ(エチレングリコール)メチルエーテル)、0.15gのTMGUを架橋剤として、及び0.008gのpTSA・NH3を熱酸触媒として混合して、この混合物に99gのHBMを溶剤として添加した。次に、溶液を0.45μmのPTFEフィルタを通して濾過した。
200nmのウェハシリコンウェハに、実施例5〜31及び比較例1〜4から調製した液体コーティング組成物をスピンコートした。ウェハを60秒間、205℃でベークして、250ÅのBARC膜厚を得た。4.5μm大の水をKruss DSA100によってコーティングされたウェハ上に配置し、静的接触角を測定した。この接触角測定プロトコルは、本明細書の他の箇所で水静的接触角測定プロトコルと称される。
ポリ(エチレングリコール)及びポリ(エチレングリコール)メチルエーテルの表面エネルギー調整剤をポリエステルマトリックスポリマーとさまざまな量で配合し、水静的接触角測定プロトコルによって上記のように水静的接触角を求めた。結果は以下の表2に記載されており、特定の表面エネルギー調整剤の量はコーティング組成物の全固形分の重量に対する重量パーセントとして表される(すなわち、特定の表面エネルギー調整剤及びポリエステルマトリックス樹脂)。
300mmのHMDS刺激されたシリコンウェハに、ARTM26N(Rohm and Haas Electronic Materials社)をスピンコートして、第1の底部反射防止コーティング(BARC)をTEL CLEAN TRAC LITHIUS i+上に形成し、次に60秒間、205℃のベークプロセスに供して、900Åの第1のBARC層厚さを得た。
Claims (10)
- 前記フォトレジスト組成物は、活性化放射線で撮像され、前記撮像されたフォトレジスト組成物層は、現像されてフォトレジストレリーフ像を提供する、請求項1に記載の前記方法。
- 現像液は、前記撮像されたフォトレジスト組成物層に塗布され、前記フォトレジスト層の非露光部分は、前記現像液によって除去される、請求項2に記載の前記方法。
- 前記表面調整剤は、300〜5,000の数平均分子量を有する、請求項1に記載の方法。
- 前記コーティング組成物は、前記表面剤を、前記コーティング組成物の全固形分に基づいて1重量パーセント〜10重量パーセントの量で含む、請求項1に記載の前記方法。
- 前記コーティング組成物層は、前記フォトレジスト組成物層を塗布する前に熱処理される、請求項1に記載の前記方法。
- 架橋剤をさらに含む、請求項8に記載の前記コーティング組成物。
- 前記コーティング組成物は溶剤担体と配合される、請求項8に記載の前記コーティング組成物。
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KR102110178B1 (ko) | 2020-05-13 |
JP2019003200A (ja) | 2019-01-10 |
CN105739236B (zh) | 2022-07-19 |
US11762292B2 (en) | 2023-09-19 |
KR20180006474A (ko) | 2018-01-17 |
CN105739236A (zh) | 2016-07-06 |
TW201626109A (zh) | 2016-07-16 |
TWI592760B (zh) | 2017-07-21 |
JP6788639B2 (ja) | 2020-11-25 |
US20160187778A1 (en) | 2016-06-30 |
KR20160082470A (ko) | 2016-07-08 |
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