JP2007128036A - 有機反射防止膜重合体、これを含む有機反射防止膜組成物及びこれを用いたフォトレジストのパターン形成方法 - Google Patents
有機反射防止膜重合体、これを含む有機反射防止膜組成物及びこれを用いたフォトレジストのパターン形成方法 Download PDFInfo
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Abstract
【解決手段】下記一般式(1)で表示され、2000〜100000の重量平均分子量を有する有機反射防止膜重合体を提供する。
【化1】
(1)
(式中、R1はC1〜C5の直鎖または側鎖アルキル基を表し、R2及びR3はそれぞれ水素またはメチル基を表し、Xはハロゲンを表し、nは1〜5を表し、a、b及びcは各単量体のモル分率であって、それぞれ0.1〜0.9を表す。)
【選択図】図2
Description
(1)
(3)
(4)
(5)
(1)
(2)
(6)
4−ブロモスチレン3g、アクロレイン単量体4g、メタクリレート単量体3g、及びAIBN0.2gをPGMEA50gとよく混合した後に、67℃の温度で8時間重合反応させた。重合反応が完了すると、該反応結果物をノルマルヘキサンで沈殿しろ過して真空乾燥することで、ポリ(ブロモスチレン−アクロレイン−メタクリレート)共重合体を得た。
(7)
上記実施例1で製造された一般式(7)の重合体1g、光吸収剤とされるポリビニルフェノール重合体0.2g及び熱酸発生剤とされる2−ヒドロキシシクロヘキシルパラトルエンスルホネート0.8gを、プロピレングリコールメチルエーテルアセテート60gに溶解させた後、0.05μmの微細フィルターに通過させて有機反射防止膜組成物を製造した。
実施例2によって有機反射防止膜が形成されたウエーハ上に、JSRのAR1221J ArF感光剤をコーティングし、130℃の温度で90秒間ベークした。その後、ASML社のArFスキャナー(NA=0.63)を使用して露光し、再び130℃で90秒間ベークした後、2.38重量%TMAH現像液で現像し、最終フォトレジストパターンを形成した。このフォトレジストパターンを、図2に示す。
Claims (14)
- 下記一般式(1)で表示され、2000〜100000の重量平均分子量を有する有機反射防止膜重合体。
(1)
(式中、R1はC1〜C5の直鎖または側鎖アルキル基を表し、R2及びR3はそれぞれ水素またはメチル基を表し、Xはハロゲンを表し、nは1〜5を表し、a、b及びcは各単量体のモル分率であって、それぞれ0.1〜0.9を表す。) - 前記R1はメチルで、R2はメチルで、R3は水素で、Xは4−臭素で、nは1である、請求項1に記載の有機反射防止膜重合体。
- 下記一般式(3)のアクロレイン系単量体、下記一般式(4)のアルキルアクリレイト系単量体及び下記一般式(5)のハロゲン化スチレン系単量体を有機溶媒に溶かし、ここに重合開始剤を添加した後、真空状態の下に60〜70℃の温度で4〜8時間重合反応を行う工程と、
上記重合反応から得られた共重合体を、パラトルエンスルホン酸触媒下に、60〜80℃の温度で20〜30時間、R1OHで表示されるアルコール(R1は、C1〜C5の直鎖または側鎖アルキル基を表す。)と反応させることで、下記一般式(1)の重合体を製造する工程と、
を含む、有機反射防止膜重合体の製造方法。
(3)
(4)
(5)
(1)
(式中、R1はC1〜C5の直鎖または側鎖アルキル基を表し、R2及びR3はそれぞれ水素またはメチル基を表し、Xはハロゲンを表し、nは1〜5を表し、a、b及びcは各単量体のモル分率であって、それぞれ0.1〜0.9を表す。) - 前記有機溶媒には、プロピレングリコールメチルエーテルアセテート(PGMEA)、テトラヒドラフラン(THF)、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、ジオキサン、メチルエチルケトン、ベンゼン、トルエン及びキシレンからなるグループより選ばれた1またはそれ以上を混合して使用する、請求項3に記載の有機反射防止膜重合体の製造方法。
- 前記重合開始剤には、2,2−アゾビスイソブチロニトリル(AIBN)、ベンゾイルペルオキシド、アセチルペルオキシド、ラウリルペルオキシド、t−ブチルペルアセテート、t−ブチルヒドロペルオキシド及びジ−t−ブチルペルオキシドからなるグループより選ばれたいずれかを使用する、請求項3に記載の有機反射防止膜重合体の製造方法。
- 下記一般式(1)で表示され、2000〜100000の重量平均分子量を有する重合体と、下記一般式(2)で表示されるポリビニルフェノール重合体と、熱酸発生剤と、有機溶媒とを含む、有機反射防止膜組成物。
(1)
(式中、R1はC1〜C5の直鎖または側鎖アルキル基を表し、R2及びR3はそれぞれ水素またはメチル基を表し、Xはハロゲンを表し、nは1〜5を表し、a、b及びcは各単量体のモル分率であって、それぞれ0.1〜0.9を表す。)
(2) - 前記熱酸発生剤には、下記一般式(6)の構造を有する2−ヒドロキシヘキシルパラトルエンスルホネートを使用する、請求項6に記載の有機反射防止膜組成物。
(6) - 前記ポリビニルフェノール重合体は、組成物に含まれる上記一般式(1)の重合体の100重量部に対して50〜200重量部で含まれる、請求項6に記載の有機反射防止膜組成物。
- 前記熱酸発生剤は、組成物に含まれる上記一般式(1)の重合体の100重量部に対して10〜200重量部で含まれる、請求項7に記載の有機反射防止膜組成物。
- 前記有機溶媒は、組成物に含まれる上記一般式(1)の重合体及びポリビニルフェノール重合体の合計量100重量部に対して1000〜10000重量部で含まれる、請求項6に記載の有機反射防止膜組成物。
- 請求項6乃至10のいずれか1項による有機反射防止膜組成物を、被エッチング層上部に塗布する工程と、
前記結果物に対してベーク工程を行い架橋結合を形成させることで有機反射防止膜を形成する工程と、
前記形成された有機反射防止膜の上部に、フォトレジストを塗布し、露光後に現像してフォトレジストパターンを形成する工程と、
を含む、フォトレジストのパターン形成方法。 - 前記ベーク工程は、150〜300℃の温度で1〜5分間行う、請求項11に記載のフォトレジストのパターン形成方法。
- 前記フォトレジストパターンの形成工程中に、露光する前や後にベーク工程をさらに行う、請求項11に記載のフォトレジストのパターン形成方法。
- 前記ベーク工程は、70〜200℃の温度で行う、請求項13に記載のフォトレジストのパターン形成方法。
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KR1020050103343A KR100732763B1 (ko) | 2005-10-31 | 2005-10-31 | 유기 반사 방지막 중합체, 이를 포함하는 유기 반사 방지막조성물 및 이를 이용한 포토레지스트의 패턴 형성 방법 |
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JP2010506992A (ja) * | 2006-10-18 | 2010-03-04 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
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TW200736855A (en) * | 2006-03-22 | 2007-10-01 | Quanta Display Inc | Method of fabricating photoresist thinner |
KR100960463B1 (ko) * | 2007-08-09 | 2010-05-28 | 주식회사 하이닉스반도체 | 반사방지막용 중합체, 이를 포함하는 반사방지막 조성물 및이를 이용한 패턴 형성방법 |
WO2013018802A1 (ja) * | 2011-08-04 | 2013-02-07 | 日産化学工業株式会社 | 縮合系ポリマーを有するeuvリソグラフィー用レジスト下層膜形成組成物 |
DE102016200814A1 (de) | 2016-01-21 | 2017-07-27 | Carl Zeiss Smt Gmbh | Reflektives optisches Element und optisches System für die EUV-Lithographie |
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KR100832247B1 (ko) * | 2002-11-27 | 2008-05-28 | 주식회사 동진쎄미켐 | 유기 난반사 방지막 조성물 및 이를 이용한 패턴 형성방법 |
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JPH02272457A (ja) * | 1989-04-13 | 1990-11-07 | Fuji Photo Film Co Ltd | 感電離放射線性樹脂組成物 |
JP2005015763A (ja) * | 2003-06-27 | 2005-01-20 | Hynix Semiconductor Inc | フォトレジスト重合体、フォトレジスト組成物、フォトレジストパターン形成方法及び半導体素子 |
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JP2010506992A (ja) * | 2006-10-18 | 2010-03-04 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
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KR20070046532A (ko) | 2007-05-03 |
KR100732763B1 (ko) | 2007-06-27 |
CN1958629B (zh) | 2010-12-08 |
JP5043376B2 (ja) | 2012-10-10 |
US20070099110A1 (en) | 2007-05-03 |
TWI328146B (en) | 2010-08-01 |
US7531297B2 (en) | 2009-05-12 |
TW200717181A (en) | 2007-05-01 |
CN1958629A (zh) | 2007-05-09 |
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