JP2018197853A - レジスト材料及びパターン形成方法 - Google Patents
レジスト材料及びパターン形成方法 Download PDFInfo
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- JP2018197853A JP2018197853A JP2018087099A JP2018087099A JP2018197853A JP 2018197853 A JP2018197853 A JP 2018197853A JP 2018087099 A JP2018087099 A JP 2018087099A JP 2018087099 A JP2018087099 A JP 2018087099A JP 2018197853 A JP2018197853 A JP 2018197853A
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- 239000000463 material Substances 0.000 title claims abstract description 76
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- 125000004185 ester group Chemical group 0.000 claims description 29
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- VSYDNHCEDWYFBX-UHFFFAOYSA-N (1-methylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCC1 VSYDNHCEDWYFBX-UHFFFAOYSA-N 0.000 description 3
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Abstract
Description
1.下記式(a1)又は(a2)で表される繰り返し単位を含むポリマーを含むレジスト材料。
2.式(a1)及び(a2)で表される繰り返し単位が、それぞれ下記式(a1−1)及び(a2−1)で表されるものである1のレジスト材料。
3.更に、有機溶剤を含む1又は2のレジスト材料。
4.前記ポリマーが、更に、下記式(b1)又は(b2)で表される繰り返し単位を含む1〜3のいずれかのレジスト材料。
5.更に、溶解阻止剤を含む化学増幅ポジ型レジスト材料である4のレジスト材料。
6.前記ポリマーが、酸不安定基を含まないものである1〜3のいずれかのレジスト材料。
7.更に、架橋剤を含む化学増幅ネガ型レジスト材料である6のレジスト材料。
8.更に、界面活性剤を含む1〜7のいずれかのレジスト材料。
9.1〜8のいずれかのレジスト材料を基板上に塗布し、加熱処理をしてレジスト膜を形成する工程と、高エネルギー線で前記レジスト膜を露光する工程と、現像液を用いて前記露光したレジスト膜を現像する工程とを含むパターン形成方法。
10.前記高エネルギー線が、波長193nmのArFエキシマレーザー又は波長248nmのKrFエキシマレーザーである9のパターン形成方法。
11.前記高エネルギー線が、電子線(EB)又は波長3〜15nmのEUVである9のパターン形成方法。
本発明のレジスト材料は、ポリマー結合型酸発生剤、具体的には、重合性不飽和結合を有し、該重合性不飽和結合とフルオロスルホン酸との連結部分にヨウ素原子を有するスルホニウム塩又はヨードニウム塩に由来する繰り返し単位を含むポリマーを含むものである。本発明のレジスト材料には、これとは異なるスルホン酸、イミド酸又はメチド酸を発生させる酸発生剤を添加してもよい。
本発明で用いるポリマー結合型酸発生剤、具体的には、重合性不飽和結合を有し、該重合性不飽和結合とフルオロスルホン酸との連結部分にヨウ素原子を有するスルホニウム塩又はヨードニウム塩に由来する繰り返し単位を含むポリマーは、下記式(a1)で表される繰り返し単位(以下、繰り返し単位a1ともいう。)又は下記式(a2)で表される繰り返し単位(以下、繰り返し単位a2ともいう。)を含むものである。
前記ポリマー結合型酸発生剤に、その他の酸発生剤、有機溶剤、界面活性剤、溶解阻止剤、架橋剤、クエンチャー等を目的に応じて適宜組み合わせて配合してポジ型レジスト材料及びネガ型レジスト材料を構成することによって、露光部では前記ベースポリマーが触媒反応により現像液に対する溶解速度が加速されるので、極めて高感度のポジ型レジスト材料及びネガ型レジスト材料とすることができる。この場合、レジスト膜の溶解コントラスト及び解像性が高く、露光余裕度があり、プロセス適応性に優れ、露光後のパターン形状が良好でありながら、特に酸拡散を抑制できることから粗密寸法差が小さく、これらのことから実用性が高く、超LSI用レジスト材料として非常に有効なものとすることができる。特に、酸触媒反応を利用した化学増幅ポジ型レジスト材料とすると、より高感度のものとすることができると共に、諸特性が一層優れたものとなり極めて有用なものとなる。
本発明のレジスト材料を種々の集積回路製造に用いる場合は、公知のリソグラフィー技術を適用することができる。
2Lのフラスコに、メタクリル酸1−メチル−1−シクロペンチル8.4g、メタクリル酸−4−ヒドロキシフェニル3.6g、メタクリル酸3−オキソ−2,7−ジオキサトリシクロ[4.2.1.04,8]ノナン−9−イルを4.5g、PAGモノマー1を8.1g、及び溶剤としてTHFを40g添加した。この反応容器を、窒素雰囲気下、−70℃まで冷却し、減圧脱気、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1L溶液中に沈殿させ、得られた白色固体を濾過後、60℃で減圧乾燥し、ポリマー1を白色固体として得た。ポリマー1の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー1のかわりにPAGモノマー2を10.3g使用した以外は、合成例1と同じ方法で、ポリマー2を白色固体として得た。ポリマー2の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー1のかわりにPAGモノマー3を10.3g使用した以外は、合成例1と同じ方法で、ポリマー3を白色固体として得た。ポリマー3の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー1のかわりにPAGモノマー4を9.3g使用した以外は、合成例1と同じ方法で、ポリマー4を白色固体として得た。ポリマー4の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
2Lのフラスコに、メタクリル酸1−メチル−1−シクロペンチル8.4g、4−ヒドロキシスチレン4.8g、PAGモノマー5を9.1g、及び溶剤としてTHFを40g添加した。この反応容器を、窒素雰囲気下、−70℃まで冷却し、減圧脱気、窒素ブローを3回繰り返した。室温まで昇温後、重合開始剤としてAIBNを1.2g加え、60℃まで昇温後、15時間反応させた。この反応溶液をイソプロピルアルコール1L溶液中に沈殿させ、得られた白色固体を濾過後、60℃で減圧乾燥し、ポリマー5を白色固体として得た。ポリマー5の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー5のかわりにPAGモノマー6を7.1g使用した以外は、合成例5と同じ方法で、ポリマー6を白色固体として得た。ポリマー6の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー5のかわりにPAGモノマー7を9.2g使用した以外は、合成例5と同じ方法で、ポリマー7を白色固体として得た。ポリマー7の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
メタクリル酸1−メチル−1−シクロペンチルのかわりに4−アミロキシ−3−フルオロスチレンを13.5g使用し、4−ヒドロキシスチレンを3.0g使用した以外は、合成例7と同じ方法で、ポリマー8を白色固体として得た。ポリマー8の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
PAGモノマー1のかわりに比較PAGモノマー1を7.6g使用した以外は、合成例1と同じ方法で、比較ポリマー1を白色固体として得た。比較ポリマー1の組成は13C−NMR及び1H−NMRにより、Mw及びMw/MnはGPCにより確認した。
(1)レジスト材料の調製
界面活性剤としてスリーエム社製FC-4430を100ppm溶解させた溶剤に、表1に示される組成で各成分を溶解させた溶液を、0.2μmサイズのフィルターで濾過し、レジスト材料を調製した。
・有機溶剤:PGMEA(プロピレングリコールモノメチルエーテルアセテート)
CyH(シクロヘキサノン)
PGME(プロピレングリコールモノメチルエーテル)
DAA(ジアセトンアルコール)
実施例1〜11及び比較例1で調製した各レジスト材料を、信越化学工業(株)製ケイ素含有スピンオンハードマスクSHB-A940(ケイ素の含有量が43質量%)を20nm膜厚で形成したSi基板上にスピンコートし、ホットプレートを用いて105℃で60秒間プリベークし、膜厚60nmのレジスト膜を作製した。これに、ASML社製EUVスキャナーNXE3300(NA0.33、σ0.9/0.6、クアドルポール照明、ウエハー上寸法がピッチ46nm、+20%バイアスのホールパターンのマスク)を用いて露光し、ホットプレートを用いて表1記載の温度で60秒間PEBを行い、2.38質量%TMAH水溶液で30秒間現像を行って、寸法23nmのホールパターンを形成した。
(株)日立ハイテクノロジーズ製測長SEM(CG5000)を用いて、ホール寸法が23nmで形成されるときの露光量を測定してこれを感度とし、また、このときのホール50個の寸法を測定し、寸法バラツキ(CDU、3σ)を求めた。結果を表1に併記する。
Claims (11)
- 下記式(a1)又は(a2)で表される繰り返し単位を含むポリマーを含むレジスト材料。
- 更に、有機溶剤を含む請求項1又は2記載のレジスト材料。
- 前記ポリマーが、更に、下記式(b1)又は(b2)で表される繰り返し単位を含む請求項1〜3のいずれか1項記載のレジスト材料。
- 更に、溶解阻止剤を含む化学増幅ポジ型レジスト材料である請求項4記載のレジスト材料。
- 前記ポリマーが、酸不安定基を含まないものである請求項1〜3のいずれか1項記載のレジスト材料。
- 更に、架橋剤を含む化学増幅ネガ型レジスト材料である請求項6記載のレジスト材料。
- 更に、界面活性剤を含む請求項1〜7のいずれか1項記載のレジスト材料。
- 請求項1〜8のいずれか1項記載のレジスト材料を基板上に塗布し、加熱処理をしてレジスト膜を形成する工程と、高エネルギー線で前記レジスト膜を露光する工程と、現像液を用いて前記露光したレジスト膜を現像する工程とを含むパターン形成方法。
- 前記高エネルギー線が、波長193nmのArFエキシマレーザー又は波長248nmのKrFエキシマレーザーである請求項9記載のパターン形成方法。
- 前記高エネルギー線が、電子線又は波長3〜15nmの極端紫外線である請求項9記載のパターン形成方法。
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KR20200112735A (ko) | 2019-03-22 | 2020-10-05 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 레지스트 조성물 및 패턴 형성 방법 |
JP2020181064A (ja) * | 2019-04-24 | 2020-11-05 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法、感放射線性酸発生剤及び化合物 |
JP7247732B2 (ja) | 2019-04-24 | 2023-03-29 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法、感放射線性酸発生剤及び化合物 |
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US11773059B2 (en) | 2020-06-04 | 2023-10-03 | Shin-Etsu Chemical Co., Ltd. | Onium salt, chemically amplified negative resist composition, and pattern forming process |
KR20210150994A (ko) | 2020-06-04 | 2021-12-13 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 오늄염, 화학 증폭 네거티브형 레지스트 조성물 및 레지스트 패턴 형성 방법 |
WO2022130869A1 (ja) * | 2020-12-17 | 2022-06-23 | Jsr株式会社 | 感放射線性組成物及びレジストパターン形成方法 |
WO2022149349A1 (ja) * | 2021-01-08 | 2022-07-14 | Jsr株式会社 | 感放射線性組成物及びレジストパターン形成方法 |
WO2023058369A1 (ja) * | 2021-10-06 | 2023-04-13 | Jsr株式会社 | 感放射線性樹脂組成物、樹脂、化合物及びパターン形成方法 |
WO2023157455A1 (ja) * | 2022-02-21 | 2023-08-24 | Jsr株式会社 | 感放射線性組成物及びレジストパターン形成方法 |
WO2024084993A1 (ja) * | 2022-10-19 | 2024-04-25 | Jsr株式会社 | 感放射線性組成物、レジストパターン形成方法及び重合体 |
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JP6973274B2 (ja) | 2021-11-24 |
TWI668241B (zh) | 2019-08-11 |
US20180335696A1 (en) | 2018-11-22 |
KR20180127924A (ko) | 2018-11-30 |
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US11022883B2 (en) | 2021-06-01 |
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