JPWO2012053302A1 - Euvリソグラフィー用レジスト上層膜形成組成物 - Google Patents
Euvリソグラフィー用レジスト上層膜形成組成物 Download PDFInfo
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Abstract
Description
このような反射防止膜としては、チタン、二酸化チタン、窒化チタン、酸化クロム、カーボン、α−シリコン等の無機反射防止膜や、吸光性物質と高分子化合物とからなる有機反射防止膜が知られている。前者は膜形成に真空蒸着装置、CVD装置、スパッタリング装置等の設備を必要とするのに対し、後者は特別の設備を必要としない点で有利とされ数多くの検討が行われている。
第2観点として、樹脂が親水性基としてヒドロキシ基、カルボキシル基、スルホ基、又はこれらの基のうち少なくとも一つの基を含む一価の有機基を含むものである、第1観点に記載のEUVレジスト上層膜形成組成物に関する。
第3観点として、樹脂が式(1)で表される単位構造、又は、式(1)及び式(2)で表される単位構造を含む、第1観点又は第2観点に記載のEUVレジスト上層膜形成組成物に関する。:
第4観点として、樹脂が式(3)で表される単位構造、又は、式(3)及び式(4)で表される単位構造、又は、式(3)及び式(5)で表される単位構造、又は、式(3)及び式(4)及び式(5)で表される単位構造、又は、式(3)及び式(5)及び式(6)で表される単位構造、又は、式(3)及び式(4)及び式(5)及び式(6)で表される単位構造を含む、第1観点又は第2観点に記載のEUVレジスト上層膜形成組成物に関する。:
第5観点として、溶剤がアルコール系溶剤である、第1観点乃至第4観点のいずれか1項に記載のEUVレジスト上層膜形成組成物に関する。
第6観点として、更に酸化合物を含む、第1観点乃至第5観点のいずれか1項に記載のEUVレジスト上層膜形成組成物に関する。
第7観点として、酸化合物がスルホン酸化合物又はスルホン酸エステル化合物である、第6観点に記載のEUVレジスト上層膜形成組成物に関する。
第8観点として、酸化合物がヨードニウム塩系酸発生剤又はスルホニウム塩系酸発生剤である、第6観点に記載のEUVレジスト上層膜形成組成物に関する。
第9観点として、基板上にEUVレジスト膜を形成する工程、
該レジスト膜上に請求項1乃至請求項8のいずれか1項に記載のEUVレジスト上層膜形成組成物を塗布し焼成してEUVレジスト上層膜を形成する工程、
該レジスト上層膜とレジスト膜で被覆された半導体基板を露光する工程、
露光後に現像し該レジスト上層膜とレジスト膜を除去する工程、
を含む半導体装置の製造方法に関する。
第10観点として、露光がEUV(波長13.5nm)光により行われる、第9観点に記載の半導体装置の製造方法に関する。
特に本発明のEUVレジスト上層膜形成組成物は、EUV露光光に含まれる帯域外光放射のなかでも、最も望ましくないとされる200〜240nmのDUV光を吸収できるレジスト上層膜を提供でき、これにより、EUVレジストの解像性の向上を行うことができる。
また本発明のEUVレジスト上層膜形成組成物は、該組成物を半導体装置の製造に適用する際、下層に形成されるEUVレジストとインターミキシングが起きず、またEUV露光後には、EUVレジストと共に現像液によって除去可能である。
前述したように、EUVリソグラフィーを用いたデバイス作製工程では、EUVレジストを被覆した基板にEUV光を照射して露光させる。ここでEUVレジストの露光に際し、EUV光はEUV光以外に300nm以下の波長の光(すなわちUV光やDUV光)を5%程度含み得る。そして、例えば190〜300nm、190〜250nm、特に200〜240nm付近の波長光はEUVレジストの感度低下やパターン形状の劣化につながる。特に線幅が22nm以下になると、このUV光やDUV光といった帯域外光放射(out−of−BAND radiation)の影響が出始め、EUVレジストの解像性に悪影響を与える。こうした200〜240nm付近の望ましくない波長光を除去するために、リソグラフィーシステムにフィルターを設置する方法もあるが工程上複雑になるという課題がある。
一方、EUVレジストの上層にEUVレジスト上層膜を被覆する際に、EUVレジスト膜とEUVレジスト上層膜とのインターミキシング(層の混合)を防止するために、EUVレジスト上層膜形成時に用いる溶剤として、EUVレジストの溶剤を避けて、例えばアルコール系溶剤を用いることがあり、EUVレジスト上層膜材料にはアルコール系溶剤への高い溶解性も求められる。
こうした事情を鑑み、本発明者らは、EUVレジスト上層膜に用いられるポリマーとして、200〜240nm付近のDUV光を選択的に効率よく吸収するナフタレン環を含むポリマーを選択し、また、該ポリマーにおいて、アルコール溶剤への溶解性を高めるためヒドロキシ基、カルボキシル基、スルホ基やこれらの基を含む有機基からなる親水性基を含めるものとすることにより、帯域外光放射の影響を抑制し且つアルコール系溶剤に対して高い溶解性を有するEUVレジスト上層膜形成組成物を完成させるに至った。
しかも本発明の組成物より形成されるEUVレジスト上層膜は、その材料であるポリマーにヒドロキシ基、カルボキシル基、スルホ基やこれらの基を含む有機基からなる親水性基を有することで、現像液(例えば、アルカリ性現像液)に溶解可能であるため、露光後の現像時にEUVレジストと共に現像液による溶解除去が可能である。
以下、本発明を詳細に説明する。
上記EUVレジスト上層膜形成組成物は、ナフタレン環を含む樹脂及び溶剤を含有し、更に架橋剤、架橋触媒、界面活性剤を含むことができる。
上記樹脂のEUVレジスト上層膜形成組成物における含有量は、固形分中で20質量%以上、例えば20〜100質量%、又は30〜100質量%、又は50〜90質量%、又は60〜80質量%である。
Ar1はベンゼン環又はアントラセン環を表す。
n1及びn2はそれぞれ0乃至6の整数を表し、n3及びn4はそれぞれ0乃至ベンゼン環又はアントラセン環に置換し得る最大の整数(ベンゼン環:4、アントラセン環:8)を表す。但し(n1)又は(n1+n3)は少なくとも1である。少なくとも1とは例えば、1、2、3、又は4とすることができる。
なお、n1、n2、n3、n4が2以上の整数を表す場合、R1、R2、R3、R4はそれぞれ同一の基であってもよいし、異なる基であってもよい。
n5及びn6はそれぞれ0乃至7の整数を表し、n8及びn9はそれぞれ0乃至5の整数を表す。但し、(n5)、(n5+n8)、(n5+n11)、又は(n5+n8+n11)は少なくとも1を表す。少なくとも1とは例えば、1、2、3、又は4とすることができる。
なお、n5、n6、n7、n8が2以上の整数を表す場合、R5、R6、R7、R8はそれぞれ同一の基であってもよいし、異なる基であってもよい。
Tは単結合、又はエーテル基(−O−)、エステル基(−(CO)O−)、カルボニル基(−(CO)−)、アミド基(−(CO)−(NH)−)を表すか、又はこれらの基のうち少なくとも一つの基を含む二価の有機基を表す。
R1及びR3における一価の有機基とは、下記に例示される炭素原子数1〜10のアルキル基、炭素原子数2〜10のアルケニル基、フェニル基等において、ヒドロキシ基、カルボキシル基、スルホ基、又はこれらの基のうち少なくとも一つの基を含む一価の有機基を含むものである。
R5、R8及びR11における一価の有機基とは、下記に例示される炭素原子数1〜10のアルキル基、炭素原子数2〜10のアルケニル基、フェニル基において、ヒドロキシ基、カルボキシル基、スルホ基、又はこれらの基のうち少なくとも一つの基を含む一価の有機基を含むものである。
これらその他の溶剤は、前記アルコール系溶剤に対して0.01〜10.00質量%の割合で含有させることができる。
酸化合物としては、例えばスルホン酸化合物又はスルホン酸エステル化合物を好適に使用可能である。
好ましい酸発生剤としては、例えば、ビス(4−tert−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムトリフルオロメタンスルホネート等のオニウム塩系酸発生剤類(例えばヨードニウム塩系酸発生剤、スルホニウム塩系酸発生剤)、フェニル−ビス(トリクロロメチル)−s−トリアジン等のハロゲン含有化合物系酸発生剤類、ベンゾイントシレート、N−ヒドロキシスクシンイミドトリフルオロメタンスルホネート等のスルホン酸系酸発生剤類等が挙げられる。
これらのレオロジー調整剤は、EUVレジスト上層膜形成組成物の全組成物100質量%に対して通常30質量%未満の割合で配合される。
これらの界面活性剤の配合量は、本発明のレジスト上層膜形成組成物の全組成物100質量%当たり通常0.2質量%以下、好ましくは0.1質量%以下である。これらの界面活性剤は単独で添加してもよいし、また2種以上の組合せで添加することもできる。
なお上記露光はEUV(波長13.5nm)光により行われる。
ナフトールノボラック樹脂(1−ナフトール:フェノール=50:50のモル比でホルムアルデヒドと反応しノボラック樹脂を合成した。この樹脂は、前述の式(7−2)に記載される構造単位を含む樹脂に相当する。重量平均分子量は3,200である。)1gを4−メチル−2−ペンタノール99gに溶解させ、EUVレジスト上層膜形成組成物(溶液)を得た。
ナフトールノボラック樹脂(1−ナフトール:フェノール=70:30のモル比でホルムアルデヒドと反応しノボラック樹脂を合成した。この樹脂は、前述の式(7−2)に記載される構造単位を含む樹脂に相当する。重量平均分子量は2,800である。)1gを4−メチル−2−ペンタノール99gに溶解させ、EUVレジスト上層膜形成組成物(溶液)を得た。
ビニルナフタレン含有樹脂(2−ビニルナフタレン:ヒドロキシスチレン:メタクリル酸=50:20:30の質量比でラジカル重合した。この樹脂は、前述の式(8−4)に記載される構造単位を含む樹脂に相当する。重量平均分子量は5,800である。)1gを4−メチル−2−ペンタノール99gに溶解させ、EUVレジスト上層膜形成組成物(溶液)を得た。
ポリヒドロキシスチレン樹脂(市販品。重量平均分子量は8,000)1gを4−メチル−2−ペンタノール99gに溶解させ、EUVレジスト上層膜形成組成物(溶液)を得た。
EUVレジスト溶液(メタクリル系レジスト)をスピナーを用いて塗布した。ホットプレート上で、100℃で1分間加熱することによりレジスト膜を形成し、膜厚測定を行なった(膜厚A:レジスト膜厚)。
そのレジスト上層膜上に市販の現像液(東京応化工業(株)製、製品名:NMD−3)を液盛りして60秒放置し、3,000rpmで回転させながら、30秒間純水でリンスを行った。リンス後、100℃で60秒間ベークし、膜厚測定を行なった(膜厚C)。得られた結果を表1に示す。
膜厚Aが膜厚Cに等しい場合、レジストとインターミキシングがないと言える。
本発明の実施例1乃至実施例3で調製されたレジスト上層膜形成組成物(溶液)、及び比較例1で示したレジスト上層膜形成組成物(溶液)を、それぞれスピナーを用いて石英基板上に塗布した。ホットプレート上で、100℃で1分間加熱し、レジスト上層膜(膜厚0.03μm)を形成した。そして、これら4種類のレジスト上層膜を、分光光度計を用い、波長190nm〜240nmでの透過率を測定した。測定結果を図1に示す。
さらに詳細には、図1に示すように、実施例1乃至実施例3のレジスト上層膜形成組成物を用いて形成された膜は波長220nm〜240nmの光の透過率が40%を下回り、特に実施例1及び実施例2のレジスト上層膜形成組成物を用いて形成された膜にいたっては、波長200nm〜240nmに渡って光の透過率が40%を下回り、DUV光の遮光性が特に良好であるとする結果が得られた。
Claims (10)
- 主鎖又は側鎖にナフタレン環を含む樹脂及び溶剤を含む、EUVリソグラフィー工程に用いるEUVレジスト上層膜形成組成物。
- 樹脂が親水性基としてヒドロキシ基、カルボキシル基、スルホ基、又はこれらの基のうち少なくとも一つの基を含む一価の有機基を含むものである、請求項1に記載のEUVレジスト上層膜形成組成物。
- 樹脂が式(1)で表される単位構造、又は、式(1)及び式(2)で表される単位構造を含む、請求項1又は請求項2に記載のEUVレジスト上層膜形成組成物。:
- 樹脂が式(3)で表される単位構造、又は、式(3)及び式(4)で表される単位構造、又は、式(3)及び式(5)で表される単位構造、又は、式(3)及び式(4)及び式(5)で表される単位構造、又は、式(3)及び式(5)及び式(6)で表される単位構造、又は、式(3)及び式(4)及び式(5)及び式(6)で表される単位構造を含む、請求項1又は請求項2に記載のEUVレジスト上層膜形成組成物。:
- 溶剤がアルコール系溶剤である、請求項1乃至請求項4のいずれか1項に記載のEUVレジスト上層膜形成組成物。
- 更に酸化合物を含む、請求項1乃至請求項5のいずれか1項に記載のEUVレジスト上層膜形成組成物。
- 酸化合物がスルホン酸化合物又はスルホン酸エステル化合物である、請求項6に記載のEUVレジスト上層膜形成組成物。
- 酸化合物がヨードニウム塩系酸発生剤又はスルホニウム塩系酸発生剤である、請求項6に記載のEUVレジスト上層膜形成組成物。
- 基板上にEUVレジスト膜を形成する工程、
該レジスト膜上に請求項1乃至請求項8のいずれか1項に記載のEUVレジスト上層膜形成組成物を塗布し焼成してEUVレジスト上層膜を形成する工程、
該レジスト上層膜とレジスト膜で被覆された半導体基板を露光する工程、
露光後に現像し該レジスト上層膜とレジスト膜を除去する工程、
を含む半導体装置の製造方法。 - 露光がEUV(波長13.5nm)光により行われる、請求項9に記載の半導体装置の製造方法。
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JP4888655B2 (ja) * | 2006-08-11 | 2012-02-29 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
JP2008198788A (ja) | 2007-02-13 | 2008-08-28 | Toshiba Corp | レジストパターン形成方法 |
JP5067537B2 (ja) | 2007-03-02 | 2012-11-07 | 日産化学工業株式会社 | 多核フェノールを含むレジスト下層膜形成組成物 |
JP4910829B2 (ja) * | 2007-03-28 | 2012-04-04 | Jsr株式会社 | 上層反射防止膜形成用組成物及びレジストパターン形成方法 |
JP4590431B2 (ja) * | 2007-06-12 | 2010-12-01 | 富士フイルム株式会社 | パターン形成方法 |
JP4993139B2 (ja) * | 2007-09-28 | 2012-08-08 | 信越化学工業株式会社 | 反射防止膜形成材料、反射防止膜及びこれを用いたパターン形成方法 |
JP2009164441A (ja) | 2008-01-09 | 2009-07-23 | Panasonic Corp | パターン形成方法 |
JP5520489B2 (ja) * | 2009-01-07 | 2014-06-11 | 富士フイルム株式会社 | リソグラフィ用基板被覆方法、及び該方法に用いられる感活性光線または感放射線性樹脂組成物 |
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TWI586716B (zh) | 2017-06-11 |
CN103168274A (zh) | 2013-06-19 |
KR101915138B1 (ko) | 2018-11-06 |
US11675269B2 (en) | 2023-06-13 |
JP6004179B2 (ja) | 2016-10-05 |
CN103168274B (zh) | 2016-07-06 |
WO2012053302A1 (ja) | 2012-04-26 |
US20130209940A1 (en) | 2013-08-15 |
TW201224010A (en) | 2012-06-16 |
KR20130129917A (ko) | 2013-11-29 |
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