JP2017076049A - 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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- JP2017076049A JP2017076049A JP2015203421A JP2015203421A JP2017076049A JP 2017076049 A JP2017076049 A JP 2017076049A JP 2015203421 A JP2015203421 A JP 2015203421A JP 2015203421 A JP2015203421 A JP 2015203421A JP 2017076049 A JP2017076049 A JP 2017076049A
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- 239000000463 material Substances 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 23
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 19
- -1 t -Butoxycarbonyl group Chemical group 0.000 claims description 112
- 239000002253 acid Substances 0.000 claims description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
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- 125000004185 ester group Chemical group 0.000 claims description 32
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- 238000004090 dissolution Methods 0.000 claims description 15
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- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
1.下記式(A)で表されるスルホニウム塩又はヨードニウム塩、及びベースポリマーを含むレジスト材料。
R3は、炭素数1〜24の直鎖状、分岐状又は環状のアルキレン基であり、ヒドロキシ基、アルコキシ基、エーテル基、エステル基、スルホン酸エステル基、シアノ基、ハロゲン原子、二重結合、三重結合又は芳香族基を含んでいてもよい。A+は、下記式(B)で表されるスルホニウムカチオン又は下記式(C)で表されるヨードニウムカチオンである。
2.更に、スルホン酸、イミド酸又はメチド酸を発生する酸発生剤を含む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.前記ベースポリマーが、下記式(a1)で表される繰り返し単位又は下記式(a2)で表される繰り返し単位を含むものである1〜3のいずれかのレジスト材料。
5.更に、溶解阻止剤を含有するものである4のレジスト材料。
6.化学増幅ポジ型レジスト材料である4又は5のレジスト材料。
7.前記ベースポリマーが、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。
8.更に、架橋剤を含有するものである7のレジスト材料。
9.化学増幅ネガ型レジスト材料である7又は8のレジスト材料。
10.前記ベースポリマーが、更に下記式(f1)〜(f3)で表される繰り返し単位から選ばれる少なくとも1つの繰り返し単位を含む1〜9のいずれかのレジスト材料。
11.更に、界面活性剤を含む1〜10のいずれかのレジスト材料。
12.1〜11のいずれかのレジスト材料を基板上に塗布する工程と、加熱処理後、高エネルギー線で露光する工程と、現像液を用いて現像する工程とを含むパターン形成方法。
13.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12のパターン形成方法。
14.前記高エネルギー線が、EB又は波長3〜15nmのEUVである12のパターン形成方法。
本発明のレジスト材料は、環状炭化水素基で置換されたアミノ基を含むスルホン酸のスルホニウム塩又はヨードニウム塩、及びベースポリマーを含む。前記スルホニウム塩又はヨードニウム塩は、光照射によって環状炭化水素基で置換されたアミノ基を含むスルホン酸を発生する酸発生剤であるが、窒素原子を含むためクエンチャーとして機能する。前記スルホン酸は酸不安定基の脱保護反応を引き起こす程の酸性度はないため、後述するように、別途酸不安定基の脱保護反応を引き起こすために強酸であるα位がフッ素化されたスルホン酸、イミド酸又はメチド酸を発生させる酸発生剤を添加することが有効である。なお、α位がフッ素化されたスルホン酸、イミド酸又はメチド酸を発生させる酸発生剤は添加型でもよいが、ベースポリマーに結合しているバウンド型でもよい。
本発明のレジスト材料に含まれるベースポリマーは、ポジ型レジスト材料の場合、酸不安定基を含む繰り返し単位を含む。酸不安定基を含む繰り返し単位としては、下記式(a1)で表される繰り返し単位(以下、繰り返し単位a1という。)、又は式(a2)で表される繰り返し単位(以下、繰り返し単位a2という。)が好ましい。
式(A)で表されるスルホニウム塩又はヨードニウム塩、及び前記ベースポリマーを含むレジスト材料に酸発生剤を添加することで、化学増幅ポジ型レジスト材料あるいは化学増幅ネガ型レジスト材料として機能させることができる。前記酸発生剤としては、例えば、活性光線又は放射線に感応して酸を発生する化合物(光酸発生剤)が挙げられる。光酸発生剤としては、高エネルギー線照射により酸を発生する化合物であればいかなるものでも構わないが、スルホン酸、イミド酸又はメチド酸を発生するものが好ましい。好適な光酸発生剤としてはスルホニウム塩、ヨードニウム塩、スルホニルジアゾメタン、N−スルホニルオキシイミド、オキシム−O−スルホネート型酸発生剤等がある。光酸発生剤の具体例としては、特開2008−111103号公報の段落[0122]〜[0142]に記載されているものが挙げられる。
式(A)で表されるスルホニウム塩又はヨードニウム塩、ベースポリマー及び酸発生剤を含む化学増幅ポジ型レジスト材料あるいは化学増幅ネガ型レジスト材料に、有機溶剤、界面活性剤、溶解阻止剤、架橋剤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、酸発生剤を含有させ、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。
下記実施例で用いた式(A)で表されるスルホニウム塩又はヨードニウム塩(クエンチャー1〜13)の構造を以下に示す。クエンチャー1〜13は、それぞれ対応するスルホニウムクロリド又はヨードニウムクロリドと、環状炭化水素基で置換されたアミノ基を含むスルホン酸とのイオン交換反応によって合成した。
各モノマーを組み合わせてテトラヒドロフラン溶剤下で共重合反応を行い、メタノールに晶出し、更にヘキサンで洗浄を繰り返した後に単離、乾燥して、以下に示す組成のベースポリマー(ポリマー1〜6)を得た。得られたベースポリマーの組成は1H−NMRによって、Mw及び分子量分布はGPC(溶剤:THF)によって確認した。
界面活性剤として住友スリーエム(株)製界面活性剤FC−4430を100ppm溶解させた溶剤に、表1及び2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ろ過して、ポジ型レジスト材料及びネガ型レジスト材料を調製した。
ポリマー1〜6(前記構造式参照)
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)
GBL(γ−ブチロラクトン)
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)
CyP(シクロペンタノン)
[実施例1−1〜1−13、比較例1−1〜1−4]
表1に示すレジスト材料を、シリコンウエハーに信越化学工業(株)製スピンオンカーボン膜ODL-102(カーボンの含有量が80質量%)を200nm、その上にケイ素含有スピンオンハードマスクSHB-A940(珪素の含有量が43質量%)を35nmの膜厚で成膜したトライレイヤープロセス用の基板上にスピンコーティングし、ホットプレートを用いて100℃で60秒間ベークし、レジスト膜の厚みを80nmにした。これをArFエキシマレーザースキャナー((株)ニコン製NSR-S610C、NA1.30、σ0.98/0.78、35度クロスポール照明、Azimuthally偏光照明、6%ハーフトーン位相シフトマスク)を用いて、ウエハー上寸法が60nmライン、200nmピッチのマスクを用いて露光し、表1に記載の温度で60秒間PEBを行い、連続して酢酸n−ブチルで30秒間現像を行って、寸法が60nmスペース、200nmピッチのトレンチのネガパターンを形成した。次に、前記露光とPEBまでは同様に行い、24時間ウエハーをFOUP内に23℃で保管した後に酢酸n−ブチルで30秒間現像を行って、200nmピッチのトレンチのネガ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(CG-4000)でトレンチパターンの寸法を測長し、現像まで連続して形成したトレンチパターンの寸法から、PEB後に24時間放置して形成したトレンチパターンの寸法を引いた値をPPD寸法とした。結果を表1に示す。
[実施例2−1〜2−5、比較例2−1〜2−2]
表2中に示されるレジスト材料を、ヘキサメチルジシラザンベーパープライム処理したSi基板上にスピンコートし、ホットプレートを用いて110℃で60秒間プリベークして80nmのレジスト膜を作製した。これに、(株)日立製作所製HL-800Dを用いて加速電圧50kVで真空チャンバー内描画を行った。描画後、直ちにホットプレート上90℃で60秒間PEBを行い、2.38質量%のテトラメチルアンモニウムヒドロキシドの水溶液で30秒間現像を行ってパターンを得た。
得られたレジストパターンについて次の評価を行った。
ポジ型レジスト膜の場合、120nmのトレンチを寸法通りで解像する露光量における最小のトレンチの寸法を解像力とした。ネガ型レジスト膜の場合、120nmの孤立ラインを寸法通りで解像する露光量における最小の孤立ラインの寸法を解像力とした。なお、実施例2−1〜2−4及び比較例2−1〜2−2はポジ型レジスト材料、実施例2−5はネガ型レジスト材料である。
結果を表2に示す。
Claims (14)
- 下記式(A)で表されるスルホニウム塩又はヨードニウム塩、及びベースポリマーを含むレジスト材料。
R3は、炭素数1〜24の直鎖状、分岐状又は環状のアルキレン基であり、ヒドロキシ基、アルコキシ基、エーテル基、エステル基、スルホン酸エステル基、シアノ基、ハロゲン原子、二重結合、三重結合又は芳香族基を含んでいてもよい。A+は、下記式(B)で表されるスルホニウムカチオン又は下記式(C)で表されるヨードニウムカチオンである。
- 更に、スルホン酸、イミド酸又はメチド酸を発生する酸発生剤を含む請求項1記載のレジスト材料。
- 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。
- 更に、溶解阻止剤を含有するものである請求項4記載のレジスト材料。
- 化学増幅ポジ型レジスト材料である請求項4又は5記載のレジスト材料。
- 前記ベースポリマーが、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、架橋剤を含有するものである請求項7記載のレジスト材料。
- 化学増幅ネガ型レジスト材料である請求項7又は8記載のレジスト材料。
- 前記ベースポリマーが、更に下記式(f1)〜(f3)で表される繰り返し単位から選ばれる少なくとも1つの繰り返し単位を含む請求項1〜9のいずれか1項記載のレジスト材料。
- 更に、界面活性剤を含む請求項1〜10のいずれか1項記載のレジスト材料。
- 請求項1〜11のいずれか1項記載のレジスト材料を基板上に塗布する工程と、加熱処理後、高エネルギー線で露光する工程と、現像液を用いて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12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12記載のパターン形成方法。
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TW201716865A (zh) | 2017-05-16 |
JP6477407B2 (ja) | 2019-03-06 |
KR102154888B1 (ko) | 2020-09-10 |
US10509314B2 (en) | 2019-12-17 |
TWI599845B (zh) | 2017-09-21 |
US20170108774A1 (en) | 2017-04-20 |
KR20170044604A (ko) | 2017-04-25 |
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