JP6645463B2 - 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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- JP6645463B2 JP6645463B2 JP2017052391A JP2017052391A JP6645463B2 JP 6645463 B2 JP6645463 B2 JP 6645463B2 JP 2017052391 A JP2017052391 A JP 2017052391A JP 2017052391 A JP2017052391 A JP 2017052391A JP 6645463 B2 JP6645463 B2 JP 6645463B2
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- 0 *C(C(C(F)(I)I)NC(C*C(C(*)=C)=O)=O)(*=C)F Chemical compound *C(C(C(F)(I)I)NC(C*C(C(*)=C)=O)=O)(*=C)F 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PAWXAWIFAJUYLR-UHFFFAOYSA-N C1c2ccccc2[S+](c2ccccc2)c2c1cccc2 Chemical compound C1c2ccccc2[S+](c2ccccc2)c2c1cccc2 PAWXAWIFAJUYLR-UHFFFAOYSA-N 0.000 description 2
- RJZQTOSEBVPNDM-UHFFFAOYSA-N CCCC(C)(C(C)(C)CC)C(OC(C)(C)C(C(F)(F)F)(C=[IH])O)=O Chemical compound CCCC(C)(C(C)(C)CC)C(OC(C)(C)C(C(F)(F)F)(C=[IH])O)=O RJZQTOSEBVPNDM-UHFFFAOYSA-N 0.000 description 1
- CDXRRCXHSAOHDT-UHFFFAOYSA-N Cc(cccc1)c1Oc1c(C=[IH])cccc1 Chemical compound Cc(cccc1)c1Oc1c(C=[IH])cccc1 CDXRRCXHSAOHDT-UHFFFAOYSA-N 0.000 description 1
- LRYJCFJFXYEUBF-UHFFFAOYSA-N Cc(cccc1)c1Oc1c(CCc2ccccc2)cccc1 Chemical compound Cc(cccc1)c1Oc1c(CCc2ccccc2)cccc1 LRYJCFJFXYEUBF-UHFFFAOYSA-N 0.000 description 1
- PVAWUWJFFVYPGE-UHFFFAOYSA-N Cc1c(Cc(cccc2)c2[IH]C[IH]c2ccccc2)cccc1 Chemical compound Cc1c(Cc(cccc2)c2[IH]C[IH]c2ccccc2)cccc1 PVAWUWJFFVYPGE-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N c(cc1)ccc1-c1ccccc1 Chemical compound c(cc1)ccc1-c1ccccc1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
Description
1.ベースポリマー、及び下記式(A)で表されるヨードニウム塩を含むクエンチャーを含むレジスト材料。
2.mが、3である1のレジスト材料。
3.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又は2のレジスト材料。
4.更に、有機溶剤を含む1〜3のいずれかのレジスト材料。
5.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1〜4のいずれかのレジスト材料。
6.更に、溶解阻止剤を含む5のレジスト材料。
7.化学増幅ポジ型レジスト材料である5又は6のレジスト材料。
8.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1〜4のいずれかのレジスト材料。
9.更に、架橋剤を含む8のレジスト材料。
10.化学増幅ネガ型レジスト材料である8又は9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.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種を含む1〜11のいずれかのレジスト材料。
13.1〜12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、前記レジスト膜を高エネルギー線で露光する工程と、現像液を用いて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。
14.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13のパターン形成方法。
15.前記高エネルギー線が、EB又は波長3〜15nmのEUVである13のパターン形成方法。
本発明のレジスト材料は、ベースポリマー、及びヨウ素化ベンゼンに結合したフルオロ安息香酸のヨードニウム塩を含むクエンチャーを含む。前記ヨードニウム塩は、光照射によってヨウ素化ベンゼンに結合したフルオロ安息香酸を発生する酸発生剤であるが、強塩基性のヨードニウムを有しているためクエンチャーとして機能する。前記ヨウ素化ベンゼンに結合したフルオロ安息香酸は、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という。)が好ましい。
本発明のレジスト材料は、更に酸発生剤を含んでもよい。酸発生剤を含むことで、化学増幅ポジ型レジスト材料又は化学増幅ネガ型レジスト材料として機能することができる。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。
前述した成分に加えて、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ともに、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。
各々のモノマーを組み合わせてテトラヒドロフラン(THF)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1〜3)を得た。得られたベースポリマーの組成は1H−NMRにより、Mw及び分散度(Mw/Mn)はGPC(溶剤:THF、標準:ポリスチレン)により確認した。
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)
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)
[実施例1−1〜1−8、比較例1−1〜1−7]
表1に示す各レジスト材料を、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(ケイ素の含有量が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、膜厚80nmのレジスト膜を作製した。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50nmライン、100nmピッチのマスクを用いて液浸露光し、表1に記載の温度で60秒間PEBを行った。なお、液浸液としては水を用いた。実施例1−1〜1−7及び比較例1−1〜1−6では、酢酸n−ブチルで30秒間現像を行い、実施例1−8及び比較例1−7では、2.38質量%TMAH水溶液で現像を行い、寸法が50nmスペース、100nmピッチのラインアンドスペース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(CG4000)を用いて、ラインアンドスペースパターンが1:1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、このときのエッジラフネス(LWR)を測定した。結果を表1に示す。
[実施例2−1〜2−11、比較例2−1]
表2に示す各レジスト材料を、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13nm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)を用いて露光し、ホットプレートを用いて表2に記載の温度で60秒間PEBを行い、2.38質量%TMAH水溶液で30秒間現像を行ってピッチ46nm、寸法23nmのホールパターンを形成した。得られたレジストパターンについて次の評価を行った。(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個の寸法バラツキ(CDU、3σ)を求めた。結果を表2に示す。
Claims (15)
- ベースポリマー、及び下記式(A)で表されるヨードニウム塩を含むクエンチャーを含むレジスト材料。
- mが、3である請求項1記載のレジスト材料。
- 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又は2記載のレジスト材料。
- 更に、有機溶剤を含む請求項1〜3のいずれか1項記載のレジスト材料。
- 更に、溶解阻止剤を含む請求項5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5又は6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1〜4のいずれか1項記載のレジスト材料。
- 更に、架橋剤を含む請求項8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8又は9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。
- 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種を含む請求項1〜11のいずれか1項記載のレジスト材料。
- 請求項1〜12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、前記レジスト膜を高エネルギー線で露光する工程と、現像液を用いて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13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13記載のパターン形成方法。
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