JP6477409B2 - 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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- JP6477409B2 JP6477409B2 JP2015205402A JP2015205402A JP6477409B2 JP 6477409 B2 JP6477409 B2 JP 6477409B2 JP 2015205402 A JP2015205402 A JP 2015205402A JP 2015205402 A JP2015205402 A JP 2015205402A JP 6477409 B2 JP6477409 B2 JP 6477409B2
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- 0 *c(c1c2cccc1)ccc2[S+]1CCCC1 Chemical compound *c(c1c2cccc1)ccc2[S+]1CCCC1 0.000 description 12
- BYRRNRQCSTYVEI-UHFFFAOYSA-N C(C1)c2ccccc2[S+]1c1ccccc1 Chemical compound C(C1)c2ccccc2[S+]1c1ccccc1 BYRRNRQCSTYVEI-UHFFFAOYSA-N 0.000 description 1
- ORWZVTKIPUOMOA-UHFFFAOYSA-N C(CC1)CC[S+]1c1cccc2c1cccc2 Chemical compound C(CC1)CC[S+]1c1cccc2c1cccc2 ORWZVTKIPUOMOA-UHFFFAOYSA-N 0.000 description 1
- LJUUGFPOBHJIAU-UHFFFAOYSA-N C(CC1)C[S+]1c1cccc2c1cccc2 Chemical compound C(CC1)C[S+]1c1cccc2c1cccc2 LJUUGFPOBHJIAU-UHFFFAOYSA-N 0.000 description 1
- PKOBMFUWHOKSBV-UHFFFAOYSA-N C(c1ccccc11)=C[S+]1c1ccccc1 Chemical compound C(c1ccccc11)=C[S+]1c1ccccc1 PKOBMFUWHOKSBV-UHFFFAOYSA-N 0.000 description 1
- ZSPLZIRQNDFLGZ-UHFFFAOYSA-N C=CC(CC1C(CC2)CC2C1)=O Chemical compound C=CC(CC1C(CC2)CC2C1)=O ZSPLZIRQNDFLGZ-UHFFFAOYSA-N 0.000 description 1
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- FUBAYNPDUBRNJU-UHFFFAOYSA-N COc(c1c2cccc1)ccc2[S+]1CCCC1 Chemical compound COc(c1c2cccc1)ccc2[S+]1CCCC1 FUBAYNPDUBRNJU-UHFFFAOYSA-N 0.000 description 1
- IFEFKQUKOFNLRH-UHFFFAOYSA-N COc(c1c2cccc1)ccc2[S+]1CCCCC1 Chemical compound COc(c1c2cccc1)ccc2[S+]1CCCCC1 IFEFKQUKOFNLRH-UHFFFAOYSA-N 0.000 description 1
- GMEXDATVSHAMEP-UHFFFAOYSA-N C[S+](C)c1ccccc1 Chemical compound C[S+](C)c1ccccc1 GMEXDATVSHAMEP-UHFFFAOYSA-N 0.000 description 1
- BJMDYNHSWAKAMX-UHFFFAOYSA-N C[S+](c1ccccc1)c1ccccc1 Chemical compound C[S+](c1ccccc1)c1ccccc1 BJMDYNHSWAKAMX-UHFFFAOYSA-N 0.000 description 1
- KNBFPOQKQHIUHP-UHFFFAOYSA-N C[U]COc(cc1)c(cccc2)c2c1[S+]1CCCCC1 Chemical compound C[U]COc(cc1)c(cccc2)c2c1[S+]1CCCCC1 KNBFPOQKQHIUHP-UHFFFAOYSA-N 0.000 description 1
- FOUUBLMEFLWYOC-UHFFFAOYSA-N Cc1cc([S+](c2ccccc2)c2ccccc2)cc(C)c1 Chemical compound Cc1cc([S+](c2ccccc2)c2ccccc2)cc(C)c1 FOUUBLMEFLWYOC-UHFFFAOYSA-N 0.000 description 1
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- JTOWCKDEJVXWAR-UHFFFAOYSA-N Fc(cc1)ccc1[S+](c1ccccc1)c1ccccc1 Chemical compound Fc(cc1)ccc1[S+](c1ccccc1)c1ccccc1 JTOWCKDEJVXWAR-UHFFFAOYSA-N 0.000 description 1
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- VWDQQWMJANCDBB-UHFFFAOYSA-O Oc(c1c2cccc1)ccc2[S+]1CCCCC1 Chemical compound Oc(c1c2cccc1)ccc2[S+]1CCCCC1 VWDQQWMJANCDBB-UHFFFAOYSA-O 0.000 description 1
- SDCRPEABFMZSKB-UHFFFAOYSA-N [O-][N+](c(cc1)ccc1[S+](c1ccccc1)c1ccccc1)=O Chemical compound [O-][N+](c(cc1)ccc1[S+](c1ccccc1)c1ccccc1)=O SDCRPEABFMZSKB-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
- G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
-
- 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
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
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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
- C08F220/301—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
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
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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(ただし、下記式(A')で表されるスルホニウム塩を除く。)、及びベースポリマーを含むレジスト材料。
2.R 1 が、炭素数1〜24の非置換の直鎖状アルキレン基である1のレジスト材料。
3.R 2 、R 3 及びR 4 の少なくとも1つの基の水素原子の一部又は全部が、エーテル基、エステル基、カルボニル基、カーボネート基、ヒドロキシ基、カルボキシル基、ハロゲン原子、シアノ基、アミド基、ニトロ基、スルトン基、スルホン酸エステル基、スルホン基、チオール基又はスルホニウム塩を含む置換基で置換されたものである1又は2のレジスト材料。
4.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1〜3のいずれかのレジスト材料。
5.更に、有機溶剤を含む1〜4のいずれかのレジスト材料。
6.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1〜5のいずれかのレジスト材料。
7.更に、溶解阻止剤を含有するものである6のレジスト材料。
8.化学増幅ポジ型レジスト材料である6又は7のレジスト材料。
9.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1〜5のいずれかのレジスト材料。
10.更に、架橋剤を含有するものである9のレジスト材料。
11.化学増幅ネガ型レジスト材料である9又は10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つの繰り返し単位を含む1〜11のいずれかのレジスト材料。
13.更に、界面活性剤を含む1〜12のいずれかのレジスト材料。
14.1〜13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。
15.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14のパターン形成方法。
16.前記高エネルギー線が、EB又は波長3〜15nmのEUVである14のパターン形成方法。
本発明のレジスト材料は、モルホリ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、光照射によってモルホリ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、モルホリ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 (16)
- 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(ただし、下記式(A')で表されるスルホニウム塩を除く。)、及びベースポリマーを含むレジスト材料。
- R 1 が、炭素数1〜24の非置換の直鎖状アルキレン基である請求項1記載のレジスト材料。
- R 2 、R 3 及びR 4 の少なくとも1つの基の水素原子の一部又は全部が、エーテル基、エステル基、カルボニル基、カーボネート基、ヒドロキシ基、カルボキシル基、ハロゲン原子、シアノ基、アミド基、ニトロ基、スルトン基、スルホン酸エステル基、スルホン基、チオール基又はスルホニウム塩を含む置換基で置換されたものである請求項1又は2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1〜3のいずれか1項記載のレジスト材料。
- 更に、有機溶剤を含む請求項1〜4のいずれか1項記載のレジスト材料。
- 更に、溶解阻止剤を含有するものである請求項6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6又は7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1〜5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9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9又は10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1〜11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1〜12のいずれか1項記載のレジスト材料。
- 請求項1〜13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14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14記載のパターン形成方法。
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US15/296,662 US10620533B2 (en) | 2015-10-19 | 2016-10-18 | Resist composition and patterning process |
KR1020160135023A KR102382929B1 (ko) | 2015-10-19 | 2016-10-18 | 레지스트 재료 및 패턴 형성 방법 |
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JP2000089454A (ja) * | 1998-09-14 | 2000-03-31 | Tokyo Ohka Kogyo Co Ltd | ネガ型レジスト組成物 |
JP3751518B2 (ja) | 1999-10-29 | 2006-03-01 | 信越化学工業株式会社 | 化学増幅レジスト組成物 |
US6673511B1 (en) | 1999-10-29 | 2004-01-06 | Shin-Etsu Chemical Co., Ltd. | Resist composition |
US6749987B2 (en) * | 2000-10-20 | 2004-06-15 | Fuji Photo Film Co., Ltd. | Positive photosensitive composition |
JP4320520B2 (ja) | 2000-11-29 | 2009-08-26 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
KR100670090B1 (ko) | 2000-11-29 | 2007-01-17 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 아민 화합물, 레지스트 재료 및 패턴 형성 방법 |
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JP6252049B2 (ja) * | 2012-09-11 | 2017-12-27 | 住友化学株式会社 | レジスト組成物及びレジストパターンの製造方法 |
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