KR102915541B1 - 중합체, 레지스트 조성물, 패턴이 형성된 기판의 제조 방법, 그리고 (메트)아크릴산에스테르 및 그 제조 방법 - Google Patents

중합체, 레지스트 조성물, 패턴이 형성된 기판의 제조 방법, 그리고 (메트)아크릴산에스테르 및 그 제조 방법

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KR102915541B1
KR102915541B1 KR1020217029891A KR20217029891A KR102915541B1 KR 102915541 B1 KR102915541 B1 KR 102915541B1 KR 1020217029891 A KR1020217029891 A KR 1020217029891A KR 20217029891 A KR20217029891 A KR 20217029891A KR 102915541 B1 KR102915541 B1 KR 102915541B1
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meth
polymer
acrylic acid
molecular weight
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KR20210144702A (ko
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가즈아키 무카이
다케루 조
요시히로 가몬
사토시 사쿠마
류이치 안사이
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미쯔비시 케미컬 주식회사
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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
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • 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
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
KR1020217029891A 2019-03-27 2020-03-25 중합체, 레지스트 조성물, 패턴이 형성된 기판의 제조 방법, 그리고 (메트)아크릴산에스테르 및 그 제조 방법 Active KR102915541B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JPJP-P-2019-059909 2019-03-27
JPJP-P-2019-059910 2019-03-27
JP2019059910 2019-03-27
JPJP-P-2019-060490 2019-03-27
JP2019059909 2019-03-27
JP2019060490 2019-03-27
PCT/JP2020/013457 WO2020196667A1 (ja) 2019-03-27 2020-03-25 重合体、レジスト組成物、パターンが形成された基板の製造方法、並びに（メタ）アクリル酸エステル及びその製造方法

Publications (2)

Publication Number Publication Date
KR20210144702A KR20210144702A (ko) 2021-11-30
KR102915541B1 true KR102915541B1 (ko) 2026-01-20

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KR1020217029891A Active KR102915541B1 (ko) 2019-03-27 2020-03-25 중합체, 레지스트 조성물, 패턴이 형성된 기판의 제조 방법, 그리고 (메트)아크릴산에스테르 및 그 제조 방법

Country Status (6)

Country Link
US (2) US11845822B2 (https=)
JP (3) JPWO2020196667A1 (https=)
KR (1) KR102915541B1 (https=)
CN (1) CN113614073B (https=)
TW (2) TW202500605A (https=)
WO (1) WO2020196667A1 (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7546353B2 (ja) * 2019-12-11 2024-09-06 東京応化工業株式会社 レジスト組成物及びレジストパターン形成方法
JP2022146199A (ja) * 2021-03-22 2022-10-05 三菱ケミカル株式会社 共重合体、共重合体の製造方法、レジスト組成物及び基板の製造方法
US20240175814A1 (en) * 2021-03-31 2024-05-30 Maruzen Petrochemical Co., Ltd. Method for evaluating resist polymer
CN117024402A (zh) * 2023-08-11 2023-11-10 海南百迈科医疗科技股份有限公司 一种降低α-氰基丙烯酸酯医用胶聚合热的添加剂的制备方法和应用

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001201868A (ja) 1999-11-09 2001-07-27 Mitsubishi Rayon Co Ltd レジスト用モノマーおよびその精製方法
JP2004315464A (ja) 2003-04-18 2004-11-11 Mitsubishi Gas Chem Co Inc アダマンチルアクリレート類の製造方法
WO2005111097A1 (ja) 2004-05-18 2005-11-24 Idemitsu Kosan Co., Ltd. アダマンタン誘導体、その製造方法及びフォトレジスト用感光材料
JP2007153763A (ja) 2005-12-01 2007-06-21 Mitsubishi Rayon Co Ltd ３−ヒドロキシスルフォランおよびそのエステルの製造方法
JP2008521039A (ja) 2004-11-22 2008-06-19 エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション 深紫外線（ｄｅｅｐｕｖ）用のフォトレジスト組成物及びその方法
JP2009196844A (ja) 2008-02-20 2009-09-03 Ngk Insulators Ltd 結晶粒子の製造方法
JP2011184390A (ja) 2010-03-10 2011-09-22 Kuraray Co Ltd アクリル酸エステル誘導体、高分子化合物およびフォトレジスト組成物
JP2012150170A (ja) 2011-01-17 2012-08-09 Jsr Corp 感放射線性樹脂組成物、パターン形成方法、重合体及び化合物
JP2012234166A (ja) 2011-04-19 2012-11-29 Sumitomo Chemical Co Ltd レジスト組成物及びレジストパターンの製造方法
JP2012252244A (ja) * 2011-06-06 2012-12-20 Sumitomo Chemical Co Ltd レジスト組成物及びレジストパターン製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257319A (en) * 1963-01-21 1966-06-21 Union Carbide Corp Copolymers of 3-hydroxytetrahydrothiophene-1, 1-dioxide and their use as oil additives
US20080074753A1 (en) * 2005-01-12 2008-03-27 Mitsubishi Rayon Co., Ltd. Compound, Polymer and Optical Component
JP5248138B2 (ja) * 2008-02-22 2013-07-31 株式会社クラレ 新規なアクリル酸エステル誘導体、およびその製造方法
JP2012153662A (ja) 2011-01-27 2012-08-16 Sumitomo Chemical Co Ltd 酸発生剤用の塩、レジスト組成物及びレジストパターンの製造方法

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001201868A (ja) 1999-11-09 2001-07-27 Mitsubishi Rayon Co Ltd レジスト用モノマーおよびその精製方法
JP2004315464A (ja) 2003-04-18 2004-11-11 Mitsubishi Gas Chem Co Inc アダマンチルアクリレート類の製造方法
WO2005111097A1 (ja) 2004-05-18 2005-11-24 Idemitsu Kosan Co., Ltd. アダマンタン誘導体、その製造方法及びフォトレジスト用感光材料
JP2008521039A (ja) 2004-11-22 2008-06-19 エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション 深紫外線（ｄｅｅｐｕｖ）用のフォトレジスト組成物及びその方法
JP2007153763A (ja) 2005-12-01 2007-06-21 Mitsubishi Rayon Co Ltd ３−ヒドロキシスルフォランおよびそのエステルの製造方法
JP2009196844A (ja) 2008-02-20 2009-09-03 Ngk Insulators Ltd 結晶粒子の製造方法
JP2011184390A (ja) 2010-03-10 2011-09-22 Kuraray Co Ltd アクリル酸エステル誘導体、高分子化合物およびフォトレジスト組成物
JP2012150170A (ja) 2011-01-17 2012-08-09 Jsr Corp 感放射線性樹脂組成物、パターン形成方法、重合体及び化合物
JP2012234166A (ja) 2011-04-19 2012-11-29 Sumitomo Chemical Co Ltd レジスト組成物及びレジストパターンの製造方法
JP2012252244A (ja) * 2011-06-06 2012-12-20 Sumitomo Chemical Co Ltd レジスト組成物及びレジストパターン製造方法

Also Published As

Publication number Publication date
TW202039604A (zh) 2020-11-01
US11845822B2 (en) 2023-12-19
US20240092956A1 (en) 2024-03-21
JP2024001025A (ja) 2024-01-09
TW202500605A (zh) 2025-01-01
CN113614073B (zh) 2024-09-24
JP7663111B2 (ja) 2025-04-16
TWI858039B (zh) 2024-10-11
JP2025102982A (ja) 2025-07-08
CN113614073A (zh) 2021-11-05
US12384863B2 (en) 2025-08-12
US20220213243A1 (en) 2022-07-07
JPWO2020196667A1 (https=) 2020-10-01
KR20210144702A (ko) 2021-11-30
WO2020196667A1 (ja) 2020-10-01

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