KR102923916B1 - 화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법 - Google Patents

화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법

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KR102923916B1
KR102923916B1 KR1020217009898A KR20217009898A KR102923916B1 KR 102923916 B1 KR102923916 B1 KR 102923916B1 KR 1020217009898 A KR1020217009898 A KR 1020217009898A KR 20217009898 A KR20217009898 A KR 20217009898A KR 102923916 B1 KR102923916 B1 KR 102923916B1
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group
carbon atoms
iodine
meth
mac
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KR20210108939A (ko
Inventor
타다시 오마츠
마사히로 마츠모토
미치히로 유리
켄타로 카타오카
타카시 사토
마사토시 에치고
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미쯔비시 가스 케미칼 컴파니, 인코포레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/004—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
    • 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
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
    • 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
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
    • 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
    • G03F7/322—Aqueous alkaline compositions
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Furan Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
KR1020217009898A 2018-12-27 2019-12-23 화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법 Active KR102923916B1 (ko)

Priority Applications (1)

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KR1020267002608A KR20260019026A (ko) 2018-12-27 2019-12-23 화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JPJP-P-2018-244504 2018-12-27
JP2018244504 2018-12-27
JP2019144313 2019-08-06
JPJP-P-2019-144313 2019-08-06
PCT/JP2019/050261 WO2020137935A1 (ja) 2018-12-27 2019-12-23 化合物、（共）重合体、組成物、パターン形成方法、及び化合物の製造方法

Related Child Applications (1)

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KR1020267002608A Division KR20260019026A (ko) 2018-12-27 2019-12-23 화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법

Publications (2)

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KR20210108939A KR20210108939A (ko) 2021-09-03
KR102923916B1 true KR102923916B1 (ko) 2026-02-05

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KR1020267002608A Pending KR20260019026A (ko) 2018-12-27 2019-12-23 화합물, (공)중합체, 조성물, 패턴 형성방법, 및 화합물의 제조방법

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Country Status (6)

Country Link
US (1) US20220119336A1 (https=)
JP (2) JP7579516B2 (https=)
KR (2) KR102923916B1 (https=)
CN (1) CN113227028A (https=)
TW (1) TWI828827B (https=)
WO (1) WO2020137935A1 (https=)

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WO2020137935A1 (ja) * 2018-12-27 2020-07-02 三菱瓦斯化学株式会社 化合物、（共）重合体、組成物、パターン形成方法、及び化合物の製造方法
JP7509071B2 (ja) * 2020-04-28 2024-07-02 信越化学工業株式会社 ヨウ素化芳香族カルボン酸型ペンダント基含有ポリマー、レジスト材料及びパターン形成方法
KR20230012474A (ko) * 2020-05-15 2023-01-26 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 화합물, (공)중합체, 조성물, 레지스트패턴 형성방법, 그리고 화합물 및 (공)중합체의 제조방법
JP7789494B2 (ja) * 2020-06-01 2025-12-22 住友化学株式会社 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法
FR3113904B1 (fr) * 2020-09-08 2022-08-12 Innoverda Procédé de synthèse du 3,5-diiodo-4-hydroxy benzylalcool
CN116615405A (zh) * 2020-12-21 2023-08-18 三菱瓦斯化学株式会社 化合物、聚合物、组合物、膜形成用组合物、图案的形成方法、绝缘膜的形成方法及化合物的制造方法
JP7814674B2 (ja) * 2020-12-21 2026-02-17 三菱瓦斯化学株式会社 化合物、重合体、組成物、膜形成用組成物、パターンの形成方法、絶縁膜の形成方法及び化合物の製造方法
IL310053A (en) * 2021-07-14 2024-03-01 Fujifilm Corp A method for creating a template and a method for manufacturing an electronic device
US20230103685A1 (en) * 2021-09-30 2023-04-06 Rohm And Haas Electronic Materials Llc Iodine-containing acid cleavable compounds, polymers derived therefrom, and photoresist compositions
JPWO2023189586A1 (https=) * 2022-03-29 2023-10-05
KR20240170533A (ko) * 2022-03-31 2024-12-03 니폰 제온 가부시키가이샤 레지스트 조성물 및 레지스트 패턴 형성 방법
JP2023161653A (ja) * 2022-04-26 2023-11-08 東京応化工業株式会社 レジスト組成物、レジストパターン形成方法及び化合物
JP7722257B2 (ja) * 2022-05-10 2025-08-13 信越化学工業株式会社 マスクブランク、レジストパターン形成方法及び化学増幅ポジ型レジスト組成物
CN114755884B (zh) * 2022-06-14 2022-09-16 之江实验室 一种有机无机杂化飞秒激光直写光刻胶
CN115784891B (zh) * 2022-12-14 2024-09-27 吉林化工学院 一种受阻酚类抗氧剂及其制备方法和应用
JPWO2024147288A1 (https=) * 2023-01-06 2024-07-11
WO2024150663A1 (ja) * 2023-01-11 2024-07-18 富士フイルム株式会社 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法
WO2025079648A1 (ja) * 2023-10-11 2025-04-17 三菱瓦斯化学株式会社 化合物、組成物、樹脂組成物、膜形成用組成物、リソグラフィー用膜形成用組成物、レジスト膜形成用組成物
WO2025079631A1 (ja) * 2023-10-11 2025-04-17 三菱瓦斯化学株式会社 組成物、樹脂組成物、膜形成用組成物、リソグラフィー用膜形成用組成物、レジスト膜形成用組成物
CN121941673A (zh) * 2023-10-11 2026-04-28 三菱瓦斯化学株式会社 有机卤素化合物的制造方法、化合物、产酸剂、产碱剂、淬灭剂、聚合物、组合物和抗蚀图案形成方法
TW202535805A (zh) * 2023-10-20 2025-09-16 日商三菱瓦斯化學股份有限公司 含碘（甲基）丙烯酸酯化合物、含碘（甲基）丙烯酸酯（共）聚合物、微影用組合物、阻劑組成物、下層膜形成用組成物及含碘（甲基）丙烯酸酯化合物之製造方法
WO2025154627A1 (ja) * 2024-01-17 2025-07-24 学校法人 関西大学 リソグラフィー下層膜形成組成物、リソグラフィー下層膜、ポジ型レジスト組成物、レジスト膜、及びレジストパターンの形成方法
WO2026054065A1 (ja) * 2024-09-09 2026-03-12 三菱瓦斯化学株式会社 ヨウ素含有（メタ）アクリル酸エステル化合物及びヨウ素・水酸基含有重合体の製造方法

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