JP5442576B2 - 保護ポリマーの脱保護方法 - Google Patents

保護ポリマーの脱保護方法 Download PDF

Info

Publication number
JP5442576B2
JP5442576B2 JP2010228609A JP2010228609A JP5442576B2 JP 5442576 B2 JP5442576 B2 JP 5442576B2 JP 2010228609 A JP2010228609 A JP 2010228609A JP 2010228609 A JP2010228609 A JP 2010228609A JP 5442576 B2 JP5442576 B2 JP 5442576B2
Authority
JP
Japan
Prior art keywords
group
polymer
reaction
deprotection
deprotecting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
JP2010228609A
Other languages
English (en)
Japanese (ja)
Other versions
JP2011102386A (ja
JP2011102386A5 (enExample
Inventor
恵一 増永
武 渡辺
大将 土門
聡 渡邉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Priority to JP2010228609A priority Critical patent/JP5442576B2/ja
Publication of JP2011102386A publication Critical patent/JP2011102386A/ja
Publication of JP2011102386A5 publication Critical patent/JP2011102386A5/ja
Application granted granted Critical
Publication of JP5442576B2 publication Critical patent/JP5442576B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • C08F212/22—Oxygen
    • 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
    • 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
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (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
    • C08F220/1809—C9-(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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/12—Hydrolysis
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • 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
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2010228609A 2009-10-13 2010-10-08 保護ポリマーの脱保護方法 Active JP5442576B2 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2010228609A JP5442576B2 (ja) 2009-10-13 2010-10-08 保護ポリマーの脱保護方法

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2009236353 2009-10-13
JP2009236353 2009-10-13
JP2010228609A JP5442576B2 (ja) 2009-10-13 2010-10-08 保護ポリマーの脱保護方法

Publications (3)

Publication Number Publication Date
JP2011102386A JP2011102386A (ja) 2011-05-26
JP2011102386A5 JP2011102386A5 (enExample) 2011-09-15
JP5442576B2 true JP5442576B2 (ja) 2014-03-12

Family

ID=43064554

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2010228609A Active JP5442576B2 (ja) 2009-10-13 2010-10-08 保護ポリマーの脱保護方法

Country Status (6)

Country Link
US (1) US8273830B2 (enExample)
EP (1) EP2311888B1 (enExample)
JP (1) JP5442576B2 (enExample)
KR (1) KR101603797B1 (enExample)
CN (1) CN102040700B (enExample)
TW (1) TWI428380B (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102324819B1 (ko) 2014-12-12 2021-11-11 삼성전자주식회사 포토레지스트용 고분자, 포토레지스트 조성물, 패턴 형성 방법 및 반도체 장치의 제조 방법
CN105924553B (zh) * 2016-05-16 2018-07-20 张智斌 一种分子量窄分布的聚羟基苯乙烯类聚合物的制备方法
TW202518588A (zh) 2019-08-09 2025-05-01 日商丸善石油化學股份有限公司 聚合物及其製造方法，及阻劑用樹脂組成物
JP2023107363A (ja) * 2022-01-24 2023-08-03 国立大学法人九州大学 接着性材料、物品およびポリマー

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822862A (en) * 1987-01-28 1989-04-18 Hoechst Celanese Corporation Emulsion polymerization of 4-acetoxystyrene and hydrolysis to poly(p-vinylphenol
US4965400A (en) 1987-09-16 1990-10-23 Richard Vicari Preparation of 3,5-disubstituted-4-acetoxystyrene
US4912173A (en) * 1987-10-30 1990-03-27 Hoechst Celanese Corporation Hydrolysis of poly(acetoxystyrene) in aqueous suspension
US4868256A (en) * 1988-08-02 1989-09-19 Hoechst Celanese Process for the production of 3-mono or 3,5-disubstituted-4-acetoxystyrene its polymerization, and hydrolysis
US5264528A (en) * 1990-12-06 1993-11-23 Hoechst Celanese Corporation Process for the preparation of 4-hydroxystyrene polymers from 4-acetoxystyrene polymers
DE69322946T2 (de) * 1992-11-03 1999-08-12 International Business Machines Corp., Armonk, N.Y. Photolackzusammensetzung
JP3712047B2 (ja) * 2000-08-14 2005-11-02 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
JP3796568B2 (ja) 2001-02-21 2006-07-12 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
JP3867778B2 (ja) 2001-07-05 2007-01-10 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
JP3821217B2 (ja) * 2001-10-30 2006-09-13 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
JP4478589B2 (ja) 2005-02-02 2010-06-09 富士フイルム株式会社 ネガ型レジスト組成物及びそれを用いたパターン形成方法
JP4525440B2 (ja) * 2005-04-20 2010-08-18 Ｊｓｒ株式会社 感放射線性樹脂組成物
JP5067523B2 (ja) 2006-03-20 2012-11-07 信越化学工業株式会社 化学増幅ポジ型レジスト材料並びにこれを用いたパターン形成方法
US20080020289A1 (en) * 2006-07-24 2008-01-24 Shin-Etsu Chemical Co., Ltd. Novel polymer, positive resist composition and patterning process using the same
JP5183903B2 (ja) * 2006-10-13 2013-04-17 信越化学工業株式会社 高分子化合物、レジスト材料及びこれを用いたパターン形成方法
JP4678383B2 (ja) * 2007-03-29 2011-04-27 信越化学工業株式会社 化学増幅ネガ型レジスト組成物及びパターン形成方法
JP4984067B2 (ja) 2007-07-23 2012-07-25 信越化学工業株式会社 フォトレジスト組成物用高分子化合物の合成方法

Also Published As

Publication number Publication date
TW201130902A (en) 2011-09-16
JP2011102386A (ja) 2011-05-26
US8273830B2 (en) 2012-09-25
CN102040700B (zh) 2013-06-05
CN102040700A (zh) 2011-05-04
EP2311888B1 (en) 2013-11-20
US20110086986A1 (en) 2011-04-14
EP2311888A1 (en) 2011-04-20
KR20110040698A (ko) 2011-04-20
TWI428380B (zh) 2014-03-01
KR101603797B1 (ko) 2016-03-16

Similar Documents

Publication Publication Date Title
JP7027711B2 (ja) ポジ型レジスト組成物、レジストパターン形成方法、及びフォトマスクブランク
JP5125832B2 (ja) 感放射線性樹脂組成物
JP2013083957A (ja) レジスト組成物及びレジストパターンの製造方法
JP2011074365A (ja) 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
WO2005061566A1 (ja) ハイパーブランチポリマー及びその製造方法、並びに該ハイパーブランチポリマーを含有するレジスト組成物
WO2005108444A1 (ja) ラクトン系共重合体および感放射線性樹脂組成物
WO2015194330A1 (ja) 感放射線性又は感活性光線性樹脂組成物、並びに、それを用いたレジスト膜、マスクブランクス、レジストパターン形成方法、電子デバイスの製造方法、及び電子デバイス
KR20140118928A (ko) 산 발생제 및 이를 포함하는 포토레지스트
KR20140064874A (ko) (메트)아크릴산에스테르 유도체, 고분자 화합물 및 포토레지스트 조성물
TW200419309A (en) Polymer compound, resist composition and dissolution inhibitor agent containing the polymer compound
JP5442576B2 (ja) 保護ポリマーの脱保護方法
JP6472427B2 (ja) 酸に不安定な超分岐コポリマー、及び関連するフォトレジスト組成物、及び電子デバイスを形成する方法
JP5840146B2 (ja) ビニルスルホン酸エステル誘導体、高分子化合物およびフォトレジスト組成物
JP2009221194A (ja) 光酸発生基結合型多価フェノール誘導体、該誘導体の製造方法及び該誘導体を含む電子線用又はｅｕｖ用化学増幅型レジスト組成物
KR20160111908A (ko) (메트)아크릴레이트 화합물, (메트)아크릴 공중합체 및 그것을 함유하는 감광성 수지 조성물
JP2009120612A (ja) 感光性化合物及びそれを含むフォトレジスト組成物
KR101632860B1 (ko) 알코올 화합물과 그 제조 방법, 락톤 화합물의 제조 방법, (메트)아크릴산에스테르와 그 제조 방법, 중합체와 그 제조 방법, 레지스트 조성물과 이것을 사용한 기판의 제조 방법
WO2007020734A1 (ja) ナノ平滑性とエッチング耐性を有するフォトレジストポリマーならびにレジスト組成物
WO2013146379A1 (ja) アクリル酸エステル系誘導体
JP6119283B2 (ja) レジスト組成物及びレジストパターンの製造方法
KR20080037139A (ko) 술포닐기를 포함하는 포토레지스트 모노머, 폴리머 및 이를포함하는 포토레지스트 조성물
US10005714B2 (en) (Meth)acrylic acid ester compound and production method therefor
CN105980347B (zh) 新型脂环式酯化合物的制造方法、新型脂环式酯化合物、将其聚合的(甲基)丙烯酸系共聚物、和包含其的感光性树脂组合物
CN105143291B (zh) 新型脂环式酯化合物、(甲基)丙烯酸类共聚物以及包含它的感光性树脂组合物
JP2013035764A (ja) 化合物、レジスト組成物及びレジストパターンの製造方法

Legal Events

Date Code Title Description
A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20110729

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20121026

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20131120

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20131126

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20131218

R150 Certificate of patent or registration of utility model

Ref document number: 5442576

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

Free format text: JAPANESE INTERMEDIATE CODE: R150