WO2003035637A1 - 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process - Google Patents

5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process Download PDF

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Publication number
WO2003035637A1
WO2003035637A1 PCT/JP2002/010938 JP0210938W WO03035637A1 WO 2003035637 A1 WO2003035637 A1 WO 2003035637A1 JP 0210938 W JP0210938 W JP 0210938W WO 03035637 A1 WO03035637 A1 WO 03035637A1
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WO
WIPO (PCT)
Prior art keywords
derivatives
polymers
dioxolan
methylene
general formula
Prior art date
Application number
PCT/JP2002/010938
Other languages
English (en)
French (fr)
Inventor
Ryuichi Ansai
Yoshihiro Kamon
Tadayuki Fujiwara
Hideaki Kuwano
Atsushi Ootake
Hikaru Momose
Original Assignee
Mitsubishi Rayon 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 Mitsubishi Rayon Co., Ltd. filed Critical Mitsubishi Rayon Co., Ltd.
Priority to EP02777914.9A priority Critical patent/EP1447403B1/en
Priority to KR1020097021321A priority patent/KR101000596B1/ko
Priority to KR1020047005997A priority patent/KR100943786B1/ko
Priority to US10/492,207 priority patent/US7316884B2/en
Priority to JP2003538153A priority patent/JP4481005B2/ja
Publication of WO2003035637A1 publication Critical patent/WO2003035637A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/42—Halogen atoms or nitro radicals
    • 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
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • 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
    • C08F24/00—Homopolymers and 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 a heterocyclic ring containing oxygen
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/106—Binder containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/106—Binder containing
    • Y10S430/111—Polymer of unsaturated acid or ester
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/143—Electron beam

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
PCT/JP2002/010938 2001-10-23 2002-10-22 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process WO2003035637A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP02777914.9A EP1447403B1 (en) 2001-10-23 2002-10-22 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process
KR1020097021321A KR101000596B1 (ko) 2001-10-23 2002-10-22 5-메틸렌-1,3-디옥솔란-4-온 유도체, 그의 제조방법, 상기 유도체를 중합하여 수득되는 중합체, 레지스트 조성물, 및 패턴 형성 방법
KR1020047005997A KR100943786B1 (ko) 2001-10-23 2002-10-22 5-메틸렌-1,3-디옥솔란-4-온 유도체, 그의 제조방법, 상기유도체를 중합하여 수득되는 중합체, 레지스트 조성물, 및패턴 형성 방법
US10/492,207 US7316884B2 (en) 2001-10-23 2002-10-22 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process
JP2003538153A JP4481005B2 (ja) 2001-10-23 2002-10-22 ５−メチレン−１，３−ジオキソラン−４−オン誘導体、その製造方法、上記誘導体を重合して得られる重合体、レジスト組成物、および、パターン形成方法

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP2001324824 2001-10-23
JP2001/324824 2001-10-23
JP2002006354 2002-01-15
JP2002/6354 2002-01-15
JP2002/159847 2002-05-31
JP2002159847 2002-05-31
JP2002225066 2002-08-01
JP2002/225066 2002-08-01

Publications (1)

Publication Number Publication Date
WO2003035637A1 true WO2003035637A1 (en) 2003-05-01

Family

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Family Applications (1)

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PCT/JP2002/010938 WO2003035637A1 (en) 2001-10-23 2002-10-22 5-methylene-1,3-dioxolan-4-one derivatives, process for their production, polymers of the derivatives, resist compositions, and pattern formation process

Country Status (7)

Country Link
US (1) US7316884B2 (ja)
EP (1) EP1447403B1 (ja)
JP (2) JP4481005B2 (ja)
KR (1) KR100943786B1 (ja)
CN (2) CN100453539C (ja)
TW (1) TWI291953B (ja)
WO (1) WO2003035637A1 (ja)

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JP2007093909A (ja) * 2005-09-28 2007-04-12 Fujifilm Corp ポジ型レジスト組成物及びそれを用いたパターン形成方法
WO2007058345A1 (ja) * 2005-11-21 2007-05-24 Jsr Corporation 感放射線性樹脂組成物
JP2008203588A (ja) * 2007-02-21 2008-09-04 Jsr Corp 感放射線性樹脂組成物、スペーサーとその製法および液晶表示素子
JP2010061117A (ja) * 2008-08-07 2010-03-18 Sumitomo Chemical Co Ltd 化学増幅型ポジ型レジスト組成物
WO2010084997A1 (ja) * 2009-01-26 2010-07-29 国立大学法人徳島大学 立体規則性の高い多官能性ポリマー及びその製造方法
JP2012131988A (ja) * 2010-12-02 2012-07-12 Rohm & Haas Electronic Materials Llc ポリマー、フォトレジスト組成物、およびフォトリソグラフィパターンを形成する方法
JP2012155314A (ja) * 2011-01-07 2012-08-16 Sumitomo Chemical Co Ltd レジスト組成物
WO2012133352A1 (ja) * 2011-03-31 2012-10-04 Jsr株式会社 フォトレジスト組成物
JP2014063150A (ja) * 2012-08-31 2014-04-10 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
JP2015043079A (ja) * 2013-07-24 2015-03-05 Jsr株式会社 感放射線性樹脂組成物、レジストパターン形成方法、重合体、化合物及び化合物の製造方法
JPWO2013047117A1 (ja) * 2011-09-29 2015-03-26 Jsr株式会社 フォトレジスト組成物、レジストパターン形成方法及び重合体
WO2020049963A1 (ja) * 2018-09-07 2020-03-12 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

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JP2007522262A (ja) * 2003-06-26 2007-08-09 シミックス・テクノロジーズ・インコーポレイテッド フォトレジストポリマー
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EP1637928B1 (en) 2004-09-15 2012-05-02 Dongjin Semichem Co., Ltd Photoresist monomer having spiro cyclic ketal group, polymer thereof and photoresist composition including the same
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JP4762630B2 (ja) * 2005-08-03 2011-08-31 東京応化工業株式会社 レジスト組成物およびレジストパターン形成方法
WO2007094474A1 (ja) * 2006-02-17 2007-08-23 Kuraray Co., Ltd. 第３級アルコール誘導体、高分子化合物およびフォトレジスト組成物
US8771924B2 (en) * 2006-12-26 2014-07-08 Fujifilm Corporation Polymerizable composition, lithographic printing plate precursor and lithographic printing method
EP2450746A1 (en) 2007-08-10 2012-05-09 Fujifilm Corporation Positive resist composition and pattern forming method using the composition
US8637623B2 (en) * 2008-02-25 2014-01-28 Daicel Chemical Industries, Ltd. Monomer having electron-withdrawing substituent and lactone skeleton, polymeric compound, and photoresist composition
KR101875983B1 (ko) * 2010-09-30 2018-07-06 제이에스알 가부시끼가이샤 감방사선성 수지 조성물, 중합체 및 화합물
EP2472326A1 (en) * 2010-12-31 2012-07-04 Rohm and Haas Electronic Materials LLC Polymers, photoresist compositions and methods of forming photolithographic patterns
EP2472325A1 (en) * 2010-12-31 2012-07-04 Rohm and Haas Electronic Materials LLC Polymers, photoresist compositions and methods of forming photolithographic patterns
EP2472324A1 (en) 2010-12-31 2012-07-04 Rohm and Haas Electronic Materials LLC Monomers, polymers, photoresist compositions and methods of forming photolithographic patterns
US9256125B2 (en) 2013-03-30 2016-02-09 Rohm And Haas Electronic Materials, Llc Acid generators and photoresists comprising same
JP6319001B2 (ja) * 2014-09-08 2018-05-09 Jsr株式会社 感放射線性樹脂組成物及びレジストパターン形成方法
JP6721823B2 (ja) * 2016-01-05 2020-07-15 Jsr株式会社 感放射線性樹脂組成物、レジストパターン形成方法、重合体及び化合物
JP6969889B2 (ja) * 2016-05-13 2021-11-24 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
WO2019187803A1 (ja) * 2018-03-30 2019-10-03 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
WO2020137918A1 (ja) * 2018-12-28 2020-07-02 富士フイルム株式会社 有機溶剤現像用ネガ型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

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JP4524237B2 (ja) * 2005-09-28 2010-08-11 富士フイルム株式会社 ポジ型レジスト組成物及びそれを用いたパターン形成方法
JP2007093909A (ja) * 2005-09-28 2007-04-12 Fujifilm Corp ポジ型レジスト組成物及びそれを用いたパターン形成方法
WO2007058345A1 (ja) * 2005-11-21 2007-05-24 Jsr Corporation 感放射線性樹脂組成物
JP4821776B2 (ja) * 2005-11-21 2011-11-24 Ｊｓｒ株式会社 感放射線性樹脂組成物
JP2008203588A (ja) * 2007-02-21 2008-09-04 Jsr Corp 感放射線性樹脂組成物、スペーサーとその製法および液晶表示素子
JP2010061117A (ja) * 2008-08-07 2010-03-18 Sumitomo Chemical Co Ltd 化学増幅型ポジ型レジスト組成物
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EP1447403A1 (en) 2004-08-18
US20040248031A1 (en) 2004-12-09
JP4481005B2 (ja) 2010-06-16
CN1413992A (zh) 2003-04-30
JP5243390B2 (ja) 2013-07-24
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