WO2009057769A1 - 新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 - Google Patents

新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 Download PDF

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Publication number
WO2009057769A1
WO2009057769A1 PCT/JP2008/069928 JP2008069928W WO2009057769A1 WO 2009057769 A1 WO2009057769 A1 WO 2009057769A1 JP 2008069928 W JP2008069928 W JP 2008069928W WO 2009057769 A1 WO2009057769 A1 WO 2009057769A1
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WIPO (PCT)
Prior art keywords
photoacid generator
generator agent
sulfonic acid
acid salt
carbon atoms
Prior art date
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PCT/JP2008/069928
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English (en)
French (fr)
Inventor
Kazuhiko Maeda
Yoshimi Isono
Satoru Narizuka
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Central Glass Company, Limited
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Publication date
Application filed by Central Glass Company, Limited filed Critical Central Glass Company, Limited
Priority to US12/740,780 priority Critical patent/US8283106B2/en
Publication of WO2009057769A1 publication Critical patent/WO2009057769A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/59—Nitrogen analogues of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/12—Sulfonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Materials For Photolithography (AREA)

Abstract

　下記一般式（Ａ）で示される構造を有する含フッ素スルホン酸塩もしくは、含フッ素スルホン酸基含有化合物が開示されている。 【化１０１】 式中、ｎは１～１０の整数を示す。Ｒは置換もしくは非置換の炭素数１～２０の直鎖状、分岐状又は環状のアルキル基、置換もしくは非置換の炭素数１～２０の直鎖状、分岐状又は環状のアルケニル基、置換もしくは非置換の炭素数６～１５のアリール基又は炭素数４～１５のヘテロアリール基を示す。ａは１又は０である。前記含フッ素スルホン酸塩もしくは含フッ素スルホン酸基含有化合物を含む光酸発生剤はＡｒＦエキシマレーザー光等に対して高感度で、人体蓄積性にも問題がなく、しかも発生する酸（光発生酸）の酸性度が十分高く、かつ、レジスト溶剤に対する高い溶解性及び樹脂に対する優れた相溶性を有する。
PCT/JP2008/069928 2007-11-01 2008-10-31 新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 WO2009057769A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/740,780 US8283106B2 (en) 2007-11-01 2008-10-31 Sulfonic acid salt and derivative thereof, photoacid generator agent, and resist material and pattern formation method using the photoacid generator agent

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-285566 2007-11-01
JP2007285566 2007-11-01

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WO2009057769A1 true WO2009057769A1 (ja) 2009-05-07

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US (1) US8283106B2 (ja)
WO (1) WO2009057769A1 (ja)

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EP2105794A1 (en) * 2008-03-25 2009-09-30 Shin-Etsu Chemical Co., Ltd. Novel photoacid generator, resist composition, and patterning process
SG157293A1 (en) * 2008-05-21 2009-12-29 Korea Kumho Petrochem Co Ltd Acid generating agent for chemically amplified resist compositions
WO2011118824A1 (en) * 2010-03-23 2011-09-29 Fujifilm Corporation Pattern forming method, chemical amplification resist composition and resist film
JP2011201859A (ja) * 2010-03-03 2011-10-13 Sumitomo Chemical Co Ltd 塩及びレジスト組成物
US20110287361A1 (en) * 2010-04-27 2011-11-24 Rohm And Haas Electronic Materials Llc Photoacid generators and photoresists comprising same
JP2011251961A (ja) * 2010-06-01 2011-12-15 Korea Kumho Petrochemical Co Ltd 光酸発生剤、この製造方法、及びこれを含むレジスト組成物
JP2012006908A (ja) * 2010-01-14 2012-01-12 Sumitomo Chemical Co Ltd 塩、フォトレジスト組成物及びレジストパターンの製造方法
US20120040294A1 (en) * 2009-04-21 2012-02-16 Central Glass Company, Limited Top Coating Composition
KR20120023530A (ko) * 2010-07-29 2012-03-13 스미또모 가가꾸 가부시끼가이샤 염 및 포토레지스트 조성물
US20120064459A1 (en) * 2009-05-25 2012-03-15 Central Glass Company, Limited Water Repellent Additive for Immersion Resist
JP2012108495A (ja) * 2010-10-26 2012-06-07 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
JP2012173417A (ja) * 2011-02-18 2012-09-10 Tokyo Ohka Kogyo Co Ltd レジスト組成物、レジストパターン形成方法および高分子化合物
KR20120115137A (ko) * 2011-04-07 2012-10-17 스미또모 가가꾸 가부시키가이샤 레지스트 조성물 및 레지스트 패턴의 제조 방법
US20130183624A1 (en) * 2010-09-09 2013-07-18 Jsr Corporation Radiation-sensitive resin composition
JP2013209360A (ja) * 2012-02-28 2013-10-10 Shin-Etsu Chemical Co Ltd 酸発生剤、化学増幅型レジスト材料、及びパターン形成方法
TWI423948B (zh) * 2010-06-01 2014-01-21 Korea Kumho Petrochem Co Ltd 光酸產生劑及其製造方法，以及含有該光酸產生劑的光阻組合物
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US9104101B2 (en) 2011-02-23 2015-08-11 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern and polymeric compound
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Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8114570B2 (en) 2008-03-25 2012-02-14 Shin-Etsu Chemical Co., Ltd. Photoacid generator, resist composition, and patterning process
EP2105794A1 (en) * 2008-03-25 2009-09-30 Shin-Etsu Chemical Co., Ltd. Novel photoacid generator, resist composition, and patterning process
SG157293A1 (en) * 2008-05-21 2009-12-29 Korea Kumho Petrochem Co Ltd Acid generating agent for chemically amplified resist compositions
US8663903B2 (en) * 2009-04-21 2014-03-04 Central Glass Company, Limited Top coating composition
US20120040294A1 (en) * 2009-04-21 2012-02-16 Central Glass Company, Limited Top Coating Composition
US20120064459A1 (en) * 2009-05-25 2012-03-15 Central Glass Company, Limited Water Repellent Additive for Immersion Resist
KR101334859B1 (ko) * 2009-05-25 2013-11-29 샌트랄 글래스 컴퍼니 리미티드 액침 레지스트용 발수성 첨가제, 발수성 첨가제 함유 레지스트 조성물 및 패턴 형성 방법
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