WO2004107051A2 - Photoacid generators with perfluorinated multifunctional anions - Google Patents

Photoacid generators with perfluorinated multifunctional anions Download PDF

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Publication number
WO2004107051A2
WO2004107051A2 PCT/US2004/014348 US2004014348W WO2004107051A2 WO 2004107051 A2 WO2004107051 A2 WO 2004107051A2 US 2004014348 W US2004014348 W US 2004014348W WO 2004107051 A2 WO2004107051 A2 WO 2004107051A2
Authority
WO
WIPO (PCT)
Prior art keywords
photoacid generator
group
groups
acid
ionic
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.)
Ceased
Application number
PCT/US2004/014348
Other languages
English (en)
French (fr)
Other versions
WO2004107051A3 (en
Inventor
William M. Lamanna
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.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to EP04751648.9A priority Critical patent/EP1625447B1/en
Priority to JP2006532863A priority patent/JP4680915B2/ja
Priority to CN200480014082XA priority patent/CN1802607B/zh
Publication of WO2004107051A2 publication Critical patent/WO2004107051A2/en
Priority to KR1020057022224A priority patent/KR101070032B1/ko
Anticipated expiration legal-status Critical
Publication of WO2004107051A3 publication Critical patent/WO2004107051A3/en
Ceased legal-status Critical Current

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
    • G03F7/0045—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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • 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
    • 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
    • Y10S430/114—Initiator containing
    • Y10S430/115—Cationic or anionic
    • 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
    • Y10S430/114—Initiator containing
    • Y10S430/122—Sulfur compound 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
    • Y10S430/114—Initiator containing
    • Y10S430/122—Sulfur compound containing
    • Y10S430/123—Sulfur in heterocyclic ring
    • 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
    • Y10S430/114—Initiator containing
    • Y10S430/126—Halogen compound 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
    • Y10S430/146—Laser beam

Definitions

  • Organic onium salts especially those containing iodonium and sulfonium, cations, are particularly useful as PAGs in chemically amplified photoresist applications owing to their high quantum efficiency for acid production at commonly used exposure wavelengths.
  • positive photoresists used in semiconductor microlithography a number of other features and functional properties have been identified as being critical to PAG performance.
  • Ionic PAGs have additional utility in the preparation of polymer coatings, sealants, encapsulants, and the like derived from cationically polymerizable monomers and oligomers.
  • alkylene refers to a divalent, straight or branched chain, cyclic or acyclic, saturated hydrocarbon radical such as, for example, -CH 2 -, -CH 2 CH 2 -, - CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH(CH 3 )CH 2 -, -CH 2 CH(CH 2 CH 3 )CH 2 CH(CH 3 )CH 2 -, and the like.
  • Alkylene groups include, for example, 1 to 20, 1 to 12, or 1 to 4 carbon atoms. Cyclic alkylene groups, or cycloalkylenes have at least 5, preferably 5 to 7, carbon atoms in the ring.
  • Difunctional or cyclic fluorochemical intermediates that are useful precursors for preparing the perfluorinated, multifunctional PAGs of the present invention using methods that are generally well known in the art include, but are not limited to:
  • Suitable PAGs having photoactivatable groups and a perfluorinated multifunctional anion (or incipient anion) for use in the polymerizable or resist compositions of the instant invention are those that upon application of sufficient energy; accelerated particle (electron beam, ion beam), or electromagnetic radiation sources employing x-ray, extreme-UV, deep-UV, mid-UV near-UV and visible radiation will generate an acid species capable of initiating or catalyzing the desired polymerization, depolymerization, or deblocking chemistry.
  • Negative working photoresists generally contain a cross-linking agent or a polymerizable group linked to a soluble polymer or oligomer.
  • the acid produced from exposure of the photoacid generator causes the exposed area to become crosslinked and therefore insoluble in developer.
  • Chemically amplified resist systems based upon acid catalyzed chain reactions are recognized as a preferred class of resist system for micro- or nanolithography due to the high spectral sensitivity provided by the acid-catalyzed or initiated chemical amplification mechanism and the insensitivity of such systems to oxygen, a common inhibitor of free radical processes. It is also recognized that positive-working photoresists are generally capable of providing better image resolution than negative working photoresists and are therefore preferred in applications where very fine-line image resolution is required, as in the manufacture of semiconductor devices.
  • cycloaliphatic epoxies such as cyclohexene oxide and the ERLTM series of resins available from Union Carbide, such as vinylcyclohexene dioxide (ERL-4206TM), 3,4-epoxycyclohexylmethyl-3,4- epoxycyclohexanecarboxylate (ERL-4221TM), bis(3,4-epoxy-6- methylcyclohexylmethyl)adipate (ERL-4299TM); 1,4-butanediol diglycidyl ether, (for example, Heloxy 67TM available from Shell Chemical), polyglycidyl ether of phenol- formaldehyde novolak (e.g., DER-431TM and DER-438TM, available from Dow Chemical Co., polyglycol diepoxide (e.g., DER 736TM, available from Dow Chemical Co.), and mixtures thereof as well as mixtures thereof with co-curatives, curing agents or harden
  • Epoxy resins preferred for use in conductive adhesives are the glycidyl ether type of resins, particularly in formulations where stabilizers are present.
  • hydroxy-functional materials can be added.
  • the hydroxyl-functional component can be present as a mixture or a blend of materials and can contain mono- and poly-hydroxyl containing materials.
  • the hydroxyl-functional material is at least a diol.
  • the hydroxyl- functional material can aid in chain extension and preventing excess crosslinking of the epoxy during curing, e.g. , increasing toughness of the cured composition.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
PCT/US2004/014348 2003-05-22 2004-05-07 Photoacid generators with perfluorinated multifunctional anions Ceased WO2004107051A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP04751648.9A EP1625447B1 (en) 2003-05-22 2004-05-07 Photoacid generators with perfluorinated multifunctional anions
JP2006532863A JP4680915B2 (ja) 2003-05-22 2004-05-07 過フッ素化多官能性アニオンを有する光酸発生剤
CN200480014082XA CN1802607B (zh) 2003-05-22 2004-05-07 具有全氟化多官能阴离子的光酸产生剂
KR1020057022224A KR101070032B1 (ko) 2003-05-22 2005-11-21 퍼플루오르화 다관능성 음이온을 갖는 광산 발생제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/444,124 US7122294B2 (en) 2003-05-22 2003-05-22 Photoacid generators with perfluorinated multifunctional anions
US10/444,124 2003-05-22

Publications (2)

Publication Number Publication Date
WO2004107051A2 true WO2004107051A2 (en) 2004-12-09
WO2004107051A3 WO2004107051A3 (en) 2006-03-09

Family

ID=33450568

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/014348 Ceased WO2004107051A2 (en) 2003-05-22 2004-05-07 Photoacid generators with perfluorinated multifunctional anions

Country Status (6)

Country Link
US (1) US7122294B2 (https=)
EP (1) EP1625447B1 (https=)
JP (1) JP4680915B2 (https=)
KR (1) KR101070032B1 (https=)
CN (1) CN1802607B (https=)
WO (1) WO2004107051A2 (https=)

Cited By (11)

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EP1517179A1 (en) 2003-09-10 2005-03-23 Fuji Photo Film Co., Ltd. Photosensitive composition and pattern forming method using the same
JP2005122134A (ja) * 2003-09-10 2005-05-12 Fuji Photo Film Co Ltd 感光性組成物及びそれを用いたパターン形成方法
EP1662317A3 (en) * 2004-09-30 2006-06-28 Fuji Photo Film Co., Ltd. Resist composition and method of pattern formation with the same
JP2007052346A (ja) * 2005-08-19 2007-03-01 Fujifilm Corp 液浸露光用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
JP2007326821A (ja) * 2006-06-09 2007-12-20 National Institute Of Advanced Industrial & Technology 新規なオニウム塩
EP1935640A2 (en) 2006-12-19 2008-06-25 Palo Alto Research Center Incorporated Printing plate and system using heat-decomposable polymers
US7923199B2 (en) 2005-01-28 2011-04-12 Fujifilm Corporation Photosensitive composition, compound for use in the photosensitive composition and pattern forming method using the photosensitive composition
WO2015049871A1 (en) * 2013-10-02 2015-04-09 Toyo Gosei Co., Ltd. Reagent for enhancing generation of chemical species
WO2015052914A1 (en) * 2013-10-07 2015-04-16 Toyo Gosei Co., Ltd. Reagent for enhancing generation of chemical species and manufacturing apparatus
US9551928B2 (en) 2009-04-06 2017-01-24 Fujifilm Corporation Actinic-ray- or radiation-sensitive resin composition and method of forming pattern therewith
US10031416B2 (en) 2013-08-07 2018-07-24 Toyo Gosei Co., Ltd. Reagent for enhancing generation of chemical species

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JP4389485B2 (ja) * 2003-06-04 2009-12-24 Ｊｓｒ株式会社 酸発生剤および感放射線性樹脂組成物
JP4474246B2 (ja) * 2003-09-19 2010-06-02 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
US7449573B2 (en) * 2004-02-16 2008-11-11 Fujifilm Corporation Photosensitive composition, compound for use in the photosensitive composition, and method of pattern formation with the photosensitive composition
JP2007003619A (ja) * 2005-06-21 2007-01-11 Fujifilm Holdings Corp 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に用いる化合物
US7521170B2 (en) * 2005-07-12 2009-04-21 Az Electronic Materials Usa Corp. Photoactive compounds
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GB2441032B (en) * 2006-08-18 2008-11-12 Sumitomo Chemical Co Salts of perfluorinated sulfoacetic acids
JP5226994B2 (ja) * 2006-09-11 2013-07-03 住友化学株式会社 化学増幅型レジスト組成物の酸発生剤の中間体
KR100829615B1 (ko) 2006-10-11 2008-05-14 삼성전자주식회사 광산 발생제, 이를 포함하는 포토레지스트 조성물 및 패턴형성 방법
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US8034533B2 (en) * 2008-01-16 2011-10-11 International Business Machines Corporation Fluorine-free heteroaromatic photoacid generators and photoresist compositions containing the same
JP5572292B2 (ja) * 2008-06-20 2014-08-13 三菱マテリアル株式会社 ペルフルオロ二官能酸の製造方法
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JP5618757B2 (ja) * 2010-06-29 2014-11-05 富士フイルム株式会社 半導体用レジスト組成物、並びに、この組成物を用いたレジスト膜及びパターン形成方法
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US9156785B2 (en) 2010-11-15 2015-10-13 Rohm And Haas Electronic Materials Llc Base reactive photoacid generators and photoresists comprising same
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US8614047B2 (en) 2011-08-26 2013-12-24 International Business Machines Corporation Photodecomposable bases and photoresist compositions
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US10831100B2 (en) * 2017-11-20 2020-11-10 Rohm And Haas Electronic Materials, Llc Iodine-containing photoacid generators and compositions comprising the same
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WO2020158337A1 (ja) * 2019-01-28 2020-08-06 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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US20240368000A1 (en) * 2021-06-25 2024-11-07 University Of Washington Carbon removal from seawater and other liquids using photoactive compounds
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JP7791860B2 (ja) * 2022-07-19 2025-12-24 デュポン エレクトロニック マテリアルズ インターナショナル，エルエルシー 光酸発生剤、フォトレジスト組成物及びパターン形成方法
CN119556527B (zh) * 2025-01-10 2025-10-21 广东科优材料科技有限公司 一种光刻胶组合物及其制备工艺

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JP2007507580A (ja) 2007-03-29
JP4680915B2 (ja) 2011-05-11
EP1625447B1 (en) 2014-04-23
KR20060013672A (ko) 2006-02-13
KR101070032B1 (ko) 2011-10-04
CN1802607B (zh) 2011-10-05
US20040234888A1 (en) 2004-11-25
EP1625447A2 (en) 2006-02-15
US7122294B2 (en) 2006-10-17
CN1802607A (zh) 2006-07-12

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