US20020106589A1 - Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers - Google Patents

Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers Download PDF

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Publication number
US20020106589A1
US20020106589A1 US10/024,893 US2489301A US2002106589A1 US 20020106589 A1 US20020106589 A1 US 20020106589A1 US 2489301 A US2489301 A US 2489301A US 2002106589 A1 US2002106589 A1 US 2002106589A1
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United States
Prior art keywords
propylene oxide
diol
ethylene oxide
composition
acetylenic
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Granted
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US10/024,893
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English (en)
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US6455234B1 (en
Inventor
Kevin Rodney
Paula Ann
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Evonik Operations GmbH
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Air Products and Chemicals Inc
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Filing date
Publication date
Priority claimed from US09/304,607 external-priority patent/US6313182B1/en
Application filed by Air Products and Chemicals Inc filed Critical Air Products and Chemicals Inc
Priority to US10/024,893 priority Critical patent/US6455234B1/en
Assigned to AIR PRODUCTS AND CHEMICALS, INC. reassignment AIR PRODUCTS AND CHEMICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LASSILA, KEVIN RODNEY, UHRIN, PAULA ANN
Assigned to AIR PRODUCTS AND CHEMICALS, INC. reassignment AIR PRODUCTS AND CHEMICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SCHWARTZ, JOEL
Publication of US20020106589A1 publication Critical patent/US20020106589A1/en
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Publication of US6455234B1 publication Critical patent/US6455234B1/en
Assigned to FUJIFILM ELECTRONIC MATERIALS USA INC. reassignment FUJIFILM ELECTRONIC MATERIALS USA INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AIR PRODUCTS AND CHEMICALS, INC.
Assigned to AIR PRODUCTS AND CHEMICALS, INC. reassignment AIR PRODUCTS AND CHEMICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FUFIFILM ELECTRONIC MATERIALS USA, INC.
Assigned to AIR PRODUCTS AND CHEMICALS, INC. reassignment AIR PRODUCTS AND CHEMICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FUJIFILM ELECTRONIC MATERIALS USA, INC.
Assigned to EVONIK DEGUSSA GMBH reassignment EVONIK DEGUSSA GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AIR PRODUCTS AND CHEMICALS, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/60—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing acetylenic group
US10/024,893 1999-05-04 2001-12-18 Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers Expired - Lifetime US6455234B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/024,893 US6455234B1 (en) 1999-05-04 2001-12-18 Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US30461299A 1999-05-04 1999-05-04
US09/304,607 US6313182B1 (en) 1999-05-04 1999-05-04 Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
US47760000A 2000-01-04 2000-01-04
US10/024,893 US6455234B1 (en) 1999-05-04 2001-12-18 Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers

Related Parent Applications (3)

Application Number Title Priority Date Filing Date
US30461299A Continuation-In-Part 1999-05-04 1999-05-04
US09/304,607 Continuation-In-Part US6313182B1 (en) 1999-05-04 1999-05-04 Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
US47760000A Continuation-In-Part 1999-05-04 2000-01-04

Publications (2)

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US20020106589A1 true US20020106589A1 (en) 2002-08-08
US6455234B1 US6455234B1 (en) 2002-09-24

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US10/024,893 Expired - Lifetime US6455234B1 (en) 1999-05-04 2001-12-18 Acetylenic diol ethylene oxide/propylene oxide adducts and their use in photoresist developers

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Cited By (28)

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US6641986B1 (en) * 2002-08-12 2003-11-04 Air Products And Chemicals, Inc. Acetylenic diol surfactant solutions and methods of using same
US20040029395A1 (en) * 2002-08-12 2004-02-12 Peng Zhang Process solutions containing acetylenic diol surfactants
US20040127380A1 (en) * 2002-12-31 2004-07-01 3M Innovative Properties Company Degreasing compositions
US20040137364A1 (en) * 2002-11-15 2004-07-15 Kim Young H. Protective layers compatible with thick film pastes
US20040204328A1 (en) * 2002-08-12 2004-10-14 Peng Zhang Process solutions containing surfactants
US20040252970A1 (en) * 2003-06-11 2004-12-16 Samsung Electronics Co., Ltd. Apparatus and method for controlling reverse-play for digital video bitstream
US20050081885A1 (en) * 2003-10-20 2005-04-21 Peng Zhang Process solutions containing surfactants used as post-chemical mechanical planarization treatment
US20050143270A1 (en) * 2003-10-28 2005-06-30 Sachem, Inc. Cleaning solutions and etchants and methods for using same
US20050176605A1 (en) * 1999-05-04 2005-08-11 Lassila Kevin R. Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
WO2005119372A1 (en) * 2004-05-27 2005-12-15 E.I. Dupont De Nemours And Company Developer for a photopolymer protective layer
US20080098933A1 (en) * 2006-10-25 2008-05-01 Wacker Polymer Systems Gmbh & Co. Kg Dispersion powder compositions comprising gemini surfactants
US20080166666A1 (en) * 2002-12-06 2008-07-10 David Herbert Roach Positive imageable thick film composition
US7402373B2 (en) 2004-02-05 2008-07-22 E.I. Du Pont De Nemours And Company UV radiation blocking protective layers compatible with thick film pastes
US20100159400A1 (en) * 2008-12-24 2010-06-24 Samsung Electronics Co., Ltd. Composition for removing a photoresist pattern and method of forming a metal pattern using the composition
CN102304029A (zh) * 2011-04-11 2012-01-04 杨朝辉 一种炔二醇和环氧乙烷加合物的合成方法
CN102787035A (zh) * 2011-05-18 2012-11-21 奇美实业股份有限公司 洗净液组成物及基板的洗净方法
CN102839064A (zh) * 2011-06-20 2012-12-26 奇美实业股份有限公司 洗净液组成物
CN103242143A (zh) * 2013-04-18 2013-08-14 岳阳市英泰合成材料有限公司 一种炔醇烷氧基化的生产工艺
CN103240124A (zh) * 2013-04-18 2013-08-14 岳阳市英泰合成材料有限公司 一种用于炔醇烷氧基化的催化剂
US20140011359A1 (en) * 2011-03-21 2014-01-09 Basf Se Aqueous, nitrogen-free cleaning composition and its use for removing residues and contaminants from semiconductor substrates suitable for manufacturing microelectronic devices
CN103965461A (zh) * 2014-05-19 2014-08-06 上海多纶化工有限公司 炔二醇聚氧乙烯醚的合成方法
CN103965462A (zh) * 2014-05-19 2014-08-06 上海多纶化工有限公司 用于炔二醇聚氧乙烯醚合成的催化剂
US8900802B2 (en) 2013-02-23 2014-12-02 International Business Machines Corporation Positive tone organic solvent developed chemically amplified resist
JP2015018224A (ja) * 2013-06-12 2015-01-29 信越化学工業株式会社 感光性レジスト材料用現像液及びこれを用いたパターン形成方法
JP2015026064A (ja) * 2013-06-19 2015-02-05 信越化学工業株式会社 感光性レジスト材料用現像液及びこれを用いたパターン形成方法
US20160195813A1 (en) * 2015-01-05 2016-07-07 Shin-Etsu Chemical Co., Ltd. Developer and patterning process using the same
US9494867B2 (en) 2013-05-09 2016-11-15 Az Electronic Materials (Luxembourg) S.A.R.L. Rinsing liquid for lithography and pattern forming method using same
WO2021114619A1 (zh) * 2019-12-10 2021-06-17 浙江皇马新材料科技有限公司 一种炔二醇嵌段聚醚及其合成方法

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US7129199B2 (en) * 2002-08-12 2006-10-31 Air Products And Chemicals, Inc. Process solutions containing surfactants
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KR100574349B1 (ko) * 2004-02-03 2006-04-27 삼성전자주식회사 세정액 조성물 및 이를 이용한 반도체 장치의 세정방법
US20070299176A1 (en) * 2005-01-28 2007-12-27 Markley Thomas J Photodefinable low dielectric constant material and method for making and using same
KR100993516B1 (ko) * 2005-06-13 2010-11-10 가부시끼가이샤 도꾸야마 포토레지스트 현상액, 및 그 현상액을 사용한 기판의 제조방법
US20070196773A1 (en) * 2006-02-22 2007-08-23 Weigel Scott J Top coat for lithography processes
US20080264672A1 (en) * 2007-04-26 2008-10-30 Air Products And Chemicals, Inc. Photoimprintable Low Dielectric Constant Material and Method for Making and Using Same
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Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7348300B2 (en) 1999-05-04 2008-03-25 Air Products And Chemicals, Inc. Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
US20050176605A1 (en) * 1999-05-04 2005-08-11 Lassila Kevin R. Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture
US6641986B1 (en) * 2002-08-12 2003-11-04 Air Products And Chemicals, Inc. Acetylenic diol surfactant solutions and methods of using same
US20040029395A1 (en) * 2002-08-12 2004-02-12 Peng Zhang Process solutions containing acetylenic diol surfactants
US20080063984A1 (en) * 2002-08-12 2008-03-13 Air Products And Chemicals, Inc. Process Solutions Containing Surfactants
US20040204328A1 (en) * 2002-08-12 2004-10-14 Peng Zhang Process solutions containing surfactants
US7521405B2 (en) * 2002-08-12 2009-04-21 Air Products And Chemicals, Inc. Process solutions containing surfactants
US20040137364A1 (en) * 2002-11-15 2004-07-15 Kim Young H. Protective layers compatible with thick film pastes
US7374859B2 (en) 2002-11-15 2008-05-20 E.I. Du Pont De Nemours And Company Protective layers compatible with thick film pastes
US20080166666A1 (en) * 2002-12-06 2008-07-10 David Herbert Roach Positive imageable thick film composition
US7235517B2 (en) * 2002-12-31 2007-06-26 3M Innovative Properties Company Degreasing compositions
US20070219109A1 (en) * 2002-12-31 2007-09-20 3M Innovative Properties Company Degreasing compositions
US20040127380A1 (en) * 2002-12-31 2004-07-01 3M Innovative Properties Company Degreasing compositions
US20040252970A1 (en) * 2003-06-11 2004-12-16 Samsung Electronics Co., Ltd. Apparatus and method for controlling reverse-play for digital video bitstream
US7437054B2 (en) 2003-06-11 2008-10-14 Samsung Electronics Co., Ltd. Apparatus and method for controlling reverse-play for digital video bitstream
US7452426B2 (en) 2003-10-20 2008-11-18 Air Products And Chemicals, Inc. Process solutions containing surfactants used as post-chemical mechanical planarization treatment
US20050081885A1 (en) * 2003-10-20 2005-04-21 Peng Zhang Process solutions containing surfactants used as post-chemical mechanical planarization treatment
US7208049B2 (en) * 2003-10-20 2007-04-24 Air Products And Chemicals, Inc. Process solutions containing surfactants used as post-chemical mechanical planarization treatment
US20070006894A1 (en) * 2003-10-20 2007-01-11 Peng Zhang Process solutions containing surfactants used as post-chemical mechanical planarization treatment
US20050143270A1 (en) * 2003-10-28 2005-06-30 Sachem, Inc. Cleaning solutions and etchants and methods for using same
US7402373B2 (en) 2004-02-05 2008-07-22 E.I. Du Pont De Nemours And Company UV radiation blocking protective layers compatible with thick film pastes
US7608383B2 (en) 2004-02-05 2009-10-27 E.I. Du Pont De Nemours And Company UV radiation blocking protective layers compatible with thick film pastes
US20080274430A1 (en) * 2004-02-05 2008-11-06 Kim Young H Uv radiation blocking protective layers compatible with thick film pastes
WO2005119372A1 (en) * 2004-05-27 2005-12-15 E.I. Dupont De Nemours And Company Developer for a photopolymer protective layer
US20100261116A1 (en) * 2004-05-27 2010-10-14 Kim Young H Developer for a photopolymer protective layer
US20080098933A1 (en) * 2006-10-25 2008-05-01 Wacker Polymer Systems Gmbh & Co. Kg Dispersion powder compositions comprising gemini surfactants
US9334388B2 (en) 2006-10-25 2016-05-10 Wacker Chemie Ag Dispersion powder compositions comprising gemini surfactants
US20100159400A1 (en) * 2008-12-24 2010-06-24 Samsung Electronics Co., Ltd. Composition for removing a photoresist pattern and method of forming a metal pattern using the composition
US20140011359A1 (en) * 2011-03-21 2014-01-09 Basf Se Aqueous, nitrogen-free cleaning composition and its use for removing residues and contaminants from semiconductor substrates suitable for manufacturing microelectronic devices
US9275851B2 (en) * 2011-03-21 2016-03-01 Basf Se Aqueous, nitrogen-free cleaning composition and its use for removing residues and contaminants from semiconductor substrates suitable for manufacturing microelectronic devices
CN102304029A (zh) * 2011-04-11 2012-01-04 杨朝辉 一种炔二醇和环氧乙烷加合物的合成方法
CN102787035A (zh) * 2011-05-18 2012-11-21 奇美实业股份有限公司 洗净液组成物及基板的洗净方法
CN102839064A (zh) * 2011-06-20 2012-12-26 奇美实业股份有限公司 洗净液组成物
US8900802B2 (en) 2013-02-23 2014-12-02 International Business Machines Corporation Positive tone organic solvent developed chemically amplified resist
CN103242143A (zh) * 2013-04-18 2013-08-14 岳阳市英泰合成材料有限公司 一种炔醇烷氧基化的生产工艺
CN103240124A (zh) * 2013-04-18 2013-08-14 岳阳市英泰合成材料有限公司 一种用于炔醇烷氧基化的催化剂
US9494867B2 (en) 2013-05-09 2016-11-15 Az Electronic Materials (Luxembourg) S.A.R.L. Rinsing liquid for lithography and pattern forming method using same
JP2015018224A (ja) * 2013-06-12 2015-01-29 信越化学工業株式会社 感光性レジスト材料用現像液及びこれを用いたパターン形成方法
JP2015026064A (ja) * 2013-06-19 2015-02-05 信越化学工業株式会社 感光性レジスト材料用現像液及びこれを用いたパターン形成方法
CN103965462A (zh) * 2014-05-19 2014-08-06 上海多纶化工有限公司 用于炔二醇聚氧乙烯醚合成的催化剂
CN103965461A (zh) * 2014-05-19 2014-08-06 上海多纶化工有限公司 炔二醇聚氧乙烯醚的合成方法
US20160195813A1 (en) * 2015-01-05 2016-07-07 Shin-Etsu Chemical Co., Ltd. Developer and patterning process using the same
US9645498B2 (en) * 2015-01-05 2017-05-09 Shin-Etsu Chemical Co., Ltd. Developer and patterning process using the same
TWI584084B (zh) * 2015-01-05 2017-05-21 信越化學工業股份有限公司 顯影液及使用該顯影液之圖案形成方法
WO2021114619A1 (zh) * 2019-12-10 2021-06-17 浙江皇马新材料科技有限公司 一种炔二醇嵌段聚醚及其合成方法

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