WO2009021400A1 - Composition de nettoyage pour retirer une réserve - Google Patents

Composition de nettoyage pour retirer une réserve Download PDF

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Publication number
WO2009021400A1
WO2009021400A1 PCT/CN2008/001437 CN2008001437W WO2009021400A1 WO 2009021400 A1 WO2009021400 A1 WO 2009021400A1 CN 2008001437 W CN2008001437 W CN 2008001437W WO 2009021400 A1 WO2009021400 A1 WO 2009021400A1
Authority
WO
WIPO (PCT)
Prior art keywords
cleaning agent
photoresist cleaning
agent according
mass
photoresist
Prior art date
Application number
PCT/CN2008/001437
Other languages
English (en)
Chinese (zh)
Inventor
Bing Liu
Libbert Hongxiu Peng
Robert Yongtao Shi
Original Assignee
Anji Microelectronics (Shanghai) 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 Anji Microelectronics (Shanghai) Co., Ltd filed Critical Anji Microelectronics (Shanghai) Co., Ltd
Priority to CN200880103488.3A priority Critical patent/CN101971103B/zh
Publication of WO2009021400A1 publication Critical patent/WO2009021400A1/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F1/00Etching metallic material by chemical means
    • C23F1/10Etching compositions
    • C23F1/14Aqueous compositions
    • C23F1/32Alkaline compositions
    • C23F1/34Alkaline compositions for etching copper or alloys thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02Inorganic compounds
    • C11D7/04Water-soluble compounds
    • C11D7/06Hydroxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22Organic compounds
    • C11D7/32Organic compounds containing nitrogen
    • C11D7/3218Alkanolamines or alkanolimines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22Organic compounds
    • C11D7/34Organic compounds containing sulfur
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/42Stripping or agents therefor
    • G03F7/422Stripping or agents therefor using liquids only
    • G03F7/425Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/42Stripping or agents therefor
    • G03F7/422Stripping or agents therefor using liquids only
    • G03F7/426Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10Objects to be cleaned
    • C11D2111/14Hard surfaces
    • C11D2111/22Electronic devices, e.g. PCBs or semiconductors

Definitions

  • the present invention relates to a cleaning agent in a semiconductor manufacturing process, and in particular to a photoresist cleaning agent.
  • a mask of a photoresist is formed on a surface of a metal such as silicon dioxide, Cu (copper) or the like, and a low-k material, and the pattern is transferred by wet or dry etching after exposure.
  • a photoresist material photoresist
  • a more common method for improving the removal is to extend the soaking time, increase the soaking temperature, and use a more aggressive solution, but this often results in corrosion of the wafer substrate and corrosion of the microspheres, resulting in a significant reduction in wafer yield.
  • Patent document WO2006/056298A1 utilizes an alkaline cleaning agent consisting of tetramethylammonium hydroxide (TMAH), dimethyl sulfoxide (DMSO), ethylene glycol (EG) and water for cleaning light of 50 to 100 microns thick. Engraved. The cleaning agent is substantially non-corrosive to metallic copper.
  • TMAH tetramethylammonium hydroxide
  • DMSO dimethyl sulfoxide
  • EG ethylene glycol
  • Patent document US 2204/0074519 A1 utilizes an alkaline cleaning agent consisting of benzyltrimethylammonium hydroxide (BTMAH), N-methylpyrrolidone (NMP), ethylene glycol (EG), corrosion inhibitors, surfactants and stabilizers. , used to clean thicker negative photoresist.
  • BTMAH benzyltrimethylammonium hydroxide
  • NMP N-methylpyrrolidone
  • EG ethylene glycol
  • corrosion inhibitors e.g., sodium sulfate
  • surfactants and stabilizers ethylene glycol
  • Patent document US6040117 utilizes an alkaline cleaning agent consisting of TMAH, dimethyl sulfoxide (DMSO), 1,3,-dimethyl-2-imidazolidinone (DM) and water to immerse the wafer in the cleaning agent. A 20 ⁇ thick film photoresist on metal and dielectric substrates was removed at 50 to 100 °C.
  • Confirmation Patent document US5962197 utilizes propylene glycol ether, pyrrolidone, KOH, a surfactant and traces of water to form an alkaline cleaner for cleaning the photoresist.
  • Patent Document US 5529887 utilizes diethylene glycol monodecyl ether, ethylene glycol monoalkyl ether, alkali metal hydroxide, water soluble fluoride and water to form an alkaline cleaning agent for cleaning photoresist.
  • the above cleaning liquids have a low cleaning ability, and some have a high corrosion rate to the substrate copper; therefore, it is particularly important to develop a cleaning liquid having a higher cleaning ability and a lower corrosion rate of copper.
  • the technical problem to be solved by the present invention is to overcome the problems of the prior art photoresist cleaning agent or the cleaning ability, or the problem of strong corrosiveness to the wafer substrate, and to provide a strong cleaning ability, especially to effectively remove the thick film.
  • Photoresist a photoresist cleaner that is less corrosive to wafer substrates.
  • the photoresist cleaning agent of the present invention contains: potassium hydroxide, dimethyl sulfoxide, pentaerythritol, and an alcohol amine.
  • the content of the potassium hydroxide is preferably 0.1 to 10% by mass, more preferably 0.1 to 3% by mass; and the content of the dimethyl sulfoxide is preferably 20% by mass. 98.8%, the mass percentage is 50-98.4%; the content of the pentaerythritol is preferably 1% to 40% by mass, more preferably 1% to 30% by mass; the content of the alcoholamine is preferably the mass.
  • the percentage is 0.1 to 50%, and more preferably 0.5 to 30% by mass.
  • the alcoholamine is preferably monoethanolamine, diethanolamine, triethanolamine, n-propanolamine, isopropanolamine, 2-(diethylamino)ethanol, ethyldiethanolamine and diglycolamine One or more.
  • the photoresist cleaning agent of the present invention may further contain a corrosion inhibitor.
  • the content of the corrosion inhibitor is preferably less than or equal to 10% by mass, more preferably less than or equal to the mass percentage. 3%.
  • the corrosion inhibitor is selected from the group consisting of phenols, carboxylic acids, carboxylic acid esters, 2-mercaptobenzothiazoles, benzotriazoles, acid anhydrides, phosphonic acids and phosphonates.
  • One or more of the etchants is preferably one or more of phenol, 1,2-dihydroxyphenol, p-hydroxyphenol and pyrogallol; the carboxylic acid is preferably benzoic acid and/or p-aminobenzene.
  • the carboxylic acid esters are preferably one or more of methyl p-aminobenzoate, phthalic acid, methyl phthalate, gallic acid and propyl gallate; benzotriazoles Preferred are potassium benzotriazole salts; the acid anhydrides are preferably one or more of acetic anhydride, hexanoic anhydride, maleic anhydride and maleic anhydride; the preferred phosphoric acid is 1,3- (Hydroxyethyl)-2,4,6-triphosphonic acid. Among them, the most preferred is benzotriazole potassium salt.
  • the photoresist cleaning liquid of the present invention can be obtained by simply mixing and mixing the above components.
  • the photoresist cleaning solution of the present invention can be used by immersing a semiconductor wafer containing a photoresist in the photoresist cleaning agent of the present invention, immersing it at room temperature to 95 ° C for a suitable period of time, and then taking it out. After washing with deionized water, it can be dried by high-purity nitrogen.
  • the reagents and starting materials used in the present invention are commercially available.
  • the positive progress of the present invention is that the pentaerythritol and the alkanolamine contained in the photoresist cleaning agent of the present invention can dissolve potassium hydroxide as a solvent, and can also form on the surface of the metal (UBM) under the metal microspheres and the metal microspheres. A protective film to reduce corrosion on the substrate. Moreover, pentaerythritol also has a certain protective effect on metallic copper.
  • the photoresist cleaning agent of the invention can effectively remove photoresist (resistance) and other residues on metal, metal alloy or dielectric substrate, and can also be used for cleaning of thick (thickness greater than 100 micron) photoresist. At the same time, it has a lower etching rate for metals such as Cu (copper), and has a good application prospect in the field of microelectronics such as semiconductor wafer cleaning. Summary of the invention
  • Table 1 shows the formulations of Examples 1 to 22, and the components were simply mixed uniformly according to the formulation of Table 1, and the photoresist cleaning solutions of the respective examples were obtained.
  • Table 2 shows the formulations of the comparative photoresist cleaning solutions 1 to 3 and the photoresist cleaning solutions 1 to 4 of the present invention, and the components were simply mixed uniformly according to the formulation of Table 2 to prepare each photoresist cleaning solution.
  • the comparative photoresist cleaning solution 1 did not form a homogeneous solution, indicating that the solubility of KOH in dimethyl sulfoxide was small. Comparing the photoresist cleaning solutions 2 and 3 to form a uniform solution, indicating the addition of pentaerythritol
  • the semiconductor wafer containing 120 micron photoresist is immersed in the comparative photoresist cleaning liquid 2 to 3 and the photoresist cleaning liquid 1 to 4 of the present invention, soaked under the conditions in Table 3, and taken out after washing with deionized water. Then dry it with high purity nitrogen.
  • Table 3 Comparison of the photoresist cleaning solution 1 ⁇ 3 and the photoresist cleaning solution of the present invention 1 ⁇ 4 wafer cleaning
  • the comparative photoresist cleaning solution 2 containing a base and pentaerythritol but no alcohol amine is highly corrosive to the metal microspheres
  • the comparative photoresist cleaning liquid containing the alkali and the alcohol amine but no pentaerythritol 3 The corrosion of copper is heavier, and the photoresist cleaning solution of the present invention contains a base, an alcoholamine and pentaerythritol, and has a significant corrosion inhibiting effect on copper and metal microspheres.
  • the alcohol amine has a corrosion inhibiting effect on the metal microspheres; however, the addition of the alcohol amine causes the corrosion of Cu to be aggravated; The amount of the alcoholamine and pentaerythritol is appropriately balanced.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

L'invention porte sur une composition de nettoyage pour retirer une réserve, qui comprend de l'hydroxyde de potassium, du diméthylsulfoxyde, du pentaérythritol et de l'amine-alcool. La composition de nettoyage peut nettoyer une réserve et autres résidus d'un substrat métallique, d'alliage métallique et diélectrique, et a une vitesse de gravure faible pour un métal, tel que Cu et similaires.
PCT/CN2008/001437 2007-08-10 2008-08-08 Composition de nettoyage pour retirer une réserve WO2009021400A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200880103488.3A CN101971103B (zh) 2007-08-10 2008-08-08 一种光刻胶清洗剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNA2007100447903A CN101364056A (zh) 2007-08-10 2007-08-10 一种光刻胶清洗剂
CN200710044790.3 2007-08-10

Publications (1)

Publication Number Publication Date
WO2009021400A1 true WO2009021400A1 (fr) 2009-02-19

Family

ID=40350360

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2008/001437 WO2009021400A1 (fr) 2007-08-10 2008-08-08 Composition de nettoyage pour retirer une réserve

Country Status (2)

Country Link
CN (2) CN101364056A (fr)
WO (1) WO2009021400A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102096345A (zh) * 2009-12-11 2011-06-15 安集微电子(上海)有限公司 一种厚膜光刻胶清洗液及其清洗方法
CN102566332B (zh) * 2010-12-30 2016-04-20 安集微电子(上海)有限公司 一种厚膜光刻胶清洗液
CN102566330B (zh) * 2010-12-10 2016-04-20 安集微电子(上海)有限公司 一种厚膜光刻胶清洗液
WO2012075686A1 (fr) * 2010-12-10 2012-06-14 安集微电子(上海)有限公司 Solution de décapant de résine photosensible en film épais
CN102566331B (zh) * 2010-12-21 2016-08-03 安集微电子(上海)有限公司 一种厚膜光刻胶清洗液
WO2012083587A1 (fr) * 2010-12-21 2012-06-28 安集微电子(上海)有限公司 Liquide de nettoyage pour photoréserves en couche épaisse
CN102540774A (zh) * 2010-12-21 2012-07-04 安集微电子(上海)有限公司 一种厚膜光刻胶清洗剂
CN102981376A (zh) * 2011-09-05 2013-03-20 安集微电子(上海)有限公司 一种光刻胶清洗液
CN103389627A (zh) * 2012-05-11 2013-11-13 安集微电子科技(上海)有限公司 一种光刻胶清洗液
CN103809393A (zh) * 2012-11-12 2014-05-21 安集微电子科技(上海)有限公司 一种去除光阻残留物的清洗液
CN103513520A (zh) * 2013-09-24 2014-01-15 刘超 防腐剂混合物和光刻胶剥离剂组合物
CN103529656A (zh) * 2013-10-23 2014-01-22 杨桂望 包含咪唑啉缓蚀剂的感光膜清洗液
CN103616806B (zh) * 2013-10-25 2017-02-08 马佳 感光膜清洗液
CN103605269B (zh) * 2013-10-25 2016-11-23 马佳 用于半导体制造的感光膜清洗液
CN103616805A (zh) * 2013-10-25 2014-03-05 青岛华仁技术孵化器有限公司 半导体制造过程中使用的清洗液
CN104678719A (zh) * 2013-11-28 2015-06-03 安集微电子科技(上海)有限公司 一种对金属极低腐蚀的光刻胶清洗液
CN104531397A (zh) * 2014-11-18 2015-04-22 惠晶显示科技(苏州)有限公司 一种平板玻璃基板减薄预清洗用清洗液及其应用
CN106919011B (zh) * 2015-12-25 2021-12-17 安集微电子科技(上海)股份有限公司 一种富含水的羟胺剥离清洗液
CN106367215A (zh) * 2016-08-19 2017-02-01 广东泰强化工实业有限公司 一种气雾多功能清洗剂及其制备方法

Citations (5)

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US20030181344A1 (en) * 2002-03-12 2003-09-25 Kazuto Ikemoto Photoresist stripping composition and cleaning composition
US20050119143A1 (en) * 1999-01-27 2005-06-02 Egbe Matthew I. Compositions for the removal of organic and inorganic residues
CN1715389A (zh) * 2004-07-01 2006-01-04 气体产品与化学公司 用于清除和清洗的组合物及其用途
CN1743965A (zh) * 2005-09-30 2006-03-08 石深泉 环保型再生ps版油墨及感光胶剥离剂及其配制方法
CN101187788A (zh) * 2006-11-17 2008-05-28 安集微电子(上海)有限公司 低蚀刻性较厚光刻胶清洗液

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US4169068A (en) * 1976-08-20 1979-09-25 Japan Synthetic Rubber Company Limited Stripping liquor composition for removing photoresists comprising hydrogen peroxide
JP2911792B2 (ja) * 1995-09-29 1999-06-23 東京応化工業株式会社 レジスト用剥離液組成物
US7282324B2 (en) * 2004-01-05 2007-10-16 Microchem Corp. Photoresist compositions, hardened forms thereof, hardened patterns thereof and metal patterns formed using them

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US20050119143A1 (en) * 1999-01-27 2005-06-02 Egbe Matthew I. Compositions for the removal of organic and inorganic residues
US20030181344A1 (en) * 2002-03-12 2003-09-25 Kazuto Ikemoto Photoresist stripping composition and cleaning composition
CN1715389A (zh) * 2004-07-01 2006-01-04 气体产品与化学公司 用于清除和清洗的组合物及其用途
CN1743965A (zh) * 2005-09-30 2006-03-08 石深泉 环保型再生ps版油墨及感光胶剥离剂及其配制方法
CN101187788A (zh) * 2006-11-17 2008-05-28 安集微电子(上海)有限公司 低蚀刻性较厚光刻胶清洗液

Also Published As

Publication number Publication date
CN101364056A (zh) 2009-02-11
CN101971103A (zh) 2011-02-09
CN101971103B (zh) 2013-02-13

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