WO2008052424A1 - Composé de nettoyage pour éliminer le photorésist - Google Patents

Composé de nettoyage pour éliminer le photorésist Download PDF

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Publication number
WO2008052424A1
WO2008052424A1 PCT/CN2007/003019 CN2007003019W WO2008052424A1 WO 2008052424 A1 WO2008052424 A1 WO 2008052424A1 CN 2007003019 W CN2007003019 W CN 2007003019W WO 2008052424 A1 WO2008052424 A1 WO 2008052424A1
Authority
WO
WIPO (PCT)
Prior art keywords
cleaning agent
agent according
ether
photoresist cleaning
compound
Prior art date
Application number
PCT/CN2007/003019
Other languages
English (en)
Chinese (zh)
Inventor
Libbert Hongxiu Peng
Robert Yongtao Shi
Bing Liu
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 CN200780037460XA priority Critical patent/CN101523298B/zh
Publication of WO2008052424A1 publication Critical patent/WO2008052424A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23F—NON-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
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/12—Oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23F—NON-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
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
    • C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
    • C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • 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
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides

Definitions

  • the present invention relates to the field of cleaning processes in semiconductor manufacturing, and more particularly to a photoresist cleaning agent.
  • a pattern of 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 metal such as silicon dioxide, Cu (copper) or the like and a low-k material
  • cleaning agents often cause corrosion of the wafer substrate.
  • metal corrosion is a relatively common and very serious problem, often resulting in a significant reduction in wafer yield.
  • Patent document WO03104901 utilizes trans-1,2-cyclohexanediaminetetraacetic acid (CyDTA) as a corrosion inhibitor, the solution of which consists of tetramethylammonium hydroxide (TMAH:), sulfolane (SFL), water and trans-1. Composition of 2-cyclohexanediaminetetraacetic acid (CyDTA). It has a slightly higher corrosion on the semiconductor wafer substrate.
  • TMAH tetramethylammonium hydroxide
  • SFL sulfolane
  • Patent document WO04059700 utilizes 2-mercaptobenzimidazole (MBI) as a corrosion inhibitor, the solution of which consists of tetramethylammonium hydroxide (TMAH), N-methylmorpholine oxide (MO), water and 2-mercaptobenzophenone. Imidazole (MBI) and other components. It has a high corrosion to the semiconductor wafer substrate. Summary of invention
  • the object of the present invention is to provide a photoresist cleaning agent for reducing metal corrosion during cleaning in a semiconductor manufacturing process.
  • the photoresist cleaning agent of the present invention comprises a corrosion inhibitor and a solvent, characterized in that the corrosion inhibitor comprises two types of compounds: a class of 3 ⁇ 4 mercapto alcohol
  • the aryl ether compound is selected from the group consisting of a phenol compound, a carboxylic acid, a polycarboxylic acid, a carboxylate, a polycarboxylate compound, an acid anhydride, a polyoxonium compound or a phosphonic acid or phosphonate compound.
  • the alkyl alcohol monoaryl ether compound is ethylene glycol monophenyl ether
  • ECMPE propylene glycol monophenyl ether
  • PGMPE propylene glycol monophenyl ether
  • isopropyl glycol monophenyl ether diethylene glycol monophenyl ether, dipropylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol single Benzyl ether, propylene glycol monobenzyl ether or isopropyl glycol monobenzyl ether.
  • preferred are ethylene glycol monophenyl ether, propylene glycol monophenyl ether or isopropyl glycol monophenyl ether.
  • the content of the mercapto alcohol monoaryl ether compound is preferably from 0.05 to 30% by weight, more preferably from 1.0 to 15% by weight.
  • the phenolic compound is 1,2-dihydroxyphenol, p-hydroxyphenol or pyrogallol, preferably pyrogallol.
  • the content of the phenol is preferably 0.001 to 15% by weight, more preferably 0.01 to 5.0% by weight.
  • the carboxylic acid, polycarboxylic acid, carboxylic acid ester, and polycarboxylate compound are benzoic acid, p-aminobenzoic acid (PABA), phthalic acid (PA), gallic acid (GA), A propyl gallate or a carboxyl group-containing acrylate polymer.
  • PABA p-aminobenzoic acid
  • PA phthalic acid
  • GA gallic acid
  • a propyl gallate or a carboxyl group-containing acrylate polymer preferred are preferred are p-aminobenzoic acid, phthalic acid, and gallic acid.
  • the content of the carboxylic acid, polycarboxylic acid, carboxylic acid ester, or polycarboxylate compound is preferably 0.001 to 15% by weight, more preferably 0.01 to 5.0% by weight.
  • the acid anhydride or polyanhydride compound is acetic anhydride, propionic anhydride, hexanoic anhydride, Maleic anhydride or polymaleic anhydride, preferably polymaleic anhydride.
  • the content of the acid anhydride or polyanhydride compound is preferably 0.001 to 15 wt%. More preferably, it is 0.01 to 5.0 wt ° / 0 .
  • the phosphonic acid or phosphonate compound is 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid (HEDPA), aminotrimethylenephosphonic acid (ATMP) or 2 - Butane phosphonate-1,2,4-tricarboxylic acid (PBTCA), preferably 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid.
  • the content of the phosphonic acid or phosphonate compound is preferably from 0.001 to 15 wt%. More preferably, it is 0.01 to 5.0% by weight.
  • the solvent may be selected from the group consisting of sulfoxide, sulfone, imidazolidinone and/or mercaptodiol monoalkyl ether.
  • the content of the solvent is preferably from 55 to 99.90% by weight, more preferably from 60 to 95% by weight.
  • the sulfoxide is dimethyl sulfoxide, diethyl sulfoxide or methyl sulfoxide, preferably dimethyl sulfoxide;
  • the sulfone is methyl sulfone, ethyl sulfone or sulfolane.
  • the imidazolidone is 2-imidazolidinone (MI), 1,3-dimethyl-2-imidazolidinone (DMI) or 1,3-diethyl-2-imidazole
  • An alkyl ketone preferably 1,3-dimethyl-2-imidazolidinone
  • the alkyl diol monodecyl ether is ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol Monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol single Ether or dipropylene glycol monobutyl ether, preferably ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene
  • the photoresist cleaning agent may further comprise a quaternary ammonium hydroxide, a surfactant, and/or water.
  • the quaternary ammonium hydroxide is tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide or benzyltrimethylammonium hydroxide.
  • TMAH tetramethylammonium hydroxide
  • tetraethylammonium hydroxide or tetrabutylammonium hydroxide is preferred, and tetramethylammonium hydroxide is more preferred.
  • the surfactant is polyvinyl alcohol (PVA), polyvinylpyrrolidone (PVP), polyoxyethylene ether (POE) or polysiloxane (PSOA), preferably polyvinylpyrrolidone. Pyrrolidone or polyoxyethylene ether.
  • the content of the quaternary ammonium hydroxide is preferably from 0 to 15% by weight, more preferably from 0.5 to 5.0% by weight.
  • the content of the surfactant is preferably from 0 to 15% by weight, more preferably from 0.05 to 5.0% by weight.
  • the content of the water is preferably from 0 to 40% by weight, more preferably from 0.5 to 25% by weight.
  • the photoresist cleaning agent of the present invention can be obtained by simple mixing of the above components.
  • the photoresist cleaning agent of the present invention can be used as follows: The semiconductor wafer containing the photoresist is immersed in the cleaning agent, and slowly shaken at room temperature to 85 ° C for 15 to 30 minutes using a constant temperature oscillator. After washing with deionized water, it was dried with high purity nitrogen. If the cleaning temperature is above 45°, the wafer should be washed with isopropyl alcohol and then with deionized water.
  • the positive progress of the present invention is that the corrosion inhibitor in the photoresist cleaning agent forms a dense protective film on the surface of the wafer substrate through the intermolecular interaction with the surface material of the wafer substrate, and blocks halogen atoms and hydroxide ions. Waiting for the attack on the substrate, thereby reducing the corrosion of the substrate.
  • the photoresist cleaner can be used at room temperature to 85 °C.
  • Such a photoresist cleaning agent has good corrosion resistance to metals such as silicon dioxide, Cu (copper), and low-k materials, and has a good application prospect in the field of microelectronics such as semiconductor wafer cleaning. The effect will be explained by the comparative experiment in the examples.
  • Table 1 shows photoresist cleaning agents Examples 1-21. Table 1 photoresist cleaning agent embodiment 1-21.
  • Table 2 compares the components and contents of cleaning agent 1 and cleaning agent 1-7
  • the blank Cu wafer was cleaned using the comparative cleaning agent 1 and the cleaning agents 1 to 7 in Table 2, and the etching rate of the above cleaning agent for the metal Cu was measured.
  • Test methods and conditions Immerse a blank Cu wafer In the cleaning agent, slowly shake with a constant temperature oscillator at 25 ⁇ 85 ° C for 15 to 30 minutes, then wash with deionized water and then dry with high purity nitrogen (if the cleaning temperature is higher than 45 ⁇ , it should be washed first with isopropyl alcohol). The wafer was washed with deionized water, and the change in surface resistance of the blank Cu wafer before and after etching was measured by a quadrupole probe. The calculation results are shown in Table 3. Table 3 compares the etching rate of the cleaning agent 1 and the cleaning agent 1-7 to the blank Cu wafer
  • the raw materials and reagents used in the present invention are all commercially available products.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)
  • Cleaning Or Drying Semiconductors (AREA)

Abstract

La présente invention concerne une composition de nettoyage pour éliminer le photorésist comprenant un inhibiteur de corrosion et un solvant. L'inhibiteur de corrosion comprend deux types de composés : un type du composé étant un éther monoarylique d'alcool alkylique, l'autre type du composé étant choisi parmi un composé phénolique, un acide carboxylique, un acide polyocarboxylique, un carboxylate, un composé polycarboxylate, un anhydride, un polyanhydride et/ou un acide phosphinique, un composé ester de phosphonate.
PCT/CN2007/003019 2006-10-27 2007-10-22 Composé de nettoyage pour éliminer le photorésist WO2008052424A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200780037460XA CN101523298B (zh) 2006-10-27 2007-10-22 一种光刻胶清洗剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200610117668.X 2006-10-27
CNA200610117668XA CN101169598A (zh) 2006-10-27 2006-10-27 一种光刻胶清洗剂

Publications (1)

Publication Number Publication Date
WO2008052424A1 true WO2008052424A1 (fr) 2008-05-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2007/003019 WO2008052424A1 (fr) 2006-10-27 2007-10-22 Composé de nettoyage pour éliminer le photorésist

Country Status (2)

Country Link
CN (2) CN101169598A (fr)
WO (1) WO2008052424A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010060274A1 (fr) * 2008-11-28 2010-06-03 安集微电子（上海）有限公司 Détergent pour éliminer la résine photosensible

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101487993A (zh) * 2008-01-18 2009-07-22 安集微电子（上海）有限公司 一种厚膜光刻胶清洗剂
KR101288572B1 (ko) * 2008-12-17 2013-07-22 제일모직주식회사 보관안정성이 우수한 레지스트 하층막용 하드마스크 조성물
CN101914775A (zh) * 2010-06-29 2010-12-15 青岛大学 一种水溶性邻氨基苯甲酸聚合物碳钢酸洗缓蚀剂及其应用
CN102338994B (zh) * 2010-07-23 2014-12-31 安集微电子（上海）有限公司 一种光刻胶的清洗液
CN102346383B (zh) * 2010-08-06 2016-03-16 安集微电子（上海）有限公司 一种光刻胶的清洗液
CN102200700B (zh) * 2011-06-08 2012-08-22 绵阳艾萨斯电子材料有限公司 剥离液及其制备方法与应用
TW201311884A (zh) * 2011-09-13 2013-03-16 Anji Microelectronics Co Ltd 光阻（光刻）膠的清洗液
TW201311883A (zh) * 2011-09-13 2013-03-16 Anji Microelectronics Co Ltd 光阻（光刻）膠的清洗液
CN103543618A (zh) * 2013-09-27 2014-01-29 杨桂望 抗蚀膜剥离剂

Citations (7)

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JPH0680995A (ja) * 1992-08-31 1994-03-22 Asahi Chem Ind Co Ltd 低残渣洗浄剤
US5399285A (en) * 1992-10-30 1995-03-21 Diversey Corporation Non-chlorinated low alkalinity high retention cleaners
WO2004034451A1 (fr) * 2002-10-11 2004-04-22 Wako Pure Chemical Industries, Ltd. Detergent de substrat
WO2004059700A2 (fr) * 2002-12-20 2004-07-15 Advanced Technology Materials, Inc. Élimination de photorésine
US20050197265A1 (en) * 2004-03-03 2005-09-08 Rath Melissa K. Composition and process for post-etch removal of photoresist and/or sacrificial anti-reflective material deposited on a substrate
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
WO2006110645A2 (fr) * 2005-04-11 2006-10-19 Advanced Technology Materials, Inc. Agents nettoyants liquides au fluorure contenant des melanges de solvants polaires et non polaires destines a nettoyer des dispositifs microelectroniques a faible k

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US5962197A (en) * 1998-03-27 1999-10-05 Analyze Inc. Alkaline organic photoresist stripper

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0680995A (ja) * 1992-08-31 1994-03-22 Asahi Chem Ind Co Ltd 低残渣洗浄剤
US5399285A (en) * 1992-10-30 1995-03-21 Diversey Corporation Non-chlorinated low alkalinity high retention cleaners
WO2004034451A1 (fr) * 2002-10-11 2004-04-22 Wako Pure Chemical Industries, Ltd. Detergent de substrat
WO2004059700A2 (fr) * 2002-12-20 2004-07-15 Advanced Technology Materials, Inc. Élimination de photorésine
US20050197265A1 (en) * 2004-03-03 2005-09-08 Rath Melissa K. Composition and process for post-etch removal of photoresist and/or sacrificial anti-reflective material deposited on a substrate
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
WO2006110645A2 (fr) * 2005-04-11 2006-10-19 Advanced Technology Materials, Inc. Agents nettoyants liquides au fluorure contenant des melanges de solvants polaires et non polaires destines a nettoyer des dispositifs microelectroniques a faible k

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010060274A1 (fr) * 2008-11-28 2010-06-03 安集微电子（上海）有限公司 Détergent pour éliminer la résine photosensible

Also Published As

Publication number Publication date
CN101523298A (zh) 2009-09-02
CN101169598A (zh) 2008-04-30
CN101523298B (zh) 2012-04-04

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