WO2008046305A1 - Agent de nettoyage pour photoresist faiblement gravée et procédé de nettoyage correspondant - Google Patents

Agent de nettoyage pour photoresist faiblement gravée et procédé de nettoyage correspondant Download PDF

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Publication number
WO2008046305A1
WO2008046305A1 PCT/CN2007/002935 CN2007002935W WO2008046305A1 WO 2008046305 A1 WO2008046305 A1 WO 2008046305A1 CN 2007002935 W CN2007002935 W CN 2007002935W WO 2008046305 A1 WO2008046305 A1 WO 2008046305A1
Authority
WO
WIPO (PCT)
Prior art keywords
cleaning agent
ether
agent according
low
resist cleaning
Prior art date
Application number
PCT/CN2007/002935
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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 CNA2007800375301A priority Critical patent/CN101523300A/zh
Publication of WO2008046305A1 publication Critical patent/WO2008046305A1/fr

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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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping 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
    • 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 in particular to a low etch photoresist cleaning agent and a cleaning method therefor.
  • a photoresist mask is formed on the surface of a metal such as silicon dioxide, copper or the like, or a low-k material, and the pattern is transferred by wet or dry etching after exposure.
  • the higher pH cleaning agent can 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.
  • achieving a low temperature and rapid cleaning process is an important direction in the development of the field.
  • Patent document WO03104901 immersing a wafer into the cleaning agent by using an alkaline cleaning agent consisting of tetramethylammonium hydroxide (TMAH), sulfolane (SFL), trans-1,2-cyclohexanediaminetetraacetic acid (CyDTA), and water.
  • TMAH tetramethylammonium hydroxide
  • SFL sulfolane
  • CyDTA trans-1,2-cyclohexanediaminetetraacetic acid
  • water water.
  • the photoresist on the metal and dielectric substrates is removed by immersing at 20 to 30 ⁇ at 50 to 70 °C.
  • the cleaning agent has a slightly high corrosion to the semiconductor wafer substrate, and the photoresist of the semiconductor wafer cannot be completely removed, and the cleaning ability is insufficient.
  • Patent document WO04059700 immersing a wafer with an alkaline cleaning agent using tetramethylammonium hydroxide ( ⁇ ), ⁇ -methylmorpholine- ⁇ -oxide ( ⁇ ), 2-mercaptobenzimidazole ( ⁇ ) and water
  • the cleaning agent was immersed at 7 CTC for 15 to 60 minutes to remove the photoresist on the metal and dielectric substrates.
  • the cleaning temperature is relatively high, and the cleaning speed is relatively slow, which is not conducive to improving the cleaning efficiency of the semiconductor wafer.
  • Confirmation JP1998239865 uses an alkaline cleaning agent consisting of TMAH, dimethyl sulfoxide (DMSO), 1,3,-dimethyl-2-imidazolidinone (DMI) and water to immerse the wafer in the cleaning agent at 50 ⁇ 10 (rC removes 20 ⁇ m or more of thick film photoresist on metal and dielectric substrates.
  • TMAH dimethyl sulfoxide
  • DMI 1,3,-dimethyl-2-imidazolidinone
  • JP2001215736 utilizes tetramethylammonium hydroxide ( ⁇ ), two An alkaline cleaning agent is composed of methyl sulfoxide (DMSO), ethylene glycol (EG), and water, and the wafer is immersed in the cleaning agent to remove the photoresist on the metal and dielectric substrate at 50 to 70 °C. Similarly, the higher cleaning temperature causes corrosion of the semiconductor wafer substrate. JP200493678 uses an alkaline cleaning agent such as TMAH, N-methylpyrrolidone (NMP), water or methanol to immerse the wafer in the cleaning agent. The photoresist on the metal and dielectric substrates is removed at 25 to 85 ° C. However, the increase in the cleaning temperature causes a significant increase in the corrosion of the semiconductor wafer substrate.
  • TMAH methyl sulfoxide
  • EG ethylene glycol
  • water water
  • the object of the present invention is to reduce metal corrosion during cleaning in a semiconductor manufacturing process while also ensuring a low temperature of the cleaning process, providing a low etch photoresist cleaning agent.
  • the above object of the present invention is achieved by the following technical solutions:
  • the low etching photoresist cleaning agent of the present invention comprises dimethyl sulfoxide and quaternary ammonium hydroxide, and is characterized in that it further comprises the formula (1)
  • R 2 is H or an aryl group
  • m 2 to 6
  • n 1 to 6.
  • the alkyl glycol aryl ether or a derivative thereof is ethylene glycol monophenyl ether, propylene glycol monophenyl ether, isopropyl glycol monophenyl ether, diethylene glycol monophenyl ether, two Propylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monobenzyl ether, isopropyl glycol monobenzyl ether, hexanediol mononaphthyl ether or hexaethylene glycol diphenyl Ether.
  • ethylene glycol monophenyl is preferred.
  • the content thereof is preferably from 0.01 to 9 S.99 wt%, more preferably from 5.0 to 40.0 wt%.
  • the content of the dimethyl sulfoxide is preferably from 1 to 99.98% by weight, more preferably from 60 to 95% by weight.
  • the quaternary ammonium hydroxide is tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide or benzyltrimethylammonium hydroxide.
  • tetramethylammonium hydroxide, tetraethylammonium hydroxide or tetrabutylammonium hydroxide, more preferably tetramethylammonium hydroxide 9 is preferably 0.01 to 15% by weight, more preferably It is 0.5 to 10.0% by weight.
  • the low etch resist cleaning agent may further comprise a polar organic cosolvent, a corrosion inhibitor, a surfactant, and/or water.
  • the content of the polar organic co-solvent is preferably from 0 to 98.98 wt%, more preferably from 10 to 50 wt%;
  • the corrosion inhibitor content is preferably from 0 to 15 wt%, more preferably 0.05.
  • the surfactant content is preferably 0 ⁇ 15wt%, more preferably 0.05 ⁇ 5.0wt%;
  • the water content is preferably 0 ⁇ 95wt%, more preferably 0.5 ⁇ 25wt%.
  • the polar organic co-solvent is sulfoxide, sulfone, imidazolium and/or mercaptodiol monodecyl ether.
  • the sulfoxide is diethyl sulfoxide or methyl ethyl sulfoxide;
  • the sulfone is methyl sulfone, ethyl sulfone or sulfolane, preferably sulfolane;
  • the imidazolidinone is 2-imidazole An alkyl ketone, 1,3-dimethyl-2-imidazolium or 1,3-diethyl-2-imidazolium, preferably 1,3-dimethyl-2-imidazolium;
  • the mercapto diol monoalkyl 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 monobuty
  • the corrosion inhibitor is a phenolic, carboxylic acid (ester), acid anhydride or phosphonic acid (ester) corrosion inhibitor.
  • the phenol is 1,2-dihydroxyphenol, p-hydroxyphenol or pyrogallol, preferably pyrogallol;
  • the carboxylic acid is benzoic acid, p-aminobenzene Formic acid, phthalic acid, gallic acid or propyl gallate, preferably p-aminobenzoic acid, phthalic acid or gallic acid;
  • the acid anhydride is acetic anhydride, propionic anhydride, hexanoic anhydride or (poly) Maleic anhydride, preferably polymaleic acid;
  • the phosphonic acid type is 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid, aminotrimethylenephosphonic acid Or 2-phosphonium butyrate-1,2,4-tricarboxylic acid, preferably 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid.
  • the low etch resist cleaning agent can be obtained by simply mixing the components described above.
  • Another object of the present invention is to provide a cleaning method using the above-described low etching photoresist cleaning agent, the specific steps of which: immersing a semiconductor wafer containing a photoresist in the low etching property of the present invention at room temperature to 85 ° C The photoresist cleaner is cleaned and then blown dry.
  • the wafer is washed with a cleaning agent, and then the wafer is washed with isopropyl alcohol.
  • the cleaning method can be carried out by slow shaking, and the time is preferably 10 to 30 minutes.
  • the blow drying step is preferably carried out under high purity nitrogen.
  • the positive progress of the present invention is that the low etch resist cleaning agent is packaged therein.
  • the alkyl diol aryl ether or its derivative can form a protective film on the surface of the wafer substrate to prevent attack of the substrate by a halogen atom, a hydroxide ion or the like, thereby reducing corrosion of the substrate.
  • the cleaning agent can be used to remove photoresist (photoresist) and other residues of 30 ⁇ m or more on a metal, metal alloy or dielectric substrate, and has properties for metals such as silicon dioxide, Cu (copper), and low-k materials.
  • the low etching rate has a good application prospect in the field of microelectronics such as semiconductor wafer cleaning. The effect will be further illustrated by comparative experiments in the examples. Summary of the invention
  • the cleaning agents of Examples 27 to 34 in Table 1 and the cleaning agent of Comparative Example 1 were used to clean blank Cu wafers, and the etching rate of the metal Cu was measured. The results are shown in Table 2. Test Methods and Conditions - Dip the blank Cu wafer into the cleaning agent, shake it slowly for 30 minutes at a specific temperature listed in Table 2, then wash it with deionized water and then dry it with high purity nitrogen. Needle test The etch rate of the above-mentioned cleaning agent to the metal Cu was calculated by changing the surface resistance of the blank Cu wafer before and after etching.
  • Low etch photoresist cleaning agent 84.35wt% dimethyl sulfoxide, 2.50wt% tetramethylammonium hydroxide, 8.00 wt% ethylene glycol monophenyl ether, 0.15 wt% polyoxyethylene ether and 5.00 wt% water.
  • the photoresist-containing semiconductor wafer was immersed in a low-etching photoresist cleaning agent at room temperature for a period of 30 minutes, washed with deionized water, and then dried under high-purity nitrogen.
  • Low etch resist cleaning agent 84.35 wt % dimethyl sulfoxide, 2.50 wt % tetramethylammonium hydroxide, 8.00 wt % ethylene glycol monophenyl ether, 0.15 wt % polyoxyethylene ether and 5.00 wt % water.
  • the semiconductor wafer containing the photoresist is immersed in a low-etching photoresist cleaning agent at 45 ° C.
  • the mixture was washed for 20 min, washed with isopropyl alcohol, washed with deionized water, and then dried under high purity nitrogen.
  • Low etch photoresist cleaning agent 84.35 wt % dimethyl sulfoxide, 2.50 wt % tetramethylammonium hydroxide, 8.00 wt % ethylene glycol monophenyl ether, 0.15 wt % polyoxyethylene ether and 5.00 % water .
  • the semiconductor wafer containing the photoresist was immersed in a low-etching photoresist cleaning agent and slowly oscillated for 10 minutes, washed with isopropyl alcohol, washed with deionized water, and then dried under high-purity nitrogen.
  • the raw materials and reagents used in the present invention are all commercially available products.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)

Abstract

Agent de nettoyage pour photoresist faiblement gravée et procédé de nettoyage correspondant. Ledit agent de nettoyage comprend un diméthyl sulfoxyde un hydroxyde d'ammonium quaternaire, un alkyldiol aryl éther représenté par la formule générale R1O-[-(-CHmH2m-)-O-]n-R2, ou un dérivé de ce composé, dans laquelle R1 est aryle, R2 est H ou aryle, m vaut de 2 à 6, et n vaut de 1 à 6. L'agent de nettoyage peut s'utiliser pour éliminer la photorésist et autres résidus présents sur le métal, l'alliage métallique ou le substrat diélectrique. Cet agent de nettoyage présente un taux de gravure plus faible pour le dioxyde de silicium, un métal tel que le cuivre et un matériau à faible constante k et analogue.
PCT/CN2007/002935 2006-10-13 2007-10-12 Agent de nettoyage pour photoresist faiblement gravée et procédé de nettoyage correspondant WO2008046305A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CNA2007800375301A CN101523300A (zh) 2006-10-13 2007-10-12 一种低蚀刻性光刻胶清洗剂及其清洗方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200610117138.5 2006-10-13
CNA2006101171385A CN101162369A (zh) 2006-10-13 2006-10-13 一种低蚀刻性光刻胶清洗剂及其清洗方法

Publications (1)

Publication Number Publication Date
WO2008046305A1 true WO2008046305A1 (fr) 2008-04-24

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CN (2) CN101162369A (fr)
WO (1) WO2008046305A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102102008A (zh) * 2009-12-18 2011-06-22 安集微电子（上海）有限公司 一种水基玻璃磨削液及其使用方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009022477A1 (de) * 2009-05-25 2010-12-16 Universität Konstanz Verfahren zum Texturieren einer Oberfläche eines Halbleitersubstrates sowie Vorrichtung zum Durchführen des Verfahrens
CN102043356B (zh) * 2009-10-13 2012-09-26 奇美实业股份有限公司 清洗基板用洗净液组成物
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
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
KR101956352B1 (ko) * 2014-03-20 2019-03-08 동우 화인켐 주식회사 결정성 실리콘 웨이퍼의 텍스쳐 에칭액 조성물 및 텍스쳐 에칭방법
CN104450280B (zh) * 2014-11-17 2017-06-06 如皋市大昌电子有限公司 一种二极管半导体专用清洗液

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10239865A (ja) * 1997-02-24 1998-09-11 Jsr Corp ネガ型フォトレジスト用剥離液組成物
US5962197A (en) * 1998-03-27 1999-10-05 Analyze Inc. Alkaline organic photoresist stripper
EP1150172A2 (fr) * 2000-02-25 2001-10-31 Shipley Company LLC Procédé d'élimination de compositions antireflets
CN1724626A (zh) * 2004-07-22 2006-01-25 气体产品与化学公司 用于从基片上除去光致抗蚀剂和/或蚀刻残留物的组合物及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10239865A (ja) * 1997-02-24 1998-09-11 Jsr Corp ネガ型フォトレジスト用剥離液組成物
US5962197A (en) * 1998-03-27 1999-10-05 Analyze Inc. Alkaline organic photoresist stripper
EP1150172A2 (fr) * 2000-02-25 2001-10-31 Shipley Company LLC Procédé d'élimination de compositions antireflets
CN1724626A (zh) * 2004-07-22 2006-01-25 气体产品与化学公司 用于从基片上除去光致抗蚀剂和/或蚀刻残留物的组合物及其应用

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102102008A (zh) * 2009-12-18 2011-06-22 安集微电子（上海）有限公司 一种水基玻璃磨削液及其使用方法
CN102102008B (zh) * 2009-12-18 2014-07-23 安集微电子（上海）有限公司 一种水基玻璃磨削液及其使用方法

Also Published As

Publication number Publication date
CN101523300A (zh) 2009-09-02
CN101162369A (zh) 2008-04-16

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