WO2008052424A1 - A cleaning compound for removing photoresist - Google Patents
A cleaning compound for removing photoresist Download PDFInfo
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- 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
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- cleaning agent
- agent according
- ether
- photoresist cleaning
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- 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
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- 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
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- 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
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- 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
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- 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
Abstract
A cleaning composition for removing photoresist includes a corrosion inhibitor and a solvent. The corrosion inhibitor includes two types of compounds: one type of the compound being alkyl alcohol mono aryl ether, the other type of the compound selecting from a phenolic compound, carboxylic acid, polyocarboxy acid, carboxylate, polycarboxylate compound, anhydride, polyanhydride and/or phosphinic acid, phosphonate ester compound.
Description
一种光刻胶清洗剂 Photoresist cleaning agent
技术领域 Technical field
本发明涉及半导体制造中清洗工艺领域， 尤其涉及一种光刻胶清洗剂。 The present invention relates to the field of cleaning processes in semiconductor manufacturing, and more particularly to a photoresist cleaning agent.
技术背景 technical background
在通常的半导体制造工艺中， 通过在二氧化硅、 Cu (铜）等金属以及低 k材料等表面上形成光刻胶的掩模， 曝光后利用湿法或干法刻蚀进行图形转 移。在半导体晶片进行光刻胶的化学清洗过程中， 清洗剂常会造成晶片基材 的腐蚀。特别是在利用化学清洗剂除去金属刻蚀残余物的过程中， 金属腐蚀 是较为普遍而且非常严重的问题，往往导致晶片良率的显著降低。 In a conventional semiconductor manufacturing process, 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. In the chemical cleaning of photoresists on semiconductor wafers, cleaning agents often cause corrosion of the wafer substrate. In particular, in the process of removing metal etching residues by chemical cleaning agents, metal corrosion is a relatively common and very serious problem, often resulting in a significant reduction in wafer yield.
因此， 减少晶片清洗过程中的基材腐蚀是本领域亟待解决的问题。专利 文献 WO03104901利用反 -1,2-环己烷二胺四乙酸（CyDTA)为缓蚀剂， 其溶 液由四甲基氢氧化铵 （TMAH：)、 环丁砜（SFL)、 水和反 -1,2-环己烷二胺四 乙酸 （CyDTA) 等组成。 其对半导体晶片基材的腐蚀略高。 专利文献 WO04059700利用 2-巯基苯并咪唑（MBI)为缓蚀剂， 其溶液由四甲基氢氧 化铵（TMAH)、 N-甲基吗啡啉 氧化物（MO)、水和 2-巯基苯并咪唑（MBI) 等组成。 其对半导体晶片基材的腐蚀较高。
发明概要 Therefore, reducing substrate corrosion during wafer cleaning is an urgent problem to be solved in the art. 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. 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
本发明的目的是为了减少半导体制造工艺中清洗过程中的金属腐蚀，提 供一种光刻胶清洗剂。 SUMMARY OF THE 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.
本发明的上述目的是通过下列技术方案来实现的：本发明的光刻胶清洗 剂包含缓蚀剂和溶剂， 其特征在于所述的缓蚀剂包含两类化合物： 一类 ¾垸 基醇单芳基醚类化合物， 另一类选自酚类化合物， 羧酸、 聚羧酸、 羧酸酯、 聚羧酸酯类化合物， 酸酐、 聚酸酊类化合物或膦酸、 膦酸酯类化合物。 The above object of the present invention is achieved by the following technical solutions: 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.
本发明中， 所述的烷基醇单芳基醚类化合物为乙二醇单苯基醚 In the present invention, the alkyl alcohol monoaryl ether compound is ethylene glycol monophenyl ether
(EGMPE)、 丙二醇单苯基醚（PGMPE)、 异丙二醇单苯基醚、 二乙二醇单 苯基醚、 二丙二 Ιί单苯基醚、 二异丙二醇单苯基醚、 乙二醇单苄基醚、 丙二 醇单苄基醚或异丙二醇单苄基醚。其中， 较佳的为乙二醇单苯基醚、 丙二醇 单苯基醚或异丙二醇单苯基醚。所述的垸基醇单芳基醚类化合物的含量较佳 的为 0.05〜30wt%， 更佳的为 1.0~15wt%。 (EGMPE), propylene glycol monophenyl ether (PGMPE), 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. Among them, 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.
本发明中， 所述的酚类化合物为 1，2-二羟基苯酚、 对羟基苯酚或连苯三 酚， 较佳的为连苯三酚。 所述的酚类的含量较佳的为 0.001〜15wt%， 更佳的 为 0.01〜5.0wt%。 In the present invention, 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.
本发明中，所述的羧酸、聚羧酸、羧酸酯、聚羧酸酯类化合物为苯甲酸、 对氨基苯甲酸 （PABA)、 邻苯二甲酸 （PA)、 没食子酸 （GA)、 没食子酸丙 酯或含羧基的丙烯酸酯类聚合物。其中， 较佳的为对氨基苯甲酸、邻苯二甲 酸、 没食子酸。 所述的羧酸、 聚羧酸、 羧酸酯、 聚羧酸酯类化合物的含量较 佳的为 0.001〜15wt%， 更佳的为 0.01~5.0wt%。 In the present invention, 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. Among them, 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.
本发明中， 所述的酸酐、 聚酸酐类化合物为乙酸酐、 丙酸酐、 己酸酐、
马来酸酐或聚马来酸酐， 较佳的为聚马来酸酐。所述的酸酐、 聚酸酐类化合 物的含量较佳的为 0.001〜15wt°/。， 更佳的为 0.01〜5.0wt°/0。 In the present invention, 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 .
本发明中， 所述的膦酸、 膦酸酯类化合物为 1，3- (羟乙基） -2,4,6-三膦 酸 （HEDPA)、 氨基三亚甲基膦酸 （ATMP ) 或 2-膦酸丁烷 -1，2，4-三羧酸 (PBTCA), 较佳的为 1,3- (羟乙基） -2,4,6-三膦酸。所述的膦酸、膦酸酯类 化合物的含量较佳的为 0.001~15wt°/。， 更佳的为 0.01〜5.0wt%。 In the present invention, 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.
本发明中，所述的溶剂可选自亚砜、砜、咪唑烷酮和 /或垸基二醇单烷 醚。 所述的溶剂的含量较佳的为 55~99.90wt%， 更佳的为 60~95wt%。 In the present invention, 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.
其中， 所述的亚砜为二甲基亚砜、 二乙基亚砜或甲乙基亚砜， 较佳的为 二甲基亚砜； 所述的砜为甲基砜、 乙基砜或环丁砜， 较佳的为环丁砜； 所述 的咪唑烧酮为 2-咪唑烷酮（MI)、 1,3-二甲基 -2-咪唑烷酮（DMI) 或 1,3-二 乙基 -2-咪唑烷酮，'较佳的为 1,3-二甲基 -2-咪唑烷酮；所述的烷基二醇单垸基 醚为乙二醇单甲醚、 乙二醇单乙醚、 乙二醇单丁醚、 二乙二醇单甲醚、 二乙 二醇单乙醚、 二乙二醇单丁醚、 丙二醇单甲醚、 丙二醇单乙醚、 丙二醇单丁 醚、 二丙二醇单甲醚、 二丙二醇单乙醚或二丙二醇单丁醚， 较佳的为乙二醇 单甲醚、 二乙二醇单甲醚、 丙二醇单甲醚或二丙二醇单甲醚。 Wherein, the sulfoxide is dimethyl sulfoxide, diethyl sulfoxide or methyl sulfoxide, preferably dimethyl sulfoxide; the sulfone is methyl sulfone, ethyl sulfone or sulfolane. Preferred is 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 glycol monomethyl ether or dipropylene glycol monomethyl ether.
本发明中， 所述的光刻胶清洗剂还可进一步包含季铵氢氧化物、表面活 性剂和 /或水。 其中， 所述的季铵氢氧化物为四甲基氢氧化铵 （TMAH)、 四 乙基氢氧化铵、 四丙基氢氧化铵、 四丁基氢氧化铵或苄基三甲基氢氧化铵。 其中， 较佳的为四甲基氢氧化铵、 四乙基氢氧化铵或四丁基氢氧化铵， 更佳 的为四甲基氢氧化铵。 所述的表面活性剂为聚乙烯醇 （PVA)、 聚乙烯吡咯 垸酮（PVP)、聚氧乙烯醚（POE)或聚硅氧垸（PSOA), 较佳的为聚乙烯吡
咯烷酮或聚氧乙烯醚。所述的季铵氢氧化物的含量较佳的为 0〜15wt%，更佳 的为 0.5〜5.0wt%。 所述的表面活性剂的含量较佳的为 0〜15wt%， 更佳的为 0.05~5.0wt%。 所述的水的含量较佳的为 0〜40wt%， 更佳的为 0.5〜25wt%。 In the present invention, the photoresist cleaning agent may further comprise a quaternary ammonium hydroxide, a surfactant, and/or water. Wherein, the quaternary ammonium hydroxide is tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide or benzyltrimethylammonium hydroxide. Of these, 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.
本发明的光刻胶清洗剂可由上述组分的简单混合即可制得。 The photoresist cleaning agent of the present invention can be obtained by simple mixing of the above components.
本发明的光刻胶清洗剂， 可按下述方法使用： 将含有光刻胶的半导体晶 片浸入该清洗剂中，在室温至 85°C下，利用恒温振荡器缓慢振荡 15〜30分钟， 经去离子水洗涤后用高纯氮气吹干。若清洗温度高于 45° (，应先用异丙醇洗 涤晶片， 再用去离子水洗涤。 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.
本发明的积极进步效果在于：光刻胶清洗剂中的缓蚀剂通过与晶片基材 表面物质的分子间作用， 在晶片基材表面形成结构致密的保护膜， 阻止卤素 原子、氢氧根离子等对基材的攻击， 从而降低基材的腐蚀。 该光刻胶清洗剂 可以在室温至 85°C下使用。 这种光刻胶清洗剂对于二氧化硅、 Cu (铜）等 金属以及低 k材料等具有良好的防腐蚀性，在半导体晶片清洗等微电子领域 具有良好的应用前景。 其效果将通过实施例中的对比实验进- -步说明。 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.
发明内容 下面通过实施例的方式进一步说明本发明，并不因此将本发明限制在所 述的实施例范围之中。 The invention is further illustrated by the following examples, which are not intended to limit the invention to the scope of the embodiments.
实施例 1~21 Example 1~21
表 1给出了光刻胶清洗剂实施例 1~21。
表 1光刻胶清洗剂实施例 1-21 Table 1 shows photoresist cleaning agents Examples 1-21. Table 1 photoresist cleaning agent embodiment 1-21.
缓蚀剂 ' 溶剂 其它 实 Corrosion inhibitor 'solvent other real
垸基醇单芳基醚类化合物 另一类缓蚀剂 Mercapto alcohol monoaryl ether compound Another type of corrosion inhibitor
施 含量 含量 Application content
具体物质 具体物质 例 含量 含量 wt% wt% Specific substance specific substance example content content wt% wt%
具体物质 具体物质 Specific substance
wt% wt% Wt% wt%
1 0.099 二醇单苯基醚 0.001 1,2-二羟基苯酚 99.90 二乙基亚砜 \ \ 1 0.099 diol monophenyl ether 0.001 1,2-dihydroxyphenol 99.90 diethyl sulfoxide
2 30 丙二醇单苯基醚 15 对羟基苯酚 55 甲乙基亚砜 \ \2 30 propylene glycol monophenyl ether 15 p-hydroxyphenol 55 methyl ethyl sulfoxide
3 4.99 二乙二醇单苯基醚 0.01 连苯三酚 95 乙基砜 \ \3 4.99 diethylene glycol monophenyl ether 0.01 pyrogallol 95 ethyl sulfone
4 15 异丙二醇单苯 ¾醚 5 连苯三酚 65 甲基砜 15 四甲基氢氧化铵4 15 isopropyl glycol monophenyl 3⁄4 ether 5 pyrogallol 65 methyl sulfone 15 tetramethylammonium hydroxide
5 1 二丙二醇单苯基醚 2 连苯三酚 72 环丁砜 25 水5 1 dipropylene glycol monophenyl ether 2 pyrogallol 72 sulfolane 25 water
6 10 二异丙二醇单苯基醚 15 苯甲酸 60 2-咪唑烷酮 15 聚乙烯醇 6 10 Diisopropyl glycol monophenyl ether 15 Benzoic acid 60 2-Imidazolidinone 15 Polyvinyl alcohol
0.5 四乙基氢氧化铵 0.5 tetraethylammonium hydroxide
1,3--甲基 -2-咪 1,3-methyl-2-mer
7 4.449 乙二醇单苄基醚 0.001 对氨基苯甲酸 55 40 水 7 4.449 Ethylene glycol monobenzyl ether 0.001 p-Aminobenzoic acid 55 40 water
唑烷酮 Oxazolidinone
0.05 聚乙烯吡咯烷酮 0.05 polyvinylpyrrolidone
1,3-二乙基 -2-咪 1,3-diethyl-2-mi
8 10 丙二醇单节基醚 5 邻苯二甲酸 84.5 0.5 水 8 10 Propylene glycol monodecyl ether 5 Phthalic acid 84.5 0.5 water
唑垸酮 ' Zozolidone
9 12 异丙二醇单 基醚 0.01 没食子酸 82.99 乙二醇单甲醚 5 四丙基氢氧化铵 9 12 isopropyl glycol monoether 0.01 gallic acid 82.99 ethylene glycol monomethyl ether 5 tetrapropylammonium hydroxide
10 15 乙二醇单苯基醚 2 没食子酸丙酯 73 乙二醇单乙醚 10 水10 15 ethylene glycol monophenyl ether 2 propyl gallate 73 ethylene glycol monoethyl ether 10 water
11 10 乙二醇单苯基醚 1 聚丙烯酸酯 87 乙二醇单丁醚 2 四丁基氢氧化铵11 10 ethylene glycol monophenyl ether 1 polyacrylate 87 ethylene glycol monobutyl ether 2 tetrabutylammonium hydroxide
12 0.05 乙二醇单苯基醚 15 乙酸酐 84.95 二乙二醇单甲醚 \ \12 0.05 ethylene glycol monophenyl ether 15 acetic anhydride 84.95 diethylene glycol monomethyl ether \ \
13 10 乙二醇单苯基醚 5 丙酸酐 80 二乙二醇单乙酸 5 聚氧乙烯醚13 10 ethylene glycol monophenyl ether 5 propionic anhydride 80 diethylene glycol monoacetic acid 5 polyoxyethylene ether
14 10 乙二醇单苯基醚 2 己酸酐 86 二乙二醇单丁醚 2 聚硅氧烷14 10 ethylene glycol monophenyl ether 2 hexanoic anhydride 86 diethylene glycol monobutyl ether 2 polysiloxane
15 10 乙二醇单苯基醚 0.01 ■ 马来酸酐 89.99 丙二醇单甲醚 \ \ 苄基三甲基氢氧15 10 Ethylene Glycol Monophenyl Ether 0.01 ■ Maleic Anhydride 89.99 Propylene Glycol Monomethyl Ether \ \ Benzyl Trimethyl Hydrogen Oxygen
16 10 乙二醇单苯基醚 0.001 聚马来酸酐 79.999 丙二醇单乙醚 10 16 10 Ethylene glycol monophenyl ether 0.001 Polymaleic anhydride 79.999 Propylene glycol monoethyl ether 10
化铵 Ammonium
1，3- (羟乙基） -2,4,6-1,3-(hydroxyethyl)-2,4,6-
17 10 乙二醇单苯基醚 15 75 丙二醇单丁醚 \ \ 三膦酸 17 10 Ethylene glycol monophenyl ether 15 75 Propylene glycol monobutyl ether \ \ Triphosphonic acid
18 10 乙二醇单苯基醚 5 氣基三亚甲基膦酸 85 二丙二醇单甲醚 \ \ 18 10 ethylene glycol monophenyl ether 5 gas based trimethylene phosphonic acid 85 dipropylene glycol monomethyl ether
2-膦酸丁烷 -1，2,4- 2-phosphonate butane -1,2,4-
19 10 乙二醇单苯基醚 2 88 二丙二醇单乙醚 \ \ 三羧酸 19 10 Ethylene glycol monophenyl ether 2 88 Dipropylene glycol monoethyl ether \ \ Tricarboxylic acid
20 10 乙二醇单苯基醚 0.01 氣基 Ξ亚甲基膦酸 89.99 二丙二醇单丁醚 \ \ 20 10 Ethylene glycol monophenyl ether 0.01 Gas based Ξ Methylene phosphonic acid 89.99 Dipropylene glycol monobutyl ether
21 10 乙二醇单苯基醚 0.001 氨基三亚甲基膦酸 89.999 丙二醇单甲醚
效果实施例 1 21 10 Ethylene glycol monophenyl ether 0.001 Aminotrimethylene phosphonic acid 89.999 Propylene glycol monomethyl ether Effect Example 1
表 2对比清洗剂 1和清洗剂 1-7所含组分及其含量 Table 2 compares the components and contents of cleaning agent 1 and cleaning agent 1-7
由表 3可见， 与对比清洗剂 1相比， 清洗剂 1〜7对于金属 Cu表现出较 低的蚀刻性， 这说明清洗剂 1~7中的缓蚀剂对于金属 Cu具有良好的防腐蚀 性。 As can be seen from Table 3, compared with Comparative Cleaning Agent 1, Cleaning Agents 1 to 7 exhibited lower etching properties for metallic Cu, indicating that the corrosion inhibitors in Cleaning Agents 1 to 7 have good corrosion resistance to metallic Cu. .
本发明所使用的原料和试剂均为市售产品。
The raw materials and reagents used in the present invention are all commercially available products.
Claims
1.一种光刻胶清洗剂， 包含缓蚀剂和溶剂，其特征在于所述的缓蚀剂包 含两类化合物： 一类为烷基醇单芳基醚类化合物， 另一类选自酚类化合物， 羧酸、聚羧酸、羧酸酯、聚羧酸酯类化合物， 酸酐、聚酸酐类化合物或膦酸、 膦酸酯类化合物。 A photoresist cleaning agent comprising a corrosion inhibitor and a solvent, characterized in that the corrosion inhibitor comprises two types of compounds: one type is an alkyl alcohol monoaryl ether compound, and the other type is selected from a phenol a compound, a carboxylic acid, a polycarboxylic acid, a carboxylic acid ester, a polycarboxylate compound, an acid anhydride, a polyanhydride compound or a phosphonic acid or phosphonate compound.
2.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的烷基醇单 芳基醚类化合物为乙二醇单苯基醚、 丙二醇单苯基醚、 异丙二醇单苯基醚、 二乙二醇单苯基醚、 二丙二醇单苯基醚、 二异丙二醇单苯基醚、 乙二醇单苄 基醚、 丙二醇单苄基醚或异丙二醇单苄基醚。 The photoresist cleaning agent according to claim 1, wherein the alkyl alcohol monoaryl ether compound is ethylene glycol monophenyl ether, propylene glycol monophenyl ether, and isopropyl glycol monobenzene. Ethyl ether, diethylene glycol monophenyl ether, dipropylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monobenzyl ether or isopropyl glycol monobenzyl ether.
3.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的垸基醇单 芳基醚类化合物的含量为 0.05~30wt%。 The photoresist cleaning agent according to claim 1, wherein the mercapto alcohol monoaryl ether compound is contained in an amount of from 0.05 to 30% by weight.
4.根据权利要求 3所述的光刻胶清洗剂， 其特征在于： 所述的垸基醇单 芳基醚类化合物的含量为 1.0〜15wt%。 The photoresist cleaning agent according to claim 3, wherein the mercapto alcohol monoaryl ether compound is contained in an amount of from 1.0 to 15% by weight.
5.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的酚类化合 物为 1,2-二羟基苯酚、 对羟基苯酚或连苯三酚。 The photoresist cleaning agent according to claim 1, wherein the phenol compound is 1,2-dihydroxyphenol, p-hydroxyphenol or pyrogallol.
6.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的酚类化合 物的含量为 0.001〜15wt%。 The photoresist cleaning agent according to claim 1, wherein the phenolic compound is contained in an amount of from 0.001 to 15% by weight.
7.根据权利要求 6所述的光刻胶清洗剂， 其特征在于： 所述的酚类化合 物的含量为 0.01~5.0wt%。 The photoresist cleaning agent according to claim 6, wherein the phenolic compound is contained in an amount of from 0.01 to 5.0% by weight.
8.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的羧酸、聚 羧酸、 羧酸酯、 聚羧酸酯类化合物为苯甲酸、 对氨基苯甲酸、 邻苯二甲酸、 没食子酸、 没食子酸丙酯或含羧基的丙烯酸酯类聚合物。 The photoresist cleaning agent according to claim 1, wherein the carboxylic acid, polycarboxylic acid, carboxylate, and polycarboxylate compound are benzoic acid, p-aminobenzoic acid, ortho-benzene. Dicarboxylic acid, gallic acid, propyl gallate or a carboxyl group-containing acrylate polymer.
9.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的羧酸、聚 羧酸、 羧酸酯、 聚羧酸酯类化合物的含量为 0.001〜15wt%。 The photoresist cleaning agent according to claim 1, wherein the carboxylic acid, the polycarboxylic acid, the carboxylic acid ester, and the polycarboxylate compound are contained in an amount of 0.001 to 15% by weight.
10. 根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的羧酸、 聚羧酸、 羧酸酯、 聚羧酸酯类化合物的含量为 0.01~5.0wt%。
The photoresist cleaning agent according to claim 9, wherein the carboxylic acid, the polycarboxylic acid, the carboxylic acid ester, and the polycarboxylate compound are contained in an amount of 0.01 to 5.0% by weight.
11. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的酸酐、 聚酸酐类化合物为乙酸酐、 丙酸酐、 己酸酐、 马来酸酐或聚马来酸酐。 The photoresist cleaning agent according to claim 1, wherein the acid anhydride or polyanhydride compound is acetic anhydride, propionic anhydride, hexanoic anhydride, maleic anhydride or polymaleic anhydride.
12. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的酸酐、 聚酸酐类化合物的含量为 0.001〜15wt%。 The photoresist cleaning agent according to claim 1, wherein the content of the acid anhydride or polyanhydride compound is 0.001 to 15% by weight.
13. 根据权利要求 12所述的光刻胶清洗剂，其特征在于：所述的酸酐、 聚酸酐类化合物的含量为 0.01~5.0wt%。 The photoresist cleaning agent according to claim 12, wherein the content of the acid anhydride or polyanhydride compound is 0.01 to 5.0% by weight.
14. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的膦酸、 膦酸酯类化合物为 1，3- (羟乙基） -2，4,6-三膦酸、 氨基三亚甲基膦酸或 2-膦 酸丁垸 -1,2,4-三羧酸。 The photoresist cleaning agent according to claim 1, wherein the phosphonic acid or phosphonate compound is 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid. , aminotrimethylenephosphonic acid or 2-phosphonic acid butyl hydrazine-1,2,4-tricarboxylic acid.
15. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的膦酸、 膦酸酯类化合物的含量为 0.001〜15wt%。 The photoresist cleaning agent according to claim 1, wherein the phosphonic acid or phosphonate compound is contained in an amount of from 0.001 to 15% by weight.
16. 根据权利要求 15所述的光刻胶清洗剂，其特征在于：所述的膦酸、 膦酸酯类化合物的含量为 0.01〜5.0wt%。 The photoresist cleaning agent according to claim 15, wherein the content of the phosphonic acid or phosphonate compound is 0.01 to 5.0% by weight.
17. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的溶剂 为亚砜、 砜、 咪唑垸酮和 /或烷基二醇单烷基醚。 The photoresist cleaning agent according to claim 1, wherein the solvent is sulfoxide, sulfone, imidazolium and/or alkyl glycol monoalkyl ether.
18. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的溶剂 的含量为 55~99.90wt%。 The photoresist cleaning agent according to claim 1, wherein the solvent is contained in an amount of 55 to 99.90% by weight.
19. 根据权利要求 18所述的光刻胶清洗剂， 其特征在于： 所述的溶剂 的含量为 60~95wt%。 The photoresist cleaning agent according to claim 18, wherein the solvent is contained in an amount of 60 to 95% by weight.
20. 根据权利要求 17所述的光刻胶清洗剂， 其特征在于： 所述的亚砜 为二甲基亚砜、 二乙基亚砜或甲乙基亚砜。 The photoresist cleaning agent according to claim 17, wherein the sulfoxide is dimethyl sulfoxide, diethyl sulfoxide or methyl sulfoxide.
21. 根据权利要求 17所述的光刻胶清洗剂， 其特征在于： 所述的砜为 甲基砜.、 乙基砜或环丁砜。 The photoresist cleaning agent according to claim 17, wherein the sulfone is methyl sulfone, ethyl sulfone or sulfolane.
22. 根据权利要求 17所述的光刻胶清洗剂， 其特征在于： 所述的咪唑 烷酮为 2-咪唑烷酮、 1,3-二甲基 -2-咪唑烷酮或 1,3-二乙基 -2-咪唑院酮。 The photoresist cleaning agent according to claim 17, wherein the imidazolidinone is 2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone or 1,3- Diethyl-2-imidazole ketone.
23. 根据权利要求 17所述的光刻胶清洗剂， 其特征在于： 所述的烷基 二醇单烷基醚为乙二醇单甲醚、 乙二醇单乙醚、 乙二醇单丁醚、 二乙二醇单
甲醚、 二乙二醇单乙醚、 二乙二醇单丁醚、 丙二醇单甲醚、 丙二醇单乙醚、 丙二醇单丁醚、 二丙二醇单甲醚、 二丙二醇单乙醚或二丙二醇单丁醚。 The photoresist cleaning agent according to claim 17, wherein the alkyl glycol monoalkyl ether is ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether. Diethylene glycol single Methyl 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 monoethyl ether or dipropylene glycol monobutyl ether.
24. 根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的光刻 胶清洗剂还包含季铵氢氧化物、 表面活性剂和 /或水。 24. The photoresist cleaning agent according to claim 1, wherein: the photoresist cleaning agent further comprises a quaternary ammonium hydroxide, a surfactant, and/or water.
25. 根据权利要求 24所述的光刻胶清洗剂， 其特征在于： 所述的季铵 氢氧化物为四甲基氢氧化铵、 四乙基氢氧化铵、 四丙基氢氧化铵、 四丁基氢 氧化铵或苄基三甲基氢氧化铵。 The photoresist cleaning agent according to claim 24, wherein the quaternary ammonium hydroxide is tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetra Butyl ammonium hydroxide or benzyltrimethylammonium hydroxide.
26. 根据权利要求 24所述的光刻胶清洗剂， 其特征在于： 所述的表面 活性剂为聚乙烯醇、 聚乙烯吡咯垸酮、 聚氧乙烯醚或聚硅氧垸。 The photoresist cleaning agent according to claim 24, wherein the surfactant is polyvinyl alcohol, polyvinylpyrrolidone, polyoxyethylene ether or polysiloxane.
27. 根据权利要求 24所述的光刻胶清洗剂， 其特征在于： 所述的季铵 氢氧化物的含量为 0〜15wt%。 The photoresist cleaning agent according to claim 24, wherein the quaternary ammonium hydroxide is contained in an amount of from 0 to 15% by weight.
28. 根据权利要求 27所述的光刻胶清洗剂， 其特征在于： 所述的季铵 氢氧化物的含量为 0.5〜5.0wt%。 The photoresist cleaning agent according to claim 27, wherein the quaternary ammonium hydroxide is contained in an amount of from 0.5 to 5.0% by weight.
29. 根据权利要求 24所述的光刻胶清洗剂， 其特征在于： 所述的表面 活性剂的含量为 0〜15wt%。 The photoresist cleaning agent according to claim 24, wherein the surfactant is contained in an amount of from 0 to 15% by weight.
30. 根据权利要求 29所述的光刻胶清洗剂， 其特征在于： 所述的表面 活性剂的含量为 0.05~5.0wt%。 The photoresist cleaning agent according to claim 29, wherein the surfactant is contained in an amount of from 0.05 to 5.0% by weight.
31. 根据权利要求 24所述的光刻胶清洗剂， 其特征在于： 所述的水的 含量为 0~40wt%。 The photoresist cleaning agent according to claim 24, wherein the water has a content of 0 to 40% by weight.
32. 根据权利要求 31所述的光刻胶清洗剂， 其特征在于： 所述的水的 含量为 0.5〜25wt%。
The photoresist cleaning agent according to claim 31, wherein the water is contained in an amount of from 0.5 to 25 % by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200780037460XA CN101523298B (en) | 2006-10-27 | 2007-10-22 | A cleaning compound for removing photoresist |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA200610117668XA CN101169598A (en) | 2006-10-27 | 2006-10-27 | Photoresist detergent |
| CN200610117668.X | 2006-10-27 |
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| WO2008052424A1 true WO2008052424A1 (en) | 2008-05-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/CN2007/003019 WO2008052424A1 (en) | 2006-10-27 | 2007-10-22 | A cleaning compound for removing photoresist |
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| CN (2) | CN101169598A (en) |
| WO (1) | WO2008052424A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010060274A1 (en) * | 2008-11-28 | 2010-06-03 | 安集微电子（上海）有限公司 | Detergent for removing photo resist |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101487993A (en) * | 2008-01-18 | 2009-07-22 | 安集微电子（上海）有限公司 | Thick-film photo resist cleaning agent |
| KR101288572B1 (en) * | 2008-12-17 | 2013-07-22 | 제일모직주식회사 | Hardmask Composition Coated under Photoresist with Improved Storage Stability |
| CN101914775A (en) * | 2010-06-29 | 2010-12-15 | 青岛大学 | Water-soluble anthranilic acid polymer carbon steel acid cleaning inhibitor and application thereof |
| CN102338994B (en) * | 2010-07-23 | 2014-12-31 | 安集微电子（上海）有限公司 | Cleaning solution for photoresist |
| CN102346383B (en) * | 2010-08-06 | 2016-03-16 | 安集微电子（上海）有限公司 | A kind of cleaning fluid of photoresist |
| CN102200700B (en) * | 2011-06-08 | 2012-08-22 | 绵阳艾萨斯电子材料有限公司 | Stripping liquid as well as preparation method and application |
| TW201311884A (en) * | 2011-09-13 | 2013-03-16 | Anji Microelectronics Co Ltd | Photoresist cleaning solution |
| TW201311883A (en) * | 2011-09-13 | 2013-03-16 | Anji Microelectronics Co Ltd | Photoresist cleaning liquid |
| CN103543618A (en) * | 2013-09-27 | 2014-01-29 | 杨桂望 | Resist film remover |
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| Publication number | Publication date |
|---|---|
| CN101169598A (en) | 2008-04-30 |
| CN101523298A (en) | 2009-09-02 |
| CN101523298B (en) | 2012-04-04 |
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