WO2008049332A1 - A cleaning compound for removing photoresist - Google Patents

A cleaning compound for removing photoresist Download PDF

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Publication number
WO2008049332A1
WO2008049332A1 PCT/CN2007/003021 CN2007003021W WO2008049332A1 WO 2008049332 A1 WO2008049332 A1 WO 2008049332A1 CN 2007003021 W CN2007003021 W CN 2007003021W WO 2008049332 A1 WO2008049332 A1 WO 2008049332A1
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Prior art keywords
cleaning agent
ether
agent according
photoresist cleaning
photoresist
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PCT/CN2007/003021
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French (fr)
Chinese (zh)
Inventor
Libbert Hongxiu Peng
Robert Yongtao Shi
Bing Liu
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Anji Microelectronics (Shanghai) Co., Ltd.
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Priority to CNA2007800374807A priority Critical patent/CN101523299A/en
Publication of WO2008049332A1 publication Critical patent/WO2008049332A1/en

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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
    • G03F7/425—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 fabrication, and more particularly to a photoresist cleaning agent.
  • a photoresist mask is formed on a surface of a metal such as silicon dioxide, ⁇ ! (copper), or a low-k material, and the pattern is transferred by wet or dry etching after exposure.
  • a metal such as silicon dioxide, ⁇ ! (copper), or a low-k material
  • the pattern is transferred by wet or dry etching after exposure.
  • Fast cleaning process of a low temperature process is an important development direction for producing a semiconductor wafer 9
  • the chemical cleaning process of the semiconductor wafer into line photoresist, the cleaning agents often cause corrosion of the substrate wafer.
  • metal corrosion is a relatively common and very serious problem, often resulting in a significant reduction in wafer yield.
  • the photoresist cleaning agent is mainly composed of a polar organic solvent, a surfactant, and/or water, and the photoresist on the semiconductor wafer is removed by immersing the semiconductor wafer in a cleaning agent or rinsing the semiconductor wafer with a cleaning agent.
  • Patent document US5863346 and patent document WO9739092 use dodecylbenzenesulfonic acid as a surfactant and a photoresist cleaning agent with m-diisopropylbenzene to immerse the wafer in the cleaning agent at 65-80 ° C.
  • the photoresist on the metal substrate is removed.
  • the corrosion of the semiconductor wafer substrate is high, and the photoresist on the semiconductor wafer cannot be completely removed, and the cleaning ability is insufficient.
  • Patent document US6368421 and patent document WO0003306 use BASF Plurafac® B-26 linear alkoxy alcohol as a surfactant, and a photoresist cleaning agent composed of sulfolane (SFL), dipropylene glycol monomethyl ether (DPGME) and deionized water.
  • SFL sulfolane
  • DPGME dipropylene glycol monomethyl ether
  • the wafer is immersed in the cleaning agent to remove the photoresist on the metal and dielectric substrates at 25 to 85 Torr. This photoresist cleaning agent cannot completely remove the photoresist on the semiconductor wafer, cleaning energy Not enough.
  • the photoresist cleaning agent of the present invention comprises dimethyl sulfoxide and quaternary ammonium hydroxide, and is characterized by further comprising a surfactant: a hydroxyl group-containing polyether (HPE).
  • HPE hydroxyl group-containing polyether
  • the hydroxyl-containing polyether can improve the amount of quaternary ammonium hydroxide dissolved in the cleaning agent and the ability of the cleaning agent to wet the semiconductor wafer substrate.
  • the content of the hydroxyl group-containing polyether is preferably 0.001 to 15% by weight, more preferably 0.05 to 5.0% by weight ; and the content of the dimethyl sulfoxide is preferably 70 to 99% by weight, more Preferably, the content of the quaternary ammonium hydroxide is from 0.01 to 15% by weight, more preferably from 5.0 to 10% by weight.
  • the quaternary ammonium hydroxide is preferably tetramethylammonium hydroxide (TMAH:), tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide or benzyltrimethyl. Based on ammonium hydroxide. Of these, tetramethylammonium hydroxide, tetraethylammonium hydroxide or tetrabutylammonium hydroxide is more preferred, and tetramethylammonium hydroxide is most preferred.
  • TMAH tetramethylammonium hydroxide
  • tetraethylammonium hydroxide or tetrabutylammonium hydroxide is more preferred, and tetramethylammonium hydroxide is most preferred.
  • the photoresist cleaning agent may further comprise a polar organic co-solvent.
  • the content of the polar organic co-solvent is preferably from 0 to 29.5 wt%, more preferably from 5.0 to 25 wt%.
  • the polar organic co-solvent is preferably selected from the group consisting of sulfoxides, sulfones, imidazolidinones, alkyl glycol monoalkyl ethers and/or alkyl glycol aryl ethers.
  • the sulfoxide is preferably diethyl sulfoxide or methyl sulfoxide; and the sulfone is preferably methyl sulfone, ethyl sulfone and sulfolane, more preferably sulfolane;
  • Imidazoxone is preferably 2-imidazolidinone (MI), 1,3-dimethyl-2-imidazolium (DMI) or 1,3-diethyl- 2- imidazolidinone, more preferably Is 1,3-dimethyl-2-imidazolium;
  • the mercaptodiol monoalkyl ether is preferably 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, prop
  • POMPE isopropyl glycol monophenyl ether, diethylene glycol monophenyl ether, dipropylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monobenzyl ether or different Propylene glycol monobenzyl ether, more preferably ethylene glycol monophenyl ether or propylene glycol monophenyl ether.
  • the photoresist cleaning agent may further comprise water.
  • the water content is preferably 0 29.5 wt%, more preferably 0.5 to 25 wt%.
  • the photoresist cleaning agent may further comprise a corrosion inhibitor.
  • the content of the corrosion inhibitor is preferably from 0 to 10% by weight, more preferably from 0.05 to 5.0% by weight.
  • the corrosion inhibitor is selected from the group consisting of phenols, carboxylic acid (esters), acid anhydrides or phosphonates.
  • the phenol is preferably 1,2-dihydroxyphenol, p-hydroxyphenol or pyrogallol, more preferably pyrogallol; and the carboxylic acid is preferably Benzoic acid, p-aminobenzoic acid (PABA), phthalic acid (PA), gallic acid (GA) or propyl gallate, more preferably p-aminobenzoic acid, phthalic acid or gallic acid;
  • the acid anhydrides are preferably acetic anhydride, cesium propionate, hexanoic anhydride or (poly)maleic anhydride, more preferably polymaleic anhydride;
  • the phosphonic acid type is preferably 1,3- ( Hydroxyethyl)-2,4,6-triphosphonic acid (HEDPA), aminotrimethylenephosphonic acid (ATMP) or 2-phosphonic acid butane-1,2,4-tricarboxylic acid (PBTCA), more preferably The 1,3-(hydroxyethyl)-2,4,6-triphosphin
  • the photoresist cleaning agent of the present invention can be used as follows: a photoresist-coated semiconductor crystal The sheet is immersed in the photoresist cleaning agent of the invention, and is slowly shaken for 10 to 30 minutes at room temperature to 85 ° C using a constant temperature oscillator, washed with deionized water and then dried with high purity nitrogen gas (if the cleaning temperature is higher than 45 ° C) The wafer should be washed first with isopropyl alcohol and then with deionized water).
  • the positive progress of the present invention is that the photoresist cleaning agent of the present invention contains a hydroxyl group-containing polyether surfactant.
  • the hydroxyl-containing polyether can increase the amount of quaternary ammonium hydroxide dissolved in the cleaning agent and the ability of the cleaning agent to wet the semiconductor wafer substrate.
  • the photoresist cleaning agent of the invention has good cleaning ability for photoresist (photoresist) and other residues on metal, metal alloy or dielectric substrate, and can remove ⁇ ⁇ on the semiconductor wafer from room temperature to 85 ° C.
  • the photoresist of thickness ⁇ has a good application prospect in the field of microelectronics such as semiconductor wafer cleaning. The effect will be further explained by comparative experiments in the examples.
  • Table 1 shows Examples 1 to 32 of the photoresist cleaning agent.
  • 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

A cleaning composition for removing photoresist includes a dimethylsulfone, a quaternary ammonium hydroxide, characterized in that further includes a surfactant, the surfactant is a hydroxyl-containing polyether. The cleaning composition including the surfactant of the hydroxyl-containing polyether is used to clean photoresist on the metal, metal alloy or dielectric substrate.

Description

一种光刻胶清洗剂 技术领域  Photoresist cleaning agent
本发明涉及半导体制造中的清洗工艺领域， 尤其涉及一种光刻胶清洗 剂。  The present invention relates to the field of cleaning processes in semiconductor fabrication, 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、 θ! (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迸行图形转 移。低温快速的清洗工艺是半导体晶片制造工艺发展的重要方向 9另外， 在 半导体晶片迸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 typical semiconductor manufacturing process, a photoresist mask is formed on a surface of a metal such as silicon dioxide, θ! (copper), or a low-k material, and the pattern is transferred by wet or dry etching after exposure. . Fast cleaning process of a low temperature process is an important development direction for producing a semiconductor wafer 9 Further, the chemical cleaning process of the semiconductor wafer into line photoresist, the cleaning agents often cause corrosion of the substrate wafer. 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.
目前， 光刻胶清洗剂主要由极性有机溶剂、 表面活性剂和 /或水等组成， 通过将半导体晶片浸入清洗剂中或者利用清洗剂冲洗半导体晶片，去除半导 体晶片上的光刻胶。  Currently, the photoresist cleaning agent is mainly composed of a polar organic solvent, a surfactant, and/or water, and the photoresist on the semiconductor wafer is removed by immersing the semiconductor wafer in a cleaning agent or rinsing the semiconductor wafer with a cleaning agent.
专利文献 US5863346和专利文献 WO9739092以十二烷基苯磺酸为表面 活性剂， 与间 -二异丙基苯组成光刻胶清洗剂， 将晶片浸入该清洗剂中， 于 65~80°C下除去金属基材上的光刻胶。 其对半导体晶片基材的腐蚀较高， 且 不能完全去除半导体晶片上的光刻胶， 清洗能力不足。专利文献 US6368421 和专利文献 WO0003306以 BASF Plurafac® B-26线型烷氧基醇为表面活性 剂， 与环丁砜（SFL)、 二丙二醇单甲醚（DPGME) 和去离子水等组成光刻 胶清洗剂， 将晶片浸入该清洗剂中， 于 25〜85Ό下除去金属和电介质基材上 的光刻胶。这种光刻胶清洗剂不能完全去除半导体晶片上的光刻胶， 清洗能 力不足。 Patent document US5863346 and patent document WO9739092 use dodecylbenzenesulfonic acid as a surfactant and a photoresist cleaning agent with m-diisopropylbenzene to immerse the wafer in the cleaning agent at 65-80 ° C. The photoresist on the metal substrate is removed. The corrosion of the semiconductor wafer substrate is high, and the photoresist on the semiconductor wafer cannot be completely removed, and the cleaning ability is insufficient. Patent document US6368421 and patent document WO0003306 use BASF Plurafac® B-26 linear alkoxy alcohol as a surfactant, and a photoresist cleaning agent composed of sulfolane (SFL), dipropylene glycol monomethyl ether (DPGME) and deionized water. The wafer is immersed in the cleaning agent to remove the photoresist on the metal and dielectric substrates at 25 to 85 Torr. This photoresist cleaning agent cannot completely remove the photoresist on the semiconductor wafer, cleaning energy Not enough.
发明概要 Summary of invention
本发明的目的是提供一种具有良好清洗能力的光刻胶清洗剂。  It is an object of the present invention to provide a photoresist cleaning agent having good cleaning ability.
本发明中的光刻胶清洗剂包含二甲基亚砜、季铵氢氧化物， 其特征在于 还含有表面活性剂： 含羟基聚醚 （HPE)。 含羟基聚醚可以提髙清洗剂中季 铵氢氧化物的溶解量， 以及清洗剂对半导体晶片基材的浸润能力。  The photoresist cleaning agent of the present invention comprises dimethyl sulfoxide and quaternary ammonium hydroxide, and is characterized by further comprising a surfactant: a hydroxyl group-containing polyether (HPE). The hydroxyl-containing polyether can improve the amount of quaternary ammonium hydroxide dissolved in the cleaning agent and the ability of the cleaning agent to wet the semiconductor wafer substrate.
其中， 所述的含羟基聚醚的含量较佳的为 0.001~15wt%， 更佳的为 0.05~5.0wt%; 所述的二甲基亚砜的含量较佳的为 70〜99wt%， 更佳的为 80~99wt%; 所述的季铵氢氧化物的含量较佳的为 0.01〜15wt%， 更佳的为 Q.5〜10wt%。 Wherein, the content of the hydroxyl group-containing polyether is preferably 0.001 to 15% by weight, more preferably 0.05 to 5.0% by weight ; and the content of the dimethyl sulfoxide is preferably 70 to 99% by weight, more Preferably, the content of the quaternary ammonium hydroxide is from 0.01 to 15% by weight, more preferably from 5.0 to 10% by weight.
本发明中， 所述的季铵氢氧化物较佳的为四甲基氢氧化铵 （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， 更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， 最佳 的为四甲基氢氧化铵。  In the present invention, the quaternary ammonium hydroxide is preferably tetramethylammonium hydroxide (TMAH:), tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide or benzyltrimethyl. Based on ammonium hydroxide. Of these, tetramethylammonium hydroxide, tetraethylammonium hydroxide or tetrabutylammonium hydroxide is more preferred, and tetramethylammonium hydroxide is most preferred.
本发明中， 所述的光刻胶清洗剂还可进一步包含极性有机共溶剂。所述 的极性有机共溶剂的含量较佳的为 0~29.5wt%， 更佳的为 5.0〜25wt%。 所述 的极性有机共溶剂较佳的选自亚砜、 砜、 咪唑烷酮、 烷基二醇单烷基醚和 / 或烷基二醇芳基醚。其中，所述的亚砜较佳的为二乙基亚砜或甲乙基亚砜等； 所述的砜较佳的为甲基砜、 乙基砜和环丁砜， 更佳的为环丁砜； 所述的咪唑 垸酮较佳的为 2-咪唑烷酮 （MI)、 1,3-二甲基 -2-咪唑垸酮 （DMI)或 1，3-二 乙基 _2_咪唑烷酮，更佳的为 1,3-二甲基 -2-咪唑垸酮；所述的垸基二醇单烷基 醚较佳的为乙二醇单甲醚、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， 更佳的为^ 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； 所述的烷 棊二醇芳基醚为较佳的为乙二醇单苯基醚 （EGMPE)、 丙二醇单苯基醚In the present invention, the photoresist cleaning agent may further comprise a polar organic co-solvent. The content of the polar organic co-solvent is preferably from 0 to 29.5 wt%, more preferably from 5.0 to 25 wt%. The polar organic co-solvent is preferably selected from the group consisting of sulfoxides, sulfones, imidazolidinones, alkyl glycol monoalkyl ethers and/or alkyl glycol aryl ethers. Wherein, the sulfoxide is preferably diethyl sulfoxide or methyl sulfoxide; and the sulfone is preferably methyl sulfone, ethyl sulfone and sulfolane, more preferably sulfolane; Imidazoxone is preferably 2-imidazolidinone (MI), 1,3-dimethyl-2-imidazolium (DMI) or 1,3-diethyl- 2- imidazolidinone, more preferably Is 1,3-dimethyl-2-imidazolium; the mercaptodiol monoalkyl ether is preferably 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 monoethyl ether or dipropylene glycol monobutyl ether, more preferably ^ Glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether or dipropylene glycol monomethyl ether; the alkyl alkanediol aryl ether is preferably ethylene glycol monophenyl ether (EGMPE) Propylene glycol monophenyl ether
(POMPE), 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， 更佳的为乙二醇单苯基醚或丙二醇单苯基醚。 (POMPE), isopropyl glycol monophenyl ether, diethylene glycol monophenyl ether, dipropylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monobenzyl ether or different Propylene glycol monobenzyl ether, more preferably ethylene glycol monophenyl ether or propylene glycol monophenyl ether.
本发明中， 所述的光刻胶清洗剂还可进一步包含水。所述的水的含量较 佳的为 0 29.5 wt%， 更佳的为 0.5~25wt%。  In the present invention, the photoresist cleaning agent may further comprise water. The water content is preferably 0 29.5 wt%, more preferably 0.5 to 25 wt%.
本发明中， 所述的光刻胶清洗剂还可进一步包含缓蚀剂。所述的缓蚀剂 的含量较佳的为 0〜10wt%，更佳的为 0.05〜5.0wt%。所述的缓蚀剂选自酚类、 羧酸 （酯）类、 酸酐类或膦酸 （酯）类缓蚀剂。  In the present invention, the photoresist cleaning agent may further comprise a corrosion inhibitor. The content of the corrosion inhibitor is preferably from 0 to 10% by weight, more preferably from 0.05 to 5.0% by weight. The corrosion inhibitor is selected from the group consisting of phenols, carboxylic acid (esters), acid anhydrides or phosphonates.
其中， 所述的酚类较佳的为 1,2-二羟基苯酚、 对羟基苯酚或连苯三酚， 更佳的为连苯三酚； 所述的羧酸 （酯）类较佳的为苯甲酸、 对氨基苯甲酸 (PABA)、邻苯二甲酸（PA)、没食子酸（GA)或没食子酸丙酯， 更佳的为 对氨基苯甲酸、 邻苯二甲酸或没食子酸； 所述的酸酐类较佳的为乙酸酐、 丙 酸酑、 己酸酐或（聚）马来酸酐， 更佳的为聚马来酸酐； 所述的膦酸（酯） 类较佳的为 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), 更佳的为 1,3- (羟乙基） -2,4,6-三膦 本发明的光刻胶清洗剂可由上述组分简单混合制得。  Wherein, the phenol is preferably 1,2-dihydroxyphenol, p-hydroxyphenol or pyrogallol, more preferably pyrogallol; and the carboxylic acid is preferably Benzoic acid, p-aminobenzoic acid (PABA), phthalic acid (PA), gallic acid (GA) or propyl gallate, more preferably p-aminobenzoic acid, phthalic acid or gallic acid; The acid anhydrides are preferably acetic anhydride, cesium propionate, hexanoic anhydride or (poly)maleic anhydride, more preferably polymaleic anhydride; the phosphonic acid type is preferably 1,3- ( Hydroxyethyl)-2,4,6-triphosphonic acid (HEDPA), aminotrimethylenephosphonic acid (ATMP) or 2-phosphonic acid butane-1,2,4-tricarboxylic acid (PBTCA), more preferably The 1,3-(hydroxyethyl)-2,4,6-triphosphine photoresist cleaning agent of the present invention can be obtained by simply mixing the above components.
本发明的光刻胶清洗剂， 可按下述方法使用： 将覆有光刻胶的半导体晶 片浸入本发明的光刻胶清洗剂， 在室温至 85°C下利用恒温振荡器缓慢振荡 10~30分钟， 利用去离子水洗涤后用高纯氮气吹干 （若清洗温度高于 45°C， 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: a photoresist-coated semiconductor crystal The sheet is immersed in the photoresist cleaning agent of the invention, and is slowly shaken for 10 to 30 minutes at room temperature to 85 ° C using a constant temperature oscillator, washed with deionized water and then dried with high purity nitrogen gas (if the cleaning temperature is higher than 45 ° C) The wafer should be washed first with isopropyl alcohol and then with deionized water).
本发明的积极进步效果在于：本发明中光刻胶清洗剂含有含羟基聚醚表 面活性剂。含羟基聚醚可以提高清洗剂中季铵氢氧化物的溶解量， 以及清洗 剂对半导体晶片基材的浸润能力。本发明的光刻胶清洗剂对于金属、金属合 金或电介质基材上的光刻胶（光阻）和其它残留物具有良好的清洗能力， 可 以在室温至 85°C下去除半导体晶片上 Ιθ μ ιη以上厚度的光刻胶， 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 实验进一步说明。  The positive progress of the present invention is that the photoresist cleaning agent of the present invention contains a hydroxyl group-containing polyether surfactant. The hydroxyl-containing polyether can increase the amount of quaternary ammonium hydroxide dissolved in the cleaning agent and the ability of the cleaning agent to wet the semiconductor wafer substrate. The photoresist cleaning agent of the invention has good cleaning ability for photoresist (photoresist) and other residues on metal, metal alloy or dielectric substrate, and can remove Ιθ μ on the semiconductor wafer from room temperature to 85 ° C. The photoresist of thickness ιη has a good application prospect in the field of microelectronics such as semiconductor wafer cleaning. The effect will be further explained by comparative experiments in the examples.
发明内容 Summary of the invention
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 scope of the invention.
实施例 1-32 Example 1-32
表 1给出了光刻胶清洗剂的实施例 1〜32。  Table 1 shows Examples 1 to 32 of the photoresist cleaning agent.
表 1光刻胶清洗剂实施例 1-32  Table 1 Photoresist Cleaning Agent Example 1-32
二甲基亚砜 季铵氢氧化物 含羟基聚醚 其它  Dimethyl sulfoxide quaternary ammonium hydroxide hydroxyl-containing polyether
实施例  Example
含量％ 含量％ 具体物质 含量％ 含量％ 具体物质  Content % Content % Specific substance Content % Content % Specific substance
1 99 0.5 四甲基氢氧化铵 0.5 \ \  1 99 0.5 tetramethylammonium hydroxide 0.5 \ \
2 70 15 四乙基氢氧化铵 5 10 苯甲酸  2 70 15 Tetraethylammonium hydroxide 5 10 Benzoic acid
3 70.489 0.01 四丙基氢氧化铵 0.001 29.5 水  3 70.489 0.01 tetrapropylammonium hydroxide 0.001 29.5 water
4 70 0.45 四丁基氢氧化铵 0.05 29.5 二乙基亚砜  4 70 0.45 Tetrabutylammonium hydroxide 0.05 29.5 Diethyl sulfoxide
5 甲乙基亚砜， 5 methyl sulfoxide,
5 79 0.45 苄基三甲基氢氧化铵 15 0.05 1,2-二羟基苯酚 5 79 0.45 benzyltrimethylammonium hydroxide 15 0.05 1,2-dihydroxyphenol
0.5 水 1 甲基砜 0.5 water 1 methyl sulfone
70 3 四甲基氢氧化铵 0.5 0.5 连苯三酚  70 3 tetramethylammonium hydroxide 0.5 0.5 pyrogallol
25 水  25 water
5 ' 乙基砜  5 'ethyl sulfone
80 10 四甲基氢氧化铵 3  80 10 tetramethylammonium hydroxide 3
2 ' 对羟基苯酚' . 2 ' p-hydroxyphenol'.
25 环丁砜 ' 25 sulfolane '
70 2.5 四甲基氢氧化铵 2  70 2.5 tetramethylammonium hydroxide 2
0.5 对氨基苯甲酸  0.5 p-aminobenzoic acid
5 2-咪唑烷酮  5 2-imidazolidinone
70 10 四甲基氢氧化铵 10  70 10 tetramethylammonium hydroxide 10
5 邻苯二甲酸  5 phthalic acid
18 1,3-二甲基 -2-咪唑垸酮 18 1,3-dimethyl-2-imidazolium
80 1.2 四甲基氢氧化铵 0.5 80 1.2 tetramethylammonium hydroxide 0.5
0.3 没食子酸  0.3 gallic acid
18 1，3-二乙基 -2-咪唑烷酮 18 1,3-diethyl-2-imidazolidinone
80 1.2 四乙基氢氧化铵 0.5 80 1.2 Tetraethylammonium hydroxide 0.5
0.3 没食子酸丙酯  0.3 propyl gallate
18 乙二醇单甲醚  18 ethylene glycol monomethyl ether
80 . 1.2 四乙基氢氧化铵 0.5  80 . 1.2 Tetraethylammonium hydroxide 0.5
0.3 乙酸酐  0.3 acetic anhydride
18 乙二醇单乙醚  18 ethylene glycol monoethyl ether
80 1.2 四乙基氢氧化铵 0.5  80 1.2 Tetraethylammonium hydroxide 0.5
0.3 丙酸酐  0.3 propionic anhydride
18 乙二醇单丁醚  18 ethylene glycol monobutyl ether
80 1.2 四乙基氢氧化铵 0.5  80 1.2 Tetraethylammonium hydroxide 0.5
0.3 己酸酐  0.3 hexanoic anhydride
18 二^二醇单甲醚  18 diethylene glycol monomethyl ether
80 1.2 四乙基氢氧化铵 0.5  80 1.2 Tetraethylammonium hydroxide 0.5
0.3 马来酸酐  0.3 maleic anhydride
18 二乙二醇单乙醚  18 diethylene glycol monoethyl ether
80 1.2 四乙基氢氧化铵 0.5  80 1.2 Tetraethylammonium hydroxide 0.5
0.3 聚马来酸酐  0.3 polymaleic anhydride
18 二乙二醇单丁醚  18 diethylene glycol monobutyl ether
80 1.2 四丙基氢氧化铵 0.5  80 1.2 tetrapropylammonium hydroxide 0.5
0.3 1,3- (羟乙基) -2,4,6-三膦酸 0.3 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid
18 丙二醇单甲醚 18 propylene glycol monomethyl ether
80 1.2 四丙基氢氧化铵 0.5  80 1.2 tetrapropylammonium hydroxide 0.5
0.3 氨基三亚甲基膦酸 . 0.3 aminotrimethylenephosphonic acid.
18 . 丙二醇单乙醚 18. Propylene glycol monoethyl ether
80 1.2 四丙基氢氧化铵 0.5  80 1.2 tetrapropylammonium hydroxide 0.5
0.3 2-膦酸丁烷 -1,2,4-三羧酸 0.3 2-phosphonic acid butane -1,2,4-tricarboxylic acid
10 丙二醇单丁醚 10 propylene glycol monobutyl ether
80 1 四丙基氢氧化铵 0.5 4 甲基砜  80 1 tetrapropylammonium hydroxide 0.5 4 methyl sulfone
4.5 2-咪唑烷酮  4.5 2-imidazolidinone
85 2 四丁基氢氧化铵 0.2 12.8 二丙二醇单甲醚 22 85 2 四丁基氢氧化铵 0.2 12.8 二丙二醇单乙醚85 2 tetrabutylammonium hydroxide 0.2 12.8 dipropylene glycol monomethyl ether 22 85 2 tetrabutylammonium hydroxide 0.2 12.8 dipropylene glycol monoethyl ether
23 85 2 四丁基氢氧化铵 0.2 12.8 二丙二醇单丁醚23 85 2 tetrabutylammonium hydroxide 0.2 12.8 dipropylene glycol monobutyl ether
24 85 2 四丁基氢氧化铵 0.2 12.8 乙二醇单笨基醚24 85 2 tetrabutylammonium hydroxide 0.2 12.8 ethylene glycol mono-phenyl ether
25 85 2 四丁基氢氧化铵 0.2 12.8 丙二醇单苯基醚25 85 2 tetrabutylammonium hydroxide 0.2 12.8 propylene glycol monophenyl ether
26 85 2 四丁基氢氧化铵 0.2 12.8 异丙二醇单苯基醚26 85 2 tetrabutylammonium hydroxide 0.2 12.8 isopropyl glycol monophenyl ether
27 85 2 四丁基氢氧化铵 0.2 12.8 二乙二醇单苯基醚27 85 2 tetrabutylammonium hydroxide 0.2 12.8 diethylene glycol monophenyl ether
28 85 2 四丁基氢氧化铵 0.2 12.8 二丙二醇单苯基醚28 85 2 tetrabutylammonium hydroxide 0.2 12.8 dipropylene glycol monophenyl ether
29 85 2 四丁基氢氧化铵 0.2 12.8 二异丙二醇单苯基醚29 85 2 tetrabutylammonium hydroxide 0.2 12.8 diisopropyl glycol monophenyl ether
30 . 85 2 四丁基氢氧化铵 0.2 12.8 乙二醇单苄基醚30 . 85 2 Tetrabutylammonium hydroxide 0.2 12.8 Ethylene glycol monobenzyl ether
31 85 2 四丁基氢氧化铵 0.2 12.8 丙二醇单苄基醚31 85 2 tetrabutylammonium hydroxide 0.2 12.8 propylene glycol monobenzyl ether
32 85 2 四丁基氢氧化铵 0.2 12.8 异丙二醇单苄基醚 效果实施例 1 32 85 2 tetrabutylammonium hydroxide 0.2 12.8 isopropyl glycol monobenzyl ether Effect example 1
表 2 对比清洗剂 1-8和清洗剂 1^5所含组分及其含量  Table 2 Comparison of cleaning agent 1-8 and cleaning agent 1^5 containing components and their content
Figure imgf000007_0001
Figure imgf000007_0001
将效果实施例 1中对比清洗剂 1~8和清洗剂 1〜5用于清洗空白 Cu晶片， 测定其对于金属 Cu的蚀刻速率。 测试方法和条件： 将空白 Cu晶片浸入清 洗剂，在室温至 85°C下利用恒温振荡器缓慢振荡 10〜30分钟，然后经去离子 水洗涤后用高纯氮气吹干。 若清洗温度高于 45°C， 应先用异丙醇洗涤晶片， 再用去离子水洗涤。 最后利用四极探针仪测定空白 Cu晶片蚀刻前后表面电 阻的变化， 计算所得结果列于表 3。 、 表 3 对比清洗剂 1-8和清洗剂 1-5的溶液状态、 Comparing the cleaning agents 1 to 8 and the cleaning agents 1 to 5 in the effect example 1 for cleaning the blank Cu wafer, The etching rate for the metal Cu was measured. Test Methods and Conditions: A blank Cu wafer was immersed in a cleaning agent, and slowly shaken at room temperature to 85 ° C for 10 to 30 minutes using a constant temperature oscillator, then washed with deionized water and then dried with high purity nitrogen. If the cleaning temperature is above 45 ° C, the wafer should be washed first with isopropyl alcohol and then with deionized water. Finally, the change of surface resistance of the blank Cu wafer before and after etching was measured by a quadrupole probe. The calculated results are shown in Table 3. Table 3 compares the solution status of cleaning agents 1-8 and cleaning agents 1-5,
对空白 Cu晶片的蚀刻速率以及对光刻胶的清洗能力  Etching rate of blank Cu wafer and cleaning ability of photoresist
Figure imgf000008_0001
Figure imgf000008_0001
由表 2、 3可见： 与对比清洗剂 1〜8相比， 清洗剂 1〜5的季铵氢氧化物 的溶解量得到提高； 表现出良好的光刻胶清洗能力； 且对空白金属 Cu晶片 的腐蚀性降低。  It can be seen from Tables 2 and 3 that the dissolution amount of the quaternary ammonium hydroxide of the cleaning agent 1 to 5 is improved as compared with the comparative cleaning agents 1 to 8; exhibiting good photoresist cleaning ability; and the blank metal Cu wafer Corrosion is reduced.
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

权利要求 Rights request
1.一种光刻胶清洗剂，包含二甲基亚砜、 季铵氢氧化物， 其特征在于还 含有表面活性剂： 含羟基聚醚。 A photoresist cleaning agent comprising dimethyl sulfoxide, quaternary ammonium hydroxide, characterized by further comprising a surfactant: a hydroxyl group-containing polyether.
2.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的含羟基聚 醚的含鹭为 0.001〜15wt%。  The photoresist cleaning agent according to claim 1, wherein the hydroxy group-containing ether-containing heron is 0.001 to 15% by weight.
3.根据权利要求 2所述的光刻胶清洗剂， 其特征在于： 所述的含羟基聚 醚的含量为 0.05〜5.0wt%。  The photoresist cleaning agent according to claim 2, wherein the hydroxyl group-containing polyether is contained in an amount of from 0.05 to 5.0% by weight.
4.根据权利要求 1 述的光刻胶清洗剂， 其特征在于： 所述的二甲基亚 砜的含量为 70~99wt%。  The photoresist cleaning agent according to claim 1, wherein the dimethyl sulfoxide is contained in an amount of 70 to 99% by weight.
5.根据权利要求 4所述的光刻胶清洗剂， 其特征在于： 所述的二.甲基亚 砜的含量为 80〜99wt%。  The photoresist cleaning agent according to claim 4, wherein the content of the dimethyl sulfoxide is 80 to 99% by weight.
6.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的季铵氢氧 化物的含量为 0.01〜15wt%。  The photoresist cleaning agent according to claim 1, wherein the quaternary ammonium hydroxide is contained in an amount of 0.01 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： 所述的季铵氢氧 化物的含量为 0.5~10.0wt%。  The photoresist cleaning agent according to claim 6, wherein the quaternary ammonium hydroxide is contained in an amount of from 0.5 to 10.0% 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 1, wherein the quaternary ammonium hydroxide is tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetra Butyl ammonium hydroxide or benzyltrimethylammonium hydroxide.
9.根据权利要求 1所述的光刻胶清洗剂， 其特征在于： 所述的光刻胶清 洗剂还包含极性有机共溶剂、 缓蚀剂和 /或水。  The photoresist cleaning agent according to claim 1, wherein the photoresist cleaning agent further comprises a polar organic co-solvent, a corrosion inhibitor, and/or water.
10. '根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的极性 有机共溶剂的含量为 0〜29.5wt%。  The photoresist cleaning agent according to claim 9, wherein the polar organic co-solvent is contained in an amount of from 0 to 29.5 wt%.
11. 根据权利要求 10所述的光刻胶清洗剂， 其特征在于： 所述的极性 有机共溶剂的含量为 5.0~25wt%。  The photoresist cleaning agent according to claim 10, wherein the polar organic co-solvent is contained in an amount of 5.0 to 25% by weight.
12. 根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的缓蚀 剂的含量为 0〜10wt%。 The photoresist cleaning agent according to claim 9, wherein the corrosion inhibitor is contained in an amount of 0 to 10% by weight.
13. 根据权利要求 12所述的光刻胶清洗剂， 其特征在于： 所述的缓蚀 剂的含量为 0.05〜5.0wt%。 The photoresist cleaning agent according to claim 12, wherein the corrosion inhibitor is contained in an amount of from 0.05 to 5.0% by weight.
14. 根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的水的 含量为 0〜29.5wt%。  The photoresist cleaning agent according to claim 9, wherein the water content is 0 to 29.5 wt%.
15. 根据权利要求 14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 14, wherein the water content is 0,5 to 25 wt%.
16. 根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的极性 有机共溶剂为亚 *、砜、咪唑垸酮、烷基二醇单垸基醚和 /或垸基二醇芳基醚。  The photoresist cleaning agent according to claim 9, wherein the polar organic co-solvent is a sub*, a sulfone, an imidazolium, an alkyl glycol monodecyl ether, and/or a mercapto group. Glycol aryl ether.
17. 根据权利要求 16所述的光刻胶清洗剂， 其特征在于： 所述的亚砜 为二乙基亚砜或甲乙基亚砜。  The photoresist cleaning agent according to claim 16, wherein the sulfoxide is diethyl sulfoxide or methyl ethyl sulfoxide.
18. 根据权利要求 16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 16, wherein the sulfone is methyl sulfone, ethyl sulfone or sulfolane. '
19. 根据权利要求 16所述的光刻胶清洗剂， 其特征在于： 所述的咪唑 烷酮为 2-咪唑垸酮、 1,3-二甲基 -2-咪 烷酮或 1，3-二乙基 -2-咪唑嫁酮。 The photoresist cleaning agent according to claim 16, wherein the imidazolidinone is 2-imidazolium, 1,3-dimethyl-2-imidone or 1,3- Diethyl-2-imidazole ketone.
20. 根据权利要求 16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 16, wherein the alkyl glycol 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 monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether or two Propylene glycol monobutyl ether.
21. 根据权利要求 16所述的光刻胶清洗剂， 其特征在于： 所述的烷基. 二醇芳基醚包括乙二醇单苯基醚、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 基醚。  The photoresist cleaning agent according to claim 16, wherein the alkyl diol aryl ether comprises ethylene glycol monophenyl ether, propylene glycol monophenyl ether, and isopropyl glycol monophenyl. Ether, diethylene glycol monophenyl ether, dipropylene glycol monophenyl ether, diisopropyl glycol monophenyl ether, ethylene glycol monobenzyl ether, propylene glycol monobenzyl ether or isopropyl glycol monoether ether.
22. 根据权利要求 9所述的光刻胶清洗剂， 其特征在于： 所述的缓蚀 剂选自酚类、 羧酸（酯）类、 酸酑类或膦酸 （酯）类缓蚀剂。  The photoresist cleaning agent according to claim 9, wherein the corrosion inhibitor is selected from the group consisting of phenols, carboxylic acid esters, acid hydrazines, or phosphonic acid ester corrosion inhibitors. .
23. 根据权利要求 22所述的光刻胶清洗剂， 其特征在于： 所述的酚类 为 1,2-二羟棊苯酚、 对羟基苯酚或连苯三酚。  The photoresist cleaning agent according to claim 22, wherein the phenol is 1,2-dihydroxyindole phenol, p-hydroxyphenol or pyrogallol.
24. 根据权利要求 22所述的光刻胶清洗剂， 其特征在于； 所述的羧酸 (酯）类为苯甲酸、对氨基苯甲酸、邻苯二甲酸、没食子酸或没食子酸丙酯。The photoresist cleaning agent according to claim 22, wherein: the carboxylic acid The (ester) class is benzoic acid, p-aminobenzoic acid, phthalic acid, gallic acid or propyl gallate.
25. 根据权利要求 22所述的光刻胶清洗剂， 其特征在于： 所述的酸酐 类为乙酸酐、 丙酸酐、 己酸酐或（聚） 马来酸酐。 The photoresist cleaning agent according to claim 22, wherein the acid anhydride is acetic anhydride, propionic anhydride, hexanoic anhydride or (poly)maleic anhydride.
26. 根据权利要求 22所述的光刻胶清洗剂， 其特征在于： 所述的膦酸 (酯）类为 1,3- (羟乙基） -2,4,6-三膦酸、 氨基三亚甲基膦酸或 2-膦酸丁烷 The photoresist cleaning agent according to claim 22, wherein the phosphonic acid is 1,3-(hydroxyethyl)-2,4,6-triphosphonic acid or an amino group. Trimethylene phosphonic acid or 2-phosphonic acid butane
-1,2,4-三羧酸。 -1,2,4-tricarboxylic acid.
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US9033928B2 (en) 2008-03-03 2015-05-19 Covidien Lp Single port device with multi-lumen cap
US9549759B2 (en) 2008-03-03 2017-01-24 Covidien Lp Single port device with multi-lumen cap

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