JP2004264401A - Resist stripper - Google Patents

Resist stripper Download PDF

Info

Publication number
JP2004264401A
JP2004264401A JP2003052819A JP2003052819A JP2004264401A JP 2004264401 A JP2004264401 A JP 2004264401A JP 2003052819 A JP2003052819 A JP 2003052819A JP 2003052819 A JP2003052819 A JP 2003052819A JP 2004264401 A JP2004264401 A JP 2004264401A
Authority
JP
Japan
Prior art keywords
water
soluble organic
organic solvent
general formula
resist stripping
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
JP2003052819A
Other languages
Japanese (ja)
Other versions
JP4265741B2 (en
Inventor
Kazumi Chiba
一美 千葉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Japan Carlit Co Ltd
Original Assignee
Japan Carlit 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 Japan Carlit Co Ltd filed Critical Japan Carlit Co Ltd
Priority to JP2003052819A priority Critical patent/JP4265741B2/en
Publication of JP2004264401A publication Critical patent/JP2004264401A/en
Application granted granted Critical
Publication of JP4265741B2 publication Critical patent/JP4265741B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Abstract

<P>PROBLEM TO BE SOLVED: To provide a resist stripper having high resist stripping capability and no corroding property on copper wiring. <P>SOLUTION: The resist stripper is prepared by dissolving an alicyclic ammonium hydroxide expressed by general formula [1] and/or general formula [2] in a water-soluble organic solvent comprising alcohols, glycols, ethers, sulfoxides or amides or in a solvent consisting of the above water-soluble organic solvent and water. In formula [1], X represents a 1 to 4C alkyl group, k represents 0 or a positive integer of 1 to 4, n represents a positive integer of 3 to 7, and R<SB>1</SB>and R<SB>2</SB>represent 1 to 8C alkyl groups. In formula [2], X and Y represent 1 to 4C alkyl groups, k and i represent 0 or positive integers of 1 to 4, and n and m represent positive integers of 3 to 7. <P>COPYRIGHT: (C)2004,JPO&NCIPI

Description

【0001】
【発明の属する技術分野】
本発明は、半導体集積回路、プリント配線基板等の半導体デバイス、あるいは、液晶製造工程等におけるフォトレジスト層を剥離するためのレジスト剥離剤に関する。
【0002】
【従来の技術】
従来、一般にアルミ配線用レジストを剥離する際には、直鎖アルキルアンモニウムヒドロキシド系化合物を主剤とするレジスト剥離剤が用いられてきた。
【0003】
近年では、アルミ配線より導電性の優れた銅配線が用いられるようになってきているが、上記レジスト剥離剤を銅配線用に用いた場合、主剤である直鎖アルキルアンモニウムヒドロキシド系化合物が著しく銅を腐食することから、銅配線プロセスへの適用は困難であった。
【0004】
上記の課題を解決するために、特許文献1では、分子中にヒドロキシル基を含まないカルボキシル基含有有機化合物を添加させた含窒素有機ヒドロキシ系化合物を主剤とするレジスト剥離剤が開示されている。
【0005】
しかしながら、特許文献1に記載のレジスト剥離剤は、レジスト剥離能はあるものの、銅配線への腐食が認められ、腐食防止効果が不十分であり、改善すべき点が残されていた。
【0006】
【特許文献1】特開平7−219240号公報
【0007】
【発明が解決しようとする課題】
本発明の目的は、上記の課題に鑑み、レジスト剥離能が高くかつ銅配線への腐食性のないレジスト剥離剤を提供することにある。
【0008】
【課題を解決するための手段】
本発明者らは、鋭意検討を重ねた結果、脂環式アンモニウムヒドロキシドを含有させた剥離剤が、銅を腐食させることなくレジストを効果的に剥離できることを見いだし、本発明を完成するに至った。
【0009】
すなわち、本発明は、下記一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシドが含有されてなることを特徴とするレジスト剥離剤である。
【0010】
【化3】

Figure 2004264401
【0011】
式中、Xは、炭素数1〜4のアルキル基を、kは、0または1〜4の正整数を、nは、3〜7の正整数を、R及びRは、炭素数1〜8のアルキル基を表す。
【0012】
【化4】
Figure 2004264401
【0013】
式中、X及びYは、炭素数1〜4のアルキル基を、k及びiは、0または1〜4の正整数を、n及びmは3〜7の正整数を表す。
【0014】
また、本発明は、一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシドが、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒中に含有されてなることを特徴とするレジスト剥離剤である。
【0015】
以下、本発明のレジスト剥離剤について詳細に説明する。
【0016】
一般式〔1〕において、Xは、炭素数1〜4のアルキル基を、kは、0または1〜4の正整数を、nは、3〜7の正整数を、R及びRは、炭素数1〜8のアルキル基を表し、Xの炭素数が5以上、nが8以上、または、R及びRの炭素数が9以上の場合には、銅に対する腐食性は小さいものの、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒に対する溶解度が低下してしまい、レジスト剥離能が低下し、不都合である。
【0017】
また、一般式〔2〕において、X及びYは、炭素数1〜4のアルキル基を、k及びiは、0または1〜4の正整数を、n及びmは、3〜7の正整数を表し、X及びYの炭素数が5以上、k及びiが5以上、または、n及びmが8以上の場合には、銅に対する腐食性は小さいものの、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒に対する溶解度が低下してしまい、レジスト剥離能が低下し、不都合である。
【0018】
一般式〔1〕及び一般式〔2〕で表される脂環式アンモニウムヒドロキシドのカチオンとしては、例えば、N,N−ジメチルピロリジニウムイオン、N,N−ジエチルピロリジニウムイオン、N,N−ジ−n−プロピルピロリジニウムイオン、N,N−ジ−n−ブチルピロリジニウムイオン、N,N−ジメチルピペリジニウムイオン、N,N−ジエチルピぺリジニウムイオン、N,N−ジ−n−プロピルピぺリジニウムイオン、N,N−ジ−n−ブチルピぺリジニウムイオン、スピロ−(1,1’)−ビアザシクロブチルイオン、アザシクロペンタン−1−スピロ−1’−アザシクロブチルイオン、アザシクロヘキサン−1−スピロ−1’−アザシクロブチルイオン、アザシクロヘプタン−1−スピロ−1’− アザシクロブチルイオン、アザシクロオクタン−1−スピロ−1’− アザシクロブチルイオン、スピロ−(1,1’)−ビアザシクロペンチルイオン、アザシクロヘキサン−1−スピロ−1’−アザシクロペンチルイオン、アザシクロヘプタン−1−スピロ−1’−アザシクロペンチルイオン、アザシクロオクタン−1−スピロ−1’−アザシクロペンチルイオン、スピロ−(1,1’)−ビアザシクロヘキシルイオン、アザシクロヘプタン−1−スピロ−1’−アザシクロヘキシルイオン、アザシクロオクタン−1−スピロ−1’−アザシクロヘキシルイオン、スピロ−(1,1’)−ビアザシクロヘプチルイオン、アザシクロオクタン−1−スピロ−1’−アザシクロヘプチルイオン、スピロ−(1,1’)−ビアザシクロオクチルイオンがあげられる。
【0019】
一般式〔1〕及び一般式〔2〕で表される脂環式アンモニウムヒドロキシドは、まずイソプロピルアルコール溶媒中、炭酸カリウム存在下でアザシクロアルカンに末端を臭素化させたブロモアルカンまたは両末端を臭素化させたジブロモアルカンを作用させて脂環式アンモニウムブロマイドを得、次に該ブロマイドを水またはアルコール中で電気透析により脱塩させて製造することができる。
【0020】
本発明のレジスト剥離剤は、少なくとも1種の脂環式アンモニウムヒドロキシドを水に溶解させるか、水溶性有機溶媒あるいは水溶性有機溶媒及び水に溶解させて用いられる。レジスト剥離能を向上させるため、通常、水溶性有機溶媒あるいは水溶性有機溶媒及び水に溶解させて用いられる。
【0021】
水溶性有機溶媒としては、アルコール類、グリコール類、エーテル類、スルホキシド類、アミド類からなる群より選ばれる少なくとも1種が用いられ、例えば、メタノール、エタノール、n−プロパノール、i−プロパノール、ブタノール等のアルコール類、エチレングリコール、プロピレングリコール、ポリエチレングリコール等のグリコール類、テトラヒドロフラン、ジオキサン等のエーテル類、ジメチルスルホキシド等のスルホキシド類、N−メチル−2−ピロリドン等のアミド類があげられる。
【0022】
本発明のレジスト剥離剤は、必要に応じて、公知の防食剤、界面活性剤が添加される。
【0023】
本発明のレジスト剥離剤は、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒100質量部当たり、一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシドを、少なくとも1種の合計量が0.1〜20質量部の範囲で含有される。
【0024】
脂環式アンモニウムヒドロキシドの量が0.1質量部より未満の場合、レジスト剥離能が不十分であり、20質量部より超の場合、レジスト剥離能は十分であるが銅配線が腐食され、不都合である。
【0025】
本発明のレジスト剥離剤は、使用時に各成分を混合させるか、あるいは、各成分を予め混合させたものが用いられる。
【0026】
本発明のレジスト剥離剤を用いるに際し、加熱、超音波等を併用させた場合、レジスト剥離能を高めることができ、より好ましい。
【0027】
また、本発明のレジスト剥離剤で洗浄する方法としては、浸漬法や、ブラシ洗浄法等があげられる。
【0028】
本発明のレジスト剥離剤は、レジスト剥離能が高くかつ銅への腐食性がないので、銅配線プロセスへ適用することができる。
【0029】
また、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒中に、一般式〔1〕及び/または一般式〔2〕で表される、脂環式アンモニウムヒドロキシドを溶解させた場合、優れた粒子除去性を有するため、半導体デバイスの洗浄に対しても、極めて有効である。
【0030】
【発明の実施の形態】
以下、本発明の実施の形態を、実施例に基づいて説明する。なお、本発明は実施例により、なんら限定されない。なお、実施例中の「部」は「質量部」を表す。
【0031】
実施例1
脂環式アンモニウムヒドロキシドであるスピロ−(1,1’)−ビアザシクロペンチルヒドロキシド(「SBPH」と略記する。)3質量部と、水溶性有機溶媒であるイソプロピルアルコール(「IPA」と略記する。)97質量部とを混合させて、レジスト剥離剤を得た。
【0032】
得られたレジスト剥離剤を以下に示す方法により評価した。
【0033】
銅メッキしたシリコンウェハを、まず平均粒子径1μmのアルミナ粒子を分散させた超純水中に浸漬させ、次に硫酸を用いてpH6に調整した超純水に浸漬させた。ついで、該ウェハを乾燥させて、表面がアルミナ粒子により強制汚染されたウェハを得、ついで、上記剥離剤中に、該ウェハを温度30℃、15分間浸漬させて洗浄した後、水洗、乾燥させた。
【0034】
次に、ウェハ表面を走査型電子顕微鏡で観察し、粒子除去性をアルミナ粒子の残存度により、また銅への腐食性を表面の凹凸により評価した。結果を表1に示す。
【0035】
実施例2
実施例1に準じて、表1に記載の成分を用いてレジスト剥離剤を得、実施例1に準じて、粒子除去性及び銅腐食性を評価した。結果を表1に示す。
【0036】
【表1】
Figure 2004264401
【0037】
表1記載の成分は、レジスト剥離剤である、スピロ−(1,1’)−ビアザシクロペンチルヒドロキシド(SBPH)、ジエチルピロリジニウムヒドロキシド(DEPH)、テトラメチルアンモニウムヒドロキシド(TMAH)、テトラエチルアンモニウムヒドロキシド(TEAH)を、また、水溶性有機溶媒である、i−プロパノール(IPA)、ジメチルスルホキシド(DMSO)を表す。
【0038】
式1中、粒子除去性は、「良好」を「○」、「残存物あり」を「×」で表し、銅腐食性は、「腐食なし」を「○」、「一部腐食あり」を「△」、「腐食あり」を「×」で表した。
【0039】
表1からわかるように、直鎖アルキルアンモニウムヒドロキシドを含有した従来のレジスト剥離剤(比較例1及び2)は、粒子除去性は良好であるが、銅腐食性を有しているのに対し、脂環式アンモニウムヒドロキシドを含有した本発明のレジスト剥離剤(実施例1及び2)は粒子除去性が良好でありかつ銅腐食性がなく、銅配線用のレジスト剥離剤として有効である。
【0040】
【発明の効果】
本発明のレジスト剥離剤は、レジスト剥離能が高くかつ銅への腐食性がないので、銅配線プロセスへ適用することができる。
【0041】
また、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒中に、一般式〔1〕及び/または一般式〔2〕で表される、脂環式アンモニウムヒドロキシドを溶解させた場合、優れた粒子除去性を有し、半導体デバイスの洗浄に対しても極めて有効である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a semiconductor device such as a semiconductor integrated circuit and a printed wiring board, or a resist stripping agent for stripping a photoresist layer in a liquid crystal manufacturing process or the like.
[0002]
[Prior art]
Conventionally, a resist stripping agent mainly containing a straight-chain alkylammonium hydroxide-based compound has been generally used for stripping a resist for aluminum wiring.
[0003]
In recent years, copper wiring having better conductivity than aluminum wiring has come to be used, but when the above-mentioned resist stripping agent is used for copper wiring, a straight-chain alkylammonium hydroxide-based compound as a main component is remarkably used. Since it corrodes copper, it has been difficult to apply it to a copper wiring process.
[0004]
In order to solve the above problem, Patent Literature 1 discloses a resist stripping agent mainly containing a nitrogen-containing organic hydroxy compound to which a carboxyl group-containing organic compound not containing a hydroxyl group in a molecule is added.
[0005]
However, although the resist stripping agent described in Patent Document 1 has a resist stripping ability, corrosion to copper wiring was observed, the effect of preventing corrosion was insufficient, and there were still points to be improved.
[0006]
[Patent Document 1] Japanese Patent Application Laid-Open No. 7-219240
[Problems to be solved by the invention]
An object of the present invention is to provide a resist stripping agent which has high resist stripping ability and has no corrosiveness to copper wiring in view of the above problems.
[0008]
[Means for Solving the Problems]
The present inventors have conducted intensive studies and as a result, have found that a stripping agent containing an alicyclic ammonium hydroxide can effectively strip a resist without corroding copper, and have completed the present invention. Was.
[0009]
That is, the present invention is a resist stripping agent comprising an alicyclic ammonium hydroxide represented by the following general formula [1] and / or general formula [2].
[0010]
Embedded image
Figure 2004264401
[0011]
In the formula, X is an alkyl group having 1 to 4 carbon atoms, k is a positive integer of 0 or 1 to 4, n is a positive integer of 3 to 7, R 1 and R 2 are 1 to 4 carbon atoms. To 8 alkyl groups.
[0012]
Embedded image
Figure 2004264401
[0013]
In the formula, X and Y each represent an alkyl group having 1 to 4 carbon atoms, k and i each represent a positive integer of 0 or 1 to 4, and n and m each represent a positive integer of 3 to 7.
[0014]
Further, the present invention provides a method wherein the alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] is contained in a water-soluble organic solvent or a solvent comprising a water-soluble organic solvent and water. A resist stripping agent.
[0015]
Hereinafter, the resist stripping agent of the present invention will be described in detail.
[0016]
In the general formula [1], X is an alkyl group having 1 to 4 carbon atoms, k is a positive integer of 0 or 1 to 4, n is a positive integer of 3 to 7, R 1 and R 2 are , Represents an alkyl group having 1 to 8 carbon atoms, and when X has 5 or more carbon atoms, n has 8 or more carbon atoms, or R 1 and R 2 have 9 or more carbon atoms, the corrosiveness to copper is small, In addition, the solubility in a water-soluble organic solvent or a solvent composed of a water-soluble organic solvent and water is reduced, and the resist stripping ability is disadvantageously reduced.
[0017]
In the general formula [2], X and Y are an alkyl group having 1 to 4 carbon atoms, k and i are 0 or 1 to 4 positive integers, and n and m are 3 to 7 positive integers. When X and Y each have 5 or more carbon atoms, k and i are 5 or more, or n and m are 8 or more, the corrosiveness to copper is small, but the water-soluble organic solvent or the water-soluble organic solvent is used. In addition, the solubility in a solvent consisting of water and water decreases, and the resist stripping ability decreases, which is inconvenient.
[0018]
Examples of the cations of the alicyclic ammonium hydroxide represented by the general formulas [1] and [2] include N, N-dimethylpyrrolidinium ion, N, N-diethylpyrrolidinium ion, N, N- Di-n-propylpyrrolidinium ion, N, N-di-n-butylpyrrolidinium ion, N, N-dimethylpiperidinium ion, N, N-diethylpyridinium ion, N, N-di-n-propylpyridinium ion Lydinium ion, N, N-di-n-butylpiridinium ion, spiro- (1,1 ′)-biazacyclobutyl ion, azacyclopentane-1-spiro-1′-azacyclobutyl ion, azacyclohexane- 1-spiro-1′-azacyclobutyl ion, azacycloheptane-1-spiro-1′-azacyclobutyl ion, azashik Octane-1-spiro-1′-azacyclobutyl ion, spiro- (1,1 ′)-biazacyclopentyl ion, azacyclohexane-1-spiro-1′-azacyclopentyl ion, azacycloheptane-1-spiro- 1'-azacyclopentyl ion, azacyclooctane-1-spiro-1'-azacyclopentyl ion, spiro- (1,1 ')-biazacyclohexyl ion, azacycloheptane-1-spiro-1'-azacyclohexyl ion Azacyclooctane-1-spiro-1′-azacyclohexyl ion, spiro- (1,1 ′)-biazacycloheptyl ion, azacyclooctane-1-spiro-1′-azacycloheptyl ion, spiro- ( 1,1 ′)-Biazacyclooctyl ion.
[0019]
The alicyclic ammonium hydroxide represented by the general formula [1] and the general formula [2] is a bromoalkane obtained by brominating an azacycloalkane at the terminal or both ends in an isopropyl alcohol solvent in the presence of potassium carbonate. The alicyclic ammonium bromide can be obtained by the action of a brominated dibromoalkane, and the bromide can then be desalted by electrodialysis in water or alcohol.
[0020]
The resist stripping agent of the present invention is used by dissolving at least one alicyclic ammonium hydroxide in water, or in a water-soluble organic solvent or a water-soluble organic solvent and water. In order to improve the resist stripping ability, it is usually used after being dissolved in a water-soluble organic solvent or a water-soluble organic solvent and water.
[0021]
As the water-soluble organic solvent, at least one selected from the group consisting of alcohols, glycols, ethers, sulfoxides, and amides is used. For example, methanol, ethanol, n-propanol, i-propanol, butanol and the like are used. Alcohols, glycols such as ethylene glycol, propylene glycol and polyethylene glycol, ethers such as tetrahydrofuran and dioxane, sulfoxides such as dimethyl sulfoxide, and amides such as N-methyl-2-pyrrolidone.
[0022]
The resist remover of the present invention may contain known anticorrosives and surfactants as necessary.
[0023]
The alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] per 100 parts by mass of a water-soluble organic solvent or a solvent composed of a water-soluble organic solvent and water is used for the resist stripping agent of the present invention. At least one kind is contained in the range of 0.1 to 20 parts by mass.
[0024]
When the amount of the alicyclic ammonium hydroxide is less than 0.1 part by mass, the resist stripping ability is insufficient, and when the amount is more than 20 parts by mass, the resist stripping ability is sufficient but the copper wiring is corroded, It is inconvenient.
[0025]
The resist stripping agent of the present invention is prepared by mixing the components at the time of use or by mixing the components in advance.
[0026]
When using the resist stripping agent of the present invention together with heating, ultrasonic waves, etc., the resist stripping ability can be enhanced, which is more preferable.
[0027]
Examples of the method for cleaning with the resist stripping agent of the present invention include an immersion method and a brush cleaning method.
[0028]
Since the resist stripping agent of the present invention has a high resist stripping ability and has no corrosiveness to copper, it can be applied to a copper wiring process.
[0029]
Also, when an alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] is dissolved in a water-soluble organic solvent or a solvent composed of a water-soluble organic solvent and water, Since it has excellent particle removal properties, it is extremely effective for cleaning semiconductor devices.
[0030]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, embodiments of the present invention will be described based on examples. In addition, this invention is not limited at all by an Example. In the examples, “parts” represents “parts by mass”.
[0031]
Example 1
Spiro- (1,1 ′)-biazacyclopentyl hydroxide (abbreviated as “SBPH”) which is an alicyclic ammonium hydroxide, 3 parts by mass, and isopropyl alcohol (abbreviated as “IPA”) which is a water-soluble organic solvent ) And 97 parts by mass to obtain a resist stripping agent.
[0032]
The obtained resist remover was evaluated by the following method.
[0033]
The copper-plated silicon wafer was first immersed in ultrapure water in which alumina particles having an average particle diameter of 1 μm were dispersed, and then immersed in ultrapure water adjusted to pH 6 using sulfuric acid. Next, the wafer is dried to obtain a wafer whose surface is forcibly contaminated with alumina particles. Then, the wafer is immersed in the release agent at a temperature of 30 ° C. for 15 minutes, washed, washed with water, and dried. Was.
[0034]
Next, the wafer surface was observed with a scanning electron microscope, and the particle removability was evaluated by the residual degree of the alumina particles, and the corrosiveness to copper was evaluated by the surface irregularities. Table 1 shows the results.
[0035]
Example 2
A resist stripping agent was obtained using the components shown in Table 1 according to Example 1, and the particle removal property and the copper corrosion property were evaluated according to Example 1. Table 1 shows the results.
[0036]
[Table 1]
Figure 2004264401
[0037]
The components listed in Table 1 are resist strippers, spiro- (1,1 ′)-biazacyclopentyl hydroxide (SBPH), diethylpyrrolidinium hydroxide (DEPH), tetramethylammonium hydroxide (TMAH), Tetraethylammonium hydroxide (TEAH) and i-propanol (IPA) and dimethylsulfoxide (DMSO), which are water-soluble organic solvents.
[0038]
In the formula 1, the particle removability is represented by “良好” for “good”, and “x” for “residual”, and the copper corrosivity is represented by “「 ”for“ no corrosion ”and“ partially corroded ”. "△" and "corrosion" were represented by "x".
[0039]
As can be seen from Table 1, the conventional resist removers containing linear alkyl ammonium hydroxides (Comparative Examples 1 and 2) have good particle removal properties but have copper corrosiveness. The alicyclic ammonium hydroxide-containing resist stripping agent of the present invention (Examples 1 and 2) has good particle removability, has no copper corrosiveness, and is effective as a resist stripping agent for copper wiring.
[0040]
【The invention's effect】
Since the resist stripping agent of the present invention has a high resist stripping ability and has no corrosiveness to copper, it can be applied to a copper wiring process.
[0041]
Also, when an alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] is dissolved in a water-soluble organic solvent or a solvent composed of a water-soluble organic solvent and water, It has excellent particle removal properties and is extremely effective for cleaning semiconductor devices.

Claims (4)

一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシドが含有されてなることを特徴とするレジスト剥離剤。
Figure 2004264401
(式中、Xは、炭素数1〜4のアルキル基を、kは0または1〜4の正整数を、nは、3〜7の正整数を、R及びRは、炭素数1〜8のアルキル基を表す。)
Figure 2004264401
(式中、X及びYは、炭素数1〜4のアルキル基を、k及びiは、0または1〜4の正整数を、n及びmは、3〜7の正整数を表す。)
A resist remover comprising an alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2].
Figure 2004264401
(In the formula, X is an alkyl group having 1 to 4 carbon atoms, k is a positive integer of 0 or 1 to 4, n is a positive integer of 3 to 7, R 1 and R 2 are 1 to 4 carbon atoms. ~ 8 alkyl groups.)
Figure 2004264401
(In the formula, X and Y represent an alkyl group having 1 to 4 carbon atoms, k and i represent 0 or a positive integer of 1 to 4, and n and m represent a positive integer of 3 to 7.)
請求項1に記載の一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシドが、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒中に含有されてなることを特徴とする請求項1に記載のレジスト剥離剤。The alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] according to claim 1 is contained in a water-soluble organic solvent or a solvent comprising a water-soluble organic solvent and water. The resist stripping agent according to claim 1, wherein: 水溶性有機溶媒が、アルコール類、グリコール類、エーテル類、スルホキシド類、アミド類からなる群より選ばれる少なくとも1種であることを特徴とする請求項2に記載のレジスト剥離剤。The resist stripping agent according to claim 2, wherein the water-soluble organic solvent is at least one selected from the group consisting of alcohols, glycols, ethers, sulfoxides, and amides. 一般式〔1〕及び/または一般式〔2〕で表される脂環式アンモニウムヒドロキシド0.1〜20質量部が、水溶性有機溶媒あるいは水溶性有機溶媒及び水からなる溶媒100質量部に溶解されてなる請求項2または請求項3に記載のレジスト剥離剤。0.1 to 20 parts by mass of the alicyclic ammonium hydroxide represented by the general formula [1] and / or the general formula [2] is added to 100 parts by mass of a water-soluble organic solvent or a solvent composed of a water-soluble organic solvent and water. The resist stripping agent according to claim 2 or 3, which is dissolved.
JP2003052819A 2003-02-28 2003-02-28 Resist stripper Expired - Fee Related JP4265741B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2003052819A JP4265741B2 (en) 2003-02-28 2003-02-28 Resist stripper

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2003052819A JP4265741B2 (en) 2003-02-28 2003-02-28 Resist stripper

Publications (2)

Publication Number Publication Date
JP2004264401A true JP2004264401A (en) 2004-09-24
JP4265741B2 JP4265741B2 (en) 2009-05-20

Family

ID=33117594

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2003052819A Expired - Fee Related JP4265741B2 (en) 2003-02-28 2003-02-28 Resist stripper

Country Status (1)

Country Link
JP (1) JP4265741B2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006317714A (en) * 2005-05-12 2006-11-24 Tokyo Ohka Kogyo Co Ltd Stripper for photoresist
WO2014013396A2 (en) * 2012-07-16 2014-01-23 Basf Se Composition for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006317714A (en) * 2005-05-12 2006-11-24 Tokyo Ohka Kogyo Co Ltd Stripper for photoresist
JP4678673B2 (en) * 2005-05-12 2011-04-27 東京応化工業株式会社 Photoresist stripping solution
US8114825B2 (en) 2005-05-12 2012-02-14 Tokyo Ohka Kogyo Co., Ltd. Photoresist stripping solution
WO2014013396A2 (en) * 2012-07-16 2014-01-23 Basf Se Composition for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices
WO2014013396A3 (en) * 2012-07-16 2014-03-06 Basf Se Composition for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices
CN104471487A (en) * 2012-07-16 2015-03-25 巴斯夫欧洲公司 Composition for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices
EP2875406A4 (en) * 2012-07-16 2016-11-09 Basf Se Composition for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices

Also Published As

Publication number Publication date
JP4265741B2 (en) 2009-05-20

Similar Documents

Publication Publication Date Title
US6777380B2 (en) Compositions for cleaning organic and plasma etched residues for semiconductor devices
US20050003977A1 (en) Composition for cleaning
US7456140B2 (en) Compositions for cleaning organic and plasma etched residues for semiconductor devices
JP4304988B2 (en) Semiconductor device substrate cleaning method
US20080096785A1 (en) Stripper Containing an Acetal or Ketal for Removing Post-Etched Photo-Resist, Etch Polymer and Residue
WO2003083582A1 (en) Ph buffered compositions for cleaning semiconductor substrates
CN1776532A (en) Composition for removal of residual material from substrate and method using the composition
EP1610185A2 (en) Composition and method using same for removing residue from a substrate
JP2009075285A (en) Stripper for semiconductor device and stripping method
JP2009102729A (en) Aqueous stripping and cleaning composition
JP2005043873A (en) Photoresist stripping liquid composition and method for stripping photoresist by using the same
TWI359866B (en) Cleaning composition and method
JP2004307725A (en) Semiconductor-substrate washing liquid composition
JP4902898B2 (en) Stabilized non-aqueous cleaning composition for microelectronic substrates
JP4215537B2 (en) Resist stripper
JP4667147B2 (en) Substrate cleaning solution
JP2004277576A (en) Method for preparing solution for etching or cleaning
JP4265741B2 (en) Resist stripper
KR101799592B1 (en) A Detergent Composition For A Substrate Of Flat Panel Display Device And Cleaning Method Using The Same
JP4165209B2 (en) Resist stripper
CN1507581A (en) Resist remover composition
JP2005037631A (en) Resist stripper
JP5206177B2 (en) Resist stripping composition and method for manufacturing semiconductor device using the same
JP2007311729A (en) Substrate cleaning solution
JPH11251214A (en) Manufacture of tantalum thin-film circuit element

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20060207

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20081030

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20081104

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20081212

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20090113

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20090119

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20090210

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20090210

R150 Certificate of patent or registration of utility model

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20120227

Year of fee payment: 3

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20150227

Year of fee payment: 6

S531 Written request for registration of change of domicile

Free format text: JAPANESE INTERMEDIATE CODE: R313531

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313111

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

LAPS Cancellation because of no payment of annual fees