JP2759462B2 - Aqueous release agent composition - Google Patents
Aqueous release agent compositionInfo
- Publication number
- JP2759462B2 JP2759462B2 JP63286261A JP28626188A JP2759462B2 JP 2759462 B2 JP2759462 B2 JP 2759462B2 JP 63286261 A JP63286261 A JP 63286261A JP 28626188 A JP28626188 A JP 28626188A JP 2759462 B2 JP2759462 B2 JP 2759462B2
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- weight
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は、半導体や集積回路等の製造において、無機
質又は有機質の基体に塗布されたポジ型フオトレジスト
を基体から剥離するための水性の剥離剤組成物に関す
る。Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aqueous release agent composition for releasing a positive photoresist applied to an inorganic or organic substrate from a substrate in the production of semiconductors and integrated circuits. About things.
従来の技術 半導体や集積回路は、無機質基体上にフオトレジスト
を塗布し、これを露光させ、現像し、ベークし、次い
で、これにエツチングや選択的拡散等の所要の微細加工
を施して、パターニングを行なつた後、上記フオトレジ
スト膜を基体から剥離除去することによつて製造されて
いる。また、液晶の製造には、ポリイミド等の有機質基
体も用いられている。2. Description of the Related Art In semiconductors and integrated circuits, a photoresist is coated on an inorganic substrate, exposed, developed, baked, and then subjected to required fine processing such as etching and selective diffusion to be patterned. And then removing the photoresist film from the substrate. Organic substrates such as polyimide are also used in the production of liquid crystals.
一般に、フオトレジストには、露光によつて可溶化す
るポジ型と、露光によつて不溶化するネガ型とがあり、
ポジ型としては、例えば、代表的にはフエノール・ホル
ムアルデヒド樹脂と光増感剤とからなるフオトレジスト
が知られており、ネガ型としては、樹脂成分としてポリ
ケイ皮酸ビニルや環化ゴムを含有するフオトレジストが
知られている。In general, photoresists include a positive type which is solubilized by exposure and a negative type which is insolubilized by exposure.
As the positive type, for example, a photoresist composed of a phenol / formaldehyde resin and a photosensitizer is typically known, and the negative type contains polyvinyl cinnamate or a cyclized rubber as a resin component. Photoresists are known.
このようにポジ型及びネガ型に応じて、基体上にフオ
トレジスト膜を形成し、微細加工を施した後にこのフオ
トレジスト膜を剥離除去するための剥離剤組成物は、従
来、一般にフエノール又はその誘導体と塩素系有機溶剤
を含有している。このような剥離剤組成物は、フオトレ
ジスト膜の剥離性にすぐれるのみならず、金属からなる
基体に対して実質的に腐食性がないために、従来、広く
使用されている。しかし、かかる剥離剤組成物は、フエ
ノール系化合物や塩素系有機溶剤を含有するために毒性
が指摘されており、また、その廃液処理にも問題を有す
る。As described above, in accordance with the positive type and the negative type, a release agent composition for forming a photoresist film on a substrate and peeling and removing the photoresist film after performing fine processing is conventionally, generally, phenol or a release agent composition thereof. Contains derivatives and chlorinated organic solvents. Such a stripping composition has been widely used, because it has excellent releasability of a photoresist film and is substantially not corrosive to a metal substrate. However, toxicity has been pointed out because such a release agent composition contains a phenolic compound or a chlorine-based organic solvent, and there is also a problem in treating the waste liquid.
発明が解決しようとする問題点 本発明は、従来のポジ型フオトレジストの剥離剤組成
物における上記した問題点を解決するためになされたも
のであつて、フエノール系化合物や塩素系有機溶剤を含
有せず、しかも、水性であつて、作業性及び安全性にす
ぐれ、更に、金属基体のみならず、ポリイミドのような
有機質基体に対しても腐食性を有しないポジ型フオトレ
ジスト膜の水性剥離剤組成物を提供することを目的とす
る。Problems to be Solved by the Invention The present invention has been made in order to solve the above-mentioned problems in the conventional positive type photoresist stripping composition, and contains a phenolic compound and a chlorine-based organic solvent. Aqueous stripping agent for a positive photoresist film which is water-based, excellent in workability and safety, and not corrosive not only to metal substrates but also to organic substrates such as polyimide. It is intended to provide a composition.
問題点を解決するための手段 本発明による基体上に塗布されたポジ型フオトレジス
ト膜を剥離するための水性剥離剤組成物は、 （ａ） N,N−ジメチルホルムアミド及びN,N−ジメチル
アセトアミドよりなる群から選ばれる少なくとも１種の
鎖状アミド５〜30重量％、 及び （ｂ） ジエチレングリコールモノブチルエーテル95〜
70重量％ とからなる混合物100重量部と、 （ｃ） 水 50〜200重量部 とからなることを特徴とする。Means for Solving the Problems An aqueous stripping composition for stripping a positive photoresist film coated on a substrate according to the present invention comprises: (a) N, N-dimethylformamide and N, N-dimethylacetamide At least one linear amide selected from the group consisting of 5 to 30% by weight, and (b) diethylene glycol monobutyl ether 95 to 95% by weight.
(C) 50 to 200 parts by weight of water.
本発明において、基体は、無機質、有機質いずれであ
つてもよく、無機質基体には、例えば、二酸化ケイ素、
サフアイア、ケイ素被膜を有するケイ素、窒化ケイ素、
ガリウム−ヒ素（ヒ化ガリウム）、銅、ガラス、酸化ク
ロム、ニツケル、クロム、アルミニウム、インジウム、
チタン酸化膜等の導電性被膜を有する基板を含む。ま
た、有機質基体の代表例としては、例えば、ポリイミド
基体（ポリイミド樹脂膜）を挙げることができる。In the present invention, the substrate may be inorganic or organic, and the inorganic substrate includes, for example, silicon dioxide,
Sapphire, silicon with silicon coating, silicon nitride,
Gallium-arsenic (gallium arsenide), copper, glass, chromium oxide, nickel, chromium, aluminum, indium,
It includes a substrate having a conductive film such as a titanium oxide film. A typical example of the organic substrate is a polyimide substrate (polyimide resin film).
好ましくは、本発明による剥離剤組成物は、（ａ）上
記鎖状アミド10〜20重量％と（ｂ）ジエチレングリコー
ルモノブチルエーテル90〜80重量％とからなる混合物10
0重量部と、（ｃ）水50〜200重量部とからなることを特
徴とする。更に、本発明による水性剥離剤組成物は、上
記混合物100重量部と水75〜150重量部とからなることが
好ましい。Preferably, the release agent composition according to the present invention comprises a mixture of (a) 10 to 20% by weight of the above chain amide and (b) 90 to 80% by weight of diethylene glycol monobutyl ether.
0 parts by weight and (c) 50 to 200 parts by weight of water. Further, the aqueous release agent composition according to the present invention preferably comprises 100 parts by weight of the above mixture and 75 to 150 parts by weight of water.
上記鎖状アミドのほか、Ｎ−メチル−２−ピロリドン
のような環状アミドとジエチレングリコールモノブチル
エーテルとの本発明で規定する割合の組成物（有機溶剤
型組成物）も、ポジ型フオトレジスト膜のための剥離剤
組成物として有用であるが、本発明に従つて、N,N−ジ
メチルホルムアミド及びN,N−ジメチルアセトアミドよ
りなる群から選ばれる少なくとも１種の鎖状アミドとジ
エチレングリコールモノブチルエーテルとの前記所定の
割合の混合物100重量部に所定の割合の水を配合して、
水性剥離剤組成物とすることによつて、不燃性であつ
て、作業性及び安全性にすぐれるうえ、金属基板のみな
らず、ポリイミド基体のような有機質基体に対しても腐
食性を有しない剥離剤組成物を得ることができる。In addition to the above-mentioned chain amide, a composition (organic solvent type composition) of a cyclic amide such as N-methyl-2-pyrrolidone and diethylene glycol monobutyl ether in the ratio specified in the present invention is also used for a positive photoresist film. According to the present invention, at least one chain amide selected from the group consisting of N, N-dimethylformamide and N, N-dimethylacetamide, and diethylene glycol monobutyl ether. A predetermined ratio of water is blended with 100 parts by weight of the predetermined ratio of the mixture,
By using the aqueous release agent composition, it is nonflammable, excellent in workability and safety, and does not corrode not only on a metal substrate but also on an organic substrate such as a polyimide substrate. A release agent composition can be obtained.
本発明による水性剥離剤組成物は、20〜90℃の範囲の
温度で用いることができるが、常温で用いても、フオト
レジスト膜の剥離性に著しくすぐれる。例えば、剥離す
べきフオトレジスト膜を有する基体を本発明による剥離
剤組成物中に常温にて浸漬した後、水にてリンスし、乾
燥することによつて、フオトレジスト膜が除去された基
体を得ることができる。The aqueous release agent composition according to the present invention can be used at a temperature in the range of 20 to 90 ° C, but even when used at room temperature, the removability of the photoresist film is remarkably excellent. For example, a substrate having a photoresist film to be stripped is immersed in a stripping composition according to the present invention at room temperature, rinsed with water, and dried to remove the substrate from which the photoresist film has been removed. Obtainable.
本発明による剥離剤組成物は、特にポジ型フオトレジ
スト膜の剥離に好適であり、かかるポジ型フオトレジス
トとしては、例えば、重合体成分としてフエノール・ホ
ルムアルデヒド樹脂を含有するフオトレジストを挙げる
ことができる。The stripping composition according to the present invention is particularly suitable for stripping a positive-type photoresist film. Examples of such a positive-type photoresist include a photoresist containing a phenol-formaldehyde resin as a polymer component. .
発明の効果 本発明による水性剥離剤組成物は、以上のように、特
に選択された鎖状アミドとジエチレングリコールモノブ
チルエーテルを所定の割合で含む水性の組成物であつ
て、塩素系溶剤やフエノール類を含む従来の剥離剤組成
物と異なり、毒性が少なく、不燃性であつて、作業性及
び安全性にすぐれるのみならず、金属基板のほか、ポリ
イミド基体のような有機質基体をも腐食しない。As described above, the aqueous release agent composition according to the present invention is an aqueous composition containing a selected chain amide and diethylene glycol monobutyl ether in a predetermined ratio, and contains a chlorine-based solvent and phenols. Unlike conventional release agent compositions, it has low toxicity, is nonflammable, has excellent workability and safety, and does not corrode metal substrates as well as organic substrates such as polyimide substrates.
更に、本発明による水性剥離剤組成物は、フオトレジ
スト膜の剥離処理後のリンス工程において、芳香族炭化
水素やハロゲン系溶剤を用いる必要がなく、水洗によつ
て基体から容易に組成物を除去することができるので、
この点からも、作業性及び安全性にすぐれ、更に、廃液
処理も容易である。Furthermore, the aqueous stripper composition according to the present invention does not require the use of an aromatic hydrocarbon or a halogen-based solvent in the rinsing step after the photoresist film is stripped, and the composition is easily removed from the substrate by washing with water. So you can
From this point, workability and safety are excellent, and waste liquid treatment is also easy.
実施例 以下に実施例を挙げて本発明を説明するが、本発明は
これら実施例により何ら限定されるものではない。EXAMPLES Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.
実施例１ シリコンウエハー上に密着性付与剤を塗布した後、市
販のポジ型フオトレジストをスピンコーターにて厚さ1.
5μｍに塗布し、100℃の温度で２分間ホツトプレート上
でプレベークし、更に、120〜200℃の温度でポストベー
クして、フオトレジスト膜を形成した。Example 1 After coating an adhesion-imparting agent on a silicon wafer, a commercially available positive type photoresist was applied to a thickness of 1.
It was applied to a thickness of 5 μm, pre-baked on a hot plate at a temperature of 100 ° C. for 2 minutes, and further post-baked at a temperature of 120 to 200 ° C. to form a photoresist film.
このフオトレジスト膜を第１表に示す組成を有する剥
離剤組成物中にそれぞれ第１表に示す所定温度にて浸漬
した後、純水で洗浄し、赤外線ランプ下で乾燥した。ウ
エハー表面を単色光下に顕微鏡にて基体上の残存フオト
レジスト膜の有無を観察することにより、フオトレジス
ト膜の剥離速度を求めた。結果を第２表に示す。This photoresist film was immersed in a stripper composition having the composition shown in Table 1 at a predetermined temperature shown in Table 1, washed with pure water, and dried under an infrared lamp. By observing the presence or absence of the remaining photoresist film on the substrate with a microscope under the monochromatic light on the wafer surface, the removal rate of the photoresist film was obtained. The results are shown in Table 2.
第１表において、剥離剤番号１〜４は、N,N−ジメチ
ルホルムアミド又はN,N−ジメチルアセトアミドとジエ
チレングリコールモノブチルエーテルとからなり、参考
例としての有機溶剤型剥離剤組成物を示し、剥離剤番号
５はアミドとしてＮ−メチルピロリドンを用いた比較例
としての有機溶剤型剥離剤組成物を示し、剥離剤番号６
及び７が本発明による水性剥離剤組成物である。In Table 1, release agents Nos. 1 to 4 consist of N, N-dimethylformamide or N, N-dimethylacetamide and diethylene glycol monobutyl ether, and show an organic solvent type release agent composition as a reference example. No. 5 shows an organic solvent type release agent composition as a comparative example using N-methylpyrrolidone as an amide, and release agent No. 6
And 7 are aqueous release agent compositions according to the present invention.
実施例２ 第３表に示す組成を有する剥離剤組成物を含む浴中に
ガラス板上にニツケルを蒸着した基体を60℃にて21時間
浸漬した後、取出した。浴中に溶出したニツケル量を原
子吸光法にて測定し、基体の腐食速度を求めた。結果を
第３表に示す。 Example 2 A substrate on which nickel was deposited on a glass plate was immersed in a bath containing a release agent composition having the composition shown in Table 3 at 60 ° C. for 21 hours, and then removed. The amount of nickel eluted into the bath was measured by an atomic absorption method, and the corrosion rate of the substrate was determined. The results are shown in Table 3.
同様に、ガラス板上にアルミニウムを蒸着した基体
も、上記と同じ浴に15時間浸漬して、腐食性を調べた。
結果を第３表に示す。Similarly, a substrate obtained by evaporating aluminum on a glass plate was immersed in the same bath as above for 15 hours and examined for corrosiveness.
The results are shown in Table 3.
実施例３ ガラス板上にポリイミド樹脂（東レ（株）製）を230
℃で60分間ベークして焼付けた。これを第３表に示す組
成を有する剥離剤組成物を含む浴中に所定温度にて30分
間浸漬した後、ポリイミド樹脂の膨潤又は溶解の有無を
観察した。結果を第３表に示すように、アミドとしてジ
メチルホルムアミド又はジメチルアセトアミドを用いる
剥離剤組成物によれば、80℃においても、ポリイミド樹
脂は膨潤溶解しない。Example 3 230 polyimide resin (manufactured by Toray Industries, Inc.) on a glass plate
Baked at 60 ° C for 60 minutes. After this was immersed in a bath containing a release agent composition having the composition shown in Table 3 at a predetermined temperature for 30 minutes, the presence or absence of swelling or dissolution of the polyimide resin was observed. As shown in Table 3, according to the release agent composition using dimethylformamide or dimethylacetamide as the amide, the polyimide resin does not swell and dissolve even at 80 ° C.
第３表において、剥離剤番号１及び４は、N,N−ジメ
チルホルムアミド又はN,N−ジメチルアセトアミドとジ
エチレングリコールモノブチルエーテルとからなり、参
考例としての有機溶剤型剥離剤組成物を示し、剥離剤番
号７はアミドとしてＮ−メチルピロリドンを用いた比較
例としての有機溶剤型剥離剤組成物を示し、剥離剤番号
２、３、５及び６が本発明による水性剥離剤組成物であ
る。In Table 3, release agents Nos. 1 and 4 consist of N, N-dimethylformamide or N, N-dimethylacetamide and diethylene glycol monobutyl ether, and show an organic solvent type release agent composition as a reference example. No. 7 shows an organic solvent type release agent composition as a comparative example using N-methylpyrrolidone as an amide, and release agents Nos. 2, 3, 5 and 6 are aqueous release agent compositions according to the present invention.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−168651（ＪＰ，Ａ) 特開 昭63−186243（ＪＰ，Ａ) 特開 昭60−26945（ＪＰ，Ａ) 特開 昭60−131535（ＪＰ，Ａ) 特開 昭60−26340（ＪＰ，Ａ) 特開 昭63−50838（ＪＰ，Ａ) 特開 昭57−163236（ＪＰ，Ａ) 特開 昭57−165834（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) G03F 7/42──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-63-168651 (JP, A) JP-A-63-186243 (JP, A) JP-A-60-26945 (JP, A) JP-A 60-26945 131535 (JP, A) JP-A-60-26340 (JP, A) JP-A-63-50838 (JP, A) JP-A-57-163236 (JP, A) JP-A-57-165834 (JP, A) (58) Field surveyed (Int.Cl. 6 , DB name) G03F 7/42
Claims (5)
膜を剥離するための水性剥離剤組成物であつて、 （ａ） N,N−ジメチルホルムアミド及びN,N−ジメチル
アセトアミドよりなる群から選ばれる少なくとも１種の
鎖状アミド５〜30重量％、 及び （ｂ） ジエチレングリコールモノブチルエーテル95〜
70重量％ とからなる混合物100重量部と、 （ｃ） 水 50〜200重量部 とからなることを特徴とする水性剥離剤組成物。1. An aqueous stripper composition for stripping a positive photoresist film applied on a substrate, comprising: (a) a water-based stripper composition selected from the group consisting of N, N-dimethylformamide and N, N-dimethylacetamide. 5 to 30% by weight of at least one selected linear amide; and (b) 95 to 95% diethylene glycol monobutyl ether.
An aqueous release agent composition comprising: 100 parts by weight of a mixture consisting of 70% by weight; and (c) 50 to 200 parts by weight of water.
ルモノブチルエーテル90〜80重量％との混合物100重量
部と、水50〜200重量部とからなる請求項１に記載の水
性剥離剤組成物。2. The aqueous release agent composition according to claim 1, comprising 100 parts by weight of a mixture of 10 to 20% by weight of amide and 90 to 80% by weight of diethylene glycol monobutyl ether, and 50 to 200 parts by weight of water.
エーテルとの混合物100重量部と、水75〜150重量部とか
らなる請求項１又は２に記載の水性剥離剤組成物。3. The aqueous release agent composition according to claim 1, comprising 100 parts by weight of a mixture of amide and diethylene glycol monobutyl ether and 75 to 150 parts by weight of water.
基体用の水性剥離剤組成物。4. The aqueous release agent composition for an organic substrate according to claim 1, wherein
ミド基体用の水性剥離剤組成物。5. The aqueous release agent composition for a polyimide substrate according to claim 1, wherein
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63286261A JP2759462B2 (en) | 1988-11-11 | 1988-11-11 | Aqueous release agent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63286261A JP2759462B2 (en) | 1988-11-11 | 1988-11-11 | Aqueous release agent composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02131239A JPH02131239A (en) | 1990-05-21 |
| JP2759462B2 true JP2759462B2 (en) | 1998-05-28 |
Family
ID=17702076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63286261A Expired - Fee Related JP2759462B2 (en) | 1988-11-11 | 1988-11-11 | Aqueous release agent composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2759462B2 (en) |
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| US6030932A (en) * | 1996-09-06 | 2000-02-29 | Olin Microelectronic Chemicals | Cleaning composition and method for removing residues |
| US5780406A (en) * | 1996-09-06 | 1998-07-14 | Honda; Kenji | Non-corrosive cleaning composition for removing plasma etching residues |
| US5759973A (en) * | 1996-09-06 | 1998-06-02 | Olin Microelectronic Chemicals, Inc. | Photoresist stripping and cleaning compositions |
| US5817610A (en) * | 1996-09-06 | 1998-10-06 | Olin Microelectronic Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US6274537B1 (en) * | 1998-08-05 | 2001-08-14 | Samsung Electronics Co., Ltd. | Use of alkoxy N-hydroxyalkyl alkanamide as resist removing agent, composition for removing resist, method for preparing the same and resist removing method using the same |
| KR100335484B1 (en) * | 1998-08-05 | 2002-05-04 | 윤종용 | Use of an Alkoxy N-Hydroxyalkyl Alkanamide as Resist Removing Agent, Composition for Removing Resist, Method for Preparing the Same and Resist Removing Method Using the Same |
| US6413923B2 (en) | 1999-11-15 | 2002-07-02 | Arch Specialty Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| KR100360397B1 (en) * | 1999-11-26 | 2002-11-18 | 삼성전자 주식회사 | Resist removing composition and resist removing method using the same |
| JP2001183850A (en) | 1999-12-27 | 2001-07-06 | Sumitomo Chem Co Ltd | Remover composition |
| JP2009014938A (en) * | 2007-07-03 | 2009-01-22 | Toagosei Co Ltd | Resist release agent composition |
| JP5995092B2 (en) * | 2013-02-20 | 2016-09-21 | 荒川化学工業株式会社 | Cleaning composition for removing polyamideimide resin |
| CA3068808C (en) * | 2017-07-06 | 2024-05-07 | Dow Global Technologies Llc | Amide combinations for cleaning and stripping of electronic parts |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57163236A (en) * | 1981-03-31 | 1982-10-07 | Hitachi Chem Co Ltd | Peeling solution for use in photocured film |
| JPS57165834A (en) * | 1981-04-06 | 1982-10-13 | Hitachi Chem Co Ltd | Peeling solution for cured film of photopolymerizing composition |
| JPS6026945A (en) * | 1983-07-25 | 1985-02-09 | ジエイ・テイ・ベ−カ−・ケミカル・カンパニ− | Stripping composition and stripping of resist |
| JPS6026340A (en) * | 1983-07-25 | 1985-02-09 | ジエイ ティー ベイカー インコーポレーテッド | Stripping composition and stripping of resist |
| JPS60131535A (en) * | 1983-12-20 | 1985-07-13 | エッチエムシー・パテンツ・ホールディング・カンパニー・インコーポレーテッド | Stripping composition for positive photoresist |
| JPS6350838A (en) * | 1986-08-21 | 1988-03-03 | Japan Synthetic Rubber Co Ltd | Removing solution |
| IE59971B1 (en) * | 1986-11-10 | 1994-05-04 | Baker J T Inc | Stripping compositions and their use for stripping resists from substrates |
| JPS63168651A (en) * | 1987-01-06 | 1988-07-12 | Asahi Chem Ind Co Ltd | Stripping agent composition for photoresist |
-
1988
- 1988-11-11 JP JP63286261A patent/JP2759462B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02131239A (en) | 1990-05-21 |
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