JPH0248668A - Resist removing agent - Google Patents
Resist removing agentInfo
- Publication number
- JPH0248668A JPH0248668A JP19899888A JP19899888A JPH0248668A JP H0248668 A JPH0248668 A JP H0248668A JP 19899888 A JP19899888 A JP 19899888A JP 19899888 A JP19899888 A JP 19899888A JP H0248668 A JPH0248668 A JP H0248668A
- Authority
- JP
- Japan
- Prior art keywords
- removing agent
- org
- phenol
- resist removing
- dissolution
- 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
Links
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 7
- 238000004090 dissolution Methods 0.000 abstract description 6
- 229910052759 nickel Inorganic materials 0.000 abstract description 5
- 229910052718 tin Inorganic materials 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002739 metals Chemical class 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は混合有機溶媒の組成物に係り、特に半導体工業
等で用いられるレジスト材料の剥離剤として好適な組成
物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a composition of mixed organic solvents, and particularly to a composition suitable as a stripping agent for resist materials used in the semiconductor industry and the like.
従来のレジスト剥離剤に関しては、例えば代表的な例と
して、米国特許筒３，８７１，９２９号に報告されてい
る。これはフェノール（ｐｈｅｎｏｌ）（或いは酢酸）
、フェノール・スルフォン酸（ｐｈｅｎｏｌ ５ｕｌｆ
ｏｎｉｃ ａｃｉｄ）および塩素含有炭化水素（ｃｈｌ
ｏｒｉｎａｔｅｄ ｈｙｄｒｏｃａｒｂｏｎ）等を含有
するものである。A typical example of conventional resist stripping agents is reported in US Pat. No. 3,871,929. This is phenol (or acetic acid)
, phenol sulfonic acid (phenol 5ulf
onic acids) and chlorine-containing hydrocarbons (chl
orinated hydrocarbon).
上記した従来のレジスト剥離剤は、１００〜１５０℃に
加熱した状態で試料を浸漬することによりホトレジスト
などの有機物を除去することを目的としていた。ところ
がＮｉ、Ｓｎ、ＡＱ等の金属が溶解する点について配慮
がなされておらず。The conventional resist stripping agents described above were intended to remove organic substances such as photoresist by immersing a sample in a heated state of 100 to 150°C. However, no consideration was given to the fact that metals such as Ni, Sn, and AQ would dissolve.
そのため、例えばＡｕとＮｉの複合蒸着膜等の形成され
た試料に使用した場合、Ｎｉを溶解してしまうという解
決すべき課題があった。Therefore, when used for a sample formed with a composite deposited film of Au and Ni, for example, there was a problem that Ni would be dissolved.
本発明の目的は、上記Ｎｉ、Ｓｎ、ＡＱ等の金属材料を
溶解しないレジスト剥離剤を提供することにある。An object of the present invention is to provide a resist stripping agent that does not dissolve metal materials such as Ni, Sn, and AQ.
上記の目的を達成するため本発明は次の組成の剥離剤を
用いるものである。In order to achieve the above object, the present invention uses a stripping agent having the following composition.
（１）フェノール ：約１０〜４０％（重量濃度
）
（２）アルキルベンゼンスルフォン酸
＝ ３０〜７０％
（重量濃度）
（３）塩素含有有機化合物： ５〜３０％（例えば、
クロロベンゼン、へキサクロロエタン等） （総重量
濃度）（４）有機アルカリ ° １〜２０％（重
量濃度）
有機アルカリを添加することが１本発明の主要点で、原
組成中のフェノール、クロルベンゼン。(1) Phenol: Approximately 10-40% (weight concentration) (2) Alkylbenzenesulfonic acid = 30-70% (weight concentration) (3) Chlorine-containing organic compound: 5-30% (e.g.
(chlorobenzene, hexachloroethane, etc.) (total weight concentration) (4) Organic alkali ° 1 to 20% (weight concentration) The main point of the present invention is to add an organic alkali to phenol and chlorobenzene in the original composition.
ヘキサクロロエタン等と相溶性の良い有機アルカリが好
ましい。望むらくは沸点２００℃程度のものが良い。具
体的にはクロロアニリン、アニリン。Organic alkalis having good compatibility with hexachloroethane and the like are preferred. Preferably, the boiling point is about 200°C. Specifically, chloroaniline and aniline.
ピリジン等の芳香族アミン；トリｎプロピルアミン、ヘ
キサメチレンジアミン等の脂肪族アミン；テトラメチル
アンモニウムハイドロオキサイド等のアンモニウム塩等
がある。Examples include aromatic amines such as pyridine; aliphatic amines such as trin-propylamine and hexamethylene diamine; and ammonium salts such as tetramethylammonium hydroxide.
従来のレジスト剥離剤にはアルキルベンゼンスルフォン
酸、フェノールの他に、クロルベンゼンおよびヘキサク
ロロエタン等の塩素含有有機化合物が含有されている。Conventional resist stripping agents contain chlorine-containing organic compounds such as chlorobenzene and hexachloroethane in addition to alkylbenzenesulfonic acids and phenols.
ここに工程途中でＨ２Ｏが混入するとＨＣＱが生成され
、これがＮｉ、Ｓｎ。When H2O is mixed in during the process, HCQ is generated, which is Ni and Sn.
へΩ等を溶解する。以上の事は我々が行った故意にＨ２
Ｏを添加してＮｉの溶解速度を測定する実験から見出さ
れたものである。Dissolve Ω etc. The above was done intentionally by H2
This was discovered through an experiment in which the dissolution rate of Ni was measured by adding O.
上記不良をなくするためには、Ｈ２Ｏの混入を避けるこ
とが考えられるが、通常の工程では微量水分の混入は避
は難い。しかし１本発明のレジスト剥離剤にはあらがじ
め有機アルカリが添加しであるので、もし水分が混入し
てＨＣＩが生成しても、それは有機アルカリにより中和
され、溶解の主因たるＨＣＱは除去される。In order to eliminate the above-mentioned defects, it is possible to avoid the contamination of H2O, but in normal processes, it is difficult to avoid the contamination of trace amounts of water. However, since organic alkali is added to the resist stripping agent of the present invention in advance, even if water gets mixed in and HCI is generated, it will be neutralized by the organic alkali, and HCQ, which is the main cause of dissolution, will be removed. removed.
実施例１゜
以下本発明の詳細な説明する。混合有機溶媒の重量組成
は、アルキルベンゼンスルフォン酸の一種のドデシルベ
ンゼンスルフォン酸５５−ｔ％。Example 1 The present invention will be described in detail below. The weight composition of the mixed organic solvent is 55-t% of dodecylbenzenesulfonic acid, which is a type of alkylbenzenesulfonic acid.
フェノール２０ｗｔ％、クロルベンゼン１０−ｔ％。20 wt% phenol, 10-t% chlorobenzene.
ヘキサクロロエタン１０υｔ％、および有機アルカリと
してクロロアニリン５ｗｔ％とした。該組成物を１００
℃に加温した状態で１μｍ厚の市販ポジ形ホトレジスト
（東京応化製０ＦＰＲ８００）を浸漬したところ５分間
で完全に溶解し、レジスト剥離剤として従来品に劣らず
良好な特性を有していることがわかった。この時、Ａυ
とＮｌの重ね膜中のＮｉ蒸着膜の溶解は認められず、浸
漬時間を１時間まで延長しても２０Å以上の７容解は検
出できなかった。Hexachloroethane was 10 υt%, and chloroaniline was 5 wt% as an organic alkali. 100% of the composition
When a 1 μm thick commercially available positive photoresist (0FPR800 manufactured by Tokyo Ohka Chemical Co., Ltd.) was immersed in the product heated to ℃, it completely dissolved in 5 minutes, and the resist stripping agent had as good properties as conventional products. I understand. At this time, Aυ
No dissolution of the Ni vapor deposited film in the overlapping film of Nl and Nl was observed, and even if the immersion time was extended to 1 hour, no solution of 20 Å or more could be detected.
また次の実施例試料Ｎｏ、２〜８のような重量組成の混
合有機溶媒を作製し、先の実施例１と同様。In addition, mixed organic solvents having the weight compositions of sample Nos. 2 to 8 of the next example were prepared in the same manner as in the previous example 1.
Ｎ ｉ ／ Ａ ｕ重ね膜上でのレジスト剥離実験を行
った結果、従来のレジスト剥離剤と同様に良好なレジス
ト剥離性を示し、がっＮｉの溶解は認められなかった。As a result of conducting a resist peeling experiment on the Ni/Au stacked film, the resist peeling property was as good as that of conventional resist stripping agents, and no dissolution of Ni was observed.
これら剥離剤の例を下表に示す。Examples of these release agents are shown in the table below.
なお、塩素含有有機化合物の組成は５〜３０ｗｔ％の範
囲で選択可能であり、そのときはフェノール、アルキル
ベンゼンスルフォン酸の組成を変えて全体の組成調整を
行なう。Note that the composition of the chlorine-containing organic compound can be selected within the range of 5 to 30 wt%, and in that case, the overall composition is adjusted by changing the composition of phenol and alkylbenzenesulfonic acid.
以上のように本発明によれば、比較的酸に溶解しやすい
金属蒸着膜を用いた試料にも適用可能なレジスト剥離剤
が得られる。As described above, according to the present invention, a resist stripping agent can be obtained that can be applied to samples using metal vapor deposited films that are relatively easily dissolved in acids.
Claims (1)
０〜７０％のアルキルベンゼンスルフォン酸および総重
量濃度５〜３０％の塩素含有有機化合物を含有するレジ
スト剥離剤において重量濃度１〜２０％の有機アルカリ
を含有させたことを特徴とするレジスト剥離剤。1. Phenol with a weight concentration of about 10-40%, weight concentration 3
A resist stripping agent comprising 0 to 70% of alkylbenzene sulfonic acid and a chlorine-containing organic compound with a total weight concentration of 5 to 30%, which contains an organic alkali at a weight concentration of 1 to 20%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19899888A JPH0638162B2 (en) | 1988-08-11 | 1988-08-11 | Resist stripper |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19899888A JPH0638162B2 (en) | 1988-08-11 | 1988-08-11 | Resist stripper |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0248668A true JPH0248668A (en) | 1990-02-19 |
| JPH0638162B2 JPH0638162B2 (en) | 1994-05-18 |
Family
ID=16400400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19899888A Expired - Lifetime JPH0638162B2 (en) | 1988-08-11 | 1988-08-11 | Resist stripper |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0638162B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09298201A (en) * | 1996-04-30 | 1997-11-18 | Nec Corp | Method for forming wiring pattern |
| US5759973A (en) * | 1996-09-06 | 1998-06-02 | Olin Microelectronic Chemicals, Inc. | Photoresist stripping and cleaning compositions |
| US5780406A (en) * | 1996-09-06 | 1998-07-14 | Honda; Kenji | Non-corrosive cleaning composition for removing plasma etching residues |
| US5817610A (en) * | 1996-09-06 | 1998-10-06 | Olin Microelectronic Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US6030932A (en) * | 1996-09-06 | 2000-02-29 | Olin Microelectronic Chemicals | Cleaning composition and method for removing residues |
| US6413923B2 (en) | 1999-11-15 | 2002-07-02 | Arch Specialty Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| JP2007327513A (en) * | 2006-06-06 | 2007-12-20 | Toyota Motor Corp | Reverse gear noise preventing transmission |
-
1988
- 1988-08-11 JP JP19899888A patent/JPH0638162B2/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09298201A (en) * | 1996-04-30 | 1997-11-18 | Nec Corp | Method for forming wiring pattern |
| US5759973A (en) * | 1996-09-06 | 1998-06-02 | Olin Microelectronic Chemicals, Inc. | Photoresist stripping and cleaning compositions |
| US5780406A (en) * | 1996-09-06 | 1998-07-14 | Honda; Kenji | Non-corrosive cleaning composition for removing plasma etching residues |
| US5817610A (en) * | 1996-09-06 | 1998-10-06 | Olin Microelectronic Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US6020292A (en) * | 1996-09-06 | 2000-02-01 | Olin Microelectronic Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US6030932A (en) * | 1996-09-06 | 2000-02-29 | Olin Microelectronic Chemicals | Cleaning composition and method for removing residues |
| US6191086B1 (en) | 1996-09-06 | 2001-02-20 | Arch Specialty Chemicals, Inc. | Cleaning composition and method for removing residues |
| US6413923B2 (en) | 1999-11-15 | 2002-07-02 | Arch Specialty Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US7001874B2 (en) | 1999-11-15 | 2006-02-21 | Arch Specialty Chemicals, Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| US7402552B2 (en) | 1999-11-15 | 2008-07-22 | Fujifilm Electronic Materials U.S.A., Inc. | Non-corrosive cleaning composition for removing plasma etching residues |
| JP2007327513A (en) * | 2006-06-06 | 2007-12-20 | Toyota Motor Corp | Reverse gear noise preventing transmission |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0638162B2 (en) | 1994-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |