WO2000033139A1 - Agent de decollement de photoresist, et procede de decollement associe - Google Patents
Agent de decollement de photoresist, et procede de decollement associe Download PDFInfo
- Publication number
- WO2000033139A1 WO2000033139A1 PCT/JP1999/006728 JP9906728W WO0033139A1 WO 2000033139 A1 WO2000033139 A1 WO 2000033139A1 JP 9906728 W JP9906728 W JP 9906728W WO 0033139 A1 WO0033139 A1 WO 0033139A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- photoresist
- stripping
- dmpu
- stripper
- stripping solution
- Prior art date
Links
Classifications
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- 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
- G03F7/34—Imagewise removal by selective transfer, e.g. peeling away
-
- 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
-
- 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 a photoresist stripping solution and a photoresist stripping method using the stripping solution.
- Photoresist is used in various technical fields, such as the manufacture of semiconductor integrated circuits and the manufacture of flat panel display (FPD) display components such as liquid crystal displays, and structuring processes such as etching masks or implantation (eg, ion implantation). Used as a mask for If the photo resist is used as a mask material, it is usually removed after serving its purpose. Many lifting strippers are used to remove the photoresist.
- photoresist stripping solutions include stripping solutions comprising aryl sulfonic acids such as benzene sulfonic acid (Japanese Patent Laid-Open No. 54-135,777), and chlorine-based organic solvents and the like.
- the present invention provides a stripper that satisfies all of the various characteristics that have been demanded of the above-mentioned conventional photoresist stripper, that is, it can be used in a short time even when the temperature of the stripper itself is room temperature.
- the photoresist can be completely peeled off, has little corrosive effect on wiring materials, etc., and does not precipitate insolubles even if it is rinsed with water after the peeling process.
- An object of the present invention is to provide a photoresist stripper which has both functions and is highly safe for the environment and the human body, and to provide a photoresist stripping method using the stripper. Disclosure of the invention
- 13 ⁇ 4 1 Oyobi 1 ⁇ 2 are each a hydrogen atom or aralkyl having 1 to 4 carbon atoms Represents a kill group.
- the present invention relates to a photoresist stripper containing a pyrimidinone compound represented by the above general formula (I).
- the present invention also relates to a method for stripping photoresist using a photoresist stripper containing a pyrimidinone compound represented by the above general formula (I).
- Examples of the pyrimidinone compound represented by the above general formula (I) that can be used in the present invention include, for example, 1,3-dimethyl-3,4,5,6—tetrahydro-1-2 (1H) -pyrimidinone (Dimethylpropyleneurea), 1,3-Jetyl-3,4,5,6-Tetrahydro-1 (1H) -pyrimidinone, 1,3-Di-n-Propyl-3,4,5,6- Tetrahydro-1 (1H) -pyrimidinone, 1,3-di-iso-propyl-1,3,4,5,6-tetrahydro-1 (1H) -pyrimidinone. These pyrimidinone compounds are used alone or in combination of two or more.
- the pyrimidinone compound can be used as it is as a photoresist stripper, that is, it can be used as a 100% solution of the pyrimidinone compound, or the pyrimidinone compound can be used in another solvent. Can also be used as a mixture.
- the solvent that can be used by mixing with the above pyrimidinone compound include, for example, water, amines such as monoethanolamine and N-methylisopropylamine, dimethylformamide, and N-methyl-2-pyrrolidone.
- glycol ethers such as ethylene daryl glycol monoethyl ether and its acetates
- ketones such as acetone and methyl ethyl ketone
- dimethyl sulfoxide These solvents can be used alone or in combination of two or more.
- the content of the pyrimidinone compound in the stripping solution is preferably 10% by weight or more. If less than 10% by weight, The effect of using the limidinone compound is reduced.
- the object to be stripped may be immersed in a stripper at room temperature for several minutes. At this time, in some cases, the peeling force can be further improved by heating the peeling liquid or using ultrasonic waves in combination. In the present invention, such a method is adopted as necessary. Is also good. If the stripping treatment is performed using the stripping solution of the present invention, a photoresist that has been subjected to a boss baking at a high temperature in order to improve the adhesion can also be easily stripped.
- the photoresist stripping solution containing the pyrimidinone compound on the object to be stripped can be easily removed by rinsing with water.
- insoluble substances were precipitated during this rinse, and they were re-adhered to the substrate after stripping, which could adversely affect the performance of articles such as semiconductor substrates. Since such a problem does not occur with the stripping solution, semiconductor integrated circuits, FPD devices, and the like can be manufactured with high yield.
- the stripping solution of the present invention can provide favorable results when applied to any conventionally known photoresist, a particularly preferred result is a “novolak resin quinonediazide compound” -based positive resist. Seen when applied to a project. BEST MODE FOR CARRYING OUT THE INVENTION
- DMPU Dimethyl propylene urea
- M EA monoethanolamine
- MIPA N-methylisopropylamine
- NMP N-methyl-2-pyrrolidone
- DMSO dimethylsulfoxide
- AZ®300M IF manufactured by Clariant Japan Co., Ltd.
- the evaluation of peeling is based on the following evaluation criteria.
- Example 1 DMPU 100% ⁇ ⁇ ⁇ ⁇
- Example 2 MEA: D PU 9: 1 O ⁇ ⁇ ⁇
- a dried AZ® TFP-650 prepared by removing the solvent by evaporation and removing the solvent from Photoresist®®650 manufactured by Clariant Japan Co., Ltd. was prepared and used in Examples 1 to 13 and Comparative Examples.
- Example 14 of 2 to 26 and Comparative Examples 5 to 10 g of the stripping solution having the composition described in 5 to 8 were added to 0.174, 0.348, 0.522, 0.6, respectively. 96, 0.870 and 1.044 g were dissolved respectively.
- the stripping solution of the present invention can be suitably used as a photoresist stripping solution when manufacturing semiconductor integrated circuits, FPD display parts, and the like.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Paints Or Removers (AREA)
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99957400A EP1054297A4 (en) | 1998-12-03 | 1999-12-01 | PHOTO-RESISTANT COATING AND DE-COATING PROCESS |
KR1020007008352A KR20010040496A (ko) | 1998-12-03 | 1999-12-01 | 감광성 내식막 박리액 및 박리방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10344089A JP2000171986A (ja) | 1998-12-03 | 1998-12-03 | フォトレジスト剥離液および剥離方法 |
JP10/344089 | 1998-12-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000033139A1 true WO2000033139A1 (fr) | 2000-06-08 |
Family
ID=18366575
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1999/006728 WO2000033139A1 (fr) | 1998-12-03 | 1999-12-01 | Agent de decollement de photoresist, et procede de decollement associe |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1054297A4 (ja) |
JP (1) | JP2000171986A (ja) |
KR (1) | KR20010040496A (ja) |
CN (1) | CN1248056C (ja) |
MY (1) | MY130894A (ja) |
TW (1) | TW459166B (ja) |
WO (1) | WO2000033139A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101017738B1 (ko) * | 2002-03-12 | 2011-02-28 | 미츠비시 가스 가가쿠 가부시키가이샤 | 포토레지스트 박리제 조성물 및 세정 조성물 |
JP2005173369A (ja) * | 2003-12-12 | 2005-06-30 | Tokyo Ohka Kogyo Co Ltd | レジストパターンの剥離方法 |
KR101109057B1 (ko) * | 2004-07-12 | 2012-01-31 | 주식회사 동진쎄미켐 | 포토레지스트 제거용 씬너 조성물 |
US7355672B2 (en) * | 2004-10-04 | 2008-04-08 | Asml Netherlands B.V. | Method for the removal of deposition on an optical element, method for the protection of an optical element, device manufacturing method, apparatus including an optical element, and lithographic apparatus |
KR101036753B1 (ko) | 2008-11-07 | 2011-05-24 | 주식회사 동부하이텍 | 화학증폭형 포토레지스트용 첨가제 및 이를 포함하는 화학증폭형 포토레지스트 조성물 |
JP5321389B2 (ja) * | 2009-09-28 | 2013-10-23 | 東ソー株式会社 | レジスト剥離剤及びそれを用いた剥離方法 |
JP5829952B2 (ja) * | 2011-03-08 | 2015-12-09 | 株式会社ダイセル | フォトレジスト製造用組成物の製造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS491444A (ja) * | 1972-04-24 | 1974-01-08 | ||
DE3828513A1 (de) * | 1988-08-23 | 1990-03-01 | Merck Patent Gmbh | Abloesemittel fuer fotoresists |
JPH06250405A (ja) * | 1993-02-24 | 1994-09-09 | Hitachi Chem Co Ltd | 水溶性レジストの剥離方法 |
-
1998
- 1998-12-03 JP JP10344089A patent/JP2000171986A/ja active Pending
-
1999
- 1999-12-01 KR KR1020007008352A patent/KR20010040496A/ko not_active Application Discontinuation
- 1999-12-01 TW TW088120968A patent/TW459166B/zh not_active IP Right Cessation
- 1999-12-01 WO PCT/JP1999/006728 patent/WO2000033139A1/ja not_active Application Discontinuation
- 1999-12-01 CN CNB998026387A patent/CN1248056C/zh not_active Expired - Fee Related
- 1999-12-01 EP EP99957400A patent/EP1054297A4/en not_active Withdrawn
- 1999-12-02 MY MYPI99005246A patent/MY130894A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS491444A (ja) * | 1972-04-24 | 1974-01-08 | ||
DE3828513A1 (de) * | 1988-08-23 | 1990-03-01 | Merck Patent Gmbh | Abloesemittel fuer fotoresists |
JPH06250405A (ja) * | 1993-02-24 | 1994-09-09 | Hitachi Chem Co Ltd | 水溶性レジストの剥離方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1054297A4 * |
Also Published As
Publication number | Publication date |
---|---|
CN1289416A (zh) | 2001-03-28 |
EP1054297A1 (en) | 2000-11-22 |
TW459166B (en) | 2001-10-11 |
EP1054297A4 (en) | 2002-04-17 |
KR20010040496A (ko) | 2001-05-15 |
JP2000171986A (ja) | 2000-06-23 |
MY130894A (en) | 2007-07-31 |
CN1248056C (zh) | 2006-03-29 |
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