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WO2003038529A1 - Procede de liberation de resist - Google Patents

Procede de liberation de resist Download PDF

Info

Publication number
WO2003038529A1
WO2003038529A1 PCT/JP2002/011358 JP0211358W WO03038529A1 WO 2003038529 A1 WO2003038529 A1 WO 2003038529A1 JP 0211358 W JP0211358 W JP 0211358W WO 03038529 A1 WO03038529 A1 WO 03038529A1
Authority
WO
WIPO (PCT)
Prior art keywords
resist
resist stripping
weight
solution
film
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.)
Ceased
Application number
PCT/JP2002/011358
Other languages
English (en)
Japanese (ja)
Inventor
Hideki Shimizu
Hiroshi Matsunaga
Masaru Ohto
Kazuto Ikemoto
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.)
Mitsubishi Gas Chemical Co Inc
Original Assignee
Mitsubishi Gas Chemical Co Inc
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
Priority claimed from JP2001338438A external-priority patent/JP2003140365A/ja
Priority claimed from JP2001338436A external-priority patent/JP2003140364A/ja
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Priority to US10/493,700 priority Critical patent/US20040256358A1/en
Priority to CNB028216881A priority patent/CN100338530C/zh
Publication of WO2003038529A1 publication Critical patent/WO2003038529A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02041—Cleaning
    • H01L21/02043—Cleaning before device manufacture, i.e. Begin-Of-Line process
    • H01L21/02052—Wet cleaning 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
    • G03F7/425—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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31127—Etching organic layers
    • H01L21/31133—Etching organic layers by chemical means
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31127—Etching organic layers
    • H01L21/31133—Etching organic layers by chemical means
    • H01L21/31138—Etching organic layers by chemical means by dry-etching

Definitions

  • the present invention relates to a resist stripping solution used for manufacturing a semiconductor integrated circuit, a liquid crystal panel, an organic EL panel, a printed circuit board, and the like, and a resist stripping method.
  • Photoresists used when using lithography technology are used in a wide range of fields such as integrated circuits such as ICs and LSIs, display devices such as LCDs and EL devices, printed circuit boards, micromachines, DNA chips, and microplants. I have. ,
  • a solution containing an organic solvent and a water-soluble solvent has been used as a resist stripping solution.
  • amine compounds are often used as organic alkalis, for example, non-aqueous solutions of alkanolamine and dimethyl sulfoxide, alkanolamine, water-soluble organic solvents, and aqueous solutions containing sugar alcohols, alkanolamines, hydroxylamines.
  • aqueous solutions containing catechol have been used.
  • resist stripping solutions have been generally used in the range of room temperature to 100 ° C. for stripping resists mainly on substrates not mainly containing copper such as aluminum and aluminum alloys.
  • the present inventors have conducted extensive studies on a resist stripping solution for a copper wiring board and found that a composition containing an amine compound, a solvent, a strong alkali and water can strip a resist without corroding copper or a copper alloy. I found what I could do.
  • the present inventors have diligently studied the optimal conditions for stripping the resist without corroding copper. As a result, it has been generally said that the amine compound corrodes the copper. However, oxygen dissolved in the resist stripper oxidizes copper, and the oxidized copper dissolves as a copper-amine complex. It was found that the corrosion of the wiring progressed, that is, the oxygen dissolved in the resist stripper was the main factor of the copper corrosion.
  • the present invention provides a wiring board having a residual resist film after etching, in an atmosphere of oxygen concentration of 2 vol. 0/0 or less, to provide a resist stripping method characterized by contacting the resist stripper.
  • a resist stripping method characterized by contacting the resist stripper.
  • after pretreatment with hydrogen peroxide it is brought into contact with a resist stripper.
  • the present invention provides a resist stripping solution containing an amine compound, a solvent, a strong alkali and water, which can be preferably used in the above resist stripping method.
  • the resist stripping solution of the present invention contains an amine compound, a solvent, a strong alkali (optional component), and water.
  • Amine compounds include ammonia, monoalkylamines, dialkylamines, trialkylamines, alkanolamines, polyamines, hydroxylamine compounds, and cyclic amines.
  • Monoalkylamines include methylamine, ethylamine, n-propylamine, isopropynoleamine, n-butylamine, sec-butylamine, isopamine. Tinoleamine, t-butylamine, pentylamine, 2-aminopentane, 3-aminopentane, 1-amino-2-methylbutane, 2-amino-2-methylbutane, 3-amino-2-methylbutane, 4-amino-12-methinolebutane, hexinoleamine, 5-amino-2-methylpentane, heptylamine, octylamine, nonylamine, decylamine, pendecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, etc
  • alkanolamines examples include ethanolamine, 1-amino-12-propanol, N- (aminoethyl) ethanolamine, N-methylethanolamine, N-ethyethanolanolamine, ⁇ -propynoleethanolamine, and ⁇ .
  • Polyamines include ethylenediamine, propanediamine, trimethylenediamine, tetramethylenediamine, 1,3-diaminobutane, 2,3-diaminobutane, pentamethylenediamine, 2,4-diaminopentane, hexamethylenediamine, heptamethylenediamine.
  • hydroxylamine compound examples include hydroxylamine, N-methylhydroxynoleamine, N-ethylhydroxylamine, and N, N-getylhydroxylamine.
  • Cyclic amines include pyrrole, 2-methylpyrrole, 3-methylpyrrole, 2-ethylpyrrole, 3-ethylpyrrole, 2,3-dimethylpyrrole, 2,4 -Dimethylpyrrole, 3,4-Dimethylvironole, 2,3,4_Trimethinolepyrrole, 2,3,5-Trimethinolepyrrole, 2_Pyroline, 3_Pyroline, Pyrrolidine, 2-Methyl ⁇ Pyrrolidine, 3-methylpyrrolidine, pyrazole, imidazole, 1,2,3-triazole, 1,2,3,4-tetrazole, piperidine, 2-pipecoline, 3-pipecoline, 4-pipecoline, 2,4-norepetidine, 2,61-norepetidine, 3,5-lupetidine, piperazine, 2-methinoleviperazine, 2,5-dimethylbiperazine, 2,6-methylbiperazine, morpholine and
  • ethanolamine 1-amino-2-propanol, N- (aminoethyl) ethanolamine, N-methylethanolamine, N-ethylethanolamine, diethanolamine, isopropanolamine Selected from the group consisting of min, 2- (2-aminoethoxy) ethanol, ethylenediamine, propanediamine, butylenediamine, diethylenetriamine, piperazine, mo ⁇ / holin, triethylenetetraamine, tetraethylenepentamine, and pentaethylenehexamine. At least one compound is preferred.
  • the strong alkali is selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, choline hydroxide, and acetylcholine hydroxide. Further, at least one compound is preferable, and tetramethylammonium hydroxide and choline hydroxide are more preferable.
  • the solvent is preferably miscible with the amine compound.
  • Ethylene glycol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethinoethyl ether, diethylene glycol alcohol Monoethylene phenol, diethylene glycol monobutyl phenol, propylene glycol monomethyl phenol, propylene glycol monomethyl ether, propylene glycol phenol monolith phenol, dipropylene daricone monomethyl phenol , Dipropylene glycol monomethyl ether, dipropylene glycol mono / lemonobutynoole ether, diethylene glycol dimethinole ether, dipropylene glycol dimethyl ether
  • Ter solvents formamide, monomethylformamide, Dimethylformamide, Monoethylformamide, Getylformamide, Acetamide, Monomethylacetamide, Dimethylacetamide, Monoethylacetamide, Jethylacetamide, N-Methylpyrrolidone
  • dimethyl sulfoxide, ⁇ , ⁇ -dimethylformalde, ⁇ , ⁇ -dimethylacetamide, ⁇ -methylpyrrolidone, diethylene glycol monomethinoleate ether, diethylene glycol monoptinole ether, dipropylene glycol monomethyl ether Noreether, dipropylene glycol / lemonoptinoleatenole, and propylene glycol are preferred because they are easily available, have a high boiling point, and are easy to use. Further, the amine compound can be used as a solvent.
  • the resist stripping solution should be 5 to 95% by weight of the amine compound, 3 to 85% by weight of the solvent, and 0.01 to 5% by weight. 1 to 25% by weight of water and preferably 1 to 25% by weight of an amine compound.
  • the resist stripping solution of the present invention can contain additives such as a conventionally used anticorrosive such as sorbitol and catechol, and a surfactant, as long as the effects of the present invention are not impaired.
  • the method for producing the resist stripping solution is not particularly limited, and is manufactured by a conventionally known method.
  • the resist is removed by etching the resist, preferably before the ashing, to a resist stripping solution containing an amine compound, a solvent, a strong alkali (optional component), and water at 20 to 60 ° C. By contacting for 1 to 30 minutes. Contact is usually made by immersing the substrate with the remaining resist in a resist stripper. Will be
  • the surface of a widely used phenolic hydroxyl group-containing resist is altered by dry etching.
  • a conventional resist stripper strips the resist by forming a salt between the amine compound and the phenolic hydroxyl group and adding the amine compound to a carbonyl group formed by oxidation.
  • the ability to remove the deteriorated resist is small.
  • by using a resist stripper containing a strong alcohol the ability to form a salt with a phenolic hydroxyl group and the ability to remove halogen from dry etching can be enhanced.
  • a function of hydrolysis can be added.
  • the resist stripping operation is performed in an atmosphere having an oxygen concentration of 2% by volume or less, preferably 1% by volume or less, to effectively suppress the corrosion of the copper-copper alloy.
  • the low oxygen atmosphere is obtained by using nitrogen, argon, hydrogen or the like, preferably nitrogen.
  • a gas such as nitrogen, argon, or hydrogen is blown into the resist stripping solution to expel the dissolved gas and maintain the dissolved oxygen amount in the resist stripping solution at 3 ppm or less. Then, by performing the resist stripping operation, the corrosion of copper and the ⁇ alloy can be more effectively suppressed.
  • the resist stripper may be degassed before use.
  • the resist stripping method of the present invention is most effective when removing the remaining resist on the substrate having the copper film or the copper alloy film.
  • pretreatment with hydrogen peroxide is effective for peeling off the further deteriorated resist.
  • the pretreatment with hydrogen peroxide oxidizes the surface of the deteriorated resist, reduces the molecular weight, and promotes the formation of carbonyl groups. This facilitates resist removal.
  • the wiring substrate was subjected to a hydrogen peroxide concentration of 0.5 weight after etching and before the treatment with a resist stripper. /.
  • the solution is brought into contact with a 1 to 10% by weight solution at 20 to 60 ° C for 1 to 30 minutes, for example, by immersion or the like.
  • the solution include an aqueous solution.
  • Chelating agents in hydrogen peroxide solution An additive such as a surfactant may be added.
  • the wiring substrate pretreated with hydrogen peroxide is subjected to the above-described resist stripping operation as it is or after being washed with water or the like.
  • T E T A Triethylenetetramine
  • TMAH Tetramethylammonium hydroxide
  • CH Choline hydroxide
  • TETA Triethylenetetramine
  • AEEA Aminoethylethanolamine
  • TMAH Tetramethylammonium hydroxide
  • the resist peeling of the wiring board can be performed without corroding the copper film. Further, by performing the pretreatment with hydrogen peroxide, the resist stripping can be easily performed even when the resist stripping solution alone is difficult.
  • a silicon substrate having a copper film having a thickness of 40 OA was immersed in a resist stripper having the following composition, and the corrosion rate of the copper film was measured at 50 ° C. Table 5 shows the results.
  • Example 14 Nitrogen gas was used as a resist stripper 0 3
  • Example 15 In 1% oxygen-containing nitrogen
  • a silicon substrate having a copper film having a thickness of 400 A was immersed in a resist stripper having the following composition, and the corrosion rate of the copper film was measured at 50 ° C. The measurement was performed in a glove box with an oxygen concentration meter in the atmosphere. Table 6 shows the results. Resist stripper composition
  • Example 16 Nitrogen atmosphere with an oxygen concentration of 200 ppm 1.3
  • a silicon substrate having a copper film with a thickness of 40 OA was immersed in a resist stripper having the following composition, and the corrosion rate of the film was measured at 50 ° C. The measurement was performed in a glove box with an oxygen concentration meter in the atmosphere.
  • N- Mechirupirori Don 5 5 by weight 0/0
  • Comparative Example 7 4.5 1 ⁇
  • the present invention it has become possible to remove the resist after dry etching without corroding copper. As a result, it has become possible to use a resist stripper, which could not be used for processing a substrate having a conventional wiring. In addition, pretreatment with hydrogen peroxide has made it possible to easily remove resist that was difficult to remove.

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  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Cleaning Or Drying Semiconductors (AREA)

Abstract

L'invention concerne un procédé de libération d'un résist consistant à mettre en contact un tableau de connexions, présentant une couche mince de résist résiduelle, avec un fluide libérant du résist, sous une atmosphère ayant une teneur en oxygène de 2 % en volume ou moins. Le traitement précité de libération d'un résist est de préférence exécuté après que la couche mince de résist résiduelle ne soit prétraitée au peroxyde d'hydrogène. Dans le procédé, un fluide libérant du résist contenant un composé amine, un solvant, un alcali fort et de l'eau est de préférence utilisé.
PCT/JP2002/011358 2001-11-02 2002-10-31 Procede de liberation de resist Ceased WO2003038529A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/493,700 US20040256358A1 (en) 2001-11-02 2002-10-31 Method for releasing resist
CNB028216881A CN100338530C (zh) 2001-11-02 2002-10-31 剥离抗蚀剂的方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2001-338438 2001-11-02
JP2001338438A JP2003140365A (ja) 2001-11-02 2001-11-02 レジスト剥離液の使用方法
JP2001-338436 2001-11-02
JP2001338436A JP2003140364A (ja) 2001-11-02 2001-11-02 銅配線基板向けレジスト剥離液

Publications (1)

Publication Number Publication Date
WO2003038529A1 true WO2003038529A1 (fr) 2003-05-08

Family

ID=26624329

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/011358 Ceased WO2003038529A1 (fr) 2001-11-02 2002-10-31 Procede de liberation de resist

Country Status (5)

Country Link
US (1) US20040256358A1 (fr)
KR (1) KR20050042051A (fr)
CN (1) CN100338530C (fr)
TW (1) TWI311694B (fr)
WO (1) WO2003038529A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
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KR100781925B1 (ko) * 2002-04-26 2007-12-04 도오꾜오까고오교 가부시끼가이샤 포토레지스트 박리 방법
EP1959303A4 (fr) * 2005-12-01 2010-01-27 Mitsubishi Gas Chemical Co Solution de nettoyage pour dispositif à semi-conducteur ou dispositif d'affichage et procédé de nettoyage

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TWI692679B (zh) * 2017-12-22 2020-05-01 美商慧盛材料美國責任有限公司 光阻剝除劑
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JP7322137B2 (ja) * 2019-03-26 2023-08-07 株式会社フジミインコーポレーテッド 表面処理組成物、その製造方法、表面処理方法および半導体基板の製造方法
CN114207529A (zh) * 2019-07-30 2022-03-18 三菱瓦斯化学株式会社 光致抗蚀剂去除用组合物
CN112480928A (zh) * 2019-09-11 2021-03-12 利绅科技股份有限公司 硅蚀刻组成物及其作用于硅基材的蚀刻方法
CN112711176A (zh) * 2020-12-17 2021-04-27 芯越微电子材料(嘉兴)有限公司 一种适用半导体领域的光刻胶剥离液及制备方法
KR20220150134A (ko) 2021-05-03 2022-11-10 삼성전자주식회사 포토레지스트 박리 조성물과 이를 이용하는 반도체 소자 및 반도체 패키지의 제조 방법

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US20040256358A1 (en) 2004-12-23
TWI311694B (en) 2009-07-01

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