CN101169597A - Photoresist detergent - Google Patents

Photoresist detergent Download PDF

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Publication number
CN101169597A
CN101169597A CNA2006101176675A CN200610117667A CN101169597A CN 101169597 A CN101169597 A CN 101169597A CN A2006101176675 A CNA2006101176675 A CN A2006101176675A CN 200610117667 A CN200610117667 A CN 200610117667A CN 101169597 A CN101169597 A CN 101169597A
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CN
China
Prior art keywords
out system
ether
photoresist clean
clean
photoresist
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.)
Pending
Application number
CNA2006101176675A
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Chinese (zh)
Inventor
彭洪修
史永涛
刘兵
曾浩
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Anji Microelectronics Shanghai Co Ltd
Anji Microelectronics Co Ltd
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Anji Microelectronics Shanghai Co Ltd
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Publication date
Application filed by Anji Microelectronics Shanghai Co Ltd filed Critical Anji Microelectronics Shanghai Co Ltd
Priority to CNA2006101176675A priority Critical patent/CN101169597A/en
Priority to PCT/CN2007/003021 priority patent/WO2008049332A1/en
Priority to CNA2007800374807A priority patent/CN101523299A/en
Publication of CN101169597A publication Critical patent/CN101169597A/en
Pending legal-status Critical Current

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    • 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

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention discloses a detergent for removing the photosensitive resist, and contains dimethyl sulfoxide and quaternary ammonium hydroxid, and is characterized in that a surface active agent, i.e. hydroxyl-containing polyether is still included. The detergent for removing the photosensitive resist, which includes the surface active agent of hydroxyl-containing polyether, has an excellent cleansing power for the photosensitive resist (photo resist) and other leftovers on metal, metal alloy or dielectric medium base materials, and has a favorable applied prospect in the rinse of semiconductor wafers and other micro-electronics fields.

Description

A kind of photoresist clean-out system
Technical field
The present invention relates to the cleaning field in the semiconductor manufacturing, relate in particular to a kind of photoresist clean-out system.
Background technology
In common semiconductor fabrication process,, utilize wet method or dry etching to carry out figure transfer after the exposure by going up the mask that forms photoresist on surfaces such as silicon dioxide, Cu metals such as (copper) and low-k materials.Low temperature cleaning fast is the important directions of semiconductor wafer fabrication process development.In addition, carry out in the chemical cleaning process of photoresist at semiconductor wafer, clean-out system regular meeting causes the corrosion of wafer substrate.Particularly utilizing chemical to remove in the process of metal etch residue, metal erosion is comparatively generally and very serious problem, often causes the remarkable reduction of wafer yield.
At present, the photoresist clean-out system mainly is made up of polar organic solvent, surfactant and/or water etc., by immersing semiconductor wafer in the clean-out system or utilizing clean-out system flushing semiconductor wafer, removes the photoresist on the semiconductor wafer.
Patent documentation US5863346 and patent documentation WO9739092 are surfactant with the dodecylbenzene sulfonic acid, form the photoresist clean-out system with m-diisopropyl benzene, and wafer is immersed in this clean-out system, remove the photoresist on the metal base under 65～80 ℃.Its corrosion to the semiconductor wafer base material is higher, and can not remove the photoresist on the semiconductor wafer, cleansing power deficiency fully.Patent documentation US6368421 and patent documentation WO0003306 are with BASF
Figure A20061011766700051
B-26 line style alkoxyl alcohol is a surfactant, form the photoresist clean-out system with sulfolane (SFL), dipropylene glycol monomethyl ether (DPGME) and deionized water etc., wafer is immersed in this clean-out system, in the photoresist of removing under 25～85 ℃ on metal and the dielectric substrate.This photoresist clean-out system can not be removed the photoresist on the semiconductor wafer, cleansing power deficiency fully.
Summary of the invention
The purpose of this invention is to provide a kind of photoresist clean-out system with good cleansing power.
Photoresist clean-out system among the present invention comprises dimethyl sulfoxide (DMSO), quaternary ammonium hydroxide, it is characterized in that also containing surfactant: hydroxyl polyethers (HPE).The hydroxyl polyethers can improve the meltage of quaternary ammonium hydroxide in the clean-out system, and clean-out system is to the wetting capacity of semiconductor wafer base material.
Wherein, that the content of described hydroxyl polyethers is preferable is 0.001～15wt%, and that better is 0.05～5.0wt%; That the content of described dimethyl sulfoxide (DMSO) is preferable is 70～99wt%, and that better is 80～99wt%; That the content of described quaternary ammonium hydroxide is preferable is 0.01～15wt%, and that better is 0.5～10wt%.
Among the present invention, what described quaternary ammonium hydroxide was preferable is Tetramethylammonium hydroxide (TMAH), tetraethyl ammonium hydroxide, TPAOH, TBAH or benzyltrimethylammonium hydroxide.Wherein, better is Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide or TBAH, and best is Tetramethylammonium hydroxide.
Among the present invention, described photoresist clean-out system also can further comprise the polarity organic cosolvent.That the content of described polarity organic cosolvent is preferable is 0～29.5wt%, and that better is 5.0～25wt%.Described polarity organic cosolvent is preferable is selected from sulfoxide, sulfone, imidazolidinone, alkylene glycol monoalkyl ether and/or alkyl diol aryl ether.What wherein, described sulfoxide was preferable is the diethyl sulfoxide or the first and second basic sulfoxides etc.; What described sulfone was preferable is methyl sulfone, ethyl sulfone and sulfolane, and better is sulfolane; What described imidazolidinone was preferable is 2-imidazolidinone (MI), 1,3-dimethyl-2-imidazolidinone (DMI) or 1, and 3-diethyl-2-imidazolidinone, better is 1,3-dimethyl-2-imidazolidinone; What described alkylene glycol monoalkyl ether was preferable is glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, the single ether of dipropylene glycol or dipropylene glycol monobutyl ether, and better is glycol monoethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether or dipropylene glycol monomethyl ether; Described alkyl diol aryl ether is preferable be glycol monomethyl phenyl ether (EGMPE), propylene glycol list phenyl ether (PGMPE), Isopropanediol list phenyl ether, diethylene glycol list phenyl ether, the single phenyl ether of dipropylene glycol, di-isopropylene glycol list phenyl ether, glycol monomethyl benzylic ether, propylene glycol single-benzyl ether or Isopropanediol single-benzyl ether, and better is glycol monomethyl phenyl ether or propylene glycol list phenyl ether.
Among the present invention, described photoresist clean-out system also can further comprise water.That the content of described water is preferable is 0～29.5wt%, and that better is 0.5～25wt%.
Among the present invention, described photoresist clean-out system also can further comprise corrosion inhibiter.That the content of described corrosion inhibiter is preferable is 0～10wt%, and that better is 0.05～5.0wt%.Described corrosion inhibiter is selected from phenols, carboxylic acid (ester) class, anhydrides or phosphonic acids (ester) class corrosion inhibiter.
Wherein, what described phenols was preferable is 1,2-dihydroxy phenol, para hydroxybenzene phenol or 1,2,3,-thrihydroxy-benzene, and better is 1,2,3,-thrihydroxy-benzene; What described carboxylic acid (ester) class was preferable is benzoic acid, p-aminobenzoic acid (PABA), phthalic acid (PA), gallic acid (GA) or n-propyl gallate, and better is p-aminobenzoic acid, phthalic acid or gallic acid; What described anhydrides was preferable is acetic anhydride, propionic andydride, caproic anhydride or (gathering) maleic anhydride, and better is HPMA; What described phosphonic acids (ester) class was preferable is 1,3-(hydroxyethyl)-2,4, and 6-tri methylene phosphonic acid (HEDPA), Amino Trimethylene Phosphonic Acid (ATMP) or 2-phosphonic acids butane-1,2,4-tricarboxylic acids (PBTCA), better is 1,3-(hydroxyethyl)-2,4,6-tri methylene phosphonic acid.
Photoresist clean-out system of the present invention can get by said components is simple mixed.
Photoresist clean-out system of the present invention, can use as follows: the semiconductor wafer that will be covered with photoresist immerses photoresist clean-out system of the present invention, under room temperature to 85 ℃, utilize slowly vibration 10～30 minutes of constant temperature oscillator, dry up (if cleaning temperature is higher than 45 ℃ with high pure nitrogen after utilizing deionized water wash, should use the washed with isopropyl alcohol wafer earlier, use deionized water wash again).
Positive progressive effect of the present invention is: the photoresist clean-out system contains the hydroxyl polyethet surfactant among the present invention.The hydroxyl polyethers can improve the meltage of quaternary ammonium hydroxide in the clean-out system, and clean-out system is to the wetting capacity of semiconductor wafer base material.Photoresist clean-out system of the present invention has good cleansing power for the photoresist on metal, metal alloy or the dielectric substrate (photoresistance) and other residue, can have a good application prospect at microelectronics such as semiconductor wafer cleanings at room temperature to the 85 ℃ following photoresist of removing the above thickness of 10 μ m on the semiconductor wafer.Its effect will further specify by the contrast experiment among the embodiment.
Embodiment
Mode below by embodiment further specifies the present invention, does not therefore limit the present invention among the described scope of embodiments.
Embodiment 1～32
Table 1 has provided the embodiment 1～32 of photoresist clean-out system.
Table 1 photoresist clean-out system embodiment 1～32
Figure A20061011766700081
Figure A20061011766700091
Figure A20061011766700101
Effect embodiment 1
Table 2 contrast clean-out system 1～8 and clean-out system 1～5 contained component and content thereof
Figure A20061011766700102
Figure A20061011766700111
Contrast clean-out system 1～8 and clean-out system 1～5 among the effect embodiment 1 are used to clean blank Cu wafer, measure its etch-rate for metal Cu.Method of testing and condition: blank Cu wafer is immersed clean-out system, under room temperature to 85 ℃, utilize slowly vibration 10～30 minutes of constant temperature oscillator, behind deionized water wash, dry up then with high pure nitrogen.If cleaning temperature is higher than 45 ℃, should use the washed with isopropyl alcohol wafer earlier, use deionized water wash again.Utilize four utmost point probe machines to measure blank Cu chip etching front and rear surfaces changes in resistance at last, calculate gained and the results are shown in table 3.
The solution state of table 3 contrast clean-out system 1～8 and clean-out system 1～5,
To the etch-rate of blank Cu wafer and to the cleansing power of photoresist
Clean-out system Solution state The pH value Cu, 25 ℃ of .A/min of etch-rate Photoresist cleans The photoresist wash result
Contrast clean-out system 1 Clarification 12.13 11.54 25℃，30min Substantially complete
Contrast clean-out system 2 Clarification 12.16 11.06 25℃，30min Substantially complete
Contrast clean-out system 3 Clarification 12.11 10.88 25℃，30min Substantially complete
Contrast clean-out system 4 Clarification 12.15 10.76 25℃，30min Substantially complete
Contrast clean-out system 5 The minute quantity Tetramethylammonium hydroxide is insoluble - - - -
Contrast clean-out system 6 The minute quantity Tetramethylammonium hydroxide is insoluble - - - -
Contrast clean-out system 7 Clarification 12.22 11.69 25℃，30min Fully
Contrast clean-out system 8 The minute quantity Tetramethylammonium hydroxide is insoluble - - - -
Clean-out system 1 Clarification 12.24 9.86 30℃，20min Fully
Clean-out system 2 Clarification 12.09 1.52 30℃，25min Fully
Clean-out system 3 Clarification 12.14 2.24 85℃，10min Fully
Clean-out system 4 Clarification 12.14 2.24 25℃，25min Fully
Clean-out system 5 Clarification 12.36 3.62 25℃，25min Fully
By table 2,3 as seen: compare with contrast clean-out system 1～8, the meltage of the quaternary ammonium hydroxide of clean-out system 1～5 is improved; Show good photoresist cleansing power; And the corrosivity to blank metal Cu wafer reduces.
Raw material used in the present invention and reagent are the commercially available prod.

Claims (26)

1. a photoresist clean-out system comprises dimethyl sulfoxide (DMSO), quaternary ammonium hydroxide, it is characterized in that also containing surfactant: the hydroxyl polyethers.
2. photoresist clean-out system according to claim 1 is characterized in that: the content of described hydroxyl polyethers is 0.001～15wt%.
3. photoresist clean-out system according to claim 2 is characterized in that: the content of described hydroxyl polyethers is 0.05～5.0wt%.
4. photoresist clean-out system according to claim 1 is characterized in that: the content of described dimethyl sulfoxide (DMSO) is 70～99wt%.
5. photoresist clean-out system according to claim 4 is characterized in that: the content of described dimethyl sulfoxide (DMSO) is 80～99wt%.
6. photoresist clean-out system according to claim 1 is characterized in that: the content of described quaternary ammonium hydroxide is 0.01～15wt%.
7. photoresist clean-out system according to claim 6 is characterized in that: the content of described quaternary ammonium hydroxide is 0.5～10.0wt%.
8. photoresist clean-out system according to claim 1 is characterized in that: described quaternary ammonium hydroxide is Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, TPAOH, TBAH or benzyltrimethylammonium hydroxide.
9. photoresist clean-out system according to claim 1 is characterized in that: described photoresist clean-out system also comprises polarity organic cosolvent, corrosion inhibiter and/or water.
10. photoresist clean-out system according to claim 9 is characterized in that: the content of described polarity organic cosolvent is 0～29.5wt%.
11. photoresist clean-out system according to claim 10 is characterized in that: the content of described polarity organic cosolvent is 5.0～25wt%.
12. photoresist clean-out system according to claim 9 is characterized in that: the content of described corrosion inhibiter is 0～10wt%.
13. photoresist clean-out system according to claim 12 is characterized in that: the content of described corrosion inhibiter is 0.05～5.0wt%.
14. photoresist clean-out system according to claim 9 is characterized in that: the content of described water is 0～29.5wt%.
15. photoresist clean-out system according to claim 14 is characterized in that: the content of described water is 0.5～25wt%.
16. photoresist clean-out system according to claim 9 is characterized in that: described polarity organic cosolvent is sulfoxide, sulfone, imidazolidinone, alkylene glycol monoalkyl ether and/or alkyl diol aryl ether.
17. photoresist clean-out system according to claim 16 is characterized in that: described sulfoxide is the diethyl sulfoxide or the first and second basic sulfoxides.
18. photoresist clean-out system according to claim 16 is characterized in that: described sulfone is methyl sulfone, ethyl sulfone or sulfolane.
19. photoresist clean-out system according to claim 16 is characterized in that: described imidazolidinone is a 2-imidazolidinone, 1,3-dimethyl-2-imidazolidinone or 1,3-diethyl-2-imidazolidinone.
20. photoresist clean-out system according to claim 16 is characterized in that: described alkylene glycol monoalkyl ether is glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, the single ether of dipropylene glycol or dipropylene glycol monobutyl ether.
21. photoresist clean-out system according to claim 16 is characterized in that: described alkyl diol aryl ether comprises glycol monomethyl phenyl ether, propylene glycol list phenyl ether, Isopropanediol list phenyl ether, diethylene glycol list phenyl ether, the single phenyl ether of dipropylene glycol, di-isopropylene glycol list phenyl ether, glycol monomethyl benzylic ether, propylene glycol single-benzyl ether or Isopropanediol single-benzyl ether.
22. photoresist clean-out system according to claim 9 is characterized in that: described corrosion inhibiter is selected from phenols, carboxylic acid (ester) class, anhydrides or phosphonic acids (ester) class corrosion inhibiter.
23. photoresist clean-out system according to claim 22 is characterized in that: described phenols is 1,2-dihydroxy phenol, para hydroxybenzene phenol or 1,2,3,-thrihydroxy-benzene.
24. photoresist clean-out system according to claim 22 is characterized in that: described carboxylic acid (ester) class is benzoic acid, p-aminobenzoic acid, phthalic acid, gallic acid or n-propyl gallate.
25. photoresist clean-out system according to claim 22 is characterized in that: described anhydrides is acetic anhydride, propionic andydride, caproic anhydride or (gathering) maleic anhydride.
26. photoresist clean-out system according to claim 22 is characterized in that: described phosphonic acids (ester) class is 1,3-(hydroxyethyl)-2,4,6-tri methylene phosphonic acid, Amino Trimethylene Phosphonic Acid or 2-phosphonic acids butane-1,2,4-tricarboxylic acids.
CNA2006101176675A 2006-10-27 2006-10-27 Photoresist detergent Pending CN101169597A (en)

Priority Applications (3)

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CNA2006101176675A CN101169597A (en) 2006-10-27 2006-10-27 Photoresist detergent
PCT/CN2007/003021 WO2008049332A1 (en) 2006-10-27 2007-10-22 A cleaning compound for removing photoresist
CNA2007800374807A CN101523299A (en) 2006-10-27 2007-10-22 A cleaning compound for removing photoresist

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CNA2006101176675A CN101169597A (en) 2006-10-27 2006-10-27 Photoresist detergent

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CNA2007800374807A Pending CN101523299A (en) 2006-10-27 2007-10-22 A cleaning compound for removing photoresist

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101566804B (en) * 2009-05-11 2011-06-15 绵阳艾萨斯电子材料有限公司 Developing agent for flat-panel display
CN102618900A (en) * 2012-04-14 2012-08-01 修建东 Triode surface treatment liquid and preparation method thereof
CN103616805A (en) * 2013-10-25 2014-03-05 青岛华仁技术孵化器有限公司 Cleaning fluid used in semiconductor manufacture process
US10121649B2 (en) 2008-12-04 2018-11-06 Siltronic Ag Cleaning method of semiconductor wafer
CN108803262A (en) * 2018-07-03 2018-11-13 昆山欣谷微电子材料有限公司 A kind of acidity photoresist lift off liquid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8092430B2 (en) 2008-03-03 2012-01-10 Tyco Healthcare Group Lp Single port device with multi-lumen cap

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3514782B2 (en) * 1992-08-31 2004-03-31 旭化成ケミカルズ株式会社 Low residue cleaning agent
US5399285A (en) * 1992-10-30 1995-03-21 Diversey Corporation Non-chlorinated low alkalinity high retention cleaners
EP1544324A4 (en) * 2002-08-19 2005-11-09 Merk Kanto Advanced Chemical L Remover solution
US8236485B2 (en) * 2002-12-20 2012-08-07 Advanced Technology Materials, Inc. Photoresist removal

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10121649B2 (en) 2008-12-04 2018-11-06 Siltronic Ag Cleaning method of semiconductor wafer
CN101566804B (en) * 2009-05-11 2011-06-15 绵阳艾萨斯电子材料有限公司 Developing agent for flat-panel display
CN102618900A (en) * 2012-04-14 2012-08-01 修建东 Triode surface treatment liquid and preparation method thereof
CN102618900B (en) * 2012-04-14 2016-12-14 烟台恒迪克能源科技有限公司 A kind of Triode surface treatment liquid and preparation method thereof
CN103616805A (en) * 2013-10-25 2014-03-05 青岛华仁技术孵化器有限公司 Cleaning fluid used in semiconductor manufacture process
CN108803262A (en) * 2018-07-03 2018-11-13 昆山欣谷微电子材料有限公司 A kind of acidity photoresist lift off liquid

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CN101523299A (en) 2009-09-02

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