CN114035411B - Photoresist stripping liquid - Google Patents
Photoresist stripping liquid Download PDFInfo
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- CN114035411B CN114035411B CN202111217302.0A CN202111217302A CN114035411B CN 114035411 B CN114035411 B CN 114035411B CN 202111217302 A CN202111217302 A CN 202111217302A CN 114035411 B CN114035411 B CN 114035411B
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- Prior art keywords
- photoresist
- nonionic surfactant
- amino acid
- organic solvent
- organic
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 41
- 239000007788 liquid Substances 0.000 title claims abstract description 15
- 150000001413 amino acids Chemical class 0.000 claims abstract description 12
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000007530 organic bases Chemical class 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000008367 deionised water Substances 0.000 claims abstract description 7
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 3
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 claims abstract description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims abstract description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 3
- FDWOMVXWQMSGMZ-UHFFFAOYSA-N 2,6-diamino-6-iminohexanoic acid Chemical compound OC(=O)C(N)CCCC(N)=N FDWOMVXWQMSGMZ-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract description 4
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 abstract description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 abstract description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006260 foam Substances 0.000 abstract description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 abstract description 2
- 229940102253 isopropanolamine Drugs 0.000 abstract description 2
- 239000012528 membrane Substances 0.000 abstract description 2
- 239000012466 permeate Substances 0.000 abstract description 2
- 235000012431 wafers Nutrition 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- -1 alcohol amine Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013473 artificial intelligence Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
The invention relates to photoresist stripping liquid. The membrane removing liquid consists of organic alkali, alkaline amino acid, an organic solvent, a nonionic surfactant and deionized water. The organic base is at least one of ethylamine, triethylamine, ethylenediamine, monoethanolamine, diethanolamine, triethanolamine and isopropanolamine. The basic amino acid is at least one of 2-amino-5-guanidyl pentanoic acid, 2, 6-diaminohexanoic acid and histidine. The organic solvent is at least one of sulfolane, dimethyl sulfoxide, diethyl sulfoxide and NMP, PGME, PGMEA. The nonionic surfactant is at least one of XP80, XP90 and XP 100. Wherein, the organic base and the basic amino acid cooperate to permeate into the interface layer between the photoresist and the film, so that the photoresist is shrunk, the organic solvent causes the photoresist to expand and foam and peel off, and the addition of the nonionic surfactant enhances the wettability of the solution, so that the peeled photoresist is rapidly dissolved.
Description
Technical Field
The invention belongs to the technical field of semiconductor cleaning and silicon wafer regeneration, and particularly relates to photoresist stripping liquid.
Background
Along with the daily and monthly variation of electronic information technology, the updating speed of downstream terminal electronic products driven by 5G technology and artificial intelligence is faster and faster, and huge market space is brought for related industries of electronic components such as flat panel display, semiconductor chips, touch control, circuit boards and the like. The photolithography process is a core technology for transferring patterns in the semiconductor manufacturing process, along with the miniaturization trend of patterns and the consideration of the manufacturing yield, the monitoring frequency needs to be increased in the photolithography process, whether the manufacturing capability of the photolithography equipment is stable or not is controlled by using a test-grade silicon wafer, whether the process of a machine meets the standard or not, and whether the production product is qualified or not.
Thus, in the photolithography process, the test piece needs to be used in a large amount. In order to save the cost, each semiconductor manufacturer needs to send thousands or even tens of thousands of Wafer to Japan for grinding regeneration every year, but the grinding sheet has short service life, can only be used 2-3 times, and has high transportation cost and grinding cost. At present, the regeneration of the export is expensive, and some semiconductor factories use a sulfuric acid soaking mode to remove photoresist on a test silicon wafer, but because the carbonization of sulfuric acid can cause the particle number on the wafer surface to exceed the standard, an effective photoresist stripping solution capable of replacing sulfuric acid is urgently needed to be configured.
The existing film liquid for removing the photoresist mainly comprises a polar organic solvent, alkali, fluoride and water. As in CN107589637a, a photoresist cleaning solution containing fluoride, organic alcohol amine, organic solvent and deionized water is disclosed, which has poor removal ability for photoresist cured at high temperature. As another example CN 108008606A discloses a membrane solution comprising an inorganic base, an organic base, a solvent, additives and water, wherein the inorganic base hydroxide is very corrosive to the silicon substrate of the test strip. As another example, CN102540776a discloses a stripper containing a polymethylphosphoramide, an alkanolamine, an organosilicon polyether compound, an alkynol, a hydroxylamine and deionized water, which can rapidly strip a cured photoresist, but the stripped photoresist macromolecules cannot be dissolved therein, which can clog a machine or a pipeline, thus requiring periodic cleaning of the residual photoresist.
Disclosure of Invention
The invention aims to provide a photoresist stripping liquid which can be used for effectively removing photoresist on a test silicon wafer with high curing temperature and energy and long curing time so as to be reused.
The second object of the present invention is to provide a photoresist stripping solution, which can dissolve the stripped polymer gel into the stripping solution, thereby reducing the load of a cleaning machine.
In order to achieve the above purpose, the technical scheme of the invention provides a photoresist stripping solution, which contains organic base, basic amino acid, organic solvent, nonionic surfactant and deionized water. The content of organic alkali is 5-20%, the content of alkaline amino acid is 1-5%, the content of organic solvent is 20-50%, the content of nonionic surfactant is 0.1-1%, and the balance is deionized water.
Wherein the organic base is at least one of ethylamine, triethylamine, ethylenediamine, monoethanolamine, diethanolamine, triethanolamine and isopropanolamine.
The basic amino acid is at least one of 2-amino-5-guanidyl pentanoic acid, 2, 6-diaminohexanoic acid and histidine.
The organic solvent is at least one of sulfolane, dimethyl sulfoxide, diethyl sulfoxide and NMP, PGME, PGMEA.
The nonionic surfactant is at least one of XP80, XP90 and XP 100.
According to the technical scheme, the organic base and the basic amino acid are synergistic, the organic base and the basic amino acid are soaked into an interface layer between the photoresist and the film, so that the photoresist is shrunken, the organic solvent enables the photoresist to expand and foam and peel off, the addition of the nonionic surfactant enhances the wettability of the solution, and meanwhile, the stripping liquid permeates into a high polymer matrix of the photoresist, so that the intermolecular attraction is broken, and the peeled photoresist is rapidly dissolved into a fine single-molecule substance. The photoresist stripping liquid is used for removing photoresist on production test silicon wafers, and particularly can remove photoresist after high-temperature curing so as to facilitate the reuse of the silicon wafers. The photoresist stripping liquid is used for removing photoresist on production test silicon wafers, and particularly can remove photoresist after high-temperature curing so as to facilitate the reuse of the silicon wafers.
The invention has the advantages and beneficial effects that: in the invention, the photoresist stripping liquid enhances the permeability and the wettability of the liquid medicine by introducing the alkaline amino acid and the nonionic surfactant, so that the photoresist stripping liquid can strip the insoluble photoresist solidified at high temperature and can dissolve the stripped polymer gel.
Drawings
FIG. 1 is a graph showing the effect of photoresist dissolution in the examples, A is the case of total dissolution, and B is the case of insolubility.
Detailed Description
For a better understanding of the present invention, reference will now be made in detail to the drawings and examples, which are illustrated in the accompanying drawings, but are not intended to limit the scope of the invention.
The stripping solution of the invention is prepared by simply and uniformly mixing the components shown in table 1.
Table 1 shows the components and contents of the stripping solutions of examples 1 to 30 and comparative examples 1 to 12.
Cutting a test piece covered with a photoresist film subjected to high-temperature curing into 1.6x1.6cm 2 The pieces of the size were immersed in the photoresist stripping solutions described in examples and comparative examples, respectively, the stripping temperature was 25 to 65℃and the stripping time was not more than 30 minutes each time at 10℃increase according to the stripping effect until the removal was completed, the cleaning time was recorded, the stripping treatment was performed, then the cleaning was performed with ultrapure water, and the stripping effect was evaluated according to the standard. The results of the examples and comparative examples are summarized in table 2.
Table 2 shows the removal of photoresist from the test strips of examples 1 to 30 and comparative examples 1 to 12.
The above A-F and dissolution conditions are shown in the following table:
according to the experimental results of the embodiment, the photoresist stripping liquid provided by the invention can well remove insoluble photoresist solidified at high temperature on the surface of the test piece under the normal temperature condition, and can dissolve stripped polymer gel.
Claims (1)
1. The photoresist stripping liquid is characterized by comprising organic alkali, basic amino acid, an organic solvent, a nonionic surfactant and deionized water; the organic base is 12%, the alkaline amino acid is 3%, the organic solvent is 35%, the nonionic surfactant is 0.6%, and the balance is deionized water, wherein the organic base is at least one of triethylamine, ethylenediamine and monoethanolamine, the alkaline amino acid is at least one of 2-amino-5-guanylvaleric acid and 2, 6-diaminocaproic acid, the organic solvent is at least one of sulfolane, dimethyl sulfoxide, diethyl sulfoxide and NMP, PGME, PGMEA, and the nonionic surfactant is at least one of XP80, XP90 and XP 100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111217302.0A CN114035411B (en) | 2021-10-19 | 2021-10-19 | Photoresist stripping liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111217302.0A CN114035411B (en) | 2021-10-19 | 2021-10-19 | Photoresist stripping liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114035411A CN114035411A (en) | 2022-02-11 |
| CN114035411B true CN114035411B (en) | 2023-11-10 |
Family
ID=80135497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111217302.0A Active CN114035411B (en) | 2021-10-19 | 2021-10-19 | Photoresist stripping liquid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114035411B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005043874A (en) * | 2003-06-26 | 2005-02-17 | Dongwoo Fine-Chem Co Ltd | Photoresist stripping liquid composition and method for stripping photoresist by using the same |
| CN102227687A (en) * | 2008-12-25 | 2011-10-26 | 长瀬化成株式会社 | Photoresist remover composition, method for removing photoresist of multilayer metal circuit board, and method for producing multilayer metal circuit board |
| CN104317172A (en) * | 2014-09-30 | 2015-01-28 | 深圳新宙邦科技股份有限公司 | Stripper for stripping photoresist |
| CN107022421A (en) * | 2009-09-30 | 2017-08-08 | 富士胶片株式会社 | The manufacture method of cleaning method and semiconductor device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6501492B2 (en) * | 2014-10-31 | 2019-04-17 | 関東化學株式会社 | Composition for removing photoresist residue and / or polymer residue |
-
2021
- 2021-10-19 CN CN202111217302.0A patent/CN114035411B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005043874A (en) * | 2003-06-26 | 2005-02-17 | Dongwoo Fine-Chem Co Ltd | Photoresist stripping liquid composition and method for stripping photoresist by using the same |
| CN102227687A (en) * | 2008-12-25 | 2011-10-26 | 长瀬化成株式会社 | Photoresist remover composition, method for removing photoresist of multilayer metal circuit board, and method for producing multilayer metal circuit board |
| CN107022421A (en) * | 2009-09-30 | 2017-08-08 | 富士胶片株式会社 | The manufacture method of cleaning method and semiconductor device |
| CN104317172A (en) * | 2014-09-30 | 2015-01-28 | 深圳新宙邦科技股份有限公司 | Stripper for stripping photoresist |
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| Publication number | Publication date |
|---|---|
| CN114035411A (en) | 2022-02-11 |
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Address after: 443007 no.66-3, Yiting Avenue, Yiting District, Yichang City, Hubei Province Applicant after: Hubei Xingfu Electronic Materials Co.,Ltd. Address before: 443007 no.66-3, Yiting Avenue, Yiting District, Yichang City, Hubei Province Applicant before: HUBEI SINOPHORUS ELECTRONIC MATERIALS CO.,LTD. |
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