IP Library Granted Patent US 8,679,734
Granted Patent B2
US 8,679,734 · App. 13/568,790 · Granted Mar 25, 2014

Photoresist removal

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Quick Facts
Patent No.
US 8,679,734
App. No.
13/568,790
Granted
Mar 25, 2014
Kind
B2
Abstract

Disclosed herein is a composition and method for semiconductor processing. In one embodiment, a wet-cleaning composition for removal of photoresist is provided. The composition comprises a strong base; an oxidant; and a polar solvent. In another embodiment, a method for removing photoresist is provided. The method comprises the steps of applying a wet-cleaning composition comprising about 0.1 to about 30 weight percent strong base; about one to about 30 weight percent oxidant; about 20 to about 95 weight percent polar solvent; and removing the photoresist.

Claims (25)

1. A cleaning solution comprising a strong base, an oxidant, and a polar solvent, wherein said oxidant comprises a species selected from the group consisting of an amine-N-oxide, a percarbonate salt, and a perborate salt, wherein the pH of the solution is greater than 11.5, and wherein said solution is useful for removing post-etch photoresist residue from a semiconductor substrate having same thereon.

2. The cleaning solution of claim 1 , wherein the amount of each component is

about 20 to about 95 wt % polar solvent;

about 0.1 to about 30 wt % strong base; and

about 1 to about 30 wt % oxidant.

3. The cleaning solution of claim 1 , wherein said polar solvent comprises a polar species selected from the group consisting of water, an alcohol, ethylene glycol, propylene glycol, glycol ethers thereof, an amide, and a carbonate.

4. The cleaning solution of claim 1 , wherein said polar solvent comprises water.

5. The cleaning solution of claim 1 , wherein the strong base comprises a nitrogen containing compound of the formula (NR 1 R 2 R 3 R 4 ) + OH − , wherein R 1 , R 2 , R 3 and R 4 are each one of hydrogen, alkyl or substituted aryl groups.

6. The cleaning solution of claim 1 , wherein said strong base comprises tetramethylammonium hydroxide.

7. The cleaning solution of claim 1 , wherein said oxidant comprises an amine-N-oxide.

8. The cleaning solution of claim 1 , wherein said amine-N-oxide has the formula:

wherein R 1 and R 2 may be hydrogen, methyl, further substituted or unsubstituted alkyl groups or may form two ends of an alkyl chain, and R 3 may be methyl, further substituted or unsubstituted alkyl groups or may form two ends of an alkyl chain.

9. The cleaning solution of claim 1 , wherein said amine-N-oxide comprises N-methylmorpholine-N-oxide.

10. The cleaning solution of claim 1 , wherein the solution comprises water, amine-N-oxide, and tetramethylammonium hydroxide.

11. The cleaning solution of claim 1 , wherein the solution comprises water, N-methylmorpholine-N-oxide, and tetramethylammonium hydroxide.

12. The cleaning solution of claim 11 , further comprising 2-mercaptobenzimidazole.

13. The cleaning solution of claim 1 , further comprising at least one chelator selected from the group consisting of 1,2,3-triazole, 1,2,4-triazole, benzotriazole, polyltriazole, 5-phenyl-benzotriazole, 5-nitro-benzotriazole, 1-amino-1,2,3-triazole, 1-amino-1,2,4-triazole, 1-amino-5-methyl-1,2,3-triazole, hydroxybenzotriazole, 2-(5-amino-pentyl)-benzotriazole, 3-amino-1,2,4-triazole, 3-isopropyl-1,2,4-triazole, 3-mercapto-1,2,4-triazole, 5-phenylthiol-benzotriazole, halo-benzotriazoles, napthotriazole, 2-mercaptobenzoimidizole, 2-mercaptobenzothiazole, 5-aminotetrazole, 5-amino-1,3,4-triadiazole-2-thiol, thiazole, triazine, methyltetrazole, 1,3-dimethyl-2-imidazolidinone, 1,5-pentamethylenetetrazole, 1-phenyl-5-mercaptotetrazole, diaminomethyltriazine, mercaptobenzothiazole, imidazoline thione, mercaptobenzoimidazole, 4-methyl-4H-1,2,4-triazole-3-thiol, benzothiazole, tritolyl phosphate, indiazole, guanine, adenine, glycerol, thioglycerol, nitrilotriacetic acid, salicylamide, iminodiacetic acid, benzoguanamine, melamine, thiocyranuric acid, anthranilic acid, 8-hydroxyquinoline, 5-carboxylic acid-benzotriazole, 3-mercaptopropanol, boric acid, and iminodiacetic acid.

14. The cleaning solution of claim 1 , further comprising a co-solvent, wherein said co-solvent is one of an alkylamine, an alkanolamine, a glycol, and a glycol ether.

15. The cleaning solution of claim 1 , further comprising a surfactant.

16. A method to remove post-etching photoresist residue from a semiconductor substrate comprising contacting the semiconductor substrate with a cleaning solution for a sufficient amount of time to effect substantial cleaning of the semiconductor substrate, wherein the cleaning solution comprises a strong base, an oxidant, and a polar solvent, wherein said oxidant comprises a species selected from the group consisting of an amine-N-oxide, a percarbonate salt, and a perborate salt, and wherein the pH of the solution is greater than 11.5.

17. The method of claim 16 , wherein said polar solvent comprises a polar species selected from the group consisting of water, an alcohol, ethylene glycol, propylene glycol, glycol ethers thereof, an amide, and a carbonate.

18. The method of claim 16 , wherein the strong base comprises a nitrogen containing compound of the formula (NR 1 R 2 R 3 R 4 ) + OH − , wherein R 1 , R 2 , R 3 and R 4 are each one of hydrogen, alkyl or substituted aryl groups.

19. The method of claim 16 , wherein said oxidant comprises an amine-N-oxide.

20. The method of claim 19 , wherein said amine-N-oxide has the formula:

wherein R 1 and R 2 may be hydrogen, methyl, further substituted or unsubstituted alkyl groups or may form two ends of an alkyl chain, and R 3 may be methyl, further substituted or unsubstituted alkyl groups or may form two ends of an alkyl chain.

Assignments (8)
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
ASSIGNMENT OF PATENT SECURITY INTEREST RECORDED AT REEL/FRAME 048811/0679 Recorded Nov 5, 2019
From: GOLDMAN SACHS BANK USA
To: MORGAN STANLEY SENIOR FUNDING, INC.
Reel/Frame 050965/0035 →
SECURITY INTEREST Recorded Nov 13, 2018
From: ENTEGRIS, INC.; SAES PURE GAS, INC.
To: GOLDMAN SACHS BANK USA
Reel/Frame 048811/0679 →
RELEASE OF SECURITY INTEREST Recorded Nov 8, 2018
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ATMI PACKAGING, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.
Reel/Frame 047477/0151 →
RELEASE OF SECURITY INTEREST Recorded Nov 8, 2018
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ATMI PACKAGING, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.
Reel/Frame 047477/0032 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2016
From: ADVANCED TECHNOLOGY MATERIALS, INC.
To: ENTEGRIS, INC.
Reel/Frame 041029/0903 →
SECURITY INTEREST Recorded May 2, 2014
From: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.; ATMI PACKAGING, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 032812/0192 →
SECURITY INTEREST Recorded May 1, 2014
From: ENTEGRIS, INC.; POCO GRAPHITE, INC.; ATMI, INC.; ADVANCED TECHNOLOGY MATERIALS, INC.; ATMI PACKAGING, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 032815/0852 →