IP Library Granted Patent US 9,914,902
Granted Patent B2
US 9,914,902 · App. 14/979,787 · Granted Mar 13, 2018

Stripping compositions for removing photoresists from semiconductor substrates

Inventors: Bing Du (Gilbert, AZ); Thomas Dory (Gilbert, AZ); William A. Wojtczak (Austin, TX)
Assignee: Fujifilm Electronic Materials U.S.A., Inc.
C11D11/0047C11D3/0026C11D3/2006C11D3/28C11D3/30C11D3/43C11D7/261C11D7/3209C11D7/3281C11D7/5009C11D7/5013C11D7/5022G03F7/423G03F7/425G03F7/426H01L21/31133
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Quick Facts
Patent No.
US 9,914,902
App. No.
14/979,787
Granted
Mar 13, 2018
Kind
B2
Abstract

This disclosure relates to photoresist stripping compositions containing 1) at least one water soluble polar aprotic organic solvent; 2) at least one alcohol solvent; 3) at least one quaternary ammonium hydroxide; 4) water; 5) at least one copper corrosion inhibitor selected from 6-substituted-2,4-diamino-1,3,5-triazines; and 6) optionally, at least one defoaming surfactant.

Claims (63)

1. A photoresist stripping composition, comprising:

1) at least one water soluble polar aprotic organic solvent in an amount of from about 30% to about 90% of the composition;

2) at least one alcohol solvent;

3) at least one quaternary ammonium hydroxide;

4) water;

5) at least one copper corrosion inhibitor selected from the group consisting of 6-substituted-2,4-diamino-1,3,5-triazines, the substituent at the 6-position being a substituted or unsubstituted aryl group; and

6) optionally, at least one defoaming surfactant.

2. The composition of claim 1 , wherein the at least one quaternary ammonium hydroxide comprises a compound of the formula [NR 1 R 2 R 3 R 4 ] + OH, in which each of R 1 , R 2 , R 3 , and R 4 , independently, is a linear, branched, or cyclic alkyl group optionally substituted by hydroxy, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzyl group.

3. The composition of claim 2 , wherein each of R 1 , R 2 , R 3 , and R 4 , independently, is a C 1 -C 4 alkyl group, a hydroxyethyl group, a phenyl group, or a benzyl group.

4. The composition of claim 1 , wherein the composition comprises from about 0.1% to about 10% of the at least one quaternary ammonium hydroxide.

5. The composition of claim 1 , wherein the at least one copper corrosion inhibitor comprises 6-phenyl-2,4-diamino-1,3,5-triazine.

6. The composition of claim 1 , wherein the composition comprises from about 0.1% to about 10% of the at least one copper corrosion inhibitor.

7. The composition of claim 1 , wherein the at least one water soluble polar aprotic organic solvent comprises dimethyl sulfoxide, sulfolane, dimethylsulfone, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, gamma-butyrolactone, propylene carbonate, 1,3-dimethyl-2-imidazolidinone, or a mixture thereof.

8. The composition of claim 1 , wherein the at least one alcohol solvent comprises an alkane diol, a glycol, an alkoxyalcohol, a saturated aliphatic monohydric alcohol, an unsaturated non-aromatic monohydric alcohol, an alcohol containing a ring structure, or a mixture thereof.

9. The composition of claim 1 , wherein the composition comprises from about 5% to about 60% of the at least one alcohol solvent.

10. The composition of claim 1 , wherein the composition comprises from about 2.5% to about 25% of water.

11. The composition of claim 1 , wherein the composition comprises from about 0.01% to about 3% of the at least one defoaming surfactant.

12. The composition of claim 1 , further comprising at least one aluminum corrosion inhibitor.

13. A photoresist stripping composition, comprising:

1) at least one water soluble polar aprotic organic solvent;

2) at least one alcohol solvent;

3) at least one quaternary ammonium hydroxide;

4) water;

5) at least one copper corrosion inhibitor selected from the group consisting of 6-substituted-2,4-diamino-1,3,5-triazines, the substituent at the 6-position being a substituted or unsubstituted aryl group;

6) at least one aluminum corrosion inhibitor; and

7) optionally, at least one defoaming surfactant;

wherein the at least one aluminum corrosion inhibitor comprises a compound selected from the group consisting of phosphoric acids and salts of phosphoric acids.

14. The composition of claim 13 , wherein the at least one aluminum corrosion inhibitor comprises monophosphoric acid, a polyphosphoric acid, a phosphoric anhydride, or a salt thereof.

15. A photoresist stripping composition, comprising:

1) at least one water soluble polar aprotic organic solvent;

2) at least one alcohol solvent;

3) at least one quaternary ammonium hydroxide;

4) water;

5) at least one copper corrosion inhibitor selected from the group consisting of 6-substituted-2,4-diamino-1,3,5-triazines, the substituent at the 6-position being a substituted or unsubstituted aryl group;

6) at least one aluminum corrosion inhibitor; and

7) optionally, at least one defoaming surfactant;

wherein the at least one aluminum corrosion inhibitor comprises first and second components, the first component comprising a Group II metal cation and the second component comprising an agent capable of solubilizing the Group II metal cation.

16. The composition of claim 15 , wherein the first component comprises Ca 2+ , Mg 2+ , Sr 2+ , or Ba 2+ .

17. The composition of claim 15 , wherein the agent is selected from the group consisting of 1,2,3-triazole carboxylic acid compounds substituted with a group that under basic conditions is an electron donating group, and 1,2,4-triazole carboxylic acid compounds substituted with a group that under basic conditions is an electron donating group.

18. The composition of claim 17 , wherein the electron donating group is carboxyl, mercapto, hydroxyphenyl, amino, alkylamino, or dialkylamino.

19. The composition of claim 18 , wherein the agent is 3-amino-1,2,4-triazole-5-carboxylic acid.

20. The composition of claim 12 , wherein the composition comprises from about 0.1% to about 10% of the at least one aluminum corrosion inhibitor.

21. The composition of claim 1 , wherein the composition has a pH of at least about 13.

22. A method, comprising:

contacting a semiconductor substrate containing a photoresist or a photoresist residue with a composition of claim 1 to remove the photoresist or photoresist residue.

23. The method of claim 22 , further comprising rinsing the semiconductor substrate with a rinse solvent after the contacting step.

24. The method of claim 23 , further comprising drying the semiconductor substrate after the rinsing step.

25. The method of claim 22 , wherein the method does not substantially remove Cu or Al in the semiconductor substrate.

26. A photoresist stripping composition, comprising:

1) at least one water soluble polar aprotic organic solvent in an amount of from about 30% to about 90% of the composition;

2) at least one alcohol solvent;

3) at least one quaternary ammonium hydroxide;

4) water;

5) at least one copper corrosion inhibitor selected from the group consisting of 6-substituted-2,4-diamino-1,3,5-triazines, the substituent at the 6-position being a linear or branched, substituted or unsubstituted C 2 -C 12 alkyl group, a substituted or unsubstituted C 3 -C 12 cycloalkyl group, a substituted or unsubstituted aryl group, —SCH 2 R 100 , —N(R 100 R 101 ) or imidyl, in which each of R 100 and R 101 , independently, is a linear or branched, substituted or unsubstituted C 1 -C 12 alkyl group optionally containing a nitrogen or oxygen atom in the alkyl chain, a substituted or unsubstituted C 3 -C 12 cycloalkyl group optionally containing a nitrogen or oxygen atom in the cycloalkyl ring, a substituted or unsubstituted aryl group, or R 100 and R 101 , together with the atom to which they are attached, form a ring; and

6) optionally, at least one defoaming surfactant.

27. A photoresist stripping composition, comprising:

1) at least one water soluble polar aprotic organic solvent in an amount of from about 30% to about 90% of the composition;

2) at least one alcohol solvent;

3) at least one quaternary ammonium hydroxide;

4) water;

5) at least one copper corrosion inhibitor selected from the group consisting of 6-substituted-2,4-diamino-1,3,5-triazines; and

6) optionally, at least one defoaming surfactant;

wherein the composition does not include an organic acid.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2016
From: DU, BING; DORY, THOMAS; WOJTCZAK, WILLIAM A.
To: FUJIFILM ELECTRONIC MATERIALS U.S.A., INC.
Reel/Frame 037527/0829 →
Continuity (2)
Provisional Application 62097747 · Dec 30, 2014
Related Publication 20160186106A1 · Jun 30, 2016