Granted Patent B2

US 8,338,087 · App. 10/792,038 · Granted Dec 25, 2012

Abstract

Claims (476)

1. A cleaning composition comprising a quaternary base, at least one alkali or alkaline earth base, and at least one additional component selected from the group consisting of a chelator, an oxirane species, and combinations thereof, wherein said chelator comprises a species selected from the group consisting of: 1-amino-1,2,4-triazole; 1-amino-1,2,3-triazole; 1-amino-5-methyl-1,2,3-triazole; 3-mercapto-1,2,4-triazole; 3-isopropyl-1,2,4-triazole; naphthotriazole; 2-mercaptobenzimidazole; 5-aminotetrazole; 5-amino-1,3,4-thiadiazole-2-thiol; 2,4-diamino-6-methyl-1,3,5-triazine; triazine; methyltetrazole; 1,5-pentamethylenetetrazole; 1-phenyl-5-mercaptotetrazole; diaminomethyltriazine; imidazoline thione; 4-methyl-4H-1,2,4-triazole-3-thiol; 5-amino-1,3,4-thiadiazole-2-thiol; tritolyl phosphate; indiazole; adenine; salicylamide; iminodiacetic acid; benzoguanamine; thiocyranuric acid; anthranilic acid; 3-mercaptopropanol; and combinations thereof, and wherein the oxirane species comprises a species selected from the group consisting of: oxirane, methyl-, polymer with oxirane, ether with 2,2′-(oxidoimino)bis(ethanol) (2:1), N(-3(C9-11-isoalkyloxy)propyl)derivatives, C 10 -rich; and oxirane, methyl-, polymer with oxirane, mono(octylphenyl)ether.

2. The cleaning composition of claim 1 , which is devoid of hydroxylamine therein.

3. The cleaning composition of claim 1 , comprising the following components:

0.1-40.0 weight % organic quaternary base;

0.01-5 weight % alkali or alkaline earth base;

0-80 weight % solvent(s) and/or amine(s);

0-5 weight % surfactant;

0-10 weight % chelator/passivation agent; and

0-98 weight % water,

wherein percentages of the components are percentages by weight, based on total weight of the composition, and wherein the total of the weight percentages of such components of the composition does not exceed 100 weight %.

4. The cleaning composition of claim 1 , including at least one additional ingredient selected from the group consisting of stabilizers, dispersants, anti-oxidants, fillers, penetration agents, adjuvants, additives, and excipients.

5. The cleaning composition of claim 1 , comprising the following components:

2-15 weight % organic quaternary base;

˜0.01-2 weight % alkali or alkaline earth base;

0-50 weight % solvent(s) and/or amine(s);

˜0.01-2 weight % surfactant;

0-5 weight % chelator/passivation agent; and

40-95 weight % water,

wherein percentages of the components are percentages by weight, based on total weight of the composition, and wherein the total of the weight percentages of such components of the composition does not exceed 100 weight %.

6. The cleaning composition of claim 1 , selected from the group consisting of Formulations A-C 2 , wherein all percentages are by weight, based on the total weight of the formulation:

Formulation A

5.36%

benzyltrimethylammonium hydroxide

0.28%

potassium hydroxide

 3.0%

4-methylmorpholine N-oxide

0.30%

polyoxyethylene (150) dinonylphenyl ether

0.08%

2-mercaptobenzimidazole

91.0%

water

Formulation B

 5.36%

benzyltrimethylammonium hydroxide

 0.28%

potassium hydroxide

 3.0%

4-methylmorpholine N-oxide

 0.30%

polyoxyethylene (150) dinonylphenyl ether

 0.20%

5-amino-1,3,4-thiadiazole-2-thiol

90.86%

water

Formulation C

 3.60%

benzyltrimethylammonium hydroxide

 0.27%

potassium hydroxide

 3.5%

4-methylmorpholine N-oxide

 15.0%

4-(3-aminopropyl)morpholine

 0.30%

polyoxyethylene (150) dinonylphenyl ether

 0.08%

2-mercaptobenzimidazole

77.25%

water

Formulation D

 5.36%

benzyltrimethylammonium hydroxide

 0.28%

potassium hydroxide

 20.0%

dimethyl sulfoxide

 0.08%

2-mercaptobenzimidazole

74.28%

water

Formulation E

 5.36%

benzyltrimethylammonium hydroxide

 0.28%

potassium hydroxide

 10.0%

tetramethylene sulfone

 0.30%

oxirane, methyl-, polymer with oxirane,

ether with 2,2′-(oxidoimino)bis(ethanol) (2:1), N(-

3(C9-11-isoalkyloxy)propyl) derivatives, C 10 -rich

 0.08%

2-mercaptobenzimidazole

83.98%

water

Formulation F

 5.36%

benzyltrimethylammonium hydroxide

 0.28%

potassium hydroxide

 10.0%

di(ethyleneglycol)butyl ether

 10.0%

2-(2-dimethylamino)ethoxy)ethanol

 0.30%

oxirane, methyl-, polymer with oxirane,

ether with 2,2′-(oxidoimino)bis(ethanol) (2:1), N(-

3(C9-11-isoalkyloxy)propyl) derivatives, C 10 -rich

74.06%

water

Formulation G

 5.36%

benzyltrimethylammonium hydroxide

 0.28%

potassium hydroxide

 10.0%

tetramethylene sulfone

 10.0%

di(ethyleneglycol)butyl ether

 0.10%

oxirane, methyl-, polymer with oxirane, mono(octylphenyl)ether

 0.08%

2-mercaptobenzimidazole

74.18%

water,

Formulation H

benzyltrimethylammonium hydroxide, 40% aqueous solution

 9.0%

potassium hydroxide, 45% aqueous solution

 0.6%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

dinonylphenol ethoxylate, 7% aqueous solution

 4.3%

2-mercaptobenzimidazole

 0.1%

aminopropylmorpholine

 20.0%

water

59.02%

Formulation I

benzyltrimethylammonium hydroxide, 40% aqueous solution

 9.0%

potassium hydroxide, 45% aqueous solution

 0.6%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

dinonylphenol ethoxylate, 7% aqueous solution

 4.3%

2-mercaptobenzimidazole

 0.1%

aminopropylmorpholine

 15.0%

water

64.02%

Formulation J

benzyltrimethylammonium hydroxide, 40% aqueous solution

 9.0%

potassium hydroxide, 45% aqueous solution

 0.6%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

dinonylphenol ethoxylate, 7% aqueous solution

 4.3%

2-mercaptobenzimidazole

 0.1%

aminopropylmorpholine

 10.0%

water

69.02%

Formulation K

benzyltrimethylammonium hydroxide, 40% aqueous solution

 13.4%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 0.6%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

78.62%

Formulation L

benzyltrimethylammonium hydroxide, 40% aqueous solution

 13.4%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 1.2%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

78.02%

Formulation M

tetramethylammonium hydroxide, 25% aqueous solution

 5.85%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 1.2%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

85.57%

Formulation N

tetramethylammonium hydroxide, 25% aqueous solution

 2.93%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 1.2%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

88.49%

Formulation O

benzyltrimethylammonium hydroxide, 40% aqueous solution

 7.2%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 0.6%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

84.82%

Formulation P

benzyltrimethylammonium hydroxide, 40% aqueous solution

 3.6%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 1.2%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

87.82%

Formulation Q

benzyltrimethylammonium hydroxide, 40% aqueous solution

 3.6%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 0.6%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

88.42%

Formulation R

benzyltrimethylammonium hydroxide, 40% aqueous solution

 7.2%

N-methylmorpholine oxide, 50% aqueous solution

 7.0%

KOH, 45% aqueous solution

 0.3%

2-mercaptobenzimidizole

 0.08%

dinonylphenol polyoxyethylene

 0.3%

water

85.12%,

Formulation S

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

3-amino-5-mercapto-1,2,4-triazole

 1.0%

water

72.04%

Formulation T

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

4-methyl-2-phenyl-imidazole

 1.0%

water

72.04%

Formulation U

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

2-mercaptothiazoline

 1.0%

water

72.04%

Formulation V

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

8-hydroxyquinoline

 1.0%

water

72.04%

Formulation W

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

1-phenyl-2-tetrazoline-5-thione

 1.0%

water

72.04%

Formulation X

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

gallic acid

 1.0%

water

72.04%

Formulation Y

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

salicylic acid

 1.0%

water

72.04%

Formulation Z

benzyltrimethylammonium hydroxide, 40% aqueous solution

22.26%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

methyldiethanolamine

 2.33%

phosphoric acid (86%)

 1.69%

ascorbic acid

 1.0%

water

72.04%

Formulation A 2

benzyltrimethylammonium hydroxide, 40% aqueous solution

 7.2%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

aminopropyl morpholine

  10%

4-methyl-2-phenyl-imidazole

 1.0%

water

81.12%

Formulation B 2

benzyltrimethylammonium hydroxide, 40% aqueous solution

 7.2%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

aminopropyl morpholine

  10%

4-methyl-2-phenyl-imidazole

 0.5%

water

81.62%

Formulation C 2

benzyltrimethylammonium hydroxide, 40% aqueous solution

 7.2%

Potassium hydroxide, 45% aqueous solution

 0.6%

2-mercaptobenzimidazole

 0.08%

aminopropyl morpholine

  10%

4-methyl-2-phenyl-imidazole

 1.0%

water

81.02%

dinonylphenol polyoxyethylene

 0.1%.

7. The cleaning composition of claim 1 , wherein the alkali base comprises potassium hydroxide.

8. The cleaning composition of claim 1 , wherein the chelator comprises 2-mercaptobenzimidazole.

9. The cleaning composition of claim 1 , wherein the chelator is present in an amount greater than about 0.08 wt. %, based on the total weight of the composition.

10. The composition of claim 1 , further comprising a surfactant.

11. The composition of claim 10 , wherein the surfactant comprises a surfactant species selected from the group consisting of: fluoroalkyl surfactants; polyethylene glycols; polypropylene glycols; polyethylene glycol ethers; polypropylene glycol ethers; carboxylic acid salts; dodecylbenzenesulfonic acid and salts thereof; polyacrylate polymers; dinonylphenyl polyoxyethylene; silicone polymers; modified silicone polymers; acetylenic diols; modified acetylenic diols, alkylammonium salts; modified alkylammonium salts; and combinations of two or more of the foregoing.

12. The composition of claim 1 , further comprising a co-solvent.

13. The composition of claim 12 , wherein the co-solvent comprises a co-solvent species selected from the group consisting of: amines; glycols; glycol ethers; polyglycol ethers; and combinations of two or more of the foregoing.

14. The composition of claim 12 , wherein the co-solvent comprises a co-solvent species selected from the group consisting of: dimethyldiglycolamine; 1,8-diazabicyclo[5.4.0]undecene; aminopropylmorpholine; triethanolamine; methylethanolamine; diethylene glycol; propylene glycol; neopentyl glycol; hydroxyethylmorpholine; aminopropylmorpholine; di(ethylene glycol)monoethyl ether; di(propylene glycol)propyl ether; ethylene glycol phenyl ether; di(propylene glycol) butyl ether; butyl carbitol; polyglycol ethers; and combinations of two or more of the foregoing.

15. A method of removing photoresist and/or SARC material from a substrate having said material thereon, said method comprising contacting the substrate with a cleaning composition for sufficient time to at least partially remove said material from the substrate, wherein the cleaning composition comprises a quaternary base, at least one alkali or alkaline earth base, and at least one additional component selected from the group consisting of a chelator, an oxirane species, and combinations thereof, wherein said chelator comprises a species selected from the group consisting of: 1-amino-1,2,4-triazole; 1-amino-1,2,3-triazole; 1-amino-5-methyl-1,2,3-triazole; 3-mercapto-1,2,4-triazole; 3-isopropyl-1,2,4-triazole; naphthotriazole; 2-mercaptobenzimidazole; 5-aminotetrazole; 5-amino-1,3,4-thiadiazole-2-thiol; 2,4-diamino-6-methyl-1,3,5-triazine; triazine; methyltetrazole; 1,5-pentamethylenetetrazole; 1-phenyl-5-mercaptotetrazole; diaminomethyltriazine; imidazoline thione; 4-methyl-4H-1,2,4-triazole-3-thiol; 5-amino-1,3,4-thiadiazole-2-thiol; tritolyl phosphate; indiazole; adenine; salicylamide; iminodiacetic acid; benzoguanamine; thiocyranuric acid; anthranilic acid; 3-mercaptopropanol; and combinations thereof, and wherein the oxirane species comprises a species selected from the group consisting of: oxirane, methyl-, polymer with oxirane, ether with 2,2′-(oxidoimino)bis(ethanol) (2:1), N(-3(C9-11-isoalkyloxy)propyl)derivatives, C 10 -rich; and oxirane, methyl-, polymer with oxirane, mono(octylphenyl)ether.

16. The method of claim 15 , wherein the substrate comprises a semiconductor device structure.

17. The method of claim 15 , wherein the material comprises photoresist.

18. The method of claim 15 , wherein the material comprises SARC material.

19. The method of claim 18 , wherein the SARC material has been applied to a semiconductor device structure to minimize reflectivity variations during photolithographic patterning on the semiconductor device structure.

20. The method of claim 15 , wherein said contacting is carried out for a time of from about 10 to about 45 minutes.

21. The method of claim 15 , wherein said contacting is carried out at temperature in a range of from about 50° C. to about 80° C.

22. The method of claim 15 , wherein the composition is devoid of hydroxylamine therein.

23. The method of claim 15 , wherein the composition comprises the following components:

0.1-40.0 weight % organic quaternary base;

0.01-5 weight % alkali or alkaline earth base;

0-80 weight % solvent(s) and/or amine(s);

0-5 weight % surfactant;

0-10 weight % chelator/passivation agent; and

0-98 weight % water,

wherein percentages of the components are percentages by weight, based on total weight of the composition, and wherein the total of the weight percentages of such components of the composition does not exceed 100 weight %.

24. The method of claim 15 , wherein the composition includes at least one additional ingredient selected from the group consisting of stabilizers, dispersants, anti-oxidants, fillers, penetration agents, adjuvants, additives, fillers, and excipients.

25. The method of claim 15 , wherein the composition comprises the following components:

2-15 weight % organic quaternary base;

˜0.01-2 weight % alkali or alkaline earth base;

0-50 weight % solvent(s) and/or amine(s);

˜0.01-2 weight % surfactant;

0-5 weight % chelator/passivation agent; and

40-95 weight % water,

wherein percentages of the components are percentages by weight, based on total weight of the composition, and wherein the total of the weight percentages of such components of the composition does not exceed 100 weight %.

26. The method of claim 15 , wherein the alkali base comprises potassium hydroxide.

27. The method of claim 15 , wherein the chelator comprises 2-mercaptobenzimidazole.

28. The method of claim 27 , wherein the chelator is present in an amount greater than about 0.08 wt. %, based on the total weight of the composition.

29. The method of claim 15 , wherein the quaternary base comprises benzyltrimethylammonium hydroxide.

30. The method of claim 15 , wherein the cleaning composition further comprises a surfactant.

31. The method of claim 30 , wherein the surfactant comprises a surfactant species selected from the group consisting of: fluoroalkyl surfactants; polyethylene glycols; polypropylene glycols; polyethylene glycol ethers; polypropylene glycol ethers; carboxylic acid salts; dodecylbenzenesulfonic acid and salts thereof; polyacrylate polymers; dinonylphenyl polyoxyethylene; silicone polymers; modified silicone polymers; acetylenic diols; modified acetylenic diols, alkylammonium salts; modified alkylammonium salts; and combinations of two or more of the foregoing.

32. The method of claim 15 , wherein the cleaning composition further comprises a co-solvent.

33. The method of claim 32 , wherein the co-solvent comprises a co-solvent species selected from the group consisting of: amines; glycols; glycol ethers; polyglycol ethers; and combinations of two or more of the foregoing.

34. The method of claim 32 , wherein the co-solvent comprises a co-solvent species selected from the group consisting of: dimethyldiglycolamine; 1,8-diazabicyclo[5.4.0]undecene; aminopropylmorpholine; triethanolamine; methylethanolamine; diethylene glycol; propylene glycol; neopentyl glycol; hydroxyethylmorpholine; aminopropylmorpholine; di(ethylene glycol)monoethyl ether; di(propylene glycol)propyl ether; ethylene glycol phenyl ether; di(propylene glycol) butyl ether; butyl carbitol; polyglycol ethers; and combinations of two or more of the foregoing.

35. The cleaning composition of claim 1 , wherein the quaternary base comprises an organic quaternary ammonium base.

36. The cleaning composition of claim 1 , wherein the quaternary base comprises benzyltrimethylammonium hydroxide.

37. The cleaning composition of claim 1 , wherein the cleaning composition comprises benzyltrimethylammonium hydroxide and potassium hydroxide.

38. The cleaning composition of claim 12 , wherein the co-solvent comprises a glycol ether.

39. The cleaning composition of claim 1 comprising benzyltrimethylammonium hydroxide; potassium hydroxide; tetramethylene sulfone; di(ethyleneglycol)butyl ether; oxirane, methyl-, polymer with oxirane, mono(octylphenyl)ether; 2-mercaptobenzimidazole; and water.

40. A method of making a semiconductor device comprising contacting the substrate with the cleaning composition of claim 1 for sufficient time to at least partially remove said material from the substrate.

41. The cleaning composition of claim 1 , further comprising oxidant.

Assignments (9)