IP Library Granted Patent US 9,158,202
Granted Patent B2
US 9,158,202 · App. 13/834,513 · Granted Oct 13, 2015

Process and composition for removing substances from substrates

Inventors: Richard Dalton Peters (Kingsport, TN); Travis Acra (Ingalls, IN); Yuanmei Cao (Indianapolis, IN); Spencer Erich Hochstetler (Kingsport, TN); Michael Tod Phenis (Markleville, IN); Kimberly Dona Pollard (Anderson, IN)
Assignee: Dynaloy, LLC
G03F7/422C11D7/3218C11D7/3263C11D7/3281C11D11/0047G03F7/425
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Quick Facts
Patent No.
US 9,158,202
App. No.
13/834,513
Granted
Oct 13, 2015
Kind
B2
Abstract

Compositions are described that are useful for removing organic and organometallic substances from substrates, for example, photoresist wafers. Processes are presented that apply a minimum volume of a composition as a coating to the inorganic substrate whereby sufficient heat is added and the organic or organometallic substances are completely removed by rinsing. The compositions and processes may be suitable for removing and, in some instances, completely dissolving photoresists of the positive and negative varieties, and specifically negative dry film photoresist from electronic devices.

Claims (43)

1. A composition comprising:

a) from about 20 wt. % to about 90 wt. % of a polar aprotic solvent other than dimethyl sulfoxide;

b) from about 1 wt. % to about 70 wt. % of at least one alkanolamine having at least two carbon atoms, at least one amino substituent and at least one hydroxyl substituent, wherein the at least one amino substituent and the at least one hydroxyl substituent are attached to two different carbon atoms;

c) less than about 3.5 wt. % of a quaternary ammonium hydroxide;

d) optionally one or more secondary solvents, one or more corrosion inhibitors, and/or one or more surfactants; and

e) water present in an amount no greater than about 1.5 wt. %.

2. The composition according to claim 1 , wherein the polar aprotic solvent comprises dimethylformamide; dimethylacetamide; 1-formylpiperidine; dimethylsulfone; n-methylpyrrolidone; n-cyclohexyl-2-pyrrolidone; or a mixture thereof.

3. The composition of claim 1 , wherein the polar aprotic solvent is present in an amount of from about 35 wt. % to about 85 wt. %.

4. The composition of claim 3 , wherein the polar aprotic solvent is present in an amount of from about 55 wt. % to about 80 wt. %.

5. The composition according to claim 1 , wherein the at least one alkanolamine comprises aminoethylethanolamine, dimethylaminoethanol, monoethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-butylethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylisopropanolamine, N-ethylisopropanolamine, N-propylisopropanolamine, 2-aminopropane-1-ol, N-methyl-2-aminopropane-1-ol, N-ethyl-2-aminopropane-1-ol, 1-aminopropane-3-ol, N-methyl-1-aminopropane-3-ol, N-ethyl-1-aminopropane-3-ol, 1-aminobutane-2-ol, N-methyl-1-aminobutane-2-ol, N-ethyl-1-aminobutane-2-ol, 2-aminobutane-1-ol, N-methyl-2-aminobutane-1-ol, N-ethyl-2-aminobutane-1-ol, 3-aminobutane-1-ol, N-methyl-3-aminobutane-1-ol, N-ethyl-3-aminobutane-1-ol, 1-aminobutane-4-ol, N-methyl-1-aminobutane-4-ol, N-ethyl-4-ol, 1-amino-2-methylpropane-2-ol, 2-amino-2-methylpropane-1-ol, 1-aminopentane-4-ol, 2-amino-4-methylpentane-1-ol, 2-aminohexane-1-ol, 3-aminoheptane-4-ol, 1-aminooctane-2-ol, 5-aminooctane-4-ol, 1-aminopropane-2,3-diol, 2-aminopropane-1,3-diol, tris(oxymethyl)aminomethane, 1,2-diaminopropane-3-ol, 1,3-diaminopropane-2-ol, 2-(2-aminoethoxy)ethanol or a mixture thereof.

6. The composition according to claim 5 , wherein the at least one alkanolamine comprises dimethylaminoethanol.

7. The composition according to claim 1 , wherein the at least one alkanolamine is present in an amount of less than 20 wt. %.

8. The composition according to claim 7 , wherein the at least one alkanolamine is present in an amount of less than 10 wt. %.

9. The composition according to claim 8 , wherein the at least one alkanolamine is present in an amount of less than 5 wt. %.

10. The composition according claim 1 , wherein the quaternary ammonium hydroxide comprises tetramethylammonium hydroxide; tetramethylammonium hydroxide pentahydrate; tetrabutylammonium hydroxide; benzyltrimethylammonium hydroxide; tetrapropylammonium; dimethyldipropylammonium hydroxide; tetraethyl ammonium hydroxide; dimethyldiethyl ammonium hydroxide or a mixture thereof.

11. The composition according to claim 1 wherein the quaternary ammonium hydroxide is present in an amount less than 3 wt. %.

12. The composition according to claim 1 , wherein the quaternary ammonium hydroxide is present in an amount of less than 2.5 wt. %.

13. The composition according to claim 1 , wherein the quaternary ammonium hydroxide is present in an amount of less than 2.0 wt. %.

14. The composition according to claim 1 , comprising one or more surfactants, one or more secondary solvents, and/or one or more metal corrosion inhibitors.

15. The composition according to claim 1 , comprising one or more surfactants and one or more secondary solvents.

16. A composition comprising:

a) from about 20 wt. % to about 90 wt. % of a polar aprotic solvent;

b) a first alkanolamine present in an amount less than about 20 wt. %, the first alkanolamine having at least two carbon atoms, at least one amino substituent and at least one hydroxyl substituent, wherein the at least one amino substituent and the at least one hydroxyl substituent are attached to two different carbon atoms;

c) from about 15 wt. % to about 60 wt. % of a second alkanolamine having at least two carbon atoms, at least one amino substituent and at least one hydroxyl substituent, wherein the at least one amino substituent and the at least one hydroxyl substituent are attached to two different carbon atoms;

d) optionally one or more secondary solvents, one or more corrosion inhibitors, and/or one or more surfactants; and

e) a balance in water.

17. The composition according to claim 16 , wherein the polar aprotic solvent comprises dimethyl sulfoxide; dimethylformamide; dimethylacetamide; 1-formylpiperidine; dimethylsulfone; n-methylpyrrolidone; n-cyclohexyl-2-pyrrolidone or a mixture thereof.

18. The composition according to claim 16 , wherein the polar aprotic solvent comprises dimethyl sulfoxide.

19. The composition of claim 16 , wherein the polar aprotic solvent is present in an amount of from about 35 wt. % to about 85 wt. %.

20. The composition of claim 19 , wherein the polar aprotic solvent is present in an amount of from about 55 wt. % to about 80 wt. %.

21. The composition according to claim 16 , wherein the first alkanolamine and the second alkanolamine each independently comprise aminoethylethanolamine, dimethylaminoethanol, monoethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-butylethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, N-methylisopropanolamine, N-ethylisopropanolamine, N-propylisopropanolamine, 2-aminopropane-1-ol, N-methyl-2-aminopropane-1-ol, N-ethyl-2-aminopropane-1-ol, 1-aminopropane-3-ol, N-methyl-1-aminopropane-3-01, N-ethyl-1-aminopropane-3-ol, 1-aminobutane-2-ol, N-methyl-1-aminobutane-2-ol, N-ethyl-1-aminobutane-2-ol, 2-aminobutane-1-ol, N-methyl-2-aminobutane-1-ol, N-ethyl-2-aminobutane-1-ol, 3-aminobutane-1-ol, N-methyl-3-aminobutane-1-ol, N-ethyl-3-aminobutane-1-ol, 1-aminobutane-4-ol, N-methyl-1-aminobutane-4-ol, N-ethyl-1-aminobutane-4-ol, 1-amino-2-methylpropane-2-ol, 2-amino-2-methylpropane-1-ol, 1-aminopentane-4-ol, 2-amino-4-methylpentane-1-ol, 2-aminohexane-1-ol, 3-aminoheptane-4-ol, 1-aminooctane-2-ol, 5-aminooctane-4-ol, 1-aminopropane-2,3-diol, 2-aminopropane-1,3-diol, tris(oxymethyl)aminomethane, 1,2-diaminopropane-3-ol, 1,3-diaminopropane-2-ol, 2-(2-aminoethoxy)ethanol or a mixture thereof.

22. The composition according to claim 16 , comprising one or more surfactants, one or more secondary solvents, and/or one or more metal corrosion inhibitors.

23. The composition according to claim 16 , wherein said polar aprotic solvent is present in an amount effective for removing a photoresist or post plasma processed photoresist residue from a substrate.

24. The composition according to claim 1 , comprising one or more secondary solvents, said one or more secondary solvents comprising propylene glycol.

25. The composition according to claim 16 , comprising one or more secondary solvents, said one or more secondary solvents comprising propylene glycol.

26. The composition according to claim 1 , wherein said composition comprises a secondary solvent, said secondary solvent comprising at least one of ethylene glycol, diethylene glycol, propylene glycol, dipropyleneglycol, isopropylene glycol, diisopropylene glycol, butylene glycol, dibutylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropylether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monoisobutyl ether, diethylene glycol monobenzyl ether, diethylene glycol diethyl ether, triethylene glycol monomethyl ether, triethylene glycol dimethyl ether, polyethylene glycol monomethyl ether, diethylene glycol methyl ethyl ether, triethylene glycol, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl acetate, propylene glycol monomethyl ether, propylene glycol dimethyl ether, propylene glycol monobutyl ether, dipropyelene glycol monomethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol dipropyl ether, dipropylene glycol diisopropyl ether, tripropylene glycol and tripropylene glycol monomethyl ether, 1-methoxy-2-butanol, 2-methoxy-1-butanol, 2-methoxy-2-methyl-2-butanol, dioxane, trioxane, 1,1-dimethoxyethane, tetrahydrofuran, or crown ethers.

27. A composition comprising:

from about 20 wt. % to about 90 wt. % of a polar aprotic solvent;

a first alkanolamine present in an amount less than about 20 wt. %;

a second alkanolamine present in an amount of at least about 40 wt. %;

optionally one or more secondary solvents, one or more corrosion inhibitors, and/or one or more surfactants; and

water present in an amount less than about 5 wt. %.

28. The composition according to claim 27 , wherein the polar aprotic solvent is present in an amount of at least about 20 wt. % to no greater than about 40 wt. %.

Assignments (3)
PATENT ASSIGNMENT EFFECTIVE JULY 11, 2017 Recorded Jan 24, 2018
From: DYNALOY, LLC
To: VERSUM MATERIALS US, LLC
Reel/Frame 045140/0008 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME. RECORDED AT REEL/FRAME 030219/0858, AND ALSO REEL/FRAME 030219/0862. (*700503775*) PREVIOUSLY RECORDED ON REEL 030219 FRAME 0862. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME WAS AN ERROR. Recorded Aug 8, 2014
From: PETERS, RICHARD DALTON; ACRA, TRAVIS; CAO, YUANMEI; HOCHSTETLER, SPENCER ERICH; PHENIS, MICHAEL TOD; POLLARD, KIMBERLY DONA
To: DYNALOY, LLC
Reel/Frame 033500/0621 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2013
From: PETERS, RICHARD DALTON; ACRA, TRAVIS; CAO, YUANMEI; HOCHSTETLER, SPENCER ERICH; PHENIS, MICHAEL TOD; POLLARD, KIMBERLY DONA
To: DYNALOY, LLC
Reel/Frame 030219/0862 →
Continuity (2)
Provisional Application 61728905 · Nov 21, 2012
Related Publication 20140142017A1 · May 22, 2014