Redox reagent-containing post-etch residue cleaning composition

• US 5,612,304 A
• Filed: 07/07/1995
• Issued: 03/18/1997
• Est. Priority Date: 07/07/1995
• Status: Expired due to Fees

• Current Assignee: OCG Microelectronic Materials Incorporated
• Original Assignee: OLIN Microelectronic Chemicals Incorporated
• Inventors: Honda, Kenji, Hurditch, Rodney
• Primary Examiner(s): Tierney, Michael
• Application Number:
  US08/499,355
• Time in Patent Office: 620 Days
• Field of Search: 252/546, 252/548, 252/153, 430/331, 430/256, 430/258, 510/176, 510/175, 510/490, 510/500, 510/493
• US Class Current: 510/176
• CPC Class Codes: C11D 3/0073 Anticorrosion compositions
• CPC Class Codes: C11D 7/261 Alcohols; Phenols
• CPC Class Codes: C11D 7/268 Carbohydrates or derivatives thereof
• CPC Class Codes: C11D 7/32 containing nitrogen
• CPC Class Codes: C11D 7/3209 Amines or imines with one to four nitrogen atoms; Quaternized amines
• CPC Class Codes: C11D 7/3218 Alkanolamines or alkanolimines
• CPC Class Codes: C11D 7/3245 Aminoacids
• CPC Class Codes: C11D 7/3281 Heterocyclic compounds
• CPC Class Codes: C11D 7/34 containing sulfur
• CPC Class Codes: C11D 7/5009 containing phosphorus, sulfur or silicon, e.g. dimethylsulfoxide
• CPC Class Codes: C11D 7/5013 containing nitrogen
• CPC Class Codes: G03F 7/425 containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
• CPC Class Codes: H01L 21/31058 of organic layers

Abstract

A noncorrosive post-etch residue cleaning composition containing:

(a) 1-70% by weight of an organic polar solvent having a dipole moment of more than 3.5;

(b) 1-70% by weight of selected amine compounds having at least one hydroxyl group and a boiling point higher than 150° C. at atmospheric pressure;

(c) 0.1-10% by weight of selected amino acid having at least one hydroxyl group;

(d) 1-20% by weight of selected redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE (at pH=7); and

(e) 0-90% by weight of water.

Claims

1. A post-etch residue cleaner composition, comprising:

(a) from about 1 to about 70% by weight of an organic polar solvent having a dipole moment of more than 3.5;

(b) from about 1 to about 70% by weight of an alkanolamine compound having a boiling point higher than 150°

C. at atmospheric pressure;

(c) from about 0.1 to about 10% by weight of an amino acid selected from the group consisting of compounds having the formula (I);

##STR4## wherein p is an integer ranging from 1-3;

R¹ and R² are each independently selected from the group consisting of hydrogen and compounds having the formula (II);

##STR5## wherein R⁵, R⁶, and R⁷ are each independently selected from hydrogen, --OH, --CH₂ OH, alkyl, alkoxy, phenyl, and mono-, di- or tri-hydroxy-substituted phenyl groups; and

R³ and R⁴ are each independently selected from the group consisting of hydroxy and compounds having the formula (III);

##STR6## wherein X'"'"', Y'"'"', and Z'"'"' are each independently selected from hydrogen, --OH, --CH₂ OH, --CH₂ CH₂ OH, alkyl, or alkoxy group, and at least one of them is --OH, --CH₂ OH or --CH₂ CH₂ OH;

(d) from about 1 to about 20% by weight of a redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE (at pH=7) selected from the group consisting of sugar alcohols, piperidine, aniline, o-phenylenediamine, hydrazine, 1,10-phenanthroline and benzidine; and

(e) optionally, from about 0% to about 90% by weight of water;

all percents based on the total weight of the cleaner composition.

2. The cleaner composition of claim 1, wherein said solvent (a) comprises a cyclic amide.

3. The cleaner composition of claim 2, wherein said cyclic amide is selected from the group consisting of N-alkyl-2-pyrrolidones and 1,3-dialkyl-2-imidazolidinones.

4. The cleaner composition of claim 2, wherein said solvent (a) is an admixture of N-hydroxyethyl-pyrrolididone (HEP) with 1,3-dimethyl-2-imidozolidinone (DMI) wherein the ratio of HEP:

DMI is from about 95;

5% to about 5;

95% by weight.

5. The cleaner composition of claim 1, wherein said solvent (a) comprises dimethylsulfoxide.

6. The cleaner composition of claim 1, wherein said solvent (a) is an admixture of N-hydroxyethyl-pyrrolididone (HEP) with dimethylsulfoxide (DMSO) wherein the ratio of HEP:

DMSO is from 95;

5% to about 5.95% by weight.

7. The cleaner composition of claim 12, wherein said alkanolamine is selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, 2-(2-aminoethoxy)ethanol and 2-(2-aminoethylamino)ethanol.

8. The cleaner composition of claim 1, wherein said redox reagent (d) is a sugar alcohol.

9. The cleaner composition of claim 8, wherein said sugar alcohol is selected from the group consisting of erythritols, penitols, and hexitols.

10. The cleaner composition of claim 9, wherein said sugar alcohol is a penitol and is selected from the group consisting of D-arabitol and D-xylitol.

11. The cleaner composition of claim 9, wherein said sugar alcohol is a hexitol and is selected from the group consisting of D-sorbitol and D-mannitol.

12. The cleaner composition of claim 1, wherein said redox reagent (d) is piperidine.

13. The cleaner composition of claim 1, wherein said redox reagent (d) is aniline.

14. The cleaner composition of claim 1, wherein said redox reagent (d) is o-phenylenediamine.

15. The cleaner composition of claim 1, wherein said redox reagent (d) is hydrazine.

16. The cleaner composition of claim 1, wherein said redox reagent (d) is 1,10-phenanthroline.

17. The cleaner composition of claim 1, wherein said redox reagent (d) is benzidine.

18. The cleaner composition of claim 1, wherein said redox reagent (d) is present from about 3% to about 10% by weight, based on the total weight of said cleaner composition.

19. The cleaner composition of claim 1, wherein said amino acid (c) is selected from the group consisting of tricine, bicine, DL-homoserine, D-homoserine, L-homoserine, DL-threonine, D-allo-threonine, L-allo-threonine, D-threonine, L-threonine, DL-3-hydroxy-norvaline, DL-methyltyrosine, D-4-hydroxyphenylglycine, DL-tyrosine, D-tyrosine, L-tyrosine, 3-(3,4-dihydroxyphenyl)-DL-alanine, 3-(3,4-dihydroxyphenyl)-L-alanine, 3-(2,4,5-trihydroxyphenyl)-DL-alanine, DL-alphamethyltyrosine, L-alpha-methyltyrosine, (--)-3-(3,4-dihydroxyphenyl)-2-methyl-L-alanine, DL-threo-3-phenylserine, and DL-threo-3,4-dihydroxyphenylserine.

20. The cleaner composition of claim 18, wherein said amino acid is selected from the group consisting of tricine, bicine, 3-(3,4-dihydroxyphenyl)-DL-alanine, 3-(2,4,5-trihydroxyphenyl)-DL-alanine, and DL-threo-3,4-dihydroxyphenylserine.

21. The cleaner composition of claim 1, wherein said cleaner composition further comprises water.