IP Library Granted Patent US 8,293,694
Granted Patent B2
US 8,293,694 · App. 12/581,843 · Granted Oct 23, 2012

Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrate

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Quick Facts
Patent No.
US 8,293,694
App. No.
12/581,843
Granted
Oct 23, 2012
Kind
B2
Abstract

A semiconductor wafer cleaning formulation, including 1-35% wt. fluoride source, 20-60% wt. organic amine(s), 0.1-40% wt. nitrogenous component, e.g., a nitrogen-containing carboxylic acid or an imine, 20-50% wt. water, and 0-21% wt. metal chelating agent(s). The formulations are useful to remove residue from wafers following a resist plasma ashing step, such as inorganic residue from semiconductor wafers containing delicate copper interconnecting structures.

Claims (72)

1. A method of making an integrated circuit containing a copper containing substrate, comprising contacting said substrate with a wafer cleaning formulation, wherein said wafer cleaning formulation comprises at least one amine and a nitrogen-containing carboxylic acid or an imine selected from the group consisting of:

iminodiacetic acid (IDA),

glycine,

1,1,3,3-tetramethylguanidine (TMG),

CH 3 C(═NCH 2 CH 2 OH)CH 2 C(O)N(CH 3 ) 2 ,

CH 3 C(═NCH 2 CH 2 OCH 2 CH 2 OH)CH 2 C(O)N(CH 3 ) 2 ,

CH 3 C(═NH)CH 2 C(O)CH 3 ,

(CH 3 CH 2 ) 2 NC(═NH)N(CH 3 CH 2 ) 2 ,

HOOCCH 2 N(CH 3 ) 2 , and

HOOCCH 2 N(CH 3 )CH 2 COOH.

2. The method of claim 1 , wherein the wafer cleaning composition has a pH greater than 7.

3. The method of claim 1 , wherein the amount of nitrogen-containing carboxylic acid or imine is 0.1-40 weight percent, based on the total weight of the composition.

4. The method of claim 1 , wherein the wafer cleaning composition further comprises a fluoride source.

5. The method of claim 4 , wherein the fluoride source comprises a fluoride species selected from the group consisting of:

ammonium bifluoride,

ammonium fluoride,

triethanolammonium fluoride (TEAF),

diglycolammonium fluoride (DGAF),

tetramethylammonium fluoride (TMAF),

methyldiethanolammonium fluoride (MDEAF), and

triethylamine tris(hydrogen fluoride) (TREAT-HF).

6. The method of claim 4 , wherein the amount of fluoride source is 1-35% weight percent, based on the total weight of the composition.

7. The method of claim 1 , wherein the organic amine(s) comprise an amine(s) selected from the group consisting of:

diglycolamine (DGA),

methyldiethanolamine (MDEA),

pentamethyldiethylenetriamine (PMDETA),

triethanolamine (TEA),

triethylenediamine (TEDA),

hexamethylenetetramine,

3,3-iminobis(N,N-dimethylpropylamine),

monoethanolamine,

2-(methylamino)ethanol,

4-(2-hydroxyethyl)morpholine,

4-(3-aminopropyl)morpholine, and

N,N-dimethyl-2-(2-aminoethoxy)ethanol.

8. The method of claim 1 , wherein the amount of organic amine(s) is 20-60% weight percent, based on the total weight of the composition.

9. The method of claim 1 , wherein the wafer cleaning formulation further comprises water.

10. The method of claim 9 , wherein the amount of water is 20-50% weight percent, based on the total weight of the composition.

11. The method of claim 1 , wherein the wafer cleaning formulation further comprises at least one metal chelating agent selected from the group consisting of:

acetoacetamide,

ammonium carbamate,

ammonium pyrrolidinedithiocarbamate (APDC),

dimethyl malonate,

methyl acetoacetate,

N-methyl acetoacetamide,

2,4-pentanedione,

1,1,1,5,5,5-hexafluoro-2,4-pentanedione H(hfac),

2,2,6,6-tetrammethyl-3,5-heptanedione H(thd),

tetramethylammonium thiobenzoate,

tetramethylammonium trifluoroacetate,

tetramethylthiuram disulfide (TMTDS),

trifluoracetic acid,

lactic acid,

ammonium lactate,

malonic acid,

formic acid,

acetic acid,

propionic acid,

gamma-butyrolactone,

iminodiacetic acid,

methyldiethanolammonium trifluoroacetate, and

trifluoroacetic acid.

12. The method of claim 11 , wherein the amount of at least one metal chelating agent is 0-21% weight percent, based on the total weight of the composition.

13. The method of claim 4 , wherein said fluoride source comprises a compound having the general formula R 1 R 2 R 3 R 4 NF in which each of the R groups is independently selected from hydrogen atoms, C 1 -C 8 alkyl, aryl and alkenyl groups, and wherein said formulation includes a metal chelating agent of the formula:

X—CHR—Y

in which R is either hydrogen, C 1 -C 8 alkyl, aryl or alkenyl group and X and Y are functional groups containing multiply bonded moieties having electron-withdrawing properties.

14. The method of claim 13 , wherein each of X and Y is independently selected from CONH 2 , CONHR′, CN, NO 2 , SOR′, and SO 2 Z in which R′ is C 1 -C 8 alkyl and Z is hydrogen, halo, or C 1 -C 8 alkyl.

15. The method of claim 4 , wherein said fluoride source comprises a compound having the formula R 1 R 2 R 3 R 4 NF in which each of the R groups is hydrogen, C 1 -C 8 alkyl, aryl or alkenyl groups, and wherein said formulation includes a metal chelating agent of the formula, R 1 R 2 R 3 R 4 N +− O 2 CCF 3 in which each of the R groups is independently hydrogen, C 1 -C 8 alkyl, aryl or alkenyl groups.

16. The method of claim 1 , wherein the substrate comprises copper.

17. The method of claim 1 , further comprising a fluoride source, water, and optionally metal chelating agent(s).

18. The method of claim 17 , comprising triethanolamine, triethanolammonium fluoride, pentamethyldiethylenetriamine, iminodiacetic acid, ammonium bifluoride and water.

19. The method of claim 1 , wherein the substrate contacted with the wafer cleaning formulation comprises slurry particles remaining after chemical mechanical polishing.

Assignments (5)
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 →
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 →
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 →