IP Library Granted Patent US 6,899,818
Granted Patent B2
US 6,899,818 · App. 10/220,720 · Granted May 31, 2005

Method and composition for removing sodium-containing material from microcircuit substrates

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Quick Facts
Patent No.
US 6,899,818
App. No.
10/220,720
Granted
May 31, 2005
Kind
B2
Abstract

A method and composition for removing sodium-containing materials such as photoresist from microcircuit substrate material utilizes 1,2-Diaminocyclohexanetetracarboxylic Acid in an organic solvent.

Claims (22)

1. A method of inhibiting adsorption of sodium-to integrated circuit surfaces during photoresist removal or post-metal etch cleanup with an organic solvent-containing composition, comprising contacting the surface with an organic solvent-containing composition comprising:

a) 1,2-diaminocyclohexanetetracarboxylic acid (CYDTA),

b) a nucleophilic amine present in an amount of from about 1 to less than about 50% by weight of the composition,

c) a non-nitrogen containing weak acid in an amount sufficient to partially neutralize the nucleophilic amine such that the composition has an aqueous pH, when diluted with about 10 parts of water, of about 9.6 to about 10.9, said weak acid having a pKa value in aqueous solution of 2.0 or greater and an equivalent weight of less than 140, and

the solvent is a stripping solvent system having a solubility parameter of from about 8 to about 15 and is present in an amount of from about 50% to about 85% by weight of the composition.

2. The method of claim 1 comprising, on a weight basis, from about 50% to about 85% of N-methyl-2-pyrrolidinone as solvent, from about 1 to about 20% of tetrahydrothiophene-1,1-dioxide as solvent, from about 1 to about 20% of water, from about 1 to about 50% of 2-aminoethanol as the nucleophilic amine, from about 0.05% to about 25% of 1,2-dihydroxybenzene as the non-nitrogen containing weak acid and about 0.01% to 5% of 1,2-diaminocyclohexanetetracarboxylic acid.

3. The method of claim 1 , wherein the non-nitrogen containing weak acid is present in the composition in an amount of from about 0.05% to about 25% by weight of said stripping composition.

4. The method of claim 3 , wherein the non-nitrogen containing weak acid has a pKa of 2.5 or higher.

5. The method of claim 4 wherein the non-nitrogen containing weak acid is 1,2-dihydroxybenzene.

6. The method of claim 5 wherein the nucleophilic amine is 2-aminoethanol.

7. The method of claim 6 wherein the solvent system comprises N-methyl-2-pyrrolidinone and tetrahydrothiophene-1,1-dioxide and optionally up to about 10% water.

8. A composition for inhibiting adsorption of sodium-to integrated circuit surfaces during photoresist removal or post-metal etch cleanup with an organic solvent-containing composition, said organic solvent-containing composition comprising:

a) 1,2-diaminocyclohexanetetracarboxylic acid (CyDTA),

b) a nucleophilic amine present in an amount of from about 1 to less than about 50% by weight of the composition,

c) a non-nitrogen containing weak acid in an amount sufficient to partially neutralize the nucleophilic amine such that the composition has an aqueous pH, when diluted with a bout 10 p arts of water, of a bout 9.6 to about 10.9, said weak acid having a pKa value in aqueous solution of 2.0 or greater and an equivalent weight of less than 140, and

the solvent is a stripping solvent system having a solubility parameter of from about 8 to about 15 and is present in an amount of from about 50% to about 85% by weight of the composition.

9. The composition of claim 8 comprising, on a weight basis, from about 50% to about 85% of N-methyl-2-pyrrolidinone as solvent, from about 1 to about 20% of tetrahydrothiophene-1,1-dioxide as solvent, from about 1 to about 20% of water, from about 1 to about 50% of 2-aminoethanol as the nucleophilic amine, from about 0.05% to about 25% of 1,2-dihydroxybenzene as the non-nitrogen containing weak acid and about 0.01% to 5% of 1,2-diaminocyclohexanetetracarboxylic acid.

10. The composition of claim 8 , wherein the non-nitrogen containing weak acid is present in the composition in an amount of from about 0.05% to about 25% by weight of said stripping composition.

11. The composition of claim 10 , wherein the non-nitrogen containing weak acid has a pKa of 2.5 or higher.

12. The composition of claim 11 wherein the non-nitrogen containing weak acid is 1,2-dihydroxybenzene.

13. The composition of claim 12 wherein the nucleophilic amine is 2-aminoethanol.

14. The composition of claim 13 wherein the solvent system comprises N-methyl-2-pyrrolidinone and tetrahydrothiophene-1,1-dioxide and optionally up to about 10% water.

Assignments (18)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Nov 16, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: AVANTOR PERFORMANCE MATERIALS, LLC; NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; RELIABLE BIOPHARMACEUTICAL, LLC; THERAPAK, LLC
Reel/Frame 054440/0877 →
SECURITY AGREEMENT (NOTES) Recorded Nov 6, 2020
From: AVANTOR FLUID HANDLING, LLC; AVANTOR PERFORMANCE MATERIALS, LLC; NUSIL TECHNOLOGY LLC; RELIABLE BIOPHARMACEUTICAL, LLC; THERAPAK, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 054343/0414 →
SECURITY AGREEMENT Recorded Nov 29, 2017
From: AVANTOR PERFORMANCE MATERIALS, LLC; NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; RELIABLE BIOPHARMACEUTICAL, LLC; THERAPAK, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 044528/0960 →
SECURITY AGREEMENT Recorded Nov 28, 2017
From: AVANTOR PERFORMANCE MATERIALS, LLC; NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; RELIABLE BIOPHARMACEUTICAL, LLC; THERAPAK, LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 044811/0400 →
RELEASE (REEL 041966 / FRAME 0247) Recorded Nov 27, 2017
From: JEFFERIES FINANCE LLC
To: NUSIL TECHNOLOGY, LLC; APPLIED SILICONE COMPANY LLC; AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY AVANTOR PERFORMANCE MATERIALS, INC.)
Reel/Frame 044810/0154 →
RELEASE (REEL 041966 / FRAME 0211) Recorded Nov 27, 2017
From: JEFFERIES FINANCE LLC
To: NUSIL TECHNOLOGY, LLC; APPLIED SILICONE COMPANY, LLC; AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY AVANTOR PERFORMANCE MATERIALS, INC.)
Reel/Frame 044810/0207 →
SECURITY INTEREST Recorded Mar 10, 2017
From: NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY KNOWN AS AVANTOR PERFORMANCE MATERIALS, INC.)
To: JEFFERIES FINANCE LLC
Reel/Frame 041966/0247 →
SECURITY INTEREST Recorded Mar 10, 2017
From: NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY KNOWN AS AVANTOR PERFORMANCE MATERIALS, INC.)
To: JEFFERIES FINANCE LLC
Reel/Frame 041966/0211 →
RELEASE OF SECURITY INTEREST Recorded Mar 10, 2017
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY KNOWN AS AVANTOR PERFORMANCE MATERIALS, INC.); NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC
Reel/Frame 041966/0313 →
CHANGE OF NAME Recorded Mar 2, 2017
From: AVANTOR PERFORMANCE MATERIALS, INC.
To: AVANTOR PERFORMANCE MATERIALS, LLC
Reel/Frame 041442/0976 →
MERGER Recorded Oct 3, 2016
From: AVANTOR PERFORMANCE MATERIALS, INC.
To: AVANTOR PERFORMANCE MATERIALS, LLC
Reel/Frame 039924/0311 →
SECURITY INTEREST Recorded Sep 30, 2016
From: NUSIL TECHNOLOGY LLC; APPLIED SILICONE COMPANY LLC; AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY KNOWN AS AVANTOR PERFORMANCE MATERIALS, INC.)
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
Reel/Frame 040192/0613 →
RELEASE OF SECURITY INTEREST Recorded Sep 30, 2016
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: AVANTOR PERFORMANCE MATERIALS, LLC (FORMERLY KNOWN AS AVANTOR PERFORMANCE MATERIALS, INC.)
Reel/Frame 039915/0035 →
SECURITY INTEREST Recorded Jun 21, 2016
From: AVANTOR PERFORMANCE MATERIALS, INC.
To: CREDIT SUISSE, AG, CAYMAN ISLANDS BRANCH
Reel/Frame 038976/0610 →
RELEASE OF SECURITY INTEREST Recorded Jun 21, 2016
From: CREDIT SUISSE, AG, CAYMAN ISLANDS BRANCH
To: AVANTOR PERFORMANCE MATERIALS, INC.
Reel/Frame 039111/0908 →
RELEASE OF SECURITY INTEREST Recorded Jun 21, 2016
From: CREDIT SUISSE, AG, CAYMAN ISLANDS BRANCH
To: AVANTOR PERFORMANCE MATERIALS, INC.
Reel/Frame 038975/0807 →
SECURITY INTEREST Recorded Jun 21, 2016
From: AVANTOR PERFORMANCE MATERIALS, INC.
To: CREDIT SUISSE, AG, CAYMAN ISLANDS BRANCH
Reel/Frame 038976/0478 →
PATENT SECURITY AGREEMENT Recorded Jun 24, 2011
From: AVANTOR PERFORMANCE MATERIALS, INC.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
Reel/Frame 026499/0256 →