IP Library Granted Patent US 10,604,858
Granted Patent B2
US 10,604,858 · App. 15/752,636 · Granted Mar 31, 2020

Copper electroplating baths containing compounds of reaction products of amines, polyacrylamides and sultones

Inventors: Weijing Lu (Fanling, HK); Lingli Duan (Pudong District, CN); Zukhra Niazimbetova (Marlborough, MA); Chen Chen (Pudong District, CN); Maria Rzeznik (Marlborough, MA)
Assignees: Dow Global Technologies LLC; Rohm and Haas Electronic Materials LLC
C25D3/38C25D3/58C25D7/12
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Quick Facts
Patent No.
US 10,604,858
App. No.
15/752,636
Granted
Mar 31, 2020
Kind
B2
Abstract

Copper electroplating baths include reaction products of amines, polyacrylamides and sultones. The reaction products function as levelers and enable copper electroplating baths which have high throwing power and provide copper deposits with reduced nodules.

Claims (20)

1. An electroplating bath comprising one or more sources of copper ions, one or more accelerators, one or more suppressors, one or more electrolytes and one or more compounds comprising a reaction product of one or more compounds having the formula:

wherein R 24 -R 27 are independently chosen from hydrogen, (C 1 -C 3 )alkyl, hydroxyl, and acetate moiety, an amine and an acrylamide, wherein the amine has a formula:

wherein R′ is hydrogen; R comprises H 2 N(CH 2 ) m —, HO—(CH 2 ) m —, Q-(CH 2 ) m —, a moiety having a structure:

a moiety having a structure:

or

a moiety having a structure:

where R 1 -R 14 are independently chosen from hydrogen and (C 1 -C 3 )alkyl; m is an integer from 2-12, n is an integer from 2-10, p is an integer from 1-10, q is an integer from 2-10 and r, s and t are numbers from 1 to 10; Q is a 5-6 membered heterocyclic ring having one or two nitrogen atoms in the ring or Q is a benzene sulfonamide moiety; and the acrylamide has a formula:

wherein R″ is a moiety having a structure:

a moiety having a structure:

a moiety having a structure:

or

a substituted or unsubstituted triazinane ring or a piperizine ring, wherein R 15 comprises hydrogen or hydroxyl; u is an integer from 1 to 2 and v, x and y are independently integers of 1 to 10; R 16 and R 17 are independently chosen from hydrogen and carbonyl moiety, and with the proviso that when R 16 and R 17 are carbonyl moieties, the carbonyl moieties form a covalent bond with the carbons of the vinyl groups of formula (VI) displacing a hydrogen to form the covalent bond with the carbons of the vinyl groups to form a five membered heterocyclic ring.

2. The electroplating bath of claim 1 , further comprising one or more sources of tin ions.

3. The electroplating bath of claim 1 , wherein the one or more compounds are in amounts of 0.01 ppm to 1000 ppm.

4. A method of electroplating comprising:

a) providing a substrate;

b) immersing the substrate in the electroplating bath of claim 1 ;

c) applying a current to the substrate and the electroplating bath; and

d) electroplating copper on the substrate.

5. The method of claim 4 , wherein the substrate comprises a plurality of one or more of through-holes, trenches and vias.

Assignments (6)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Jun 9, 2025
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 071500/0678 →
CORRECTIVE ASSIGNMENT TO CORRECT THE MISSING INVERTOR PREVIOUSLY RECORDED AT REEL: 052103 FRAME: 0530. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 26, 2023
From: LU, WEIJING; RZEZNIK, MARIA; NIAZIMBETOVA, ZUKHRA
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 064389/0547 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2020
From: LU, WEIJING; RZEZNIK, MARIA
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 052103/0530 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2020
From: DUAN, LINGLI; CHEN, CHEN
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 052103/0540 →
Continuity (1)
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