IP Library Granted Patent US 11,761,107
Granted Patent B2
US 11,761,107 · App. 16/745,400 · Granted Sep 19, 2023

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 (Westborough, MA); Chen Chen (Pudong District, CN); Maria Rzeznik (Shrewsbury, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
C25D3/38C08G73/02C25D3/58C25D7/12
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Quick Facts
Patent No.
US 11,761,107
App. No.
16/745,400
Granted
Sep 19, 2023
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 (12)

1. A compound 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 compound of claim 1 , wherein the amine has a formula:

wherein R′ is hydrogen and R is H 2 N—(CH 2 ) m — and m is an integer of 2-3.

Assignments (3)
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 →