Copper electroplating baths containing reaction products of amines, polyacrylamides and bisepoxoides

Patent metadata

Field	Value
Publication number	US-12398479-B2
Application number	US-202016780939-A
Country	US
Kind code	B2
Filing date	Feb 4, 2020
Priority date	Oct 8, 2015
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

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

First claim

What is claimed is:

1. A reaction product of a bisepoxide, an amine and an acrylamide, wherein the amine has a formula:

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

where m is an integer from 2-12, n is an integer from 2-10, p is an integer from 1-10; and the acrylamide has a formula:

wherein R″ is a moiety having a structure:

a moiety having a structure:

 or
a substituted or unsubstituted triazinane ring or a piperazine ring, wherein 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 reaction product of claim 1 , wherein the bisepoxide has the formula:

wherein R 18 and R 19 are independently chosen from hydrogen and (C 1 -C 4 )alkyl and R 22 and R 23 are independently chosen from hydrogen, methyl and hydroxyl, and a=1-6 and b=1-20.

3. The reaction product of claim 1 , wherein R comprises HO—(CH 2 ) m —, wherein m is an integer from 2-12.

4. The reaction product of claim 1 , wherein R comprises a moiety having a structure:

wherein n is an integer from 2-10 and p is an integer from 1-10.

5. The reaction product of claim 1 , wherein R″ is a moiety having a structure:

wherein 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.

6. A reaction product of a bisepoxide, an amine and an acrylamide, wherein the amine has a formula:

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

 or
a moiety having a structure:

where R 7 -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:

wherein v, x and y are independently integers of 1 to 10.

7. The reaction product of claim 6 , wherein R comprises Q-(CH 2 ) m —, wherein 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 m is an integer from 2-12.

8. The reaction product of claim 6 , wherein R comprises a moiety having a structure:

wherein R 7 -R 14 are independently chosen from hydrogen and (C 1 -C 3 )alkyl; q is an integer from 2-10 and r, s and t are numbers from 1 to 10.

9. A reaction product of a bisepoxide, an amine and an acrylamide, wherein the amine has a formula:

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

 or
a moiety having a structure:

where R 7 -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 substituted or unsubstituted triazinane ring or a piperazine ring.

Assignees

• Dow Global Technologies Llc
• Rohm & Haas Elect Mat

Inventors

• Lu Weijing
• Duan Lingli
• Niazimbetova Zukhra
• Chen Chen
• Rzeznik Maria

Classifications

• C08G59/22

  Di-epoxy compounds · CPC title

• C08G59/502

  Polyalkylene polyamines · CPC title

• C08G73/0206

  Polyalkylene(poly)amines · CPC title

• C08G73/024

  Polyamines containing oxygen in the form of ether bonds in the main chain · CPC title

• C25D3/58

  containing more than 50% by weight of copper · CPC title