Polyalkanolamines

Patent metadata

Field	Value
Publication number	US-12522936-B2
Application number	US-202118001078-A
Country	US
Kind code	B2
Filing date	Jun 7, 2021
Priority date	Jun 10, 2020
Publication date	Jan 13, 2026
Grant date	Jan 13, 2026

Abstract

Disclosed herein is a A polyalkanolamine including the structure of formula L1

[A L ] n [B L ] m   (L1)
wherein

X L1 , X L2 , X L3 are independently selected from a C 1 to C 6 alkanediyl;
Ar L is a 5 or 6 membered N-heteroaromatic ring system including from 1 to 4 N atoms, which may be unsubstituted or substituted by C 1 to C 6 alkyl;
n is an integer of from 2 to 350;
m is 0 or an integer of from 1 to 600;
o is 1 or an integer of from 2 to 25;
B L1 is a continuation of the backbone B L by branching;
X L11 , X L12 , X L13 are independently selected from a C 1 to C 6 alkanediyl;
X L21 is a C 1 to C 6 alkanediyl;
and derivatives thereof obtainable by N-protonation, N-quaternization, substitution, or polyalkoxylation.

First claim

The invention claimed is:

1 . A polyalkanolamine comprising the structure of formula L1
[A L ] n [B L ] m   (1)
wherein

X L1 , X L2 , X L3 are independently selected from the group consisting of C 1 to C 6 alkanediyl;
Ar L is a monovalent 5 or 6 membered N-heteroaromatic ring system comprising from 1 to 4 N atoms, which ring system may be unsubstituted or substituted by C 1 to C 6 alkyl;
n is an integer of from 2 to 350;
m is 0 or an integer of from 1 to 600;
o is 1 or an integer of from 2 to 25;
B L1 is a continuation of the backbone B L by branching;
R L33 is H or a C 1 to C 6 alkyl;
X L11 , X L12 , X L13 are independently selected from the group consisting of C 1 to C 6 alkanediyl;
X L21 is a C 1 to C 8 alkanediyl;
and derivatives thereof obtainable by N-protonation, N-quaternization, N- or O-substitution, or N- or O-alkoxylation.

2 . The polyalkanolamine according to claim 1 , wherein the additive is a compound of formula L2
R L1 -[A L ] n [B L ] m —OR L2   (L2)
wherein R L1 and R L2 are termination groups.

3 . The polyalkanolamine according to claim 1 , wherein Ar L is selected from the group consisting of imidazole-1-yl and pyridyl.

4 . The polyalkanolamine according to claim 1 , wherein X L1 , X L2 , and X L3 , and if applicable X L11 , X L12 , and X L13 are independently selected from the group consisting of methanediyl, ethane-1,2-diyl, propane-1,3-diyl, propane-1,2-diyl, 2-methylpropane-1,2-diyl, 2,2-dimethylpropane-1,3-diyl, butane-1,4-diyl, butane-1,3-diyl, butane-1,2-diyl, butane-2,3-diyl, 2-methylbutane-1,3-diyl, 3-methylbutane-1,3-diyl, pentane-1,2-diyl, pentane-1,5-diyl, pentane-2,5-diyl, 2-methylpentane-2,5-diyl and hexane-1,6-diyl.

5 . The polyalkanolamine according to claim 1 , wherein m is 0.

6 . The polyalkanolamine according to claim 5 , wherein all fragments [A L ] in the polyalkanolamine of formula [A L ] n are the same.

7 . The polyalkanolamine according to claim 5 , wherein the polyalkanolamine is a compound of formula L11

wherein
R L1 , R L2 are independently selected from the group consisting of H, C 1 to C 6 alkyl, polyoxy(C 2 -C 12 )alkylene, sulfate, sulfonate, phosphate, and phosphonate.

8 . The polyalkanolamine according to claim 1 , wherein m is an integer of from 3 to 250 and B L is selected from the group consisting of —[X L21 —O] o —.

9 . The polyalkanolamine according to claim 8 , wherein the polyalkanolamine is a compound of formula L12

wherein
o is an integer from 2 to 20;
R L1 , R L2 are independently selected from the group consisting of H, methyl, ethyl, propyl and butyl;
R L31 is H, methyl, ethyl or propyl.

10 . The polyalkanolamine according to claim 1 , wherein the polyalkanolamine is a compound of formula L13

wherein
z is an integer of from 1 to 8;
R L1 , R L2 are independently selected from the group consisting of H, methyl, ethyl, propyl and butyl; and
R L31 is H, methyl, ethyl or propyl.

11 . The polyalkanolamine according to claim 1 , wherein the polyalkanolamine is a compound of formula L14

wherein
R L1 , R L2 are independently selected from the group consisting of H, methyl, ethyl, propyl or butyl.

12 . A composition for copper electroplating comprising copper ions and at least one polyalkanolamine according to claim 1 .

13 . The composition according to claim 12 , wherein the pH is from 0 to 5.

14 . The composition according to claim 12 , further comprising one or more accelerating agents, one or more suppressing agents, or a combination thereof.

15 . A method of using the composition according to claim 12 , the method comprising using the composition for depositing copper on a substrate comprising a recessed feature comprising a conductive feature bottom and a dielectric feature side wall, wherein the recessed feature has an aperture size from 500 nm to 500 μm.

16 . A process for electrodepositing copper on a substrate comprising a recessed feature comprising a conductive feature bottom and a dielectric feature side wall, the process comprising:
a) contacting a composition according to claim 12 with the substrate, and b) applying a current to the substrate for a time sufficient to deposit a copper layer into the recessed feature, wherein the recessed feature has an aperture size from 500 nm to 500 μm.

17 . The polyalkanolamine according to claim 1 , wherein the additive is a compound of formula L2
R L1 -[A L ] n [B L ] m —OR L2   (L2)
wherein R L1 and R L2 are termination groups selected from the group consisting of H, C 1 to C 6 alkyl, polyoxy(C 2 -C 12 )alkylene, sulfate, sulfonate, phosphate, and phosphonate.

18 . The polyalkanolamine according to claim 8 , wherein the polyalkanolamine is a compound of formula L12

wherein
o is an integer from 2 to 20;
R L1 , R L2 is H;
R L31 is H.

19 . The polyalkanolamine according to claim 1 , wherein the polyalkanolamine is a compound of formula L13

wherein
z is an integer of from 1 to 8;
R L1 , R L2 is H; and
R L31 is H.

20 . The polyalkanolamine according to claim 1 , wherein the polyalkanolamine is a compound of formula L14

wherein
R L1 , R L2 are each H.

Assignees

• Basf Se

Inventors

• Arnold Marco
• Fluegel Alexander
• Emnet Charlotte
• Engelhardt Nadine

Classifications

• C25D7/12

  Semiconductors · CPC title

• C08K2003/085

  Copper · CPC title

• C08K5/3415

  Five-membered rings · CPC title

• C08K3/08

  Metals · CPC title

• C08G73/024 Primary

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