Sulfonamide based polymers for copper electroplating

Patent metadata

Field	Value
Publication number	US-9611560-B2
Application number	US-201414585227-A
Country	US
Kind code	B2
Filing date	Dec 30, 2014
Priority date	Dec 30, 2014
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

Sulfonamide based polymers are reaction products of sulfonamides and epoxides. The polymers may be used as levelers in copper electroplating baths, to provide good throwing power. Such reaction products may plate copper or copper alloys with good surface properties and good physical reliability.

First claim

What is claimed is:

1. An electroplating composition comprising one or more sources of copper ions, water, one or more suppressors, one or more brightening agents, an electrolyte comprising one or more acids selected from the group consisting of sulfuric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and hydrochloric acid and one or more sources of halide ions, and a reaction product of one or more sulfonamides or salts thereof, and one or more epoxides.

2. The composition of claim 1 , wherein the one or more epoxides comprise

wherein Y, R 5 and R 6 may be the same or different and are chosen from hydrogen and C 1 -C 4 )alkyl, X is halogen, A=OR 10 or R 11 ; R 10 =((CR 12 R 13 ) m O), (aryl-O) p , CR 12 R 13 —Z—CR 12 CR 13 , or OZ' t O, R 11 =(CH 2 ) y , B is (C 5 -C 12 )cycloalkyl, Z=a 5- or 6-membered ring, Z' is R 14 OArOR 14 ,(R 15 O) b Ar(OR 15 ), or (R 15 O) b , Cy(OR 15 ), Cy=(C 5 -C 12 )cycloalkyl; R 12 and R 13 are independently chosen from hydrogen, methyl, or hydroxyl, R 14 represents (C 1 -C 8 )alkyl, R 15 represents a (C 2 -C 6 )alkyleneoxy; R 7 is a hydrogen atom, a formyl group, or one or two glycidyl ether groups optionally containing a carbonyl group constituted by C 4 -C 8 and C 2 -C 4 , R 8 is a hydrogen atom, a methyl group or an ethyl group, and R 9 is a hydrogen atom, a formyl group, or one or two glycidyl ether groups optionally containing a carbonyl group constituted by C 4 -C 8 and C 2 -C 4 , and b=1-10, m=1-6, n=1-4, p=1-6, t=1-4 and y=0-6.

3. The composition of claim 1 , wherein the one or more epoxides are chosen from 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, glycerol diglycidyl ether, neopentyl glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, poly(ethyleneglycol) diglycidyl ether and poly(propyleneglycol) diglycidyl ether.

4. The composition of claim 1 , wherein the one or more epoxides are chosen from glycerin triglycidyl ether, trimethylolpropanetriglycidyl ether, diglycerol tetraglycidyl ether, erythritol tetraglycidyl ether, arabinose tetraglycidyl ether, triglycerol pentaglycidyl ether, fructose pentaglycidyl ether, xylitol pentaglycidyl ether, tetraglycerol hexaglycidyl ether, and sorbitol hexaglycidyl ether.

5. The composition of claim 1 , wherein the one or more epoxides are chosen from epichlorohydrin and epibromohydrin.

6. The composition of claim 1 , wherein the one or more epoxides are chosen from dicyclopentadiene dioxide and 1,2,5,6-diepoxycyclooctane.

7. An electroplating composition comprising one or more sources of copper ions, water, one or more suppressors, one or more brightening agents, an electrolyte comprising one or more acids selected from the group consisting of sulfuric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid and hydrochloric acid and one or more sources of halide ions, and a reaction product of one or more sulfonamides or salts thereof, one or more epoxides and one or more amines.

8. The composition of claim 7 , wherein the one or more amines are chosen from primary amines, secondary amines, hydroxyl amines, polyamines and heterocyclic amines.

9. The composition of claim 8 , wherein the heterocyclic amines are chosen from imidazoles, triazoles, tetrazoles, pyrazines, benzimidazoles, benzothiazoles, purines, piperazines, pyridazines, pyrazoles, triazines, tetrazines, pyrimidines, benzoxazoles, oxazoles, pyridines, morpholines, pyrrolidines, pyrroles, quinolines, isoquinolines and benzothiazoles.

10. The composition of claim 7 , wherein the one or more epoxides are chosen from 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, glycerol diglycidyl ether, neopentyl glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, poly(ethyleneglycol) diglycidyl ether and poly(propyleneglycol) diglycidyl ether.

11. The composition of claim 7 , wherein the one or more epoxides are chosen from 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, glycerol diglycidyl ether, neopentyl glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, poly(ethyleneglycol) diglycidyl ether and poly(propyleneglycol) diglycidyl ether.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Lu Weijing
• Niazimbetova Zuhra I
• Rzeznik Maria Anna

Classifications

• H05K3/241

  characterised by the electroplating method; means therefor, e.g. baths or apparatus · CPC title

• C25D3/38 Primary

  of copper · CPC title

• C25D3/60

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

• C07D303/20

  Ethers with hydroxy compounds containing no oxirane rings · CPC title

• C07C311/17

  to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms · CPC title