Reaction products of heterocyclic nitrogen compounds polyepoxides and polyhalogens

Patent metadata

Field	Value
Publication number	US-10190226-B2
Application number	US-201615207957-A
Country	US
Kind code	B2
Filing date	Jul 12, 2016
Priority date	Apr 16, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

Reaction products of heterocyclic nitrogen compounds, polyepoxide compounds and polyhalogen compounds may be used as levelers in metal electroplating baths, such as copper electroplating baths, to provide good throwing power. Such reaction products may plate metal with good surface properties and good physical reliability.

First claim

What is claimed is:

1. A compound comprising a reaction product of one or more heterocyclic nitrogen compounds comprising at least two reactive nitrogen atoms with the proviso that at least one of the reactive nitrogen atoms is in the ring of the one or more heterocyclic nitrogen compounds; one or more polyepoxide compounds and one or more polyhalogen compounds, wherein the one or more polyhalogen compounds have a formula:
X 1 —R 13 —X 2   (VII)

wherein X 1 and X 2 may be the same or different and are halogens chosen from chlorine, bromine, fluorine and iodine, R 13 is linear or branched, substituted or unsubstituted (C 1 -C 20 )alkyl, or is a moiety having formula:
—C(HR 14 )—R 15 —C(HR 14 )—  (VIII)

wherein each R 14 is independently selected from hydrogen, halogens chosen from chlorine, bromine, fluorine and iodine, linear or branched, substituted or unsubstituted (C 1 -C 18 )alkyl, substituted or unsubstituted (C 6 -C 12 )cycloalkyl, substituted or unsubstituted (C 6 -C 15 )aryl; R 15 is linear or branched, substituted or unsubstituted (C 1 -C 18 )alkyl, substituted or unsubstituted (C 6 -C 12 )cycloalkyl, substituted or unsubstituted (C 6 -C 15 )aryl, —CH 2 —O—(R 16 —O) d —CH 2 — where R 16 is a substituted or unsubstituted, linear or branched (C 2 -C 10 )alkyl and d is an integer of 1-10.

2. The compound of claim 1 , wherein the one or more heterocyclic nitrogen compounds are chosen from imidazoles, triazoles, tetrazoles, pyrazines, benzimidazoles, benzotriazoles, purines, piperazines, pyridazines, triazines, tetrazines and pyrimidines, pyrazoles, piperidines, benzoxazoles, oxazoles, pyridines, morpholines, pyrrolidines, pyrroles, quinolines, isoquinolines and benzothiazoles.

3. The compound of claim 1 , wherein the one or more heterocyclic nitrogen compounds have a formula:

wherein Q 1 -Q 4 may be nitrogen, oxygen, carbon, or sulfur with the proviso that at least one of the Q 1 -Q 4 is nitrogen, and that only one of the Q 1 -Q 4 may be oxygen or sulfur at any instance, the carbon atoms and nitrogen atoms may be substituted or unsubstituted and R 1 is hydrogen; hydroxyl; linear or branched alkoxy; linear or branched, substituted or unsubstituted (C 1 -C 10 )alkyl; linear or branched, substituted or unsubstituted hydroxy(C 1 -C 10 )alkyl; linear or branched, substituted or unsubstituted alkoxy(C 1 -C 10 )alkyl; linear or branched, substituted or unsubstituted carboxy(C 1 -C 10 )alkyl; linear or branched, substituted or unsubstituted amino(C 1 -C 10 )alkyl; substituted or unsubstituted aryl; linear or branched, substituted or unsubstituted aryl(C 1 -C 10 )alkyl; substituted or unsubstituted sulfonyl; and substituted or unsubstituted amine, with the proviso that when only one of Q 1 -Q 4 is an unsubstituted nitrogen atom, at least one substituent on the ring comprises a reactive nitrogen atom comprising one or more of a primary amino moiety; secondary amino moiety; an aromatic or non-aromatic heterocyclic nitrogen moiety comprising at least one unsubstituted nitrogen atom; an amide moiety; and a Schiff base moiety.

4. The compound of claim 1 , wherein the one or more heterocyclic nitrogen compounds have a formula:

wherein Q 9 -Q 14 is nitrogen, carbon or oxygen with the proviso that at least one of Q 9 -Q 14 is nitrogen and there are no more than four nitrogen atoms in the ring, the carbon atoms and nitrogen atoms in the ring may be substituted or unsubstituted, and when only one of Q 9 -Q 14 is an unsubstituted nitrogen atom, at least one substituent on the ring comprises a reactive nitrogen atom comprising one or more of a primary amino moiety; secondary amino moiety; an aromatic or non-aromatic heterocyclic nitrogen moiety comprising at least one unsubstituted nitrogen atom; an amide moiety; and a Schiff base moiety; and when oxygen is present in the ring, only one of Q 9 -Q 14 is oxygen.

5. The compound of claim 1 , wherein the one or more polyepoxide compounds have a formula:

wherein R 2 and R 3 may be the same or different and are chosen from hydrogen and (C 1 -C 4 )alkyl, A=OR 4 or R 5 ; R 4 ═((CR 6 R 7 ) m O), (aryl-O) p , CR 6 R 7 —Z—CR 6 CR 7 , or OZ′ t O, R 5 ═(CH 2 ) y , B is (C 5 -C 12 )cycloalkyl, Z=a 5- or 6-membered ring, Z′ is R 5 OArOR 8 , (R 9 O) b Ar(OR 9 ), or (R 9 O) b , Cy(OR 9 ), Cy=(C 5 -C 12 )cycloalkyl, R 6 and R 7 are independently chosen from hydrogen, methyl, or hydroxyl, R 8 represents (C 1 -C 8 )alkyl, R 9 represents a (C 2 -C 6 )alkyleneoxy, R 10 is a hydrogen atom, a formyl group, or one or two glycidyl ether groups each optionally containing a carbonyl group constituted by C 4 -C 8 and C 2 -C 4 , R 11 is a hydrogen atom, a methyl group or an ethyl group, and Rig is a hydrogen atom, a formyl group, or one or two glycidyl ether groups each optionally containing a carbonyl group constituted by C 4 -C 8 and C 2 -C 4 , b=1-10, m=1-6, n=1-4, p=1-6, t=1-4 and y=0-6.

6. A composition comprising one or more sources of metal ions, an electrolyte and one or more compounds comprising a reaction product of one or more heterocyclic nitrogen compounds comprising at least two reactive nitrogen atoms with the proviso that at least one of the reactive nitrogen atoms is in the ring of the one or more heterocyclic nitrogen compounds; one or more polyepoxide compounds and one or more polyhalogen compounds, wherein the one or more polyhalogen compounds have a formula:
X 1 —R 13 —X 2   (VII)

wherein X 1 and X 2 may be the same or different and are halogens chosen from chlorine, bromine, fluorine and iodine, R 13 is linear or branched, substituted or unsubstituted (C 1 -C 20 )alkyl, or is a moiety having formula:
—C(HR 14 )—R 15 —C(HR 14 )—  (VIII)

wherein each R 14 is independently selected from hydrogen, halogens chosen from chlorine, bromine, fluorine and iodine, linear or branched, substituted or unsubstituted (C 1 -C 18 )alkyl, substituted or unsubstituted (C 6 -C 12 )cycloalkyl, substituted or unsubstituted (C 6 -C 15 )aryl; R 15 is linear or branched, substituted or unsubstituted (C 1 -C 18 )alkyl, substituted or unsubstituted (C 6 -C 12 )cycloalkyl, substituted or unsubstituted (C 6 -C 15 )aryl, —CH 2 —O—(R 16 —O) d —CH 2 — where R 16 is a substituted or unsubstituted, linear or branched (C 2 -C 10 )alkyl and d is an integer of 1-10.

7. The compound of claim 1 , wherein the one or more polyepoxide compounds 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 and poly(propyleneglycol) diglycidyl ether.

8. The compound of claim 1 , wherein the one or more polyepoxide compounds 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.

9. The compound of claim 1 , wherein the one or more polyepoxide compounds are chosen from dicyclopentadiene dioxide and 1,2,5,6-diepoxycyclooctane.

10. The compound of claim 1 , wherein the metal ions are copper ion, tin ions or mixtures thereof.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Kozhukh Julia
• Niazimbetova Zuhra I

Classifications

• H05K3/42

  Plated through-holes {or plated via connections} · CPC title

• H05K3/421

  Blind plated via connections (H05K3/422, H05K3/423 and H05K3/425 take precedence) · CPC title

• C25D3/38

  of copper · CPC title

• C25D3/60

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

• C25D3/58

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