Coating metal foil with N-heterocyclic carbene compounds containing organic functionalities for improving metal-to-resin adhesion

Patent metadata

Field	Value
Publication number	US-9974193-B2
Application number	US-201514871991-A
Country	US
Kind code	B2
Filing date	Sep 30, 2015
Priority date	Dec 2, 2014
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

A carbene-coated metal foil is produced by applying an N-heterocyclic carbene (NHC) compound to one or more surfaces of a metal foil (e.g., an electrodeposited copper foil having a surface that is smooth and non-oxidized). The NHC compound contains a matrix-reactive pendant group that includes at least one of a vinyl-, allyl-, acrylic-, methacrylic-, styrenic-, amine-, amide- and epoxy-containing moiety capable of reacting with a base polymer (e.g., a vinyl-containing resin such as a polyphenylene oxide/triallyl-isocyanurate (PPO/TAIC) composition). The NHC compound may be synthesized by, for example, reacting a halogenated imidazolium salt (e.g., 1,3-bis(4-bromo-2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride) and an organostannane having a vinyl-containing moiety (e.g., tributyl(vinyl)stannane) in the presence of a palladium catalyst. In some embodiments, an enhanced substrate for a printed circuit board (PCB) is produced by laminating the carbene-coated metal foil to a substrate that includes glass fiber impregnated with the base polymer.

First claim

What is claimed is:

1. A method for producing an enhanced substrate for a printed circuit board (PCB) comprising:
providing a substrate, wherein the substrate comprises glass fiber impregnated with a base polymer, and wherein the base polymer comprises a vinyl-containing resin;
laminating a carbene-coated metal foil to the substrate, wherein the carbene-coated metal foil comprises a conductive surface treated with an N-heterocyclic carbene (NHC) compound comprising a matrix-reactive pendant group, and wherein the NHC compound is a vinyl-functionalized NHC compound represented by the following formula:

synthesizing the vinyl-functionalized NHC compound by reacting 1,3-bis(4-bromo-2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride with tributyl(vinyl)stannane via palladium-catalyzed Stille coupling.

2. A method for producing an enhanced substrate for a printed circuit board (PCB) comprising:
providing a substrate, wherein the substrate comprises glass fiber impregnated with a base polymer, and wherein the base polymer comprises a vinyl-containing resin;
laminating a carbene-coated metal foil to the substrate, wherein the carbene-coated metal foil comprises a conductive surface treated with an N-heterocyclic carbene (NHC) compound comprising a matrix-reactive pendant group and wherein the NHC compound is an acrylate-functionalized NHC compound represented by the following formula:

synthesizing the acrylate-functionalized NHC compound by reacting 1,3-bis(4-bromo-2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride with tributyltin acrylate via palladium-catalyzed Stille coupling.

3. A method for producing an enhanced substrate for a printed circuit board (PCB) comprising:
providing a substrate, wherein the substrate comprises glass fiber impregnated with a base polymer, and wherein the base polymer comprises a vinyl-containing resin;
laminating a carbene-coated metal foil to the substrate, wherein the carbene-coated metal foil comprises a conductive surface treated with an N-heterocyclic carbene (NHC) compound comprising a matrix-reactive pendant group and wherein the NHC compound is a styrene-functionalized NHC compound represented by the following formula:

synthesizing the styrene-functionalized NHC compound by reacting 1,3-bis(4-bromo-2,6-dimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride with (z)-tributyl(4-vinylstyryl)stannane via palladium-catalyzed Stille coupling.

4. The method as recited in claim 1 , wherein laminating a carbene-coated metal foil to the substrate includes laminating the carbene-coated metal foil to a prepreg comprising a sheet of woven glass fiber impregnated with the base polymer.

5. The method as recited in claim 1 , wherein the carbene-coated metal foil comprises an electrodeposited copper foil having a copper surface treated with the NHC compound.

6. The method as recited in claim 5 , wherein the copper surface of the electrodeposited copper foil is smooth and non-oxidized.

7. The method as recited in claim 2 , wherein laminating a carbene-coated metal foil to the substrate includes laminating the carbene-coated metal foil to a prepreg comprising a sheet of woven glass fiber impregnated with the base polymer.

8. The method as recited in claim 2 , wherein the carbene-coated metal foil comprises an electrodeposited copper foil having a copper surface treated with the NHC compound.

9. The method as recited in claim 8 , wherein the copper surface of the electrodeposited copper foil is smooth and non-oxidized.

10. The method as recited in claim 3 , wherein laminating a carbene-coated metal foil to the substrate includes laminating the carbene-coated metal foil to a prepreg comprising a sheet of woven glass fiber impregnated with the base polymer.

11. The method as recited in claim 3 , wherein the carbene-coated metal foil comprises an electrodeposited copper foil having a copper surface treated with the NHC compound.

12. The method as recited in claim 11 , wherein the copper surface of the electrodeposited copper foil is smooth and non-oxidized.

Assignees

• IBM

Inventors

• Boday Dylan J
• Kuczynski Joseph
• Wertz Jason T
• Zhang Jing

Classifications

• B32B2260/021

  Fibrous or filamentary layer · CPC title

• B32B15/08

  of synthetic resin · CPC title

• B32B7/12

  using interposed adhesives or interposed materials with bonding properties · CPC title

• H05K2203/122

  Organic non-polymeric compounds, e.g. oil, wax or thiol · CPC title

• B32B2255/24

  Organic non-macromolecular coating · CPC title