Adhesion promoter

Patent metadata

Field	Value
Publication number	US-9745479-B2
Application number	US-201514922393-A
Country	US
Kind code	B2
Filing date	Oct 26, 2015
Priority date	Oct 30, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

Compositions useful for improving the adhesion of coating compositions, such as dielectric film-forming compositions, include a hydrolyzed poly(alkoxysilane). These compositions are useful in methods of improving the adhesion of coating compositions to a substrate.

First claim

What is claimed is:

1. A composition comprising: an oligomer chosen from polyarylene oligomers, poly(cyclic-olefin) oligomers, arylcyclobutene oligomers, vinyl aromatic oligomers, and mixtures thereof; a poly(alkoxysilane) hydrolyzed with ≦1 mole % of water; and a solvent; wherein the composition comprises ≦1 mole % of alcohol of hydrolysis and wherein the poly(alkoxysilane) has from 2 to 6 alkoxysilane moieties.

2. The composition of claim 1 wherein the poly(alkoxysilane) is hydrolyzed with ≦0.5 mole % of water.

3. The composition of claim 1 wherein the poly(alkoxysilne) prior to being hydrolyzed has the formula:

wherein each R is independently chosen from (C 1 -C 6 )alkylidene, (C 1 -C 6 )alkylene, (C 6 -C 10 )arylene, and (C 2 -C 6 )alkenylene; each R 1 is independently chosen from H, (C 1 -C 6 )alkyl and (C 1 -C 6 )acyl; each Z is independently chosen from (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and —OR 1 ; X═(C 6 -C 10 )arylene, N(Y) or a covalent bond; Y═H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylene-N(Y 1 ) 2 , (C 2 -C 6 )alkenyl, (C 1 -C 6 )alkylene-Si(Z) 2 (OR 1 ), or aryl(meth)acryloyl; and Y 1 ═H, (C 1 -C 6 )alkyl, or (C 2 -C 6 )alkenyl; wherein each R is optionally substituted with one or more of (C 1 -C 6 )alkylidene-Si(Z) 2 (OR 1 ) and (C 1 -C 6 )alkylene-Si(Z) 2 (OR 1 ).

4. The composition of claim 1 wherein the arylcyclobutane oligomer has the formula:

wherein B is a n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; m is an integer of 1 or more; n is an integer of 1 or more; and R 5 is a monovalent group.

5. The composition of claim 1 having a mean particle size of ≦1 nm as determined by dynamic light scattering.

6. The composition of claim 1 wherein the oligomer is an arylcyclobutene oligomer.

7. A process for manufacturing a device, comprising:
providing a device substrate having a surface to be coated;
disposing a coating of the composition comprising: an oligomer chosen from polyarylene oligomers, poly(cyclic-olefin) oligomers, arylcyclobutene oligomers, vinyl aromatic oligomers, and mixtures thereof; a poly(alkoxysilane) hydrolyzed with ≦1 mole % of water; and a solvent; wherein the composition comprises ≦1 mole % of alcohol of hydrolysis and wherein the poly(alkoxysilane) has from 2 to 6 alkoxysilane moieties on the substrate surface; and
curing the coating.

8. The process of claim 7 wherein the device substrate is an electronic device substrate.

9. The process of claim 8 wherein the electronic device substrate comprises a surface comprising one or more of silicon, glass, ceramic, and metal.

10. The process of claim 7 wherein the poly(alkoxysilane) prior to being hydrolyzed has the formula:

wherein each R is independently chosen from (C 1 -C 6 )alkylidene, (C 1 -C 6 )alkylene, (C 6 -C 10 )arylene, and (C 2 -C 6 )alkenylene; each R 1 is independently chosen from H, (C 1 -C 6 )alkyl and (C 1 -C 6 )acyl; each Z is independently chosen from (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and —OR 1 ; X═(C 6 -C 10 )arylene, O, S, S—S, S—S—S, S—S—S—S, N(Y), P(Y), or a covalent bond; Y═H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylene-N(Y 1 ) 2 , (C 2 -C 6 )alkenyl, (C 1 -C 6 )alkylene-Si(Z) 2 (OR 1 ), or aryl(meth)acryloyl; and Y 1 ═H, (C 1 -C 6 )alkyl, or (C 2 -C 6 )alkenyl; wherein each R is optionally substituted with one or more of (C 1 -C 6 )alkylidene-Si(Z) 2 (OR 1 ) and (C 1 -C 6 )alkylene-Si(Z) 2 (OR 1 ).

11. The process of claim 7 wherein the oligomer is an arylcyclobutene oligomer.

12. The process of claim 11 wherein the arylcyclobutane oligomer has the formula:

wherein B is a n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; m is an integer of 1 or more; n is an integer of 1 or more; and R 5 is a monovalent group.

13. The process of claim 7 wherein the adhesion promoting composition has a mean particle size of ≦1 nm, as determined by dynamic light scattering.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Wang Zidong
• Gallagher Michael K
• Wang Kevin Y
• Prokopowicz Gregory P

Classifications

• H10P14/6506

  Formation of intermediate materials · CPC title

• H10P14/6342

  Liquid deposition, e.g. spin-coating, sol-gel techniques or spray coating · CPC title

• H10P14/683

  carbon-based polymeric organic materials, e.g. polyimides, poly cyclobutene or PVC · CPC title

• H10P95/00

  Generic processes or apparatus for manufacture or treatments not covered by the other groups of this subclass · CPC title

• C08G2261/3422

  conjugated, e.g. PPV-type · CPC title