IP Library Granted Patent US 9,745,479
Granted Patent B2
US 9,745,479 · App. 14/922,393 · Granted Aug 29, 2017

Adhesion promoter

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Quick Facts
Patent No.
US 9,745,479
App. No.
14/922,393
Granted
Aug 29, 2017
Kind
B2
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.

Claims (20)

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.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2018
From: WANG, ZIDONG; GALLAGHER, MICHAEL K.; WANG, KEVIN Y.; PROKOPOWICZ, GREGORY P.
To: ROHM AND HAAS ELECTRONICS MATERIALS LLC
Reel/Frame 045045/0016 →