IP Library Granted Patent US 11,603,422
Granted Patent B2
US 11,603,422 · App. 17/106,277 · Granted Mar 14, 2023

Polymeric resin for dielectric applications

Inventors: Colin Hayes (Hudson, MA); Colin Calabrese (Marlborough, MA); Michael K Gallagher (Hopkinton, MA); Robert K Barr (Shrewsbury, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
C08F212/32C08F212/12C08F226/06C08F228/06C08F236/02C08F212/04C08F212/08C08F226/12C08F236/04
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Quick Facts
Patent No.
US 11,603,422
App. No.
17/106,277
Granted
Mar 14, 2023
Kind
B2
Abstract

There is provided a polymer which is the copolymerization product from a mixture including: (a) 10-50 mol % of at least one addition polymerizable arylcyclobutene monomer; (b) 15-50 mol % of at least one addition polymerizable diene monomer; and (c) 15-60 mol % of at least one addition polymerizable aromatic vinyl monomer. The polymer can be used in electronic applications.

Claims (28)

1. A polymer comprising a copolymerization product from a mixture comprising:

(a) 10-50 mol %, based on the total monomers present in the copolymerization, of at least one addition polymerizable arylcyclobutene monomer of Formula A-1-a,

wherein:

Ar is a substituted or unsubstituted carbocyclic aryl or a substituted or unsubstituted heteroaryl group;

Q is a covalent bond, O, S, or NR a ;

R a is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted carbocyclic aryl, and substituted or unsubstituted heteroaryl;

R 5 -R 7 are the same or different and are independently selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, a substituted or unsubstituted carbocyclic aryl group, and a substituted or unsubstituted heteroaryl group;

R 8 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, a substituted or unsubstituted carbocyclic aryl group, and a substituted or unsubstituted heteroaryl group; and

a is an integer from 0 to 4;

(b) 15-50 mol %, based on the total monomers present in the copolymerization, of at least one addition polymerizable diene monomer;

(c) 15-60 mol %, based on the total monomers present in the copolymerization, of at east one addition polymerizable aromatic vinyl monomer; and

(d) 3-10 mol %, based on the total monomers present in the copolymerization, of at least one addition polymerizable vinyl substituted C 3-12 heterocycle monomer.

2. The polymer of claim 1 , wherein the mixture comprises (a) 20-40 mol %, based on the total monomers present in the copolymerization, of the at least one arylcyclobutene monomer.

3. The polymer of claim 1 , wherein the mixture comprises (b) 15-30 mol %, based on the total monomers present in the copolymerization, of the at least one diene monomer.

4. The polymer of claim 3 , wherein the mixture comprises (b) 20-25 mol %, based on the total monomers present in the copolymerization, of the at least one diene monomer.

5. The polymer of claim 1 , wherein the at least one diene monomer has Formula B,

where:

R 9 is the same or different at each occurrence and is selected from hydrogen and methyl; and

R 10 is the same or different at each occurrence and is selected from the group consisting of hydrogen, C 1-5 alkyl, C 1-5 alkoxy, C 1-5 thioalkyl, and C 5-12 alkenyl.

6. The polymer of claim 1 , wherein the mixture comprises (c) 40-60 mol %, based on the total monomers present in the copolymerization, of the at least one aromatic vinyl monomer.

7. The polymer of claim 1 , wherein the at least one aromatic vinyl monomer has Formula C

where:

R 12 -R 14 are the same or different at each occurrence and is selected from the group consisting of hydrogen and C 1-5 alkyl; and

R 15 is the same or different at each occurrence and is selected from the group consisting of hydrogen and C 1-5 alkyl, where adjacent R 15 groups can be joined to form a fused 6-membered aromatic ring.

8. The polymer of claim 1 , wherein the at least one heterocycle monomer is selected from the group consisting of N-heterocycles, S-heterocycles, N,S-heterocycles, and derivatives thereof substituted with one or more of a C 1-6 alkyl, a C 6-12 carbocyclic aryl, or a C 3-12 heteroaryl.

9. The polymer of claim 1 , wherein the at least one vinyl substituted C 3-12 heterocycle is selected from the group consisting of 4-vinyl pyridine, 4-vinyl-1,3-diazine, 2-vinyl-1,3,5-triazine, and 4-methyl-5-vinyl-1,3-thiazole.

10. A liquid composition comprising the polymer of claim 1 and a solvent.

11. The liquid composition of claim 10 , wherein the solvent is selected from the group consisting of cyclopentanone, cyclohexanone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, gamma-butyrolactone, 3-methoxypropionate, dipropylene glycol dimethyl ether, 3-methoxybutyl acetate, anisole, mesitylene, 2-heptanone, cyrene, 2-butanone, ethyl lactate, amyl acetate, n-butyl acetate, N-methyl-2-pyrrolidone, and N-butyl-2-pyrrolidone.

Assignments (5)
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 May 3, 2021
From: BARR, ROBERT K.; CALABARESE, COLIN; GALLAGHER, MICHAEL K.; HAYES, COLIN
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 056120/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2021
From: BARR, ROBERT K.; CALABRESE, COLIN; GALLAGHER, MICHAEL K.; HAYES, COLIN
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 055858/0736 →
Continuity (2)
Provisional Application 62954732 · Dec 30, 2019
Related Publication 20210198395A1 · Jul 1, 2021