Polymeric resin for dielectric applications

Patent metadata

Field	Value
Publication number	US-2021198395-A1
Application number	US-202017106277-A
Country	US
Kind code	A1
Filing date	Nov 30, 2020
Priority date	Dec 30, 2019
Publication date	Jul 1, 2021
Grant date	—

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.

First claim

What is claimed is:

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

2 . The polymer of claim 1 , wherein the mixture comprises (a) 20-40 mol % of arylcyclobutene monomer.

3 . The polymer of claim 1 , wherein the arylcyclobutene monomer has a structure selected from the group consisting of Formula A-1 and Formula A-2,

where:
K 1 is a divalent group selected from the group consisting of alkyl, aryl, carbocyclic aryl, polycyclic aryl, heteroaryl, aryloxy, arylalkyl, carbonyl, ester, carboxyl, ether, thioester, thioether, tertiary amine, and combinations thereof;
K 2 is a single bond or a divalent group selected from the group consisting of alkyl, aryl, carbocyclic aryl, polycyclic aryl, heteroaryl, aryloxy, arylalkyl, carbonyl, ester, carboxyl, and ether, thioester, thioether, tertiary amine, and combinations thereof;
L 1 is a covalent bond or a multivalent linking group;
M is a substituted or unsubstituted divalent aromatic radical group, or a substituted or unsubstituted divalent heteroaromatic radical group;
R 1 -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;
x and y are the same or different and are an integer from 1 to 5, wherein when L 1 is a covalent bond, y=1.

4 . The polymer of claim 3 , wherein the arylcyclobutene monomer has Formula A-1-a,

where:
Ar is a substituted or unsubstituted carbocyclic aryl or a substituted or unsubstituted heteroaryl group;
Q is a covalent bond, O, S, or NW;
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.

5 . The polymer of any one of claim 1 , wherein the mixture comprises (b) 15-30 mol % of the diene monomer.

6 . The polymer of claim 5 , wherein the mixture comprises (b) 20-25 mol % of the diene monomer.

7 . The polymer of claim 1 , wherein the 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.

8 . The polymer of claim 1 , wherein the mixture comprises (c) 40-60 mol % of the aromatic vinyl monomer.

9 . The polymer of claim 1 , wherein the 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.

10 . The polymer of claim 1 , wherein the mixture further comprises (d) 3-10 mol % of at least one addition polymerizable vinyl substituted C 3-12 heterocycle monomer.

11 . The polymer of claim 10 , wherein the heterocycle monomer is selected from the group consisting of N-heterocycles, S-heterocycles, N,S-heterocycles, and substituted derivatives thereof.

12 . The polymer of claim 10 , wherein the 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.

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

14 . The liquid composition of claim 13 , 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, N-butyl-2-pyrrolidone.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Hayes Colin
• Calabrese Colin
• Gallagher Michael K
• Barr Robert K

Classifications

• C08F236/04

  conjugated · CPC title

• C08F236/02

  the radical having only two carbon-to-carbon double bonds · CPC title

• C08F226/12

  N-Vinylcarbazole · CPC title

• C08F212/08 Primary

  Styrene · CPC title

• C08F212/04

  containing one ring · CPC title