IP Library Granted Patent US 11,920,023
Granted Patent B2
US 11,920,023 · App. 17/731,690 · Granted Mar 5, 2024

Composite materials for dielectric applications

Inventors: Colin Hayes (Hudson, MA); Colin Calabrese (Marlborough, MA); Christine Hatter (Waltham, MA)
Assignee: Rohm and Haas Electronic Materials LLC.
C08L25/02C08L43/04C08L2201/02C08L2203/206C08L2312/00
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Quick Facts
Patent No.
US 11,920,023
App. No.
17/731,690
Granted
Mar 5, 2024
Kind
B2
Abstract

There is provided a dielectric composite material comprising (a) 20-50 weight % total solids of at least one thermosetting resin and other resin components; and (b) 50-70 weight % total solids of at least one inorganic particulate filler; where the at least one inorganic particulate filler is surface modified with one or more acrylic-based silane coupling agents.

Claims (48)

1. A dielectric composite material comprising:

(a) 20-50 weight % total solids of at least one thermosetting resin and other resin components; and

(b) 50-72 weight % total solids of at least one inorganic particulate filler;

where:

the at least one inorganic particulate filler is surface modified with one or more acrylic-based silane coupling agents; and

wherein the one or more acrylic-based silane coupling agents is combined with one or more polymeric silanes.

2. The dielectric composite material of claim 1 , wherein the thermosetting resin is an arylcyclobutene resin.

3. The dielectric composite material of claim 2 , wherein the at least one arylcyclobutene resin comprises a polymerization product from a mixture comprising (a) 10-50 mol % of one or more addition polymerizable arylcyclobutene monomers and one or more monomers selected from the group consisting of:

(b) 15-60% of one or more dienophile monomers;

(c) 15-50 mol % of one or more diene monomers; and

(d) up to 10 mol % of one or more heterocycle containing monomers.

4. The dielectric composite material of claim 3 , wherein the one or more addition polymerizable arylcyclobutene monomers has a structure selected from the group consisting of Formula (A-1), Formula (A-2), and Formula (A-3)

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;

K 3 is a polymerizable functional group;

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 4 are the same or different and are independently selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, akylthio, arylthiol, substituted alkyl amino, and substituted aryl amino;

R 5 -R 7 are the same or different and are independently selected from the group consisting of hydrogen, deuterium, cyano, halo, methyl, vinyl, allyl, and a substituted or unsubstituted isoprene having 1-100 carbon atoms;

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.

5. The dielectric composite material of claim 3 , wherein the one or more dienophile monomers has a structure given by Formula (II)

where:

B is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aromatic, substituted or unsubstituted heteroaromatic, substituted or unsubstituted alkyloxy, or hydroxy;

R 9 -R 11 are the same or different and are independently selected from the group consisting of hydrogen, vinyl, allyl, substituted or unsubstituted isoprene having 1-100 carbon atoms, substituted or unsubstituted alkyl group having 1 to 100 carbon atoms, halogen, cyano, substituted or unsubstituted aryl group having 6 to 100 carbon atoms, substituted or unsubstituted heteroaryl group having 6 to 100 carbon atoms, and combinations thereof.

6. The dielectric composite material of claim 3 , wherein the one or more diene monomers has a structure given by Formula (IV)

where:

R 16 is the same or different and are independently selected from the group consisting of hydrogen and methyl; and

R 17 is the same or different and are independently selected from the group consisting of hydrogen, C 1-5 alkyl, C 1-5 alkoxy, C 1-5 thioalkyl, and C 5-12 alkenyl.

7. The dielectric composite material of claim 3 , wherein the one or more heterocycle containing monomers is selected from the group consisting of vinyl substituted C 3-12 heterocycles and vinyl-substituted C 3-5 heterocycles.

8. The dielectric composite material of claim 1 , wherein the at least one inorganic particulate filler is selected from the group consisting of silica, alumina, boron nitride, glass, and quartz.

9. The dielectric composite material of claim 1 , wherein the one or more acrylic-based silane coupling agents is either in monomeric form or polymerized through a vinyl group.

10. The dielectric composite material of claim 9 , wherein the one or more acrylic-based silane coupling agents has a structure given by Formula (VII)

where:

R is the same or different at each occurrence and is selected from the group consisting of alkyl, aryl, acetyl, ketimino, and alkenyl;

X is a unsaturated group selected from the group consisting of acryloxy, methacryloxy, allyloxy, vinyl, maleimido, fumarate ester, maleate ester, ethynyl, phenylethynyl, stilbene, propiolate and phenylpropiolate ester; and

n is an integer from 1-10.

11. The dielectric composite material of claim 1 , wherein the one or more polymeric silanes has a structure given by Formula (VIII)

where:

R 27 is selected from the group consisting of alkyl and H;

R 28 is selected from the group consisting of alkyl and aryl, acetyl, ketimino, and alkenyl;

R 29 is selected from the group consisting of COOCH 2 CH═CH 2 , CH 3 , and H;

R 30 is selected from the group consisting of 4-allyloxyphenyl, COOCH 2 CH═CH 2 and any group containing a reactive dienophile;

X and Y are the same or different and are selected from the group consisting of methyl and H;

m and n are the same or different and are an integer from 10-1000;

o is an integer from 0-1000; and

p is an integer from 0-10.

12. A liquid composition comprising the dielectric composite material of claim 1 and one or more solvents.

Assignments (6)
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 Apr 2, 2024
From: THE DOW CHEMICAL COMPANY
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 066983/0061 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: HATTER, CHRISTINE; HAYES, COLIN
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 066261/0358 →
EMPLOYMENT AGREEMENT Recorded Jan 8, 2024
From: CALABRESE, COLIN
To: THE DOW CHEMICAL COMPANY
Reel/Frame 066222/0447 →
Cited By (1)
US 12,637,560