IP Library Granted Patent US 8,373,287
Granted Patent B2
US 8,373,287 · App. 13/058,688 · Granted Feb 12, 2013

Polymeric compositions comprising per(phenylethynyl) arene derivatives

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Quick Facts
Patent No.
US 8,373,287
App. No.
13/058,688
Granted
Feb 12, 2013
Kind
B2
Abstract

A polymeric composition comprising a first polymer chosen from a poly(arylene ether) polymer including polymer repeat units of the following structure: —(O—Ar 1 —O—Ar 2 —O—) m —(—O—Ar 3 —O—Ar 4 —O)n- where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different aryl radicals, m is 0 to 1, n is 1 m; a polysulfone, a polyimide, a poly(etherketone), a polyurea, a polyurethane, and combinations thereof and a second polymer comprising a per(phenylethynyl) arene polymer derivative. Cured films containing the polymer can exhibit at least one of the following properties: Tg from 160° C. to 180° C., a dielectric constant below 2.7 with frequency independence, and a maximum moisture absorption of less than 0.17 wt %. Accordingly, the polymer is especially useful, for example, in interlayer dielectrics and in die-attach adhesives.

Claims (26)

1. A composition comprising:

a first polymer chosen from a poly(arylene ether) polymer including polymer repeat units of the following structure:

—(O—Ar 1 —O—Ar 2 —O—) m —(—O—Ar 3 —O—Ar 4 —O) n —

where Ar 1 , Ar 2 , Ar 3 , and Ar 4 are identical or different aryl radicals, m is 0 to 1, n is 1−m; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; and combinations thereof; and

a second polymer comprising a per(phenylethynyl)arene polymer derivative.

2. The composition of claim 1 , wherein the aryl radicals are independently selected from the group consisting of:

3. A polymer composition comprising:

a first polymer chosen from a polymer poly(arylene ether) polymer having a graft which graft can be thermally induced to crosslink the polymer, wherein said polymer having said graft has the structure:

wherein m=0 to 1.0; and n=1.0−m; and Ar 1 , Ar 2 , Ar 3 and Ar 4 are individually arylene radicals, and G 1-8 are individually: H,

or mixtures thereof, wherein Z is the average number of G radicals which are I or II per repeating unit of said polymer and Z is in the range of 0.1 to 4.0, where R 1 , R 2 , R 3 and R 4 are individually H or alkoxy radical, wherein the alkoxy radical can have a normal or branched alkyl radical of C 1-8 , and further wherein said poly(arylene ether) polymer consists essentially of non-functional repeating units wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 are individually arylene radicals selected from the group consisting of;

and mixtures thereof, but Ar 1 and Ar 2 or Ar 3 and Ar 4 , other than the diradical 9,9-diphenylfluorene, are not isomeric equivalents; a polysulfone; a polyimide; a polyamide; a poly(etherketone); a polyurea; a polyurethane; and combinations thereof; and

a second polymer comprising a per(phenylethynyl)arene polymer derivative.

4. The composition of claim 3 wherein the grafted polymer has repeating units of a structure:

wherein G 1-8 are as defined above; m=0 to 1.0; and n=1.0−m; and Ar 2 and Ar 4 are individually arylene radicals selected from the group consisting of;

and mixtures thereof.

5. The composition of claim 4 wherein the grafted polymer comprises a repeating polymer unit:

wherein grafts G 1-4 are individually selected from the group consisting of: H,

and mixtures thereof, where Z is the average number of G radicals per polymer unit and Z is in the range of 0.1 to 4.0.

6. The composition of claim 3 wherein the grafted polymer has a repeating polymer unit:

wherein G 1-4 are individually H or:

where Z is the average number of G radicals per polymer unit and Z is in the range of 0.1 to 4.0.

7. The composition of claim 6 wherein Z is in the range of 0.25 to 1.5.

8. The composition of claim 7 wherein Z is approximately 0.9.

9. The composition of claim 3 wherein said composition is crosslinked and comprises a dielectric material on a microelectronic device.

10. The composition of claim 9 wherein said dielectric material is provided adjacent conductive regions of an integrated circuit.

11. The composition of claim 3 wherein said polymer and said graft are crosslinked.

Assignments (6)
CORRECTIVE ASSIGNMENT TO CORRECT THE DECLARATION PREVIOUSLY RECORDED AT REEL: 059510 FRAME: 0251. ASSIGNOR(S) HEREBY CONFIRMS THE DECLARATION . Recorded May 18, 2022
From: DELSPER LP
To: DELSPER LP
Reel/Frame 060982/0951 →
CORRECTIVE ASSIGNMENT TO CORRECT THE DECLARATION LIST OF PATENTS PREVIOUSLY RECORDED AT REEL: 027974 FRAME: 0346. ASSIGNOR(S) HEREBY CONFIRMS THE DECLARATION . Recorded Mar 25, 2022
From: DELSPER LP
To: DELSPER IP
Reel/Frame 059510/0251 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2017
From: AIR PRODUCTS AND CHEMICALS, INC.
To: VERSUM MATERIALS US, LLC
Reel/Frame 041772/0733 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2013
From: GREENE, TWEED IP, INC.
To: DELSPER LP
Reel/Frame 031679/0008 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2012
From: AIR PRODUCTS AND CHEMICALS, INC.
To: GREENE, TWEED IP, INC.
Reel/Frame 027974/0346 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2011
From: BURGOYNE, WILLIAM FRANKLIN, JR.; CONNER, MARK DAVID; NORDQUIST, ANDREW FRANCIS; COLLINS, WILLIAM STEVEN
To: AIR PRODUCTS AND CHEMICALS, INC.
Reel/Frame 026257/0554 →