IP Library Granted Patent US 12,227,620
Granted Patent B2
US 12,227,620 · App. 17/594,424 · Granted Feb 18, 2025

Polymers for use in electronic devices

Inventors: Viacheslav V Diev (Wilmington, DE); Nora Sabina Radu (Landenberg, PA); Michael Henry Howard, Jr. (Montchanin, DE); Rakesh Nambiar (West Chester, PA)
Assignee: DUPONT ELECTRONICS, INC.
C08G73/1032C08G73/1075C08J5/18C08J2379/08
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Quick Facts
Patent No.
US 12,227,620
App. No.
17/594,424
Granted
Feb 18, 2025
Kind
B2
Abstract

Disclosed is a polyamic acid having Formula I In Formula I: R a represents one or more different tetracarboxylic acid component residues; R b represents one or more different aromatic diamine residues or aromatic diisocyanate residues; and 5-100 mol % of R b has Formula II In Formula II: R 1 through R 6 are the same or different and are haloalkyl or haloalkoxy; R 7 is the same or different at each occurrence and is deuterium, halogen, cyano, hydroxyl, alkyl, deuterated alkyl, heteroalkyl, alkoxy, heteroalkoxy, haloalkyl, haloalkoxy, silyl, siloxy, hydrocarbon aryl, substituted hydrocarbon aryl, heteroaryl, substituted heteroaryl, vinyl, or allyl; n is an integer from 0-10; x1 and x4 are the same or different and are an integer from 0-3; x2 and x3 are the same or different and are an integer from 0-2; and * indicates a point of attachment.

Claims (82)

1. A liquid composition comprising

(a) a polyamic acid having a repeat unit structure of Formula I

or Formula IV

where:

R a represents one or more different tetracarboxylic acid component residues; and

R b represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b has Formula II

R b1 represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b1 has Formula V

where:

R 1 through R 6 are the same or different and are selected from the group consisting of haloalkyl and haloalkoxy;

R 7 is the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, cyano, hydroxyl, alkyl, deuterated alkyl, heteroalkyl, alkoxy, heteroalkoxy, haloalkyl, haloalkoxy, silyl, siloxy, hydrocarbon aryl, substituted hydrocarbon aryl, heteroaryl, substituted heteroaryl, vinyl, and allyl;

wherein any of R 1 through R 7 can be joined together with another of R 1 through R 7 on an adjacent ring to form a fused 5- or 6-membered alicyclic ring;

n is an integer from 0-10;

x1 and x4 are the same or different and are an integer from 0-3;

wherein x1>0 or x4>0;

x2 and x3 are the same or different and are an integer from 0-2;

* indicates a point of attachment; and

(b) at least one high-boiling aprotic solvent;

wherein a 10 μm polyimide film made from the liquid composition has a Tg greater than 400° C. and a b* value less than 10.0.

2. The liquid composition according to claim 1 , wherein R 1 through R 6 are selected from the group consisting of a C 1-5 fluoroalkyl and a C 1-5 fluoroalkoxy.

3. The liquid composition according to claim 1 , wherein R 1 through R 6 are a C 1-5 perfluoroalkyl.

4. The liquid composition according to claim 1 , wherein R 7 is selected from the group consisting of deuterium, fluoro, alkyl, fluoroalkyl, alkoxy, and fluoroalkoxy.

5. The liquid composition according to claim 1 , wherein n=0.

6. The liquid composition according to claim 1 , wherein R a represents one or more residues from tetracarboxylic acid dianhydrides selected from the group consisting of PMDA, BPDA, s-BPDA, DSDA, 6FDA, TDA, BTDA, ODPA, and CpODA.

7. A polyimide film having a repeat unit structure of Formula III

or Formula VI

where:

R a represents one or more different tetracarboxylic acid component residues; and

R b represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b has Formula II

R b1 represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b1 has Formula V

where:

R 1 through R 6 are the same or different and are selected from the group consisting of halogen, haloalkyl, and haloalkoxy;

R 7 is the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, cyano, hydroxyl, alkyl, deuterated alkyl, heteroalkyl, alkoxy, heteroalkoxy, haloalkyl, haloalkoxy, silyl, siloxy, hydrocarbon aryl, substituted hydrocarbon aryl, heteroaryl, substituted heteroaryl, vinyl, and allyl;

wherein any of R 1 through R 7 can be joined together with another of R 1 through R 7 on an adjacent ring to form a fused 5- or 6-membered alicyclic ring;

n is an integer from 0-10;

x1 and x4 are the same or different and are an integer from 0-3;

wherein x1>0 or x4>0;

x2 and x3 are the same or different and are an integer from 0-2; and

* indicates a point of attachment;

wherein the polyimide film has a Tg greater than 400° C. and a b* value less than 10.0.

8. The polyimide film according to claim 7 , wherein the Tg greater than 430° C.

9. The polyimide film according to claim 7 , wherein R 1 through R 6 are selected from the group consisting of a C 1-5 fluoroalkyl and a C 1-5 fluoroalkoxy.

10. The polyimide film according to claim 7 , wherein R 1 through R 6 are a C 1-5 perfluoroalkyl.

11. The polyimide film according to claim 7 , wherein R 7 is selected from the group consisting of deuterium, fluoro, alkyl, fluoroalkyl, alkoxy, and fluoroalkoxy.

12. The polyimide film according to claim 7 , wherein n=0.

13. An organic electronic device having at least one layer comprising a polyimide film having a repeat unit of Formula III, according to claim 7 .

14. The electronic device according to claim 13 , wherein the layer is used in device components selected from the group consisting of device substrates, substrates for color filter sheets, cover films, and touch screen panels.

15. A liquid composition comprising

(a) a polyamic acid having a repeat unit structure of Formula I

or Formula IV

where:

R a represents one or more different tetracarboxylic acid component residues; and

R b represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b has Formula II

R b1 represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b1 has Formula V

where:

R 1 through R 6 are the same or different and are selected from the group consisting of haloalkyl and haloalkoxy;

R 7 is the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, cyano, hydroxyl, alkyl, deuterated alkyl, heteroalkyl, alkoxy, heteroalkoxy, haloalkyl, haloalkoxy, silyl, siloxy, hydrocarbon aryl, substituted hydrocarbon aryl, heteroaryl, substituted heteroaryl, vinyl, and allyl;

wherein any of R 1 through R 7 can be joined together with another of R 1 through R 7 on an adjacent ring to form a fused 5- or 6-membered alicyclic ring;

n is an integer from 3-10;

x1 and x4 are the same or different and are an integer from 0-3;

wherein x1>0 or x4>0;

x2 and x3 are the same or different and are an integer from 0-2;

* indicates a point of attachment; and

(b) at least one high-boiling aprotic solvent.

16. A polyimide film having a repeat unit structure of Formula III

or Formula VI

where:

R a represents one or more different tetracarboxylic acid component residues; and

R b represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b has Formula II

R b1 represents one or more different aromatic diamine residues or aromatic diisocyanate residues, wherein 5-100 mol % of R b1 has Formula V

where:

R 1 through R 6 are the same or different and are selected from the group consisting of halogen, haloalkyl, and haloalkoxy;

R 7 is the same or different at each occurrence and is selected from the group consisting of deuterium, halogen, cyano, hydroxyl, alkyl, deuterated alkyl, heteroalkyl, alkoxy, heteroalkoxy, haloalkyl, haloalkoxy, silyl, siloxy, hydrocarbon aryl, substituted hydrocarbon aryl, heteroaryl, substituted heteroaryl, vinyl, and allyl;

wherein any of R 1 through R 7 can be joined together with another of R 1 through R 7 on an adjacent ring to form a fused 5- or 6-membered alicyclic ring;

n is an integer from 3-10;

x1 and x4 are the same or different and are an integer from 0-3;

wherein x1>0 or x4>0;

x2 and x3 are the same or different and are an integer from 0-2; and

* indicates a point of attachment.

17. An organic electronic device having at least one layer comprising a polyimide film having a repeat unit of Formula VI, according to claim 16 .

18. An assembly comprising, in order, a cover layer, a touchscreen panel, an active display, a TFT layer, and a substrate, wherein a camera and optionally one or more sensors are on a side of the substrate opposite the TFT layer, and further wherein the substrate comprises a polyimide film according to claim 7 .

19. An assembly comprising, in order, a cover layer, a touchscreen panel, an active display, a TFT layer, and a substrate, wherein a camera and optionally one or more sensors are on a side of the substrate opposite the TFT layer, and further wherein the substrate comprises a polyimide film according to claim 16 .

20. The assembly of claim 18 , wherein the active display comprises an anode, a photoactive layer, and a cathode.

Assignments (3)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2023
From: DIEV, VIACHESLAV V; RADU, NORA SABINA; HOWARD, MICHAEL HENRY, JR; NAMBIAR, RAKESH
To: DUPONT ELECTRONICS, INC.
Reel/Frame 062972/0248 →