IP Library › Granted Patent US 10,439,140
Granted Patent B2
US 10,439,140 · App. 15/528,189 · Granted Oct 8, 2019

Hole transport materials

Inventors: Nora Sabina Radu (Landenberg, PA); Kerwin D. Dobbs (Wilmington, DE); Adam Fennimore (Wilmington, DE); Weiying Gao (Landenberg, PA); Gene M. Rossi (Wilmington, DE); Juergen Weber (Lincoln University, PA)
Assignee: LG Chem, Ltd.
H01L51/0035C08G61/12C08G61/124H01L51/0043C08G2261/124C08G2261/148C08G2261/1412C08G2261/1646C08G2261/312C08G2261/3162C08G2261/3241C08G2261/41C08G2261/512C08G2261/95H01L51/5056
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Quick Facts
Patent No.
US 10,439,140
App. No.
15/528,189
Granted
Oct 8, 2019
Kind
B2
Abstract

There is provided a hole transport polymer having a carbazole group and an amino nitrogen having Formula I In the formula: Ar 1 , Ar 2 , and Ar 4 are the same or different and are substituted or unsubstituted aryl groups or deuterated aryl groups; Ar 3 is substituted or unsubstituted aryl groups or deuterated aryl groups; E is the same or different at each occurrence and is selected from the group consisting of H, D, halide, alkyl, aryl, siloxane, deuterated alkyl, deuterated aryl, deuterated siloxane, and a crosslinking group; R 1 -R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, amino, silyl, germyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated aryloxy, deuterated fluoroalkoxy, deuterated siloxane, deuterated siloxy, and crosslinking groups, wherein adjacent groups selected from R 1 and R 2 can be joined together to form a fused ring; a is an integer from 0-4; b is an integer from 0-3; and n is an integer greater than or equal to 1.

Claims (21)

1. A hole transport homopolymer having a carbazole group and an amino nitrogen, wherein said hole transport homopolymer has Formula I or Formula II

wherein:

Ar 1 , Ar 2 , and Ar 4 are the same or different and are substituted or unsubstituted aryl groups or deuterated aryl groups;

Ar 3 is substituted or unsubstituted aryl groups or deuterated aryl groups;

E is the same or different at each occurrence and is selected from the group consisting of H, D, halide, alkyl, aryl, siloxane, deuterated alkyl, deuterated aryl, deuterated siloxane, and a crosslinking group;

R 1 -R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, amino, silyl, germyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated aryloxy, deuterated fluoroalkoxy, deuterated siloxane, deuterated siloxy, and crosslinking groups, wherein adjacent groups selected from R 1 and R 2 can be joined together to form a fused ring;

a is an integer from 0-4;

b is an integer from 0-3; and

n is an integer greater than 10;

wherein:

Ar 1 , Ar 2 , Ar 2a , Ar 4 , and Ar 4a are the same or different and are substituted or unsubstituted aryl groups or deuterated aryl groups;

Ar 3 and Ar 3a are substituted or unsubstituted aryl groups or deuterated aryl groups;

E is the same or different at each occurrence and is selected from the group consisting of H, D, halide, alkyl, aryl, siloxane, deuterated alkyl, deuterated aryl, deuterated siloxane, and a crosslinking group;

R 1 -R 2 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aryl, heteroaryl, amino, silyl, germyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated aryloxy, deuterated fluoroalkoxy, deuterated siloxane, deuterated siloxy, and crosslinking groups, wherein adjacent groups selected from R 1 and R 2 can be joined together to form a fused ring;

b is an integer from 0-3; and

n is an integer greater than 10.

2. The hole transport homopolymer according to claim 1 , in which Ar 1 -Ar 4 are aryl groups at least one of which is further substituted with additional groups.

3. The hole transport homopolymer according to claim 2 , in which the additional groups on the aryl groups are alkyl groups having 1 to 6 carbon atoms.

4. The hole transport homopolymer according to claim 1 , in which at least one of a and b does not equal zero.

5. The hole transport homopolymer according to claim 1 , in which the hole transport homopolymer contains at least one D.

6. An organic electronic device comprising an anode, a cathode, and at least one organic active layer therebetween, wherein the organic active layer comprises a hole transport homopolymer according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 049226/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2017
From: RADU, NORA SABINA; DOBBS, KERWIN D; FENNIMORE, ADAM; GAO, WEIYING; ROSSI, GENE M; WEBER, JUERGEN
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 043922/0471 →
Continuity (4)
Provisional Application 62082232 · Nov 20, 2014
Provisional Application 62157531 · May 6, 2015
Provisional Application 62251405 · Nov 5, 2015
Related Publication 20170358750A1 · Dec 14, 2017
Cited By (1)
US 12,727,375