IP Library › Granted Patent US 10,879,467
Granted Patent B2
US 10,879,467 · App. 16/519,476 · Granted Dec 29, 2020

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)
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 10,879,467
App. No.
16/519,476
Granted
Dec 29, 2020
Kind
B2
Abstract

A hole transport copolymer having the following Formula III is disclosed herein: In some embodiments, A is a monomeric unit having Formula Ia or Formula IIa, B is a B is a monomeric unit having at least three points of attachment in the copolymer, E is the same or different at each occurrence and is selected from the group consisting of H, D, halide, alkyl, aryl, arylamino, siloxane, crosslinkable groups, deuterated alkyl, deuterated aryl, deuterated arylamino, deuterated siloxane, and deuterated crosslinkable groups, and x, y, and z are the same or different and are mole fractions, such that x+y+z=1, and x and y are non-zero.

Claims (23)

1. A hole transport copolymer having Formula III

wherein:

A is a monomeric unit having Formula Ia or Formula IIa;

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;

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;

# is a point of attachment to other monomeric units;

B is a monomeric unit having at least three points of attachment in the copolymer;

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

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;

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, ester, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aryl, deuterated heteroaryl, deuterated amino, deuterated silyl, deuterated germyl, deuterated ester, 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;

# is a point of attachment to other monomeric units; and

x, y, and z are the same or different and are mole fractions, such that x+y+z=1, and x and y are non-zero.

2. The hole transport copolymer 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 copolymer according to claim 1 , in which the molar ratio of A+B to E is in the range of 50:50 to 90:10.

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

5. 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 copolymer according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 049865/0093 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2019
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 049848/0274 →
Continuity (5)
Division 15528189
Provisional Application 62251405 · Nov 5, 2015
Provisional Application 62157531 · May 6, 2015
Provisional Application 62082232 · Nov 20, 2014
Related Publication 20190348607A1 · Nov 14, 2019
Cited By (1)
US 12,727,375