IP Library Granted Patent US 9,112,157
Granted Patent B2
US 9,112,157 · App. 13/894,412 · Granted Aug 18, 2015

Hole transport materials including OLED applications

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Quick Facts
Patent No.
US 9,112,157
App. No.
13/894,412
Granted
Aug 18, 2015
Kind
B2
Abstract

The composition described here comprises at least one hole-transporting compound, wherein the hole-transporting compound comprises a core covalently bonded to at least two arylamine groups, wherein the arylamine group optionally comprises one or more intractability groups. The composition can provide good film formation and stability when coated onto hole injection layers. Solution processing of hole transporting layers of OLEDs can be achieved with the composition described here. Good mobility can be achieved.

Claims (28)

1. A composition comprising at least one hole transporting compound, said hole transporting compound comprises a hole transporting core covalently bonded to one or more arylamine (AA) groups, each AA group is optionally substituted with one or more intractability groups, wherein the hole transporting compound is represented by:

wherein each of X 11 is S, O, NR, CR 2 , SiR 2 or GeR 2 , wherein each R is an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group, and wherein each of R 29 is H, F, or an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group, and

wherein the arylamine group is a diarylamine or triarylamine group substituted with one or more vinyl groups.

2. The composition of claim 1 , wherein the arylamine group is

3. A composition comprising at least one hole transporting compound, said hole transporting compound comprises a hole transporting core covalently bonded to one or more arylamine (AA) groups, each AA group is optionally substituted with one or more intractability groups, wherein the hole transporting compound is represented by:

wherein each of X 11 is S, O, NR, CR 2 , SiR 2 or GeR 2 , wherein each R is an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group, and wherein each of R 29 is H, F, or an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group,

wherein the hole transporting compound comprises at least two intractability groups.

4. A composition comprising at least one hole transporting compound, said hole transporting compound comprises a hole transporting core covalently bonded to one or more arylamine (AA) groups, each AA group is optionally substituted with one or more intractability groups, wherein the hole transporting compound is represented by:

wherein each of X 11 is S, O, NR, CR 2 , SiR 2 or GeR 2 , wherein each R is an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group, and wherein each of R 29 is H, F, or an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group,

wherein the hole transporting compound comprises at least two intractability groups, wherein the intractability groups are crosslinking groups or polymerizable groups.

5. The composition of claim 3 , wherein the hole transporting compound comprises at least two intractability groups, wherein the intractability groups are non-crosslinking groups.

6. The composition of claim 3 , wherein the hole transporting compound comprises at least two intractability groups selected from the group consisting of

7. The composition of claim 3 , further comprising at least one solvent.

8. The composition of claim 3 , further comprising a second compound comprising one or more intractability groups.

9. A composition comprising a partially or fully reacted form of the composition of claim 3 .

10. A device comprising a hole transport layer, wherein the hole transport layer comprises the composition of claim 9 .

11. The device of claim 10 , wherein the device is an OLED device.

12. The composition of claim 1 , wherein the hole transporting compound is represented by

wherein each of X 11 is S, O, NR, CR 2 , SiR 2 or GeR 2 , and wherein each R is an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group.

13. The composition of claim 1 , wherein the hole transporting compound is represented by

wherein each R is an optionally substituted alkyl, aryl, heteroalkyl, heteroaryl, or intractability group.

14. The composition of claim 3 , wherein the arylamine (AA) group is a diarylamine or triarylamine group optionally substituted with one or more intractability groups.

15. A composition comprising a partially or fully reacted form of the composition of claim 1 .

16. A composition comprising a partially or fully reacted form of the composition of claim 4 .

17. A composition comprising a partially or fully reacted form of the composition of claim 5 .

18. A composition according to claim 1 , wherein the X 11 group is CR 2 .

19. A composition according to claim 3 , wherein the X 11 group is CR 2 .

20. A composition according to claim 4 , wherein the X 11 group is CR 2 .

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: SOLVAY USA, INC.
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 039767/0225 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0641 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0619 →
RELEASE OF SECURITY INTEREST Recorded Mar 31, 2014
From: SOLVAY AMERICA, INC.
To: PLEXTRONICS, INC.
Reel/Frame 032568/0742 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2014
From: PLEXTRONICS, INC.
To: SOLVAY USA INC.
Reel/Frame 032568/0780 →
SECURITY AGREEMENT Recorded Jan 30, 2014
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 032141/0680 →
SECURITY AGREETMENT Recorded Sep 23, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 031347/0336 →
SECURITY AGREEMENT Recorded May 24, 2013
From: PLEXTRONICS, INC.
To: SOLVAY AMERICA, INC.
Reel/Frame 030486/0137 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2013
From: BROWN, CHRISTOPHER T.; GAVIN, AMANDA; GRENIER, CHRISTOPHE RENE GASTON; KNITTEL, CHRISTOPHER R.; MIRANDA, VICTOR; WANG, JING
To: PLEXTRONICS, INC.
Reel/Frame 030457/0878 →