IP Library Granted Patent US 9,608,206
Granted Patent B2
US 9,608,206 · App. 14/135,191 · Granted Mar 28, 2017

Organic electroluminescent materials and devices

Inventors: Jason Brooks (Philadelphia, PA); Chuanjun Xia (Lawrenceville, NJ); Raymond Kwong (Plainsboro, NJ); James Fiordeliso (Morrisville, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0054C07C15/38C07D307/91C07D333/76C07D409/04C09B57/00C09K11/06H01L51/004H01L51/0061H01L51/0085H05B33/14C07C2103/42C09K2211/1007C09K2211/1011H01L51/0059H01L51/0081H01L51/5016H01L51/5024
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Quick Facts
Patent No.
US 9,608,206
App. No.
14/135,191
Granted
Mar 28, 2017
Kind
B2
Abstract

Disclosed is an organic electroluminescent device including an anode, a cathode, and an emissive layer between the anode and the cathode, the emissive layer including a phosphorescent material and a compound having a repeat unit that contains a novel triphenylene moiety. A preferred group of the novel triphenylene moiety are triphenylenes that are substituted with a non-fused aryl group having one or more meta-substituents, where each meta-substituent is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups. A further preferred group of compounds are triphenylenes that are substituted with a non-fused heteroaryl group having one or more meta-substituents, where each meta-substituent is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups. The compounds may be useful in phosphorescent organic light emitting devices.

Claims (35)

1. An organic light emitting device, comprising:

an anode;

a cathode;

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a triphenylene core of Formula I:

wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, or a non-fused aryl group having one or more meta-substituents,

wherein each meta-substituent is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups, and

wherein at least one of R 1 , R 2 , and R 3 is a non-fused aryl group having at least one meta-substituent that is a non-fused aryl group further substituted with one or more non-fused aryl groups.

2. The organic light emitting device of claim 1 , wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl groups.

3. The organic light emitting device of claim 1 , wherein the organic layer is an emitting layer having a host and an emissive dopant, and the compound comprising a triphenylene core of Formula I is the host.

4. The organic light emitting device of claim 1 , wherein the compound comprising a triphenylene core of Formula I comprising any one of substructures F through O:

wherein each of R′ 1-6 is independently a hydrogen, or a non-fused aryl group, optionally substituted with R a , wherein in each of the substructures at least one of R′ 1-6 is a non-fused aryl group substituted with R a , wherein R a is a non-fused aryl a branched or straight chain of non-fused aryls or alkyl substituted aryl.

5. The organic light emitting device of claim 4 , wherein the compound having the substructure F

wherein R′ 1 is a straight or branched chain of two or more non-fused aryl groups.

6. The organic light emitting device of claim 4 , wherein the compound having the substructure F is selected from the group consisting of:

7. A compound comprising a triphenylene core of Formula I:

wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, or a non-fused aryl group having one or more meta-substituents;

wherein each meta-substituent is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups; and

wherein at least one of R 1 , R 2 , and R 3 is a non-fused aryl group having at least one meta-substituent that is a non-fused aryl group further substituted with one or more non-fused aryl groups.

8. The compound of claim 7 , wherein at least one meta-substituent is substituted with a chain of at least two non-fused aryl groups.

9. The compound of claim 7 , wherein at least two of R 1 , R 2 , and R 3 are each a non-fused aryl group having at least one meta-substituent that is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups.

10. The compound of claim 7 , wherein each of R 1 , R 2 , and R 3 includes no more than three para-substituted phenyl rings.

11. The compound of claim 7 having no more than three para-substituted phenyl rings including the phenyl rings of the triphenylene core.

12. The compound of claim 7 comprising any one of substructures F-O:

wherein each of R′ 1-6 is independently a hydrogen, or a non-fused aryl group, optionally substituted with R a , wherein in each of the substructures at least one of R′ 1-6 is a non-fused aryl group substituted with R a , wherein R a is a non-fused aryl a branched or straight chain of non-fused aryls or alkyl substituted aryl.

13. A compound selected from the group consisting of:

wherein each of R′ 1 , R′ 2 , R′ 3 , and R′ 4 is an unsubstituted non-fused aryl group.

14. The compound of claim 13 , wherein the compound is selected from the group consisting of:

15. The compound of claim 7 having substructure F:

wherein R′ 1 is a straight or branched chain of two or more non-fused aryl groups.

16. The compound of claim 15 , wherein the compound is any one of:

17. The compound of claim 12 having substructure F:

wherein R′ 1 is a non-fused aryl group substituted with at least one alkyl substituted phenyl group.

18. The compound of claim 17 , wherein R′ 1 is a non-fused aryl group substituted with two alkyl substituted phenyl groups.

19. The compound of claim 18 , wherein the compound is:

20. The compound of claim 7 , wherein the compound is:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2013
From: BROOKS, JASON; XIA, CHUANJUN; KWONG, RAYMOND; FIORDELISO, JAMES
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 031826/0761 →
Continuity (4)
Continuation 12865628
Provisional Application 61017506 · Dec 28, 2007
Provisional Application 60963944 · Aug 8, 2007
Related Publication 20140103327A1 · Apr 17, 2014