IP Library Granted Patent US 9,034,483
Granted Patent B2
US 9,034,483 · App. 12/559,764 · Granted May 19, 2015

Phosphorescent materials

Inventors: Bert Alleyne (Ewing, NJ); Raymond Kwong (Plainsboro, NJ); Walter Yeager (Yardley, PA); Chuanjun Xia (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0085C09K11/06C09K2211/1029C09K2211/185C07F15/0033H01L51/5016
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,034,483
App. No.
12/559,764
Granted
May 19, 2015
Kind
B2
Abstract

Phosphorescent materials and devices having high efficiency and stability, narrow spectrum, and improved processibility. In particular, iridium complexes containing acac-derived ligands with branched alkyl substituents with branching at a position further than the α position to the carbonyl group, were found to be suitable for use as emitters in OLED devices.

Claims (53)

1. A compound having the formula:

wherein A and B are coordinated to the metal via a nitrogen atom on ring A and an sp 2 hybridized carbon atom on ring B;

wherein each of R a and R b represent no substitution, or one or more substituents independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups, wherein the one or more substituents can join to form fused rings;

wherein R z represents no substitution, alkyl, heteroalkyl, aryl, or heteroaryl group;

wherein R x and R y are each independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups and contain a branched alkyl moiety with branching at a position further than the α position to the carbonyl group; and

wherein n is 1 or 2;

wherein A-B is selected from the group consisting of:

wherein X is N—R, O or S; and

wherein R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl groups.

2. The compound of claim 1 , wherein the compound is:

3. The compound of claim 2 , wherein R x and R y are an isobutyl group.

4. The compound of claim 3 , wherein R z is hydrogen.

5. The compound of claim 4 , wherein the compound is selected from the group consisting of:

6. The compound of claim 3 , wherein R z is methyl.

7. The compound of claim 6 , wherein the compound is:

8. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound having the formula:

wherein A and B are coordinated to the metal via a nitrogen atom on ring A and an sp 2 hybridized carbon atom on ring B;

wherein each of R a and R b represent no substitution, or one or more substituents;

wherein when R a and R b are one or more substituents, R a and R b are each independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups;

wherein R z represents no substitution, alkyl, heteroalkyl, aryl, or heteroaryl group;

wherein R x and R y are each independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups and contain a branched alkyl moiety with branching at a position further than the α position to the carbonyl group; and

wherein n is 1 or 2;

wherein A-B is selected from the group consisting of:

wherein X is N—R, O or S; and

wherein R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl groups.

9. The device of claim 8 , wherein the compound is:

10. The device of claim 9 , wherein R x and R y are an isobutyl group.

11. The device of claim 10 , wherein R z is hydrogen.

12. The device of claim 11 , wherein the compound is selected from the group consisting of:

13. The device of claim 10 , wherein R z is methyl.

14. The device of claim 13 , wherein the compound is:

15. The device of claim 8 , wherein the organic layer is an emissive layer comprising the compound and a host.

16. The device of claim 15 , wherein the compound is the emissive material.

17. The device of claim 15 , wherein the host is a metal coordination complex.

18. The device of claim 17 , wherein the host is BAlq.

19. The device of claim 15 , wherein the compound is the emissive material and the host is a metal coordination complex.

20. The device of claim 19 , wherein the host is BAlq.

21. A consumer product comprising a device, the device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound having the formula:

wherein A and B are coordinated to the metal via a nitrogen atom on ring A and an sp 2 hybridized carbon atom on ring B;

wherein each of R a and R b represent no substitution, or one or more substituents;

wherein when R a and R b are one or more substituents, R a and R b are each independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups;

wherein R z represents no substitution, alkyl, heteroalkyl, aryl, or heteroaryl group;

wherein R x and R y are each independently selected from the group consisting of alkyl, heteroalkyl, aryl, and heteroaryl groups and contain a branched alkyl moiety with branching at a position further than the α position to the carbonyl group; and

wherein n is 1 or 2;

wherein A-B is selected from the group consisting of:

wherein X is N—R, O or S; and

wherein R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl groups.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2009
From: ALLEYNE, BERT; KWONG, RAYMOND; YEAGER, WALTER; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 023706/0121 →
Continuity (2)
Provisional Application 61097488 · Sep 16, 2008
Related Publication 20100090591A1 · Apr 15, 2010