IP Library Granted Patent US 9,359,549
Granted Patent B2
US 9,359,549 · App. 13/263,294 · Granted Jun 7, 2016

Organic electroluminescent materials and devices

Inventors: Dinesh Rayabarapu (Waldwick, NJ); Chuanjun Xia (Lawrenceville, NJ); Raymond C. Kwong (Fo Tan, HK); Bin Ma (West Windsor, NJ); Walter Yeager (Yardley, PA); Bert Alleyne (Ewing, NJ)
Assignee: Universal Display Corporation
C09K11/06C07F15/0033H01L51/0085H05B33/14C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 9,359,549
App. No.
13/263,294
Granted
Jun 7, 2016
Kind
B2
Abstract

Compounds comprising a metal complex having novel ligands are provided. In particular, the compound is an iridium complex comprising novel aza DBX ligands. The compounds may be used in organic light emitting devices, particularly as emitting dopants, providing improved efficiency, low operating voltage, and long lifetime.

Claims (43)

1. A compound having the structure of formula (L) n (L′) 3-n Ir, wherein n is 1 or 2, ligand L has a structure

and ligand L′ has a structure selected from the group consisting of:

wherein each A is independently a 5-membered or 6-membered aromatic or heteroaromatic ring;

wherein R A is a substituent having the structure

wherein R A is fused to the pyridine ring of FORMULA I and the dashed line in R A indicates where R A is fused to the pyridine ring of FORMULA I;

wherein each X is independently selected from the group consisting of CRR″, C═O, BR, O, S, and Se;

wherein each R and R′ is independently selected from hydrogen and alkyl;

wherein each R 1 , R 3 , R 4 , and R 5 may independently represent mono, di, tri, or tetra substitutions;

wherein R 2 may represent mono or di substitutions;

wherein each of R 1 , R 7 , R 3 , R 4 , and R 5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl; and

wherein the compound is heteroleptic.

2. The compound of claim 1 , wherein ligand L′ is

3. The compound of claim 2 , wherein the compound is selected from the group consisting of:

4. The compound of claim 1 , wherein X is O.

5. The compound of claim 1 , wherein X is S.

6. The compound of claim 1 , wherein X is CRR′.

7. The compound of claim 1 , wherein X is CO.

8. The compound of claim 1 , wherein the compound is selected from the group consisting of:

9. The compound of claim 8 , wherein the compound is selected from the group consisting of Compound 1-Compound 12.

10. The compound of claim 8 , wherein the compound is selected from the group consisting of Compound 13-Compound 24.

11. The compound of claim 8 , wherein the compound is selected from the group consisting of Compound 37-Compound 48.

12. The compound of claim 8 , wherein the compound is selected from the group consisting of Compound 49-Compound 60.

13. 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 structure of formula (L) n (L′) 3-n Ir, wherein n is 1 or 2, ligand L has a structure

 and ligand L′ has a structure selected from the group consisting of:

wherein each A is independently a 5-membered or 6-membered aromatic or heteroaromatic ring;

wherein R A is a substituent having the structure

wherein R A is fused to the pyridine ring of FORMULA I and the dashed line in R A indicates where R A is fused to the pyridine ring of FORMULA I;

wherein each X is independently selected from the group consisting of CRR′, C═O; BR, O; S, and Se;

wherein each R and R′ is independently selected from hydrogen and alkyl;

wherein each R 1 , R 3 , R 4 , and R 5 may independently represent mono, di, tri, or tetra substitutions;

wherein R 2 may represent mono or di substitutions;

wherein each of R 1 , R 2 , R 3 , R 4 , and R 5 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl; and

wherein the compound is heteroleptic.

14. The device of claim 13 , wherein the organic layer is an emissive layer and the compound is an emitting dopant.

15. The device of claim 13 , wherein the organic layer further comprises a host.

16. The device of claim 15 , wherein the host has the formula:

wherein R′ 2 and R′ 4 may represent mono, di, or tri substitutions;

wherein R′ 1 , R′ 3 , R′ 5 , and R′ 6 may represent mono, di, tri, or tetra substitutions; and

wherein each of R′ 1 , R′ 2 , R′ 3 , R′ 4 , R′ 5 , and R′ 6 are each independently selected from the group consisting of hydrogen, alkyl and aryl.

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2011
From: RAYABARAPU, DINESH; KWONG, RAYMOND; MA, BIN; YEAGER, WALTER; XIA, CHUANJUN; ALLEYNE, BERT
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 027123/0103 →
Continuity (2)
Provisional Application 61167014 · Apr 6, 2009
Related Publication 20120061654A1 · Mar 15, 2012