Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9359549-B2
Application number	US-201013263294-A
Country	US
Kind code	B2
Filing date	Apr 6, 2010
Priority date	Apr 6, 2009
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

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.

First claim

The invention claimed is:

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:

Assignees

• Rayabarapu Dinesh
• Xia Chuanjun
• Kwong Raymond C
• Ma Bin
• Yeager Walter
• Alleyne Bert
• Universal Display Corp

Inventors

• Rayabarapu Dinesh
• Xia Chuanjun
• Kwong Raymond C
• Ma Bin
• Yeager Walter
• Alleyne Bert

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1033

  with oxygen · CPC title