Organic electroluminescent materials and devices

• US 9,590,194 B2
• Filed: 02/14/2014
• Issued: 03/07/2017
• Est. Priority Date: 02/14/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Boudreault, Pierre-Luc T., Dyatkin, Alexey Borisovich, Xia, Chuanjun, Joseph, Scott, Li, David Zenan, Yamamoto, Hitoshi, Weaver, Michael S.
• Primary Examiner(s): Leong, Nathan T
• Application Number:
  US14/181,118
• Publication Number:
  US 20150236276A1
• Time in Patent Office: 1,117 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

The present invention relates to metal complexes having novel ligands. The compounds are useful in organic light emitting devices (OLEDs), particularly as emitting dopants. The incorporation of these novel ligands provides red phosphorescent materials with good external quantum efficiency, good color, and long lifetime.

Claims

1. A compound comprising a ligand L_A of formula I:

2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1, wherein M is Ir.

4. The compound of claim 1, wherein Y¹ is selected from the group consisting of NR′

, O, S, and CR′

R″

.

5. The compound of claim 1, wherein Y¹ is O.

6. The compound of claim 1, wherein one of X¹, X², X³, X⁴, X⁵, X⁶, X⁷, and X⁸ is nitrogen.

7. The compound of claim 1, wherein two of X¹, X², X³, X⁴, X⁵, X⁶, X⁷, and X⁸ are nitrogen.

8. The compound of claim 1, wherein one of X¹, X², X³, and X⁴ is nitrogen;

and one of X⁵, X⁶, X⁷, and X⁸ is nitrogen.

9. The compound of claim 1, wherein one of X¹, X², X³, X⁴ is nitrogen;

and X⁵, X⁶, X⁷, and X⁸ are carbon.

10. The compound of claim 1, wherein X² is nitrogen;

and X¹, X³, X⁴, X⁵, X⁶, X⁷, and X⁸ are carbon.

11. The compound of claim 1, wherein ring A is phenyl.

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

13. The compound of claim 1, wherein the compound has formula III-A:

(L_A)_nIr(L_B)_3-n 

 

(III-A);

wherein L_B is a bidentate ligand; and

n is 1, 2, or 3.

14. The compound of claim 13, wherein L_A is selected from the group consisting of L_A1 to L_A960 as shown below:

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

16. The compound of claim 15, wherein the compound has formula V:

(L_A)₁Ir(L_B)₂ 

 

(V);

and the compound is selected from the group consisting of compound 961 to compound 5760 listed in the table below, where L_A and L_R each compound are identified;

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

18. The compound of claim 17, wherein the compound has formula VI:

(L_A)₂Ir(L_B)₁ 

 

(VI);

and the compound is selected from the group consisting of compound 5761 to compound 7680 listed in the table below, where L_A for each compound are defined;

19. The compound of claim 14, wherein the compound has formula IV:

_A(L_A)₃-Ir 

 

(IV);

and the compound is selected from the group consisting of compound 1 to compound 960 listed in the table below, where L_A for each compound is identified;

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

21. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L_A of formula I;

22. A formulation comprising a compound comprising ligand L_A of formula I: