Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs

• US 9,059,412 B2
• Filed: 03/06/2013
• Issued: 06/16/2015
• Est. Priority Date: 07/19/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Zeng, Lichang, Ma, Bin, Elshenawy, Zeinab, Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Branch, Catherine S
• Application Number:
  US13/786,513
• Publication Number:
  US 20140027733A1
• Time in Patent Office: 832 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: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Compounds having a metal M complexed to a ligand L containing a substituted imidazole carbene group, which is represented Formula (I), below:

wherein ring B is a 5-member aromatic heterocyclic ring containing at least one heteroatom selected from the group consisting of N, O, and S; wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring; wherein R_A represents mono, di, tri, tetra substitutions or no substitution; wherein R₁ represents mono, di, or tri substitution or no substitution; wherein each R_A, R₁ and R₂ is independently selected from various possible substituents; wherein Z₁ is nitrogen or carbon; and wherein the ligand is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand. Devices, such as organic light emitting devices (OLEDs) that comprise such compounds are also provided.

Claims

1. A compound comprising a ligand L₃ of Formula (I):

2. The compound of claim 1, wherein M₁ is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1, wherein M₁ is Ir or Pt.

4. The compound of claim 1, wherein ligand L₃ is selected from the group consisting of:

5. The compound of claim 4, wherein the ligand L₃ is selected from the group consisting of:

6. The compound of claim 5, wherein the ligand L₃ is selected from the group consisting of:

7. The compound of claim 1, where the compound is a compound of Formula (II):

8. The compound of claim 1, wherein the compound is a compound of Formula (III):

9. The compound of claim 8, wherein the compound is a compound of Formula (IV):

10. The compound of claim 9, wherein the compound is a compound of Formula (V):

11. The compound of claim 1, wherein the compound is a compound of Formula (VI):

12. The compound of claim 11, wherein the compound is a compound of Formula (VII):

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

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

15. A first device comprising a first organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L₃ of Formula (I);

16. The first device of claim 15, wherein the first device is a consumer product.

17. The first device of claim 15, wherein the first device is an organic light-emitting device.

18. The first device of claim 15, wherein the first device comprises a lighting panel.

19. The first device of claim 15, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

20. The first device of claim 15, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

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

22. The first device of claim 21, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C_nH_2n+1, OC_nH_2n+1, OAr₁, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_nH_2n+1, C≡

C—

C_nH_2n+1, Ar₁, Ar₁-Ar₂, C_nH_2n—

Ar₁, or no substitution;

wherein n is from 1 to 10; and

wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

23. The first device of claim 21, wherein the host is selected from the group consisting of:

24. The first device of claim 21, wherein the host comprises a metal complex.

25. The first device of claim 21, wherein the host comprises at least one of the chemical groups selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.