Organic electroluminescent materials and devices

• US 10,644,251 B2
• Filed: 12/04/2013
• Issued: 05/05/2020
• Est. Priority Date: 12/04/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): Murata, Austin
• Application Number:
  US14/096,458
• Publication Number:
  US 20150155501A1
• Time in Patent Office: 2,344 Days
• CPC Class Codes: C07F 13/00 Compounds containing elements of Groups 7 or 17 of the Periodic Table
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence

Abstract

A novel compound having a formula Re(L_A)(L_B), wherein Re is a Rhenium(I) metal, wherein L_A is a monoanionic tridentate ligand, wherein L_B is a neutral tridentate ligand, and wherein L_A and L_B are optionally linked together to form a hexadentate ligand is disclosed.

Claims

1. A compound having a formula Re(L_A)(L_B),

wherein Re is a Rhenium(I) metal;

wherein L_A is a monoanionic tridentate ligand having a formula selected from the group consisting of

2. The compound of claim 1, wherein the neutral carbon is imidazole or benzimidazole carbene;

wherein the neutral phosphorus is a phosphorus atom of a trisubstituted phosphine; and

wherein the neutral nitrogen is an sp² nitrogen atom of N-heterocyclic ring selected from the group consisting of pyridine, pyrimidine, imidazole, benzoimidazole, pyrazole, oxazole, and triazole.

3. The compound of claim 1, wherein the monoanionic coordinating carbon is an sp² carbon atom selected from the group consisting of benzene, pyridine, furan, thiophene, and pyrrole.

4. The compound of claim 1, wherein L_A has a formula selected from the group consisting of:

5. The compound of claim 1, wherein L_A has a formula selected from the group consisting of:

6. The compound of claim 1, wherein L_B has a formula selected from the group consisting of:

7. The compound of claim 1, wherein L_B has a formula selected from the group consisting of:

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

9. The compound of claim 1, wherein each of X³ and X⁴ is an imidazole derived carbene neutral carbon.

10. The compound of claim 1, wherein each of X³ and X⁵ is an imidazole derived carbene neutral carbon.

11. The compound of claim 10, wherein X⁴ is a neutral nitrogen is an sp² nitrogen atom of an N-heterocyclic ring selected from the group consisting of pyridine, pyrimidine, imidazole, benzoimidazole, pyrazole, oxazole, and triazole;

and

wherein each of X¹ and X² is an imidazole derived carbene neutral carbon.

12. 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 having a formula Re(L_A)(L_B);

wherein Re is a Rhenium(I) metal;

wherein L_A is a monoanionic tridentate ligand having a formula selected from the group

13. The first device of claim 12, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

14. The first device of claim 12, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

15. The first device of claim 12, wherein the organic layer is a charge transporting layer and the compound is a charge transporting material in the organic layer.

16. The first device of claim 12, wherein the organic layer is a charge injecting layer and the compound is a charge injecting material in the organic layer.

17. The first device of claim 12, wherein the organic layer is a blocking layer and the compound is a blocking material in the organic layer.

18. The first device of claim 12, wherein the organic layer further comprises a host material.

19. The first device of claim 18, wherein the host material comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host material 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≡

CC_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.

20. A formulation comprising a compound having the formula Re(L_A)(L_B):

wherein Re is a Rhenium(I) metal;

wherein L_A is a monoanionic tridentate ligand having a formula selected from the group consisting of