Organic electroluminescent materials and devices

• US 9,748,503 B2
• Filed: 09/13/2013
• Issued: 08/29/2017
• Est. Priority Date: 09/13/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi
• Primary Examiner(s): Vetere, Robert
• Application Number:
  US14/026,392
• Publication Number:
  US 20150076454A1
• Time in Patent Office: 1,446 Days
• CPC Class Codes: C07F 15/002 Osmium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/348 comprising osmium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Bis(tridentate) osmium(II) complexes containing phosphite groups useful as phosphorescent emitters are disclosed. The disclosed osmium(II) complexes have higher oxidation potential then previously known osmium(II) complexes. An organic light emitting device having an organic layer that includes the disclosed osmium(II) complex is also disclosed.

Claims

1. A compound having a structure selected from the group consisting of:

2. The compound of claim 1, wherein X is a neutral nitrogen atom of an imidazole ring, C is an anionic donor carbon, and P is a neutral donor phosphorus.

3. The compound of claim 1, wherein the compound is neutral.

4. The compound of claim 1, wherein X is a carbon, and Os—

X bond is a metal-carbene bond.

5. The compound of claim 1, wherein the compound is homoleptic.

6. The compound of claim 1, wherein the compound is heteroleptic.

7. The compound of claim 1, wherein the compound has the structure of

8. The compound of claim 1, wherein the compound has the structure of

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

22. The compound of claim 1, wherein the P of

23. The compound of claim 1, wherein the P of

10. 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 structure selected from the group consisting of;

11. The first device of claim 10, wherein X is a neutral nitrogen atom of an imidazole ring, C is an anionic donor carbon, and P is a neutral donor phosphorus.

12. The first device of claim 10, wherein the compound has the structure of

13. The first device of claim 10, wherein the first device is selected from the group consisting of a consumer product, an organic light emitting device, and a light panel.

14. The first device of claim 10, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

15. The first device of claim 10, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

16. The first device of claim 10, wherein the organic layer further comprises a host material.

17. The first device of claim 16, 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≡

C—

C_nH_2n+1, Ar₁, Ar₁-Ar₂, and C_nH_2n-Ar₁—

;

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.

18. The first device of claim 16, wherein the host material comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

19. The first device of claim 16, wherein the host material is selected from the group consisting of:

20. The first device of claim 16, wherein the host material comprises a metal complex.

21. A formulation comprising a compound having a structure selected from the group consisting of: