Organic electroluminescent materials and devices

• US 9,461,254 B2
• Filed: 01/02/2013
• Issued: 10/04/2016
• Est. Priority Date: 01/03/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Kottas, Gregg, Brooks, Jason, Yeager, Walter, Ansari, Nasrin, Barron, Edward, Xia, Chuanjun
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US13/732,502
• Publication Number:
  US 20130168656A1
• Time in Patent Office: 1,371 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• 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 50/81 Anodes
• CPC Class Codes: H10K 85/00 Organic materials used in the body or electrodes of devices covered by this subclass
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein the A-L₁-B structure is A-L₁-B4 and at least one fused ring is formed by joining R or R′

of L₁ to an adjacent substituent selected from the group consisting of R₁ and R₂,

R or R′

of L₂ to an adjacent substituent selected from the group consisting of R₂ and R₃, or

R or R′

of L₃ to an adjacent substituent selected from the group consisting of R₃ and R₄.

3. The compound of claim 1, wherein at least one of L₁, L₂ and L₃ is NR.

4. The compound of claim 1, wherein L₁ and L₃ are NR.

5. The compound of claim 1, wherein the A-L₁-B structure is A-L₁-B4 and Z₄ are nitrogen atoms coordinated to metal atom M.

6. The compound of claim 1, wherein the A-L₁-B structure is A-L₁-B4 and Z₄ are carbon atoms coordinated to metal atom M.

7. The compound of claim 1, wherein M is Pt.

10. The compound of claim 1, wherein the compound has the formula:

11. The compound of claim 10, wherein the compound has the formula:

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

13. The compound of claim 1, wherein L₂ is independently selected from the group consisting of O, S, and NR.

14. The compound of claim 13, wherein L₂ is NR, and R is phenyl or substituted phenyl.

15. The compound of claim 13, wherein L₂ is O.

16. The compound of claim 1, wherein Z₁ and Z₄ are nitrogen atoms.

29. The compound of claim 1, wherein A-L₁-B is

8. A compound having the formula:

9. The compound of claim 8, wherein the compound has the formula:

17. A compound selected from the group consisting of compounds 1-24, 34-115, 121-129 and 131, wherein compounds 1-24, 34-115, 121-129 and 131 have the following structures:

18. A first device comprising a 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 the formula;

19. The first device of claim 18, wherein the first device is a consumer product.

20. The first device of claim 18, wherein the first device is an organic light-emitting device.

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

22. The first device of claim 18, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

23. The first device of claim 18, wherein the organic layer is an emissive layer and the compound is an non-emissive dopant.

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

25. The first device of claim 24, 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, OAr_i, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_nH_2n+1, C≡

CC_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.

26. The first device of claim 25, wherein the host comprises one or more compounds having the formula:

27. The first device of claim 25, wherein the host comprises a metal complex.

28. The first device of claim 24, wherein the host is selected from the group consisting of