Phosphorescent heteroleptic phenylbenzimidazole dopants

• US 9,212,197 B2
• Filed: 05/19/2011
• Issued: 12/15/2015
• Est. Priority Date: 05/19/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kottas, Gregg, Xia, Chuanjun, Elshenawy, Zeinab, Ansari, Nasrin
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US13/111,490
• Publication Number:
  US 20120292600A1
• Time in Patent Office: 1,671 Days
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium 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 85/342 comprising iridium

Abstract

Novel phosphorescent heteroleptic iridium complexes with benzimidazole and phenylpyridine ligands are provided. These iridium complexes can improve OLED properties, and are useful in white light applications.

Claims

1. A compound comprising a heteroleptic iridium complex having the formula:

2. The compound of claim 1, wherein n=2.

3. The compound of claim 1, wherein n=1.

4. The compound of claim 1, wherein R₂ is aryl or substituted aryl.

5. The compound of claim 4, wherein R₂ is a 2,6-disubstituted aryl.

6. The compound of claim 5, wherein R₂ is

7. The compound of claim 1, wherein R₂ is alkyl.

8. The compound of claim 1, wherein R₃, R₄, R₅ and R₆ are each independently selected from the group consisting of hydrogen and alkyl, and wherein at least one of R₃, R₄, R₅ and R₆ is alkyl.

9. The compound of claim 1, wherein R₅ is aryl.

10. The compound of claim 1, wherein R₆ is fused to form a naphthyl or aza-naphthyl ring system.

11. The compound of claim 1, wherein R₁, R₃, and R₅ are hydrogen.

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

13. 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;

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

15. The first device of claim 13, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

16. The first device of claim 13, wherein the organic layer further comprises a host.

17. The first device of claim 16, 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≡

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.

18. The first device of claim 17, wherein the host has the formula:

19. The first device of claim 16, wherein the host is a metal complex.

20. The first device of claim 13 wherein the first device is a consumer product.

21. The first device of claim 13, wherein the first device is an organic light-emitting device.

22. The first device of claim 13, wherein the first device further comprises a second emissive dopant having a peak wavelength of between 400 to 500 nanometers.

23. The first device of claim 22, wherein the second emissive dopant is a fluorescent emitter.

24. The first device of claim 22, wherein the second emissive dopant is a phosphorescent emitter.

25. The first device of claim 13, wherein the first device comprises a lighting panel.

26. The first device of claim 13, wherein the first device further comprises a first organic light-emitting device comprising a compound of Formula I and a second light emitting device separate from the first organic light-emitting device comprising an emissive dopant having a peak wavelength of between 400 to 500 nanometers.

27. The first device of claim 13, wherein the first device comprises an organic-light emitting device having a first emissive layer and a second emissive layer;

wherein the first emissive layer comprises a compound of Formula I; and

wherein the second emissive layer comprises an emissive dopant having a peak wavelength of between 400 to 500 nanometers.