Iridium complexes with aza-benzo fused ligands

• US 8,946,697 B1
• Filed: 09/16/2013
• Issued: 02/03/2015
• Est. Priority Date: 11/09/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Barron, Edward, DeAngelis, Alan, Yeager, Walter, Xia, Chuanjun, Cheon, Kwang-Ohk, Beers, Scott, Weaver, Michael S.
• Primary Examiner(s): Pizarro, Marcos D.
• Assistant Examiner(s): Garces, Nelson
• Application Number:
  US14/028,499
• Time in Patent Office: 505 Days
• Field of Search: 257/40, 257/E51.001, 257/E51.041
• US Class Current: 257/40
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 50/00 Organic light-emitting devices integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel iridium complexes containing phenylpyridine and pyridyl aza-benzo fused ligands are described. Iridium complexes containing aza-benzo fused ligands in which an aryl group is conjugated to the aza ring of the specific aza-dibenzofuran ring system results in the formation of yellow phosphorescent compounds with superior device stability and efficiency. These complexes are useful as light emitters when incorporated into OLEDs.

Claims

1. A compound having the formula Ir(L_A)_n(L_B)₃₋

n, having the structure;

2. The compound of claim 1, wherein R² is phenyl or substituted phenyl.

3. The compound of claim 1, wherein R² is pyridine or substituted pyridine.

4. The compound of claim 1, wherein R² represents mono-substitution.

5. The compound of claim 1, wherein n is 1.

6. The compound of claim 1, wherein the compound has the structure according to Formula II below:

7. The compound of claim 6, wherein n is 1.

8. The compound of claim 1, wherein only one of A¹ to A⁸ is nitrogen.

9. The compound of claim 8, wherein only one of A⁵ to A⁸ is nitrogen.

10. The compound of claim 1, wherein X is O.

11. The compound of claim 1, wherein R¹, R³, and R⁴ are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

12. The compound of claim 1, wherein R³ is alkyl.

13. The compound of claim 12, wherein the alkyl is deuterated or partially deuterated.

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

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

16. The compound of claim 15, wherein the compound is selected from the group consisting of:

17. The compound of claim 16, wherein the compound is selected from the group consisting of:

Compound III-1, Compound III-2, Compound III-3, Compound III-5, Compound III-8, Compound III-11, Compound III-14, Compound III-25, Compound III-26, Compound III-27, Compound III-29, Compound III-32, Compound III-34, Compound III-35, Compound III-37, Compound III-38, Compound III-44, Compound III-46, Compound III-47, Compound III-49, Compound III-50, Compound III-53, Compound III-56, Compound III-59, Compound III-62, Compound III-65, Compound III-68, Compound III-71, Compound III-73, Compound III-74, Compound III-82, Compound III-98, Compound III-97, Compound III-110, Compound III-122, Compound III-133, Compound III-134, Compound III-137, Compound III-143, Compound III-145, Compound III-146, Compound III-151, Compound III-152, Compound III-163, Compound III-164, Compound III-196, Compound III-220, Compound III-1559, Compound III-1604, Compound III-1738, Compound III-1750, Compound III-4285, Compound III-4300, Compound III-4470, Compound III-4622, Compound III-4640, Compound III-4690, Compound III-4736, Compound III-4907, Compound III-5076, Compound III-5979, Compound III-6139, Compound III-4810, Compound III-4980, Compound III-5150, Compound III-5320, Compound III-5475, Compound III-5490, and Compound III-5660.

18. The compound of claim 1, wherein A¹-A⁴ and A⁶-A⁸ are C;

A⁵ is N; and

said compound having a structure according to Formula III

19. The compound of claim 18, wherein R² is phenyl or substituted phenyl.

20. The compound of claim 18, wherein R² is pyridine or substituted pyridine.

21. The compound of claim 18, wherein R² represents mono-substitution.

22. The compound of claim 18, wherein n is 1.

23. The compound of claim 18, wherein X is O.

24. The compound of claim 18, wherein R is alkyl.

25. The compound of claim 18, wherein R is cycloalkyl.

26. The compound of claim 18, wherein R is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated variants thereof, and combinations thereof.

27. The compound of claim 18, wherein R¹, R³, and R⁴ are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

28. The compound of claim 18, wherein R³ is alkyl, or partially or fully deuterated alkyl.

29. The compound of claim 18, wherein L_A is selected from the group consisting of:

30. The compound of claim 18, wherein L_B is selected from the group consisting of:

31. 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 having the formula Ir(L_A)_n(L_B)<sub>3−

n</sub>, having the structure;

32. The first device of claim 31, wherein R² is phenyl or substituted phenyl.

33. The first device of claim 31, wherein R² is pyridine or substituted pyridine.

34. The first device of claim 31, wherein R² represents mono-substitution.

35. The first device of claim 31, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

36. The first device of claim 31, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

37. The first device of claim 31, wherein the organic layer further comprises a host.

38. The first device of claim 37, 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≡

CHC_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.

39. The first device of claim 37, wherein the host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

40. The first device of claim 37, wherein the host is selected from the group consisting of:

41. The first device of claim 37, wherein the host comprises a metal complex.

42. The first device of claim 31, wherein the compound having the formula Ir(L_A)_n(L_B)₃₋

n, has the structure according to Formula II

43. A formulation comprising a compound a compound having the formula Ir(L_A)_n(L_B)₃₋

n, having the structure;