Organic electronuminescent materials and devices

• US 9,685,617 B2
• Filed: 06/27/2013
• Issued: 06/20/2017
• Est. Priority Date: 11/09/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Zeng, Lichang, Weaver, Michael S., Beers, Scott, Adamovich, Vadim
• Primary Examiner(s): Chriss, Jennifer
• Assistant Examiner(s): KERSHNER, DYLAN CLAY
• Application Number:
  US13/928,456
• Publication Number:
  US 20140131676A1
• Time in Patent Office: 1,454 Days
• Field of Search: 548103, 548108, 548402, 546 4, 546 10, 428690, 428917, 257 40, 257E51041, 257E51043, 257E51044, 313504, 313506, 25230116
• CPC Class Codes: C07F 15/0033 Iridium 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 50/00 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 85/342 comprising iridium
• 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

Novel iridium complexes containing phenylpyridine and pyridyl aza-benzo fused ligands are described. These complexes are useful as light emitters when incorporated into OLEDs.

Claims

1. A compound having a structure Ir(L_A)_n(L_B)_3-n according to Formula II

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

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

4. The compound of claim 1, wherein R is alkyl.

5. The compound of claim 1, wherein R is cycloalkyl.

6. The compound of claim 1, 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.

7. The compound of claim 1, wherein R¹, R², R³, and R⁴ are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

8. The compound of claim 1, wherein R² is alkyl, or partially or fully deuterated alkyl.

9. The compound of claim 1, wherein R³ is alkyl, or partially or fully deuterated alkyl.

10. The compound of claim 1, wherein R¹, R², R³, and R⁴ are H.

11. The compound of claim 10, 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.

12. The compound of claim 10, wherein R is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, and partially or fully deuterated variants thereof.

13. The compound of claim 1, wherein R¹, R², R³, and R⁴ are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

14. The compound of claim 13, 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.

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

16. The compound of claim 15, wherein R³ and R⁴ are independently selected from the group consisting of hydrogen, deuterium, alkyl, and combinations thereof.

17. The compound of claim 15, wherein R³ and R⁴ are H.

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

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

20. 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 Ir(L_A)_n(L_B)_3-n, having the structure;

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

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

23. The first device of claim 20, wherein the first device comprises a lighting panel.

24. The first device of claim 20, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

25. The first device of claim 20, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

26. The first device of claim 20, wherein the organic layer further comprises a host.

27. The first device of claim 26, 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, 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.

28. The first device of claim 26, wherein the host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

29. The first device of claim 26, wherein the host is selected from the group consisting of:

30. The first device of claim 26, wherein the host comprises a metal complex.

31. A formulation comprising a compound having the formula Ir(L_A)_n(L_B)_3-n, having the structure: