Organic electroluminescent materials and devices

• US 9,735,373 B2
• Filed: 06/10/2013
• Issued: 08/15/2017
• Est. Priority Date: 06/10/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Dyatkin, Alexey, Xia, Chuanjun, Li, David Zenan
• Primary Examiner(s): Bohaty, Andrew K
• Application Number:
  US13/914,124
• Publication Number:
  US 20140361252A1
• Time in Patent Office: 1,527 Days
• Field of Search: None
• CPC Class Codes: C07F 5/069 without C-aluminium linkages
• CPC Class Codes: H10K 50/121 for assisting energy transfer, e.g. sensitization
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

Aluminum chelate complex compounds with two substituted 8-hydroxyquinoline ligand and one dibenzothiophene, dibenzofuran or dibenzoselenophene ligands or aza-analogs of these molecules, attached directly or through an aromatic spacer to the oxygen atom is provided to improve lifetime, operating voltage and efficiency of an OLED. Additional substitution of dibenzothiophene or dibenzofuran ring may also provide charge delocalization, HOMO modification and higher Tg.

Claims

1. A compound having a structure according to Formula I

2. The compound of claim 1, wherein M is selected from the group consisting of Al, In and Ga.

3. The compound of claim 1, wherein M is Al.

4. The compound of claim 1, wherein L is

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

6. The compound of claim 1, wherein R¹ and R² are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, iso-propyl, and combinations thereof.

7. The compound of claim 1, wherein M is aluminum;

and wherein R³, R⁴, R⁵ and R⁶ are hydrogen.

8. The compound of claim 7, wherein L is selected from the group consisting of

9. The compound of claim 7, wherein A is selected from the group consisting of

10. A formulation comprising a compound of claim 1.

11. A first device comprising a first organic light emitting device, further comprising:

an anode;

a cathode;

an organic layer, disposed between the anode and the cathode, comprising a compound having a structure according to Formula I

12. The first device of claim 11, wherein M is selected from the group consisting of Al, In and Ga.

13. The first device of claim 11, wherein M is Al.

14. The first device of claim 11, wherein L is

15. The first device of claim 11, wherein A is selected from the group consisting of:

16. The first device of claim 11, wherein M in the compound is aluminum;

and wherein R³, R⁴, R⁵ and R⁶ are hydrogen.

17. The first device of claim 11, wherein the organic layer is an emissive layer and the compound having Formula I is a host.

18. The first device of claim 11, wherein R¹ and R² are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, iso-propyl, and combinations thereof.

19. The first device of claim 17, wherein the organic layer further comprises an emissive dopant.

20. The first device of claim 19, wherein the emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

21. The first device of claim 11, wherein the organic layer is a blocking layer and the compound having the Formula I is a blocking material in the organic layer.

22. The first device of claim 11, wherein the organic layer is an electron transporting layer and the compound having the Formula I is an electron transporting material in the organic layer.

23. The first device of claim 11, wherein the first device is a consumer product.

24. The first device of claim 11, wherein the first device is an organic light-emitting device.

25. The first device of claim 11, wherein the first device is a lighting panel.