2-azatriphenylene materials for organic light emitting diodes

• US 9,005,771 B2
• Filed: 05/12/2010
• Issued: 04/14/2015
• Est. Priority Date: 05/12/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Kwong, Raymond C.
• Primary Examiner(s): Yang, J. L.
• Application Number:
  US12/778,362
• Publication Number:
  US 20100289406A1
• Time in Patent Office: 1,798 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 421/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• 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 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/342 comprising iridium
• 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

Compounds containing 2-azatriphenylene are provided. In particular, compounds containing a 2-azatriphenylene core having an additional aromatic group are provided. The compounds provided may be emissive or non-emissive materials. The compounds may be used in organic light emitting devices, particularly as host materials, hole blocking layer materials, or emitting dopants. Devices comprising 2-azatriphenylene containing compounds may demonstrate improved stability and efficiency.

Claims

1. A compound including the structure;

2. The compound of claim 1, herein the compound has the formula:

3. The compound of claim 1, wherein R₃ is a substitution ortho to the nitrogen.

4. The compound of claim 1, wherein R₁ comprises a heteroaryl.

5. The compound of claim 1, wherein R₂ comprises a heteroaryl.

6. The compound of claim 1, wherein R₃ comprises a heteroaryl.

7. The compound of claim 1, wherein each of R₁, R₂, and R₃ comprises a heteroaryl.

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

8. A compound comprising a ligand L having a formula selected from the group consisting of:

9. The compound of claim 8, wherein the metal is Ir.

10. The compound of claim 9, wherein the ligand L is included in a homoleptic compound.

11. The compound of claim 9, wherein the ligand L is included in a heteroleptic compound.

12. The compound of claim 11, wherein the compound has the formula (L)_n(L′

)_3-nIr;

wherein n is 1 or 2;

wherein L′

is selected from the group consisting of;

13. The compound of claim 8, wherein the ligand L is selected from the group consisting of:

14. The compound of claim 8, wherein the ligand L is selected from the group consisting of:

15. The compound of claim 8, wherein the compound is selected from the group consisting of:

16. The compound of claim 8, wherein the compound is selected from the group consisting of:

17. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound that includes the structure;

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

19. The first device of claim 17, wherein the first device is a consumer product.

20. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

a first organic layer, disposed between the anode and the cathode, the first organic layer further comprising a compound comprising

a ligand L having a formula selected from the group consisting of;