Organic electroluminescent materials and devices

• US 9,577,201 B2
• Filed: 08/14/2015
• Issued: 02/21/2017
• Est. Priority Date: 03/08/2007
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Ma, Bin, Xia, Chuanjun, Alleyne, Bert, Brooks, Jason
• Primary Examiner(s): Bohaty, Andrew K
• Application Number:
  US14/826,762
• Publication Number:
  US 20150357588A1
• Time in Patent Office: 557 Days
• Field of Search: 428/690, 428/917, 428/336, 428/411.4, 313502-509, 257/40, 257 88-104, 257E51001-E51052, 25230116-30135, 546/4
• 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 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• 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 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/381 Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc

Abstract

A compound including a ligand having the formula:

is disclosed. In these formulas, each R₁, R₂, and R₃ is independently selected from hydrogen, alkyl, and aryl; at least one of R₁ and R₂ is a branched alkyl containing at least 4 carbon atoms, where the branching occurs at a position further than the benzylic position; where R₁ and R₃ are mono-, di-, tri-, tetra-, or no substitutions; and R₂ is mono-, di-, or no substitutions. Heteroleptic iridium complexes including such compounds, and devices including such compounds are also disclosed.

Claims

1. An iridium compound having the formula:

2. The compound of claim 1, wherein at least one of R₁ and R₂ is an isobutyl group.

3. The compound of claim 1, wherein X—

Y is acac.

4. The compound of claim 1, having a structure of the formula:

5. The compound of claim 1, having a structure of the formula:

6. A compound including a ligand having the formula:

7. The compound of claim 6, wherein the ligand is coordinated to a metal having an atomic number greater than 40.

8. The compound of claim 6, wherein the metal is Ir.

9. The compound of claim 6, including a ligand having a structure of the formula:

10. The compound of claim 6, including a ligand having a structure of the formula:

11. An organic light emitting device comprising:

an anode;

a cathode; and

an emissive organic layer, disposed between the anode and the cathode, wherein the organic layer comprises an iridium compound having the formula;

12. The device of claim 11, wherein the organic emissive layer further comprises BAlq or

13. The device of claim 12, wherein the compound is:

14. The device of claim 12, wherein the compound is

15. The device of claim 11, wherein at least one of R₁ and R₂ is an isobutyl group.

16. The device of claim 11, wherein X—

Y is acac.

17. The device of claim 11, wherein the compound has a structure of the formula:

18. The device of claim 11, wherein the compound has a structure of the formula: