Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir

• US 8,372,528 B2
• Filed: 10/06/2011
• Issued: 02/12/2013
• Est. Priority Date: 03/24/2003
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Tamayo, Arnold, Djurovich, Peter
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US13/267,382
• Publication Number:
  US 20120025698A1
• Time in Patent Office: 495 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0046 Ruthenium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 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 2101/00 Properties of the organic materials covered by group H10K85/00
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

The invention provides emissive materials and organic light emitting devices using the emissive materials in an emissive layer disposed between and electrically connected to an anode and a cathode. The emissive materials include compounds with the following structure:

wherein at least one of R₈ to R₁₄ is phenyl or substituted phenyl, and/or at least two of R₈ to R₁₄ that are adjacent are part of a fluorenyl group. The emissive materials have enhanced electroluminescent efficiency and improved lifetime when incorporated into light emitting devices.

Claims

1. A compound, having the structure:

2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

3. The compound of claim 2, wherein M is Ir.

4. The compound of claim 3, wherein R₈, and R₁₁-R₁₄ are H.

5. The compound of claim 1, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

6. The compound of claim 1, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

7. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between the anode and the cathode, the emissive layer comprising a compound of claim 1.

8. The device of claim 7, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

9. The device of claim 8, wherein M is Ir.

10. The device of claim 9, wherein R₈, and R₁₁-R₁₄ are H.

11. The device of claim 7, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

12. The device of claim 7, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

13. The device of claim 7, wherein the “

n”

-bracketed ligand functions as a phosphorescent emissive ligand in the compound.

14. The device of claim 7, wherein Z is selected from —

CH₂—

or substituted carbon.

15. The device of claim 14, wherein M is iridium.

16. The device of claim 15, wherein R₈ and R₁₁-R₁₄ are H.

17. The device of claim 7, wherein the “

n”

-bracketed ligand in the compound is 1-(2-(9,9-dimethyl)fluorenyl)pyrazole.

18. The device of claim 7, wherein the compound is a blue-emitting phosphorescent emissive material.