Near infrared emitting organic compounds and organic devices using the same

• US 7,989,090 B2
• Filed: 08/25/2009
• Issued: 08/02/2011
• Est. Priority Date: 09/11/2006
• Status: Active Grant

• Current Assignee: The Trustees of Princeton University (Princeton University), Board of Regents of the University of Michigan (University of Michigan), University of Southern California
• Original Assignee: The Trustees of Princeton University (Princeton University), Board of Regents of the University of Michigan (University of Michigan), University of Southern California
• Inventors: Borek, Carsten, Hanson, Kenneth, Sun, Yiru, Forrest, Stephen, Thompson, Mark E., Djurovich, Peter, Tamayo, Arnold
• Primary Examiner(s): Aulakh; Charanjit
• Application Number:
  US12/546,829
• Publication Number:
  US 20100013386A1
• Time in Patent Office: 707 Days
• Field of Search: 428/690, 313/504
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium 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 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• 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 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Certain iridium compounds which may comprise an iridium(III)-ligand complex having the general formula: (C^N)₂—Ir—(N^N). (C^N) and (N^N) may each represent a ligand coordinated to an iridium atom. The iridium compounds may have a primary phosphorescent photoluminescence peak wavelength in the near-infrared (IR) range. Also, organic devices that use certain iridium compounds. The organic device may comprise an organic layer and the organic layer may comprise any of the iridium compounds disclosed herein. Also, organic devices that use certain metalloporphyrin compounds. The metalloporphyrin compounds may comprise a core porphyrin structure with four pyrrole rings. The metalloporphyrin compounds may have a primary phosphorescent photoluminescence peak wavelength in the near-IR range.

Claims

1. An organic light-emitting device comprising:

an anode;

a cathode; and

an organic layer between the anode and the cathode, the organic layer comprising a host material and a metalloporphyrin compound, wherein the metalloporphyrin compound comprises a plurality of pyrrole rings and has a formula;

2. The organic device of claim 1, wherein the metalloporphyrin compound has a primary phosphorescent photoluminescence emission peak wavelength greater than about 680 nm.

3. The organic device of claim 1, wherein the metalloporphyrin compound has a primary phosphorescent photoluminescence emission peak with a bandwidth less than about 60 nm.

4. The organic device of claim 1, wherein each of R₁ to R₄ is an aryl moiety or heteroaryl moiety.

5. The organic device of claim 4, wherein each of R₁ to R₄ is independently selected from the group consisting of:

6. The organic device of claim 4, wherein each of R₁ to R₄ is fused to the adjoining pyrrole ring.

7. The organic device of claim 1, wherein M is platinum.

8. The organic device of claim 1, wherein each of R₁′

to R₄′

is a phenyl.

9. The organic device of claim 1, wherein the metalloporphyrin compound has the formula:

10. The organic device of claim 1, wherein the organic layer is an emissive layer.

11. The organic device of claim 9, wherein the organic layer is an emissive layer.

12. The organic device of claim 4, wherein the organic layer is an emissive layer.

13. The organic device of claim 5, wherein the organic layer is an emissive layer.

14. The organic device of claim 6, wherein the organic layer is an emissive layer.

15. The organic device of claim 1, wherein each of R₁ to R₄ is an aryl or heteroaryl moiety that is fused to the adjoining pyrrole ring, wherein each of R₁′

to R₄′

is a phenyl, wherein M is platinum, and wherein the organic layer is an emissive layer.

16. The organic device of claim 5, wherein M is platinum.

17. The organic device of claim 4, wherein each of R₁ to R₄ is fused to the adjoining pyrrole ring, wherein each of R₁′

to R₄′

is a phenyl, and wherein M is platinum.