OLEDs utilizing macrocyclic ligand systems

• US 7,655,323 B2
• Filed: 01/10/2005
• Issued: 02/02/2010
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation, University of Southern California
• Inventors: Mackenzie, Peter B., Thompson, Mark E., Walters, Robert
• Primary Examiner(s): Yamnitzky; Marie R.
• Application Number:
  US11/031,078
• Publication Number:
  US 20050260445A1
• Time in Patent Office: 1,849 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• 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 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/104 with other heteroatoms
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1059 containing three 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 2211/1096 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 33/14 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 85/346 comprising platinum
• CPC Class Codes: H10K 85/348 comprising osmium
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

The present invention provides organic light emitting devices (OLEDs) and materials with improved stability and efficiency when incorporated into an OLED. The materials include organometallic compounds having carbene atom/donor coordinated to a metal center. The compounds may be macrocyclic electrophosphors. The compounds may also include a macrocyclic ligand coordinated to a metal center.

Claims

1. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising one or more carbene atoms coordinated to a d⁸ metal;

wherein the compound further comprises a multidentate ligand.

2. The device of claim 1, wherein the metal is Pt(II), Pd(II), Ir(I), Au(III), or Rh(I).

3. The device of claim 2, wherein the metal is Pt(II).

4. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) and a phosphorescent emissive region disposed between the anode and the cathode, wherein the emissive region comprises an emissive material having a structure V;

5. The device of claim 4, wherein the emissive material has a structure VI:

6. The device of claim 5, wherein the emissive material has a structure VII:

7. The device of claim 5, wherein the emissive material has a structure VIII:

8. The device of claim 7, wherein the emissive material has a structure IX:

9. The device of claim 8, wherein the emissive material has a structure X:

10. The device of claim 8, wherein all of the rings A, B, C, and D are aromatic rings.

11. The device of claim 8, wherein two of the rings A, B, C, and D are imidazole rings, and each of the remaining two rings is a phenyl ring or a pyridyl ring.

12. The device of claim 11, wherein the emissive material has a structure XI:

13. The device of claim 12, wherein the emissive material has a structure XII:

14. The device of claim 11, wherein the emissive material has a structure XIII:

15. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a metal coordinated to;

i) one or more carbene donors;

ii) 0-3 neutral donors; and

iii) 0-3 monoanionic donors;

wherein the total number of donors is the maximum number of ligands that may be attached to the metal, and each donor is optionally linked to one or more adjacent donors, and two or more donors are linked to form a macrocyclic ligand.

16. The device of claim 15, wherein each interplanar angle of the macrocyclic ligand is less than about 15°

.

17. The device of claim 16, wherein each interplanar angle is less than about 10°

.

18. The device of claim 17, wherein each interplanar angle is about 0°

.

19. The device of claim 15, wherein the metal is coordinated to 4 donors, and the donors are linked to form a tetradentate ligand.

20. The device of claim 15, wherein the metal is coordinated to:

a) one or more carbene donors, wherein each carbene donor is selected from the group consisting of;

21. The device of claim 20, wherein the metal forms a carbon-metal bond with at least one carbon atom that is not a carbene donor.

22. The device of claim 21, wherein the metal forms a carbon-metal bond with a phenyl group.

23. The device of claim 22, wherein the metal is coordinated to two carbene donors and two phenyl groups.

24. The device of claim 20, wherein the metal is coordinated to two bidentate ligands.

25. The device of claim 20, wherein the metal is coordinated to one tridentate ligand and one monodentate ligand.

26. The device of claim 20, wherein the metal is coordinated to a tetradentate ligand.

27. The device of claim 20, wherein at least one ligand has a triplet energy corresponding to a wavelength of less than 450 nm.

28. The device of claim 20, wherein the compound is selected from the group consisting of: