OLEDs utilizing macrocyclic ligand systems

• US 20050260444A1
• Filed: 01/10/2005
• Published: 11/24/2005
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: The Trustees of Princeton University (Princeton University), University of Southern California
• Original Assignee: The Trustees of Princeton University (Princeton University)
• Inventors: Forrest, Stephen R., Thompson, Mark E.
• Granted Patent: US 7,655,322 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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 2211/1044 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 2211/1092 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 33/14 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 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/342 comprising iridium
• 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 relates to efficient organic light emitting devices (OLEDs), and more specifically to organic materials used in such devices. More specifically, the present invention relates to materials with improved stability and efficiency when incorporated into an OLED.

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 an organometallic compound further comprising a macrocyclic ligand coordinated to a metal center, wherein each interplanar angle of the macrocyclic ligand is less than about 15°

.

2. The device of claim 1, wherein each interplanar angle is less than about 10°

.

3. The device of claim 2, wherein each interplanar angle is about 0°

.

4. The device of claim 1, wherein the macrocyclic ligand is a tetradentate ligand.

5. The device of claim 4, wherein the tetradentate ligand comprises two 5-membered rings and two 6-membered rings, each ring coordinated to the metal center.

6. The device of claim 1, wherein the compound has a structure (I):

7. The device of claim 6, wherein M is Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, or Ag.

8. The device of claim 6, wherein n is 2 and m is 0.

9. The device of claim 8, wherein the compound has a structure III:

10. The device of claim 8, wherein the compound has a structure IV:

11. The device of claim 1, wherein the compound further comprises a carbene donor.

12. The device of claim 11, wherein the compound is selected from the group consisting of:

13. A organometallic tetradentate compound, wherein each interplanar angle is less than about 15°

, and having a structure II;

14. The compound of claim 13 having a structure III:

15. The compound of claim 13 having a structure IV: