	US 7,601,436 B2
	Carbene metal complexes as OLED materials
Peter Djurovich, Long Beach, Calif. (US); Jui-Yi Tsai, Monroeville, Pa. (US); Chun Lin, Irwin, Pa. (US); Jason Brooks, Lambertville, N.J. (US); Bert Alleyne, Monroeville, Pa. (US); Mark E. Thompson, Anaheim Hills, Calif. (US); Peter B. MacKenzie, Murrysville, Pa. (US); and Bin Ma, Monroeville, Pa. (US)
Assigned to The University of Southern California, Los Angeles, Calif. (US); and Universal Display Corporation, Ewing, N.J. (US)
Filed on Jan. 10, 2005, as Appl. No. 11/32,887.
Application 11/032887 is a continuation in part of application No. 10/880384, filed on Jun. 28, 2004, granted, now 7,393,599.
Application 10/880384 is a continuation in part of application No. 10/849301, filed on May 18, 2004, granted, now 7,491,823.
Prior Publication US 2005/0258433 A1, Nov. 24, 2005
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/54 (2006.01); C09K 11/06 (2006.01)

U.S. Cl. 428—690 [428/917; 313/504; 257/40; 257/E51.043; 257/E51.044; 548/103; 548/108; 546/4]

15 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 having one or more carbene ligands coordinated to a metal center, and wherein the compound has the structure:

wherein M is a metal;ring D is an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring; A is C, N, or P; wherein ring D can be optionally substituted with one or more substituents R₂; andR₁and R₂are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF₃, CO₂R′, C(O)R′, C(O)NR′₂, NR′₂, NO₂, OR′, SR′, SO₂, SOR′, SO₃R′, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R₃is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and additionally or alternatively, two R groups on the same or adjacent ring, together form a 5 or 6-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl; and wherein said cyclic group is optionally substituted by one or more substituents J;each substituent J is independently selected from the group consisting of R′, CN, CF₃, C(O)OR′, C(O)R′, C(O)NR′₂, NR′₂, NO₂, OR′, SR′, SO₂, SOR′, or SO₃R′, and additionally, or alternatively, two J groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;each R′ is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;α is 0, 1, 2, 3, or 4; c is 0, 1, or 2;(X-Y) is a photoactive ligand or an ancillary ligand; m is a value from 1 to the maximum number of ligands that may be attached to metal M; and m+n is the maximum number of ligands that may be attached to metal M.