US 7,491,823 B2
Luminescent compounds with carbene ligands
Mark E. Thompson, Anaheim, Calif. (US); Arnold Tamayo, Glendale, Calif. (US); Peter Djurovich, Los Angeles, Calif. (US); and Tissa Sajoto, Los Angeles, Calif. (US)
Assigned to The University of Southern California, Los Angeles, Calif. (US)
Filed on May 18, 2004, as Appl. No. 10/849,301.
Prior Publication US 2005/0260441 A1, Nov. 24, 2005
Int. Cl. C09K 11/06 (2006.01); H01L 51/54 (2006.01)
U.S. Cl. 546—4  [548/103; 548/108; 548/402; 549/3; 549/209; 549/212] 34 Claims
 
1. A compound selected from the group consisting of:

OG Complex Work Unit Drawing
wherein
Z3 is selected from the group consisting of O, S, N—R6, or P—R6, wherein R6 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, O—R′, N(R′)2, SR′, C(O)R′, C(O)OR′, C(O)NR′2, CN, CF3, NO2, SO2, SOR′, SO3R′, halo, and heteroaryl; each R′ is independently selected from H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl; and
A is independently selected from C, N, O, P, or S;
(X—Y) is a bidentate photoactive ligand or a bidentate ancillary ligand;
ring B is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring, wherein ring B can be optionally substituted with one or more substituents R14; and
ring D is independently a cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring with at least one carbon atom coordinated to metal M, wherein ring D can be optionally substituted with one or more substituents R15; and
R14 and R15 are independently selected from alkyl, alkenyl, alkynyl, aralkyl, R′, O—R′, N(R′)2, SR′, C(O)R′, C(O)OR′, C(O)NR′2, CN, CF3, NO2, SO2, SOR′, SO3R′, halo, aryl, and heteroaryl; each R′ is independently selected from H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl; or
alternatively, two R14 groups on adjacent ring atoms and R15 groups on adjacent ring atoms form a fused 5- or 6-membered 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;
b is 0, 1, 2, 3, or 4;
e is 0, 1, 2, or 3;
m has a value from 1 to the maximum number of ligands that may be attached to the metal; and m+n is the maximum number of ligands that may be attached to metal M.