Electroluminescent iridium compounds and devices made therefrom
View Patent ↗Provided are complexes of the formula: where R 1 is H, R 4 , OR 4 , N(R 4 ) 2 or CHAr 2 ; R 2 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN; R 3 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN; R 4 is the same or different at each occurrence and is H, alkyl, or aryl, or adjacent R 4 groups can join together to form a 5- or 6-membered ring, or adjacent R 4 groups can join together to form a 5- or 6-membered ring; or adjacent R 4 groups can join together to form a multicyclic moiety; each Ar is independently an aryl group; L′ is a polydentate ligand that is not a phenylpyridine, phenylpyrimidine, or phenylquinoline; L″ is a monodentate ligand, and is not a phenylpyridine, and phenylpyrimidine, or phenylquinoline; m is 1, 2 or 3; n is an integer from 1 through 20; y is 0, 1 or 2; and z is 0 or an integer from 1 through 4; with the proviso that the compound is charge neutral and the iridium is hexacoordinate.
1. A complex having Formula I
wherein:
R 1 is indole, indoline, carbazole, tetrahydrocarbazole, phenanthroline, phenazine, phenanthridine, quinoxaline, pyrrole, azole, oxazole, or pyridine, each of which is attached via nitrogen; or R 1 is CHAr 2 ;
R 2 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN;
R 3 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN;
R 4 is the same or different at each occurrence and is H, alkyl, or aryl;
each Ar is independently an aryl group;
L′ is a polydentate ligand that is not a phenylpyridine, phenylpyrimidine, or phenylquinoline;
L″ is a monodentate ligand, and is not a phenylpyridine, phenylpyrimidine, or phenylquinoline;
m is 1, 2 or 3;
n is an integer from 1 through 20;
y is 0, 1 or 2; and
z is 0 or an integer from 1 through 4, with the proviso that the compound is charge neutral and the iridium is hexacoordinate.
2. The complex of claim 1 wherein R 2 and R 3 are independently selected from H, CF 3 , C 2 F 3 , n-C 3 F 7 , i-C 3 F 7 , C 4 F 9 , CF 3 SO 2 , COOR 4 and CN.
3. The complex of claim 1 wherein R 4 is phenyl.
4. The complex of claim 1 wherein m is 3, y is 0, and z is 0.
5. The complex of claim 1 wherein m is 2, y is 1, z is 0, and L′ is a monoanionic bidentate ligand.
6. The complex of claim 2 wherein L′ has a coordinating group selected from amino, imino, amido, alkoxide, carboxylate, phosphino, and thiolate.
7. The complex of claim 5 wherein L′ is selected from β-enolate ligands, N-analogs of β-enolate ligands, S-analogs of β-enolate ligands, aminocarboxylate ligands, iminocarboxylate ligands, salicylate ligands, hydroxyquinolinate ligands, S-analogs of hydroxyquinolinate ligands, phosphinoalkoxide ligands, and a ligand coordinated through a carbon atom that is part of an aromatic group.
8. The complex of claim 6 wherein L′ has Formula VII:
9. The complex of claim 1 wherein m is 1, y is 1, and z is 2.
10. The complex of claim 9 wherein at least one L″ is a hydride.
11. A compound of the formula:
wherein:
R 1 is CHAr 2 ;
R 2 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN;
R 3 is H, C n F 2n+1 , C n F 2n+1 SO 2 , COOR 4 , or CN;
wherein each R 4 is the same or different at each occurrence and is H, alkyl, or aryl; and
each Ar is independently an aryl group.
12. An organic electronic device having at least one complex of claim 1 .
13. An article useful in the manufacture of an organic electronic device comprising at least one layer comprising at least one complex of claim 1 .
14. A composition comprising at least one complex of claim 1 .
15. The composition of claim 14 further comprising at least one of solvent, processing aid, charge transporting material, and charge blocking material.