Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting diode devices comprising these compounds are also described.
1. A phosphorescent compound comprising a metal and a monoanionic, bidentate ligand as set forth below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;
wherein:
E 1b , E 1c , E 1q , and E 1e-o are each independently C or N; and
R 1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; provided that R 1a-i is other than H when attached to N.
2. The compound according to claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au, and the bidentate ligand is selected from Set 2;
3. The compound according to claim 2 , wherein the bidentate ligand is of the formula gs1-1.
4. The compound according to claim 2 , wherein the metal is Ir or Pt.
5. The compound according to claim 2 , wherein the compound is a homoleptic Ir complex.
6. The compound according to claim 2 , wherein the compound is a heteroleptic Ir complex.
7. The compound according to claim 6 , wherein the compound includes a acetylacetonate or a substituted acetylacetonate as a ligand.
8. The compound according to claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au, and at least one of R 1a-i is a 2,6-di-substituted aryl group.
9. The compound according to claim 2 , wherein the metal is selected from the group consisting of Ir and Pt, and wherein the bidentate ligand is of formula gs1-1 and R 1b is a 2,6-di-substituted aryl group.
10. The compound according to claim 9 , wherein the 2,6-di-substituted aryl group is selected from the group consisting of 2,6-dimethylphenyl; 2,4,6-trimethylphenyl; 2,6-di-isopropylphenyl; 2,4,6-triisopropylphenyl; 2,6-di-isopropyl-4-phenylphenyl; 2,6-dimethyl-4-phenylphenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-diphenylphenyl; 2,6-diphenyl-4-isopropylphenyl; 2,4,6-triphenylphenyl; 2,6-di-isopropyl-4-(4-isopropylphenyl)phenyl; 2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and 2,6-di-(3,5-dimethylphenyl)phenyl.
11. A compound selected from Set 3, wherein acac is acetylacetonate;
12. An organic light-emitting device comprising any of the compounds of claim 1 or 11 .
13. The compound of claim 1 , wherein R 1a-i are each independently H, fluoro, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl.
14. The compound of claim 13 , wherein the metal is iridium.
15. The compound of claim 13 , wherein each of E 1f-o and E 1q is carbon.
16. The compound of claim 15 , wherein the metal is iridium.
17. The compound of claim 2 , wherein R 1a-i are each independently H, fluoro, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl.
18. The compound of claim 17 , wherein the metal is iridium.
19. The compound of claim 3 , wherein R 1a-i are each independently H, fluoro, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl.
20. The compound of claim 19 , wherein the metal is iridium.
21. An organic light-emitting device comprising the compound of claim 2 .
22. An organic light-emitting device comprising the compound of claim 3 .
23. An organic light-emitting device comprising the compound of claim 13 .
24. An organic light-emitting device comprising the compound of claim 14 .
25. An organic light-emitting device comprising the compound of claim 17 .
26. An organic light-emitting device comprising the compound of claim 18 .
27. An organic light-emitting device comprising the compound of claim 19 .
28. An organic light-emitting device comprising the compound of claim 20 .