Blue phosphorescent imidazophenanthridine materials
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 devices comprising these compounds are also described.
1. An iridium complex of the formula
wherein n=1, 2 or 3;
R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , and R 1i 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; and
X-Y is an ancillary ligand.
2. The complex of claim 1 , wherein at least one of R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , and R 1i is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.
3. The complex of claim 2 , wherein at least one of R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , and R 1i is neopentyl.
4. The complex of claim 2 , wherein R 1e is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.
5. The complex of claim 4 , wherein the complex includes a ligand selected from the group consisting of:
6. The complex of claim 5 , where R 1a , R 1b , R 1c , R 1d , R 1f , R 1g , R 1h , and R 1i , are all H.
7. The complex of claim 1 , wherein R 1b is an aryl group having the structure:
wherein Ra, Rb and Rc are independently H, alkyl or aryl;
at least one of Ra and Rb is an alkyl or aryl; and
Ra, Rb and Re can join to form fused rings.
8. The complex of claim 7 , at least one of Ra and Rb is an alkyl.
9. The complex of claim 7 , wherein R 1b is an aryl group with a dihedral angle of more than 70 degrees from the imidazole ring.
10. The complex of claim 7 , wherein Ra and Rb are both alkyl.
11. The complex of claim 10 , wherein Ra and Rb are both methyl.
12. The complex of claim 10 , wherein the Ra and Rb are both isopropyl.
13. The complex of claim 7 , wherein R 1b is an aryl group with a dihedral angle of more than 70 degrees from the imidazole ring and R 1a is alkyl.
14. The complex of claim 7 , wherein the complex is:
15. The complex of claim 7 , wherein the complex is:
16. The complex of claim 7 , wherein the complex is:
17. The complex of claim 1 , wherein R 1a is an electron donating group.
18. The complex of claim 17 , wherein R 1a is methyl.
19. The complex of claim 17 , wherein the complex is:
20. The complex of claim 17 , wherein the complex is selected from the group consisting of:
21. A device, comprising:
an anode;
a cathode; and
an organic emissive layer, disposed between the anode and the cathode, the organic layer further comprising an emissive complex having the formula:
wherein n=1, 2 or 3;
R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , and R 1i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 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; and
X-Y is an ancillary ligand.
22. The device of claim 21 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
23. The device of claim 22 , wherein the host is mCBP.
24. The device of claim 21 , wherein at least one of R 1a , R 1b , R 1c , R 1d , R 1e , R 1f , R 1g , R 1h , and R 1i is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.
25. The device of claim 24 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
26. The device of claim 25 , wherein the host is mCBP.
27. The device of claim 24 , wherein the complex includes a ligand selected from the group consisting of:
where R 1a , R 1b , R 1c , R 1d , R 1f , R 1g , R 1h , and R 1i , and are independently H or substitutions selected from the group of alkyl or aryl.
28. The device of claim 27 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
29. The device of claim 28 , wherein the host is mCBP.
30. The device of claim 21 , wherein R 1b is an aryl group having the structure:
wherein Ra, Rb and Rc are independently H, alkyl or aryl;
at least one of Ra and Rb is an alkyl or aryl; and
Ra, Rb and Rc can join to form fused rings.
31. The device of claim 30 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
32. The device of claim 31 , wherein the host is mCBP.
33. The complex of claim 30 , wherein the complex is:
34. The device of claim 33 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
35. The device of claim 34 , wherein the host is mCBP.
36. The device of claim 21 wherein R 1a is an electron donating group.
37. The device of claim 36 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
38. The device of claim 37 , wherein the host is mCBP.
39. The complex of claim 36 , wherein the complex is:
40. The device of claim 39 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
41. The device of claim 40 , wherein the host is mCBP.
42. The complex of claim 36 , wherein the complex is selected from the group consisting of:
43. The device of claim 42 , wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.
44. The device of claim 43 , wherein the host is mCBP.