Heteroleptic phosphorescent emitters
Heteroleptic compounds containing phenylpyridine and phenylbenzimidazole are provided. The compounds may be used in organic light emitting devices, particularly as emissive dopants in the emissive layer of such devices.
1. A heteroleptic iridium compound Ir(L1) n (L2) 3-n having the formula:
wherein n=1 or 2;
wherein
is L1;
wherein
is L2;
wherein R 2 , R 3 , R 4 and R 5 may represent mono, di, tri, or tetra substitutions; and
wherein R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
wherein R 1 is
wherein X 1 and X 2 are independently selected from C and N;
wherein Y 1 is not hydrogen; and
wherein Y 1 may be joined to other substituents on the aryl ring.
2. The compound of claim 1 , wherein n=1.
3. The compound of claim 1 , wherein the compound has the formula:
wherein R 4 is hydrogen or methyl.
4. The compound of claim 1 , wherein each of R 2 , R 3 , and R 5 are hydrogen.
5. The compound of claim 1 , wherein L1 is selected from the group consisting of:
6. The compound of claim 5 , wherein L2 is selected from the group consisting of:
7. The compound of claim 1 , wherein L2 is selected from the group consisting of:
8. The compound of claim 1 , wherein L1 is selected from the group consisting of:
9. The compound of claim 8 , wherein L2 is selected from the group consisting of:
10. The compound of claim 1 , wherein L2 is selected from the group consisting of:
11. The compound of claim 1 , wherein the compound is selected from the group consisting of:
12. The compound of claim 1 , wherein the compound is selected from the group consisting of:
13. The compound of claim 1 , wherein the compound has an emission spectrum with a narrower full width at half maximum than either
corresponding compound of formula
14. The compound of claim 1 , wherein the compound has a lower sublimation temperature than either
corresponding compound of formula
15. The compound of claim 1 , wherein the compound is capable of being a green emissive dopant.
16. An organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer comprising a heteroleptic iridium compound Ir(L1) n (L2) 3-n having the formula:
wherein n=1 or 2;
wherein
is L1;
wherein
is L2;
wherein R 2 , R 3 , R 4 , and R 5 may represent mono, di, tri, or tetra substitutions; and
wherein R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
wherein R 1 is
wherein X 1 and X 2 are independently selected from C and N;
wherein Y 1 is not hydrogen; and
wherein Y 1 may be joined to other substituents on the aryl ring.
17. The device of claim 16 , wherein the organic layer is an emissive layer and the compound having the formula
is an emissive compound.
18. The device of claim 16 , wherein the compound is selected from the group consisting of:
19. The device of claim 16 , wherein the compound is selected from the group consisting of:
20. The device of claim 16 , wherein the organic layer further comprises a host.
21. The device of claim 20 , wherein the host has the formula:
wherein R 1 and R 2 represent, independently, mono, di, tri or tetra substitutions selected from alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl, or no substitution; and
wherein at least one of R 1 and R 2 includes a triphenylene group.
22. The device of claim 20 , wherein the host has the formula:
wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, a non-fused aryl group, or a non-fused heteroaryl group having one or more meta-substituents, wherein at least one of R 1 , R 2 , and R 3 is not hydrogen; and
wherein each meta-substituent is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups.
23. A consumer product comprising a device, the device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic layer comprising a heteroleptic iridium compound Ir(L1) n (L2) 3-n compound having the formula:
wherein n=1 or 2;
wherein
is L1;
wherein
is L2;
wherein R 2 , R 3 , R 4 , and R 5 may represent mono, di, tri, or tetra substitutions; and
wherein R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
wherein R 1 is
wherein X 1 and X 2 are independently selected from C and N;
wherein Y 1 is not hydrogen; and
wherein Y 1 may be joined to other substituents on the aryl ring.