5-substituted 2 phenylquinoline complexes materials for light emitting diode
Compounds are provided that comprise a ligand having a 5-substituted 2-phenylquinoline. In particular, the 2-phenylquinoline may be substituted with a bulky alkyl at the 5-position. These compounds may be used in organic light emitting devices, in particular as red emitters in the emissive layer of such devices, to provide devices having improved properties.
1. A compound having the formula:
wherein each of R 1 , R 2 , R 3 , R 5 , R 6 and R 7 is independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R 4 is selected from the group consisting of isopropyl, isobutyl, and t-butyl; and
wherein m=2.
2. The compound of claim 1 , wherein each of R 1 and R 3 are a branched alkyl with branching at a position further than the α position to the carbonyl group.
3. The compound of claim 1 , wherein each of R 5 , R 6 and R 7 are independently selected from methyl and hydrogen, and at least one of R 5 , R 6 and R 7 is methyl.
4. The compound of claim 1 , wherein each of R 5 and R 7 are methyl, and R 6 is hydrogen.
5. The compound of claim 1 , wherein each of R 5 and R 6 are methyl, and R 7 is hydrogen.
6. The compound of claim 1 , wherein each of R 5 , R 6 and R 7 are methyl.
7. The compound of claim 1 , wherein R 4 is isobutyl.
8. The compound of claim 1 , wherein R 4 is isopropyl.
9. The compound of claim 1 , wherein the compound is selected from the group consisting of:
10. The compound of claim 1 , wherein each of R 1 , R 2 , R 3 , R 5 , R 6 and R 7 is independently selected from the group consisting of hydrogen, deuterium, and alkyl.
11. The composition of claim 1 , wherein the compound is selected from the group consisting of:
12. The composition of claim 1 , wherein the compound is
13. The compound of claim 1 , wherein R 4 is t-butyl.
14. A first device comprising an organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L having the formula:
wherein each of R 1 , R 2 , R 3 , R 5 , R 6 and R 7 is independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R 4 is selected from the group consisting of isopropyl, t-butyl, and isobutyl; and
wherein m=2.
15. The first device of claim 14 , wherein the compound is selected from the group consisting of:
16. The first device of claim 14 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.
17. The first device of claim 16 , wherein the organic layer further comprises a host.
18. The first device of claim 17 , wherein the host is a metal 8-hydroxyquinolate.
19. The first device of claim 18 , wherein the host is:
20. The first device of claim 14 , wherein the first device is a consumer product.
21. The first device of claim 14 , wherein the first device is an organic light emitting device.
22. A compound comprising a ligand L having the formula:
wherein A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A may represent mono, di, tri, or tetra substitutions;
wherein each of R A is independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R B is selected from the group consisting of amino and silyl;
wherein, when R B is silyl, a Si atom of the silyl is bonded directly to the quinoline ring of Formula I;
wherein, when R B is amino, a N atom of the amino is bonded directly to the quinoline ring of Formula I; and
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40.
23. The compound of claim 22 , wherein R B is amino.
24. The compound of claim 22 , wherein R B is silyl.
25. The compound of claim 22 , wherein the compound has a structure according to Formula III:
wherein each of R 1 , R 2 , R 3 , R 5 , R 6 and R 7 is independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R 4 is selected from the group consisting of amino and silyl;
wherein, when R 4 is silyl, a Si atom of the silyl is bonded directly to the quinoline ring of Formula III; and
wherein, when R 4 is amino, a N atom of the amino is bonded directly to the quinoline ring of Formula III.
26. The compound of claim 22 , wherein the compound is selected from the group consisting of: