Organic electroluminescent materials and devices
Compounds are provided that comprise a ligand having a 5-substituted 2-phenylquinoline. In particular, the 2-phenylquinoline may be substituted with a cycloalkyl containing group 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 comprising a ligand L having the formula:
wherein A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A can represent mono, di, tri, or tetra substitutions;
wherein each of R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R B is selected from the group consisting of partially fluorinated alkyl having at least 2 carbon atoms and silyl; and
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40.
2. The compound of claim 1 , wherein A is phenyl.
3. The compound of claim 1 , wherein M is Ir.
4. The compound of claim 1 , wherein the compound has the formula:
wherein L′ is an ancillary ligand; and
wherein m is 1, 2, or 3.
5. The compound of claim 4 , wherein L′ is a monoanionic bidentate ligand.
6. The compound of claim 4 , wherein L′ is
and wherein each of R 1 , R 2 , and R 3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl.
7. The compound of claim 4 , wherein the compound has the formula:
wherein each R 1 , R 2 , R 3 , R 5 , R 6 and R 7 is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl; and
wherein m is 1, 2, or 3.
8. The compound of claim 7 , wherein each of R 1 and R 3 is a branched alkyl with branching at a position further than the α position to the carbonyl group.
9. The compound of claim 7 , wherein each of R 5 , R 6 and R 7 is independently selected from methyl and hydrogen, and at least one of R 5 , R 6 and R 7 is methyl.
10. The compound of claim 7 , wherein each of R 5 and R 7 is methyl, and R 6 is hydrogen.
11. The compound of claim 7 , wherein each of R 5 and R 6 is methyl, and R 7 is hydrogen.
12. The compound of claim 7 , wherein each of R 5 , R 6 and R 7 is methyl.
13. The compound of claim 1 , wherein R B is a partially fluorinated alkyl group having at least 4 carbon atoms.
14. The compound of claim 1 , wherein R B is a partially fluorinated alkyl group having at least 3 carbon atoms.
15. The compound of claim 1 , wherein the compound is selected from
16. The compound of claim 1 , wherein R B is silyl.
17. A first device comprising an organic light emitting device, 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 A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A can represent mono, di, tri, or tetra substitutions;
wherein each of R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R B is selected from the group consisting of partially fluorinated alkyl having at least 2 carbon atoms and silyl; and
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40.
18. The first device of claim 17 , wherein the compound is selected from the group consisting of:
19. A consumer product comprising an organic light emitting device, 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 A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R A can represent mono, di, tri, or tetra substitutions;
wherein each of R A is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R B is selected from the group consisting of partially fluorinated alkyl having at least 2 carbon atoms and silyl; and
wherein the ligand L is coordinated to a metal M having an atomic number greater than 40.
20. The consumer product of claim 19 , wherein the consumer product is one of a flat panel display, a computer monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads up display, a fully transparent display, a flexible display, a laser printer, a telephone, a cell phone, a personal digital assistant (PDA), a laptop computer, a digital camera, a camcorder, a viewfinder, a vehicle, a wall, theater or stadium screen, and a sign.