Germanium-containing red emitter materials for organic light emitting diode
Organometallic compounds comprising a germanium-containing substituent are provided. The compounds may be used in organic light emitting devices to provide improved device efficiency, line shape and lifetime. In particular, the compounds comprise a phenylquinoline or phenylisoquinoline ligand having a germanium-containing substituent on the quinoline or isoquinoline portion of the ligand. These compounds may be advantageously used as red emitters in the emissive layer of organic light emitting devices.
1. A compound having the formula M(L) x (L 1 ) y (L 2 ) z :
wherein the ligand L is
wherein the ligand L 1 is
wherein the ligand L 2 is an ancillary ligand;
wherein each L, L 1 and L 2 can be the same or different;
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein R is a fused carbocyclic or heterocyclic ring further substituted with a substituent containing Ge;
wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R A , R B , and R C may represent mono, di, tri, or tetra substitutions;
wherein each of R A , R B , and R C are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein adjacent substitutents of R A , R B , and R C are optionally joined to form a fused ring; and
wherein the ligand L is bidentately coordinated to the metal M.
2. The compound of claim 1 , wherein M is Ir.
3. The compound of claim 1 , wherein L 2 is a monoanionic bidentate ligand.
4. The compound of claim 1 , wherein L 2 is
and
wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
5. The compound of claim 1 , wherein Ge is directly attached to the fused carbocyclic or heterocyclic ring R.
6. The compound of claim 1 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
7. The compound of claim 1 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
8. The compound of claim 1 , wherein the compound is homoleptic.
9. The compound of claim 1 , wherein the compound is heteroleptic.
10. The compound of claim 1 , wherein the compound is selected from the group consisting of:
11. The compound of claim 1 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
12. The compound of claim 11 , wherein each of R′, R″, and R′″ are the same.
13. The compound of claim 11 , wherein each of R′, R″, and R′″ is an alkyl group having 3 or less carbon atoms.
14. The compound of claim 11 , wherein each of R′, R″, and R′″ is different.
15. 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 having the formula M(L) x (L 1 ) y (L 2 ) z :
wherein the ligand L is
wherein the ligand L 1 is
wherein the ligand L 2 is an ancillary ligand;
wherein each L, L 1 and L 2 can be the same or different;
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein R is a fused carbocyclic or heterocyclic ring further substituted with a substituent containing Ge;
wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R A , R B , and R C may represent mono, di, tri, or tetra substitutions;
wherein each of R A , R B , and R C are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein adjacent substituents of R A , R B , and R C are optionally joined to form a fused ring; and
wherein the ligand L is bidentately coordinated to the metal M.
16. The first device of claim 15 , wherein L 2 is
and
wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
17. The first device of claim 15 , wherein Ge is directly attached to the fused carbocyclic or heterocyclic ring R.
18. The first device of claim 15 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
19. The first device of claim 15 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
20. The first device of claim 15 , wherein the compound is selected from the group consisting of:
21. The first device of claim 15 , wherein the first device is a consumer product.
22. The first device of claim 15 , wherein the first device is an organic light emitting device.
23. The first device of claim 15 , wherein the compound has the formula:
wherein each of R′, R″, and R′″ is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, and heteroaryl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein m is 1, 2, or 3.
24. The first device of claim 23 , wherein each of R′, R″, and R′″ are the same.
25. The first device of claim 23 , wherein each of R′, R″, and R′″ is an alkyl group having 3 or less carbon atoms.
26. The first device of claim 23 , wherein each of R′, R″, and R′″ is different.
27. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.
28. The first device of claim 27 , wherein the organic layer further comprises a host.
29. The first device of claim 28 , wherein the host is a compound that comprises at least one of the chemical groups selected from the group consisting of:
wherein each of R′″ 1 , R′″ 2 , R′″ 3 , R′″ 4 , R′″ 5 , R′″ 6 and R′″ 7 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein k is an integer from 0 to 20; and
wherein each of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 and X 8 are independently selected from the group consisting of CH and N.
30. The first device of claim 28 , wherein the host is a metal complex.
31. The first device of claim 30 , wherein the metal complex is selected from the group consisting of:
wherein (O—N) is a bidentate ligand having metal coordinated to atoms O and N;
wherein L is an ancillary ligand; and
wherein m is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
32. The first device of claim 30 , wherein the host is a metal 8-hydroxyquinolate.