Organometallic complex and light-emitting element containing the same
View Patent ↗Organometallic complexes represented by chemical formula 1 are synthesized. In chemical formula 1, R 1 to R 5 , are individually a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, or a heterocyclic group. Each pair of R 1 and R 2 , R 2 and R 3 , and R 4 and R 5 may be bonded each other to form aromatic rings. Y is a heterocyclic group containing nitrogen atoms as hetero atoms. M is atoms of group 9 in the periodic table or atoms of group 10 in the periodic table. When the M is atoms of group 9 in the periodic table, n=2. When the M is atoms of group 10 in the periodic table, n=1. L is a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, or a monoanionic bidentate chelate ligand having a phenol hydroxyl group.
1. An organometallic complex represented by general formula 1,
wherein each of R 1 to R 5 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein Y is a heterocyclic group containing a nitrogen atom as a hetero atom,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is the atom of group 9 in the periodic table, n=2,
wherein when the M is the atom of group 10 in the periodic table, n=1, and
wherein L is selected from the group consisting of a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group and a monoanionic bidentate chelate ligand having a phenol hydroxyl group.
2. An organometallic complex according to claim 1 , wherein each pair of R1 and R2, R2 and R3, and R4 and R5 is bonded each other to form aromatic rings.
3. An organometallic complex according to claim 1 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
4. An organometallic complex according to claim 1 , wherein the M is at least one of an iridium atom and a platinum atom.
5. A phosphorescent material comprising the organometallic complex according to claim 1 .
6. A light-emitting element having a layer comprising the organometallic complex according to claim 1 between a pair of electrodes.
7. An organometallic complex according to claim 1 , wherein the L is represented by at least one of structural formulae 5 to 11.
8. An organometallic complex represented by general formula 2,
wherein R 10 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein Y is a heterocyclic group containing a nitrogen atom as a hetero atom,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is the atoms of group 9 in the periodic table, n=2,
wherein when the M is the atom of group 10 in the periodic table, n=1, and
wherein L is selected from the group consisting of a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenol hydroxyl group.
9. An organometallic complex according to claim 8 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
10. An organometallic complex according to claim 8 , wherein the M is at least one of an iridium atom and a platinum atom.
11. A phosphorescent material comprising the organometallic complex according to claim 8 .
12. A light-emitting element having a layer comprising the organometallic complex according to claim 8 between a pair of electrodes.
13. An organometallic complex according to claim 8 , wherein the L is represented by at least one of structural formulae 5 to 11.
14. An organometallic complex represented by general formula 3,
wherein each of R 1 to R 9 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is the atom of group 9 in the periodic table, n=2,
wherein when the M is the atom of group 10 in the periodic table, n=1, and
wherein L is selected from the group consisting of a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenol hydroxyl group.
15. An organometallic complex according to claim 14 , wherein each pair of R1 and R2, R2 and R3, and R4 and R5 is bonded each other to form aromatic rings.
16. An organometallic complex according to claim 14 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
17. An organometallic complex according to claim 14 , wherein the M is at least one of an iridium atom and a platinum atom.
18. A phosphorescent material comprising the organometallic complex according to claim 14 .
19. A light-emitting element having a layer comprising the organometallic complex according to claim 14 between a pair of electrodes.
20. An organometallic complex according to claim 14 , wherein the L is represented by at least one of structural formulae 5 to 11.
21. An organometallic complexes represented by general formula 4,
wherein each of R 6 to R 10 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is the atom of group 9 in the periodic table, n=2,
wherein when the M is the atom of group 10 in the periodic table, n=1, and
wherein L is selected from the group consisting of a monoanionic bidentate chelate ligand having a beta diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic bidentate chelate ligand having a phenol hydroxyl group.
22. An organometallic complex according to claim 21 , wherein each pair of R6 and R7, R7 and R8, and R8 and R9 is bonded each other to form aromatic rings.
23. An organometallic complex according to claim 21 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
24. An organometallic complex according to claim 21 , wherein the M is at least one of an iridium atom and a platinum atom.
25. A phosphorescent material comprising the organometallic complex according to claim 21 .
26. A light-emitting element having a layer comprising the organometallic complex according to claim 21 between a pair of electrodes.
27. An organometallic complex according to claim 21 , wherein the L is represented by at least one of structural formulae 5 to 11.
28. An organometallic complex represented by general formula 24,
wherein each of R 1 to R 5 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein Y is a heterocyclic group containing a nitrogen atom as a hetero atom,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is the atom of group 9 in the periodic table, n=2, and
wherein when the M is the atom of group 10 in the periodic table, n=1.
29. An organometallic complex according to claim 28 , wherein each pair of R1 and R2, R2 and R3, and R4 and R5 is bonded each other to form aromatic rings.
30. An organometallic complex according to claim 28 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
31. An organometallic complex according to claim 28 , wherein the M is at least one of an iridium atom or a platinum atom.
32. A phosphorescent material comprising the organometallic complex according to claim 28 .
33. A light-emitting element having a layer comprising the organometallic complex according to claim 28 between a pair of electrodes.
34. An organometallic complex represented by general formula 25,
wherein R 10 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group,
wherein Y is a heterocyclic group containing a nitrogen atom as a hetero atom,
wherein M is at least one of atoms of group 9 and group 10 in the periodic table,
wherein when the M is atom of group 9 in the periodic table, n=2, and
wherein when the M is atom of group 10 in the periodic table, n=1.
35. An organometallic complex according to claim 34 , wherein the Y is a heterocyclic group containing at least one of a five-membered ring and a six-membered ring.
36. An organometallic complex according to claim 34 , wherein the M is at least one of an iridium atom and a platinum atom.
37. A phosphorescent material comprising the organometallic complex according to claim 34 .
38. A light-emitting element having a layer comprising the organometallic complex according to claim 34 between a pair of electrodes.
39. A method for forming an organometallic complex comprising the step of:
forming a coordinate bond between a metal and a compound which is represented by general formula 12,
wherein each of R 1 to R 5 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, an alkoxy group, an acyl group, a nitro group, a cyano group, an amino group, a dialkylamino group, a diarylamino group, a vinyl group, an aryl group, and a heterocyclic group, and
wherein Y is a heterocyclic group containing a nitrogen atom as a hetero atom.
40. A method according to claim 39 , wherein each pair of R 1 and R 2 , R 2 and R 3 , and R 4 and R 5 is bonded each other to form aromatic rings.