Metal complex compound and organic electroluminescence device using the compound

1. A metal complex compound, which is represented by formula (1), comprising two tridentate chelate ligands

wherein:

a solid line represents a covalent bond, and a dotted line represents a coordinate bond;

M represents a trivalent metal atom selected from the group consisting of Co, Rh and Ir;

an L 1 L 2 L 3 M part comprises a structure represented by formula (5)

wherein:

M is as defined above; and

R 1 to R 11 each independently represent a hydrogen atom, a cyano group, a halogen atom, an alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkylamino group which has 1 to 12 carbon atoms, an arylamino group which has 6 to 20 carbon atoms and which may have a substituent, an alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, a halogenated alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, an aryloxy group which has 6 to 20 carbon atoms and which may have a substituent, an aromatic hydrocarbon group which has 6 to 20 carbon atoms and which may have a substituent, a heterocyclic group which has 3 to 20 carbon atoms and which may have a substituent, a halogenated alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkyl group which has 2 to 12 carbon atoms and which may have a substituent, an alkyl group which has 2 to 12 carbon atoms and which may have a substituent, or a cycloalkyl group which has 3 to 20 carbon atoms and which may have a substituent, and adjacent groups may be bonded to each other to form a cyclic structure; and

an L 4 L 5 L 6 M part comprises a structure represented by formula (12)

wherein:

M is as defined above;

R 1 to R 7 each independently represent a hydrogen atom, a cyano group, a halogen atom, an alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkylamino group which has 1 to 12 carbon atoms, an arylamino group which has 6 to 20 carbon atoms and which may have a substituent, an alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, a halogenated alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, an aryloxy group which has 6 to 20 carbon atoms and which may have a substituent, an aromatic hydrocarbon group which has 6 to 20 carbon atoms and which may have a substituent, a heterocyclic group which has 3 to 20 carbon atoms and which may have a substituent, a halogenated alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkenyl group which has 2 to 12 carbon atoms and which may have a substituent, an alkynyl group which has 2 to 12 carbon atoms and which may have a substituent, or a cycloalkyl group which has 3 to 20 carbon atoms and which may have a substituent, and adjacent groups may be bonded to each other to form a cyclic structure;

X represents O;

Y represents a group comprising an atom selected from the group consisting of C, N, O, Si, P, S, Ge, As, and Se; and

R 10 is absent.

2. A metal complex compound, which is represented by formula (2), comprising two tridentate chelate ligands

wherein:

a solid line represents a covalent bond, and a dotted line represents a coordinate bond;

M represents a trivalent metal atom selected from the group consisting of Co, Rh and Ir;

an L 7 L 8 L 9 M part comprises a structure represented by formula (5)

wherein:

M is as defined above; and

R 1 to R 11 each independently represent a hydrogen atom, a cyano group, a halogen atom, an alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkylamino group which has 1 to 12 carbon atoms, an arylamino group which has 6 to 20 carbon atoms and which may have a substituent, an alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, a halogenated alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, an aryloxy group which has 6 to 20 carbon atoms and which may have a substituent, an aromatic hydrocarbon group which has 6 to 20 carbon atoms and which may have a substituent, a heterocyclic group which has 3 to 20 carbon atoms and which may have a substituent, a halogenated alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkenyl group which has 2 to 12 carbon atoms and which may have a substituent, an alkynyl group which has 2 to 12 carbon atoms and which may have a substituent, or a cycloalkyl group which has 3 to 20 carbon atoms and which may have a substituent, and adjacent groups may be bonded to each other to form a cyclic structure;

an L 10 L 11 L 12 M part comprises a structure represented by formula (13) or (14):

wherein:

M is as defined above; and

R 1 to R 9 each independently represent a hydrogen atom, a cyano group, a halogen atom, an alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkylamino group which has 1 to 12 carbon atoms, an arylamino group which has 6 to 20 carbon atoms and which may have a substituent, an alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, a halogenated alkoxy group which has 1 to 12 carbon atoms and which may have a substituent, an aryloxy group which has 6 to 20 carbon atoms and which may have a substituent, an aromatic hydrocarbon group which has 6 to 20 carbon atoms and which may have a substituent, a heterocyclic group which has 3 to 20 carbon atoms and which may have a substituent, a halogenated alkyl group which has 1 to 12 carbon atoms and which may have a substituent, an alkenyl group which has 2 to 12 carbon atoms and which may have a substituent, an alkynyl group which has 2 to 12 carbon atoms and which may have a substituent, or a cycloalkyl group which has 3 to 20 carbon atoms and which may have a substituent, and adjacent groups may be bonded to each other to form a cyclic structure;

X represents O;

Y represents a group comprising an atom selected from the group consisting of C, N, O, Si, P, S, Ge, As, and Se;

R 10 is absent; and

a structure excluded from examples of formula (2) is

3. An organic electroluminescence device, comprising an organic thin film layer which has one layer or a plurality of layers including at least a light emitting layer and is disposed between a pair of electrodes, wherein:

at least one layer of the organic thin film layer comprises the metal complex compound according to claim 1 ; and

light is emitted by applying a voltage between both the electrodes.

4. An organic electroluminescence device according to claim 3 , wherein the light emitting layer comprises the metal complex compound.

5. An organic electroluminescence device according to claim 3 , wherein the organic electroluminescence device emits blue light.

6. An organic electroluminescence device according to claim 3 , wherein the layer comprises the metal complex compound is formed by application.

7. A metal complex compound according to claim 2 , wherein the L 10 L 11 L 12 M part comprises a structure represented by formula (13).

8. An organic electroluminescence device, comprising an organic thin film layer which has one layer or a plurality of layers including at least a light emitting layer and is disposed between a pair of electrodes, wherein:

at least one layer of the organic thin film layer comprises the metal complex compound according to claim 2 ; and

light is emitted by applying a voltage between both the electrodes.

9. An organic electroluminescence device according to claim 8 , wherein the light emitting layer comprises the metal complex compound.

10. An organic electroluminescence device according to claim 8 , wherein the organic electroluminescence device emits blue light.

11. An organic electroluminescence device according to claim 8 , wherein the layer comprises the metal complex compound is formed by application.

12. The metal complex compound according to claim 1 , wherein Y represents O.

13. The metal complex compound according to claim 1 , wherein M is Ir.

14. The metal complex compound according to claim 1 , wherein M is Co.

15. The metal complex compound according to claim 1 , wherein M is Rh.

16. A metal complex compound according to claim 2 , wherein the L 10 L 11 L 12 M part comprises a structure represented by formula (14).

17. The metal complex compound according to claim 2 , wherein Y represents O.

18. The metal complex compound according to claim 2 , wherein R 8 and R 9 represent H.

19. The metal complex compound according to claim 2 , wherein M is Ir.

20. The metal complex compound according to claim 2 , wherein M is Co.

21. The metal complex compound according to claim 2 , wherein M is Rh.

22. A metal complex compound, selected from the following formulae (1)-(4), (5) and (8)-(11):