Aromatic amine derivative and organic electroluminescence element using same

1. An aromatic amine derivative represented by a formula (1):

wherein:

R 1 is represented by a formula (2);

any one of R 2 to R 5 and R 7 to R 10 is represented by the formula (2), and the remaining ones of R 2 to R 5 and R 7 to R 10 each independently represent: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and

R 6 represents: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;

wherein:

L 1 , L 2 and L 3 each independently represent a single bond, a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

Ar 1 is a monovalent substituent having a partial structure represented by a formula (3):

wherein:

X represents an oxygen atom or a sulfur atom; and

A and B represent a six-membered ring; the six-membered ring represented by A and B is optionally fused with another ring; and

Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent substituent having a partial structure represented by the formula (3).

2. The aromatic amine derivative according to claim 1 , wherein R 1 and R 3 are represented by the formula (2).

3. The aromatic amine derivative according to claim 1 , wherein R 1 and R 8 are represented by the formula (2).

4. The aromatic amine derivative according to claim 1 , wherein the monovalent substituent having the partial structure represented by the formula (3) is a monovalent residue represented by a formula (4):

wherein:

X represents an oxygen atom or a sulfur atom;

R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, with the proviso that, in the formula (2); when Ar 1 is a monovalent residue of the formula (4), one of R 11 to R 18 is a single bond to be bonded to L 1 ; and when Ar e is a monovalent residue of the formula (4), one of R 11 to R 18 is a single bond to be bonded to L 2 ; and

at least one combination of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 optionally forms a saturated or unsaturated ring.

5. An organic electroluminescence device comprising:

a cathode;

an anode; and

an organic compound layer interposed between the cathode and the anode,

wherein the organic compound layer comprises the aromatic amine derivative according to claim 1 .

6. The organic electroluminescence device according to claim 5 , wherein the organic compound layer comprises a plurality of organic thin-film layers comprising an emitting layer, and

wherein at least one of the plurality of organic thin-film layers comprises the aromatic amine derivative.

7. The organic electroluminescence device according to claim 6 , wherein at least one of the plurality of organic thin-film layers comprises the aromatic amine derivative and an anthracene derivative represented by a formula (20):

wherein:

Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted fused ring group having 10 to 30 ring atoms, or a group provided by combining the monocyclic group and the fused ring group; and

R 101 to R 108 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted fused ring group having 10 to 30 ring atoms, a group provided by combining the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted silyl group.

8. The organic electroluminescence device according to claim 7 , wherein, in the formula (20), Ar 11 and Ar 12 are each independently a substituted or unsubstituted fused ring group having 10 to 30 ring atoms.

9. The organic electroluminescence device according to claim 7 , wherein, in the formula (20), one of Ar 11 and Ar 12 is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other of Ar 11 and Ar 12 is a substituted or unsubstituted fused ring group having 10 to 30 ring atoms.

10. The organic electroluminescence device according to claim 9 , wherein, in the formula (20), Ar 12 is selected from a naphthyl group, phenanthryl group, benzoanthryl group and dibenzofuranyl group, and Ar 11 is an unsubstituted phenyl group or a phenyl group substituted by at least one of the substituted or unsubstituted monocyclic group having 5 to 30 ring atoms and the substituted or unsubstituted fused ring group having 10 to 30 ring atoms.

11. The organic electroluminescence device according to claim 9 , wherein, in the formula (20), A 12 is a substituted or unsubstituted fused ring group having 10 to 30 ring atoms and Ar 11 is an unsubstituted phenyl group.

12. The organic electroluminescence device according to claim 7 , wherein, in the formula (20), Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.

13. The organic electroluminescence device according to claim 12 , wherein, in the formula (20), Ar 11 and Ar 12 are each independently a substituted or unsubstituted phenyl group.

14. The organic electroluminescence device according to claim 13 , wherein, in the formula (20), Ar 11 is an unsubstituted phenyl group and Ar 12 is a phenyl group having at least one of the substituted or unsubstituted monocyclic group having 5 to 30 ring atoms and the substituted or unsubstituted fused ring group having 10 to 30 ring atoms as a substituent.

15. The organic electroluminescence device according to claim 13 , wherein, in the formula (20), Ar 11 and Ar 12 are each independently a phenyl group having at least one of the substituted or unsubstituted monocyclic group having 5 to 30 ring atoms and the substituted or unsubstituted fused ring group having 10 to 30 ring atoms as a substituent.

16. The aromatic amine derivative according to claim 1 , wherein R 1 is represented by the formula (2), and

wherein any one of R 3 , R 4 , R 5 , R 8 , R 9 and R 10 is represented by the formula (2).

17. The aromatic amine derivative according to claim 1 , wherein R 1 is represented by the formula (2), and

wherein any one of R 3 and R 8 is represented by the formula (2).

18. The aromatic amine derivative according to claim 4 , wherein the monovalent residue of the formula (4) is represented by a formula (4A), (4B), (4C), or (4D):

wherein:

R 11 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and

at least one combination of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 optionally forms a saturated or unsaturated ring.

19. The aromatic amine derivative according to claim 4 , wherein the monovalent residue of the formula (4) is represented by a formula (4A):

wherein:

R 12 to R 18 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and

at least one combination of R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 optionally forms a saturated or unsaturated ring.

20. The aromatic amine derivative according to claim 4 , wherein R 1 is represented by the formula (2), and any one of R 3 and R 8 is represented by the formula (2).

21. The aromatic amine derivative according to claim 18 , wherein R 1 is represented by the formula (2), and any one of R 3 and R 8 is represented by the formula (2).

22. The aromatic amine derivative according to claim 21 , wherein X represents an oxygen atom.

23. The aromatic amine derivative according to claim 4 , wherein any one of R 1 and R 3 is represented by the formula (2).

24. The aromatic amine derivative according to claim 18 , wherein any one of R 1 and R 3 is represented by the formula (2).

25. The aromatic amine derivative according to claim 24 , wherein X represents an oxygen atom.

26. An organic electroluminescence device comprising:

a cathode;

an anode; and

an organic compound layer interposed between the cathode and the anode,

wherein the organic compound layer comprises the aromatic amine derivative according to claim 2 .