Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element

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

where: R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and 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 trifluoroalkyl group having 1 to 20 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 a proviso that, in the formula (1), R 1 and R 6 are represented by a formula (2) below,

where: 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 residue derived from a ring structure represented by a formula (4) below,

where: X represents an oxygen atom or a sulfur atom,

R 11 to R 17 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 trifluoroalkyl group having 1 to 20 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;

R 18 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; with a proviso that, when at least one of R 11 to R 18 is an unsubstituted methyl group, R 11 , R 12 , R 14 , R 15 , R 17 or R 18 is the unsubstituted methyl group;

one of R 11 to R 17 is a single bond to be bonded with L 1 ;

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 , and R 16 and R 17 optionally forms a saturated or unsaturated ring;

in the formula (2), 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 residue derived from the ring structure represented by the formula (4H)

wherein X represents an oxygen atom or a sulfur atom,

R 21 to R 28 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 trifluoroalkyl group having 1 to 20 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;

at least one of R 21 to R 28 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; with a proviso that, when at least one of R 21 to R 28 is an unsubstituted methyl group, R 21 , R 22 , R 24 , R 25 , R 27 or R 28 is the unsubstituted methyl group;

one of R 21 to R 28 is a single bond to be bonded with L 2 ;

at least one combination of R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 optionally forms a saturated or unsaturated ring.

2. The aromatic amine derivative according to claim 1 , wherein R 11 in Ar 1 is bonded to L 1 by a single bond.

3. The aromatic amine derivative according to claim 1 , wherein Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

4. The aromatic amine derivative according to claim 1 , wherein each of L 1 , L 2 and L 3 in the formula (2) is a single bond.

5. An organic-EL-device material comprising: the aromatic amine derivative according to claim 1 .

6. An organic electroluminescence device comprising a cathode, an organic compound layer and an anode in this order, wherein the organic compound layer comprises the aromatic amine derivative according to claim 1 .

7. The organic electroluminescence device according to claim 6 , wherein the organic compound layer comprises a plurality of organic thin-film layers including an emitting layer, and at least one of the plurality of organic thin-film layers comprises the aromatic amine derivative.

8. The organic electroluminescence device according to claim 7 , 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) below,

where: 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:

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.

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

10. The organic electroluminescence device according to claim 8 , 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.

11. The organic electroluminescence device according to claim 10 , wherein in the formula (20), Ar 12 is selected from a naphthyl group, phenanthryl group, benzanthryl group and dibenzofuranyl group, and Ar 11 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted fluorenyl group.

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

13. The organic electroluminescence device according to claim 8 , wherein Ar 11 and Ar 12 in the formula (20) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.

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

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

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

17. The aromatic amine derivative according to claim 1 , wherein in the formula (4) for Ar 1 , one of R 11 to R 17 is bonded to L 1 , at least another one of R 11 to R 17 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the rest of R 11 to R 17 each are a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

18. The aromatic amine derivative according to claim 1 , wherein in the formula (4) for Ar 1 , one of R 11 to R 17 is bonded to L 1 , and the rest of R 11 to R 17 each are a hydrogen atom.

19. The aromatic amine derivative according to claim 1 , wherein in the formula (4) for Ar 1 , combinations of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , and R 16 and R 17 do not form a saturated or unsaturated ring.

20. The aromatic amine derivative according to claim 1 , wherein Ar 2 is a substituted or unsubstituted phenyl group.

21. The aromatic amine derivative according to claim 1 , wherein Ar 2 is a phenyl group substituted by an alkyl group having 1 to 30 carbon atoms.

22. The aromatic amine derivative according to claim 1 , wherein R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the formula (1) are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

23. The aromatic amine derivative according to claim 1 , wherein R 3 and R 8 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and R 2 , R 4 , R 5 , R 7 , R 9 and R 10 are each independently a hydrogen atom.

24. The aromatic amine derivative according to claim 1 , wherein X is an oxygen atom.

25. The aromatic amine derivative according to claim 1 , wherein R 18 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.