Aromatic amine derivative, organic electroluminescent element and electronic device

1. A compound represented by formula (1):

wherein in formula (1), Ar 1 represents an organic group A represented by the formula (A-1); Ar 2 represents the organic group A or an organic group B represented by formula (B-1); and Ar 3 represents the organic group B or an organic group C represented by formula (C-1),

provided that in the case where both Ar 1 and Ar 2 are the organic groups A, the organic groups A may be the same as or different from each other,

wherein in formula (A-1), R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms or an aryl group having from 6 to 12 ring carbon atoms, provided that R 1 and R 2 may be bonded to each other to form a hydrocarbon ring;

R 3 each independently represent a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms;

R 4 to R 6 each independently represent an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms; and

a, b. c and d each independently represent an integer of from 0 to 2,

provided that R 3 and R 4 may be bonded to each other to form a hydrocarbon ring; and in the case where a or b is 2, adjacent groups of R 3 or adjacent groups of R 4 may be bonded to each other to form a hydrocarbon ring,

wherein in formula (B-1), Ar 4 and Ar 5 each independently represent a phenylene group, a naphthyiene group, an anthrylene group or a phenanthrylene group; Ar 6 represents a phenyl group, a naphthyl group, an anthryl group or a phenanthryl group; R 7 to R 9 each independently represent an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms; e and g each independently represent an integer of from 0 to 2; f represents an integer of from 0 to 1; and h and i each independently represent 0 or 1,

provided that R 7 to R 9 may be bonded to each other to form a hydrocarbon ring; and in the case where e or g is 2, adjacent groups of R 7 or adjacent groups of R 9 may be bonded to each other to form a hydrocarbon ring,

wherein in formula (C-1), Ar 7 represents a substituted or unsubstituted aryl group having from 6 to 14 ring carbon atoms; R 10 represents an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms; and j represents an integer of from 0 to 2, provided. that in the case where j is 2, adjacent groups of R 10 may be bonded to each other to form a hydrocarbon ring.

2. The compound according to claim 1 , wherein in formula (A-1). R 1 and R 2 are not bonded to each other to form a hydrocarbon ring.

3. The compound according to claim 1 , wherein the organic group B is represented by formula (B-2):

4. The compound according to claim 1 , wherein the organic group B is represented by any one of formulae (B-3) to (B-5):

wherein Ar 6 represents a phenyl group, a naphthyl group, an anthryl group or a phenanthryl group; R 11 and R 12 each independently represent a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms; R 7 to R 9 each independently represent an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms; e and g each independently represent an integer of from 0 to 2: f represents an integer of from 0 to 1; and i represents 0 or 1,

provided that R 7 to R 9 may be bonded to each other to form a hydrocarbon ring; and in the case where e, f or g is 2, adjacent groups of R 7 or adjacent groups of R 9 may be bonded to each other to form a hydrocarbon ring.

5. The compound according to claim 1 , wherein Ar 2 represents the organic group B.

6. The compound according to claim 1 , wherein both Ar 1 and Ar 2 represent the organic groups A, and provided that Ar 1 and Ar 2 may be the same as or different from each other.

7. The compound according to claim 1 , wherein the compound is selected from H1 to H7:

8. A material for an organic electroluminescent device, comprising the compound according to claim 1 .

9. A hole transporting material for an organic electroluminescent device, comprising the compound according to claim 1 .

10. A hole transporting material for an organic electrolwninescent device having an acceptor layer-proximate hole transporting layer, comprising the compound according to claim 1 .

11. An organic electroluminescent device comprising a cathode and an anode, and intervening therebetween an organic thin film layer, and comprising at least one organic thin film layer containing the compound according to claim 1 .

12. An organic electroluminescent device comprising a cathode and an anode, and intervening therebetween at least two hole transporting layers and a light emitting layer sequentially, one of the hole transporting layer comprising the compound according to claim 1 and being not adjacent to the light emitting layer.

13. An organic electroluminescent device comprising a cathode and an anode, and intervening therebetween at least two hole transporting layers and a light emitting layer sequentially, and

wherein the hole transporting layers include a first hole transporting layer on the side of the anode and a second hole transporting layer on the side of the light emitting layer, the first hole transporting layer comprising the compound according to claim 1 .

14. The electroluminescent device according to claim 13 , wherein the second hole transporting layer comprises a compound represented by formula (4):

wherein in the formula (4), at least one of Ar 11 to Ar 13 represents a group represented by the formula (4-2) or (4-4); the group that is not represented by the general formula (4-2) is a group represented by formula (4-3) or (4-4) or a substituted or unsubstituted aryl group having from 6 to 40 ring carbon atoms; and the group that is not represented by the general formula (4-4) is a group represented by the following general formula (4-2) or (4-3) or a substituted or unsubstituted aryl group having from 6 to 40 ring carbon atoms,

wherein X 11 represents an oxygen atom or a sulfur atom;

L 1 to L 3 each independently represent a single bond or a substituted or unsubstituted arylene group having from 6 to 50 ring carbon atoms, and the substituent that may be substituted on L 1 to L 3 is a linear or branched alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms, a trialkylsilyl group having from 3 to 10 carbon atoms, a triatylsilyl group having from 18 to 30 ring carbon atoms, an alkylatylsilyl group having from 8 to 15 carbon atoms, an aryl group having from 6 to 50 ring carbon atoms, a halogen atom or a cyano group;

Ar 14 represents a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms, and the substituent that may be substituted on Ar 14 is a linear or branched alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms, a trialkylsilyl group having from 3 to 10 carbon atoms, a triarylsilyl group having from 18 to 30 ring carbon atoms, an alkylarylsilyl group having from 8 to 15 carbon atoms, an aryl group having from 6 to 50 ring carbon atoms, a halogen atom or a cyano group;

R 51 to R 56 each independently represent a substituted or unsubstituted and linear or branched alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 10 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having from 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having from 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having from 8 to 15 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms, a halogen atom or a cyano group, provided that the adjacent groups of R 51 to R 56 may be bonded to each other to form a ring;

b and f each independently represent an integer of from 0 to 3; and a, c, d and e each independently represent an integer of from 0 to 4.

15. The electroluminescent device according to claim 14 , wherein L 1 represents a substituted or unsubstituted arylene group having from 6 to 50 ring carbon atoms.

16. The electroluminescent device according to claim 14 , wherein L 3 represents a substituted or unsubstituted arylene group having from 6 to 50 ring carbon atoms.

17. The electroluminescent device according to claim 14 , wherein the aryl group having from 6 to 40 ring carbon atoms of Ar 11 to Ar 13 is represented by any one of formulae (4-5) to (4-7):

wherein R 61 R 64 each independently represent a linear or branched alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms, a trialkylsilyl group having from 3 to 10 carbon atoms, a triarylsilyl group having from 18 to 30 ring carbon atoms, an alkylaryisilyl group having from 8 to 15 carbon atoms, wherein the aryl moiety has from 6 to 14 ring carbon atoms, an aryl group having from 6 to 50 ring carbon atoms, a halogen atom or a cyano group, provided that the adjacent groups of R 61 to R 64 may be bonded to each other to form a ring; and

k, l, m and n each independently represent an integer of from 0 to 4.

18. The electroluminescent device according to claim 12 , further comprising an acceptor layer containing an acceptor material between the anode and the hole transporting layers.

19. The electroluminescent device according to claim 13 , wherein the first hole transporting layer contains an acceptor material.

20. The electroluminescent device according claim 18 , wherein the acceptor material is represented by formulae (A) to (C):

wherein in the formula (A), R 11 to R 16 each independently represent a cyano group, —CONH 2 , a carboxyl group or —COOR 17 and R 17 represents an alkyl group having from 1 to 20 carbon atoms, or represent a group represented by —CO—O—CO—by bonding R 11 and R 12 , and R 13 and R 14 , or R 15 and R 16 ,

wherein in formula (B), R 21 to R 24 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having from 5 to 50 ring atoms, a halogen atom, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 50 ring carbon atoms, or a cyano group, provided that R 21 and R 22 , and R 23 and R 24 may be bonded to each other to form a ring;

Y 1 to Y 4 each independently represent —N═, —CH═or C(R 25 )═, wherein R 25 represents a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having from 5 to 50 ring atoms, a halogen atom, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having from 6 to 50 ring carbon s, or a cyano group;

Ar 10 represents a condensed ring having from 6 to 24 ring carbon atoms or a heterocyclic ring having from 6 to 24 ring atoms; and ar 1 and ar 2 each independently represent a ring represented by the following general formula (i) or (ii):

wherein X 1 and X 2 each independently represent any one of the following divalent groups (a) to (g)

wherein R 31 to R 34 may be the same as or different from each other and each represent a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having from 5 to 50 ring atoms, provided that R 32 and R 33 may be bonded to each other to form a ring,

wherein Z 1 to Z 3 each independently represent a divalent group represented by formula (h):

wherein Ar 31 represents a substituted or unsubstituted aryl group having from 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having from 5 to 50 ring atoms.

21. The electrolwninescent device according to claim 12 , wherein the light emitting layer contains at least one fluorescent material selected from an anthracene derivative, a fluorantene derivative, a styrylamine derivative and an arylamine derivative.

22. The electroluminescent device according to claim 12 , wherein the light emitting layer contains a phosphorescent material.

23. The electroluminescent device according to claim 22 , wherein the phosphorescent material is an ortho-metallized complex of iridium (Ir), osmium (Os) or platinum (Pt).

24. The electroluminescent device according to claim 21 , wherein said device emits blue light.

25. The electroluminescent device according to claim 22 , wherein said device emits yellow light, green light or blue light.

26. An electronic apparatus comprising the organic electroluminescent device according to claim 11 .

27. The compound according to claim 1 , wherein in formula (B-1), e represents an integer of from 0 to 1.

28. The compound according to claim 1 , wherein in formula (B-1),R 7 to R 9 are not bonded to each other to form a hydrocarbon ring.

29. The compound according to claim 1 . wherein in formula (A-1), a represents an integer of 0.

30. The compound according to claim formula (C-1), Ar 7 represents a phenyl group, a naphthyl group, an anthryl group, or a phenanthryl group.

31. The compound according to claim 1 . wherein Ar 3 represents the organic group C represented by the formula (C-1).

32. The compound according to claim 1 , wherein:

in formula (A-1), a represents an integer of 0; and

in formula (B-1), e represents an integer of from 0 to 1, and R 7 to R 9 are not bonded to each other to form a hydrocarbon ring.

33. The compound according to claim 1 , wherein:

in formula (A-1), a represents an integer of 0;

Ar 2 represents the organic group B.

in formula (B-1), e represents an integer of from 0 to 1, and R 7 to R 9 are not bonded to each other to form a hydrocarbon ring;

Ar 3 represents the organic group C represented by the formula (C-1); and

in formula (C-1), Ar 7 represents a phenyl group, a naphthyl group, an anthryl group, or a phenanthryl group.

34. The compound according to claim 1 , wherein:

Ar 2 represents formula (B-1), and R 7 to R 9 are not bonded to each other to form a hydrocarbon ring;

Ar 3 represents formula (C-1); and

in formula (C-1), Ar 7 represents a phenyl group, a naphthyl group, an anthryl group, or a phenanthryl group.

35. The compound according to claim 1 , wherein:

Ar 2 is represented by any one of following formulae;

 wherein R 7 , R 9 , e, and g are the same as in claim 1 ,

Ar 3 represents formula (C-1); and

in formula (C-1), Ar 7 represents a phenyl group, a naphthyl group, an anthryl group, or a phenanthryl group.

36. The compound according to claim 1 , wherein:

Ar 2 is represented by any one of formulae (B3) to (B-5):

 wherein

Ar 6 represents a phenyl group, a naphthyl group, an anthryl group or a phenanthryl group;

R 11 and R 12 each independently represent a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms;

R 7 to R 9 each independently represent an alkyl group having from 1 to 10 carbon atoms, a cycloalkyl group having from 3 to 10 ring carbon atoms or an aryl group having from 6 to 12 ring carbon atoms;

e and g each independently represent an integer of from 0 to 2;

f represents an integer of from 0 to 1; and

i represents 0 or 1,

Ar 3 represents formula (C-1); and

in formula (C-1), Ar 7 represents a phenyl group, a naphthyl group, an anthryl group, or a phenanthryl group.