Aromatic amine derivative and organic electroluminescent element
Provided are a long-lifetime organic electroluminescence device which can be fabricated in an improved yield owing to suppressed crystallization of molecules, and an aromatic amine derivative that realizes the device, i.e., a novel aromatic amine derivative having a specific structure. Specifically provided are an organic electroluminescence device, including an organic thin film layer formed of one or more layers including at least a light emitting layer, the organic thin film layer being interposed between a cathode and an anode, and an aromatic amine derivative for at least one layer of the organic thin film layer, in particular, a hole transporting layer, the derivative having at least one such structure that a substituent in which two or more specific heterocycles are linked to each other, in particular, a substituent in which two or more specific heterocycles are linked through an aryl group is bonded to an amine through an aryl group.
1. An aromatic amine derivative represented by any one of formulae (13) to (17):
wherein Ar 3 to Ar 26 are substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms except that at least one of Ar 3 to Ar 5 , at least one of Ar 6 to Ar 9 , at least one of Ar 10 to Ar 14 , at least one of Ar 15 to Ar 20 , and at least one of Ar 21 to Ar 26 are each represented by formula (1) below, and
L 3 to L 11 each represent the same linking group as the linking group represented by L 2 in formula (1) below:
wherein
(i) L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
(ii) L 2 represents a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
provided that an arbitrary substituent for each of L 1 and L 2 comprises a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 30 carbon atoms, a triarylsilyl group whose aryl groups each have 6 to 10 ring carbon atoms, an alkylarylsilyl group having 8 to 24 carbon atoms whose aryl portion has 6 to 14 ring carbon atoms, an unsubstituted aryl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group, and a plurality of substituents are identical to or different from each other,
(iii) A represents a linking group represented by any one of formulae (2) to (4):
wherein
R 1 to R 6 each independently represent the same substituent as the arbitrary substituent for each of L 1 and L 2 , or a formula -L 2 -B, wherein B has the same meaning as meaning of B to be described below, and
a plurality of R 1 's, R 2 's, R 3 's, R 4 's, R 5 's or R 6 's adjacent to each other are optionally bonded to each other to form a saturated or unsaturated ring,
d represents an integer of 0 to 4,
a, b, c, e, and f each independently represent an integer of 0 to 3,
and
Ar 1 represents a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms,
provided that substituents for Ar 1 each independently comprise the same substituent as the arbitrary substituent for each of L 1 and L 2 , and
(iv) B represents a substituent represented by any one of formulae (6) and (8):
wherein
R 8 , R 9 , R 12 and R 13 each independently represent the same substituent as the arbitrary substituent for each of L 1 and L 2 , or a formula -L 2 -B, and
a plurality of R 8 's, R 9 's, R 12 's or R 13 's adjacent to each other are optionally bonded to each other to form a saturated or unsaturated ring,
i, j, k, and m each independently represent an integer of 0 to 4,
h, l, and n each independently represent an integer of 0 to 3, and
Ar 2 represents a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms,
provided that substituents for Ar 2 each independently comprise any one of the same substituent as the arbitrary substituent for each of L 1 and L 2 except an aryl group, and a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group.
2. The derivative of claim 1 , wherein A represents a linking group represented by any one of formulae (2) to (4), and B represents a substituent represented by any one of formulae (6) and (8).
3. The derivative of claim 1 , wherein L 1 represents a linking group represented by any one of formulae (10) to (12):
wherein
R 15 to R 19 each independently represent the same substituent as the arbitrary substituent for each of L 1 and L 2 ,
R 20 and R 21 each independently represent a linear or branched alkyl group formed of a hydrocarbon having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 ring carbon atoms,
a plurality of R 15 's, R 16 's, R 17 's, R 18 's, or R 19 's adjacent to each other are optionally bonded to each other to form a saturated or unsaturated ring;
o, p, and q each independently represent an integer of 0 to 4, and
r and s each independently represent an integer of 0 to 3, and
L 2 represents a single bond, or a linking group represented by any one of formulae (10) to (12).
4. The derivative of claim 3 , wherein
L 1 represents a linking group represented by any one of formulae (10) to (12), and L 2 represents a single bond.
5. The derivative of claim 1 , wherein
L 1 is at least one selected from the group consisting of a phenylene group, a biphenylene group, and a 9,9-dimethylfluorenylene group, and
L 2 represents a single bond.
6. The derivative of claim 1 , wherein A represents a linking group of formula (2).
7. The derivative of claim 1 , wherein A represents a linking group of formula (3).
8. The derivative of claim 1 , wherein A represents a linking group of formula (4).
9. The derivative of claim 1 , wherein B represents a substituent of formula (6).
10. The derivative of claim 1 , wherein B represents a substituent of formula (8).
11. The derivative of claim 1 , wherein the aromatic amine derivative is of formula (13).
12. The derivative of claim 11 , wherein at least one selected from the group consisting of Ar 3 , Ar 4 , and Ar 5 is of formula (1), and the others each represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
13. The derivative of claim 1 , wherein the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms comprises at least one selected from the group consisting of a naphthyl group, a biphenyl group, and a terphenyl group.
14. A material, comprising the derivative of claim 1 , wherein the material is suitable for an organic electroluminescence device.
15. A hole transporting material, comprising the derivative of claim 1 , which is suitable for an organic electroluminescence device.
16. An organic electroluminescence device, comprising an organic thin film layer comprising one or more layers comprising a light emitting layer,
wherein the organic thin film layer is interposed between a cathode and an anode,
wherein at least one layer of the organic thin film layer comprises the derivative of claim 1 .
17. The device of claim 16 , wherein the organic thin film layer comprises at least one member selected from the group consisting of a hole transporting layer and a hole injecting layer, and
the derivative of claim 1 is incorporated into the at least one member.
18. The device of claim 17 , wherein the organic thin film layer comprises a hole transporting zone comprising at least one selected from the group consisting of a hole transporting layer and a hole injecting layer, and
the derivative of claim 1 is incorporated into a layer out of direct contact with the light emitting layer in the hole transporting zone.
19. The device of claim 17 , wherein the derivative of claim 1 is incorporated as a main component into the at least one member.
20. The device of claim 16 , wherein the light emitting layer comprises at least one selected from the group consisting of a styrylamine compound and an arylamine compound.
21. The device of claim 16 , wherein a layer in contact with the anode out of layers comprised in at least one selected from the group consisting of a hole injecting layer and a hole transporting layer, comprises a layer comprising an acceptor material.
22. The device of claim 16 , which emits blue light.
23. A compound of the formula H4: