Aromatic amine derivative and organic electroluminescent element
An organic electroluminescence device having a long lifetime and a higher emission efficiency and a specific aromatic amine derivative which provides such an organic electroluminescence device are provided. In the specific aromatic amine derivative, a dibenzofuranyl group or a dibenzothiophenyl group is bonded via a p-phenylene and a heteroaryl group is bonded via a m-phenylene. The organic electroluminescence device includes a cathode, an anode and an organic thin film layer including one or more layers which is disposed between the cathode and the anode. The organic thin film layer includes at least one light emitting layer and at least one layer of the organic thin film layer includes the aromatic amine derivative singly or in combination.
1. An aromatic amine derivative represented by formula (1):
wherein:
R 1 represents a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;
each R 2 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a halogen atom, or a substituted carbonyl group, and when k is 2 or more, the groups R 2 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring;
each of R 3 and R 4 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a halogen atom, or a substituted carbonyl group, when p is 2 or more, the groups R 3 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring, and when q is 2 or more, the groups R 4 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring;
X represents an oxygen atom or a sulfur atom;
k represents an integer of 0 to 5;
m represents an integer of 1 to 2;
n represents an integer of 1 to 2;
p represents an integer of 0 to 3; and
q represents an integer of 0 to 4.
2. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is represented by formula (2):
wherein R 1 , R 2 , R 3 , R 4 , X, k, m, n, p, and q are as defined above.
3. The aromatic amine derivative according to claim 2 , wherein the aromatic amine derivative is represented by formula (3):
wherein R 1 , R 2 , R 3 , R 4 , X, k, p, and q are as defined above.
4. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is represented by formula (4):
wherein R 1 , R 2 , R 3 , R 4 , X, k, m, n, p, and q are as defined above.
5. The aromatic amine derivative according to claim 4 , wherein the aromatic amine derivative is represented by formula (5):
wherein R 1 , R 2 , R 3 , R 4 , X, k, p, and q are as defined above.
6. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is represented by formula (6):
wherein R 1 , R 2 , R 3 , R 4 , X, m, n, p, and q are as defined above.
7. The aromatic amine derivative according to claim 3 , wherein the aromatic amine derivative is represented by formula (7):
wherein:
R 2 , R 3 , R 4 , X, k, p, and q are as defined above;
each of R 5 and R 6 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a halogen atom, or a substituted carbonyl group, when r is 2 or more, the groups R 5 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring, and when s is 2 or more, the groups R 6 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring;
r represents an integer of 0 to 4; and
s represents an integer of 0 to 3.
8. The aromatic amine derivative according to claim 5 , wherein the aromatic amine derivative is represented by formula (8):
wherein R 2 , R 3 , R 4 , R 5 , R 6 , X, k, p, q, r, and s are as defined above.
9. The aromatic amine derivative according to claim 1 , wherein R 1 in formulae (1) to (6) is represented by any one of formulae (11-1) to (11-4):
wherein:
each of R 5 , R 5 ′ and R 6 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a halogen atom, or a substituted carbonyl group;
when each of r1 to r5 is 2 or more, the groups R 5 or the groups R 5 ′ on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring, and when each of s1 to s3 is 2 or more, the groups R 6 on adjacent ring carbon atoms may be bonded to each other to form a hydrocarbon ring;
R 7 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms;
each of r1 to r5 independently represents an integer of 0 to 4; and
each of s1 to s3 independently represents an integer of 0 to 3.
10. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is a material for an organic electroluminescence device.
11. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is a hole injecting material or a hole transporting material for an organic electroluminescence device.
12. An organic electroluminescence device which comprises a cathode, an anode, and an organic thin film layer comprising one or more layers between the cathode and the anode, wherein the organic thin film layer comprises a light emitting layer, and at least one layer of the organic thin film layer comprises the aromatic amine derivative according to claim 1 singly or in combination.
13. The organic electroluminescence device according to claim 12 , wherein the organic thin film layer comprises a hole transporting layer and the hole transporting layer comprises the aromatic amine derivative.