Anthracene derivative and organic electroluminescent element using the same
An anthracene derivative represented by the following formula (1): In the formula (1), Z is a structure represented by the following formula (2). In the formula (2), at least one pair of adjacent two substituents of R 11 to R 18 form a ring represented by the following formula (3) or (4):
1. An anthracene derivative represented by the following formula (1):
wherein in the formula (1), at least one of R 1 to R 10 is used for bonding to L 1 , the one used for bonding to L 1 is a single bond, R 1 to R 10 which are not used for bonding to L 1 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L 1 is a single bond or a linkage group;
a, b and c are independently an integer of 1 to 4; and
Z is a structure represented by the following formula (2):
wherein in the formula (2), R 11 to R 18 are independently a hydrogen atom or a substituent and X 1 is an oxygen atom or a sulfur atom; and
at least one pair of adjacent two substituents of R 11 to R 18 form a ring represented by the following formula (3) or (4):
wherein in the formulas (3) and (4), R 21 to R 24 and R 31 to R 34 are independently a hydrogen atom or a substituent and X 2 is an oxygen atom or a sulfur atom;
any one of R 11 to R 18 which do not form a ring, R 21 to R 24 and R 31 to R 34 is used for bonding to L 1 , and the ones used for bonding to L 1 are a single bond.
2. The anthracene derivative according to claim 1 , wherein Z is represented by any of the following formulas (5) to (7):
wherein in the formulas (5) to (7), R 101 to R 110 , R 111 to R 120 and R 121 to R 130 are independently a hydrogen atom or a substituent; any one of R 101 to R 110 , any one of R 111 to R 120 , and any one of R 121 to R 130 are used for bonding to L 1 , the ones used for bonding to L 1 are a single bond; and
X 1 and X 2 are independently an oxygen atom or a sulfur atom.
3. The anthracene derivative according to claim 1 , wherein Z is represented by any of the following formulas (8) to (10):
wherein in the formulas (8) to (10), R 201 to R 210 , R 211 to R 220 and R 221 to R 230 are independently a hydrogen atom or a substituent; any one of R 201 to R 210 , any one of R 211 to R 220 and any one of R 221 to R 230 are used for bonding to L 1 ; and the ones used for bonding to L 1 are a single bond; and
X 1 is an oxygen atom or a sulfur atom.
4. The anthracene derivative according to claim 1 , wherein b is 1 in the formula (1).
5. The anthracene derivative according to claim 1 , wherein a is 1 or 2 in the formula (1).
6. The anthracene derivative according to claim 1 , wherein L 1 is bonded to R 5 and/or R 10 .
7. The anthracene derivative according to claim 1 , wherein L 1 is bonded to any of R 1 to R 4 .
8. The anthracene derivative according to claim 7 , wherein L 1 is bonded to R 2 .
9. The anthracene derivative according to claim 7 , wherein R 5 is a group selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
10. The anthracene derivative according to claim 7 , wherein R 5 and/or R 10 is a group selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
11. The anthracene derivative according to claim 10 , wherein R 5 has a structure represented by the following formula (11):
wherein in the formula (11), Ar 1 is a group selected from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; Ra is independently a hydrogen atom or a substituent; and d is an integer of 1 to 4.
12. The anthracene derivative according to claim 10 , wherein R 5 is a substituted or unsubstituted fused aromatic ring having 10 to 30 ring carbon atoms.
13. The anthracene derivative according to claim 1 , wherein X 1 and X 2 are oxygen atoms.
14. The anthracene derivative according to claim 1 , wherein L 1 is a single bond.
15. The anthracene derivative according to claim 1 , wherein L 1 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
16. The anthracene derivative according to claim 1 , which is a material for an organic electroluminescence device.
17. The anthracene derivative according to claim 1 , which is an emitting material for an organic electroluminescence device.
18. An organic electroluminescence device which comprises between an anode and a cathode one or more organic thin film layers comprising an emitting layer, wherein at least one layer of the organic thin film layers comprises the anthracene derivative according to claim 1 singly or as a mixture component.
19. The organic electroluminescence device according to claim 18 , wherein the emitting layer comprises the anthracene derivative.
20. The organic electroluminescence device according to claim 19 , wherein the anthracene derivative is a host material.
21. The organic electroluminescence device according to claim 19 , wherein the emitting layer further comprises a dopant material.
22. The organic electroluminescence device according to claim 21 , wherein the dopant material is an arylamine compound.
23. The organic electroluminescence device according to claim 21 , wherein the dopant material is a styrylamine compound.
24. The organic electroluminescence device according to claim 22 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (12):
wherein in the formula (12), Y is a substituted or unsubstituted fused aryl group having 10 to 50 ring carbon atoms; Ar 101 and Ar 102 are independently an aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and n is an integer of 1 to 4.
25. The organic electroluminescence device according to claim 24 , wherein the dopant material is a fused polycyclic amine derivative which is represented by the following formula (13):
wherein in the formula (13), R e is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms or a substituted or unsubstituted arylgermanium group having 6 to 50 ring carbon atoms; t is an integer of 1 to 10; and Ar 201 to Ar 204 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocylic group having 5 to 50 ring atoms.
26. The organic electroluminescence device according to claim 24 , wherein the dopant material is a fused polycyclic amine derivative which is represented by the following formula (14):
wherein in the formula (14), R f is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms or a substituted or unsubstituted arylgermanium group having 6 to 50 ring carbon atoms; u is an integer of 1 to 8; and Ar 205 to Ar 208 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocylic group having 5 to 50 ring atoms.
27. The organic electroluminescence device according to claim 24 , wherein the dopant material is a fused polycyclic amine derivative which is represented by the following formula (15):
wherein in the formula (15), R g is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms or a substituted or unsubstituted arylgermanium group having 6 to 50 ring carbon atoms; m is an integer of 1 to 10; and Ar 209 to Ar 212 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocylic group having 5 to 50 ring atoms.
28. The organic electroluminescence device according to claim 24 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (16):
wherein in the formula (16), Ar 213 to Ar 218 are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.