IP Library Granted Patent US 9,373,792
Granted Patent B2
US 9,373,792 · App. 14/817,765 · Granted Jun 21, 2016

Anthracene derivative and organic electroluminescent element using the same

Inventors: Masahiro Kawamura (Sodegaura, JP); Chishio Hosokawa (Sodegaura, JP); Masaki Numata (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0052C07D307/77C07D307/79C07D307/91C07D307/92C07D333/50C07D333/74C07D333/76C07D493/04C07D519/00C09K11/06H01L51/006H01L51/0058H01L51/0059H01L51/0072H01L51/0073H01L51/0074C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1088C09K2211/1092H01L51/0054H01L51/5012
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Quick Facts
Patent No.
US 9,373,792
App. No.
14/817,765
Granted
Jun 21, 2016
Kind
B2
Abstract

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):

Claims (46)

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.

Priority Claims (1)
JP 2009-131200 · May 29, 2009 · national
Continuity (4)
Continuation 14487768 · Sep 16, 2014
Continuation 14093325 · Nov 29, 2013
Continuation 13375020
Related Publication 20150372237A1 · Dec 24, 2015