IP Library Granted Patent US 8,866,135
Granted Patent B2
US 8,866,135 · App. 14/093,325 · Granted Oct 21, 2014

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.
H01L51/0052C07D307/79C07D333/50H01L51/0058C09K11/06H01L51/0074H01L51/5012C07D307/92C07D307/77H01L51/006C07D333/74C07D519/00C09K2211/1011C07D307/91C07D493/04H01L51/0073C09K2211/1014C07D333/76
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Quick Facts
Patent No.
US 8,866,135
App. No.
14/093,325
Granted
Oct 21, 2014
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 (49)

1. An anthracene derivative of formula (1):

wherein at least one of R 1 to R 10 bonds, by a single bond, to L 1 , and R 1 to R 10 not 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 comprising 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group comprising 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group comprising 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms;

L 1 is a single bond or a linkage group, the linkage is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, if the linkage group has 3 or more valences, L 1 is a group having 3 or more valences corresponding to the above-mentioned divalent linkage group represented by L 1 ;

a, b, and c are independently an integer of 1 to 4; and

Z is a structure represented by the following formula (7):

wherein in the formula (7), R 121 to R 130 are independently a hydrogen atom or a substituent; any one of R 121 to R 130 bonds, by a single bond, to L 1 ; and

X 1 and X 2 are independently an oxygen atom or a sulfur atom.

2. The anthracene derivative of claim 1 , wherein, in formula (1), b is 1.

3. The anthracene derivative of claim 1 , wherein, in formula (1), a is 1 or 2.

4. The anthracene derivative of claim 1 , wherein L 1 is bonded to R 5 , R 10 , or both.

5. The anthracene derivative of claim 1 , wherein L 1 is bonded to any of R 1 to R 4 .

6. The anthracene derivative of claim 5 , wherein L 1 is bonded to R 2.

7. The anthracene derivative of claim 5 , wherein R 5 is selected from the group consisting of a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms.

8. The anthracene derivative of claim 5 , wherein at least one selected from the group consisting of R 5 and R 10 is selected from the group consisting of a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

9. The anthracene derivative of claim 7 , wherein R 5 has a structure of formula (11):

wherein Ar 1 is selected from the group consisting of a substituted or unsubstituted aryl group comprising 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group comprising 5 to 30 ring atoms; Ra is independently a hydrogen atom or a substituent; and d is an integer of 1 to 4.

10. The anthracene derivative of claim 7 , wherein R 5 is a substituted or unsubstituted fused aromatic ring comprising 10 to 30 ring carbon atoms.

11. The anthracene derivative of claim 1 , wherein X 1 and X 2 are oxygen atoms.

12. The anthracene derivative of claim 1 , wherein the anthracene derivative is suitable for use as a material for an organic electroluminescence device.

13. The anthracene derivative of claim 1 , where the anthracene derivative is employed as an emitting material in an organic electroluminescence device.

14. An organic electroluminescence device, comprising:

an anode;

a cathode; and

an organic thin film layer comprising an emitting layer,

wherein the organic thin film layer is between the cathode and the anode,

wherein a layer of the organic thin film layer comprises the anthracene derivative of claim 1 .

15. The device of claim 14 , wherein the emitting layer comprises the anthracene derivative.

16. The device of claim 15 , wherein the anthracene derivative is a host material.

17. The device of claim 15 , wherein the emitting layer comprises a dopant material.

18. The device of claim 17 , wherein the dopant material is an arylamine compound.

19. The device of claim 17 , wherein the dopant material is a styrylamine compound.

20. The device of claim 18 , wherein the dopant material is a fused polycyclic amine derivative of formula (12):

wherein Y is a substituted or unsubstituted fused aryl group comprising 10 to 50 ring carbon atoms;

Ar 101 and Ar 102 are independently an aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms; and

n is an integer of 1 to 4.

21. The device of claim 20 , wherein the dopant material is a fused polycyclic amine derivative of formula (13):

wherein R e is independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group comprising 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group comprising 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 comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms.

22. The device of claim 20 , wherein the dopant material is a fused polycyclic amine derivative of formula (14):

wherein R f is independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group comprising 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group comprising 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 comprising 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 comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms.

23. The device of claim 20 , wherein the dopant material is a fused polycyclic amine derivative of formula (15):

wherein R g is independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group comprising 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group comprising 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group comprising 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylgermanium group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group comprising 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 comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms.

24. The device of claim 20 , wherein the dopant material is a fused polycyclic amine derivative of formula (16):

wherein Ar 213 to Ar 218 are independently a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group comprising 5 to 50 ring atoms.

Priority Claims (1)
JP 2009-131200 · May 29, 2009 · national
Continuity (2)
Continuation 13375020
Related Publication 20140159005A1 · Jun 12, 2014