IP Library Granted Patent US 8,629,430
Granted Patent B2
US 8,629,430 · App. 13/375,020 · Granted Jan 14, 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.
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Quick Facts
Patent No.
US 8,629,430
App. No.
13/375,020
Granted
Jan 14, 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 (53)

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 un substituted 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 formula (5), (6), (8), (9) or (10

wherein in the formulas (5) and (6), R 101 to R 110 and R 111 to R 120 are independently a hydrogen atom or a substituent; any one of R 101 to R 110 , and any one of R 111 to R 120 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;

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 228 are used for bonding to L 1 ; and the ones used for bonding to L 1 are a single bond;

R 229 and R 230 are a hydrogen atom; and

X 1 is 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 6to 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2012
From: KAWAMURA, MASAHIRO; HOSOKAWA, CHISHIO; NUMATA, MASAKI
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 027735/0194 →
Priority Claims (1)
JP 2009-131200 · May 29, 2009 · national
Continuity (1)
Related Publication 20120138914A1 · Jun 7, 2012