IP Library Granted Patent US 9,947,879
Granted Patent B2
US 9,947,879 · App. 14/650,488 · Granted Apr 17, 2018

Anthracene derivative and organic electroluminescence element using same

Inventors: Hirokatsu Ito (Sodegaura, JP); Hiroyuki Saito (Sodegaura, JP); Yumiko Mizuki (Sodegaura, JP); Masahiro Kawamura (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0073C07D307/77C07D307/91C07D307/92C07D405/10C09K11/06H01L51/0052H01L51/0058H01L51/0072H01L51/5012H05B33/20C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H01L51/5206H01L51/5221
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Quick Facts
Patent No.
US 9,947,879
App. No.
14/650,488
Granted
Apr 17, 2018
Kind
B2
Abstract

An anthracene derivative represented by the following formula (1): wherein in the formula (1), L 1 is selected from a single bond and a linking group, and the linking group is selected from a divalent arylene group, a divalent heterocyclic group, and a group formed by linking of 2 to 4 of divalent arylene groups and/or divalent heterocyclic groups. Ar 1 is selected from the following formulas (2) and (3). In the formulas (2) and (3), X is selected from an oxygen atom and a sulfur atom. In the formula (2), any one of R 11 to R 14 is used for bonding to L 1 . In the formula (3), any one of R 21 to R 24 is used for bonding to L 1 . Ar 2 is selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

Claims (51)

1. An anthracene derivative that is represented by any of the following formulas (4) to (7):

wherein in the formulas (4) to (7), R 1 to R 8 are independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms;

L 1 is selected from a single bond and a linking group, and the linking group is selected from a divalent arylene group and a divalent heterocyclic group;

X is selected from an oxygen atom and a sulfur atom;

R 11 to R 20 and R 21 to R 30 are the same as R 1 to R 8 ;

Ar 2 is selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms; and

adjacent groups of R 1 to R 8 , R 11 to R 20 , R 21 to R 30 , L 1 and Ar 2 may be bonded with each other to form a ring.

2. The anthracene derivative according to claim 1 , that is represented by any one of the following formulas (8) to (11):

wherein in the formulas (8) to (11), R 1 to R 8 , X, R 11 to R 20 , R 21 to R 30 and Ar 2 are as defined in the formulas (4) to (7).

3. The anthracene derivative according to claim 1 , that is represented by any of the following formulas (12) to (15):

wherein in the formulas (12) to (15), R 1 to R 8 , X, R 11 to R 20 , R 21 to R 30 and Ar 2 are as defined in the formulas (4) to (7).

4. The anthracene derivative according to claim 1 , wherein Ar 2 is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzanthryl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group and a substituted or unsubstituted dibenzofuranyl group.

5. The anthracene derivative according to claim 1 , wherein R 1 to R 8 are a hydrogen atom.

6. The anthracene derivative according to claim 1 , wherein R 11 to R 14 that are not used for bonding to L 1 and R 15 to R 20 , and R 21 to R 24 that are not used for bonding to L 1 and R 25 to R 30 are a hydrogen atom.

7. The anthracene derivative according to claim 1 , wherein X is an oxygen atom.

8. The anthracene derivative according to claim 1 , that is a material for an organic electroluminescence device.

9. The anthracene derivative according to claim 1 , that is an emitting material for an organic electroluminescence device.

10. An organic electroluminescence device comprising:

a cathode and an anode; and

one or more organic thin film layers including an emitting layer being disposed between the cathode and the anode;

wherein at least one of the organic thin film layers comprises the anthracene derivative according to claim 1 singly or as a mixture component.

11. The organic electroluminescence device according to claim 10 , wherein the emitting layer comprises the anthracene derivative.

12. The organic electroluminescence device according to claim 11 , wherein the anthracene derivative is a host material.

13. The organic electroluminescence device according to claim 11 , wherein the emitting layer further comprises a dopant material.

14. The organic electroluminescence device according to claim 13 , wherein the dopant material is an arylamine compound.

15. The organic electroluminescence device according to claim 13 , wherein the dopant material is a styrylamine compound.

16. The organic electroluminescence device according to claim 14 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (20):

wherein in the formula (20), Y is a substituted or unsubstituted fused aromatic hydrocarbon group including 10 to 50 ring carbon atoms;

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

n is an integer of 1 to 4.

17. The organic electroluminescence device according to claim 14 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (21):

wherein in the formula (21), R e is independently selected from a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl germanium group including 1 to 50 carbon atoms and a substituted or unsubstituted aryl germanium group including 6 to 50 ring carbon atoms; R e may be bonded to any of bonding positions of the four benzene rings of the fused polycyclic ring;

t is an integer of 0 to 10; and

Ar 201 to Ar 204 are independently selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

18. The organic electroluminescence device according to claim 14 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (22):

wherein in the formula (22), R f is independently selected from a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl germanium group including 1 to 50 carbon atoms, and a substituted or unsubstituted aryl germanium group including 6 to 50 ring carbon atoms; R f may be bonded to any of bonding positions of the four benzene rings of the fused polycyclic ring;

u is an integer of 0 to 8; and

Ar 205 to Ar 208 are independently selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

19. The organic electroluminescence device according to claim 14 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (23):

wherein in the formula (23), R g is independently selected from a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl germanium group including 1 to 50 carbon atoms and a substituted or unsubstituted aryl germanium group including 6 to 50 ring carbon atoms; R g may be bonded to any of bonding positions of the three benzene rings of the fused polycyclic ring;

m is an integer of 0 to 8; and

Ar 209 to Ar 212 are independently selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

20. The organic electroluminescence device according to claim 14 , wherein the dopant material is a fused polycyclic amine derivative represented by the following formula (24):

wherein in the formula (24), Ar 213 to Ar 218 are independently selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

21. An electronic appliance comprising the organic electroluminescence device according to claim 10 .

22. An anthracene derivative that is represented by any one of the following formulas (10′), (11′), (14′), and (15′):

wherein in the formulas (10′), (11′), (14′), and (15′), R 1 to R 8 and R 31 to R 42 are independently selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 30 ring atoms;

X is selected from an oxygen atom and a sulfur atom;

Ar 2 is selected from a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms; and

adjacent groups of R 1 to R 8 , R 31 to R 42 and Ar 2 may be bonded with each other to form a ring.

23. The anthracene derivative according to claim 16 , wherein Y in the formula (20) is a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group or a substituted or unsubstituted chrysenyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2015
From: ITO, HIROKATSU; SAITO, HIROYUKI; MIZUKI, YUMIKO; KAWAMURA, MASAHIRO
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 035804/0318 →
Priority Claims (2)
JP 2013-053591 · Mar 15, 2013 · national
JP 2013-084279 · Apr 12, 2013 · national
Continuity (1)
Related Publication 20150325800A1 · Nov 12, 2015