Novel anthracene derivative and organic electronic device using the same

Abstract

The present invention provides a novel anthracene derivative and an organic electronic device using the same. The organic electronic device according to the present invention shows excellent characteristics in efficiency, drive voltage, and life time.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates one example of the organic light emitting device according to the present invention.

FIG. 2 illustrates the UV data of the compound according to the present invention synthesized in Preparative Examples 9 and 10.

FIG. 3 illustrates the UV data of the compound according to the present invention synthesized in Preparative Example 11.

Claims

1. A compound represented by the following formula 1:

2. The compound according to claim 1, wherein R1 and R2 of formula 1 are the same aryl groups.

3. The compound according to claim 1, wherein R1 and R2 of formula 1 are the same heteroaryl groups.

4. The compound according to claim 1, wherein R1 and R2 of formula 1 are the amino groups substituted with the same aryl groups or the same heteroaryl groups.

5. The compound according to claim 1, wherein R1 and R2 of formula 1 are selected from the group consisting of the following structural formulae:

6. The compound according to claim 1, wherein at least one of R5 and R6 of the formula 2 is hydrogen.

7. The compound according to claim 1, wherein Ar1 of the formula 2 is selected from the group consisting of the following structural formulae:

8. The compound according to claim 1, wherein the alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, a hexyl group, and a heptyl group; the cycloalkyl group is a cyclopentyl group or a cyclohexyl group; the alkenyl group is a stilbenyl group or a styrenyl group; the aryl group is selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group, a pyrenyl group, and a perylene group; the aryl amine group is selected from the group consisting of a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methyl-phenylamine group, a 4-methyl-naphthylamine group, a 2-methyl-biphenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group, and a triphenylamine group; the heterocyclic group is selected from the group consisting of a pyridyl group, a bipyridyl group, a triazine group, an acridyl group, a thiophene group, a puran group, an imidazole group, an oxazole group, a thiazole group, a triazole group, a quinolidyl group, and an isoquinoline group; and the halogen is selected from the group consisting of a fluorine, a chlorine, a bromine, and a iodine.

9. The compound according to claim 1, wherein the C2 to C40 alkenylene group is substituted with at least one selected from the group consisting of a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C1 to C40 alkoxy group, a C6 to C40 aryl group, and a C3 to C40 heteroaryl group.

10. The compound according to claim 1, wherein the compound of the formula 1 is selected from the compounds of the following formulae 1-1 to 1-223:

11. A method for preparing a compound according to claim 1, comprising the steps of: 1) preparing a R4-substituted anthraquinone derivative by subjecting a halogen-substituted anthraquinone derivative and a boronic acid or boronic ester compound having a R4 substituent to Suzuki coupling in the presence of a Pd catalyst,2) preparing a dialcohol derivative from the anthraquinone derivative prepared in the step 1), and3) preparing an anthracene derivative by reducing the dialcohol derivative prepared in the step 2).

12. A method for preparing a compound according to claim 1, comprising the steps of: 1) preparing an anthraquinone derivative by introducing an arylamino group to a halogen-substituted anthraquinone derivative in the presence of a Pd catalyst,2) preparing a dialcohol derivative from the anthraquinone derivative prepared in the step 1), and3) preparing an anthracene derivative by reducing the dialcohol derivative prepared in the step 2).

13. A method for preparing a compound according to claim 1, comprising the steps of: 1) preparing a dialcohol derivative from a halogen-substituted anthraquinone derivative,2) preparing an anthracene derivative by reducing the dialcohol derivative prepared in the step 1),3) preparing an anthracene boronic ester derivative from an anthracene derivative prepared in the step 2), and4) preparing a R4-substituted compound of the formula 1 by subjecting the anthracene boronic ester derivative prepared in the step 3) and a halide of R4 to Suzuki coupling in the presence of a Pd catalyst.

14. An organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer interposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to claim 1.

15. The organic electronic device according to claim 14, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor.

16. The organic electronic device according to claim 14, wherein the organic electronic device is an organic light emitting device.

17. The organic electronic device according to claim 16, wherein the organic light emitting device has a forward structure in which an anode, at least one organic material layer, and a cathode are sequentially laminated on a substrate.

18. The organic electronic device according to claim 16, wherein the organic light emitting device has a reverse structure in which a cathode, at least one organic material layer, and an anode are sequentially laminated on a substrate.

19. The organic electronic device according to claim 16, wherein the organic material layer of the organic light emitting device comprises a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron injecting and transporting layer.

20. The organic electronic device according to claim 16, wherein the organic material layer of the organic light emitting device comprises a light emitting layer, and the light emitting layer comprises the compound according to claim 1.

21. The organic electronic device according to claim 16, wherein the organic material layer of the organic light emitting device comprises an electron transporting and/or injecting layer, and this layer comprises the compound according to claim 1.