Arylene derivative and organic light emitting device manufactured using the same

Abstract

Provided is an arylene derivative including a polar functional group represented by Formula 1:

Description

BRIEF DESCRIPTION OF THE DRAWINGS

A more complete appreciation of the invention, and many of the attendant advantages thereof, will be readily apparent as the same becomes better understood by reference to the following detailed description when considered in conjunction with the accompanying drawings in which like reference symbols indicate the same or similar components, wherein:

FIGS. 1A through 1C are sectional views schematically illustrating structures of organic light emitting devices according to embodiments of the present invention;

FIG. 2 is a graph of the absorption spectra and photoluminescence of a compound 2 according to an embodiment of the present invention;

FIG. 3 is a graph illustrating the experimental result of a thermogravimetric analysis (TGA) for a compound 2 according to an embodiment of the present invention; and

FIG. 4 is a graph illustrating results of an infrared experiment performed on a compound 2 according to an embodiment of the present invention before and after heat treatment.

Claims

1. An arylene derivative represented by Formula 1:

2. The arylene derivative of claim 1, wherein the compound represented by Formula 1 is the compound represented by Formula 1a:

3. The arylene derivative of claim 1, wherein the compound represented by Formula 1 is a compound represented by Formula 1b:

4. The arylene derivative of claim 1, wherein Ar1, Ar2, Ar3, and Ar4 are each independently, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazoyl group, a substituted or unsubstituted thiophene group, or a substituted or unsubstituted thiazole group; N1 and N2 are each independently, hydrogen, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;M1 and M2 are each independently, hydrogen,

5. The arylene derivative of claim 1, wherein the substituents of the alkyl group, the aryl group, the heteroaryl group, and the cycloalkyl group are at least one selected from the group consisting of —F, —Cl, —Br, —CN, —NO2 or —OH; a C1-C20 alkyl group unsubstituted or substituted for —F, —Cl, —Br, —CN, —NO2, or —OH; a C1-C20 alkoxy group unsubstituted or substituted for —F, —Cl, —Br, —CN, —NO2, or —OH; a C6-C30 aryl group unsubstituted or substituted for —F, —Cl, —Br, —CN, —NO2, or —OH; a C2-C30 heteroaryl group unsubstituted or substituted for —F, —Cl, —Br, —CN, —NO2, or —OH; and a C5-C20cycloalkyl group unsubstituted or substituted for —F, —Cl, —Br, —CN, —NO2, or —OH.

6. The arylene derivative of claim 1, wherein Ar1, Ar2, Ar3, and Ar4 are each independently selected from the group consisting of phenylene group, C1-C10 dicyanophenylene group, trifluoromethoxyphenylene group, o-, m-, or p-tolylene group, o-, m-, or p-cumenylene group, mesitylene group, phenoxyphenylene group, (α,α-dimethylbenzene)phenylene group, (N,N′-dimethyl)aminophenylene group, (N,N′-diphenyl)aminophenylene group, (C1-C10alkylcyclohexyl)phenylene group, (anthryl)phenylene group, biphenylene group, C1-C10alkylbiphenylene group, C1-C10 alkoxybiphenylene group, pentalenyl group, indenylene group, naphthylene group, C1-C10 alkylnaphthylene group, C1-C10 alkoxynaphthylene group, halonaphthylene group, cyanonaphthylene group, biphenylenylene group, C1-C10 alkyl biphenylenylene group, C1-C10 alkoxy biphenylenylene group, anthrylene group, biphenylanthrylene group, azulenylene group, heptalenylene group, acenaphthylenylene group, phenalenylene group, fluorenylene group, anthraquinolylene group, methylanthrylene group, phenanthrylene group, triphenylenylenealkylphenylene group, C1-C10 alkoxyphenylene group, halophenylene group, cyanophenylene group, pyrenylene group, chrysenylene group, ethyl- chrysenylene group, picenylene group, perylenylene group, chloroperylenylene group, pentaphenylene group, pentacenyl group, tetraphenylenyl group, hexaphenylene group, hexacenylene group, rubicenylene group, coronenylene group, trinaphthylenylene group, heptaphenylene group, heptacenylene group, pyranthrenylene group, ovalenylene group, carbazolylene group, C1-10 alkyl carbazolylene group, thienylene group, indolylene group, purinylene group, benzimidazolylene group, quinolinylene group, benzothiophenylene group, parathiazinylene group, pyrrolylene group, pyrazolylene group, imidazolylene group, imidazolinylene group, oxazolylene group, thiazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, pyridinylene group, pyridazinylene group, pyrimidinylene group, pyrazinylene group, thianthrenylene group, pyrrolidinylene group, pyrazolidinylene group, imidazolidinylene group, piperidinylene group, piperazinylene group, and morpholinylene group.

7. The arylene derivative of claim 1, wherein L1, L2, and L3 are each independently selected from the group consisting of phenyl group, C1-C10 alkylphenyl group, C1-C10 alkoxyphenyl group, halophenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o-, m-, or p-tolyl group, o-, m- or p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene)phenyl group, (N,N′-dimethyl)aminophenyl group, (N,N′-diphenyl)aminophenyl group, (N,N′-bis)methylphenyl))aminophenyl group, (N,N′-dinaphthyl)aminophenyl group, (C1-C10 alkylcyclohexyl)phenyl group, (anthryl)phenyl group, biphenyl group, C1-C10 alkylbiphenyl group, C1-C10alkoxybiphenyl group, pentalenyl group, indenyl group, naphthyl group, C1-C10 alkylnaphthyl group, C1-C10 alkoxynaphthyl group, halonaphthyl group, cyanonaphthyl group, biphenylenyl group, C1-C10 alkyl biphenylenyl group, C1-C10 alkoxy biphenylenyl group, anthracenyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthraquinolyl group, methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptacenyl group, pyranthrenyl group, ovalenyl group, carbazolyl group, C1-10alkyl carbazolyl group, thienyl group, indolyl group, purinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group, piperidinyl group, piperazinyl group, carbazolyl group, benzoxazolyl group, phenothiazinyl group, 5H-dibenzoazepinyl group, 5H-tribenzoazepinyl group, and morpholinyl group.

8. The arylene derivative of claim 1, wherein L4 is selected from the group consisting of hydrogen, methyl group, ethyl group, propyl group, butyl group, methoxy group, ethoxy group, propoxy group, butoxy group, C1-C10alkylamine group, C1-C10 thioalkyl group, phenyl group, C1-C10alkylphenyl group, C1-C10alkoxyphenyl group, halophenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o-, m-, or p-tolyl group, o-, m-, or p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene)phenyl group, (N,N′-dimethyl)aminophenyl group, (N,N′-diphenyl)aminophenyl group, (C1-C10 alkylcyclohexyl)phenyl group, (anthryl)phenyl group, biphenyl group, C1-C10 alkylbiphenyl group, C1-C10 alkoxybiphenyl group, pentalenyl group, indenyl group, naphthyl group, C1-C10 alkylnaphthyl group, C1-C10 alkoxynaphthyl group, halonaphthyl group, cyanonaphthyl group, biphenylenyl group, C1-C10 alkyl biphenylenyl group, C1-C10 alkoxy biphenylenyl group, anthracenyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthraquinolyl group, methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptacenyl group, pyranthrenyl group, ovalenyl group, carbazolyl group, cyclopentyl group, cyclohexyl group, C1-C10 alkylcyclohexyl, and C1-C10alkoxycyclohexyl group.

9. The arylene derivative of claim 1, wherein N1 and N2 are each independently selected from the group consisting of hydrogen, methyl group, ethyl group, propyl group, butyl group, phenyl group, C1-C10 alkylphenyl group, C1-C10 alkoxyphenyl group, halophenyl group, cyanophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o-, m-, or p-tolyl group, o-, m-, or p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene)phenyl group, (N,N′-dimethyl)aminophenyl group, (N,N′-diphenyl)aminophenyl group, (C1-C10 alkylcyclohexyl)phenyl group, (anthryl)phenyl group, biphenyl group, C1-C10 alkylbiphenyl group, C1-C10 alkoxybiphenyl group, pentalenyl group, indenyl group, naphthyl group, C1-C10 alkylnaphthyl group, C1-C10 alkoxynaphthyl group, halonaphthyl group, cyanonaphthyl group, biphenylenyl group, C1-C10 alkyl biphenylenyl group, C1-C10 alkoxy biphenylenyl group, anthracenyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthraquinolyl group, methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptacenyl group, pyranthrenyl group, ovalenyl group, carbazolyl group, cyclopentyl group, cyclohexyl group, C1-C10 alkylcyclohexyl group, and C1-C10alkoxycyclohexyl group.

10. The arylene derivative of claim 1, wherein the arylene derivative is represented by one of Formulas 2 through 16:

11. The arylene derivative of claim 1, wherein the solubility of the arylene derivative in an organic solvent at 20° C. is more than 0.1% by weight.

12. An organic light emitting device, comprising: a first electrode;a second electrode; andan organic layer interposed between the first electrode and the second electrode, the organic layer formed by forming a layer comprising the arylene derivative of claim 1 by a wet method or a laser induced thermal imaging method and thermolyzing the layer comprising the arylene derivative.

13. An organic light emitting device, comprising: a first electrode;a second electrode; andan organic layer interposed between the first electrode and the second electrode, the organic layer formed by forming a layer having an arylene derivative represented by Formula 1 and thermolyzing the layer having the arylene derivative:

14. The organic light emitting device of claim 13, wherein the formation of the layer having the arylene derivative is performed by using a laser induced thermal imaging method or a wet method selected from the group consisting of spin coating, inkjet printing, spray printing, and heat transferring.

15. The organic light emitting device of claim 13, wherein the temperature of the thermolysis is in the range of 100 to 500° C.

16. The organic light emitting device of claim 13, wherein the organic layer is one of an emitting layer and a hole transport layer.

17. The organic light emitting device of claim 13, further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the first electrode and the second electrode.

18. The organic light emitting device of claim 13, wherein the device has a structure of one selected from the group of a first electrode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/second electrode structure, a first electrode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/second electrode structure, and a first electrode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/second electrode structure.

19. The organic light emitting device of claim 16, wherein the light emitting layer includes one of a phosphorescent and fluorescent dopant which emits red, green, blue, or white light.

20. An organic light emitting device, comprising: a first electrode;a second electrode; andan organic layer interposed between the first electrode and the second electrode, the organic layer comprising a styryl-based compound formed by thermally-treating an arylene derivative represented by Formula 1:

21. A method of manufacturing an organic light emitting device, comprising: preparing a first electrode;forming an organic layer formed on the first electrode, the organic layer including an arylene derivative represented by Formula 1:

22. The method of claim 21, wherein the formation of the organic layer having the arylene derivative is performed by using a laser induced thermal imaging method or a wet method selected from the group consisting of spin coating, inkjet printing, spray printing, and heat transferring.

23. The method of claim 21, wherein the temperature of the thermolysis is in the range of 100 to 500° C.