KR101640285B1 - New compound and organic light emitting device using the same - Google Patents

Abstract

In the present specification, compounds capable of greatly improving lifetime, efficiency, electrochemical stability, and thermal stability of an organic light emitting device and an organic light emitting device including the compound in an organic material layer are described.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel compound and an organic light-

This application claims the benefit of Korean Patent Application No. 10-2012-0058947 filed on May 31, 2012, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound and an organic light emitting device in which the compound is contained in an organic material layer.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between an anode and a cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the luminescent material, a material having both a p-type property and an n-type property, that is, a material having both a stable state in oxidation and in a reduced state is preferable, and a material having high luminescence efficiency, desirable.

Korean Patent Publication No. 10-2003-0067773

Development of an organic light emitting device capable of satisfying a condition required for a material usable in an organic light emitting device, for example, an appropriate energy level, an electrochemical stability, and a thermal stability is required. Accordingly, there is a need to develop a compound having a chemical structure capable of performing various functions required in an organic light emitting device according to a substituent, and an organic light emitting device containing the compound.

The present invention provides a compound of formula (1).

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₁₉ are each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A halogen group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P A substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P An aryl group having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one member selected from the group consisting of a substituted or unsubstituted heteroaryl group having 1 to 6 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P An arylalkyl group having 7 to 40 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of a substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having O, N, S, or P as a hetero atom, A substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having O, N, S, or P as a hetero atom, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms; Or -NR'R ", wherein R 'and R" are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted heterocycloalkyl group, An unsubstituted arylalkyl group, or a substituted or unsubstituted heteroaryl group having hetero atom O, N, S or P,

At least one of R ₁ to R ₁₉ is represented by the following formula (2)

(2)

In Formula 2,

Y ₁ and Y ₂ are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P A substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having O, N, S, or P, a substituted or unsubstituted heterocycloalkyl group having a hetero atom, a nitro group, a nitrile group, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, An unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a hetero atom, O, N, S, or P An aryl group having 6 to 60 carbon atoms, which is substituted or unsubstituted with at least one member selected from the group consisting of a substituted or unsubstituted heteroaryl group having 1 to 6 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having O, N, S, or P as a hetero atom, A substituted or unsubstituted arylalkyl group having 7 to 60 carbon atoms; A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having O, N, S, or P as a hetero atom, A substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having O, N, S, or P as a hetero atom, A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,

At least one of Y ₁ and Y ₂ is a group selected from the group consisting of deuterium, nitro, nitrile, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted alkoxy A substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, or a heterocyclic group having O, N, S, or P, or a substituted or unsubstituted aryl group, a substituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted fluorenyl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryloxy group, Substituted or unsubstituted heteroaryl group having O, N, S or P as a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, And a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

Also, the present invention provides an organic light emitting device comprising a first electrode, a second electrode, and at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound represented by Formula 1 And an organic electroluminescent device.

The compound of the present invention can be used as an organic layer material in an organic light emitting device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like. When the compound of the present invention is used in an organic light emitting device, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

Fig. 1 shows an example of an organic light emitting element comprising a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4. Fig.
2 shows an organic light emitting device 1 including a substrate 1, a first electrode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 8 and a second electrode 4 Fig.
Fig. 3 is a view showing synthesis confirmation data of the structural formula B of Production Example 1 of the present invention. Fig.
4 is a view showing synthesis confirmation data of the structural formula 1 of Production Example 1 of the present invention.

Hereinafter, the present invention will be described in detail.

In the present invention, the formula (1) may be represented by any one of the following formulas (3) to (6), but is not limited thereto.

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the formulas (3) to (6), Y ₁ and Y ₂ are as defined in the formulas (1) and (2).

In the general formula (1), the halogen group may be fluorine, chlorine, bromine or iodine.

In the formula (1), the alkyl group may be linear, branched or cyclic. The number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples thereof include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, A cyclopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, but is not limited thereto.

In the general formula (1), the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a n-propyloxy group, an iso-propyloxy group, a n-butyloxy group, and a cyclopentyloxy group.

In the above formula (1), the alkenyl group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkenyl group is not particularly limited, but is preferably 1 to 20 carbon atoms. The number of double bonds of the alkenyl group is not particularly limited, but it is preferable that the double bond has 1 to 10 bonds. Specific examples include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a butadienyl group, a pentadienyl group, a hexadienyl group, a hexatrienyl group, a cyclopentenyl group, a cyclohexenyl group, a cyclopentadienyl group, Cyclohexadienyl group, and the like, but is not limited thereto.

In the above formula (1), the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a stilbenyl group, and the like. Examples of the polycyclic aryl group include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, klycenyl,

In the general formula (1), the arylalkyl group is a substituent in which an alkyl group is substituted with an aryl group. The number of carbon atoms is not particularly limited, but is preferably 7 to 60 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the above formula (1), the heteroaliphatic cyclic group is a cyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 50 carbon atoms. Specific examples thereof include an epoxy group, an oxyethylene group, a tetrahydrofuran group, a 1,4-dioxolane group, a 1,3-dioxane group, a pyrrolidine group, a piperidine group and a tetrahydrothiophene group. But is not limited thereto.

In the above formula (1), the heteroaryl group is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 50 carbon atoms. Specific examples of the substituent include a furan group, a pyrrolyl group, a thiophene group, an imidazole group, an oxazole group, a thiazole group, a triazole group, a pyridyl group, a pyridazyl group, a quinolinyl group, an isoquinolinyl group, But are not limited thereto.

In the above formula (1), "substituted or unsubstituted" means a group selected from the group consisting of a halogen group, a nitrile group, a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryloxy group, An alkyl group, an aryl group, an aryl group, a fluorenyl group, a carbazole group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, an arylalkoxy group, an arylalkoxy group, And an acetylene group, or does not have any substituent (s).

In Formula 1, R ₁ to R ₁₉ are each independently hydrogen; Or an aryl group having 6 to 20 carbon atoms and is preferably a hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a stilbene group, a naphthyl group, an anthracenyl group, a phenanthrene group, a pyrenyl group, or a perylenyl group More preferable.

In Formula 1, Y ₁ and Y ₂ are preferably a heteroaryl group having 2 to 20 carbon atoms, and may be a furan group, a pyrrolyl group, a thiophene group, an imidazole group, an oxazole group, a thiazole group, More preferably a pyridyl group, a quinolinyl group, an isoquinolinyl group, or an acridyl group.

The above formula (2) is preferably selected from the substituents described in [Table A-1] below, but the present invention is not limited thereto.

[Table A-1]

The compound of Formula 1 may be a compound represented by any one of the following structural formulas, but is not limited thereto.

The compound of formula (I) according to the present invention can be prepared by a multistage chemical reaction. For example, some intermediate compounds may be prepared first, and compounds of formula (1) may be prepared from the intermediate compounds. More specific methods for preparing the compounds of formula (1) are described in the examples which follow.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap. As described above, since the core of the compound of Formula 1 contains limited conjugation, it has a large energy band gap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents at positions R ₁ to R ₁₉ , Y ₁ and Y ₂ of the core structure having a large energy bandgap as described above. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent.

In the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents at the R ₁ to R ₁₉ , Y _1, and Y ₂ positions of the core structure as described above. On the other hand, And the use of the material can be varied.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, a substance that satisfies the conditions required in each organic layer can be synthesized by introducing a substituent used for the hole injecting layer material, the hole transporting layer material, the light emitting layer material, and the electron transporting layer material used in manufacturing the organic light emitting device into the core structure .

In the present invention, a compound having an appropriate energy level according to the substituent among the compounds of the formula (1) is selected and used in an organic light emitting device, thereby realizing a device having a low driving voltage and a high light efficiency. Further, by introducing various substituent groups into the core structure, it is possible to finely control the energy band gap, and the characteristics at the interface between the organic materials can be improved and the use of the materials can be diversified.

On the other hand, the compound of formula (1) has a high glass transition temperature (Tg) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

A second aspect of the present invention is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a compound represented by the following formula (1): < EMI ID = 1.0 >

1 and 2 show an example of an organic light emitting device according to the present invention. FIG. 1 shows an example of an organic light emitting device including a substrate 1, a first electrode 2, a light emitting layer 3 and a second electrode 4 FIG. 2 is a sectional view showing the structure of a substrate 1, a first electrode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 8 and a second electrode 4, Emitting layer.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.

For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

That is, in the organic light emitting device, the organic material layer may include at least one of a hole injection layer and a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by Formula 1. In addition, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

The compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound represented by the above formula (1).

The organic light emitting device of the present invention can be manufactured, for example, by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. In this case, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation may be used, but the present invention is not limited to these methods.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using the same will be specifically described in the following Production Examples and Examples. However, the following Preparation Examples and Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

< Example >

< Manufacturing example  1> Preparation of the compound represented by the structural formula 1

Preparation of formula B

(0.1 g, 0.3 mmol) of t- BuONa (1.5 g, 15.5 mmol) and Pd (t-Bu ₃ P) ₂ (0.1 g, 0.3 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain the structural formula B (3.8 g, yield 75%).

MS: [M + H] &lt; ⁺ &gt; = 497

Preparation of formula 1

Pd (t-Bu ₃ P) ₂ (0.11 g, 0.21 mmol), Cs ₂ CO ₃ (3.4 g, 10.5 mmol), and Cs (1.9 g, 7.0 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain structural formula 1 (3.3 g, yield 63%).

MS: [M + H] &lt; ⁺ &gt; = 728

< Manufacturing example  2> Preparation of the compound represented by the structural formula 5

Preparation of formula 5

(0.19 g, 0.21 mmol), Pd (t-Bu ₃ P) ₂ (4.9 g, 15.1 mmol) and Cs ₂ CO ₃ (2.95 g, 11.1 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain the structural formula 5 (3.8 g, yield 52%).

MS: [M + H] &lt; ⁺ &gt; = 727

< Manufacturing example  3> Preparation of the compound represented by the structural formula 9

Preparation of Structural Formula 9

Structure B (5.5g, 11.1mmol) and formula E (3.2g, 12.2mmol), and _{Cs 2 CO 3 (5.4g, 16.6mmol} ), Pd (t-Bu 3 P) 2 (0.11g, 0.21mmol) to Giles Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain structural formula 9 (4.7 g, yield 58%).

MS: [M + H] &lt; ⁺ &gt; = 727

< Manufacturing example  4> Preparation of the compound represented by the structural formula 2

Preparation of Structural Formula G

(0.35 g, 0.7 mmol) of t- BuONa (9.8 g, 102.3 mmol) and Pd (t-Bu ₃ P) ₂ (30 g, 68.2 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain a structural formula G (24.4 g, yield 72%).

MS: [M + H] &lt; ⁺ &gt; = 497

Preparation of formula 2

Pd (t-Bu ₃ P) ₂ (0.09 g, 0.17 mmol), Cs ₂ CO ₃ (8.3 g, 25.4 mmol) and the formula C (5.0 g, 18.6 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain the structural formula 2 (6.0 g, yield 49%).

MS: [M + H] &lt; ⁺ &gt; = 728

< Manufacturing example  5> Structural formula To 6  Preparation of indicated compounds

Preparation of Structure 6

Pd (t-Bu ₃ P) ₂ (0.09 g, 0.1 mmol), Cs ₂ CO ₃ (7.9 g, 24.2 mmol) and the structural formula D (4.7 g, 17.7 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain the structural formula 6 (6.2 g, yield 53%).

MS: [M + H] &lt; ⁺ &gt; = 727

< Manufacturing example  6> Structural formula To 10  Preparation of indicated compounds

Preparation of formula 10

Pd (t-Bu ₃ P) ₂ (0.09 g, 0.1 mmol), Cs ₂ CO ₃ (7.9 g, 24.2 mmol) and the structural formula D (4.7 g, 17.7 mmol) Was dissolved in xylene (300 mL) and refluxed for 24 hours. The mixture was cooled to room temperature and then concentrated. The residue was purified by column chromatography to obtain structural formula 10 (6.6 g, yield 56%).

< Example  1>

A glass substrate coated with ITO (indium tin oxide) having a thickness of 500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

(NPB) (250 Å), hexanitrile hexaazatriphenylene (HAT) (50 Å), and the like were added to the hole injection layer. ) And 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400A) were successively vacuum-deposited to form a hole transport layer.

Subsequently, a compound having a thickness of 300 angstroms and a dopant compound GD shown below were vacuum deposited on the hole transport layer at a weight ratio of 10: 1 to form a light emitting layer.

[GD]

[ET-A]

[LiQ]

A compound of the above formula (ET-A) and the above-mentioned LiQ (Lithium Quinalate) were vacuum-deposited on the light emitting layer as an electron transporting layer material at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 300 Å.

Lithium fluoride (LiF) 15 Å thick and aluminum 1,000 Å thick were sequentially deposited on the electron injection and transport layer to form a cathode.

Was the deposition rate of the organic material in the above process, maintaining the 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was 0.3 Å / sec, aluminum was kept to 2 Å / sec, During the deposition, a vacuum 2 × 10 ^-7 ~ 5 x 10 &lt; ^-8 &gt; torr. Thus, an organic light emitting device was fabricated.

< Comparative Example  1>

An organic light emitting device was fabricated in the same manner as in Example except for using the compound of the formula GH-A instead of the compound synthesized in the above Examples.

[GH-A]

< Experimental Example  1>

When a current (10 mA / cm ² ) was applied to the organic light-emitting device manufactured by the example and the comparative example 1, the results shown in Table 1 were obtained.

[Table 1]

From the results of Table 1, it can be seen that the novel compound according to the present invention can be used as a material for a light emitting layer of an organic electronic device including an organic light emitting device, and an organic electronic device including the organic light emitting device can be used It can be seen that it exhibits excellent characteristics. Particularly, it is possible to lower the driving voltage and induce an increase in efficiency, thereby improving the power consumption.

Claims (8)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
At least one of R ₁ to R ₁₉ is selected from the substituents described in Table A-1 below, and the remainder is hydrogen.
[A-1]

The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (3) to (6)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the formulas (3) to (6), Y ₁ and Y ₂ are as defined in the formulas (1) and (2). delete The compound of claim 1, wherein the compound is represented by one of the following formulas:

1. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers is a compound represented by any one of claims 1, 2 and 4 And a compound represented by the general formula (1). [7] The organic light emitting device of claim 5, wherein the organic layer comprises at least one of a hole injection layer and a hole transport layer, and at least one layer of the hole injection layer and the hole transport layer comprises the compound of Formula 1. [7] The organic light emitting device of claim 5, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1. [7] The organic light emitting device according to claim 5, wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises the compound of Formula 1. [

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