KR20140065357A - Organic light emitting device material and organic light emitting device comprising the same - Google Patents

Abstract

Provided in the present invention are a compound significantly improving the life, efficiency, electrochemical stability, and thermal stability of an organic electronic device, and an organic electronic device having the compound contained in an organic compound layer. The present invention has a purpose of providing a hetero compound derivative having a chemical structure satisfying the conditions required for a material used in an organic electronic device, for example a proper energy level, electrochemical stability, and thermal stability, and acting various roles required in an organic electronic device according to a substituent.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an organic electronic device material, and an organic electronic device including the same. BACKGROUND OF THE INVENTION [0002]

TECHNICAL FIELD The present invention relates to an organic electronic device material and an organic electronic device including the same.

This application claims the benefit of Korean Patent Application No. 10-2012-0132644 filed on November 21, 2012 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electric device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor that interfaces with an electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

Korean Patent Publication No. 2007-0078724

Therefore, the present inventors have found that a compound capable of satisfying the conditions required for a material usable in an organic electronic device, for example, an appropriate energy level, an electrochemical stability, and a thermal stability, Structure and an organic electronic device containing the same.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

a and b are integers of 0 to 4,

c is an integer of 0 to 6,

X is NR or O,

R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or -N (L) (Y); -CO-N (L) (Y); And -COO-L,

R ₁ to R ₃ are the same or different from each other and each independently form a double bond with an adjacent cyclic carbon; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or -N (L) (Y); -CO-N (L) (Y); And -COO-L, or two adjacent substituents may form a condensed ring,

L and Y are the same or different and each independently represents a hydrogen, a halogen group, an alkyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A heterocyclic group containing at least one unsubstituted or at least one of N, O and S atoms, and a nitrile group.

Further, the present specification discloses an organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers has a structure represented by Formula Wherein the organic compound is a compound represented by formula (I).

The compound of the present invention can be used as an organic material layer material, particularly a hole injecting material and / or a hole transporting material in an organic electronic device. When the compound is used in an organic electronic device, the driving voltage of the device is lowered, The lifetime characteristics of the device can be improved by the thermal stability of the device.

1 to 5 are cross-sectional views illustrating the structure of an organic electronic device according to the present invention.
6 is a diagram showing the mass spectrum of Compound 17;
7 is a diagram showing the mass spectrum of Compound 41. Fig.
8 is a diagram showing the mass spectrum of the compound 65. Fig.

The present invention provides a compound represented by the above formula (1).

In one embodiment, R in Formula 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group Substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted tetracenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted tetracenyl groups, A substituted or unsubstituted acenaphthacenyl group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted fluoranthene group.

In one embodiment of the present invention, X in the formula (1) is NR.

In one embodiment of the present invention, the benzimidazole, the benzene ring, and the carbazole or dibenzofuran are bonded to form a six-membered ring.

In another embodiment, Formula 1 bonds to the N and carbazole groups of the benzimidazole, and C of the benzimidazole bonds to the benzene ring.

In another embodiment, in Formula 1, N of the benzimidazole is bonded to the benzene ring, and C of the benzimidazole is bonded to the carbazole group.

In another embodiment, the benzimidazole, the benzene ring, the benzimidazole and the carbazole group are bonded to each other and the carbazole group adjacent to the benzene ring is bonded to form a six-membered ring.

In addition, the compound represented by the formula (1) in the present specification may be represented by any one of the following formulas (2) to (6).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 2 to 6, R, R ₁ to R ₃ , a, b and c are the same as defined in the above formula (1).

In one embodiment of the present disclosure, R < _{1 >} To R < ₃ > are the same as or different from each other, and two adjacent substituents independently from each other may form a condensed ring.

The condensed ring is a polycyclic or monocyclic ring, a hydrocarbon ring or a heterocyclic ring, and is an aliphatic or aromatic 5-membered or 6-membered ring.

In the state of the present specification, when two or more condensed rings are formed, one may be a polycyclic ring and the other may form a monocyclic ring.

In another embodiment, when two or more condensed rings are formed, one may be a hydrocarbon ring and the other may form a heterocyclic ring.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.

The length of the alkyl group, alkenyl group and alkoxy group contained in the compound does not affect the conjugation length of the compound but affects the application of the compound to the organic electronic device, for example, the vacuum deposition method or the solution application method. The number of carbon atoms is not particularly limited.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

In the present specification, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Specific examples of the aryl group include monocyclic aromatic and naphthyl groups such as phenyl group, biphenyl group, terphenyl group and stilbene group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, An acenaphthacenyl group, a triphenylene group, and a fluoranthene group, but the present invention is not limited thereto.

등이 있다. In the present specification, a fluorenyl group is a structure in which two ring organic compounds are connected via one atom,

.

등이 있다. In the present specification, a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example,

.

In the present specification, the heterocyclic group is a hetero ring group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzoxazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to these.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the alkylthio group, alkylsulfoxy group, alkylamine group, and aralkylamine group is the same as the alkyl group described above.

In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

The term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; An aryl group; A nitrile group; A nitro group; A hydroxy group; And a heterocyclic group containing at least one of N, O and S atoms, or does not have any substituent (s).

In one embodiment of the present disclosure, R ₁ is hydrogen.

In one embodiment of the present disclosure, R ₂ is hydrogen.

In one embodiment of the present disclosure, R < ₃ > is hydrogen.

In one embodiment of the present specification, R is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In another embodiment, R is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

In another embodiment, R is a phenyl group substituted with a phenyl group.

또는

이며, In another embodiment, R is a phenyl group substituted with a carbazole group. In this case, the carbazole group

or

Lt;

* Is a moiety connected to a phenyl group.

또는

이며, *는 페닐기와 연결되는 부분이다. In another embodiment, R is a phenyl group substituted with a dibenzofurane group. In this case, the dibenzofurane group

or

And * is a portion connected to a phenyl group.

또는

이며, *는 페닐기와 연결되는 부분이다. In another embodiment, R is a phenyl group substituted with a dibenzothiophene group. In this case, the dibenzothiophene group

or

And * is a portion connected to a phenyl group.

In one embodiment of the present invention, R is a phenyl group.

이고, R은 페닐기이다. In one embodiment of the present specification, R is a phenyl group substituted by the general formula (2). For example, the formula (1)

And R is a phenyl group.

In one embodiment of the present specification, the substituted phenyl group is a 1,4-phenyl group or a 1,3-phenyl group.

In one embodiment of the present specification, R is a substituted or unsubstituted carbazole group.

In another embodiment, R is a carbazole group.

In another embodiment, R is a carbazolyl group substituted with a phenyl group.

In another embodiment, R is a carbazolyl group substituted with a biphenyl group.

In another embodiment, R is a substituted or unsubstituted triazine group.

In another embodiment, R is a triazine group substituted with a phenyl group.

또는

이고, *는 화학식 1과 연결되는 부분이다. In another embodiment, R is a substituted or unsubstituted pyrimidine group. In this case, the pyrimidine group is

or

And * is a moiety connected to the formula (1).

In another embodiment, R is a pyrimidine group substituted or unsubstituted with a phenyl group.

In another embodiment, R is a substituted or unsubstituted dibenzofurane group.

In another embodiment, R is a substituted or unsubstituted dibenzothiophene group.

이고, R은 페닐기이다. In one embodiment of the present invention, R is a phenyl group substituted by the formula (3). For example,

And R is a phenyl group.

이고, R은 페닐기이다. In one embodiment of the present specification, R is a phenyl group substituted by the formula (4). For example, the formula (1)

And R is a phenyl group.

이고, R은 페닐기이다. In one embodiment of the present invention, R is a phenyl group substituted by the formula (5). For example, the formula (1)

And R is a phenyl group.

이고, R은 페닐기이다. In one embodiment of the present specification, R is a phenyl group substituted by the formula (6). For example, the formula (1)

And R is a phenyl group.

In the present specification, the formula (2) can be exemplified by any one of the following compounds, but the range of the compounds of the present invention is not limited by the following compounds.

In the present specification, the formula (3) can be exemplified by any one of the following compounds, but the range of the compounds of the present invention is not limited by the following compounds.

In the present specification, the formula (4) can be exemplified by any one of the following compounds, but the range of the compound of the present invention is not limited by the following compounds.

In the present specification, the above-mentioned formula (5) can be exemplified by any one of the following compounds, but the range of the compounds of the present invention is not limited by the following compounds.

In the present specification, the above-mentioned formula (6) can be exemplified by any one of the following compounds, but the range of the compounds of the present invention is not limited by the following compounds.

The compound of formula (1) may be prepared based on the preparation examples described below.

In the present specification, the compound represented by the formula (1) can be prepared through the ring-closing reaction after coupling benzoimidazophenanthridine substituted with boronic acid to bromonitrobenzene.

A compound represented by the general formula (1) can be prepared in addition to the compounds 1 to 120 by substituting a desired substituent with a halogenated or boronic acid substituted structure.

In the present specification, the compound of formula (I) is prepared by a method of forming a condensation ring containing nitrogen or oxygen in a compound in which two phenyl groups are substituted on the benzimidazole group in the same manner as described above to form a condensed ring.

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 contains a limited conjugation, it has a large energy band gap property.

In this specification, compounds having various energy bandgaps can be synthesized by introducing various substituents at the positions of R, R ₁ to R _{3 in} the core structure having a large energy band gap as described above. Usually, it is easy to control the energy band gap by introducing a substituent into 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 this specification, the HOMO and LUMO energy levels of a compound can be controlled by introducing various substituents at the positions of R, R ₁ to R ₃ in the core structure having the above structure.

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, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic electronic device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Since the benzoimidazole, benzene ring and carbazole or dibenzofuran are bonded to the core structure to form a ring, the compound can have an appropriate energy level as a hole injecting and / or hole transporting material in an organic electronic device.

In this specification, a compound having an appropriate energy level according to a substituent among the above compounds is selected and used in an organic electronic 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 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.

The present invention also provides an organic electronic device using the compound of formula (1).

In one embodiment of the present invention, the organic electronic device may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween.

The organic electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor.

In one embodiment of the present invention, the organic electronic device may be an organic light emitting device.

In one embodiment of the present disclosure, an organic light-emitting device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes And a compound represented by the formula (1).

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 in this specification 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.

Therefore, in another embodiment of the present disclosure, the organic material layer of the organic light emitting device may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Layer may contain a compound represented by the above formula (1).

Specifically, the organic material layer of the organic light emitting device may include a hole injection layer, and the hole injection layer may include a compound represented by the formula (1).

In another example, the organic material layer of the organic light emitting device may include a hole transporting layer, and the hole transporting layer may include a compound represented by the above formula (1).

In another example, the organic material layer of the organic light emitting device may include a hole transporting layer and a hole injecting layer, and the hole transporting layer and the hole injecting layer may include a compound represented by the above formula (1).

In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

As one example, the compound represented by Formula 1 may be included as a host of the light emitting layer.

As another example, the organic layer containing the compound represented by Formula 1 may include the compound represented by Formula 1 as a host, and may include another organic compound, metal, or metal compound as a dopant.

The organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports electrons and electron injection, and at least one of the layers may include a compound represented by Formula 1 . Specifically, the organic material layer of the organic light emitting device may include an electron injection layer, and the electron injection layer may include the compound represented by Formula 1. [

In another example, the organic material layer of the organic light emitting device includes an electron transporting layer, and the electron transporting layer includes a compound represented by the above formula (1).

In another embodiment, the organic material layer of the organic light emitting device may include an electron injection layer, and the electron injection layer may include a compound represented by the formula (1).

In the organic compound layer having such a multi-layer structure, the compound represented by Formula 1 may be included in a light emitting layer, a layer that simultaneously transports and injects holes, a layer that simultaneously transports light and emits light, or a layer that simultaneously transports electrons and emits light have.

In another embodiment, the organic material layer of the organic light emitting device may include a hole injecting layer containing a compound containing an arylamino group, a carbazole group, or a benzoxazole group, in addition to an organic material layer containing a heterocyclic compound represented by the formula Or a hole transporting layer.

In one embodiment of the present invention, the organic electronic device may be an organic solar cell.

In one embodiment of the present disclosure, the organic electroluminescent device includes at least one organic layer including a first electrode, a second electrode, and a photoactive layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers Is a heterocyclic compound represented by the general formula (1).

In one embodiment of the present invention, the organic solar cell may include a charge generation layer, and the charge generation layer may include a compound represented by the above formula (1).

In another embodiment, the photoactive layer may comprise a compound represented by Formula 1. [

In another embodiment, the organic solar cell may include a photoactive layer, an electron donor, and an electron acceptor. The photoactive layer and the electron donor or electron acceptor may be represented by Formula 1 ≪ / RTI >

In the embodiment of the present invention, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron beams and the electron acceptors. The generated holes are transported to the anode through the electron donor layer.

In an embodiment of the present disclosure, the organic solar cell may further include an additional organic layer. The organic solar cell can reduce the number of organic layers by using organic materials having various functions at the same time.

In one embodiment of the present disclosure, the organic electronic device may be an organic transistor.

In one embodiment of the present disclosure, an organic transistor is provided that includes a source, a drain, a gate, and one or more organic layers.

In one embodiment of the present disclosure, the organic transistor may include a charge generation layer, and the charge generation layer may include a compound represented by the above formula (1).

In another embodiment, the organic transistor may comprise an insulating layer, and the insulating layer may be located on the substrate and the gate.

When the organic electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

 The organic electronic device according to the present invention may have a structure as shown in Figs. 1 to 5, but the present invention is not limited thereto.

1 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially stacked Structure is illustrated.

2 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked.

3 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked.

4 shows a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated.

5 illustrates a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated.

The organic electronic 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 includes the compound of the present invention, i.e., the compound of the above formula (1).

For example, the organic electronic device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic electronic device can be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. (International Patent Application Publication No. 2003/012890)

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic electronic device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

The substrate may be a glass substrate or a plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto and is not limited as long as it is a substrate commonly used in an organic electronic device.

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] (PEDOT), 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 is 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 porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting 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 receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good 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 suitable for electrons, 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 electronic device according to the present invention may be a top 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 production of the organic electronic device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Synthetic example  1>

(6.2 g, 30 mmol), and potassium carbonate (12 g, 86 mmol) were dissolved in tetrahydrofuran (200 mL) and water (100 mL) &Lt; / RTI &gt; After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 24 hours and then cooled to room temperature. The mixed solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then decompressed to remove the solvent. The resulting solid was purified by THF / EtOH to give compound P2 (10.1 g, 26 mmol, yield 86%). MS: [M + H] &lt; + &gt; = 390

Preparation of compound P3: Compound P2 (7 g, 18 mmol) was added to triethyl phosphite (50 mL), followed by reflux stirring for about 24 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The resulting solid was purified by THF / EtOH to give compound P3 (4.5 g, 12 mmol, 66%). MS: [M + H] &lt; + &gt; = 358

< Synthetic example  2>

(10 g, 25 mmol), 2-bromonitrobenzene (5.2 g, 25 mmol) and potassium carbonate (10 g, 72 mmol) were dissolved in tetrahydrofuran (200 mL) and water (100 mL) &Lt; / RTI &gt; After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 24 hours and then cooled to room temperature. The mixed solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then decompressed to remove the solvent. The resulting solid was purified with CHCl ₃ / Hexanes to prepare a compound P5 (9.1g, 23 mmol, 92% yield). MS: [M + H] &lt; + &gt; = 390

Preparation of compound P6: Compound P5 (9 g, 23 mmol) was added to triethyl phosphite (50 mL), followed by reflux stirring for about 24 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The resulting solid was purified with THF / EtOH to give compound P6 (6.7 g, 18 mmol, 78%). MS: [M + H] &lt; + &gt; = 358

< Synthetic example  3>

(10 g, 25 mmol), 2-bromonitrobenzene (5.2 g, 25 mmol) and potassium carbonate (10 g, 72 mmol) were dissolved in tetrahydrofuran (200 mL) and water (100 mL) &Lt; / RTI &gt; After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 24 hours and then cooled to room temperature. The mixed solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then decompressed to remove the solvent. Purification of the resulting solid with CHCl ₃ / Hexanes to prepare a compound P8 (7.8g, 20 mmol, 80% yield). MS: [M + H] &lt; + &gt; = 390

Preparation of Compound P9: Compound P8 (7 g, 18 mmol) was added to triethylphosphite (50 mL), followed by reflux stirring for about 24 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The resulting solid was purified by THF / EtOH to give P9 (5.2 g, 14 mmol, 77%). MS: [M + H] &lt; + &gt; = 358

< Synthetic example  4>

(15 g, 38 mmol), 2-bromonitrobenzene (7.7 g, 38 mmol) and potassium carbonate (15 g, 100 mmol) were dissolved in tetrahydrofuran (200 mL) and water (150 mL) &Lt; / RTI &gt; After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 24 hours and then cooled to room temperature. The mixed solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then decompressed to remove the solvent. Purification of the resulting solid with CHCl ₃ / Hexanes to prepare a compound P11 (12.5g, 30 mmol, 83% yield). MS: [M + H] &lt; + &gt; = 390

Preparation of the compounds P12 and P13: Compound P11 (12 g, 18 mmol) was added to triethylphosphite (50 mL), followed by reflux stirring for about 24 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The resulting solid was subjected to column purification with hexane / dichloromethane (CH ₂ Cl ₂ ) = 1/2 and then recrystallized in ethyl acetate to obtain P12 (2.5 g, 7 mmol, 38%) and P13 (1.9 g, 5.3 mmol , 29%). MS: [M + H] &lt; + &gt; = 358

< Synthetic example  5>

Preparation of compound P14: Compound P3 (10 g, 28 mmol), 4-bromoiodobenzene (16 g, 56 mmol) and potassium carbonate (7 g, 50 mmol) were suspended in xylene (200 mL). After nitrogen charging, copper iodide (5.4 g, 28 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 12 hours. The solid was filtered in a hot state, and the solvent of the filtrate was removed by decompression. Column purification was performed with hexane / dichloromethane (CH ₂ Cl ₂ ) = 1/2 and then recrystallized in ethyl acetate to obtain P14 (7.1 g, 13 mmol, 46%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  6>

Preparation of compound P15: Compound P3 (7.1 g, 19 mmol), 3-bromoiodobenzene (12 g, 42 mmol) and potassium carbonate (5 g, 36 mmol) were suspended in xylene (200 mL). After nitrogen charging, copper iodide (3.8 g, 19 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 12 hours. The solid was filtered in a hot state, and the solvent of the filtrate was removed by decompression. After column purification with hexane / dichloromethane (CH ₂ Cl ₂ ) = 1/2, the product was recrystallized from THF / Hexanes to give P15 (6.5 g, 12 mmol, 63%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  7>

Preparation of compound P16: P16 was prepared using compound P6 (8.8 g, 24 mmol) and 4-bromoiodobenzene (14 g, 49 mmol) according to the method for preparing compound P14. After column purification with hexane / dichloromethane (CH ₂ Cl ₂ ) = 1/2, recrystallization from THF / Hexanes gave P16 (5.2 g, 10 mmol, 41%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  8>

Preparation of Compound P17 P17 was prepared using Compound P6 (9.0 g, 25 mmol) and 3-bromoiodobenzene (15 g, 53 mmol) according to the method for preparing Compound P14. After column purification with hexane / dichloromethane (CH ₂ Cl ₂ ) = 1/2, recrystallization in ethyl acetate gave P17 (6.3 g, 12 mmol, 48%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  9>

Preparation of Compound P18: P18 was prepared using compound P9 (8.5 g, 23 mmol) and 4-bromoiodobenzene (14 g, 49 mmol) according to the preparation method of compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P18 (6.0 g, 11 mmol, 47%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  10>

Preparation of Compound P19: P19 was prepared using compound P9 (6.3 g, 17 mmol) and 3-bromoiodobenzene (10 g, 35 mmol) according to the method for preparing compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P19 (4.9 g, 9.5 mmol, 56%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  11>

Preparation of compound P20: P20 was prepared using compound P12 (4.3 g, 12 mmol) and 4-bromoiodobenzene (6.8 g, 24 mmol) according to the preparation method of compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P20 (3.0 g, 5.8 mmol, 48%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  12>

Preparation of Compound P21: Compound P12 (3.8 g, 10 mmol) and 3-bromoiodobenzene (6.0 g, 20 mmol) were used to prepare P21 according to the method for preparing Compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P21 (1.8 g, 3.5 mmol, 35%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  13>

Preparation of compound P22: P22 was prepared using compound P13 (2.5 g, 6.7 mmol) and 4-bromoiodobenzene (3.9 g, 13 mmol) according to the method for preparing compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P22 (1.8 g, 3.5 mmol, 52%). MS: [M + H] &lt; / RTI &gt; = 512

< Synthetic example  14>

Preparation of compound P23: P23 was prepared using compound P13 (2.3 g, 6.4 mmol) and 3-bromoiodobenzene (3.6 g, 12 mmol) according to the method for preparing compound P14. The residue was purified by column chromatography using chloroform and recrystallized from ethyl acetate to obtain P23 (1.5 g, 2.9 mmol, 45%). MS: [M + H] &lt; / RTI &gt; = 512

< Manufacturing example  1> Preparation of compound 1

Palladium (0.1 g, 0.2 mmol) and sodium tertiary-butoxide (2.5 g, 0.2 mmol) were added to a solution of compound P3 (6 g, 16 mmol), iodobenzene (5.1 g, 25 mmol) 26 mmol) were mixed and refluxed with xylene (150 ml) under nitrogen for 12 hours with stirring. After the completion of the reaction, the temperature was lowered to room temperature, and the solvent was distilled off under reduced pressure. The resulting solid was dissolved in chloroform, and an acidic white clay was added thereto, followed by stirring, followed by filtration and distillation under reduced pressure. Recrystallization from tetrahydrofuran and ethanol gave a white solid compound 1 (5.6 g, 12.9 mmol, 80%). MS: [M + H] &lt; + &gt; = 434

< Manufacturing example  2> Preparation of compound 2

Compound P3 (5.2 g, 14 mmol) and 4-iodo-1,1'-biphenyl (6.1 g, 21 mmol) were used according to the synthesis method of Preparation Example 1 Compound 2 was synthesized. After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from chloroform and ethyl acetate gave a white solid compound 2 (6.1 g, 12 mmol, 85%). MS: [M + H] &lt; + &gt; = 510

< Manufacturing example  3> Preparation of Compound 4

Compound 4 was synthesized according to the synthesis method of Preparation Example 1 using compound P14 (3.1 g, 6.0 mmol) and 9 H -carbazole (9 H -carbazole, 1.1 g, 6.5 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from chloroform and ethyl acetate gave a white solid compound 4 (1.3 g, 2.1 mmol, 35%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  4> Preparation of Compound 5

Compound 5 was synthesized according to the synthesis method of Preparation Example 1 using compound P15 (3.8 g, 7.4 mmol) and 9 H -carbazole (9 H -carbazole, 1.3 g, 7.7 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from tetrahydrofuran and ethyl acetate gave a white solid compound 5 (1.8 g, 3.0 mmol, 40%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  5> Preparation of Compound 7

(10 g, 19 mmol), dibenzofuran-4-boronicacid (4.1 g, 19 mmol) and potassium carbonate (8.0 g, 57 mmol) were dissolved in tetrahydrofuran (100 mL). After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.5 g, 0.44 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 12 hours and then cooled to room temperature. The resulting solid was filtered and then recrystallized from chloroform and ethyl acetate to obtain a white solid compound 7 (9.3 g, 15 mmol, 79%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  6> Preparation of Compound 8

(5 g, 9.7 mmol) and dibenzothiophen-4-boronic acid (2.2 g, 9.6 mmol) according to the method of preparation 5 to obtain 5.2 g , 8.4 mmol, 86%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  7> Preparation of Compound 9

(4.8 g, 9.3 mmol) and dibenzofuran-4-boronicacid (2.0 g, 9.4 mmol) according to the method of preparation 5 to obtain a white solid compound 9 , 7.3 mmol, 78%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  8> Preparation of Compound 10

(5.6 g, 10 mmol) and dibenzothiophen-4-boronic acid (2.5 g, 10 mmol) according to the method of Production Example 5 to obtain a white solid compound 10 g, 8.7 mmol, 87%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  9> Preparation of Compound 11

(3.9 g, 7.6 mmol) and dibenzofuran-2-boronic acid (1.7 g, 8.0 mmol) according to the method of Production Example 5 to obtain 3.6 g , 6.0 mmol, 79%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  10> Preparation of Compound 12

(4.5 g, 8.7 mmol) and dibenzothiophen-2-boronic acid (2.0 g, 8.7 mmol) according to the method of Preparation 5, the solid compound 12 g, 6.9 mmol, 79%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Production Example 11 > Preparation of Compound 13

(3.9 g, 7.6 mmol) and dibenzofuran-2-boronic acid (1.7 g, 8.0 mmol) according to the method of Production Example 5, 3.6 g , 6.0 mmol, 79%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  12> Preparation of Compound 14

(4.1 g, 8.0 mmol) and dibenzothiophen-2-boronic acid (1.9 g, 8.3 mmol) according to the method of Production Example 5 to obtain a white solid compound 14 g, 7.1 mmol, 88%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  13> Preparation of Compound 17

Compound P3 (4.3 g, 12 mmol) was added to DMF (50 mL), and NaH (60% dispersion in mineral oil, 0.57 g, 14 mmol) was slowly added thereto and stirred at room temperature for 10 minutes. 2-chloro-4,6-diphenyl-1,3,5-triazine (3.3 g, 12 mmol) was added to the solution, Lt; / RTI &gt; After adding water and hexane, the resulting solid was filtered. The filtered solid was recrystallized using chloroform and ethyl acetate to obtain a white solid compound 17 (5.2 g, 8.8 mmol, 73%). MS: [M + H] &lt; + &gt; = 589

< Manufacturing example  14> Preparation of Compound 18

According to the method of Preparation 13, compound P3 (4.8 g, 13 mmol) and 2-chloro-4,6-diphenylpyrimidine (3.6 g, 13 mmol) White solid compound 18 (5.0 g, 8.5 mmol, 65%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Manufacturing example  15> Preparation of Compound 19

According to the method of Preparation 13, compound P3 (5.1 g, 14 mmol) and 4-chloro-2,6-diphenylpyrimidine (3.8 g, 14 mmol) White solid compound 19 (5.8 g, 9.8 mmol, 70%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Manufacturing example  16> Preparation of Compound 25

According to the synthesis method of Preparation Example 1, a white solid compound 25 (5.2 g, 12 mmom, 75%) was synthesized by using Compound P6 (6.0 g, 16 mmol) and iodobenzene (6.8 g, 33 mmol). MS: [M + H] &lt; + &gt; = 434

< Manufacturing example  17> Preparation of Compound 26

According to the synthesis method of Preparation Example 1, Compound P6 (4.8 g, 13 mmol) and 4-iodo-1,1'-biphenyl (7.5 g, 26 mmol) Compound 26 was synthesized. After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. And recrystallized from chloroform and ethyl acetate to obtain a white solid compound 26 (4.5 g, 8.8 mmol, 67%). MS: [M + H] &lt; + &gt; = 510

< Manufacturing example  18> Preparation of Compound 28

Compound 28 was synthesized according to the synthesis method of Preparation Example 1 using compound P16 (3.5 g, 6.8 mmol) and 9 H -carbazole (9 H -carbazole, 1.2 g, 7.1 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. And recrystallized from chloroform and ethyl acetate to obtain a white solid compound 28 (2.1 g, 3.5 mmol, 51%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  19> Preparation of Compound 29

Compound 29 was synthesized according to the synthesis method of Preparation Example 1 using compound P17 (4.5 g, 8.7 mmol) and 9 H -carbazole (9 H -carbazole, 1.5 g, 8.9 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from tetrahydrofuran and ethyl acetate gave a white solid compound 29 (4.1 g, 6.8 mmol, 78%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  20> Preparation of Compound 31

(5.5 g, 10 mmol) and dibenzofuran-4-boronic acid (2.3 g, 10 mmol) according to the method of Production Example 5 to obtain a white solid compound 31 , 8.8 mmol, 88%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  21> Preparation of Compound 32

According to the method of Preparation 5, white solid compound 32 (5.9 g, 12 mmol) was obtained by using compound P16 (6.1 g, 12 mmol) and dibenzothiophen-4-boronic acid g, 9.5 mmol, 79%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  22> Preparation of Compound 33

(5.7 g, 11 mmol) and dibenzofuran-4-boronic acid (2.4 g, 11 mmol) according to the method of Production Example 5 to obtain a white solid compound 33 , 8.8 mmol, 80%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  23> Preparation of Compound 34

(5.7 g, 11 mmol) and dibenzothiophen-4-boronic acid (2.7 g, 11 mmol) according to the method of Production Example 5, white solid compound 34 g, 8.2 mmol, 74%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  24> Preparation of Compound 35

According to the method of Preparation Example 5, white solid compound 35 (3.8 g, 8.0 mmol) was obtained by using Compound P16 (4.1, 8.0 mmol) and dibenzofuran-2-boronic acid (1.7 g, 8.0 mmol) 6.3 mmol, 78%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  Preparation of Compound 36

(4.6 g, 8.9 mmol) and dibenzothiophen-2-boronic acid (2.0 g, 8.7 mmol) according to the method of preparation 5, the solid compound 36 g, 6.1 mmol, 68%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  26> Preparation of Compound 37

(5.5 g, 10 mmol) and dibenzofuran-2-boronic acid (2.3 g, 10 mmol) according to the method of Production Example 5 to obtain a white solid compound 37 , 9 mmol, 90%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  27> Preparation of Compound 38

(5.8 g, 11 mmol) and dibenzothiophen-2-boronic acid (2.8 g, 12 mmol) according to the method of Production Example 5 to obtain a white solid compound 38 g, 8.7 mmol, 79%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  28> Preparation of Compound 41

Following the procedure of Preparation 13, the compound P6 (5.6 g, 15 mmol) and 2-chloro-4,6-diphenyl-1, 3,5-triazine, 4.3 g, 16 mmol), a white solid compound 41 (5.9 g, 10 mmol, 66%) was obtained. MS: [M + H] &lt; + &gt; = 589

< Manufacturing example  Preparation of Compound 42

According to the method of Preparation 13, compound P6 (4.8 g, 13 mmol) and 2-chloro-4,6-diphenylpyrimidine (3.6 g, 13 mmol) White solid compound 42 (5.9 g, 10 mmol, 76%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Manufacturing example  30> Preparation of Compound 43

According to the method of Preparation 13, compound P6 (5.1 g, 14 mmol) and 4-chloro-2,6-diphenylpyrimidine (3.8 g, 14 mmol) White solid 43 (6.1 g, 10 mmol, 71%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Manufacturing example  31> Preparation of Compound 49

A white solid compound 49 (5.1 g, 11 mmol, 78%) was synthesized according to the synthesis method of Preparation Example 1 using Compound P9 (5.1 g, 14 mmol) and iodobenzene (6.8 g, 29 mmol). MS: [M + H] &lt; + &gt; = 434

< Manufacturing example  32> Preparation of Compound 50

The compound P9 (3.0 g, 8.4 mmol) and 4-iodo-1,1'-biphenyl (4.7 g, 16 mmol) were used according to the synthesis method of Preparation Example 1 Compound 50 was synthesized. After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from chloroform and ethyl acetate gave a white solid compound 50 (2.4 g, 4.7 mmol, 56%). MS: [M + H] &lt; + &gt; = 510

< Manufacturing example  33> Preparation of Compound 52

Compound 52 was synthesized according to the synthesis method of Preparation Example 1 using compound P18 (3.2 g, 6.2 mmmol) and 9 H -carbazole (9 H -carbazole, 1.2 g, 7.1 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from chloroform and ethyl acetate gave a white solid compound 52 (2.5 g, 4.1 mmol, 66%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  34> Preparation of Compound 53

Compound 53 was synthesized according to the synthesis method of Preparation Example 1 using compound P19 (4.0 g, 7.8 mmol) and 9 H -carbazole (9 H -carbazole, 1.4 g, 8.3 mmol). After the reaction, the resulting solid was filtered, and the filtered solid was dissolved in chloroform. The acidic white clay was added thereto and stirred, followed by filtration and distillation under reduced pressure. Recrystallization from tetrahydrofuran and ethyl acetate gave a white solid compound 53 (3.5 g, 5.8 mmol, 74%). MS: [M + H] &lt; + &gt; = 599

< Manufacturing example  Preparation of Compound 55

Using the compound P18 (5.0 g, 9.7 mmol) and dibenzofuran-4-boronic acid (2.1 g, 9.9 mmol) according to the method of preparation 5, white solid compound 55 (4.7 g , 7.8 mmol, 80%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  36> Preparation of Compound 56

(5.5 g, 10 mmol) and dibenzothiophen-4-boronic acid (2.5 g, 10 mmol) according to the method of Preparation 5 to obtain a white solid compound 56 g, 8.1 mmol, 81%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  Preparation of Compound 57

Using the compound P19 (5.1 g, 9.9 mmol) and dibenzofuran-4-boronic acid (2.1 g, 9.9 mmol) according to the method of Production Example 5, a white solid compound 57 , 6.6 mmol, 66%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  38> Preparation of Compound 58

(5.6 g, 11 mmol) and dibenzothiophen-4-boronic acid (2.7 g, 11 mmol) according to the method of preparation 5 to give a white solid compound 58 g, 7.9 mmol, 71%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  Preparation of Compound 59

According to the method of Preparation Example 5, white solid compound 59 (4.2 g, 8.9 mmol) was obtained by using compound P18 (4.5, 8.7 mmol) and dibenzofuran-2-boronic acid (1.9 g, 7.0 mmol, 80%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  40> Preparation of Compound 60

(5.7 g, 11 mmol) and dibenzothiophen-2-boronic acid (2.5 g, 10 mmol) according to the method of Production Example 5 to obtain a white solid compound 60 g, 8.2 mmol, 74%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  41> Preparation of Compound 61

(5.1 g, 9.9 mmol) and dibenzofuran-2-boronic acid (2.2 g, 10 mmol) according to the method of Production Example 5 to obtain a white solid compound 61 , 7.1 mmol, 71%). MS: [M + H] &lt; / RTI &gt; = 600

< Manufacturing example  42> Preparation of Compound 62

(5.8 g, 11 mmol) and dibenzothiophen-2-boronic acid (2.8 g, 12 mmol) according to the method of Production Example 5 to obtain a white solid compound 62 g, 8.1 mmol, 73%). MS: [M + H] = 616 &lt; RTI ID = 0.0 &gt;

< Manufacturing example  43> Preparation of Compound 65

Following the procedure of Preparation 13, the compound P9 (5.1 g, 14 mmol) and 2-chloro-4,6-diphenyl-1, 3,5-triazine, 4.3 g, 16 mmol), a white solid compound 65 (5.3 g, 9.0 mmol, 64%) was obtained. MS: [M + H] &lt; + &gt; = 589

< Manufacturing example  Preparation of Compound 66

(4.6 g, 12 mmol) and 2-chloro-4,6-diphenylpyrimidine (3.6 g, 13 mmol) according to the method of Production Example 13 White solid compound 66 (4.7 g, 8.0 mmol, 66%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Manufacturing example  45> Preparation of Compound 67

According to the method of Preparation 13, compound P9 (5.0 g, 14 mmol) and 4-chloro-2,6-diphenylpyrimidine (3.8 g, 14 mmol) White solid compound 67 (4.9 g, 8.3 mmol, 59%) was obtained. MS: [M + H] &lt; + &gt; = 588

< Experimental Example >

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

(1, 1-naphthalenyl) -N, N-bisphenyl- (1,1-biphenyl) -4,4-diamine (N, N-bis - (1-naphthalenyl) -N, N-bis-phenyl- (1,1-biphenyl) -4,4-diamine: NPB) was thermally vacuum deposited to a thickness of 400 Å to form a hole transport layer.

[NPB]

Subsequently, the compound 1 prepared in Preparation Example 1 was vacuum deposited on the hole transport layer to a thickness of 300 Å at a concentration of 10% with Ir (ppy) ₃ dopant to form a light emitting layer.

The following electron transporting material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injecting and transporting layer.

[Electron transport material]

Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and lithium aluminum fluoride (LiF) to a thickness of 2,000 Å 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, the aluminum was deposited at a rate of 2 Å / sec, During the deposition, a vacuum 2 ⅹ10 ^{- 7} to 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

< Experimental Example  2>

The same experiment was conducted except that Compound 5 was used instead of Compound 1 in Experimental Example 1.

< Experimental Example  3>

The same experiment was conducted except that Compound 17 was used in place of Compound 1 in Experimental Example 1 above.

< Experimental Example  4>

The same experiment was conducted except that Compound 18 was used in place of Compound 1 in Experimental Example 1.

< Experimental Example  5>

The same experiment was conducted except that Compound 25 was used in place of Compound 1 in Experimental Example 1 above.

< Experimental Example  6>

The same experiment was carried out except that Compound 29 was used instead of Compound 1 in Experimental Example 1 above.

< Experimental Example  7>

The same experiment was conducted except that Compound 34 was used instead of Compound 1 in Experimental Example 1.

< Experimental Example  8>

The same experiment was conducted except that Compound 41 was used in place of Compound 1 in Experimental Example 1 above.

< Experimental Example  9>

The same experiment was conducted except that Compound 49 was used in place of Compound 1 in Experimental Example 1 above.

< Experimental Example  10>

The same experiment was conducted except that Compound 65 was used in place of Compound 1 in Experimental Example 1 above.

< Experimental Example  11>

The same experiment was conducted except that Compound 67 was used in place of Compound 1 in Experimental Example 1 above.

< Comparative Example  1>

The same experiment was carried out except that the following H1 was used in place of the compound 1 in Experimental Example 1.

[H1]

Table 1 shows the device results obtained by using the respective compounds in Experimental Examples 1 to 11 and Comparative Example 1 as the light emitting layer.

No. Host
(Host) Dopant
(Dopant) Doping concentration
(%) The driving voltage (V)
@ 5,000 cd / m ² Luminous efficiency
(cd / A) Comparative Example 1 H1 Ir (ppy) ₃ 10 5.4 35 Experimental Example 1 Compound 1 Ir (ppy) ₃ 10 4.8 38 Experimental Example 2 Compound 5 Ir (ppy) ₃ 10 4.9 39 Experimental Example 3 Compound 17 Ir (ppy) ₃ 10 3.9 41 Experimental Example 4 Compound 18 Ir (ppy) ₃ 10 4.1 38 Experimental Example 5 Compound 25 Ir (ppy) ₃ 10 4.7 36 Experimental Example 6 Compound 29 Ir (ppy) ₃ 10 4.9 37 Experimental Example 7 Compound 34 Ir (ppy) ₃ 10 4.8 38 Experimental Example 8 Compound 41 Ir (ppy) ₃ 10 3.8 40 Experimental Example 9 Compound 49 Ir (ppy) ₃ 10 4.7 39 Experimental Example 10 Compound 65 Ir (ppy) ₃ 10 3.7 42 Experimental Example 11 Compound 67 Ir (ppy) ₃ 10 4.0 41

As can be seen from the above Table 1, the compounds of the present invention can be used as the host of the green light emitting layer in Experimental Examples 1 to 11, and can exhibit lower voltage characteristics and improved efficiency than Comparative Example 1.

1 substrate
2 anodes
3 hole injection layer
4 hole transport layer
5 Light emitting layer
6 electron transport layer
7 cathode

Claims (19)

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

In Formula 1,
a and b are integers of 0 to 4,
c is an integer of 0 to 6,
X is NR or O,
R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or -N (L) (Y); -CO-N (L) (Y); And -COO-L,
R1 to R3 are the same or different from each other and each independently form a double bond with the adjacent cyclic carbon or may be substituted with hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or -N (L) (Y); -CO-N (L) (Y); And -COO-L, or two adjacent substituents may form a condensed ring,
L and Y are the same or different and each independently represents a hydrogen, a halogen group, an alkyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, A heterocyclic group containing at least one of unsubstituted N, O, S atoms, and a nitrile group. [2] The method of claim 1, wherein R in the formula (1) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted fluorenyl group, Substituted acenaphthacenyl groups, substituted or unsubstituted triphenylene groups, and substituted or unsubstituted fluoranthene groups. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 6:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

R, R1 to R3, a, b and c are the same as defined in the above formula (1). 4. The compound according to claim 3, wherein the formula (2) is any one of the following compounds.

4. The compound according to claim 3, wherein the formula (3) is any one of the following compounds.

4. The compound according to claim 3, wherein the formula (4) is any one of the following compounds.

4. The compound according to claim 3, wherein the formula (5) is any one of the following compounds.

4. The compound according to claim 3, wherein the formula (6) is any one of the following compounds.

1. An organic electronic 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 provided in any one of claims 1 to 8 Wherein R &lt; 1 &gt; The organic electronic device according to claim 9, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, and an organic transistor. [Claim 11] The organic electroluminescent device according to claim 9, wherein the organic electronic device comprises at least one organic layer disposed between a first electrode, a second electrode, and the first electrode and the second electrode, Wherein the organic compound layer comprises an organic compound layer comprising the compound of Formula 1. [Claim 12] The organic electronic device according to claim 11, wherein the organic material layer comprises a hole injection layer or a hole transport layer containing the compound of Formula (1). [Claim 12] The organic electronic device according to claim 11, wherein the organic layer includes a light emitting layer containing the compound of Formula (1). [Claim 12] The organic electronic device according to claim 11, wherein the organic layer comprises an electron transport layer containing the compound of Formula (1). [Claim 12] The organic electroluminescent device according to claim 11, wherein the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group, or a benzoxazole group in addition to the organic material layer containing the compound of Formula . [Claim 12] The organic electronic device according to claim 11, wherein the organic compound layer containing the compound includes the compound of Formula 1 as a host, and includes another organic compound, metal or metal compound as a dopant. [12] The organic electroluminescent device of claim 9, wherein the organic electronic device comprises a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, &Lt; / RTI &gt; [Claim 17] The organic electronic device according to claim 17, wherein the organic material layer comprises a photoactive layer containing the compound of formula (1). The organic electronic device according to claim 9, wherein the organic electronic device is an organic transistor including a source, a drain, a gate, and at least one organic layer, wherein at least one of the organic layers includes the compound of the formula (1).

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