KR20190006928A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light-emitting device including the same. The compound disclosed in the present specification may be used as a material of an organic material layer of an organic light emitting device. The compound according to at least one aspect of the present invention can improve efficiency, secure low driving voltage, and/or enhance lifetime characteristics in the organic light emitting device.

Description

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

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound represented by Chemical Formula 1 and an organic light emitting device including the same.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, the electrons injected from the two electrodes and the electrons combine in the organic thin film to form a pair, and then the light is emitted while disappearing. The organic thin film may be composed of a single layer or a multilayer, if necessary.

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 light emitting layer 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 an exciton formed by recombination of holes and electrons in the light emitting layer is formed It is preferable to use a material having a high luminous efficiency for converting it into light.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

Korean Patent Publication No. 10-2006-0051619

The present invention provides a compound represented by Chemical Formula 1 and an organic light emitting device comprising the same.

An embodiment of the present invention provides a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

One of A and A 'is S or O and the other is CR5,

B and B 'is S or O and the other is CR6,

R1, R2, R5 and R6 are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group,

R 3 and R 4 are each independently a substituted or unsubstituted heterocyclic group, or they may be mutually bonded to form a heterocyclic ring.

In one embodiment of the present invention, at least one organic layer disposed between the anode and the cathode, and at least one layer of the organic layer includes a compound represented by the formula (1) Lt; / RTI >

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. The compound described in this specification can be used as a material for the hole injecting layer, the hole transporting layer, the hole injecting layer and the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer, or the electron injecting layer.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 It is.
3 to 18 are graphs showing MS spectra according to compound synthesis according to one embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

Examples of substituents herein are described below, but are not limited thereto.

The term " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; Silyl group; An alkyl group; Phosphine oxide groups; A cycloalkyl group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl dimethyl boron group, a diphenyl boron group, and a phenyl boron group.

In this specification, the amine group is -NH2; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , A diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, and a triphenylamine group, 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 60. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 60 carbon atoms. According to one embodiment, the aryl group has 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

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등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

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,

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And

And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a hetero atom and includes at least one of N, O, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a dibenzofurane group, a benzofuranyl group, a phenanthroline group, a phenanthroline group, , A thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a dibenzofuranyl group, but the present invention is not limited thereto.

In the present specification, the arylamine group means that at least one aryl group is substituted in the amine group, and the heteroarylamine group means that at least one heteroaryl group is substituted in the amine group.

In one embodiment of the present disclosure, R 1, R 2, R 5, and R 6 are each independently selected from the group consisting of hydrogen; heavy hydrogen; 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R 1, R 2, R 5 and R 6 are independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R 1, R 2, R 5 and R 6 are independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; And a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R 1, R 2, R 5 and R 6 are independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroarylamine group having 2 to 60 carbon atoms; And a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present disclosure, R 1, R 2, R 5 and R 6 are independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 heteroarylamine group; And a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present disclosure, R 1, R 2, R 5 and R 6 are independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C20 heteroarylamine group; And a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, R 1 and R 2, or R 5 and R 6 are the same or different arylamine groups substituted with at least one group selected from the group consisting of substituted or unsubstituted aryl groups and substituents represented by the following formula to be.

(2)

In one embodiment of the present specification, R 1 and R 2, or R 5 and R 6 are the same or different substituents selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 60 carbon atoms and substituents represented by the following formula Arylamine group.

In one embodiment of the present specification, R 1 and R 2, or R 5 and R 6 are the same or different substituents selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituents represented by the following formula Arylamine group.

Also, in one embodiment of the present disclosure, X is CRR ', NR ", O, S, Si, or Se.

In one embodiment of the present disclosure, X is CRR ', NR ", O, or S.

Further, in one embodiment of the present specification, a is an integer of 0 to 7.

Also in one embodiment of the present disclosure, R7 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, they may be bonded to each other to form a ring.

In one embodiment of the present disclosure, R7 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, they may be bonded to each other to form a ring.

In one embodiment of the present disclosure, R7 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; And a substituted or unsubstituted C2-C20 heterocyclic group, or when a is 2 or more, they may be bonded to adjacent groups to form a ring.

In one embodiment of the present disclosure, R7 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C30 aryl; And a substituted or unsubstituted C2-C20 heterocyclic group, or when a is 2 or more, they may be bonded to adjacent groups to form a ring.

In one embodiment of the present disclosure, R, R 'and R " are each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, and R and R 'may be bonded to each other to form a ring.

Further, in one embodiment of the present disclosure, R, R 'and R " are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, and R and R 'may be bonded to each other to form a ring.

Further, in one embodiment of the present disclosure, R, R 'and R " are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; And a substituted or unsubstituted aryl group, and R and R 'may be bonded to each other to form a ring.

Further, in one embodiment of the present specification, R, R 'and R "are each independently a substituted or unsubstituted alkyl group; And a substituted or unsubstituted aryl group, and R and R 'may be bonded to each other to form a ring.

Further, in one embodiment of the present specification, R, R 'and R "are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; And a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R and R 'may be bonded to each other to form a ring.

Further, in one embodiment of the present specification, R, R 'and R "are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; And a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and R and R 'may be bonded to each other to form a ring.

In one embodiment of the present invention, the substituent represented by the general formula (2) is any one of the following general formulas (2-1) to (2-8).

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

[Chemical Formula 2-7]

[Chemical Formula 2-8]

In the general formulas (2-1) to (2-8)

R " is as defined above,

R8 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group,

b is an integer of 0 to 4,

c is an integer of 0 to 6,

When b or c is 2 or more, R8 is the same or different.

Also in one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

Also in one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group.

Also in one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; And a substituted or unsubstituted aryl group.

Also in one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; And a substituted or unsubstituted C6 to C60 aryl group.

Also in one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; And a substituted or unsubstituted C6 to C30 aryl group.

Further, in one embodiment of the present invention, the substituent represented by Formula 2 is any one of the following structures.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following Structures 1-1 to 1-72.

In the above Structures 1-1 to 1-72, R1 and R2 may be independently selected from the following 2-1 to 2-133.

According to one embodiment of the present invention, R 1 and R 2 are each independently an arylamine group or a heteroarylamine group, and the aryl or heteroaryl group of the arylamine group and the heteroarylamine group is represented by the following formulas 2-1 to 2- -133. ≪ / RTI >

The compound according to one embodiment of the present specification can be produced by a production method described below.

For example, the compound of Formula 1 can be prepared as a core structure as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

[Reaction Scheme 1]

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.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to 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 light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Also, an organic light emitting device according to the present invention is an organic light emitting device comprising a cathode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein at least one of the organic layers includes the compound do.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

The compound may be formed into an organic material 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 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.

In the organic light emitting device of the present invention, the organic material layer may include at least one of an electron transporting layer, an electron injecting layer, and a layer simultaneously performing electron injection and electron transporting, and at least one of the layers may be represented by Formula 1 ≪ / RTI > compounds.

In the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, and at least one of the layers may be represented by Formula 1 ≪ / RTI > compounds.

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1). As one example, the compound represented by Formula 1 may be included as a dopant in the light emitting layer.

As another example, the organic compound layer containing the compound represented by the formula (1) may include a compound represented by the formula (1) as a dopant, and may include a fluorescent host or a phosphorescent host.

In another embodiment, the organic material layer containing the compound represented by the formula (1) contains the compound represented by the formula (1) as a dopant and includes a fluorescent host or a phosphorescent host, As a dopant.

As another example, the organic material layer containing the compound represented by Formula 1 may include a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant. have.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, or the electron transporting layer 7.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

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); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as poly (3-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (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 LiO2 / 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 porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, 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 layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. 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 (Alq3); 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.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The iridium complex used as a dopant in the light emitting layer is as follows but is not limited thereto.

[Ir (piq) 3] [Btp2Ir (acac)]

[Ir (ppy) 3] [Ir (ppy) 2 (acac)]

[Ir (mpyp) 3] [F2Irpic]

[(F2ppy) 2Ir (tmd)] [Ir (dfppz) 3]

　　　

　　　

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 Alq3; 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 compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, but the scope of the present invention is not limited thereto.

< Manufacturing example  1> Of H  synthesis

1-1) Synthesis of Compound A

2.5 M n-butyllithium (61.3 mL, 153.3 mmol) was dissolved in anhydrous diethyl ether (50 mL) at -78 ° C and a solution of 3-bromofuran (22.5 g, 153.3 mmol) was slowly added dropwise, followed by stirring for 3 hours. Furan-3-carbaldehyde (14.7 g, 153.3 mmol) was added slowly at -78 deg. C, and the mixture was stirred for 30 minutes, then was stirred at room temperature and stirred for 30 minutes. The mixture was cooled to -23 DEG C again, and 2.5 M n-butyl lithium (122.6 mL, 306.6 mmol) was added dropwise. The mixture was stirred again for 2 hours, isothermalized at room temperature and stirred for 30 minutes. Iodine (116.7 g, 459.9 mmol) was dissolved in ether, slowly added dropwise, and stirred for 24 hours. The mixture was adjusted to pH 6 with a 1N hydrochloric acid aqueous solution and a sodium sulfite aqueous solution, extracted with ether (100 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography (silica gel; ethyl acetate / hexane = 1/9 (v: v)) to give compound A (25 g, 36.4%).

1-2) Synthesis of compound B

The compound A (23.2 g, 55.8 mmol) prepared in the above 1-1) was dissolved in chloroform (50 mL), pyridinium chlorochromate (PCC, 18 g, 83.7 mmol) was added and stirred at room temperature for 12 hours Respectively. Thereafter, the mixture was concentrated under reduced pressure, and the concentrated mixture was purified by column chromatography (silica gel; ethyl acetate / hexane = 1/8 (v: v)) to obtain compound B (18.5 g, 80%).

1-3) Synthesis of Compound C

The compound B (7.7 g, 20.6 mmol) prepared in 1-2) above was dissolved in anhydrous dimethylformamide (DMF, 50 mL) and stirred. Then copper powder (3.92 g, 61.8 mmol) And refluxed for 24 hours. The refluxed mixture was cooled to room temperature, filtered, added with distilled water (10 ml), and then extracted with ether (20 ml). The extracted organic layer was concentrated under reduced pressure, and the concentrated mixture was purified by column chromatography (silica gel; ethyl acetate / hexane = 1/9 (v: v)) to obtain compound C (3 g, 76.6%).

1-4) Synthesis of Compound D

Compound C (2.53 g, 15.8 mmol) prepared in 1-3) above and potassium hydroxide (3.02 g, 53.8 mmol) were dissolved in triethylene glycol (200 mL), and 80% hydrazine hydrate ) Was added, and the mixture was heated to 180 DEG C and stirred for 24 hours. After that, it was cooled to room temperature, filtered, and distilled water (30 mL) was added. The mixture was extracted with ether (100 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography (silica gel; ethyl acetate / hexane = 1/20 (v: v)) to give compound D (1.31 g, 56.7%).

1-5) Synthesis of Compound E

Compound E was synthesized by the same method as in 1-1) above using 3-bromothiophene and thiophene-3-carbaldehyde.

1-6) Synthesis of Compound F

Compound F was synthesized by the same method as 1-2) above using Compound E prepared in 1-5) above.

1-7) Synthesis of Compound G

Compound G was synthesized in the same manner as in 1-3) above using Compound F prepared in 1-6) above.

1-8) Synthesis of Compound H

Compound H was synthesized by using the compound G prepared in the above 1-7) in the same manner as in 1-4) above.

< Manufacturing example  2> Synthesis of compounds I to AB

2-1) Synthesis of Compound (I)

Compound D (10.0 g, 68.4 mmol), 4-bromopyridine (27.0 g, 171 mmol) and sodium glutaraldehyde (32.9 g, 342 mmol) were dissolved in toluene (300 mL) and refluxed. 383 mg (1.37 mmol) of tricyclohexylphosphine (Pd (dba) 2) and tricyclohexylphosphine (383 mg, 1.37 mmol) were dissolved in 30 mL of toluene, and the mixture was stirred for 30 minutes Respectively. After refluxing for 24 hours, distilled water (100 mL) was added to the mixture, extracted with methylene chloride (MC, 300 mL), and the extracted organic layer was concentrated under reduced pressure. The concentrated mixture was purified by column chromatography to give compound I (16.6 g, 81%).

2-2) Synthesis of Compound J

Compound H was synthesized in the same manner as in 2-1) above.

2-3) Synthesis of Compound K

Compound I (2 g, 6.66 mmol) was dissolved in 100 mL of chloroform, and a solution of bromine (2.2 g, 13.98 mmol) in chloroform (50 mL) was added slowly. And stirred at room temperature for 12 hours. Methanol was added to the reaction solution, and the precipitated solid was filtered to obtain Compound K (2.6 g, 85%).

2-4) Synthesis of Compound L

Compound J was used to synthesize compound L in the same manner as in 2-3) above.

2-5) Synthesis of Compound (M)

Compound M was obtained in the same manner as in 2-1) except that 5-bromopyrimidine was used instead of 4-bromopyridine.

2-6) Synthesis of Compound N

Compound H was synthesized in the same manner as in 2-5) above.

2-7) Synthesis of Compound O and P

Compounds O and P were synthesized in the same manner as in 2-3) above using compounds M and N, respectively.

2-8) Synthesis of Compound Q

9- (2-bromophenyl) carbazole (15 g, 46.5 mmol) was dissolved in tetrahydrofuran (THF, 200 mL) and cooled to -78 deg. To the solution was slowly added dropwise 2.5 M n-butyl lithium (16.8 mL, 41.9 mmol), and the mixture was stirred for 1 hour. Compound C (5.70 g, 35.6 mmol) was added to the solution, and the mixture was stirred for 1 hour, then isothermalized at room temperature, and stirred for 2 hours. The mixture was neutralized with a 1N ammonium chloride solution (300 mL), extracted with chloroform (300 mL), and the organic layer was concentrated under reduced pressure. The concentrated mixture was recrystallized from toluene and hexane to obtain Compound Q (12.5 g, 87%).

2-9) Synthesis of Compound R

Compound G was used to synthesize compound R in the same manner as in 2-8) above.

2-10) Synthesis of Compound S

Compound Q (10 g, 24.8 mmol) was dissolved in acetic acid (100 mL) and sulfuric acid (2 mL) was added. The solution was refluxed for 2 hours and toluene (300 mL) was added. The mixture was neutralized with a saturated sodium carbonate solution, and the organic layer was separated and concentrated under reduced pressure. The concentrated mixture was recrystallized from toluene and hexane to obtain compound S (9.27 g, 97%).

2-11) Synthesis of Compound T

Compound R was used to synthesize compound T in the same manner as in 2-10).

2-12) Synthesis of Compound U and V

Compounds U and V were synthesized in the same manner as in 2-3) above using compounds S and T, respectively.

2-13) Synthesis of Compound W

Compound W was obtained in the same manner as in 2-8) except that 10- (2-bromophenyl) phenoxazine was used instead of 9- (2-bromophenyl) carbazole.

2-14) Synthesis of Compound X

Compound X was synthesized by using the compound G in the same manner as 2-13) above.

2-15) Synthesis of Compound Y and Z

Compounds Y and Z were synthesized in the same manner as in 2-10) above using compounds W and X, respectively.

2-16) Synthesis of Compound AA and AB

Compounds AA and AB were synthesized in the same manner as in 2-3) above using compounds Y and Z, respectively.

PREPARATION EXAMPLE 3 Synthesis of Synthesis Examples 1 to 16

3-1) Synthesis of Synthesis Example 1

Amine (5.57 g, 18 mmol) and sodium tertiary butoxide (tBuONa, 1.45 g, 15 mmol) were dissolved in a solution of compound K (2.75 g, 6.0 mmol) and N- (naphthalen-2-yl) dibenzofuran- (30 mg, 0.06 mmol) was added to the solution, and the mixture was stirred under reflux for 6 hours. After cooling to room temperature, water was added and extracted with toluene (200 mL). Dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain Compound 1 (4.5 g, 82%). ([M &lt; + &gt;] = 915)

FIG. 3 is a graph showing the MS spectrum of Compound 1 above. FIG.

3-2) Synthesis of Synthesis Example 2

Compound 2 was synthesized in the same manner as in 3-1) above using compound K and 6- (tert-butyl) -N- (4- (tertiarybutyl) phenyl) dibenzofuran-4-amine. ([M &lt; + &gt;] = 1039)

FIG. 4 is a graph showing the MS spectrum of the compound 2. FIG.

3-3) Synthesis of Synthesis Example 3

Compound 3 was synthesized in the same manner as in 3-1) above using compound K and N- (4-isopropylphenyl) benzene-d5-amine. ([M &lt; + &gt;] = 729)

FIG. 5 is a graph showing the MS spectrum of the compound 3. FIG.

3-4) Synthesis of Synthesis Example 4

Compound 4 was synthesized in the same manner as in 3-1) above using the compound L and N- (4-isopropylphenyl) dibenzothiophen-1-amine. ([M &lt; + &gt;] = 963)

FIG. 6 is a graph showing the MS spectrum of the compound 4. FIG.

3-5) Synthesis of Synthesis Example 5

Compound 5 was synthesized by the same method as in 3-1) above using compound L and N - ([1,1'-biphenyl] 4-yl) -9,9'-dimethylfluorene-2-amine. ([M &lt; + &gt;] = 1051)

7 is a graph showing the MS spectrum of the compound 5.

3-6) Synthesis of Synthesis Example 6

Compound 6 was synthesized by the same method as in 3-1) above using compound O and N- (4-tert-butylphenyl) benzene-d5-amine. ([M &lt; + &gt;] = 759)

8 is a graph showing the MS spectrum of Compound 6 above.

3-7) Synthesis of Synthesis Example 7

Compound 7 was synthesized in the same manner as in 3-1) above using compound O and N- (o-tolyl) - [1,1'-biphenyl] -4-amine. ([M &lt; + &gt;] = 817)

FIG. 9 is a graph showing the MS spectrum of the compound 7. FIG.

3-8) Synthesis of Synthesis Example 8

Compound 8 was synthesized by using the compound P and diphenylamine in the same manner as in 3-1). ([M &lt; + &gt;] = 669)

10 is a graph showing the MS spectrum of Compound 8 above.

3-9) Synthesis of Synthesis Example 9

Compound 9 was synthesized in the same manner as in 3-1) above, using compound P and 9-phenyl-N- (phenyl-d5) -9H-carbazol-2-amine. ([M &lt; + &gt;] = 1009)

11 is a graph showing the MS spectrum of Compound 9 above.

3-10) Synthesis of Synthesis Example 10

Compound 10 was synthesized in the same manner as in 3-1) above using compound U and di ([1,1'-biphenyl] -2-yl) amine. ([M &lt; + &gt;] = 1024)

12 is a graph showing the MS spectrum of Compound 10 above.

3-11) Synthesis of Synthesis Example 11

Compound 11 was synthesized by the same method as in 3-1) above using compound U and 4- (naphthalen-2-ylamino) benzonitrile. ([M &lt; + &gt;] = 870)

13 is a graph showing the MS spectrum of the compound 11.

3-12) Synthesis of Synthesis Example 12

Compound 12 was synthesized by the same method as in 3-1) above using compound U and 2-methyl-N-phenylaniline. ([M &lt; + &gt;] = 748)

14 is a graph showing the MS spectrum of the compound 12.

3-13) Synthesis of Synthesis Example 13

Compound 13 was synthesized in the same manner as in 3-1) above using Compound V and N- (6-fluoronaphthalen-2-yl) dibenzothiophen-1-amine. ([M &lt; + &gt;] = 1100)

15 is a graph showing the MS spectrum of the compound 13.

3-14) Synthesis of Synthesis Example 14

Compound 14 was synthesized in the same manner as in 3-1) above using Compound V and N- (4- (trimethylsilyl) phenyl) naphthalen-1-amine. ([M &lt; + &gt;] = 996)

16 is a graph showing the MS spectrum of the compound 14.

3-15) Synthesis of Synthesis Example 15

Compound 15 was synthesized by the same method as in 3-1) above using compound AA and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. ([M &lt; + &gt;] = 968)

17 is a graph showing the MS spectrum of the compound 15.

3-16) Synthesis of Synthesis Example 16

Compound 16 was synthesized in the same manner as in 3-1) above using compound AB and N- (naphthalen-1-yl) fluoranthene-3-amine. ([M &lt; + &gt;] = 1116)

18 is a graph showing the MS spectrum of the compound 16.

&Lt; Preparation Example 4 > Preparation of Comparative Examples and Examples

4-1) Preparation of Comparative Example 1

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. 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. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. 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.

(HAT)

(HAT)

4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 Å) of the following formula, which is a hole transporting material, was vacuum deposited on the hole injection layer to form a hole transport layer .

(NPB)

(NPB)

Subsequently, 9- (naphthalene-1-yl) -10- (naphthalen-2-yl) anthracene (BH1) of the following formula was vacuum deposited on the hole transport layer to a thickness of 300 Å as a light emitting layer host to form a light emitting layer.

(BH)

(BH)

4% by weight of Compound N4, N9-bis (dibenzofuran-4-yl) -N4 and N9-di-m-tolylpyrene-4,9-diamine (BD1) was used as a blue light emitting dopant, Respectively.

(BD1)

(BD1)

Alq3 (aluminum tris (8-hydroxyquinoline)) of the following chemical formula was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

(Alq3)

(Alq3)

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å on the electron injection and transport layer sequentially to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. -7 to 5 x 10 &lt; -8 &gt; torr.

The performance of the thus fabricated device was measured.

4-2) Preparation of Comparative Examples 2 to 3

As a blue light emitting layer dopant material, N2, N2, N6, N6-tetrakis (4-tertiary butylphenyl) -4,4-dimethylcyclopenta [2,1-b: 3,4- 2,4,6-diamine (BD2) or N2, N2, N6, N6-tetraphenyl spiro [cyclopenta [2,1-b: 3,4-b '] dithiophen- 2,6-diamine (BD3) was used in place of 2,6-diamine (BD3), and the device performance was measured.

(BD3) (BD2)

4-3) Preparation of Examples 1 to 16

The device performance was measured in the same manner as in Comparative Example 1, except that the compounds 1 to 12 were used instead of BD1 as the blue light emitting layer dopant material.

Table 1 shows the results of an experiment in which the organic light emitting device was manufactured using each compound as a blue dopant material at the current density of 20 mA / cm ² as in Comparative Examples 1 to 3 and Examples 1 to 12.

Experimental Example Dopant material Voltage (V) Efficiency (Cd / A) Color coordinate CIE_y Lifetime T97% (hours) Comparative Example 1 BD1 5.29 5.75 0.046 110 Comparative Example 2 BD2 5.21 5.72 0.052 101 Comparative Example 3 BD3 5.12 5.48 0.049 76 Example 1 Synthesis Example 1 5.14 6.58 0.052 141 Example 2 Synthesis Example 2 5.10 6.81 0.050 135 Example 3 Synthesis Example 3 5.14 6.51 0.051 152 Example 4 Synthesis Example 4 5.08 6.89 0.048 92 Example 5 Synthesis Example 5 5.11 6.70 0.050 99 Example 6 Synthesis Example 6 5.08 6.73 0.049 149 Example 7 Synthesis Example 7 5.09 6.76 0.049 140 Example 8 Synthesis Example 8 5.11 6.03 0.053 82 Example 9 Synthesis Example 9 5.12 6.58 0.053 93 Example 10 Synthesis Example 10 5.13 6.83 0.046 147 Example 11 Synthesis Example 11 5.09 6.65 0.047 139 Example 12 Synthesis Example 12 5.11 6.40 0.048 140 Example 13 Synthesis Example 13 5.08 6.79 0.048 97 Example 14 Synthesis Example 14 5.10 6.79 0.049 89 Example 15 Synthesis Example 15 5.09 6.71 0.051 145 Example 16 Synthesis Example 16 5.08 6.89 0.052 103

As can be seen from the above table, the compounds according to the present invention show excellent device characteristics.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (8)

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

In Formula 1,
One of A and A 'is S or O and the other is CR5,
B and B 'is S or O and the other is CR6,
R1, R2, R5 and R6 are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron 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 aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group,
R3 and R4 are each independently a substituted or unsubstituted heterocyclic group, or they may be mutually bonded to form a heterocyclic ring. The method according to claim 1,
R1 and R2, or R5 and R6 are arylamine groups substituted with at least one selected from the group consisting of substituted or unsubstituted aryl groups and substituents represented by the following formula (2)
(2)

X is CRR &apos;, NR &quot;, O, S or Se,
a is an integer of 0 to 7,
when a is 2 or more, R &lt; 7 &gt; are the same or different from each other,
R7 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or when a is 2 or more, they may be bonded to adjacent groups to form a substituted or unsubstituted ring,
R, R 'and R &quot; are each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group,
R and R 'may combine with each other to form a ring. The method of claim 2,
Wherein the substituent represented by the general formula (2) is any one of the following general formulas (2-1) to (2-8):
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

[Chemical Formula 2-7]

[Chemical Formula 2-8]

In the general formulas (2-1) to (2-8)
R &quot; is as defined in claim 2,
R8 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group,
b is an integer of 0 to 4,
c is an integer of 0 to 6,
When b or c is 2 or more, R8 is the same or different. The method of claim 2,
Wherein the substituent represented by the general formula (2) is any one of the following structures:

. An organic light emitting device comprising: an anode; a cathode; and at least one organic layer disposed between the anode and the cathode, wherein at least one of the organic layers includes a compound according to any one of claims 1 to 4. The method of claim 5,
Wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound of the formula (1). The method of claim 5,
Wherein the organic material layer comprises an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound of the formula (1). The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1.

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