KR20150022521A - Compound, organic optoelectric device and display device - Google Patents

Abstract

Provided is a compound providing an organic optoelectric device having characteristics such as high efficiency and long life. The present invention relates to a compound represented by chemical formula 1, an organic optoelectric device including the same, and a display device including the organic optoelectric device. (Here, definitions of X^1 to X^8 are defined as same as the specification.)

Description

TECHNICAL FIELD [0001] The present invention relates to a compound, an organic optoelectronic device including the same, and a display device.

Organic optoelectronic devices, and display devices.

Organic optoelectronic devices are devices that can switch between electrical and optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, And a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic layer is highly affected by the organic material contained in the organic layer.

In particular, in order for the organic light emitting device to be applied to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing the electrochemical stability.

High efficiency, long life, and the like.

An organic optoelectronic device including the compound, and a display device including the organic optoelectronic device.

In one embodiment of the present invention, there is provided a compound represented by the following formula (1).

 [Chemical Formula 1]

In Formula 1,

X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)

At least one of X ¹ and X ² is NL ¹ -R ^a ,

X ³ to X ⁸ are each independently N or CL ² -R ^b ,

R ¹ , R ² , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocyclo An alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 alkoxycarbonyl groups, C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

R ¹ and R ² are each independently present or fused together to form a ring,

R ^b is independently present, or two adjacent R ^b are fused to form a ring,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, An unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C6 to C30 heteroarylene amine group, A substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, It is a combination of these.

Another embodiment of the present invention provides an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer includes the compound.

In another embodiment of the present invention, there is provided a display device including the above-described organic optoelectronic device.

A high-efficiency, long-life organic optoelectronic device can be realized.

1 and 2 are cross-sectional views illustrating various embodiments of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, C1 to C10 alkyl groups such as a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, A trifluoroalkyl group or a cyano group.

Means one to three heteroatoms selected from the group consisting of N, O, S and P in one functional group, and the remainder is carbon, unless otherwise defined.

In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an alkyl group having from 1 to 20 carbon atoms. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

The term "aryl group" used herein means a substituent in which all the elements of the cyclic substituent have p-orbital and the p-orbital forms a conjugation, and the monocyclic or fused-ring polycyclic (I. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heteroaryl group "means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted thienyl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, Substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, A substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted naphthyridinyl group, A substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, A phenyl group, or a combination thereof.

As used herein, the term "single bond" in the context of the definition of an intermediate linkage means a bond that is directly connected to a carbon or carbon atom other than a carbon or heteroatom other than carbon. Specifically, L means a single bond, Is directly connected to the center core. That is, in the present specification, a single bond does not mean methylene or the like via carbon.

In the present specification, the hole property means a property of facilitating the injection into the light emitting layer and the movement in the light emitting layer of the hole formed in the anode due to conduction characteristics along the HOMO level. Specifically, it may be similar to the characteristic of pushing electrons. More specifically, it is similar to the ability to give electrons when an electric field is applied.

Further, the electron characteristic means a property of facilitating the injection of electrons formed in the anode into the luminescent layer and the movement in the luminescent layer due to conduction characteristics along the LUMO level. Specifically, it may be similar to the characteristic of attracting electrons. More specifically, it is analogous to the ability to receive electrons when an electric field is applied.

Hereinafter, the compounds according to one embodiment will be described.

In one embodiment of the present invention, a compound represented by the following general formula (1) can be provided.

[Chemical Formula 1]

In Formula 1,

X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)

At least one of X ¹ and X ² is NL ¹ -R ^a ,

X ³ to X ⁸ are each independently N or CL ² -R ^b ,

R ¹ , R ² , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocyclo An alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 alkoxycarbonyl groups, C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

R ¹ and R ² are each independently present or fused together to form a ring,

R ^b is independently present, or two adjacent R ^b are fused to form a ring,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, An unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C6 to C30 heteroarylene amine group, A substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, It is a combination of these.

The compound according to an embodiment of the present invention contains aromatic nitrogen (N), thereby enhancing the electron characteristics and introducing a substituent having a hole characteristic, so that the compound has an amphoteric characteristic. As a result, it has appropriate T1 value and excellent thermal stability, so that it can have high efficiency, long life, and low voltage driving characteristics.

By including the aromatic nitrogen (N), the deposition temperature can be lowered and the thermal stability can be improved by reducing the molecular stacking between adjacent compounds. Accordingly, the deposition process of the compound can be performed at a relatively low temperature, thereby improving the processability and preventing the compound from being deteriorated by heat generated during the process or driving the device to which the compound is applied. Therefore, the lifetime of the compound and the device to which the compound is applied can be improved.

Specifically, the compound according to an embodiment of the present invention is such that all of X ³ to X ⁸ are CL ² -R ^b, or one of X ³ to X ⁸ is N.

For example, it may be represented by any one of the following formulas (2) to (5).

[Chemical Formula 2] < EMI ID =

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[Chemical Formula 4]

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In the above formulas 2 to 5,

X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)

At least one of X ¹ and X ² is NL ¹ -R ^a ,

R ¹ , R ² , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocyclo An alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 alkoxycarbonyl groups, C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof.

For example, the compound according to one embodiment of the present invention may be represented by any one of the following formulas (6) to (38).

[Chemical Formula 7] [Chemical Formula 8] Chemical Formula 9 [Chemical Formula 10]

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[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]

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[Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]

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[Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

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[Chemical Formula 25] [Chemical Formula 25]

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[Chemical Formula 30] [Chemical Formula 30]

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[Chemical Formula 32] [Chemical Formula 32]

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[Chemical Formula 37] [Chemical Formula 38]

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In the above Chemical Formulas 6 to 38,

X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)

At least one of X ¹ and X ² is NL ¹ -R ^a ,

R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, ego,

L ¹ is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof.

And may be represented by any one of the following formulas (39) to (42).

[Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]

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In the above formulas (39) to (42)

X ³ to X ⁸ are each independently N or CL ² -R ^b ,

R ¹ and R ² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heteroaryl group, Forming a ring,

R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, Substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted C3 to C40 silyloxy groups, substituted or unsubstituted C1 to C30 acyl groups, substituted or unsubstituted C1 to C20 acyloxy groups, substituted or unsubstituted C1 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof.

R ¹ and R ² in Formula 40 or Formula 41 may be fused to each other to form Formula 43 or 44, respectively.

[Chemical Formula 43]

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In the above formula (43) or (44)

X ³ to X ⁸ are each independently N or CL ² -R ^b ,

R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, Substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted C3 to C40 silyloxy groups, substituted or unsubstituted C1 to C30 acyl groups, substituted or unsubstituted C1 to C20 acyloxy groups, substituted or unsubstituted C1 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group.

In the above formula (1), the conjugation length of the entire compound can be determined by selectively controlling the L ¹ , and the triplet energy bandgap can be controlled therefrom. This makes it possible to realize the characteristics of the materials required in organic optoelectronic devices. Further, the triplet energy bandgap can be controlled by changing the bonding positions of ortho, para, and meta.

Specific examples of the L ¹ include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted p-terphenylene group, a substituted or unsubstituted m-terphenylene group, a substituted or unsubstituted Substituted or unsubstituted naphthylene group, substituted or unsubstituted anthracenylene group, substituted or unsubstituted phenanthrylene group, substituted or unsubstituted pyrenylene group, or substituted or unsubstituted fluorene group, Oleylene group and the like.

More specifically, examples of the substituted or unsubstituted phenylene group include groups represented by the following formulas S-1, S-2, and S-3.

[Formula S-1] [Formula S-2] [Formula S-3]

More specifically, examples of the substituted or unsubstituted biphenylene group include groups represented by the following formulas S-4, S-5, and S-6.

[Formula S-4] [Formula S-5] [Formula S-6]

For example, it can be represented by any one of the following formulas (45) to (55).

[Chemical Formula 48] [Chemical Formula 47] [Chemical Formula 48]

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[Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52]

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[Chemical Formula 55] [Chemical Formula 55]

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In Formulas 45 to 55,

X ² is NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S═O), SO ₂ (O═S═O)

X ³ to X ⁸ are each independently N or CL ² -R ^b ,

R ¹ and R ² are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, Or fused together to form a ring,

R ^a and R ^b are each independently present, or two adjacent R ^b are fused to form a ring,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group.

The compound represented by Formula 1 may be designed to have desired characteristics by introducing various substituents. For example, when R ^a or R ^b in the formula (1) is ^a substituent having a hole property, the compound may be designed as a compound having both ampholytic characteristics by including both a part having an electron characteristic and a part having a hole characteristic, When R &^lt; a & gt ^; or R < ^b > in the general formula (1) is ^a functional group having an electron characteristic, the compound can be designed as a compound having a strong electronic characteristic.

By using a compound having an appropriate energy level according to the substituent of the compound in an organic optoelectronic device, the hole transporting ability or the electron transporting ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent electrochemical and thermal stability. The lifetime characteristics can be improved when the device is driven.

For example, R & lt ^{; a} & gt ^; and R < ^b & gt ^; may each independently be any of the substituted or unsubstituted functional groups listed in Group I below.

[Group I]

In the group I,

Z are each independently N or CR ^c,

W is O, S, SO, SO ₂ , NR ^d , CR ^e R ^f , or SiR ^g R ^h ,

Wherein R ^c to R ^h are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl An amino group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonyl An amino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C20 acyl group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A halogen atom, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a perorenyl group or a substituted or unsubstituted C1 to C30 heteroarylthiol group Lt; / RTI &

* Is a connecting point and may be located in any of the elements forming the functional group.

Specifically, it may be one of the substituted or unsubstituted functional groups listed in Group II below.

[Group II]

In the group II,

R 'and R "are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a substituted or unsubstituted silyl group ,

* Is the connection point.

Most specifically, it may be one of the substituted or unsubstituted functional groups listed in Group III below.

[Group III]

In the group III,

* Is the connection point.

Specific examples of the compound according to one embodiment of the present invention include, but are not limited to, the compounds listed below.

Hereinafter, an organic optoelectronic device to which the above-described compound is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic optoelectronic device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al and BaF ₂ / Ca.

The organic layer 105 includes the light emitting layer 130 including the above-described compound.

The light-emitting layer 130 may include, for example, the above-described compounds alone or may be a mixture of at least two of the above-described compounds, or may include a mixture of the above-described compounds and other compounds. When the above-mentioned compound is mixed with another compound, it may be contained in the form of, for example, a host and a dopant, and the above-mentioned compound may be included, for example, as a host. The host may be, for example, a phosphorescent host or a fluorescent host, for example, a phosphorescent host.

When the above-mentioned compound is included as a host, the dopant may be an inorganic, organic, or organic compound and may be selected from among known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole assist layer 140 in addition to the light emitting layer 230. The hole assist layer 140 can further enhance the hole injection and / or hole mobility between the anode 120 and the light emitting layer 230 and block the electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The above-described compounds may be included in the light emitting layer 230 and / or the hole assist layer 140.

  The organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an auxiliary electron transport layer, a hole transport layer, an auxiliary hole transport layer, a hole injection layer, or a combination layer thereof, though not shown. The compounds of the present invention may be included in these organic layers. The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The organic light emitting device described above can be applied to an organic light emitting display.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

(Preparation of compound for organic optoelectronic device)

Synthetic example  1: Compound NN Synthesis of -1-1

The compound NN-1-1 shown as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through the route shown in the following Reaction Scheme 1.

[Reaction Scheme 1]

A first step; Synthesis of intermediate product (A1)

Bromo-2-nitrobenzene (115.13 g, 284.96 mmol), Cu (21.73 g, 341.95 mmol) and DMF (2300 mL) were charged under a nitrogen stream and refluxed for 12 hours. After completion of the reaction, the reaction mixture was diluted with ethylacetate (3000 mL) and washed three times with purified water (2500 mL). Water was removed from the organic layer with 250 g of magnesium sulfate, the solvent was removed, and the residue was purified by column chromatography to obtain A1 (52.19 g, yield 75%).

A second step; Synthesis of intermediate product (B1)

Intermediate A1 (52.19 g, 213.72 mmol), triphenylphosphine (560.6 g, 2137.2 mmol) and orthodichlorobenzene (1000 mL) were introduced and refluxed for 12 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (1000 mL) and washed three times with purified water (1000 mL). Water was removed from the organic layer with magnesium sulfate (100 g), the solvent was removed, and the residue was purified by column chromatography to obtain B1 (21.18 g, yield 55%).

A third step; Intermediate product ( C1 ) Synthesis of

(12.1 g, 58.77 mmol), tris (dibenzylideneacetone) dipalladium (0) (3.23 g, 3.53 mmol), potassium carbonate (17.87 g, 129.3 mmol), Intermediate B1 (21.18 g, 117.55 mmol), iodobenzene , Tri-tert-butylphosphine (2.14 g, 10.58 mmol) and toluene (450 mL), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was washed three times with purified water (450 mL), and water was removed with magnesium sulfate (45 g). The solvent was removed, and the residue was purified by column chromatography to obtain C1 (21.99 g, yield 73%).

Step 4; compound NN Synthesis of -1-1

A solution of intermediate C1 (1.98 g, 7.72 mmol), M1 (3.59 g, 11.58 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.21 g, 0.23 mmol), potassium carbonate (1.17 g, 8.49 mmol) -Tart-butylphosphine (0.14 g, 0.70 mmol) and toluene (40 mL) were charged and refluxed for 12 hours. After completion of the reaction, the reaction mixture was washed three times with purified water (40 mL), and water was removed with magnesium sulfate (4 g). The solvent was removed and the residue was purified by column chromatography to obtain NN-1-1 (1.8 g, yield 48%).

MS (MALDI-TOF): m / z 485.19 [M] ^< ^{+ &}

Synthetic example  2: Compound NN Synthesis of -1-2

Compound NN-1-2 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that in the fourth step of Synthesis Example 1, M2 was used instead of M1.

Synthetic example  3: Compound NN Synthesis of -1-3

Compound NN-1-3 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M3 was used in place of Ml in the fourth step of Synthesis Example 1.

Synthetic example  4: Compound NN Synthesis of -1-4

Compound NN-1-4 was synthesized through Reaction Scheme 1 in the same manner as in Synthesis Example 1, except that M4 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  5: Compound NN Synthesis of -1-5

Compound NN-1-5 was synthesized through Reaction Scheme 1 in the same manner as in Synthesis Example 1, except that M5 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  6: Compound NN Synthesis of -1-6

Compound NN-1-6 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M6 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  7: Compound NN Synthesis of -1-7

Compound NN-1-7 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M7 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  8: Compound NN Synthesis of -1-8

Compound NN-1-8 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M8 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  9: Compound NN Synthesis of -1-9

Compound NN-1-9 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M9 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  10: Compound NN Synthesis of -1-10

Compound NN-1-10 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M10 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  11: Compound NN Synthesis of -1-11

Compound NN-1-11 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M11 was used instead of Ml in the fourth step of Synthesis Example 1. [

Synthetic example  12: Compound NN Synthesis of -1-12

Compound NN-1-12 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M12 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  13: Compound NN Synthesis of -1-13

Compound NN-1-13 was synthesized through Reaction Scheme 1 in the same manner as in Synthesis Example 1, except that M13 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  14: Compound NN Synthesis of -1-14

Compound NN-1-14 was synthesized through the reaction scheme 1 in the same manner as in Synthesis Example 1, except that M14 was used instead of Ml in the fourth step of Synthesis Example 1.

Synthetic example  15: Compound NN Synthesis of -1-15

Compound NN-1-15 was synthesized through Reaction Scheme 1 in the same manner as in Synthesis Example 1, except that M15 was used instead of Ml in the fourth step of Synthesis Example 1.

Specific compounds according to one embodiment of the present invention prepared according to the above synthesis method are shown in Table 1 below.

Intermediate product C Reactant M compound yield(%) MS [M] ^< ^{+ &}

C1

M-1

NN-1-1 48 485.58 M-2

NN-1-2 35 485.58 M-3

NN-1-3 74 561.67 M-4

NN-1-4 70 561.67 M-5

NN-1-5 68 561.67 M-6

NN-1-5 69 561.67 M-7

NN-1-7 46 486.57 M-8

NN-1-8 52 486.57 M-9

NN-1-9 68 562.66 M-10

NN-1-10 72 562.66 M-11

NN-1-11 70 562.66 M-12

NN-1-12 66 562.66 M-13

NN-1-13 48 487.55 M-14

NN-1-14 74 563.65 M-15

NN-1-15 72 563.65

Synthetic example  16: Compound NN Synthesis of -2-1

Compound NN-2-1 shown as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through the route shown in the following Reaction Scheme 2.

[Reaction Scheme 2]

A first step; Intermediate product ( D1 ) Synthesis of

M3 (15.19 g, 22.23 mmol) and THF (300 mL) were charged under a nitrogen stream, and the mixture was cooled and stirred at -78 ° C. Slowly inject n-BuLi (2.5 M in n-Hexane, 10.67 mL, 26.67 mmol) at -78 ° C. After stirring at -78 ° C for 1 hour, triisopropylborate (5.02 g, 26.67 mmol) was slowly added. After the injection, the temperature is raised to room temperature and stirred. After stirring for 1 hour, cool to 0 캜 and slowly inject 2N HCl aqueous solution (80 mL). After stirring for 1 hour, the mixture was extracted with ethyl acetate (300 mL) and washed three times with purified water (300 mL). Water was removed from the organic layer with 30 g of magnesium sulfate, and the solvent was removed, followed by purification by column chromatography to obtain D1 (5.62 g, yield 72%).

A second step; Intermediate product ( E1 ) Synthesis of

A mixture of intermediate D1 (5.62 g, 16.00 mmol), 2-bromo-l, 3-dinitrobenzene (4.74 g, 19.20 mmol), tetrakistriphenylphosphine palladium (0) (0.37 g, 0.32 mmol) Carbonitrile (4.42 g, 32.00 mmol), toluene (84 mL) and purified water (28 mL) were added together and refluxed for 12 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 mL) and washed three times with purified water (200 mL). Water was removed from the organic layer with magnesium sulfate (20 g), the solvent was removed, and the residue was purified by column chromatography to give E1 (4.24 g, yield 56%).

A third step; Synthesis of intermediate product (F1)

Intermediate E1 (4.24 g, 8.96 mmol), triphenylphosphine (23.50 g, 89.61 mmol) and orthodichlorobenzene (85 mL) were introduced and refluxed for 12 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 mL) and washed three times with purified water (200 mL). Water was removed from the organic layer with magnesium sulfate (20 g), the solvent was removed, and the residue was purified by column chromatography to obtain F1 (1.94 g, yield 53%).

Step 4; compound NN Synthesis of -2-1

(0.13 g, 0.14 mmol) and potassium carbonate (0.72 g, 5.22 mmol) were added to a solution of the intermediate F1 (1.94 g, 4.75 mmol), iodobenzene (2.13 g, 10.45 mmol), tris (dibenzylideneacetone) dipalladium , Tri-tert-butylphosphine (0.09 g, 0.43 mmol) and toluene (40 mL) were charged and refluxed for 12 hours. After completion of the reaction, the reaction mixture was washed three times with purified water (40 mL), and water was removed with magnesium sulfate (4 g). The solvent was removed and the residue was purified by column chromatography to obtain NN-2-1 (1.2 g, yield 45%).

MS (MALDI-TOF): m / z 561.47 [M] ^< ^{+ &}

Synthetic example  17: Compound NN Synthesis of -2-2

Compound NN-2-2 was synthesized through the reaction scheme 2 in the same manner as in Synthesis Example 16, except that M4 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  18: Compound NN Synthesis of -2-3

Compound NN-2-3 was synthesized through the reaction scheme 2 in the same manner as in Synthesis Example 16 except that M5 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  19: Compound NN Synthesis of -2-4

Compound NN-2-4 was synthesized through the reaction scheme 2 in the same manner as in Synthesis Example 16, except that M6 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  20: Compound NN Synthesis of -2-5

Compound NN-2-5 was synthesized through Reaction Scheme 2 in the same manner as in Synthesis Example 16, except that M9 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  21: Compound NN Synthesis of 2-6

Compound NN-2-6 was synthesized through the reaction scheme 2 in the same manner as in Synthesis Example 16, except that M10 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  22: Compound NN Synthesis of 2-7

Compound NN-2-7 was synthesized through Reaction Scheme 2 in the same manner as in Synthesis Example 16, except that M11 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  23: Compound NN Synthesis of 2-8

Compound NN-2-8 was synthesized through Reaction Formula 2 in the same manner as in Synthesis Example 16, except that M12 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  24: Compound NN Synthesis of 2-9

Compound NN-2-9 was synthesized through Reaction Scheme 2 in the same manner as in Synthesis Example 16 except that M14 was used instead of M3 in the first step of Synthesis Example 16.

Synthetic example  25: Compound NN Synthesis of -2-10

Compound NN-2-10 was synthesized through Reaction Scheme 2 in the same manner as in Synthesis Example 16, except that M15 was used instead of M3 in the first step of Synthesis Example 16.

Specific compounds according to one embodiment of the present invention prepared according to the above synthesis method are shown in Table 2 below.

Reactant M compound Total yield (%) MS [M] ^< ^{+ &}

M-3

NN-2-1

9.6 561.67 M-4

NN-2-2

9.3 561.67 M-5

NN-2-3

8.8 561.67 M-6

NN-2-4

8.5 561.67 M-9

NN-2-5

8.2 562.66 M-10

NN-2-6

8.9 562.66 M-11

NN-2-7

7.5 562.66 M-12

NN-2-8

7.7 562.66 M-14

NN-2-9

9.0 563.65 M-15

NN-2-10

8.3 563.65

(Comparison of simulation characteristics of prepared compounds)

The energy level of each material was calculated by the Gaussian 09 method using a super computer GAIA (IBM power 6), and the results are shown in Table 3 below.

compound Dipole Moment HOMO LUMO T1 S1 NN-1-1 2.40 -5.35 -1.17 3.01 3.40 NN-1-2 1.62 -5.16 -1.36 3.00 3.31 NN-1-3 2.50 -5.24 -1.39 2.89 3.29 NN-1-4 1.31 -5.12 -1.37 2.81 3.37 NN-1-5 1.64 -5.23 -1.39 2.96 3.30 NN-1-6 2.62. -5.14 -1.39 2.95 3.35 NN-1-7 2.02 -5.15 -1.71 2.82 2.96 NN-1-8 2.03 -5.35 -1.53 3.02 3.35 NN-1-9 1.84 -5.12 -1.67 2.74 3.12 NN-1-10 1.93 -5.24 -1.69 2.75 3.18 NN-1-11 2.10 -5.08 -1.72 2.85 3.00 NN-1-12 2.12 -5.30 -1.71 2.90 3.18 NN-1-13 1.04 -5.35 -1.84 2.96 3.04 NN-1-14 1.08 -5.32 -1.81 2.72 3.15 NN-1-15 0.71 -5.17 -1.90 2.67 2.85 NN-2-1 2.52 -5.30 -1.28 2.89 3.49 NN-2-2 1.63 -5.12 -1.30 2.77 3.35 NN-2-3 2.23 -5.28 -1.16 2.92 3.34 NN-2-4 2.20 -5.03 -1.25 2.78 3.30 NN-2-5 2.03 -5.10 -1.59 2.69 3.08 NN-2-6 1.86 -5.26 -1.60 2.76 3.18 NN-2-7 1.68 -5.06 -1.57 2.68 3.01 NN-2-8 2.63 -5.20 -1.50 2.75 3.24 NN-2-9 1.25 -5.23 -1.77 2.61 2.99 NN-2-10 1.69 -5.25 -1.67 2.63 3.09

(Fabrication of organic light emitting device)

Example  One

An organic light emitting device was fabricated using the compound NN-1-1 obtained in Synthesis Example 1 as a host and Ir (PPy) ₃ as a dopant.

As the anode, ITO was used in a thickness of 1000 Å, and as a cathode, aluminum (Al) was used in a thickness of 1000 Å. Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance of 15 Ω / cm ² is cut into a size of 50 mm × 50 mm × 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was performed for 30 minutes.

N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diaminodiphenylsulfonate was deposited on the substrate at a vacuum degree of 650 × 10-7 Pa and a deposition rate of 0.1 to 0.3 nm / - diamine (NPB) (80 nm) was deposited on the hole transport layer to form a hole transport layer having a thickness of 800 ANGSTROM. Subsequently, using the compound NN-1-1 obtained in Synthesis Example 1 under the same vacuum deposition condition, a light emitting layer with a thickness of 300 angstroms was formed. Ir (PPy) ₃ , which is a phosphorescent dopant, was simultaneously deposited thereon. At this time, the deposition rate of the phosphorescent dopant was adjusted so that the phosphorescent dopant content was 7% by weight when the total amount of the light emitting layer was 100% by weight.

(2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (bis (2-methyl-8- quinolinolato) aluminum: BAlq) was deposited thereon to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a film thickness of 200 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic optoelectronic device.

The structure of the organic optoelectronic device was ITO / NPB (80 nm) / EML (compound (NN-1-1) (93 wt%) + Ir (PPy) ₃ (7 wt%), 30 nm) / Balq ) / Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).

Example  2

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-1-2) prepared in Synthesis Example 2 was used as the light emitting layer.

Example  3

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-3) prepared in Synthesis Example 3 was used as the light emitting layer.

Example  4

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-4) prepared in Synthesis Example 4 was used as the light emitting layer.

Example  5

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-1-5) prepared in Synthesis Example 5 was used as the light emitting layer.

Example  6

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-6) prepared in Synthesis Example 6 was used as the light emitting layer.

Example  7

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-7) prepared in Synthesis Example 7 was used as the light emitting layer.

Example  8

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-1-8) prepared in Synthesis Example 8 was used as the light emitting layer.

Example  9

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-1-9) prepared in Synthesis Example 9 was used as the light emitting layer.

Example  10

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-10) prepared in Synthesis Example 10 was used as the light emitting layer.

Example  11

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-11) prepared in Synthesis Example 11 was used as the light emitting layer.

Example  12

An organic photoelectric device was prepared in the same manner as in Example 1 except that the compound (NN-1-12) prepared in Synthesis Example 12 was used as the light emitting layer.

Example  13

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-13) prepared in Synthesis Example 13 was used as the light emitting layer.

Example  14

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-14) prepared in Synthesis Example 14 was used as the light emitting layer.

Example  15

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-1-15) prepared in Synthesis Example 15 was used as the light emitting layer.

Example  16

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-1) prepared in Synthesis Example 16 was used as the light emitting layer.

Example  17

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-2) prepared in Synthesis Example 17 was used as the light emitting layer.

Example  18

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-3) prepared in Synthesis Example 18 was used as the light emitting layer.

Example  19

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-4) prepared in Synthesis Example 19 was used as the light emitting layer.

Example  20

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-2-5) prepared in Synthesis Example 20 was used as the light emitting layer.

Example  21

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-6) prepared in Synthesis Example 21 was used as the light emitting layer.

Example  22

An organic photoelectric device was prepared in the same manner as in Example 1 except that the compound (NN-2-7) prepared in Synthesis Example 22 was used as the light emitting layer.

Example  23

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound (NN-2-8) prepared in Synthesis Example 23 was used as the light emitting layer.

Example  24

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-2-9) prepared in Synthesis Example 24 was used as the light emitting layer.

Example  25

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound (NN-2-10) prepared in Synthesis Example 25 was used as the emitting layer.

Comparative Example  One

An organic light emitting device was prepared in the same manner as in Example 1 except that CBP having the following structure was used in place of the compound NN-1-1 of Example 1.

The structures of NPB, BAlq, CBP and Ir (PPy) ₃ used in the above organic light emitting device are as follows.

(Performance Measurement of Organic Light Emitting Device)

For each of the organic light emitting devices manufactured in Examples 1 to 25 and Comparative Example 1, the current density change, the luminance change, and the luminous efficiency were measured according to the voltage. Specific measurement methods are as follows, and the results are shown in Table 4 below

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light-emitting device manufactured, luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

No. The light- The driving voltage (V) color
(EL color) efficiency
(cd / A) Comparative Example 1 CBP 4.8 Green 31.4 Example 1 NN-1-1 4.7 Green 33.5 Example 2 NN-1-2 4.6 Green 34.3 Example 3 NN-1-3 4.7 Green 32.9 Example 4 NN-1-4 4.5 Green 37.4 Example 5 NN-1-5 4.6 Green 34.5 Example 6 NN-1-6 4.7 Green 33.7 Example 7 NN-1-7 4.5 Green 36.8 Example 8 NN-1-8 4.8 Green 32.4 Example 9 NN-1-9 4.3 Green 39.8 Example 10 NN-1-10 4.3 Green 40.3 Example 11 NN-1-11 4.5 Green 37.5 Example 12 NN-1-12 4.7 Green 33.5 Example 13 NN-1-13 4.7 Green 33.8 Example 14 NN-1-14 4.3 Green 39.9 Example 15 NN-1-15 4.6 Green 35.1 Example 16 NN-2-1 4.7 Green 34.1 Example 17 NN-2-2 4.3 Green 39.2 Example 18 NN-2-3 4.4 Green 39.6 Example 19 NN-2-4 4.7 Green 33.6 Example 20 NN-2-5 4.3 Green 40.2 Example 21 NN-2-6 4.3 Green 39.8 Example 22 NN-2-7 4.4 Green 39.6 Example 23 NN-2-8 4.6 Green 34.6 Example 24 NN-2-9 4.5 Green 37.2 Example 25 NN-2-10 4.5 Green 37.6

As can be seen from Table 4, the organic light emitting devices of Examples 1 to 25 exhibited improved characteristics in terms of driving voltage, luminous efficiency, and / or power efficiency as compared with Comparative Example 1.

Specifically, the compounds used in the organic light emitting devices according to Examples 1 to 25 have a structure that is easy to receive electrons including nitrogen, unlike the compounds used in the organic light emitting device according to Comparative Example 1. Accordingly, it can be confirmed that the driving voltage of the organic light emitting device of Examples 1 to 25 is lower than that of the organic light emitting device of Comparative Example 1.

Further, the compounds used in the organic light emitting devices according to Examples 1 to 25 had a bipolar structure including a pyrrolocarbazole structure susceptible to holes and a nitrogen-containing ring part susceptible to electrons, so that the flow of holes and electrons was appropriately The organic electroluminescent device according to Examples 1 to 25 has higher luminous efficiency than the organic electroluminescent device according to Comparative Example 1. [

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100: organic light emitting device 200: organic light emitting device
105: organic layer
110: cathode
120: anode
130: light emitting layer 230: light emitting layer
140: hole assist layer

Claims (15)

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

In Formula 1,
X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)
At least one of X ¹ and X ² is NL ¹ -R ^a ,
X ³ to X ⁸ are each independently N or CL ² -R ^b ,
R ¹ , R ² , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocyclo An alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 alkoxycarbonyl groups, C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,
R ¹ and R ² are each independently present or fused together to form a ring,
R ^b Are independently absent or two adjacent R < ^{b &} gt ^; are fused to form a ring,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, An unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C6 to C30 heteroarylene amine group, A substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, It is a combination of these. The method according to claim 1,
Wherein each of X ³ to X ⁸ is CL ² -R ^b, or one of X ³ to X ⁸ is N. The method according to claim 1,
A compound represented by any one of the following formulas (2) to (5):
[Chemical Formula 2] < EMI ID =

,

,
[Chemical Formula 4]

,

,
In the above formulas 2 to 5,
X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)
At least one of X ¹ and X ² is NL ¹ -R ^a ,
R ¹ , R ² , R ^a and R ^b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocyclo An alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 alkoxycarbonyl groups, C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof. The method of claim 3,
A compound represented by any one of the following formulas (6) to (38):
[Chemical Formula 7] [Chemical Formula 8] Chemical Formula 9 [Chemical Formula 10]

,

,

,

,

,
[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]

,

,

,

,
[Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]

,

,

,

,
[Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

,

,

,

,
[Chemical Formula 25] [Chemical Formula 25]

,

,

,

,
[Chemical Formula 30] [Chemical Formula 30]

,

,

,

,

,
[Chemical Formula 32] [Chemical Formula 32]

,

,

,

,
[Chemical Formula 37] [Chemical Formula 38]

,

,

,
In the above Chemical Formulas 6 to 38,
X ¹ and X ² are each independently selected from NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S = O), SO ₂ O)
At least one of X ¹ and X ² is NL ¹ -R ^a ,
R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, ego,
L ¹ is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof. The method according to claim 1,
A compound represented by any one of the following formulas (39) to (42):
[Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]

,

,

,

,
In the above formulas (39) to (42)
X ³ to X ⁸ are each independently N or CL ² -R ^b ,
R ¹ and R ² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heteroaryl group, Forming a ring,
R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, Substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted C3 to C40 silyloxy groups, substituted or unsubstituted C1 to C30 acyl groups, substituted or unsubstituted C1 to C20 acyloxy groups, substituted or unsubstituted C1 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroarylene group, or a combination thereof. 6. The method of claim 5,
Wherein R ¹ and R ² in Formula 40 or Formula 41 are fused to each other to form a compound represented by Formula 43 or 44:
[Chemical Formula 43]

,

,
In the above formula (43) or (44)
X ³ to X ⁸ are each independently N or CL ² -R ^b ,
R ^a and R ^b are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, Substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted C3 to C40 silyloxy groups, substituted or unsubstituted C1 to C30 acyl groups, substituted or unsubstituted C1 to C20 acyloxy groups, substituted or unsubstituted C1 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group. The method according to claim 1,
A compound represented by any one of the following formulas (45) to (55):
[Chemical Formula 48] [Chemical Formula 47] [Chemical Formula 48]

,

,

,

,
[Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52]

,

,

,

,
[Chemical Formula 55] [Chemical Formula 55]

,

,

,
In Formulas 45 to 55,
X ² is NL ¹ -R ^a , CR ¹ R ² , SiR ¹ R ² , O, S, SO (S═O), SO ₂ (O═S═O)
X ³ to X ⁸ are each independently N or CL ² -R ^b ,
R ¹ and R ² are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, Or fused together to form a ring,
R ^a and R ^b are each independently present, or two adjacent R ^b are fused to form a ring,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group. The method according to claim 1,
Wherein R & lt ^{; a} & gt ^; and R < ^b & gt ^; are each independently one of the substituted or unsubstituted functional groups listed in the following Group &
[Group I]

In the group I,
Z are each independently N or CR ^c,
W is O, S, SO, SO ₂ , NR ^d , CR ^e R ^f , or SiR ^g R ^h ,
Wherein R ^c to R ^h are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl An amino group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonyl An amino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C20 acyl group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclothiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A halogen atom, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a perorenyl group or a substituted or unsubstituted C1 to C30 heteroarylthiol group Lt; / RTI &
* Is a connecting point and may be located in any of the elements forming the functional group. 9. The method of claim 8,
Wherein R & lt ^{; a} & gt ^; and R < ^b & gt ^; are each independently one of the substituted or unsubstituted functional groups listed in the following Group II:
[Group II]

In the group II,
R 'and R "are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a substituted or unsubstituted silyl group ,
* Is the connection point. 9. The method of claim 8,
Wherein R & lt ^{; a} & gt ^; and R < ^b & gt ^; are each independently one of the substituted or unsubstituted functional groups listed in the following Group III:
[Group III]

In the group III,
* Is the connection point. An anode and a cathode facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer comprises the compound according to any one of claims 1 to 10. 12. The method of claim 11,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound. 13. The method of claim 12,
Wherein the compound is included as a host of the light emitting layer. 12. The method of claim 11,
Wherein the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer,
Wherein the auxiliary layer comprises the compound. 12. A display device comprising the organic electroluminescent device according to claim 11.

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