KR20170008004A - Organic compound for optoelectronic device and composition for optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to a compound for organic optoelectronic devices, represented by chemical formula 1. The present invention further relates to an organic optoelectronic device including the same, and a display device. The detailed description of the chemical formula 1 is the same as defined in the present specification. According to an embodiment of the present invention, the compound for organic optoelectronic devices enables the production of organic optoelectronic devices exhibiting high efficiency and long lifespan.

Description

TECHNICAL FIELD The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices and display devices.

An organic optoelectronic device is an element capable of converting electrical energy to 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.

One embodiment provides a compound for an organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.

Another embodiment provides an organic optoelectronic device including the compound for the organic optoelectronic device.

Another embodiment provides a display device comprising the organic opto-electronic device.

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following general formula (I).

(I)

In the above formula (I)

X ¹ and X ² are each independently N, O or S,

Wherein ^{one of} X < ^{1 >} and X < ² > is N,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

Ar ¹ and Ar ² are each independently a functional group having a hole property, a functional group having an electronic property, or a combination thereof,

The functional group having the hole property may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted fluorenyl group, or a combination thereof,

The functional group having an electron characteristic is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one N, provided that the carbazolyl group is excluded,

R ¹ to R ³ 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 C6 to C30 aryl group, Substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C6 to C30 arylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C40 silyl groups, substituted or unsubstituted C3 to C40 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, Lt; / RTI &

The term "substituted" as used herein means that at least one hydrogen is substituted by deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, Means a C30 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

According to another embodiment, there is provided an organic electroluminescent device comprising 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 comprises an organic optoelectronic device including the above- to provide.

According to another embodiment, there is provided a display device including the organic optoelectronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.

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 hydrogen in the substituent or compound is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxy group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkyl A C6 to C30 aryl group, a C6 to C30 aryl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, Substituted by cyano group.

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

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. 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 of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 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.

As used herein, the term " aryl group "is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, May also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heterocyclic group "is a superordinate concept including a heteroaryl group, and includes N, O, and S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

As used herein, the term " heteroaryl group "means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group instead of carbon (C). Two or more heteroaryl groups may be directly connected through a sigma bond, or when the C2 to C60 heteroaryl group includes two or more rings, two or more rings may be fused with each other. 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 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, 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 indenyl group, a substituted or unsubstituted fluorenyl 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 pyridyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyridinyl group, A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, Substituted or unsubstituted oxadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted quinazolinyl group, 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 acridinyl group, A substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted phenothiopheny group, a substituted or unsubstituted phenothiopheny group, a substituted or unsubstituted phenothiopheny group, a substituted or unsubstituted phenothiopheny group, a substituted or unsubstituted phenothiopheny group, A substituted or unsubstituted benzofuranylpyrimidinyl group, a substituted or unsubstituted benzofuranpyridinyl group, a substituted or unsubstituted benzofuranylpyrimidinyl group, a substituted or unsubstituted benzofuranylpyridazinyl 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 substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, or a combination thereof.

In the present specification, a single bond means a bond directly connected to a carbon atom or a hetero atom other than carbon. Specifically, L means a single bond, meaning that the substituent connected to L is directly connected to the center core do. 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 refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement.

The compounds for organic optoelectronic devices according to one embodiment will be described below.

The compound for organic optoelectronic devices according to one embodiment is represented by the following formula (I).

(I)

In the above formula (I)

X ¹ and X ² are each independently N, O or S,

Wherein ^{one of} X < ^{1 >} and X < ² > is N,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

Ar ¹ and Ar ² are each independently a functional group having a hole property, a functional group having an electronic property, or a combination thereof,

The functional group having the hole property may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted fluorenyl group, or a combination thereof,

The functional group having an electron characteristic is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one N, provided that the carbazolyl group is excluded,

R ¹ to R ³ 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 C6 to C30 aryl group, Substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C6 to C30 arylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C40 silyl groups, substituted or unsubstituted C3 to C40 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, Lt; / RTI &

The term "substituted" as used herein means that at least one hydrogen is substituted by deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, Means a C30 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The compound for organic optoelectronic device represented by the above formula (I) may be a form in which a carbazole group and a thiazole-series protrusion are connected to each other, or a carbazole group and an oxazole group is connected to each other and may function as a core exhibiting hole characteristics.

The core to which the carbazole group and the thiazole-series protrusion are connected and the core to which the carbazole group and the oxazole group are connected may be used as a material exhibiting strong hole characteristics together with a substituent showing hole properties,

Can be used as a material exhibiting an amphoteric property together with a substituent showing an electronic characteristic. In particular, when a substituent having an electronic characteristic is contained, it has a T1 value suitable for use as a phosphorescent host and excellent thermal stability, and has a high HOMO energy level value, is suitable for implementation of a low driving device and is suitable as a light emitting material.

The compound for organic optoelectronic devices may be represented by any of the following formulas I-A, I-B, I-C and I-D depending on the kind of each element located at X ¹ and X ² .

[Formula I-A] [Formula I-B]

[Chemical Formula I-C] [Chemical Formula I-D]

In the above Formulas I-A, I-B, I-C, I-D and I-E, L ¹ and L ² , Ar ¹ and Ar ² and R ¹ to R ³ are as described above.

According to an embodiment of the present invention, Ar ¹ and Ar ² may be both functional groups having hole characteristics. In this case, it can be designed as a compound having a strong hole characteristic.

According to another aspect of the invention, wherein Ar ¹ is a functional group, and the Ar ² may be an operation having an electronic property, or the Ar ¹ is a functional group having the electronic properties, and the Ar ² has a hole characteristics And may be a functional group having hole properties. In this case, it can be designed as a compound having an amphoteric characteristic.

The functional group having the hole property may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted heteroaryl group, Substituted or unsubstituted naphthyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted anthracenyl groups, substituted or unsubstituted fluoranthenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted pies A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, Or an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

More specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluoro A substituted or unsubstituted dibenzothiocarbonyl group, a substituted or unsubstituted dibenzothiocarbonyl group, a substituted or unsubstituted dibenzothiocarbonyl group, a substituted or unsubstituted dibenzothiocarbonyl group, a substituted or unsubstituted dibenzothiocarbonyl group, Lt; / RTI >

For example, a group selected from the group listed in the following substituted or unsubstituted group I.

[Group I]

In the group I,

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 C2 to C30 heteroaryl group,

* Is a binding site with neighboring atoms.

As the most specific example, the functional group having the hole property may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

The functional group having the above-mentioned electronic characteristic is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one N, with the proviso that the carbazolyl group is excluded, specifically, a substituted or unsubstituted pyridinyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, A substituted or unsubstituted indazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted indazolyl group, A substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a combination thereof.

More specifically, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted Or a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, Or an unsubstituted benzothiophenepyrimidinyl group, or a substituted or unsubstituted benzofuranpyrimidinyl group, or a combination thereof.

For example, a group selected from the group listed in the following substituted or unsubstituted group II.

[Group II]

In the group II,

Z is each independently N, C or CR ^c , at least one of Z is N,

W and Y are each independently N, O, S, SO, SO ₂ , C, CR ^d , CR ^e R ^f , SiR ^g or SiR ^h R ⁱ ,

Wherein R ^c to R ⁱ are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, substituted or unsubstituted C3 to C30 heterocycloalkyl groups, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group,

* Is a binding site with neighboring atoms and is located at any one of the elements forming the functional group.

For example, the groups listed in the substituted or unsubstituted group II may be selected from the substituted or unsubstituted functional groups listed in Group II-1 below.

[Group II-1]

In the group II-1,

* Is a binding site with neighboring atoms.

According to an embodiment of the present invention, when X ¹ is N, X ² is S, L ¹ and L ² are each independently a single bond, a substituted or unsubstituted Substituted or unsubstituted phenylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted quinazolinylene group, or a combination thereof, and Ar ¹ and Ar ² are each independently substituted or unsubstituted A substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted isoquinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted quinazolinyl group, Pyrrole Inde-pyridyl group, a substituted or unsubstituted no-pyrimidinyl group, a substituted or unsubstituted benzothiophen-pyrimidinyl group, a substituted or unsubstituted benzofuran-pyrimidinyl group, and wherein R ¹ to R ³ are, each independently, a hydrogen , Deuterium, or a C1 to C10 alkyl group, but is not limited thereto.

When designed as a compound having amphoteric properties according to another embodiment of the present invention, X ¹ is N, X ² is S, and L ¹ and L ² are each independently a single bond, A substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted quinazolinylene group, or a combination thereof, and Ar ¹ is a functional group having an electron characteristic, for example, A substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, A substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted benzopyrimidinyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted indopyrimidinyl group, The benzothiophene-pyrimidinyl group, or a substituted or unsubstituted benzofuran-pyrimidinyl group, and wherein Ar ² is a functional group having the hole characteristics, for example a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted A substituted naphthyl group, or a substituted or unsubstituted fluorenyl group, and each of R ¹ to R ³ may independently be hydrogen, deuterium, or a C1 to C10 alkyl group, but is not limited thereto.

When designed as a compound having amphoteric properties according to another embodiment, X ¹ is N, X ² is S, and L ¹ and L ² are each independently a single bond, a substituted or unsubstituted A substituted or unsubstituted naphthylene group, a substituted or unsubstituted quinazolinylene group, or a combination thereof, and Ar ¹ is a functional group having a hole property, such as a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group, Ar ² is a functional group having an electron characteristic, for example, a substituted or unsubstituted pyridyl group , A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinane A substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted benzoimidazolyl group, Or a substituted or unsubstituted benzofuran-pyrimidinyl group, and each of R ¹ to R ³ may independently be hydrogen, deuterium, or a C1 to C10 alkyl group, but is not limited thereto.

Particularly, in the case where Ar ¹ is a functional group having a hole property and Ar ² is a functional group having an electron characteristic, luminous efficiency and lifetime characteristics can be further improved.

The compound for organic optoelectronic devices represented by Formula (I) may be one of the compounds listed below, but is not limited thereto.

[Group 1]

[1] [2] [3] [4]

[5] [6] [7] [8]

[9] [10] [11] [12]

[13] [14] [15] [16]

[17] 18 [19] [20]

[21] 22 [23] [24]

[25] 26 [27] [28]

[29] [30] [31] [32]

[33] [34] [35] [36]

[37] 38 [39] [40]

The compound for an organic optoelectronic device may further include a dopant. The dopant may be a red, green or blue dopant.

The dopant may be a material that emits light by mixing a small amount of light, and may be a material such as a metal complex that emits light by multiple excitation that excites it to a triplet state. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof And the like. The phosphorescent dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto.

(Z)

L ₂ MX

In the above formula (Z), M is a metal, L and X are the same or different from each other and are ligands that complex with M.

M may be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, Lt; / RTI >

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

The organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer provides an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device .

The organic layer includes a light emitting layer, and the light emitting layer may include a compound for an organic optoelectronic device of the present invention.

Specifically, the compound for an organic optoelectronic device can be included as a host of the light emitting layer. For example, as a red host of the light emitting layer.

In one embodiment of the present invention, the organic layer includes at least one auxiliary layer selected from a hole injecting layer, a hole transporting layer, a hole transporting auxiliary layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer, Layer may be an organic optoelectronic device including the compound for the organic optoelectronic device. For example, an electron transporting auxiliary layer, an electron transporting layer, and an electron injection layer.

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 compound for the organic optoelectronic device described above.

The light emitting layer 130 may include, for example, the compound for organic optoelectronic devices described above alone or may be mixed with at least two of the compounds for organic optoelectronic devices described above, . The compound for organic optoelectronic devices described above may be contained in the form of, for example, a host and a dopant when mixed with other compound for the organic optoelectronic device. The compound for the organic optoelectronic device may be, for example, a host, As shown in FIG. 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 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 compound for organic optoelectronic devices of the present invention can 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.

Synthesis of compounds for organic optoelectronic devices

Hereinafter, the starting materials and reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise specified.

The above compounds shown as more specific examples of the compound for organic optoelectronic devices of the present invention were synthesized by the following reaction formula.

[Synthesis of intermediate]

Step 1 : Synthesis of intermediate (A)

Dissolve 11.12 g (82.68 mmol) of CuCl _{2 in} 300 mL of ACN under nitrogen and slowly add 12.08 mL (103.35 mmol) of t-BuONO at room temperature. After stirring at room temperature for 10 minutes, 10.00 g (68.90 mmol) of 2-amino-5-nitrothiazole was dissolved in 15 mL of ACN, slowly added to the reaction solution and stirred at 65 ° C for 30 minutes under a nitrogen stream. After the reaction solution is cooled to room temperature, the solvent is removed, and the mixture is extracted with dichloromethane and distilled water. The organic layer is subjected to silica gel filtration. The organic solution was removed and the residue was subjected to silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) to obtain 7.4 g (yield: 65%) of intermediate (A).

Step 2 ; Synthesis of intermediate (B)

7.4 g (44.97 mmol) of the intermediate product (A) is suspended in 200 mL of n-hexane, a small amount of iodine is added, and 4.84 mL (47.22 mmol) of Br ₂ is slowly added thereto. The mixture was stirred at room temperature for 12 hours, quenched with an aqueous NaS ₂ O ₃ solution, and the organic layer was subjected to silica filtration, and then the organic solution was removed to obtain 9.5 g (yield: 87%) of intermediate (B).

Step 3 ; Synthesis of intermediate (C)

The intermediate product (B) 9.0 g (36.97 mmol ), phenyl Boro Nick Acid 4.96 g (40.66 mmol), K 2 CO 3 11.23 g (81.32 mmol), Pd (PPh 3) 4 0.85 g (0.74 mmmol) in toluene 150 ml , And suspended in distilled water (80 ml), and the mixture was stirred under reflux for 12 hours under a nitrogen stream. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. The residue was subjected to silica column chromatography with hexane: ethyl acetate = 9: 1 (v / v) to obtain 7.3 g (yield: 89% ≪ / RTI >

Fourth Step: Synthesis of intermediate (D)

7.0 g (31.64 mmol) of the intermediate product (C) and 27.53 mL (158.20 mmol) of triethyl phosphite were stirred under reflux for 4 hours under a nitrogen stream. After completion of the reaction, the reaction solvent was removed and silica column chromatography was performed with hexane: dichloromethane = 7: 3 (v / v) to obtain 5.1 g (yield: 77%) of intermediate (D).

Synthetic example  1: Synthesis of Compound (9)

1st Step: Synthesis of intermediate product (E)

Intermediate (D) 10.0 g (47.92 mmol ) and iodo in benzene 6.44 mL (57.51 mmol), NaO (t-Bu) 6.91 g (71.88 mmol), Pd (dba) 2 0.55 g (0.96 mmmol) in toluene 180 mL After suspending, 0.47 mL (1.92 mmol) of P (t-Bu) ₃ was added and the mixture was refluxed under nitrogen stream for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed and silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v) gave 11.5 g (yield: 84%) of intermediate (E).

Second Step: Synthesis of Compound 9

8.0 g (28.09 mmol) of the intermediate (E), 10 g of the compound (E-1) (obtained in Example 1 of KR2013-0020398A in place of 2- bromo-4, 6 was prepared using diphenyl-triazine) 16.21 g (30.90 mmol), K 2 CO 3 8.54 g (61.81 mmol), Pd (PPh 3) 4 0.65 g (0.56 mmmol) of a toluene 150 ml and distilled water (80 ml), and the mixture was stirred under reflux for 12 hours under a nitrogen stream. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. The residue was subjected to silica column chromatography using n-hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / 14.7 g (yield: 81%) of the title compound was obtained.

Synthetic example  2: Synthesis of Compound 10

8.0 g (28.09 mmol) of the intermediate (E), the compound (E-2, the reaction product of Example 2 of Korean Patent Publication No. KR2013-0020398A was changed to 2- A solution of 18.56 g (30.90 mmol) K ₂ CO _3, 8.54 g (61.81 mmol) Pd (PPh ₃ ) ₄ (0.65 g, 0.56 mmol, ) Was suspended in toluene (150 ml) and distilled water (80 ml), and the mixture was refluxed under nitrogen stream for 12 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. The residue was subjected to silica column chromatography with n-hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / 16.2 g (Yield: 80%) was obtained.

Synthetic example  3: Synthesis of Compound 13

8.0 g (28.09 mmol) of the intermediate (E), 10 g of the compound (E-3, Example 1 of Korean Patent Publication No. KR2013-0020398A in which 2-bromo-4,6-diphenylpyridine 15.37 g (30.90 mmol) of K ₂ CO _3, 8.54 g (61.81 mmol) of K ₂ CO _{3 and} 0.65 g (0.56 mmol) of Pd (PPh ₃ ) ₄ were dissolved in 150 ml of toluene, distilled water 80 ml, and the mixture was stirred under reflux for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and distilled under reduced pressure. The residue was subjected to silica column chromatography with n-hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / 14.5 g (yield: 83%) of the title compound was obtained.

Synthetic example  4: Synthesis of Compound 14

8.0 g (28.09 mmol) of the intermediate (E), the compound (E-4), the reaction product in Example 1 of Korean Patent Publication No. KR2013-0020398A was changed to 2- 15.37 g (30.90 mmol) of K ₂ CO _3, 8.54 g (61.81 mmol) of K ₂ CO _{3 and} 0.65 g (0.56 mmol) of Pd (PPh ₃ ) ₄ were dissolved in toluene 150 ml, and distilled water (80 ml), and the mixture was stirred under reflux for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and vacuum distilled. The residue was subjected to silica column chromatography with n-hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / 15.2 g (Yield: 78%) was obtained.

Synthetic example  5: Synthesis of Compound 1

1st Step: Synthesis of intermediate (F)

30.27 g (105.43 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 29.14 g (210.86 mmol) K ₂ CO ₃ , Pd (PPh ₃ ) ₄ 2.22 g (1.92 mmmol) was suspended in 400 ml of toluene and 200 ml of distilled water, followed by reflux stirring for 12 hours under a nitrogen stream. After completion of the reaction, the reaction solution was extracted with dichloromethane, filtered through silica gel, and vacuum distilled. The residue was subjected to silica column chromatography with n-hexane: dichloromethane = 6: 4 (v / v) to obtain 30.27 g (Yield: 76%).

Second Step: Synthesis of Compound 1

7.09 g (26.47 mmol) of 2-chloro-4,5-diphenyl-1,3,5-triazine, 3.47 g (36.10 mmol) of NaO (t- Bu), 10.0 g (24.07 mmol) 0.28 g (0.48 mmmol) of Pd (dba) ₂ was suspended in 100 mL of toluene, and 0.23 mL (0.96 mmol) of P (t-Bu) ₃ was added thereto and stirred under reflux for 24 hours under a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / acetone to obtain 12.8 g (yield: 82%) of compound 1.

Synthetic example  6: Synthesis of Compound 3

A mixture of 10.0 g (24.07 mmol) of intermediate (F), 9.10 g (26.47 mmol) of 2- (4-chlorophenyl) 0.28 g (0.48 mmmol) of Pd (dba) ₂ was suspended in 100 mL of toluene, and 0.23 mL (0.96 mmol) of P (t-Bu) ₃ was added thereto and stirred under reflux for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / acetone to obtain 13.9 g (yield: 80%) of compound 3.

Synthetic example  7: Synthesis of Compound 5

Intermediate (F) 10.0 g (24.07 mmol ) and 2-chloro-4-phenyl-quinazoline 6.37 g (26.47 mmol), NaO (t-Bu) 3.47 g (36.10 mmol), Pd (dba) 2 0.28 g (0.48 mmmol ) Was suspended in 100 mL of toluene, and 0.23 mL (0.96 mmol) of P (t-Bu) ₃ was added thereto, followed by reflux stirring for 24 hours in a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / acetone to obtain 12.2 g (yield: 82%) of compound 5.

Synthetic example  8: Synthesis of Compound 7

8.39 g (26.47 mmol) of 2- (4-chlorophenyl) -4-phenyl-1,3-quinazoline and 3.47 g (36.10 mmol) of NaO (t- 0.28 g (0.48 mmmol) of Pd (dba) ₂ was suspended in 100 mL of toluene, and 0.23 mL (0.96 mmol) of P (t-Bu) ₃ was added thereto and stirred under reflux for 24 hours under a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 8: 2 (v / v) and recrystallized from dichloromethane / acetone to obtain 13.6 g (yield: 81%) of Compound 7.

(Fabrication of organic light emitting device)

Example  One

An organic light emitting device was fabricated using the compound 9 obtained in Synthesis Example 1 as a host and acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) ₂ acac) as a dopant.

As the anode, ITO was used to a thickness of 1500 Å, and aluminum (Al) was used as a cathode to 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, UV ozone cleaning was used for 30 minutes.

The degree of vacuum in the upper substrate 650 × 10 ^-7 Pa, the deposition rate of 0.1 to 0.3 nm / s in terms 4,4'-bis [N- [4- { N, N-bis (3-methylphenyl) amino} -phenyl ] -N-phenylamino] biphenyl [DNTPD] was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. Subsequently, HT-1 was vacuum vapor deposited under the same vacuum deposition conditions to form a 300 Å thick hole transport layer. Next, a light emitting layer having a thickness of 300 angstroms was formed using the compound 9 obtained in Synthesis Example 1 under the same vacuum deposition conditions. The phosphorescent dopant acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) ₂ acac) Respectively. 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.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å. Then, Tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 250 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic photoelectric device.

The structure of the organic photoelectric device is ITO / DNTPD (60 nm) / HT-1 (30 nm) / EML ( compound 9 (93 _{wt%) + Ir (pq) 2} acac (7 wt%), 30 nm) / Balq (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (100 nm).

Example  2 to 8

The organic light emitting devices corresponding to Examples 2 to 8 were prepared in the same manner as in Example 1, except that the compounds of Synthesis Examples 2 to 8 were used in place of the compound 9 of Synthesis Example 1, .

Comparative Example  One

An organic light emitting device was fabricated in the same manner as in Example 1 except that 4,4'-di (9H-carbazol-9-yl) biphenyl (CBP) was used instead of the compound 9 of Synthesis Example 1.

The structures of DNTPD, BAlq, HT-1, CBP, and Ir (pq) ₂ acac used in the production of the organic light emitting device are as follows.

evaluation

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting device according to Examples 1 to 8 and Comparative Example 1 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 1.

(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).

(4) Life measurement

The initial luminance (cd / m ² ) was emitted at 3000 cd / m ² , and the decrease in luminance over time was measured to determine the time to reduce to 90% of the initial luminance.

No. compound The driving voltage (V) color
(EL color) efficiency
(cd / A) 90% lifetime (h)
At 3000 cd / m ² Example 1 Compound 9 6.2 Red 49.1 109 Example 2 Compound 10 6.4 Red 47.5 100 Example 3 Compound 13 6.0 Red 48.5 120 Example 4 Compound 14 6.1 Red 48.1 113 Example 5 Compound 1 6.6 Red 47.9 95 Example 6 Compound 3 6.8 Red 47.6 92 Example 7 Compound 5 6.5 Red 48.2 99 Example 8 Compound 7 6.9 Red 47.8 91 Comparative Example 1 CBP 7.4 Red 37.2 50

Referring to Table 1, it can be seen that the organic light emitting devices according to Examples 1 to 8 have significantly improved luminous efficiency and lifetime characteristics as compared with the organic light emitting 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, 200: Organic light emitting device
105: organic layer
110: cathode
120: anode
130: light emitting layer
140: hole assist layer

Claims (16)

A compound for an organic optoelectronic device represented by the following formula (I):
(I)

In the above formula (I)
X ¹ and X ² are each independently N, O or S,
Wherein ^{one of} X < ^{1 >} and X < ² > is N,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
Ar ¹ and Ar ² are each independently a functional group having a hole property, a functional group having an electronic property, or a combination thereof,
The functional group having the hole property may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted fluorenyl group, or a combination thereof,
The functional group having an electron characteristic is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one N, provided that the carbazolyl group is excluded,
R ¹ to R ³ 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 C6 to C30 aryl group, Substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C6 to C30 arylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C40 silyl groups, substituted or unsubstituted C3 to C40 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, Lt; / RTI &
The term "substituted" as used herein means that at least one hydrogen is substituted by deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, Means a C30 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group. The method according to claim 1,
A compound for an organic optoelectronic device represented by any one of the following formulas (I-A) to (I-D):
[Formula I-A] [Formula I-B]

[Chemical Formula I-C] [Chemical Formula I-D]

In the above formulas (I-A) to (I-D)
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
Ar ¹ and Ar ² are each independently a functional group having a hole property, a functional group having an electronic property, or a combination thereof,
The functional group having the hole property may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted fluorenyl group, or a combination thereof,
The functional group having an electron characteristic is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one N, with the proviso that the carbazolyl group is excluded,
R ¹ to R ³ 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 C6 to C30 aryl group, Substituted or unsubstituted C2 to C30 heteroaryl groups, substituted or unsubstituted C6 to C30 arylamine groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C40 silyl groups, substituted or unsubstituted C3 to C40 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, It is a combination. The method according to claim 1,
Ar ¹ and Ar ² are a functional group having a hole property;
Ar ¹ is a functional group having a hole property, and Ar ² is a functional group having an electronic property; or
Wherein Ar ¹ is a functional group having an electron characteristic, and Ar ² is a functional group having a hole characteristic. The method according to claim 1,
Wherein the functional group having the hole property is selected from substituted or unsubstituted groups listed in the following Group < RTI ID = 0.0 > I: < / RTI &
[Group I]

In the group I,
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 C2 to C30 heteroaryl group,
* Is a binding site with neighboring atoms. The method according to claim 1,
Wherein the functional group having the above-mentioned electronic characteristic is selected from the group listed in the following substituted or unsubstituted group II:
[Group II]

In the group II,
Z is each independently N or CR < ^c >, at least one of Z is N,
W and Y are each independently N, O, S, SO, SO ₂ , CR ^d , CR ^e R ^f , SiR ^g or SiR ^h R ⁱ ,
Wherein R ^c to R ⁱ are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, substituted or unsubstituted C3 to C30 heterocycloalkyl groups, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group,
* Is a binding site with neighboring atoms and is located at any one of the elements forming the functional group. The method of claim 5,
Wherein the substituted or unsubstituted group listed in Group II is one of the substituted or unsubstituted functional groups listed in Group II-1 below:
[Group II-1]

In the group II-1,
* Is a binding site with neighboring atoms. The method according to claim 1,
X ¹ and X ² are each independently N, O or S,
Wherein ^{one of} X < ^{1 >} and X < ² > is N,
L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted quinazolinylene group, Or a combination thereof,
Ar ¹ and Ar ² each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group , A substituted or unsubstituted thiazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted isoquinazolinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted pyrazolopyrimidinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyrrolopyridyl group, a substituted or unsubstituted indenopyrimidinyl group, a substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted benzofuran pyrimidyl / RTI >
Wherein R ¹ to R ³ are each independently hydrogen, deuterium, or a C1 to C10 alkyl group. The method according to claim 1,
Wherein X ¹ is N, X ² is S,
Each of L ¹ and L ² independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted quinazolinylene group ego,
R ¹ to R ³ are each hydrogen, deuterium or a C1 to C10 alkyl group,
Ar ¹ is a functional group having a hole property, and Ar ² is a functional group having an electron characteristic; or
Wherein Ar ¹ is a functional group having an electron characteristic, and Ar ² is a functional group having a hole characteristic. 9. The method of claim 8,
Wherein Ar < ¹ > is a functional group having a hole property,
Wherein Ar < ² > is a functional group having an electron characteristic. 9. The method of claim 8,
Ar ¹ represents a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted Or a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted indopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, a substituted or unsubstituted aminopyrimidinyl group, Or an unsubstituted benzothiophenepyrimidinyl group or a substituted or unsubstituted benzofuran pyrimidinyl group, Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group , Or a substituted or unsubstituted fluorenyl group; or
Wherein Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group, Ar ² is a substituted or unsubstituted pyridyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted indolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted benzofuran pyrimidinyl group. The method according to claim 1,
A compound for an organic optoelectronic device, which is one of the compounds listed in the following Group 1:
[Group 1]
[1] [2] [3] [4]

[5] [6] [7] [8]

[9] [10] [11] [12]

[13] [14] [15] [16]

[17] 18 [19] [20]

[21] 22 [23] [24]

[25] 26 [27] [28]

[29] [30] [31] [32]

[33] [34] [35] [36]

[37] 38 [39] [40]

. 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 for an organic optoelectronic device according to any one of claims 1 to 11. 13. The method of claim 12,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound for an organic optoelectronic device. 14. The method of claim 13,
Wherein the compound for an organic optoelectronic device is included as a host of the light emitting layer. 14. The method of claim 13,
Wherein the compound for an organic optoelectronic device is included as a red host of the light emitting layer. 13. A display device comprising the organic opto-electronic device according to claim 12.

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