KR101707907B1 - Compound, organic optoelectric device and display device - Google Patents

Abstract

(상기 화학식 1에서, X¹ 내지 X⁸, L 및 T의 정의는 명세서에 정의된 바와 같다.)And a display device including the organic optoelectronic device.
[Chemical Formula 1]

(In the above formula (1), the definitions of X ¹ to X ⁸ , L and T are as defined in 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]

Wherein X ¹ is N or CR ¹ , X ² is N or CR ² , X ³ is N or CR ³ , X ⁴ is N or CR ⁴ , X ⁵ is N or CR ⁵ , X ⁶ is N or CR ⁶ , X ⁷ is N or CR ⁷ , X ⁸ is N or CR ⁸ ,

R ¹ to R ⁸ and T each independently represent 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 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 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 aryloxy 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 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 to R ⁸ are each independently present, or two adjacent ones of R ¹ to R ⁸ are fused to each other to form a ring,

L is 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, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 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 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, or a combination thereof.

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.

A substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group or a trifluoromethyl group, or a cyano group may be fused together to form a ring . Specifically, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

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 aryl 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 indenyl group, a substituted or unsubstituted furanyl 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 thiazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted acridinyl groups, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, Diary, or a combination thereof.

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]

Wherein X ¹ is N or CR ¹ , X ² is N or CR ² , X ³ is N or CR ³ , X ⁴ is N or CR ⁴ , X ⁵ is N or CR ⁵ , X ⁶ is N or CR ⁶ , X ⁷ is N or CR ⁷ , X ⁸ is N or CR ⁸ ,

R ¹ to R ⁸ and T each independently represent 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 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 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 aryloxy 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 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 to R ⁸ are each independently present, or two adjacent ones of R ¹ to R ⁸ are fused to each other to form a ring,

L is 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, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 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 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, or a combination thereof.

The compound according to one embodiment of the present invention may have a higher T 1 value by implementing a cubic structure of a carbazole structure, thereby having high efficiency, long life, and low voltage driving characteristics.

In addition, the compound represented by Formula 1 can be designed to have desired characteristics by introducing various substituents. For example, when T in the above formula (1) is a substituent having an electron characteristic, the compound can 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, Is a functional group having a hole property, the compound can be designed as a compound having a strong hole property.

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.

R ¹ to R ⁸ are each independently present, or two adjacent ones of R ¹ to R ⁸ are fused to each other to form a ring,

The ring may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted indolyl group.

For example, the formula (1) may be any one of the following formulas (2) to (19)

[Chemical Formula 3] [Chemical Formula 4] Chemical Formula 5 [Chemical Formula 6]

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[Chemical Formula 8] < EMI ID =

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[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15]

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[Chemical Formula 18] [Chemical Formula 18] [Chemical Formula 19]

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In the above Chemical Formulas 2 to 19,

X ¹ to X ⁸ , L and T are the same as defined in the above formula (1).

Further, the formula (1) may be any one of the following formulas (20) to (45):

[Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24]

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[Chemical Formula 25] [Chemical Formula 25]

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[Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34]

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[Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39]

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[Chemical Formula 40] [Chemical Formula 41]

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[Chemical Formula 44]

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In the above Chemical Formulas 20 to 45, T and L are as defined in Chemical Formula 1 above.

In Formula (1), T may be one of the substituted or unsubstituted functional groups listed in Group I below.

[Group I]

In said group I,

Each Z is independently N or CR ^a ,

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

Wherein R ^a to R ^f 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.

It may also be one of the substituted or unsubstituted functional groups listed in Group II below.

[Group II]

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In the group II,

W is O, S, NR ^g , or CR ^h R ⁱ ,

Wherein R 'and R ^g to R ⁱ 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 aryl 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 aryl 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 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 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 the connection point.

The L may be 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 anthracenylene group.

For example, one of the connectors listed below.

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Each of R ¹⁰⁰ to R ¹⁰³ is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl 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 C1 to C10 trifluoroalkyl group or a cyano group, and * is a connecting point.

The compounds according to one embodiment of the present invention may be one of the compounds listed in Group III below.

[Group III]

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In the group III,

L is a single bond,

T may be one of the moieties listed in Group IV below.

[Group IV]

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In the group IV,

* Is the connection point.

In one embodiment of the present invention, T represents a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalenylene group , A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted A substituted or unsubstituted dibenzothiopheny group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiopheny group, And may be a compound having a halogen atom.

Specific examples of the compound according to one embodiment of the present invention may include, but are not limited to, those listed in Group V below.

[Group V]

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The compounds of the present invention may also be compounds for organic optoelectronic devices.

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 of the present invention.

1, an organic light emitting device 100 according to an exemplary embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed 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: Synthesis of intermediate compound A

Intermediate Compound I-1 shown as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through the same route as the following reaction formula.

A first step; Synthesis of Intermediate Product (I-1)

                                           (I-1)

3.96 g (96.49 mmol) of lithium aluminum hydride was dissolved in 250 ml of methanol, 11.45 g (48.25 mmol) of n-benzylphthalimide was slowly added thereto, and the mixture was stirred at room temperature.

The reaction was terminated, and the organic solution was removed. The organic solution was dissolved in dichloromethane, filtered through silica, and recrystallized from n-hexane to obtain 5.50 g (26.47 mmol, yield: 55%) of the intermediate product (I-1).

A second step; Synthesis of Intermediate Product (II-1)

   (I-1) (II-1)

5.5 g (26.47 mmol) of the intermediate product (I-1), 4.63 g (26.47 mmol) of 2-bromobromobenzene and 0.064 g (2.65 mmol) of magnesium powder were suspended in 250 ml of tetrahydrofuran solvent, Lt; / RTI > The reaction is terminated and a silica gel filter is applied. The solvent was removed and recrystallization from dichloromethane and normal nucleic acid gave 4.10 g (14.47 mmol, yield: 55%) of the intermediate product (II-1).

A third step; Synthesis of Intermediate Product (III-1)

    (II-1) (III-1)

4.1 g (14.47 mmol) of the intermediate product (II-1), 5.15 g (28.93 mmol) of n-bromosuccinimide and 1.46 g (17.38 mmol) of sodium bicarbonate were dissolved in 200 ml of dioxane and refluxed for 8 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and the resulting product was recrystallized from dichloromethane and n-hexane to obtain a product (III-1) (3.0 g, 11.0 mmol, yield: 76%).

Step 4: Synthesis of intermediate compound (A)

   (III-1) (A)

3.0 g (11.0 mmol) of the intermediate product (III-1) was dissolved in 120 ml of methanol, 0.43 g (13.23 mmol) of hydrazine hydrate was slowly added thereto, and the mixture was refluxed under nitrogen stream for 12 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 resulting solid was recrystallized from dichloromethane and acetone to obtain 1.75 g (9.1 mmol, yield: 82%) of the intermediate compound (A).

Synthetic example  2: Synthesis of intermediate compound B

A first step; Synthesis of intermediate product (II-2)

     (I-1) (II-2)

6.25 g (30.0 mmol) of 1-bromo-2-fluoronaphthalene and 0.146 g (6.0 mmol) of magnesium powder were suspended in 300 ml of tetrahydrofuran solvent And reflux agitated for 18 hours. The reaction is terminated and a silica gel filter is applied. The solvent was removed and recrystallization from dichloromethane and normal nucleic acid yielded 5.30 g (14.47 mmol, yield: 53%) of the intermediate product (II-2).

A second step; Synthesis of Intermediate Product (III-2)

 (II-2) (III-2)

5.3 g (15.9 mmol) of intermediate (II-2), 5.7 g (31.79 mmol) of n-bromosuccinimide and 1.6 g (19.0 mmol) of sodium bicarbonate were dissolved in 250 ml of dioxane and refluxed for 8 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed, and the resulting product was recrystallized from dichloromethane and n-hexane to obtain a product (dichloromethane: n-hexane: 1: 9 v / v) 76%).

Step 3: Synthesis of intermediate compound (B)

 (III-2) (B)

4.0 g (12.04 mmol) of the intermediate product (III-2) was dissolved in 130 ml of methanol, 0.46 g (13.23 mmol) of hydrazine hydrate was slowly added thereto, and the mixture was refluxed under nitrogen stream for 12 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 product solid was recrystallized from dichloromethane and acetone to give 2.5 g (10.24 mmol, Yield: 85%) of intermediate compound (B).

Synthetic example  3: Synthesis of intermediate compound C

Step 1: Synthesis of intermediate product (C-a)

   (I-1) (C-a)

5.5 g (26.47 mmol) of intermediate product (I-1), 4.87 g (27.69 mmol) of 4-bromo-3-fluoropyridine and 0.064 g (2.65 mmol) of magnesium powder were suspended in 250 ml of tetrahydrofuran solvent And reflux agitated for 18 hours. The reaction is terminated and a silica gel filter is applied. The solvent was removed and recrystallization from dichloromethane and n-hexane gave 2.76 g (9.71 mmol, yield: 37%) of the intermediate product (Ca).

Step 2: Synthesis of intermediate product (C-b)

  (C-a) (C-b)

2.77 g (9.71 mmol) of the intermediate product (Ca), 3.45 g (19.40 mmol) of n-bromosuccinimide and 0.98 g (11.64 mmol) of sodium bicarbonate were dissolved in 100 ml of dioxane and refluxed for 8 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and the resulting product was recrystallized from dichloromethane and normal hexane to obtain 1.40 g (5.13 mmol, yield: 53%) of the intermediate product (Cb). The crude product was purified by silica gel column chromatography using dichloromethane and n-hexane in a ratio of 1: ).

Step 3: Synthesis of intermediate compound (C)

  (C-b) (C)

1.4 g (5.13 mmol) of the intermediate product (C-b) was dissolved in 60 ml of methanol, 0.196 g (6.12 mmol) of hydrazine hydrate was slowly added thereto, and the mixture was refluxed under nitrogen stream for 12 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 resulting solid was recrystallized from dichloromethane and acetone to obtain 0.68 g (3.5 mmol, yield: 68%) of Intermediate Compound (C).

Example  1: Synthesis of compound (A-1)

     (1) (A) (A-1)

4-bromophenyl-biphenyl-triazine (1) 11.64 g (30.0 mmol ), intermediate compound (A) 5.79 g (30.0 mmol ), NaO (t-Bu) 3.46g (36.0 mmol), Pd 2 (dba) 3 0.274 g (0.30 mmmol) was suspended in 300 ml of toluene, 0.20 ml (0.90 mmol) of tri-tert-butylphosphine was added thereto, and the mixture was refluxed with stirring for 18 hours.

After completion of the reaction, the reaction mixture was extracted with toluene and distilled water, and the organic layer was dried with magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (8: 2 by volume) and recrystallized from dichloromethane and ethyl acetate to give 10.2 g (yield 68%) of the target compound A-1. (LC mass measurement: 501 g / mol)

Example  2: Synthesis of compound (A-2)

     (2) (A) (A-2)

Synthesis was carried out in the same manner as in Example 1, except that the starting material was changed to the compound (2).

Example  3: Synthesis of compound (A-3)

       (3) (A) (A-3)

Synthesis was conducted in the same manner as in Example 1, except that the starting material was changed to the compound (3).

Example  4: Synthesis of compound (A-4)

      (4) (A) (A-4)

The synthesis was conducted in the same manner as in Example 1, except that the starting material was changed to the compound (4).

Example  5: Synthesis of compound (A-5)

    (5) (A) (A-5)

The synthesis was conducted in the same manner as in Example 1, except that the starting material was changed to the compound (5).

Example  6: Synthesis of compound (B-1)

     (4) (B) (B-1)

Synthesis was conducted in the same manner as in Example 1 except that the starting material compound (4) and the intermediate compound (B) were used.

Example  7: Synthesis of Compound (C-1)

    (4) (C) (C-1)

Synthesis was conducted in the same manner as in Example 1, except that the starting material compound (4) and the intermediate compound (C) were used.

(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 1 below.

compound Dipole Moment HOMO (eV) LUMO (eV) T1 (eV) S1 (eV) A-1 2.964 -5.46 -1.62 2.73 3.19 A-2 1.507 -5.46 -1.75 2.75 3.22 A-3 1.657 -5.47 -1.84 3.08 3.22 A-4 1.439 -5.43 -1.78 3.12 3.25 A-5 1.530 -5.37 -1.78 2.50 3.12 B-1 2.254 -5.61 -1.83 2.96 3.33 C-1 2.964 -5.46 -1.62 2.73 3.19

(Fabrication of organic light emitting device)

Example  8: Fabrication of organic light emitting device

The compound A-1 obtained in Example 1 was used as a host and Ir (PPy) ₃ was used as a dopant to prepare an organic light emitting device. 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 (naphthalen-1-yl) -N4 and N4'-diphenylbiphenyl-4,4'-diamine were added on the substrate at a vacuum degree of 650 × 10 ^-7 Pa and a deposition rate of 0.1 to 0.3 nm / (NPB) (80 nm) was deposited thereon to form a 800 Å hole transport layer. Subsequently, using the compound A-1 obtained in Example 1 under the same vacuum deposition conditions, a light emitting layer with a thickness of 300 A At this time, Ir (PPy) ₃ , which is a phosphorescent dopant, was simultaneously deposited. 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. 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 photoelectric device. The structure of the organic photoelectric device was ITO / NPB (80 nm) / EML (compound 1 (93 wt%) + Alq3 (20 nm) / LiF (1 nm) / Al (100 nm), Ir (PPy) ₃ (7 wt%), 30 nm) / Balq (5 nm)

Example  9

Example 1 An organic luminescent device was produced in the same manner as in Example 8 except that the compound (A-2) of Example 2 was used in place of the compound (A-1).

Example  10

Example 1 An organic luminescent device was manufactured in the same manner as in Example 8, except that the compound (A-3) of Example 3 was used in place of the compound (A-1).

Example  11

Example 1 An organic luminescent device was produced in the same manner as in Example 8, except that the compound (A-4) of Example 4 was used in place of the compound (A-1).

Example  12

Example 1 An organic luminescent device was prepared in the same manner as in Example 8, except that the compound (A-5) of Example 5 was used in place of the compound (A-1).

Example  13

Example 1 An organic light emitting device was produced in the same manner as in Example 8, except that the compound (B-1) of Example 6 was used in place of the compound (A-1).

Example  14

Example 1 An organic luminescent device was prepared in the same manner as in Example 8, except that the compound (C-1) of Example 7 was used in place of the compound (A-1).

Comparative Example  One

Example 1 An organic light emitting device was prepared in the same manner as in Example 8 except that CBP having the following structure was used instead of the compound (A-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)

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting device according to Examples 8 to 14 and Comparative Example 1 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 2.

(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 time at which the luminance (cd / m ² ) was maintained at 5000 cd / m ² and the current efficiency (cd / A) decreased to 90% was measured and the results were obtained.

No. The light- The driving voltage (V) color
(EL color) efficiency
(cd / A) 90% lifetime (h)
At 5000 cd / m ² Example 8 A-1 3.9 Green 51.9 120 Example 9 A-2 4.1 Green 53.3 140 Example 10 A-3 4.0 Green 61.4 350 Example 11 A-4 3.9 Green 69.2 380 Example 12 A-5 4.1 Green 49.2 110 Example 13 B-1 4.4 Green 57.0 240 Example 14 C-1 4.2 Green 55.5 100 Comparative Example 1 CBP 4.8 Green 31.4 40

As can be seen from Table 2, the organic light emitting devices of Examples 8 to 14 have improved characteristics in terms of driving voltage, luminous efficiency and / or power efficiency as compared with 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 (14)

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

In Formula 1,
X ¹ is N or CR ^1, and X ² is N or CR ^2, X ³ is N or CR ^3, X ⁴ is N or CR ^4, X ⁵ is N or CR ^5, X ⁶ is N or CR ⁶ , X ⁷ is N or CR ⁷ , X ⁸ is N or CR ⁸ ,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
R ¹ to R ⁸ are each independently present, or two adjacent ones of R ¹ to R ⁸ are fused to each other to form a ring,
T is a substituted or unsubstituted C3 to C30 heteroaryl group,
L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group. The method according to claim 1,
R ¹ to R ⁸ are each independently present, or two adjacent ones of R ¹ to R ⁸ are fused to each other to form a ring,
The ring may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, Lt; / RTI > is a substituted fluorenyl group. The method according to claim 1,
A compound represented by any one of the following formulas (2) to (19):
[Chemical Formula 3] [Chemical Formula 4] Chemical Formula 5 [Chemical Formula 6]

,

,

,

,

,
[Chemical Formula 8] < EMI ID =

,

,

,

,
[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15]

,

,

,

,

,
[Chemical Formula 18] [Chemical Formula 18] [Chemical Formula 19]

,

,

,

,
In the above Chemical Formulas 2 to 19,
X ¹ to X ⁸ , L and T are as defined in claim 1. The method according to claim 1,
A compound represented by any one of the following Chemical Formulas 20 to 45:
[Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24]

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,
[Chemical Formula 25] [Chemical Formula 25]

,

,

,

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,
[Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34]

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,

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,

,
[Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39]

,

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[Chemical Formula 40] [Chemical Formula 41]
,

,

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,
[Chemical Formula 44]

,

,
In the above Chemical Formulas 20 to 45, T and L are as defined in claim 1. The method according to claim 1,
Wherein T is one of the substituted or unsubstituted functional groups listed in group I below:
[Group I]

In said group I,
Each Z is independently N or CR ^a ,
At least one of Z is N,
W is O, S, NR ^b , or CR ^c R ^d ,
Wherein R ^a to R ^d 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,
* Is a connecting point and may be located in any of the elements forming the functional group. The method according to claim 1,
Wherein T is one of the substituted or unsubstituted functional groups listed in the following Group II:
[Group II]

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,

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,

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,

,

,
In the group II,
W is O, S, NR ^g , or CR ^h R ⁱ ,
Wherein R ', R ^g 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 C6 to C30 aryl groups, or substituted or unsubstituted C3 to C30 heteroaryl groups ego,
* Is the connection point. The method according to claim 1,
Wherein L is 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 anthracenylene group. The method according to claim 1,
A compound that is one of the compounds listed in Group III below:
[Group III]

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,
In the group III,
L is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,
T is one of the moieties listed in Group IV below:
[Group IV]

In the group IV,
* Is the connection point. The method according to claim 1,
Wherein T is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, A substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted benzothiazolyl group, Dibenzothiophen yl group. The method according to claim 1,
Wherein said compound is for an organic optoelectronic device. 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. 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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