KR101682020B1 - Compound, organic optoelectric device and display device - Google Patents

Abstract

(상기 화학식 1에서, X¹ 내지 X⁸의 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 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 that converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting diode usually has a structure in which an organic layer is interposed 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, an electron injecting layer, And at least one layer selected from the hole blocking layer.

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

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

High efficiency, long life, and the like.

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

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

[Chemical Formula 1]

In Formula 1,

이고, X²는 N 또는

이고, X³는 N 또는

이고, X⁴는 N 또는

이고, X⁵는 N 또는

이고, X⁶는 N 또는

이고, X⁷은 N 또는

이고, X⁸은 N 또는

이고,X ¹ is N or

, X < ² > is N or

, X < ³ > is N or

, X < ⁴ > is N or

, X < ⁵ > is N or

, X < ⁶ > is N or

, X < ⁷ > is N or

, X ⁸ is N or

ego,

L ¹ to L ⁸ each independently represent 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 a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, Or a substituted or unsubstituted C1 to C30 alkoxylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, Lt; / RTI >

R ¹ to R ⁸ 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 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 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

R ¹ to R ⁸ are each independently present or fused together to form a ring,

At least one of R ¹ to R ⁸ is a substituted or unsubstituted C3 to C30 heteroaryl group or a substituted or unsubstituted C5 to C40 fused ring.

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, Phenothiazine group, may be a substituted or unsubstituted phenoxazine group, or a combination thereof, are not limited.

In the present specification, the fused ring means a ring form in which two or more rings are formed by sharing two or more atoms. The fused ring may be aromatic or non-aromatic.

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

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

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

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

[Chemical Formula 1]

In Formula 1,

이고, X²는 N 또는

이고, X³는 N 또는

이고, X⁴는 N 또는

이고, X⁵는 N 또는

이고, X⁶는 N 또는

이고, X⁷은 N 또는

이고, X⁸은 N 또는

이고,X ¹ is N or

, X < ² > is N or

, X < ³ > is N or

, X < ⁴ > is N or

, X < ⁵ > is N or

, X < ⁶ > is N or

, X < ⁷ > is N or

, X ⁸ is N or

ego,

L ¹ to L ⁸ each independently represent 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 a substituted or unsubstituted C6 to C30 arylene group, 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 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, Lt; / RTI >

R ¹ to R ⁸ 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 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 to C20 A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group , A substituted or unsubstituted C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group , An amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof,

R ¹ to R ⁸ are each independently present or fused together to form a ring,

At least one of R ¹ to R ⁸ is a substituted or unsubstituted C3 to C30 heteroaryl group or a substituted or unsubstituted C5 to C40 fused ring.

At least one of R ¹ to R ⁸ of the compound according to one embodiment of the present invention includes a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted C5 to C40 fused ring, In the bipolar structure, the hole transporting ability and the electron transporting ability are simultaneously provided, so that it can have advantages of high efficiency and long life, and can be driven at low voltage.

In addition, the compound represented by Formula 1 can be designed to have desired characteristics by introducing various substituents. For example, when at least one of R ¹ to R ⁸ in the formula (1) is a substituent having an electron characteristic, the compound may be designed as a compound having a strong electronic characteristic. For example, at least one of R ¹ to R ⁸ in the formula In the case of a functional group having a characteristic, the compound may be designed as a compound having both ampholytic characteristics by including both a portion having an electron characteristic and a portion having a hole characteristic.

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

For example, each of R ¹ to R ⁸ is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing A cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

At least one of R ¹ to R ⁸ may be represented by a substituted or unsubstituted functional group of any one of the following formulas I-1 to I-4:

[I-1] [I-2] [I-3] [I-4]

In the formulas (I-1) to (I-4)

Y is _{N, O, S, SO 2} , NR, CR, SiR, CRR 'or SiRR'

Z is N, CR, CRR ', or NR, wherein at least one is N or NR,

Wherein R and R 'are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, 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 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 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 sulfonyl group, A substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof .

* Is a point connected to any one of L ¹ to L ⁸ in Formula 1 and may be located in any one of the functional elements. For example, a carbon or a heteroatom which constitutes the functional group or the substituent of the functional group.

Specifically, at least one of R ¹ to R ⁸ may be represented by any one of the following formulas (I-5) to (I-20).

[I-5] [I-6] [I-7] [I-8]

[I-10] [I-11] [I-12] [I-13] [I-

[I-15] [I-16] [I-17] [I-18]

[I-19] [I-20]

In the above Formulas I-5 to I-20,

* Is a point connected to any one of L ¹ to L ⁸ in Formula 1 and may be located in any one of the functional elements,

R, R ', and R ¹⁰⁰ to R ¹⁰³ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C2 to C30 hetero Aryl groups or combinations thereof.

이고, X²는

이고, X³는

이고, X⁴는

이고, X⁵는

이고, X⁶는

이고, X⁷은

이고, X⁸은

이고,For example, in Formula 1, X ¹ represents

And X ² is

And X ³ is

And X ⁴ is

And X ⁵ is

And X ⁶ is

And X < ⁷ >

And X ⁸ is

ego,

Wherein each of L ¹ to L ⁸ is, independently of each other, a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group,

Each of R ¹ to R ⁸ independently represents hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C40 silyl group, A substituted or unsubstituted C5 to C40 fused ring,

R ¹ to R ⁸ are each independently present or fused together to form a ring,

At least one of R ¹ to R ⁸ may be a substituted or unsubstituted C3 to C30 heteroaryl group, or a substituted or unsubstituted C5 to C40 fused ring.

Specifically, at least one of R ¹ to R ⁸ is selected from substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted fluorene, substituted or unsubstituted di Benzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazole.

Also, at least one of X ¹ to X ⁸ may be N, and specifically, at least one of X ¹ to X ⁴ may be N.

Wherein L ¹ to L ⁸ are both a single bond, among the adjacent R ¹ to R ⁸ R ² and R ^3, or R ⁷ and R ⁸ may form a ring fused to each other. For example, 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 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.

More specifically, R ² and R ³ , or R ⁷ and R ⁸ may be fused to each other and represented by the following formula (2) or (3).

[Chemical Formula 2] < EMI ID =

,

,

,

,

In the general formulas (2) and (3)

X ¹ to X ⁸ are each independently N or CR,

Wherein R is 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, substituted or unsubstituted C6 to C30 aryl groups , A substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 heteroarylamine group, Substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C2 to C30 alkoxycarbonyl groups, substituted or unsubstituted C2 to C30 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C30 aryloxycarbonylamino groups, substituted or unsubstituted A C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C40 silyl A substituted or unsubstituted C 1 to C 20 acyloxy group, a substituted or unsubstituted C 3 to C 40 acyloxy group, a substituted or unsubstituted C 1 to C 30 acyl group, a substituted or unsubstituted C 1 to C 20 acyloxy group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 sulfonyl group, A substituted or unsubstituted C1 to C30 ureide group, a substituted or unsubstituted C5 to C40 fused ring, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group , A carboxyl group, a ferrocenyl group, or a combination thereof.

In Formula 1, L ¹ to L ⁸ are linking groups connecting the substituents R ¹ to R ^8, and the conjugation length of the entire compound can be determined, and the triplet energy bandgap can be controlled therefrom . This makes it possible to realize the characteristics of the materials required in organic optoelectronic devices. Further, the triplet energy bandgap can be controlled by changing the bonding positions of ortho, para, and meta.

The L ¹ to L ⁸ may be, for example, a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C3 to C30 heteroarylene group.

When L ¹ to L ⁸ are a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted p-terphenylene group, a substituted or unsubstituted biphenylene group, A substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted pyrrolidinyl group, or a combination thereof.

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

[A-1] [A-2] [A-3] [A-4]

[A-6] [A-7] [A-8] [A-9]

[A-11] [A-12] [A-13] [A-14]

[A-16] [A-17] [A-18] [A-

[A-21] [A-22] [A-23] [A-24] [A-25]

[A-26] [A-27] [A-28] [A-29] [A-30]

[A-31] [A-32] [A-33] [A-34]

[A-36] [A-37] [A-38] [A-39]

[A-41] [A-42] [A-43] [A-44]

[A-46] [A-47] [A-48] [A-49]

[A-51] [A-52] [A-53] [A-54] [A-55]

[A-56] [A-57] [A-58] [A-59]

[A-61] [A-62] [A-63] [A-64] [A-65]

[A-66] [A-67] [A-68] [A-69]

[A-71] [A-72] [A-73] [A-74]

[A-76] [A-77] [A-78] [A-

[A-81] [A-82] [A-83] [A-84]

[A-86] [A-87] [A-88] [A-89]

[A-91] [A-92] [A-93] [A-

[A-96] [A-97] [A-98] [A-99]

[A-101] [A-102] [A-103] [A-104]

[A-106] [A-107] [A-108] [A-109]

[A-111] [A-112] [A-113] [A-114]

[A-116] [A-117] [A-118]

[A-121] [A-122] [A-123] [A-124]

[A-126] [A-127] [A-128] [A-129]

[A-131] [A-132] [A-133] [A-134]

[A-136] [A-137] [A-138] [A-139]

[A-141] [A-142] [A-143] [B-1] [B-

[B-3] [B-4] [B-5] [B-6]

[B-8] [B-9] [B-10] [B-11]

[B-13] [B-14] [B-15] [B-16]

[B-18] [B-19] [B-20] [B-21]

[B-23] [B-24] [B-25] [B-26]

[B-28] [B-29] [B-30] [B-31]

[B-33] [B-34] [B-35] [B-36]

[B-38] [B-39] [B-40] [B-41]

[B-43] [B-44] [B-45] [B-46]

[B-48] [B-49] [B-50] [B-51]

[B-53] [B-54] [B-55] [B-56]

[B-58] [B-59] [B-60] [B-61]

[B-63] [B-64] [B-65] [B-66]

[B-68] [B-69] [B-70] [B-71]

[B-73] [B-74] [B-75] [C-1] [C-2]

[C-3] [C-4] [C-5] [C-6]

[C-8] [C-9] [C-10] [C-11]

[C-13] [C-14] [C-15] [C-16]

[C-18] [C-19] [C-20] [C-21]

[C-23] [C-24] [C-25] [C-26]

[C-28] [C-29] [C-30] [C-31]

[C-33] [C-34] [C-35] [C-36]

[C-38] [C-39] [C-40] [C-41]

[C-43] [C-44] [C-45] [C-46]

[C-48] [C-49] [C-50] [C-51]

[C-53] [C-54] [C-55] [C-56]

[C-58] [C-59] [C-60] [C-61]

[C-63] [C-64] [C-65] [C-66]

[C-68] [C-69] [C-70] [C-71]

[C-73] [C-74] [C-75] [C-76]

[C-78] [C-79] [C-80] [C-81]

[C-83] [C-84] [C-85] [C-86]

[C-88] [C-89] [C-90] [C-91]

[C-93] [C-94] [C-95] [C-96]

[C-99] [C-100] [C-101] [C-102]

[C-104] [C-105] [C-106] [C-107]

[C-109] [C-110] [C-111]

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

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

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

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

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

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

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

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

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

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

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole assist layer 140 in addition to the light emitting layer 230. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block 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)

Synthesis of compounds for organic optoelectronic devices

[Formula 1]

(In the above Reaction Scheme 1, X ¹ to X ⁸ are as defined in Formula 1, and "pro" is an aryl group, a benzyl group, a benzyloxymethyl group, a paramethoxybenzyl group or a methoxymethyl group as a protecting group, Is a para-methoxybenzyl group or a methoxymethyl group.)

Each step will be described in detail as follows.

Step 1 : A commercially available 2-chloronicotic acid (A) is prepared by reacting a carboxylic acid such as thionyl chloride or oxalyl chloride with an acid chloride Chloric acid is prepared using a changing reagent. This reaction is carried out using a solvent such as dichloromethane, chloroform or toluene which does not use a solvent or adversely affect the reaction. The reaction temperature is not particularly limited, but it can be generally carried out at room temperature to warming, preferably at a temperature. Compounds of formula (B) are prepared by the general amidation reaction with substituted anilines at the meta and / or para positions of the resulting acid chloride (3). This reaction can be carried out without using a base, but it is generally carried out in the presence of an organic amine such as pyridine, triethylamine or diethylisopropylamine, which is a base which can be used for the amidation reaction, in dichloromethane, The reaction is carried out using chloroform, tetrahydrofuran, diethyl ether, toluene, N, N-dimethylformamide or the like. The reaction temperature is not particularly limited, but it can be generally carried out at a room temperature to a warm temperature, preferably at a warm temperature.

Step 2 : The N-protected amide intermediate (C) is synthesized by introducing a protecting group into the compound of formula (B) prepared in step 1 above. Examples of the protection group include alkoxymethyl such as methoxymethyl (MOM), benzyloxymethyl (BOM), or benzyl (Bn) or p-methoxybenzyl (PMB) Can be introduced. The base used in this reaction is a reaction carried out using sodium hydride, potassium t-butoxide, potassium carbonate, etc. The solvent is tetrahydrofuran Furan, N, N-dimethylformamide, acetonitrile, toluene and the like are used. The reaction temperature is not particularly limited, but it can be generally carried out at a room temperature to a warm temperature, preferably at a warm temperature.

Step 3 : The N-protected amide intermediate (C) prepared in the second step is subjected to a cyclization reaction under a metal-catalyst to prepare a lactam having the formula (D). For this reaction the metal-catalyst is typically a palladium (Pd (0)) is used, and tetrakis (triphenylphosphine) palladium (Pd (0)) (tetrakistriphenylphosphine , (PPh 3) 4 Pd), palladium acetate (Ⅱ) (Pd (OAc) ₂ ), tris (dibenzilideneacetone) (0), (Pd2dba3) and bis (triphenylphosphine) palladium (II) chloride triphenylphosphine) palladium (II), and (PdCl ₂ (PPh ₃ ) ₂ )) can be used alone or in combination with tributylphosphine (Bu ₃ P). This reaction can be carried out without the use of a ligand, but generally the ligand used in the cyclization reaction under metal-catalyst is triphenylphosphine (PPh ₃ ) ₄ , Bis (diphenylphosphino) propane, DPPP), (R) -2,2'-bis (diphenylphosphino) -1,1'-binaphthyl ( R) -2,2'-bis (diphenylphosphino) -1,1'-binaphthyl, (R) -BiNAP). The base which can be used herein is potassium carbonate, sodium carbonate, silver carbonate, diethyl isopropylamine and the like. The reaction is carried out using a solvent such as N, N-dimethylformamide, benzene, xylene or acetonitrile which does not cause a side reaction . The reaction temperature is not particularly limited, but in general, the reaction can be carried out at a room temperature to a warming temperature, preferably at a heating temperature.

Step 4 : The piperidine-lactam (D) prepared in Step 3 is deprotected by a method known in general organic synthesis to prepare the tricyclic compound of Formula (E).

Step 5 : The tricyclic compound (E) prepared in Step 4 is subjected to a reduction reaction by a method known in general organic synthesis to prepare a compound (F) in the form of naphthyridine.

Hereinafter, preferred embodiments and experimental examples are provided to facilitate understanding of the present invention. However, the following examples and experimental examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the examples.

Synthetic example  1: Synthesis of compound (A-40)

The compound (A-40) shown as a more specific example of the compound for an organic optoelectronic device of the present invention was synthesized through a six-step route as shown in the following Reaction Scheme 1.

[Reaction Scheme 1]

　　

Step 1: Synthesis of intermediate product (B)

Anhydrous dichloromethane (800 ml) was added to 2-chloronicotinic acid (A) (30 g, 190.42 mmol), and then oxalyl chloride (24.17 ml, 209.46 mmol) was added dropwise at room temperature. After dropwise addition of anhydrous dimethylformamide, the mixture was stirred at room temperature for 3 hours. After confirming the completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain an intermediate 2-chloronicotinic chloride, which was dissolved in anhydrous dichloromethane (700 ml). Aniline (19.5 g, 209.46 mmol) was diluted with anhydrous dichloromethane (100 ml) . Triethylamine (52.8 ml, 380.83 mmol) was added to the reaction solution, and the mixture was stirred at 0 ° C for 1 hour. After completion of the reaction, water and dichloromethane were added. The separated organic layer was dried over anhydrous magnesium sulfate, and then the solvent was concentrated under reduced pressure to obtain the title compound (40 g, 90%).

Step 2: Synthesis of intermediate product (C)

The compound (B) (40 g, 171.92 mmol) prepared in the above step 1 was dissolved in N, N-dimethylformamide, cooled at 0 캜, and sodium hydride (8.24 g, 343.83 mmol) was added thereto and stirred for 30 minutes. Methoxymethyl bromide (21 ml, 257.88 mmol) was slowly added dropwise to the reaction solution, stirred for an hour, and water was slowly added to terminate the reaction. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (hexane: ethyl acetate = 2: 1) to give a residue. The residue was purified by silica gel column chromatography To give the title compound (36 g, 83%).

Step 3: Synthesis of intermediate product (D)

The compound (C) (36 g, 93.06 mmol) prepared in the above step 2 was dissolved in N, N-dimethylformamide, and palladium (II) acetate (1 g, 4.65 mmol) and PCy ₃ -HBF ₄ (3.6 g, 9.31 mmol ) And potassium carbonate (25.7 g, 186.12 mmol) were added in this order, followed by reflux stirring for 13 hours. Water was added to the reaction mixture to terminate the reaction, and the mixture was extracted with chloroform. The organic solvent layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane: ethyl acetate = 3: 1) To give the title compound (22 g, 67%).

Step 4: Synthesis of intermediate product (E)

The compound (D) (22 g, 91.56 mmol) prepared in the above Step 3 was dissolved in ethanol (200 ml), 12 N hydrochloric acid solution (100 ml) was added and the mixture was refluxed at 90 ° C for 12 hours. After the reaction was completed, NaOH aqueous solution was added to neutralize the reaction mixture, and then extracted with chloroform and water. The organic layer was concentrated under reduced pressure, and the residue was recrystallized from dichloromethane and hexane to obtain the title compound (15.4 g, 83%).

Step 5: Synthesis of intermediate product (F)

The compound (E) (15 g, 76.53 mmol) prepared in the above step 4 was dissolved in POCl ₃ and refluxed at 90 ° C for 12 hours. Then, when the reaction is completed, it is put into ice water to form a solid. After stirring at 0 ° C for 2 hours, the mixture was vacuum filtered and dried to obtain the title compound (13 g, 68%).

Step 6: Synthesis of Compound A-40

(10 g, 46.72 mmol), 3- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid (20.3 g, 56.06 mmol), tetrakispalladium 1.62 g, 1.40 mmol) was suspended in tetrahydrofuran (350 ml), potassium carbonate (12.9 g, 93.46 mmol) dissolved in water (115 ml) was added and the mixture was stirred under reflux for 12 hours. When the reaction is completed, water is added and the tetrahydrofuran layer is separated and concentrated under reduced pressure. Recrystallization from dichloromethane and acetone gave Compound A-40 (15.1 g, 65%).

Synthetic example  2: Synthesis of compound (A-52)

The compound (A-52) shown as a more specific example of the compound for an organic optoelectronic device of the present invention was synthesized through a one-step route like the following reaction formula.

　　

Step 1: Synthesis of compound (A-52)

(3-dibenzo [b, d] thiophen-4-yl) phenyl) boronic acid (10 g) synthesized in the fifth step of Reaction Scheme 1 and 10 g of 3-dibenzo [ -yl) phenyl) boronic acid (17.0 g) was obtained in the same manner as in Step 6 of Scheme 1 above to give 12.9 g (Yield: 63%) of Compound A-52.

Synthetic example  3: Synthesis of compound (A-50)

As a more specific example of the compound for organic optoelectronic devices of the present invention, A-50 was synthesized through a one-step route as shown in the following scheme.

　

Step 1: Synthesis of compound (A-50)

Dibenzo [b, d] furan-4-yl) phenyl) boronic acid (10 g) obtained in the fifth step of Reaction Scheme 1 and 10 g of 3-dibenzo [ yl) phenyl) boronic acid (16.1 g) was obtained in the same manner as in Step 6 of Scheme 1 to obtain 14.0 g (Yield: 71%) of Compound A-50.

Synthetic example  4: Synthesis of compound (A-38)

The compound (A-38) presented as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through a one-step route as shown in the following reaction formula.

　

Step 1: Synthesis of compound (A-38)

10 g of the intermediate (F) synthesized in the fifth step of the above reaction scheme 1 and 10 g of 3-9,9-dimethyl-9H-fluoren-2-yl) phenylvoronic acid ((3- fluoren-2-yl) phenyl) boronic acid (16.1 g) was obtained in the same manner as in Step 6 of Scheme 1 above to give 12.0 g (Yield: 68%) of Compound A-38.

Synthetic example  5: Synthesis of compound (A-56)

The compound (A-56) presented as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through a six-step route as shown in the following reaction formula.

Step 1: Synthesis of intermediate product (K)

Anhydrous dichloromethane (1050 ml) was added to 2-chloronicotinic acid (A) (40 g, 253.90 mmol), and oxalyl chloride (32.23 ml, 279.28 mmol) was added dropwise at room temperature. After dropwise addition of anhydrous dimethylformamide, the mixture was stirred at room temperature for 3 hours. After confirming the completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain an intermediate 2-chloronicotinyl chloride, which was dissolved in anhydrous dichloromethane (950 ml). 4-Aminopyridine (26.0 g, 276.26 mmol) was diluted with anhydrous dichloromethane Lt; / RTI > Triethylamine (70.4 ml, 507.77 mmol) was added to the reaction solution, and the mixture was stirred at 0 ° C for 1 hour. After completion of the reaction, water and dichloromethane were added, and the separated organic layer was dried over anhydrous magnesium sulfate, and then the solvent was concentrated under reduced pressure to obtain the title compound (48 g, 81%).

Steps 2, 3, 4, and 5: Synthesis of intermediate product (O)

48 g of the compound (K) prepared in the above Step 1 was subjected to the same procedures as in Steps 2, 3, 4 and 5 of Scheme 1 to obtain 15.2 g of the title compound (O).

Step 6: Synthesis of compound (A-56)

(10 g, 46.37 mmol), 3- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid (20.2 g, 55.65 mmol), tetrakispalladium 1.61 g, 1.39 mmol) was suspended in tetrahydrofuran (350 ml), potassium carbonate (12.4 g, 92.88 mmol) dissolved in water (115 ml) was added and the mixture was stirred under reflux for 12 hours. When the reaction is completed, water is added and the tetrahydrofuran layer is separated and concentrated under reduced pressure. Recrystallization from dichloromethane and acetone gave Compound A-56 (13.1 g, 57%).

(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 LUMO T1 S1 A-40 3.4927 -5.282 -1.681 2.7002 3.2244 A-52 2.0761 -5.689 -1.749 2.7043 3.5055 A-50 1.9075 -5.881 -1.710 2.7112 3.7178 A-38 1.4272 -5.583 -1.743 2.6955 3.4411 A-56 6.4491 -5.363 -2.003 2.7836 2.9864

(Fabrication of organic light emitting device)

Example  One

An organic light emitting device was fabricated using the compound (A-40) obtained in Synthesis Example 1 as a host and Ir (PPy) ₃ as a dopant.

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

N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diaminodiphenylsulfonate was deposited on the substrate at a vacuum degree of 650 × 10-7 Pa and a deposition rate of 0.1 to 0.3 nm / - diamine (NPB) (80 nm) was deposited on the hole transport layer to form a hole transport layer having a thickness of 800 ANGSTROM. Subsequently, a light emitting layer having a thickness of 300 angstroms was formed using the compound (A-40) obtained in Synthesis Example 1 under the same vacuum deposition condition. Ir (PPy) ₃ , which is a phosphorescent dopant, was simultaneously deposited thereon. At this time, the deposition rate of the phosphorescent dopant was adjusted so that the phosphorescent dopant content was 7% by weight when the total amount of the light emitting layer was 100% by weight.

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

The structure of the organic optoelectronic device was ITO / NPB (80 nm) / EML (compound A-40 (93 wt%) + Ir (PPy) ₃ (7 wt%), 30 nm) / Balq Alq3 (20 nm) / LiF (1 nm) / Al (100 nm).

Example  2

Synthesis Example 1 An organic luminescent device was produced in the same manner as in Example 1 except that the compound (A-52) was used in place of the compound (A-40).

Example  3

Synthesis Example 1 An organic light emitting device was prepared in the same manner as in Example 1 except that the compound (A-50) was used in place of the compound (A-40).

Example  4

Synthesis Example 1 An organic luminescence device was prepared in the same manner as in Example 1, except that the compound (A-38) was used instead of the compound (A-40).

Example  5

Synthesis Example 1 An organic luminescent device was prepared in the same manner as in Example 1, except that the compound (A-56) in Synthesis Example 5 was used instead of the compound (A-40).

Comparative Example  One

Synthesis Example 1 An organic light emitting device was prepared in the same manner as in Example 6 except that CBP having the following structure was used instead of the compound (A-40).

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 luminous efficiency of the organic light emitting device according to Examples 1 to 5 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 1 A-40 3.6 Green 76.5 200 Example 2 A-52 3.9 Green 68.6 140 Example 3 A-50 3.7 Green 66.1 140 Example 4 A-38 3.7 Green 70.8 170 Example 5 A-56 4.2 Green 54.5 145 Comparative Example 1 CBP 4.8 Green 31.4 40

As can be seen from Table 2, the OLEDs of Examples 1 to 5 exhibited 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 (15)

A compound for an organic optoelectronic device represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
X ¹ is

ego,
X ² is

ego,
X ³ is

ego,
X ⁴ is

ego,
X ⁵ is

ego,
X ⁶ is

ego,
X ⁷ is

ego,
X ⁸ is

ego,
L ¹ to L ⁸ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
At least one of R ¹ to R ⁸ is selected from substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran, substituted Or unsubstituted dibenzothiophene, or a substituted or unsubstituted carbazole. The method according to claim 1,
At least one of R ¹ to R ⁸ is a substituted or unsubstituted functional group of any one of the following formulas (I-1) to (I-4):
[I-1] [I-2] [I-3] [I-4]

In the formulas (I-1) to (I-4)
Y is N, O, S, or CRR '
Z is N, or CR, at least one is N,
Wherein R and R '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, substituted or unsubstituted C3 to C30 heteroaryl groups, ego,
* Is a point connected to one of L ¹ to L ⁸ in Formula 1 and is located at any one of the functional elements. The method according to claim 1,
At least one of R ¹ to R ⁸ is represented by a functional group of any of the following formulas I-5 to I-14, I-17, I-19 and I-20:
[I-5] [I-6] [I-7] [I-8]

[I-10] [I-11] [I-12] [I-13] [I-

[I-17]

[I-19] [I-20]

In Formulas I-5 to I-14, I-17, I-19 and I-20,
* Is a point connected to any one of L ¹ to L ⁸ in the formula (1) and is located in any one of the functional elements,
R, R ', and R ¹⁰⁰ to R ¹⁰³ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl, Or a combination thereof. delete delete delete delete delete delete delete 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 3. 12. The method of claim 11,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound. 13. The method of claim 12,
Wherein the compound is included as a host of the light emitting layer. 12. The method of claim 11,
Wherein the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer,
Wherein the auxiliary layer comprises the compound. 12. A display device comprising the organic electroluminescent device according to claim 11.

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