KR20140087987A - COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC LiGHT EMITTING DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LiGHT EMITTING DIODE - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectronic device, an organic light emitting diode including the same, and a display device including the organic light emitting diode. The present invention provides a compound for an organic optoelectronic device represented by chemical formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device. BACKGROUND ART [0002]

A compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device.

An organic optoelectronic device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electronic device.

The second type is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with an electrode by applying a voltage or current to two or more electrodes and operated by injected electrons and holes.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting devices, organic solar cells, organic photo conductor drums, and organic transistors, all of which are used for the injection or transport of holes, An injection or transport material, or a luminescent material.

In particular, organic light emitting diodes (OLEDs) have been attracting attention in recent years as the demand for flat panel displays increases. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

Such an organic light emitting device is a device that converts electric energy into light by applying an electric current to an organic light emitting material, and is usually composed of a structure in which a functional organic layer is interposed between an anode and a cathode. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected into the anode and electrons are injected into the organic layer through the cathode, and injected holes and electrons are recombined Energy excitons are formed. At this time, the exciton formed again moves to the ground state, and light having a specific wavelength is generated.

In recent years, it is known that not only a fluorescent light emitting material but also a phosphorescent emitting material can be used as a light emitting material of an organic light emitting device. Such phosphorescent emitting is a phenomenon in which electrons transition from a ground state to an excited state, cross-linking of the triplet exciton to the triplet exciton, and then the triplet exciton transitions to the ground state.

As described above, a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system can be used as a light emitting material in order to increase the light emitting efficiency and stability through the light emitting layer.

In order for the organic luminescent device to fully exhibit the above-described excellent characteristics, a host material and / or a dopant such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, an electron injecting material, The organic material layer for organic light emitting devices has not been sufficiently developed yet. Therefore, development of new materials has been continuously required. The necessity of developing such a material is the same in other organic optoelectronic devices described above.

In addition, the low-molecular organic light-emitting device has good efficiency and long life performance because it is manufactured in the form of a thin film by a vacuum deposition method. The polymer organic light-emitting device uses an inkjet or spin coating method, There is an advantage that the large area is advantageous.

Low molecular organic light emitting devices and polymer organic light emitting devices are attracting attention as next generation displays because they have advantages such as self-emission, fast response, wide viewing angle, ultra-thin, high image quality, durability and wide driving temperature range. Compared to conventional liquid crystal displays (LCDs), it is self-luminous and has good visibility even when dark or external light enters. It can reduce thickness and weight to 1/3 of that of LCD without backlight.

In addition, the response speed is 1000 times faster than that of LCD, so it is possible to realize perfect video without residual image. Therefore, it is anticipated that it will be seen as an optimal display in accordance with the multimedia age in recent years. Based on these advantages, after the first development in the late 1980s, the technology has been rapidly developed 80 times and lifespan 100 times. And organic light-emitting device panels have been announced, and the size of the organic light-emitting device panel is rapidly increasing.

In order to increase the size, it is necessary to increase the luminous efficiency and the lifetime of the device. Therefore, it is necessary to develop a stable and efficient organic material layer material for an organic light emitting device.

And which can provide an organic optoelectronic device having characteristics such as high efficiency, long life, and the like.

An organic light emitting device including the compound for an organic optoelectronic device, and a display device including the organic light emitting device.

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

[Chemical Formula 1]

In the above formula (1), the definition of each substituent is as described in the following "Detailed Description of the Invention ".

In another embodiment of the present invention, there is provided an organic light emitting device comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the compound do.

In another embodiment of the present invention, there is provided a display device including the organic light emitting element.

The organic optoelectronic device including the compound for an organic optoelectronic device has excellent electrochemical and thermal stability, has excellent lifetime characteristics, and can have a high luminous efficiency even at a low driving voltage.

FIG. 1 and FIG. 2 are cross-sectional views illustrating various embodiments of an organic light emitting device that can be manufactured using a compound for an organic optoelectronic device 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 C3 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 .

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.

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined.

The alkyl group may be an alkyl group of C1 to C20. 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" means a substituent in which all the elements of the cyclic substituent have p-orbital, and these p-orbital forms conjugation, and monocyclic or fused ring polycyclic , Rings that divide adjacent pairs of carbon atoms) functional groups.

"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 aryl group and / or the substituted or unsubstituted heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m- A phenyl 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 triazolyl group, a substituted or unsubstituted oxazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, A substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazyl group, Or an unsubstituted phenoxyl group, or a combination thereof, but is not limited thereto.

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. More specifically, it may be similar to the characteristic of pushing electrons.

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. More specifically, it may be similar to the characteristic of attracting electrons.

According to one embodiment of the present invention, a compound for organic optoelectronic devices represented by the following Chemical Formula 1 can be provided.

[Chemical Formula 1]

In Formula 1, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and L ¹ to L ³ independently of one another are substituted or unsubstituted A substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and n1 A3, A3, A3, A3, A3, A3, A3, A3, A3, A3, A3 and A3 are independently of each other an integer of 0 to 3, RTI ID = 0.0 > C2-C30 < / RTI >

[A-2]

In Formula (A-2), X ¹ is -O- or -S-, and R ³ and R ⁴ are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, A substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryl Oxycarbonylamino A substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted Or an unsubstituted C1 to C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

The compound represented by Formula 1 may have an amine group having a substituent including an indeno structure as a core structure. In the case of such a core structure, a substituent capable of exhibiting hole characteristics in the structure of Ar ¹ may have a structure capable of easily flowing electrons or holes while being combined with the amine group core. The substituent of the indeno structure is a structure having a non-covalent electron pair, which improves the flow of electrons or holes and is suitable as an evaporation material because of its small molecular weight. Generally, in the case of vapor-deposited materials, if the molecular weight exceeds 1000, heat stability problems may be caused. In the case of a structure to be substituted with Ar ¹ , it is characterized by having an abundance of electrons (rich in pi bonds, electron-donating group). The substituent of the amine structure is a structure in which electrons of Ar ¹ are attracted withdraw group), which can prevent the electron partialization in the compound, resulting in high efficiency and long life of the device.

The compound for organic optoelectronic devices represented by Formula 1 may be a compound having various energy bandgaps by introducing various substituents to the substituents of the core portion and the core portion.

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.

More specifically, in one embodiment of the present invention, 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 naphtha A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, Substituted or unsubstituted m-terphenyl groups, substituted or unsubstituted chrysenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted 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 furanyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, Substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, A substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazine Group, it may be a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxazine group, or a combination thereof, are not limited.

In addition, the conjugation length of the entire compound can be determined by selectively controlling the L ¹ to L ³ , 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 position of the ortho, para, and meta.

Specific examples of L ¹ to L ³ include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-tert A phenyl group, a substituted or unsubstituted perylenyl group and the like.

More specifically, L ¹ to L ³ may be, independently of one another, a phenylene group. In the case where L ¹ to L ³ are phenylene groups, both side core portions may be bonded to ortho, meta or para to the phenylene group.

The above B may be represented by the following formula (A-2). The above formula (A-2) has a non-covalent electron pair and can improve the flow of electrons or holes, thereby making it possible to produce a highly efficient device. In addition, since the molecular weight is smaller than that of dibenzofuran or dibenzothiophene which is generally used, it can be advantageous as a deposition material. In addition, the electron (pie bond, electron donor group) biased to Ar ¹ may be uniformly distributed throughout the compound by the withdrawing group of the above formula (A-2), so that a device with high efficiency / long life can be produced. More specifically, when the compound for an organic optoelectronic device includes two indeno structures, the electrons can be evenly distributed.

More specifically, Ar ¹ may be represented by the following formula (B-1).

[Formula B-1]

R ⁵ to R ⁸ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

In this case, in the case of a fluorene group such as the formula (B-1), the structure in which the carbon (C) is absent from the double bond results in breaking of the pi bond. Hence, it is easy to form holes and can be harmonized with the substituent of the indeno structure centered on amine (N). In order to transfer electrons or holes well, a substituent that can form a hole well and a substituent that forms an electron well must be well matched. The fluorene group is a substituent capable of forming a hole well. In the case of a fluorene-containing compound, the characteristics of the device can be improved in terms of high efficiency and driving voltage.

For example, Ar ¹ may be represented by the following formula (B-2).

[Formula B-2]

R ⁵ to R ⁸ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

The substituent represented by the above formula (B-2) may be bonded to amine nitrogen which is a core at a position where synthesis is easy.

More specifically, Ar ¹ may be represented by the following formula (B-3).

[Formula B-3]

R ⁹ to R ¹² independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

When a phenanthrene group such as the above-described formula B-3 is present, a lower HOMO level can be achieved. Further, the phenanthrene (B-2) group is known to have a structure in which three phenyl groups are bended to facilitate formation of holes. Compared to the fluorene (B-1) group, it has superior thermal stability (the resonance structure of both phenyl groups).

More specifically, Ar ¹ may be represented by the following formula (B-4).

[Formula B-4]

More specifically, when a lower HOMO level than the phenanthrene (formula B-2) group is required, it can be controlled by introducing triphenylene (formula B-3) group. The triphenylene group can provide a donor group due to the gathering of three phenyl groups. When the triphenylene group is bonded to a withdrawing group (for example, an indeno substituent), it is easy to form a hole Can be one structure. Compared to the fluorene group, it has excellent thermal stability (the resonance structure of both phenyl groups).

More specifically, Ar ¹ may be represented by the following formula (B-5).

[Formula B-5]

In the above formula (B-5), X ² is -O-, -S- or NR ', and R', R ¹³ and R ¹⁴ independently represent hydrogen, deuterium, a halogen group, a cyano group, , A substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 A substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, A substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, Gt; C7-C20 < / RTI > aryloxycarbo An amino group, a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted Or an unsubstituted C1 to C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

When a compound of the above formula (B-5) having good hole-transporting or electron-transporting ability is used, a high-efficiency device can be produced.

More specifically, Ar ¹ may be represented by the following formula (B-6).

[Formula B-6]

R ¹⁵ and R ¹⁶ are independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C20 heterocyclythiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof.

In the case of the carbazole group represented by the above formula (B-6), the pi bond is broken around the amine (N) to form a hole, and the hole transporting ability is also excellent because it has a non-covalent electron pair. Since the hole transporting ability of the carbazole group represented by the above formula (B-6) is very superior to the electron transporting ability, when it is used as a host for the hole transport layer, the hole transport layer, or the hole transporting layer, it is possible to realize a high efficiency low voltage device .

More specifically, Ar ¹ may be a substituted or unsubstituted biphenyl group. More specifically, for example, Ar ¹ may be represented by the following formula (B-7) or (B-8).

[Formula B-7] [Formula B-8]

The B-7 and / or B-8 substituents of the simpler structure are excellent in thermal and electrical stability and are suitable for realizing high-definition devices.

For example, A and B may be represented by the above formula (A-2). That is, when the substituent represented by the formula (A-2) is present simultaneously in the core amine group, the driving voltage of the device is lowered and the efficiency can be increased due to the presence of the formula (A-2) having excellent hole or electron transportability. The above formula (A-2) has a simple molecular structure and is excellent in thermal and electrical stability.

In the above formula (A-2), R ³ and R ⁴ may be hydrogen, but are not limited thereto.

The compound for an organic optoelectronic device may have a molecular weight of 700 or less. More specifically, it may have a molecular weight of 600 or less. In this case, since the deposition can be performed at a low temperature in the production of a device, deposition is easy and thermal stability can be increased. From this, the stability of the device can be improved.

Specific examples of the embodiment of the present invention include the following compounds. However, the present invention is not limited thereto.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, And a compound for an organic electroluminescent device.

The compound for an organic optoelectronic device is used in an organic thin film layer to improve lifetime characteristics, efficiency characteristics, electrochemical stability and thermal stability of an organic optoelectronic device, and can lower a driving voltage.

The organic thin film layer may be a light emitting layer.

The organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photoconductor drum, or an organic memory device.

More specifically, the organic optoelectronic device may be an organic light emitting device. 1 and 2 are sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.

1 and 2, organic light emitting devices 100 and 200 according to an embodiment of the present invention include an anode 120, a cathode 110, and at least one organic thin film layer interposed between the anode and the cathode. (105).

The anode 120 includes a cathode material. As the anode material, a material having a large work function is preferably used to facilitate injection of holes into the organic thin film layer. Specific examples of the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof and zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide ), And combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb, and poly (3-methylthiophene), poly (3,4- (ethylene- 2-dioxythiophene (PEDT), polypyrrole, and polyaniline, but the present invention is not limited thereto. Preferably, a transparent electrode including ITO (indium tin oxide) may be used as the anode.

The cathode 110 includes a cathode material, and the anode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium and the like, , LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca. However, the present invention is not limited thereto. Preferably, a metal electrode such as aluminum or the like may be used for the negative electrode.

1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 is present as an organic thin film layer 105. The organic thin film layer 105 may exist only in the light emitting layer 130. FIG.

2 illustrates a two-layer organic light emitting device 200 having a light emitting layer 230 including an electron transporting layer and a hole transporting layer 140 as an organic thin film layer 105. As shown in FIG. 2, Similarly, the organic thin film layer 105 may be of a two-layer type including a light emitting layer 230 and a hole transporting layer 140. In this case, the light emitting layer 230 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve the bonding property with a transparent electrode such as ITO and the hole transporting property. In one embodiment of the present invention, the organic thin film layer 105 may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like, as shown in FIG. 1 or FIG.

The light emitting layers 130 and 230, the hole transporting layer 140, or the electron transporting layer, the electron injecting layer, the hole injecting layer, and a combination of the electron transporting layer, the electron injecting layer, and the hole injecting layer, which are not shown in FIG. 1 or 2, Any one selected from the group includes the compound for the organic optoelectronic device.

In particular, the compound for the organic optoelectronic device can be used for the light emitting layers 130 and 230, and can be used as a green phosphorescent dopant material in the light emitting layer.

The organic light emitting device described above may be formed by a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating after an anode is formed on a substrate; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode on the organic thin film layer.

In another embodiment of the present invention, there is provided a display device including the organic light emitting element.

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: Preparation of intermediate I-1

After dissolving 1-bromo-4-chlorobenzene (53.7 g, 280.7 mmol) in 0.5 L of tetrahydrofuran (THF) in a nitrogen atmosphere, 2-benzofuranylboronic acid (50.0 g, 308.7 mmol) Tetrakis (triphenylphosphine) palladium (16.2 g, 14.0 mmol) was added and stirred. Saturated potassium carbonate (82.7 g, 561.4 mmol) in water was added and the mixture was refluxed by heating at 100 占 폚 for 47 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM). The extract was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-1 (50.8 g, 79%).

HRMS (70 eV, EI +): m / z calcd for C14H9ClO: 228.0342, found: 228.

Elemental Analysis: C, 74%; H, 4%

Synthetic example  2: Preparation of intermediate I-2

Bromo-4-chlorobenzene (48.9 g, 255.3 mmol) was dissolved in 0.5 L of THF in a nitrogen atmosphere. Thereto was added benzothiophen-2-yl-boronic acid (50.0 g, 280.9 mmol) (Triphenylphosphine) palladium (8.85 g, 7.66 mmol) was added thereto and stirred. Saturated potassium carbonate (75.2 g, 510.6 mmol) in water was added and the mixture was refluxed by heating at 80 占 폚 for 17 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-2 (61.3 g, 98%).

HRMS (70 eV, EI +): m / z calcd for C14H9ClS: 224.0113, found: 224.

Elemental Analysis: C, 69%; H, 4%

Synthetic example  3: Preparation of intermediate I-3

1-Bromo-4-nitrobenzene (50 g, 247.5 mmol) was dissolved in 0.5 L of THF in a nitrogen atmosphere, and thereto was added 9,9-dimethyl-9H- , 297.0 mmol) and tetrakis (triphenylphosphine) palladium (8.58 g, 7.43 mmol) were added and stirred. Saturated potassium carbonate (72.9 g, 495.0 mmol) in water was added and the mixture was refluxed by heating at 80 占 폚 for 21 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-3 (78.1 g, 82%).

HRMS (70 eV, EI +): m / z calcd for C21H17NO2: 315.1259, found: 315.

Elemental Analysis: C, 80%; H, 5%

Synthetic example  4: Preparation of intermediate I-4

I-3 (30 g, 95.1 mmol) was dissolved in 0.3 L of THF in a nitrogen atmosphere, followed by the addition of 0.3 L of methanol and cooling to 0 ° C. Sodium borohydride (36.0 g, 951 mmol) was added thereto, and tin (II) chloride (90.2 g, 475.5 mmol) was added thereto, followed by reaction at room temperature for 2 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (EA). The extract was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain I-4 (14.9 g, 55%).

HRMS (70 eV, EI +): m / z calcd for C21H19N: 285.1517, found: 285.

Elemental Analysis: C, 88%; H, 7%

Synthetic example  5: Preparation of intermediate I-5

After dissolving 1-bromo-4-nitrobenzene (50 g, 247.5 mmol) in 0.6 L of THF in a nitrogen atmosphere, diphenofuran-4-yl-boronic acid (63.0 g, 297.0 mmol) and tetrakis (Triphenylphosphine) palladium (8.58 g, 7.43 mmol) were added and stirred. Saturated potassium carbonate (72.9 g, 495.0 mmol) in water was added, and the mixture was heated at 80 占 폚 for 24 hours to reflux. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-5 (53.7 g, 75%).

HRMS (70 eV, EI +): m / z Calcd for C18 H11 NO3: 289.0739, found: 289.

Elemental Analysis: C, 75%; H, 4%

Synthetic example  6: Preparation of intermediate I-6

I-5 (30 g, 103.7 mmol) was dissolved in 0.3 L of THF in a nitrogen atmosphere, and then 0.3 L of methanol was added thereto, followed by cooling to 0 占 폚. Sodium borohydride (39.2 g, 1,037 mmol) was added thereto, and tin (II) chloride (98.3 g, 518.5 mmol) was added thereto and reacted at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with EA. The extract was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain I-6 (14.0 g, 52%).

HRMS (70 eV, EI +): m / z Calcd for C18 H13 NO: 259.0997, found: 259.

Elemental Analysis: C, 83%; H, 5%

Synthetic example  7: Preparation of Intermediate I-7

Carbazole (50 g, 299.0 mmol) was dissolved in 0.5 L of toluene in a nitrogen atmosphere and then 1-bromo-4-nitrobenzene (60.4 g, 299.0 mmol) and tris (diphenyldiacetone) dipalladium (8.26 g, 8.97 mmol), tris-tert butylphosphine (7.26 g, 35.9 mmol) and sodium tert-butoxide (34.5 g, , 358.8 mmol) were successively added thereto, followed by heating at 130 ° C for 46 hours to reflux. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound I-7 (74.1 g, 86%).

HRMS (70 eV, EI +): m / z Calcd for C18H12N2O2: 288.0899, found: 288.

Elemental Analysis: C, 75%; H, 4%

Synthetic example  8: Preparation of intermediate I-8

I-7 (30 g, 104.1 mmol) was dissolved in 0.3 L of THF in a nitrogen atmosphere, and then 0.3 L of methanol was added thereto, followed by cooling to 0 占 폚. Sodium borohydride (39.4 g, 1,041 mmol) was added thereto, and tin (II) chloride (98.7 g, 520.5 mmol) was added thereto and reacted at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with EA. The extract was dried over anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain I-6 (11.6 g, 43%).

HRMS (70 eV, EI +): m / z Calcd for C18 H14 N2: 258.1157, found: 258.

Elemental Analysis: C, 84%; H, 5%

Example  1: Preparation of compound 2

Dimethyl-9H-fluorene-2-amine (15.5 g, 74.1 mmol) was dissolved in 0.35 L of toluene under a nitrogen atmosphere. To this solution, 50.8 g (222.2 mmol) of Intermediate I- (2.0 g, 2.22 mmol), tris (tert-butylphosphine) (1.80 g, 4.23 mmol) and sodium tert-butoxide (15.7 g, 162.9 mmol) Lt; / RTI > for one day. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 1 (37.4 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C43H31NO2: 593.2355, found: 593.

Elemental Analysis: C, 87%; H, 5%

Example  2: Preparation of compound 3

(19.4 g, 92.9 mmol) was dissolved in 0.35 L of toluene, and thereto was added an intermediate I-2 (50 g, 204.3 mmol), tris (diphenyl (2.56 g, 2.79 mmol), tris (tert-butylphosphine) (2.26 g, 11.1 mmol) and sodium tert-butoxide (19.6 g, 204.4 mmol) Lt; / RTI > for one hour. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 3 (54.0 g, 93%).

HRMS (70 eV, EI +): m / z calcd for C43H31NS2: 625.1898, found: 625.

Elemental Analysis: C, 83%; H, 5%

Example  3: Preparation of compound 4

Intermediate 1-4 (10 g, 35.0 mmol) was dissolved in 0.15 L of toluene in a nitrogen atmosphere, and then intermediate I-2 (18.9 g, 77.1 mmol), tris (diphenylidenacetone) dipalladium g, 1.05 mmol), tris-tert-butylphosphine (0.85 g, 4.2 mmol) and sodium tert-butoxide (7.41 g, 77.1 mmol) were successively added and refluxed by heating at 100 ° C for 22 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 5 (20.9 g, 85%).

HRMS (70 eV, EI +): m / z calcd for C49H35NS2: 701.2211, found: 701.

Elemental Analysis: C, 84%; H, 5%

Example  4: Preparation of compound 110

(Biphenyl-4-yl) -9,9-dimethyl-9H-fluorene-2-amine (10 g, 27.7 mmol) was dissolved in 0.1 L of toluene in a nitrogen atmosphere, (0.76 g, 0.83 mmol), tris (tert-butylphosphine) (0.67 g, 3.32 mmol) and sodium tert-butoxide (5.85 g, 60.9 mmol) were successively added thereto, and the mixture was refluxed by heating at 100 ° C for 13 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 110 (13.9 g, 91%).

HRMS (70 eV, EI +): m / z calcd for C41 H31 NO: 553.2406, found: 553.

Elemental Analysis: C, 89%; H, 6%

Example  5: Preparation of compound 129

(10.1 g, 29.9 mmol) was dissolved in 0.1 L of toluene, and thereto was added an intermediate I-2 (16.1 g, 65.8 mmol), tris (0.82 g, 0.90 mmol), tris (tert-butylphosphine) (0.73 g, 3.59 mmol) and sodium tert-butoxide (6.32 g, 65.8 mmol) RTI ID = 0.0 > C < / RTI > for 17 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 129 (19.8 g, 88%).

HRMS (70 eV, EI +): m / z calcd for C52 H34 N2 S2: 750.2163, found: 750.

Elemental Analysis: C, 83%; H, 5%

Example  6: Preparation of compound 141

(27.9 g, 113.8 mmol) and tris (diphenylidenacetone) dipalladium (o) were dissolved in 0.15 L of toluene in a nitrogen atmosphere, and phenanthrene-2-amine (1.42 g, 1.55 mmol), tris-tert-butylphosphine (1.26 g, 6.2 mmol) and sodium tert-butoxide (10.9 g, 113.8 mmol) were successively added and refluxed by heating at 100 ° C for 23 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 141 (30.9 g, 98%).

HRMS (70 eV, EI +): m / z calcd for C42H27NS2: 609.1585, found: 609.

Elemental Analysis: C, 83%; H, 4%

Example  7: Preparation of Compound 150

(10 g, 41.1 mmol) was dissolved in 0.16 L of toluene in a nitrogen atmosphere followed by the addition of intermediate I-2 (22.1 g, 90.4 mmol), tris (diphenylidenacetone) dipalladium ) (1.13 g, 1.23 mmol), tris-tert-butylphosphine (1.0 g, 4.93 mmol) and sodium tert-butoxide (8.69 g, 90.4 mmol) were successively added thereto and the mixture was refluxed by heating at 100 ° C for 21 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 150 (25.2 g, 93%).

HRMS (70 eV, EI +): m / z Calcd for C46H29NS2: 659.1742, found: 659.

Elemental Analysis: C, 84%; H, 4%

Example  8: Preparation of compound 153

Biphenyl-4-amine (10 g, 59.1 mmol) was dissolved in 0.16 L of toluene in a nitrogen atmosphere, and then intermediate I-2 (31.8 g, 130.0 mmol) and tris (diphenylidenacetone) dipalladium (1.62 g, 1.77 mmol), tris-tert-butylphosphine (1.43 g, 7.09 mmol) and sodium tert-butoxide (12.5 g, 130.0 mmol) were successively added and refluxed by heating at 100 ° C for 14 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 153 (33.2 g, 96%).

HRMS (70 eV, EI +): m / z calcd for C40H27NS2: 585.1585, found: 585.

Elemental Analysis: C, 82%; H, 5%

Example  9: Preparation of compound 159

Intermediate I-2 (20.8 g, 84.8 mmol) and tris (diphenylidenacetone) dipalladium (o) (1.06 g) were dissolved in 0.15 L of toluene in a nitrogen atmosphere, g, 1.16 mmol), tris-tert-butylphosphine (0.94 g, 4.63 mmol) and sodium tert-butoxide (8.15 g, 84.8 mmol) were successively added thereto and the mixture was refluxed by heating at 100 ° C for 16 hours. After the completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with DCM, and then dried over anhydrous MgSO _{4. The} extract was filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 159 (22.2 g, 96%).

HRMS (70 eV, EI +): m / z calcd for C46H29NOS2: 675.1691, found: 675.

Elemental Analysis: C, 82%; H, 4%

Example  10: Preparation of compound 171

Intermediate I-2 (20.8 g, 85.2 mmol) and tris (diphenylideneacetone) dipalladium (o) (1.06 g, 1.16 mmol) were dissolved in 0.16 L of toluene in a nitrogen atmosphere. ), tris-tert butylphosphine (0.94 g, 4.64 mmol) and sodium tert-butoxide (8.19 g, 85.2 mmol) were successively added thereto, followed by heating at 100 ° C for 18 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 171 (23.5 g, 90%).

HRMS (70 eV, EI +): m / z calcd for C46H30N2S2: 674.1850, found: 674.

Elemental Analysis: C, 82%; H, 4%

(Production of organic light emitting device)

Example  11: Fabrication of organic light emitting device blue Common layer )

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. After the substrate was transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator. The prepared ITO transparent electrode was used as an anode to form a 4'-bis [N- [4- {N, N-bis (3-methylphenyl) amino} -phenyl] , 4'-bis [N- [4- {N, N-bis (3-methylphenyl) amino} -phenyl] -N-phenylamino] biphenyl: DNTPD) was vacuum deposited to form a 600 Å- . Subsequently, a 300 Å thick hole transport layer was formed by vacuum deposition using the compound 2 prepared in Example 1. (9,10-di- (2-naphthyl) anthracene (AND)) was used as a host on the hole transport layer and 2,5,8,11-tetra (Tert-butyl perylene: TBPe) was doped at 3 wt%, and a 250 Å thick light emitting layer was formed by vacuum deposition. Thereafter, Alq3 was vacuum deposited on the light emitting layer to form an electron transporting layer having a thickness of 250 ANGSTROM. LiF 10 Å and Al 1000 Å were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

 The organic light emitting device has five layers of organic thin film layers. Specifically, the organic light emitting device has a structure of Al (1000 Å) / LiF (10 Å) / Alq3 (250 Å) / EML [AND: TBPe = 97: 3] ) / HTL (300 Å) / DNTPD (600 Å) / ITO (1500 Å).

Example  12

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 2 was used instead of Example 1.

Example  13

An organic light emitting device was prepared in the same manner as in Example 11 except that Example 3 was used instead of Example 1.

Example  14

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 4 was used instead of Example 1.

Example  15

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 5 was used instead of Example 1.

Example  16

An organic luminescent device was prepared in the same manner as in Example 11, except that Example 6 was used instead of Example 1.

Example  17

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 7 was used instead of Example 1.

Example  18

An organic light emitting device was prepared in the same manner as in Example 11 except that Example 8 was used instead of Example 1.

Example  19

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 9 was used instead of Example 1.

Example  20

An organic light emitting device was prepared in the same manner as in Example 11, except that Example 10 was used instead of Example 1.

Comparative Example  One

In Example 11, an organic light emitting device was manufactured in the same manner except that NPB was used instead of Example 1. The structure of the NPB is described below.

Comparative Example  2

In Example 11, an organic light emitting device was manufactured in the same manner except that HT1 was used instead of Example 1. [ The structure of HT1 is described below.

Comparative Example  3

In Example 11, an organic light emitting device was manufactured in the same manner except that HT2 was used instead of Example 1. The structure of HT2 is described below

The structures of DNTPD, AND, TBPe, NPB, HT1 and HT2 used in the production of the organic light emitting device are as follows.

(Performance Measurement of Organic Light Emitting Device)

For each of the organic light emitting devices manufactured in Examples 11 to 20 and Comparative Examples 1 to 3, the current density change, the luminance change and the luminous efficiency were measured according to the voltage. Specific measurement methods are as follows, and the results are shown in Table 1 below

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

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltage meter (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).

device Compound used in hole transport layer Voltage (V) Color (EL color) Efficiency (cd / A) Half life (h)
At 1000 cd / m ² Example 11 2 5.0 Blue 6.4 1,340 Example 12 3 5.2 Blue 6.7 900 Example 13 4 6.2 Blue 6.0 1,600 Example 14 110 6.5 Blue 6.1 1,500 Example 15 129 5.5 Blue 6.5 1,200 Example 16 150 6.7 Blue 6.0 1,450 Example 17 141 6.5 Blue 6.2 1,400 Example 18 153 6.5 Blue 5.5 1,800 Example 19 159 4.8 Blue 6.6 1,500 Example 20 171 6.5 Blue 5.7 1,500 Comparative Example 1 NPB 7.1 Blue 4.9 1,250 Comparative Example 2 HT1 6.6 Blue 5.7 1,340 Comparative Example 3 HT2 6.5 Blue 6.0 1,300

According to the results shown in Table 1, the efficiencies of Examples 11 to 14 in which fluorine substituent groups were included were significantly increased as compared with Comparative Examples 1 and 2. In the case of Comparative Example 3, since the fluorine substituent group is the most efficient among the comparative examples, it can be seen that the efficiency of the fluorene substituent is greatly increased. It can be seen that the driving voltages of Examples 11 to 20 are lower than those of Comparative Examples 1 to 3 as a whole. It can be deduced from this that the indeno substituent lowers the driving voltage. In the case of Example 18 in which the simplest structure is used, the half life is the highest, and it can be seen that the simple structure contributes to the device lifetime to some extent. Based on this, a low voltage, high efficiency, high brightness, long life organic light emitting device having excellent hole injection and hole transporting ability could be manufactured.

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 110: cathode
120: anode 105: organic thin film layer
130: luminescent layer 140: hole transport layer
150: electron transport layer 160: electron injection layer
170: Hole injection layer 230: Emission layer + Electron transport layer

Claims (19)

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

In Formula 1,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
L ¹ to L ³ independently represent a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted A C2 to C30 heteroarylene group or a combination thereof,
n1 to n3 independently represent any one of 0 to 3,
A is < RTI ID = 0.0 > A-2 &
B is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
[A-2]

In the above formula (A-2)
X ¹ is -O- or -S-,
R ³ and R ⁴ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a perorcenyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy A substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfamoyl An amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group, A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
And B is a structural formula A-2. The method according to claim 1,
Wherein Ar < ¹ > is the following formula B-1:
[Formula B-1]

In the above formula (B-1)
R ⁵ to R ⁸ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy A substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfamoyl groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group , A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
Wherein Ar < ¹ > is the following formula B-2:
[Formula B-2]

In the above formula (B-2)
R ⁵ to R ⁸ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy A substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfamoyl groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group , A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
Wherein Ar < ¹ > is the following formula B-3:
[Formula B-3]

In the above formula (B-3)
R ⁹ to R ¹² independently represent hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy A substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfa A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group , A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
And Ar < ¹ > is the following formula (B-4).
[Formula B-4]

The method according to claim 1,
Wherein Ar < ¹ > is the following formula (B-5):
[Formula B-5]

In the above formula (B-5)
X ² is -O-, -S- or NR '
R ¹³ , R ¹⁴ and R 'are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acylox A substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 alcohol A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group , A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
Wherein Ar < ¹ > is the following formula (B-6): < EMI ID =
[Formula B-6]

In the above formula (B-6)
R ¹⁵ and R ¹⁶ independently represent hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a perorcenyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy A substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfamoyl groups, An amino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group, A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or combinations thereof. The method according to claim 1,
And Ar < ¹ > is a substituted or unsubstituted biphenyl group. The method according to claim 1,
Wherein A and B are substituents represented by the above formula (A-2). The method according to claim 1,
In the above formula (A-2), R ³ and R ⁴ are hydrogen. The method according to claim 1,
Wherein the compound for organic optoelectronic devices has a molecular weight of 700 or less. The method according to claim 1,
Wherein the compound for organic optoelectronic devices has a molecular weight of 600 or less. The method according to claim 1,
Wherein the organic optoelectronic device is any one selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor drum, and an organic memory 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 for an organic optoelectronic device according to any one of claims 1 to 5. [ 16. The method of claim 15,
Wherein the organic layer is any one selected from the group consisting of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and combinations thereof. 17. The method of claim 16,
Wherein the compound for an organic optoelectronic device is contained in a light emitting layer. 18. The method of claim 17,
Wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in a light emitting layer. A display device comprising the organic light-emitting device of claim 15.

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