KR20140087806A - 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 device including the same and a display device including the organic light emitting device. The present invention provides the 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 Formula 1, Ar ¹ and Ar ² are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and in the range of Ar ¹ and Ar ² , X ¹ to X ¹⁶ are independently of each other -N- or -CR'-, at least one of X ¹ to X ¹⁶ is -N-, and L ¹ to L ³ are the same or different from each other Independently, 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, N1 to n3 are each independently any one of 0 to 3 and R 'is hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1- C20 amine group, a nitro group, a carboxyl group, a perocenyl 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 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, C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

At least one of X ¹ to X ⁸ is -N-, and at least one of X ⁹ to X ¹⁶ may be -N-.

Ar ¹ and Ar ² may be any one of the following substituents independently of each other.

In this substituent, X is -O- or -S- and Ar ⁵ to Ar ⁷ 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 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 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, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino , 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, 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 a combination thereof.

Ar ¹ and Ar ² may be, independently of each other, a substituted or unsubstituted C6 to C30 aryl group.

The L ¹ to L ³ may independently be any one of the following substituents.

In this substituent, X is -O- or -S-.

The compound for an organic optoelectronic device may be any one of the following compounds.

In the above compound, Ar ¹ and Ar ² are, independently of each other, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and include nitrogen in the range of Ar ¹ and Ar ² Lt; / RTI > is excluded.

The organic optoelectronic device may be any one selected from the group consisting of organic optoelectronic devices, organic light emitting devices, organic solar cells, organic transistors, organic photoconductor drums, and organic memory devices.

In another embodiment of the present invention, at least one organic thin film layer interposed between the anode and the cathode and between the anode and the cathode is provided in at least one of the organic thin film layers, The organic electroluminescent device includes the compound for an organic optoelectronic device according to an embodiment.

The organic thin film layer may be 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.

The compound for an organic optoelectronic device may be included in a hole injection layer or a hole transport layer.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a cathode, a cathode, and at least one organic thin film layer formed between the anode and the cathode, wherein the organic thin film layer includes a light emitting layer, a hole transporting layer, Or a combination thereof, wherein the organic thin film layer includes a light emitting layer and a plurality of hole transporting layers, and a hole transporting layer adjacent to the light emitting layer among the plurality of the hole transporting layers includes the organic electroluminescent device according to one embodiment of the present invention And one of the hole transporting layers not adjacent to the light emitting layer comprises a compound represented by the following formula (B-1).

[Formula B-1]

In the formula (B-1), R ¹ to R ⁴ independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 R ¹ and R ² may form a fused ring, R ³ and R ⁴ may form a fused ring together, Ar ¹ to Ar ³ may be substituted or unsubstituted independently of one another, L ¹ to L ⁴ independently represent a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 heteroaryl 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 to n4 independently represent an integer of 0 to 3;

The compound represented by the above formula (B-1) may be represented by any of the following formulas J-1 to J-144.

[J-1] [J-2] [J-3]

[J-4] [J-5] [J-6]

[J-7] [J-8] [J-9]

[J-10] [J-11] [J-12]

[J-13] [J-14] [J-15]

[J-16] [J-17] [J-18]

[J-19] [J-20] [J-21]

[J-22] [J-23] [J-24]

[J-25] [J-26] [J-27]

[J-28] [J-29] [J-30]

[J-31] [J-32] [J-33]

[J-34] [J-35] [J-36]

[J-37] [J-38] [J-39]

[J-40] [J-41] [J-42]

[J-43] [J-44] [J-45]

[J-46] [J-47] [J-48]

[J-49] [J-50] [J-51]

[J-52] [J-53] [J-54]

[J-55] [J-56] [J-57]

[J-58] [J-59] [J-60]

[J-61] [J-62] [J-63]

[J-64] [J-65] [J-66]

[J-67] [J-68] [J-69]

[J-70] [J-71] [J-72]

[J-73] [J-74] [J-75]

[J-76] [J-77] [J-78]

[J-79] [J-80] [J-81]

[J-82] [J-83] [J-84]

[J-85] [J-86] [J-87]

[J-88] [J-89] [J-90]

[J-91] [J-92] [J-93]

[J-94] [J-95] [J-96]

[J-97] [J-98] [J-99]

[J-100] [J-101] [J-102]

[J-103] [J-104] [J-105]

[J-106] [J-107] [J-108]

[J-109] [J-110] [J-111]

[J-112] [J-113] [J-114]

[J-115] [J-116] [J-117]

[J-118] [J-119] [J-120]

[J-121] [J-122] [J-123]

[J-124] [J-125] [J-126]

[J-127] [J-128] [J-129]

[J-130] [J-131] [J-132]

[J-133] [J-134] [J-135]

[J-136] [J-137] [J-138]

[J-139] [J-140] [J-141]

[J-142] [J-143] [J-144]

The HOMO level of the compound represented by Formula 1 may be 5.4 eV or more and 6.0 eV or less.

The triplet excitation energy (T1) of the compound represented by Formula 1 may be 2.5 eV or more and 2.9 eV or less.

The HOMO level of the compound represented by the above formula (B-1) may be 5.2 eV or more and 5.6 eV or less.

According to another embodiment of the present invention, there is provided a display device including the organic light emitting device according to an embodiment of the present invention.

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.

1 to 5 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.

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

The alkyl group may be an alkyl group 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" means a substituent in which all the elements of the cyclic substituent have p-orbital and the p-orbital forms a conjugation, and monocyclic or fused-ring polycyclic That is, 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.

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.

In one embodiment of the present invention, a compound for an organic optoelectronic device represented by the following Formula 1 can be provided.

[Chemical Formula 1]

In Formula 1, Ar ¹ and Ar ² are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and in the range of Ar ¹ and Ar ² , X ¹ to X ¹⁶ are independently of each other -N- or -CR'-, at least one of X ¹ to X ¹⁶ is -N-, and L ¹ to L ³ are the same or different from each other Independently, 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, N1 to n3 are each independently any one of 0 to 3 and R 'is hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1- C20 amine group, a nitro group, a carboxyl group, a perocenyl 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 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, C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

The compound represented by Formula 1 may have a core structure containing at least one azacarbazolyl group. In the case of such a core structure, it is possible to improve the luminous efficiency and the roll-off characteristics by limiting the hole transporting ability of the molecules.

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.

More specifically, for example, L ¹ to L ³ independently of each other may be any one of the following substituents. However, the present invention is not limited thereto.

In this substituent, X is -O- or -S-.

More specifically, for example, Ar ¹ and Ar ² may independently be any one of the following substituents. However, the present invention is not limited thereto.

In this substituent, X is -O- or -S- and Ar ⁵ to Ar ⁷ 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 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 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, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino , 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, 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 a combination thereof.

More specifically, the desired compound can selectively control Ar ¹ and Ar ² according to the properties of HOMO and / or LUMO.

More specifically, Ar ¹ and Ar ² may be, independently of each other, a substituted or unsubstituted C6 to C30 aryl group. In this case, the thermal stability of the compound can be increased by increasing the glass transition temperature of the molecular structure.

At least one of X ¹ to X ⁸ is -N-, and at least one of X ⁹ to X ¹⁶ may be -N-. That is, the compound for organic optoelectronic devices according to an embodiment of the present invention may have a core containing two azacarbazolyl groups. In this case, it is possible to improve the luminous efficiency and improve the roll-off characteristics by limiting the hole transporting ability of the molecules.

More specifically, for example, the compound for an organic optoelectronic device may be any one of the following compounds, but is not limited thereto.

In the above compound, Ar ¹ and Ar ² are, independently of each other, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and include nitrogen in the range of Ar ¹ and Ar ² Lt; / RTI > is excluded.

For example, the compound represented by Formula 1 may be any one of the following compounds. However, this is only an example.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a cathode, a cathode, and at least one organic thin film layer sandwiched between the anode and the cathode, wherein at least one of the organic thin film layers includes the above- Thereby providing an organic optoelectronic 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 specifically a hole injection layer or a hole transport 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 to 5 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 to 5, organic light emitting devices 100, 200, 300, 400, and 500 according to an embodiment of the present invention include a cathode 120, a cathode 110, And a structure including at least one organic thin film layer (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. More specifically, 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. More specifically, a metal electrode such as aluminum can be used for the cathode.

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 130 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.

3 is a three-layer organic light emitting device 300 in which an electron transport layer 150, a light emitting layer 130 and a hole transport layer 140 are present as an organic thin film layer 105. The organic thin film layer 105, The emissive layer 130 is in the form of an independent layer and has a form in which a film having excellent electron transportability and hole transportability (the electron transport layer 150 and the hole transport layer 140) is stacked as a separate layer.

4, a four-layer organic light emitting device 400 having an electron injection layer 160, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 as organic thin film layers 105, And the hole injection layer 170 can improve the bonding property with ITO used as the anode.

5, the organic thin film layer 105 has different functions such as an electron injection layer 160, an electron transport layer 150, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 Layer organic light emitting device 500. The organic light emitting device 500 is effective for lowering the voltage by forming the electron injection layer 160 separately.

1 to 5, the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, the hole injection layer 170, and the organic thin film layer 105, And combinations thereof, includes a material for the organic optoelectronic device.

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 optoelectronic device.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a cathode, a cathode, and at least one organic thin film layer formed between the anode and the cathode, wherein the organic thin film layer includes a light emitting layer, a hole transporting layer, Or a combination thereof, wherein the organic thin film layer includes a light emitting layer and a plurality of hole transporting layers, and a hole transporting layer adjacent to the light emitting layer among the plurality of the hole transporting layers includes the organic electroluminescent device according to one embodiment of the present invention And one of the hole transporting layers not adjacent to the light emitting layer comprises a compound represented by the following formula (B-1).

[Formula B-1]

In the formula (B-1), R ¹ to R ⁴ independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 R ¹ and R ² may form a fused ring, R ³ and R ⁴ may form a fused ring together, Ar ¹ to Ar ³ may be substituted or unsubstituted independently of one another, L ¹ to L ⁴ independently represent a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 heteroaryl 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 to n4 independently represent an integer of 0 to 3;

As described above, the organic optoelectronic device according to an embodiment of the present invention may include a plurality of hole transporting layers. In this case, electron hopping becomes smoother than the single hole transport layer, and the hole transport efficiency is increased. In addition, as described above, the organic optoelectronic device according to one embodiment of the present invention has superior electrochemical and thermal stability, thereby improving lifetime characteristics and high luminous efficiency even at a low driving voltage.

More specifically, the hole transporting layer adjacent to the light emitting layer among the plurality of hole transporting layers may include the compound according to one embodiment of the present invention described above. The description will be omitted because it is redundant.

More specifically, any one of the hole transporting layers not adjacent to the light emitting layer may include the compound represented by the above formula (B-1).

The compound represented by B-1 is an amine compound, and at least one substituent in the amine may be substituted with a carbazole group.

In the above B-1, R ¹ and R ² may form a fused ring together with R ³ and R ⁴ may form a fused ring together with each other. In this case, there is an advantage that the thermal stability is increased and the electron transfer and injection characteristics are increased.

More specifically, when a plurality of hole transporting layers are formed by combining a compound for an organic optoelectronic device and a compound represented by B-1 according to an embodiment of the present invention, such as an organic optoelectronic device according to an embodiment of the present invention, The electron hopping is optimized for the energy level of the electron transporting layer and the electron transporting layer to have excellent electrochemical and thermal stability. Thus, the organic optoelectronic device can be improved in lifetime characteristics and can have a high luminous efficiency even at a low driving voltage.

For example, the compound represented by the formula (B-1) may be represented by any of the following formulas (J-1) to (J-144). However, the present invention is not limited thereto.

[J-1] [J-2] [J-3]

[J-4] [J-5] [J-6]

[J-7] [J-8] [J-9]

[J-10] [J-11] [J-12]

[J-13] [J-14] [J-15]

[J-16] [J-17] [J-18]

[J-19] [J-20] [J-21]

[J-22] [J-23] [J-24]

[J-25] [J-26] [J-27]

[J-28] [J-29] [J-30]

[J-31] [J-32] [J-33]

[J-34] [J-35] [J-36]

[J-37] [J-38] [J-39]

[J-40] [J-41] [J-42]

[J-43] [J-44] [J-45]

[J-46] [J-47] [J-48]

[J-49] [J-50] [J-51]

[J-52] [J-53] [J-54]

[J-55] [J-56] [J-57]

[J-58] [J-59] [J-60]

[J-61] [J-62] [J-63]

[J-64] [J-65] [J-66]

[J-67] [J-68] [J-69]

[J-70] [J-71] [J-72]

[J-73] [J-74] [J-75]

[J-76] [J-77] [J-78]

[J-79] [J-80] [J-81]

[J-82] [J-83] [J-84]

[J-85] [J-86] [J-87]

[J-88] [J-89] [J-90]

[J-91] [J-92] [J-93]

[J-94] [J-95] [J-96]

[J-97] [J-98] [J-99]

[J-100] [J-101] [J-102]

[J-103] [J-104] [J-105]

[J-106] [J-107] [J-108]

[J-109] [J-110] [J-111]

[J-112] [J-113] [J-114]

[J-115] [J-116] [J-117]

[J-118] [J-119] [J-120]

[J-121] [J-122] [J-123]

[J-124] [J-125] [J-126]

[J-127] [J-128] [J-129]

[J-130] [J-131] [J-132]

[J-133] [J-134] [J-135]

[J-136] [J-137] [J-138]

[J-139] [J-140] [J-141]

[J-142] [J-143] [J-144]

The HOMO level of the compound represented by Formula 1 may be 5.4 eV or more and 6.0 eV or less. In this case, holes can be injected uniformly from the compound of formula (B-1) and the injection barrier can be lowered by the light emitting layer.

The triplet excitation energy (T1) of the compound represented by Formula 1 may be 2.5 eV or more and 2.9 eV or less. In this case, it is possible to prevent the luminous efficiency of the green phosphorescent device from decreasing.

The HOMO level of the compound represented by the above formula (B-1) may be 5.2 eV or more and 5.6 eV or less. In this case, the driving voltage can be lowered by lowering the hole injection barrier from the anode.

According to another embodiment of the present invention, there is provided a display device including the organic light emitting device according to an embodiment of the present invention.

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)

Intermediate Azacavazole  Structure synthesis method

The azacarbazole structure as an intermediate can be synthesized through the reaction described in the following examples.

Azacavazole  On structure Aryl group  or Heteroaryl group  Introduction Azacavazole  On halides Aryl group  or Heteroaryl group  Introduction)

The following reaction scheme shows a scheme for introducing an aryl group (or a heteroaryl group) into an azacarbazole structure.

A method of introducing an aryl group (or a heteroaryl group) into a heterocyclic substituent structure (for example, an azacarbazole structure) containing nitrogen is a well known Buchwald-Hartwig reaction.

(References Name Reactions 2006, 98-99, DOI: 10.1007 / 3-540-30031-7_48)

N-aryl (or Heteroaryl Introduction Azacavazole Boronic acid  Compound synthesis

An azacarbazole halide was synthesized by the following reaction. Which can be used as an intermediate for a compound for an organic optoelectronic device according to an embodiment of the present invention.

Methods for converting azacarbazole halide compounds to boronic acid compounds were largely synthesized by two methods. As shown in the above reaction formula, Method A using the well-known BuLi and triisopropylborate and Method B using the ligand X-Phos and tetrahydroxydiboron developed by the Buchwald group of MIT Chemistry were used to prepare the same carbazole boronic acid Compounds corresponding to the compounds A-2 to E-2 were synthesized.

Halogen compounds and Boronic acid  Compound Suzuki  Final compound synthesis via coupling reaction

Unlike bromide or iodide in halogen compounds, the synthesis is not good in the case of chlorides due to the general Suzuki coupling reaction. According to the paper reported in 2006, it has been reported that the yield of coupling reaction varies depending on the type of active ligand. (KL Billingsley, KW Anderson, SL Buchwald, Angew . Chem . Int . Ed . , 2006, 45 , 3484-3488)

The present inventors synthesized various embodiments according to one embodiment of the present invention with reference to the above-mentioned references.

Example  1: Final compound a1 Synthesis of

10.0 g (25.3 mmol) of the intermediate halogen compound and 8.7 g (30.4 mmol) of the intermediate boronic acid compound were dissolved in 10.5 g (76.0 mmol) of potassium carbonate in a three-neck 250 mL round bottom flask, mL and water (100 mL). Then, 519 mg of 4 mol% of ligand A and 110 mg of 2 mol% of Pd (OAc) ₂ were added and reacted at 100 ° C for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 100 ml of distilled water was added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated, and subjected to silica gel column chromatography. The eluate thus obtained was concentrated and dried to obtain the target compound in a solid state, and LCMS was used to confirm that the compound was the target compound.

Example  2 to 20: final compound a2  To a20 Synthesis of

Only the structure of the halogen compound of the intermediate and the boronic acid compound was different, and all the reaction and purification procedures proceeded in the same manner to obtain the final compounds a2 to a20. This is shown in Table 1 below.

No Halogen compound Boronic acid  compound Final composite structure Yield and
LC Mass Data (M + H ⁺ ) Example 1

　

　

　

a1 90%
602.34 Example 2

　

　

a2 93%
602.35 Example 3

　

　

a3 92%
603.28 Example 4

　

　

a4 88%
603.22 Example 5

　

　

a5 93%
603.18 Example 6

　

　

a6 78%
603.24 Example 7

　

　

a7 83%
603.23 Example 8

　

　

a8 89%
604.22 Example 9

　

　

a9 91%
487.19 Example 10

　

　

a10 93%
679.29 Example 11

　

　

a11 91%
679.31 Example 12

　

　

a12 80%
679.28 Example 13

　

　

a13 88%
719.30 Example 14

　

　

a14 70%
488.20 Example 15

　

　

a15 72%
604.25 Example 16

　

　

a16 85%
576.22 Example 17

　

　

a17 87%
577.23 Example 18

　

　

a18 90%
719.34 Example 19

　

　

a19 78%
720.35 Example 20

　

　

a20 81%
721.33

Manufacture of organic light emitting device

Example  21 (Production of green organic light emitting device)

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine. HT-1 was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a 700 Å thick hole injection layer and a transport layer. Subsequently, an auxiliary hole transporting layer having a thickness of 100 Å was formed by vacuum deposition using the compound prepared in Example 1. (2-phenylpyridine) iridium (III) [Ir (ppy) ₃ ] was used as a host on the auxiliary hole transporting layer using (4,4'-N, N'- Was doped to 5 wt%, and a 300Å thick light emitting layer was formed by vacuum deposition.

Then, biphenoxy-bis (8-hydroxyquinoline) aluminum [Balq] was vacuum-deposited on the light emitting layer to form a hole blocking layer having a thickness of 50 Å. A tris (8-hydroxyquinoline) aluminum [Alq ₃ ] was vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 250 A, and LiF 10 A and Al 1000 A were sequentially vacuum deposited on the electron transporting layer to form a cathode Thereby preparing an organic light emitting device.

The organic light emitting device has a structure having five organic thin film layers. Specifically,

Al (1000 Å) / LiF (10 Å) / Alq ₃ 250 Å / Balq 50 Å / EML CBP Ir (ppy) ₃ = 95: 5 300 ANT / HT- ) / ITO (1500 ANGSTROM).

Example  22

An organic light emitting device was prepared in the same manner as in Example 21 except that the compound of Example 2 was used instead of the compound of Example 1.

Example  23

An organic light emitting device was prepared in the same manner as in Example 21 except that the compound of Example 4 was used instead of the compound of Example 1.

Example  24

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound of Example 5 was used instead of the compound of Example 1.

Example  25

An organic light emitting device was prepared in the same manner as in Example 21 except that the compound of Example 6 was used instead of the compound of Example 1.

Example  26

An organic light emitting device was prepared in the same manner as in Example 21, except that the compound of Example 10 was used instead of the compound of Example 1.

Example  27

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound of Example 11 was used instead of the compound of Example 1.

Example  28

An organic light emitting device was prepared in the same manner as in Example 21 except that the compound of Example 12 was used instead of the compound of Example 1.

Example  29

An organic luminescent device was prepared in the same manner as in Example 21, except that the compound of Example 17 was used instead of the compound of Example 1.

Example  30

An organic light emitting device was prepared in the same manner as in Example 21, except that the compound of Example 18 was used instead of the compound of Example 1.

Example  31

An organic luminescent device was prepared in the same manner as in Example 21, except that the compound of Example 19 was used instead of the compound of Example 1.

Example  32

An organic luminescent device was prepared in the same manner as in Example 21, except that the compound of Example 20 was used instead of the compound of Example 1.

Comparative Example  One

N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used in place of HT- 1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used as the organic electroluminescent device.

Comparative Example  2

Except that N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used in place of HT- 4 '' - (9-carbazolyl)) - triphenylamine [TCTA].

Comparative Example  3

An organic light emitting device was prepared in the same manner as in Example 21, except that HT-1 was used instead of the compound of Example 1.

The characteristics of the organic light emitting device manufactured under the following conditions were evaluated. The results are shown in Table 2 below.

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

For the organic light emitting device manufactured, the current value 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, the 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) and the power efficiency (lm / W) of the same brightness (1,000 cd / m 2) were calculated using the luminance, current density and voltage measured from the above (1) and (2).

(4) The color coordinates were measured using a luminance meter (Minolta Cs-100A).

device HTL Secondary HTL The driving voltage (V) Current density
(mA / cm ² ) The luminous efficiency (cd / A) Half life @ 3000 nit Example 21 HT-1 a1 7.7 9.1 44.2 253 Example 22 HT-1 a2 7.8 9.3 43.5 230 Example 23 HT-1 a4 8.0 9.5 47.1 210 Example 24 HT-1 a5 7.9 10.4 43.9 203 Example 25 HT-1 a6 8.2 10.1 42.4 191 Example 26 HT-1 a10 7.7 9.8 44.6 188 Example 27 HT-1 a11 7.8 9.6 47.2 171 Example 28 HT-1 a12 7.9 9.8 46.3 220 Example 29 HT-1 a17 7.6 10.4 41.6 164 Example 30 HT-1 a18 7.8 9.7 43.5 156 Example 31 HT-1 a19 8.0 8.7 46.8 177 Example 32 HT-1 a20 8.0 8.9 46.1 182 Comparative Example 1 NPB NPB 8.4 12.3 24.8 121 Comparative Example 2 NPB TCTA 7.3 12.5 42.0 153 Comparative Example 3 HT-1 HT-1 7.6 12.9 36.2 193

* Measured at driving voltage and luminous efficiency of 3,000 nit

According to the results of Table 2, in the green phosphorescent organic electroluminescent devices, in Examples 21 to 32 using the compound according to one embodiment of the present invention as the auxiliary hole transport layer as compared with Comparative Example 1 or Comparative Example 3 in which the auxiliary hole transport layer was not used Thereby improving the luminous efficiency and lifetime of the organic light emitting device. In particular, the embodiment of the present invention compared to Comparative Example 3 shows that the luminous efficiency increases by at least 10% or more, and compared with Comparative Example 2 in which TCTA is used as an auxiliary hole transport layer, Is at least 10% higher than that of the conventional device, the lifetime of the device is one of the biggest problems in commercialization in terms of commercialization of the device. Therefore, it is considered that the results of the above embodiments are enough to commercialize the device.

Example  33 (Preparation of red organic light emitting device)

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine. The thus prepared ITO transparent electrode was used as an anode, and 4,4'-bis [N- [4- {N, N-bis (3-methylphenyl) amino} -phenyl] -N-phenylamino] biphenyl Was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. HT-1 was vacuum deposited to form a hole transport layer having a thickness of 200 Å. An auxiliary hole transporting layer having a thickness of 100 Å was formed on the hole transporting layer by vacuum deposition using the compound prepared in Example 1. (2-phenylquinoline) (acetylacetonate) iridium (III) [Ir] was used as a host on the auxiliary hole transporting layer using (4,4'-N, N'-dicarbazole) (pq) ₂ acac] was doped to 7 wt%, and a 300 Å thick light emitting layer was formed by vacuum deposition.

Then, biphenoxy-bis (8-hydroxyquinoline) aluminum [Balq] was vacuum-deposited on the light emitting layer to form a hole blocking layer having a thickness of 50 Å. A tris (8-hydroxyquinoline) aluminum [Alq ₃ ] was vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 250 A, and LiF 10 A and Al 1000 A were sequentially vacuum deposited on the electron transporting layer to form a cathode Thereby preparing an organic light emitting device.

The organic light emitting device has a structure having six organic thin film layers. Specifically,

(1000 Å) / LiF (10 Å) / Alq 3 (250 Å) / Balq (50 Å) / EML [CBP: Ir (pq) ₂ acac = 93: 7] ) / DNTPD (600 Å) / ITO (1500 Å).

Example  34

In Example 33, an organic light emitting device was manufactured in the same manner as in Example 33, except that the compound of Example 2 was used instead of the compound of Example 1.

Example  35

An organic light emitting device was prepared in the same manner as in Example 33 except that the compound of Example 4 was used instead of the compound of Example 1.

Example  36

An organic light emitting device was prepared in the same manner as in Example 33 except that the compound of Example 5 was used instead of the compound of Example 1.

Example  37

An organic light emitting device was prepared in the same manner as in Example 33 except that the compound of Example 6 was used instead of the compound of Example 1.

Example  38

In Example 33, an organic luminescent device was manufactured in the same manner except that the compound of Example 10 was used instead of the compound of Example 1.

Example  39

An organic light emitting device was prepared in the same manner as in Example 33 except that the compound of Example 12 was used instead of the compound of Example 1.

Example  40

An organic light emitting device was prepared in the same manner as in Example 33 except that the compound of Example 20 was used instead of the compound of Example 1.

Comparative Example  4

In Example 33, N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used instead of HT- 1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used as the organic electroluminescent device.

Comparative Example  5

N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine [NPB] was used in place of HT-1 in Example 33, 4 '' - (9-carbazolyl)) - triphenylamine [TCTA].

Comparative Example  6

An organic light emitting device was prepared in the same manner as in Example 33, except that HT-1 was used instead of the compound of Example 1.

The structures of DNTPD, NPB, HT-1, TCTA, CBP, Balq, Alq ₃ , Ir (ppy) ₃ and Ir (pq) ₂ acac used in the production of the organic light emitting device are as follows.

The characteristics of the organic light emitting device were evaluated in the same manner as described above, and the results are shown in Table 3 below.

device HTL Secondary HTL The driving voltage (V) Current density
(mA / cm ² ) The luminous efficiency (cd / A) T80 Life (h) @ 1000nit Example 33 HT-1 a1 8.5 9.6 18.7 > 1,000 Example 34 HT-1 a2 8.4 9.5 18.6 > 950 Example 35 HT-1 a4 8.3 9.3 19.5 845 Example 36 HT-1 a5 8.2 10.1 21.3 824 Example 37 HT-1 a6 8.4 10.5 19.0 820 Example 38 HT-1 a10 8.8 10.8 20.5 900 Example 39 HT-1 a12 9.3 10.5 18.2 840 Example 40 HT-1 a20 9.1 11.7 22.5 806 Comparative Example 4 NPB NPB 8.7 12.5 14.9 711 Comparative Example 5 NPB TCTA 9.1 12.9 16.8 667 Comparative Example 6 HT-1 HT-1 8.5 13.3 16.4 830

* Measured at driving voltage and luminous efficiency of 1,000 nit

According to the results of Table 3, in the red phosphorescent organic electroluminescent device, in Examples 33 to 40 in which the compound according to one embodiment of the present invention was used as the auxiliary hole transport layer in Comparative Example 4 or Comparative Example 6 in which the auxiliary hole transport layer was not used Thereby improving the luminous efficiency and lifetime of the organic light emitting device. In particular, it can be seen that the luminous efficiency of the embodiment of the present invention is significantly increased by at least 15% compared to that of Comparative Example 3. In contrast to Comparative Example 5 in which TCTA is used as an auxiliary hole transport layer, At least 10%, and the lifetime of the light emitting device is increased by at least about 20%. In particular, it can be seen that the efficiency and lifetime of the red phosphorescent device are improved by structurally controlling the hole transporting characteristics. Considering that lifetime of a device is one of the biggest problems of commercialization in terms of commercialization of an actual device, the results of the above embodiments are considered sufficient to commercialize the device.

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 (16)

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

In Formula 1,
Ar ¹ and Ar ² are, independently of each other, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and the heteroaryl group containing nitrogen in the range of Ar ¹ and Ar ² is Excluded,
X ¹ to X ¹⁶ are independently of each other -N- or -CR'-, at least one of X ¹ to X ¹⁶ is -N-,
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,
Wherein R 'is 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 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 group, A substituted or unsubstituted C2 to C20 acyloxy group, 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 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, substituted or unsubstituted C1 to C20 sulfamoylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino 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 alkylsulfonyl group, Substituted C1 to C20 ureide groups, substituted or unsubstituted C3 to C40 silyl groups, or combinations thereof.
The method according to claim 1,
At least one of X ¹ to X ⁸ is -N-, and at least one of X ⁹ to X ¹⁶ is -N-.
The method according to claim 1,
Wherein Ar ¹ and Ar ² are each independently any one of the following substituents:

In this substituent,
X is -O- or -S-,
Ar ⁵ to Ar ⁷ 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 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 a combination thereof.
The method according to claim 1,
Wherein Ar ¹ and Ar ² are, independently of each other, a substituted or unsubstituted C6 to C30 aryl group.
The method according to claim 1,
Wherein L &^lt; ¹ > to L &^lt; ^{3 & gt} ; are each independently any one of the following substituents:

In this substituent, X is -O- or -S-.
The method according to claim 1,
Wherein the compound for an organic optoelectronic device is any one of the following compounds:

In this compound,
Ar ¹ and Ar ² are, independently of each other, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and the heteroaryl group containing nitrogen in the range of Ar ¹ and Ar ² is Are excluded.
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 organic light emitting device comprising an anode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode,
Wherein at least one of the organic thin film layers comprises the compound for an organic optoelectronic device according to claim 1.
9. The method of claim 8,
Wherein the organic thin film 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.
10. The method of claim 9,
Wherein the compound for an organic optoelectronic device is contained in a hole injection layer or a hole transport layer.
An organic electroluminescence device comprising: an anode; a cathode; and at least one organic thin film layer formed between the anode and the cathode,
The organic thin film layer includes a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, or a combination thereof,
Wherein the organic thin film layer includes a light emitting layer and a plurality of hole transporting layers,
Wherein the hole transporting layer adjacent to the light emitting layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 7 and any one of the hole transporting layers not adjacent to the light emitting layer is a compound represented by the following formula B-1 < / RTI >:< RTI ID = 0.0 &
[Formula B-1]

In the above formula (B-1)
R ¹ to R ⁴ are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, , R ¹ and R ² may form a fused ring together with each other, R ³ and R ⁴ may form a fused ring with each other,
Ar ¹ to Ar ³ independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
L ¹ to L ⁴ independently represent a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 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 n4 independently represent an integer of 0 to 3;
12. The method of claim 11,
Wherein the compound represented by the formula (B-1) is represented by any one of the following formulas (J-1) to (J-144).
[J-1] [J-2] [J-3]

[J-4] [J-5] [J-6]

[J-7] [J-8] [J-9]

[J-10] [J-11] [J-12]

[J-13] [J-14] [J-15]

[J-16] [J-17] [J-18]

[J-19] [J-20] [J-21]

[J-22] [J-23] [J-24]

[J-25] [J-26] [J-27]

[J-28] [J-29] [J-30]

[J-31] [J-32] [J-33]

[J-34] [J-35] [J-36]

[J-37] [J-38] [J-39]

[J-40] [J-41] [J-42]

[J-43] [J-44] [J-45]

[J-46] [J-47] [J-48]

[J-49] [J-50] [J-51]

[J-52] [J-53] [J-54]

[J-55] [J-56] [J-57]

[J-58] [J-59] [J-60]

[J-61] [J-62] [J-63]

[J-64] [J-65] [J-66]

[J-67] [J-68] [J-69]

[J-70] [J-71] [J-72]

[J-73] [J-74] [J-75]

[J-76] [J-77] [J-78]

[J-79] [J-80] [J-81]

[J-82] [J-83] [J-84]

[J-85] [J-86] [J-87]

[J-88] [J-89] [J-90]

[J-91] [J-92] [J-93]

[J-94] [J-95] [J-96]

[J-97] [J-98] [J-99]

[J-100] [J-101] [J-102]

[J-103] [J-104] [J-105]

[J-106] [J-107] [J-108]

[J-109] [J-110] [J-111]

[J-112] [J-113] [J-114]

[J-115] [J-116] [J-117]

[J-118] [J-119] [J-120]

[J-121] [J-122] [J-123]

[J-124] [J-125] [J-126]

[J-127] [J-128] [J-129]

[J-130] [J-131] [J-132]

[J-133] [J-134] [J-135]

[J-136] [J-137] [J-138]

[J-139] [J-140] [J-141]

[J-142] [J-143] [J-144]

12. The method of claim 11,
Wherein the HOMO level of the compound represented by Formula 1 is 5.4 eV or more and 6.0 eV or less.
12. The method of claim 11,
Wherein the triplet excitation energy (T1) of the compound represented by Formula 1 is 2.5 eV or more and 2.9 eV or less.
12. The method of claim 11,
Wherein the HOMO level of the compound represented by the above formula (B-1) is from 5.2 eV to 5.6 eV.
11. A display device comprising the organic light-emitting device according to claim 8 or claim 11.

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