KR20130078749A - Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode - Google Patents

Abstract

PURPOSE: A compound for an organic photoelectric device is provided to manufacture an organic light emitting diode which has excellent electrochemical and thermal stability and having excellent lifetime performance, and to have high luminous efficiency even at a driving voltage. CONSTITUTION: A compound for an organic photoelectric device is represented by chemical formula 1 and has triplet excitation energy (T1) of 2.0 eV or more. An organic light emitting diode (100) has a positive electrode (120), a negative electrode (110), and one or more organic thin film layers (105) inserted into the positive electrode and the negative electrode. At least one layer of the organic thin film layer includes the compound. The organic thin film layer is selected from a light-emitting layer (130), a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and combinations thereof.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

The present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device excellent in lifetime, efficiency, electrochemical stability and thermal stability, an organic light emitting device including the organic optoelectronic device, 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 the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer in the anode and electrons in the cathode, and the injected holes and the electrons meet and recombine by recombination. High 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 fluorescent light emitting materials but also phosphorescent emitting materials can be used as light emitting materials for organic light emitting devices. Such phosphorescence emission is a phenomenon in which electrons are transferred from a ground state to an excited state, The mechanism consists of a non-luminescent transition of a singlet exciton to a triplet exciton through intersystem crossing, followed by a luminescence of the triplet exciton transitioning 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. At this time, the luminous efficiency of the device should be such that the holes and electrons in the light emitting layer are smoothly coupled. However, since the electron mobility of an organic material is generally slower than the hole mobility, in order to efficiently bond holes and electrons in the light-emitting layer, an efficient electron transport layer is used to increase electron injection and mobility from the cathode, It should be able to block the movement of holes.

Further, in order to improve the lifetime, crystallization of the material should be prevented due to joule heat generated when the device is driven. Therefore, it is necessary to develop organic compounds having excellent electron injection and mobility and high electrochemical stability.

A hole injecting and transporting role, or an electron injecting and transporting function, and can function as a light emitting host together with an appropriate dopant.

Life, efficiency, driving voltage, electrochemical stability, and thermal stability, 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).

[Formula 1]

In Formula 1, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxy, ferrocenyl, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, and L ¹ to L ³ are independently a single bond, a substituted or unsubstituted group Is a C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 aquinylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group, n, a and b are Is independently an integer of any one of 0 to 2, R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

The compound for an organic optoelectronic device may be represented by the following formula (2).

[Formula 2]

In Formula 2, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, L ¹ is a single bond, a substituted or unsubstituted C2 to C10 egg A kenylene group, a substituted or unsubstituted C2 to C10 aquinylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n is an integer of any one of 0 to 2 , R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

The compound for an organic optoelectronic device may be represented by the following formula (3).

(3)

In Formula 3, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, R ¹ to R ⁶ are independently hydrogen, deuterium, substituted or unsubstituted A substituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

Ar ¹ and Ar ² may be independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

Ar ¹ and Ar ² are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinoli Nyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or Unsubstituted trizinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothio Phenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenofuranyl group, substituted or unsubstituted indenothiophenyl group, substituted or unsubstituted indolodibenzofuranyl group, substituted or non Hwandoen may be indol Lodi benzo thiophenyl group, a substituted or unsubstituted benzo group tank cover, or a combination thereof.

The compound for an organic optoelectronic device may be represented by any one of the following Formulas a1 to a44.

[Formula a1] [Formula a2] [Formula a3]

[Formula a4] [Formula a5] [Formula a6]

[Formula a7] [Formula a8] [Formula a9]

[Formula a10] [Formula a11] [Formula a12]

[Formula a13] [Formula a14] [Formula a15]

[Formula a16] [Formula a17] [Formula a18]

Formula A19 Formula A20

[Formula a21] [Formula a22] [Formula a23]

[Formula a24] [Formula a25] [Formula a26]

[화학식 a27] [화학식 a28] [화학식 a29]

[Formula a27] [Formula a28] [Formula a29]

[Formula a30] [Formula a31] [Formula a32]

[화학식 a33] [화학식 a34] [화학식 a35]

[Formula a33] [Formula a34] [Formula a35]

[화학식 a36] [화학식 a37] [화학식 a38]

[Formula a36] [Formula a37] [Formula a38]

[Formula a39] [Formula a40] [Formula a41]

[Formula a42] [Formula a43] [Formula a44]

The compound for an organic optoelectronic device may be 2.6 triplet of triplet excitation energy (T1) or more.

The organic optoelectronic device may be 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.

In another embodiment of the present invention, in the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layer is the above-described organic optoelectronic device It provides an organic light emitting device comprising a compound for.

The organic thin film layer may be 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 transport layer or a hole injection layer.

The compound for an organic optoelectronic device may be included in the light emitting layer.

The compound for an organic optoelectronic device can be used as a phosphorescent or fluorescent host material in a light emitting layer.

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

A compound having high hole or electron transporting property, film stability, thermal stability and high triplet excitation energy can be provided.

Such a compound can be used as a hole injecting / transporting material, a host material, or an electron injecting / transporting material of the light emitting layer. The organic optoelectronic device using the organic electroluminescent device has excellent electrochemical and thermal stability, and has excellent lifetime characteristics and 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.

In addition, the substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to Two adjacent substituents among C1 to C10 trifluoroalkyl groups or cyano groups, such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, and a trifluoromethyl group, may be fused 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, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.

"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

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, a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:

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, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

"Aromatic group" means a functional group in which all elements of the ring-form functional group have p-orbital, and these p-orbital forms a conjugation. Specific examples thereof include an aryl group and a heteroaryl group.

An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides 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.

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.

Compound for an organic optoelectronic device according to an embodiment of the present invention may have a structure in which one amino group or a substituted or unsubstituted amine group is bonded to a core of substituted triphenylene.

Therefore, the core structure may be used as a light emitting material, a hole injection material or a hole transport material of an organic optoelectronic device. And may be particularly suitable for a hole injecting material or a hole transporting material.

In addition, the compound for an organic optoelectronic device may be a compound having various energy bandgaps by introducing various substituents to the substituents substituted in 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.

According to an embodiment of the present invention, the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device represented by the following formula (1).

[Formula 1]

In Formula 1, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxy, ferrocenyl, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, and L ¹ to L ³ are independently a single bond, a substituted or unsubstituted group Is a C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 aquinylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group, n, a and b are Is independently an integer of any one of 0 to 2, R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

Due to the substituent, the compound for an organic optoelectronic device may exhibit luminescence, hole or electron characteristics; Membrane stability; Thermal stability and high triplet excitation energy (T1).

L ¹ to L ^{3 each} independently represent a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 arylene group, a substituted or unsubstituted C6 to C30 arylene group, Lt; RTI ID = 0.0 > C2-C30 < / RTI > heteroarylene group.

The L ¹ to L ³ may serve to adjust the conjugation (conjugation) length on the molecular structure, thereby adjusting the HOMO energy level and T1 energy of the compound.

Specific examples of the L ¹ to L ³ are substituted or unsubstituted phenylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted terphenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted Anthracenylene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or Unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenofuranyl group, substituted or unsubstituted Indenothiophenyl group, substituted or unsubstituted indolodibenzofuranyl group, substituted or unsubstituted indolodibenzothiophenyl group, substituted or unsubstituted benzocarbazoyl group, and the like.

Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 Alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or Unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 To C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoyl Amino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiol group , Substituted or unsubstituted C1 to C20 ureide group, substituted or unsubstituted C3 to C40 silyl group, or a combination thereof.

More specifically, Ar ¹ and Ar ² may be independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

More specifically, Ar ¹ and Ar ² are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted Isoquinolinyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidy Neyl group, substituted or unsubstituted trizinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted Dibenzothiophenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenofuranyl group, substituted or unsubstituted indenothiophenyl group, substituted or unsubstituted indolodibenzofuranyl Groups, substituted or unsubstituted indolodibenzothiophenyl groups, substituted or unsubstituted benzocarbazoyl groups, or a combination thereof.

By controlling the substituents of Ar ¹ and Ar ² it can be prepared in bulk structure of the compound, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.

In addition, the structure of the asymmetric bipolar (bipolar) characteristics can be prepared by an appropriate combination of the substituents of Ar ¹ and Ar ² , the structure of the asymmetric bipolar characteristics to improve the hole and electron transfer ability to improve the luminous efficiency and performance of the device You can expect an improvement.

The compound for an organic optoelectronic device may be represented by the following formula (2).

[Formula 2]

In Formula 2, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, L ¹ is a single bond, a substituted or unsubstituted C2 to C10 egg A kenylene group, a substituted or unsubstituted C2 to C10 aquinylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n is an integer of any one of 0 to 2 , R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

Portions corresponding to Formula 1 of the compound represented by Formula 2 will be omitted since the description is duplicated.

In the case of the compound represented by Formula 2, since the substituent may be bonded to the amine group of Formula 1 without a linking group, it may be suitable as a hole transport layer of phosphorescent blue and phosphorescent green devices with high T1 energy.

The compound for an organic optoelectronic device may be represented by the following formula (3).

(3)

In Formula 3, Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted A substituted 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 aryl Oxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted Or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to A 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, R ¹ to R ⁶ are independently hydrogen, deuterium, substituted or unsubstituted A substituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

Portions corresponding to Formula 2 of the compound represented by Formula 3 will be omitted since the description is duplicated.

In the case of the compound represented by Chemical Formula 3, the L ¹ linking group of Chemical Formula 2 is omitted.

Specific examples of the compound for an organic optoelectronic device include, but are not limited to, a compound represented by any one of the following Formulas a1 to a44.

[Formula a1] [Formula a2] [Formula a3]

[Formula a4] [Formula a5] [Formula a6]

[Formula a7] [Formula a8] [Formula a9]

[Formula a10] [Formula a11] [Formula a12]

[Formula a13] [Formula a14] [Formula a15]

[Formula a16] [Formula a17] [Formula a18]

Formula A19 Formula A20

[Formula a21] [Formula a22] [Formula a23]

[Formula a24] [Formula a25] [Formula a26]

[화학식 a27] [화학식 a28] [화학식 a29]

[Formula a27] [Formula a28] [Formula a29]

[Formula a30] [Formula a31] [Formula a32]

[화학식 a33] [화학식 a34] [화학식 a35]

[Formula a33] [Formula a34] [Formula a35]

[화학식 a36] [화학식 a37] [화학식 a38]

[Formula a36] [Formula a37] [Formula a38]

[Formula a39] [Formula a40] [Formula a41]

[Formula a42] [Formula a43] [Formula a44]

When the compound according to the embodiment of the present invention requires both electronic and hole characteristics, introducing a functional group having the hole characteristics is effective in improving the lifespan and driving voltage of the organic light emitting diode.

The compound for an organic optoelectronic device according to one embodiment of the present invention has a maximum emission wavelength in a range of about 320 to 500 nm and a triplet excitation energy (T1) in a range of 2.0 eV or more, more specifically 2.0 to 4.0 eV The charge of a host having a high triplet excitation energy can be transferred to the dopant to increase the luminous efficiency of the dopant and freely adjust the HOMO and LUMO energy levels of the material to lower the driving voltage It can be very useful as a host material or a charge transport material.

In addition, since the compound for organic optoelectronic devices has a photoactive and electrical activity, it can be used as a nonlinear optical material, an electrode material, a coloring material, an optical switch, a sensor, a module, a waveguide, an organic transistor, it can be very usefully applied to materials such as a membrane.

The compound for organic optoelectronic devices including the above compound has a glass transition temperature of 90 ° C or higher and a thermal decomposition temperature of 400 ° C or higher, which is excellent in thermal stability. As a result, it is possible to realize a highly efficient organic photoelectric device.

The compound for organic optoelectronic devices including the above-described compounds can play a role of luminescent host together with a suitable dopant, and can play a role of luminescence, electron injection and / or transport. That is, the compound for an organic optoelectronic device can be used as a phosphorescent or fluorescent host material, a blue luminescent dopant material, or an electron transporting material.

Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.

Accordingly, one embodiment of the present invention provides an organic optoelectronic device including the compound for an organic optoelectronic device. Here, the organic photoelectrode refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoconductor drum, an organic memory device, or the like. In particular, in the case of an organic solar cell, the compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency. In the case of an organic transistor, an electrode material in a gate, a source- Can be used.

Hereinafter, the organic light emitting device will be described in detail.

Another embodiment of the present invention is an organic light emitting device comprising a cathode, a cathode, and at least one or more organic thin film layers interposed between the anode and the cathode, wherein at least one of the organic thin film layers is an organic thin film And a compound for an organic optoelectronic device according to the present invention.

The organic thin film layer that may include the compound for an organic optoelectronic device may include a layer 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, At least one of the layers includes the compound for organic optoelectronic devices according to the present invention. In particular, the hole transport layer or the hole injection layer may include the compound for organic optoelectronic devices according to an embodiment of the present invention. When the compound for an organic optoelectronic device is contained in the light emitting layer, the compound for the organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.

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 include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). And metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO ₂ and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) 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 may be used as 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 include compounds for the organic optoelectronic devices. At this time, the compound for an organic optoelectronic device can be used for the electron transport layer 150 or the electron transport layer 150 including the electron injection layer 160, and when included in the electron transport layer, a hole blocking layer (not shown) It is not necessary to form them separately, and an organic light emitting device having a more simplified structure can be provided.

When the compound for an organic optoelectronic device is contained in the light emitting layers 130 and 230, the compound for the organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.

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.

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

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)

Example  1: Preparation of Intermediates A, B and C

Triphenylene derivative represented by the following formula (C) can be prepared through the synthetic route of Scheme 1.

[Reaction Scheme 1]

Example  1-1: Preparation of Intermediate A

50 g (0.240 mol) of 2,7-dibromophenanthrene-9,10-dione, 1,3-bis (4-boromophenyl) propa-2-one (1000 ml, three-necked round bottom flask) 80 g of 1,3-bis (4-bromophenyl) propan-2-one) and 500 ml of ethanol were added and stirred. Potassium hydroxide and 30 g of KOH were added to the solution and stirred at 50 ° C. for 5 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 70 g (yield 60%) of the target compound A.

Example  1-2: Preparation of Intermediate B

In a 500 ml three-necked round bottom flask, 58 g (0.102 mol) of the compound of Formula A prepared in Example 1-1 were diluted with 250 ml of o-xylene and 20 g of trimethylsilylacetylene was added under a nitrogen atmosphere. The mixture was refluxed for 12 hours, cooled to room temperature, and poured into excess methanol to precipitate a solid. The precipitated solid was filtered, washed with methanol, and then vacuum-dried to obtain 52.5 g (yield: 85%) of the target compound B.

Example  1-3: Preparation of Intermediate C

50 g (0.081 mol) of Formula B compound prepared in Example 1-2, 2000 ml, 800 ml tetrahydrofuran (hereinafter THF) in a 2000 ml, three-necked round bottom flask, tetrabutylammonium fluoride (1 M in THF) ) 100 ml were added sequentially. After stirring for 8 hours at room temperature, the mixture was extracted using distilled water and chloroform. The organic layer was separated, concentrated, and methanol was added to the precipitated solid. The precipitated solid was filtered and dried to give 43.2 g (yield 97%) of the title compound C.

LC-Mass (M + H < + >): calc. 535.98, found 535.98

Example  2: Preparation of Intermediates D, E, F and G

The triphenylene derivative represented by the following formula F can be prepared through the synthetic route of Scheme 2, which is almost similar to Scheme 1.

[Reaction Scheme 2]

Example  2-1: Preparation of Intermediate D

1000 g, 50 g (0.240 mol) of 2,7-dibromophenanthrene-9,10-dione, 1- (4-bromophenyl) -3-phenylpropa-2-one in a three-neck round bottom flask 80 g of (1- (4-bromophenyl) -3-phenylpropan-2-one) and 500 ml of ethanol were added and stirred. Potassium hydroxide and 30 g of KOH were added to the solution and stirred at 50 ° C. for 5 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 70 g (yield 60%) of the target compound A.

Example  2-2: Preparation of Intermediate E

In a 500 ml three-necked round bottom flask, 58 g (0.102 mol) of the compound of Formula A prepared in Example 1-1 were diluted with 250 ml of o-xylene and 20 g of trimethylsilylacetylene was added under a nitrogen atmosphere. The mixture was refluxed for 12 hours, cooled to room temperature, and poured into excess methanol to precipitate a solid. The precipitated solid was filtered, washed with methanol, and then vacuum-dried to obtain 52.5 g (yield: 85%) of the target compound B.

Example  2-3: Preparation of Intermediate F

50 g (0.081 mol) of Formula B compound prepared in Example 1-2, 2000 ml, 800 ml tetrahydrofuran (hereinafter THF) in a 2000 ml, three-necked round bottom flask, tetrabutylammonium fluoride (1 M in THF) ) 100 ml were added sequentially. After stirring for 8 hours at room temperature, the mixture was extracted using distilled water and chloroform. The organic layer was separated, concentrated, and methanol was added to the precipitated solid. The precipitated solid was filtered and dried to give 43.2 g (yield 97%) of the title compound C.

LC-Mass (M + H < + >): calc. 535.98, found 535.98

Example  2-4: Preparation of Intermediate G

Compound F obtained in the above 2-3 (50 g, 109 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-ooctamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane)) (33.2 g , 131 mmol), Pd (dffp) ₂ Cl ₂ (4.0 g, 5.00 mmol), and potassium acetate (13.4 g, 136 mmol) were placed in a flask and dissolved in 600 mL of 1,4-dioxane under a nitrogen atmosphere for 12 hours. Stirred at reflux.

After completion of the reaction, 400 ml of ice water was added, extracted three times with 50 ml of dichloromethane, and the obtained extract was dried with excess magnesium sulfite, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane: dichloromethane = 4: 1 (v: v)) to give a pale yellow compound (46.9 g, yield 85%).

Example  3-1: Final Compound Synthesis

In a three-neck 250 ml round bottom flask, 15.0 g of intermediate C or F, 1.2 equivalents of secondary amine for intermediate C or F, 1.2 equivalents of sodium tert-butoxide, Pd (dba) ₂ [(Tris (dibenzylidine acetone) dipalladium ( 0))] 0.01 equivalent and 0.03 equivalent of tri (tert-butyl) phosphine were dissolved in 200 mL of toluene, and then reacted at 110 ° C for 12 hours.

After the reaction was completed, the reaction mixture was cooled to room temperature, 100 ml of distilled water was added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated and separated by silica gel column chromatography. The eluate thus obtained was concentrated and dried to obtain a target compound in the solid state, and the target compound was confirmed by using LCMS.

Table 1 below shows the kind of the product obtained using the intermediate C or F and the secondary aryl amine through the reaction of the above example.

Example  3-2: Final Compound Synthesis

Dissolve 15.0 g of intermediate G and 0.021 equivalent Pd (PPh ₃ ) ₄ [Tetrakis (triphenylphosphin) palladium (0))] in 300 mL tetrahydrofuran in a three-neck 250 ml round bottom flask. After adding 8 equivalents of 2 MK ₂ CO ₃ aqueous solution, the reaction was carried out at 80 ° C. for 12 hours.

After the reaction was completed, the reaction mixture was cooled to room temperature, 100 ml of distilled water was added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated and separated by silica gel column chromatography. The eluate thus obtained was concentrated and dried to obtain a target compound in the solid state, and the target compound was confirmed by using LCMS.

Table 1 below shows the kinds of products obtained using intermediate F or G and aryl halide through the reaction of the above examples.

No Intermediate type Secondary amine structure
Or aryl halide structure Final composite structure Yield and
LC Mass Data (M + H ⁺ ) Example 3-1-1 Compound F

78%
700.30 Example 3-1-2 Compound F

83%
879.31 Example 3-1-3 Compound F

89%
740.33 Example 3-1-4 Compound F

91%
865.36 Example 3-1-5 Compound F

93%
905.39 Example 3-2-1 Compound G

88%
622.26 Example 3-2-2 Compound G

89%
672.27 Example 3-2-3 Compound G

92%
712.27 Example 3-2-4 Compound G

85%
828.33 Example 3-2-5 Compound G

83%
728.24 Example 3-2-6 Compound G

79%
738.32 Example 3-2-7 Compound G

80%
662.30

(Production of organic light emitting device)

Example  4: Example  Holes Compounds of 3-1-1 With transport layer  Manufacture of Organic Light Emitting Diodes (Blue Fluorescent Devices)

The anode was cut into a corning 15Ωcm (1200Å) ITO glass substrate, 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned for 5 minutes with isopropyl alcohol and pure water, and then irradiated with ultraviolet rays for 30 minutes and exposed to ozone. The glass substrate was installed in a vacuum deposition apparatus.

First, 2-TNATA (see formula below), a well-known compound, was vacuum deposited on the substrate to form a thickness of 600 kPa, and then the compound of Example 3-1 was vacuum deposited to a thickness of 300 kPa as the hole transport layer. It was.

A light emitting layer was formed on the hole transport layer by simultaneously depositing a known blue phosphorescent host IDE215 (Idemitsu Co., Ltd.) and a known blue fluorescent dopant IDE118 (Idemitsu Co., Ltd.) at a weight ratio of 98: 2.

Subsequently, Alq ₃ was deposited on the emission layer with an electron transport layer at a thickness of 300 kW, LiF, which is a halogenated alkali metal, was deposited on the electron transport layer, at an electron transport layer, at a thickness of 10 kW, and Al was deposited at a thickness of 3000 kW (cathode electrode). An organic light emitting diode was manufactured by vacuum deposition to form a LiF / Al electrode. The results are shown in Table 2 below.

[2-TNATA]

Example  5: Example  Hole in the compound of 3-1-2 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-1-2 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  6: Example  Holes Compounds of 3-1-3 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-1-3 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  7: Example  Holes Compounds of 3-1-4 With transport layer  Fabrication of organic light emitting device

An organic light emitting device was manufactured in the same manner as in Example 4, except that the compound of Example 3-1-4, instead of compound 3-1-1, was used to form the hole transport layer. The results are shown in Table 2 below.

Example  8: Example  Holes Compounds of 3-1-5 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-1-5 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  9: Example  Holes in the compound of 3-2-1 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-2-1 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  10: Example  Hole in the compound of 3-2-2 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-2-2 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  11: Example  Holes Compound of 3-2-3 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-2-3 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  12: Example  Holes Compound of 3-2-4 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-2-4 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Example  13: Example  Holes in the compound of 3-2-5 With transport layer  Fabrication of organic light emitting device

An organic light emitting device was manufactured in the same manner as in Example 4, except that the compound of Example 3-2-5, instead of compound 3-1-1, was used to form the hole transport layer. The results are shown in Table 2 below.

Example  14: Example  Holes Compound of 3-2-6 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound of Example 3-2-6 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 2 below.

Comparative example  1: Notice NPB Holes With transport layer  Fabrication of organic light emitting device

N, N'-bis- (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) which is a known substance instead of the compound of Example 3-1-1 when forming the hole transport layer ) -4,4'-diamine (NPB, N, N'-Bis- (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine) Except for using the organic light emitting device was manufactured in the same manner as in Example 4. The device had a driving voltage of 4.8 V, a current density of 13.9 mA / cm 2 at a light emission luminance of 1000 nits, a color coordinate of (0.133, 0.139), and a light emission efficiency of 6.2 cd / A.

[NPB]

Example  15: Example  Holes Compounds of 3-1-1 With transport layer  Of organic light emitting diodes (green phosphorescent)

The anode was cut into a corning 15Ωcm (1200Å) ITO glass substrate, 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned for 5 minutes with isopropyl alcohol and pure water, and then irradiated with ultraviolet rays for 30 minutes and exposed to ozone. The glass substrate was installed in a vacuum deposition apparatus.

A well-known compound 2-TNATA (see the above formula) was vacuum deposited on the substrate to form a thickness of 800 kPa, followed by the compound of Example 3-1-1 to a thickness of 400 kPa as the hole transport layer. Vacuum deposition.

A light emitting layer was formed on the hole transport layer by simultaneously depositing a known green phosphorescent host CBP (see the following formula) and a known green phosphorescent dopant Ir (PPy) ₃ in a weight ratio of 93:72. Then, BAlq [Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum] 50um and Alq3 [Tris (8-hydroxyquinolinato) aluminium] 250Å Laminated sequentially to form an electron transport layer. An organic light emitting device was manufactured by depositing LiF, which is an alkali metal halide, on the electron transport layer with an electron injecting layer to a thickness of 10 kPa, and vacuum depositing Al to a thickness of 3000 kPa (cathode electrode) to form a LiF / Al electrode. The results are shown in Table 3 below.

[CBP]

Example  16: Example  Hole in the compound of 3-1-2 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-1-2 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  17: Example  Holes Compounds of 3-1-3 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-1-3 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  18: Example  Holes Compounds of 3-1-4 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-1-4 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  19: Example  Holes Compounds of 3-1-5 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-1-5 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  20: Example  Holes in the compound of 3-2-1 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-2-1 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  21: Example  Hole in the compound of 3-2-2 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-2-2 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  22: Example  Holes Compound of 3-2-3 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-2-3 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  23: Example  Holes Compound of 3-2-4 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-2-4 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Example  24: Example  Holes in the compound of 3-2-5 With transport layer  Fabrication of organic light emitting device

An organic light emitting device was manufactured in the same manner as in Example 15, except that the compound of Example 3-2-5, instead of compound 3-1-1, was used to form the hole transport layer. The results are shown in Table 3 below.

Example  25: Example  Holes Compound of 3-2-6 With transport layer  Fabrication of organic light emitting device

An organic light emitting diode was manufactured according to the same method as Example 15 except for using the compound of Example 3-2-6 instead of compound 3-1-1 when forming the hole transport layer. The results are shown in Table 3 below.

Comparative example  2: known NPB Holes With transport layer  Fabrication of organic light emitting device

Except for using the known material 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as NPB) instead of the compound of Example 3-1-1 when forming the hole transport layer In the same manner as in Example 15, an organic light emitting device was manufactured. The results are shown in Table 3 below.

[NPB]

Comparative example  3: Holes for the compound represented by the following Chemical Formula R-1 With transport layer  Fabrication of organic light emitting device

An organic light emitting device was manufactured in the same manner as in Example 15, except that the compound of Formula R-1, instead of Compound 3-1-1, was used to form the hole transport layer. The results are shown in Table 3 below.

[Chemical formula R-1]

(Performance Measurement of Organic Light Emitting Device)

For each organic light emitting device manufactured in Examples 4 to 25 and Comparative Examples 1 to 3, current density change, luminance change, and luminous efficiency according to voltage were measured. The specific measuring method is as follows.

(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-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.

(2) Measurement of luminance change according to voltage change

The resulting organic light emitting device was measured by using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.

(3) Measurement of luminous efficiency

Current efficiency (cd / A) and power efficiency (lm / W) of the same brightness (1,000 cd / m ² or 3,000 cd / m ² ) using the brightness, current density and voltage measured from (1) and (2) above ) Was calculated.

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

Device data for each of the organic light emitting diodes manufactured in Examples 4 to 14 and Comparative Example 1 are as shown in Table 2 below.

As can be seen in Table 2, it can be seen that the characteristics of the device according to the embodiment of the present invention is excellent.

Blue fluorescent element 1000 cd / m ² The driving voltage (V) Current density (mA / ㎠) The luminous efficiency (cd / A) Color coordinates Example 4 5.1 12.3 6.1 (0.133, 0.140) Example 5 5.2 12.0 5.9 (0.133, 0.139) Example 6 5.0 11.8 6.3 (0.133, 0.139) Example 7 4.9 12.0 6.5 (0.133, 0.138) Example 8 4.7 13.1 6.8 (0.133, 0.139) Example 9 5.3 12.8 6.6 (0.133, 0.139) Example 10 5.2 12.7 6.3 (0.133, 0.139) Example 11 5.2 12.5 6.1 (0.133, 0.138) Example 12 5.1 12.1 5.6 (0.133, 0.138) Example 13 5.3 12.6 6.7 (0.133, 0.138) Example 14 5.1 12.3 6.5 (0.133, 0.140) Comparative Example 1 5.0 13.4 5.6 (0.133, 0.140)

Device data of each of the organic light emitting diodes manufactured in Examples 15 to 25 and Comparative Examples 2 and 3 are shown in Table 2 below.

As can be seen in Table 3, it can be seen that the characteristics of the device according to the embodiment of the present invention is excellent.

Green phosphor 3000 cd / m ² The driving voltage (V) Current density (mA / ㎠) The luminous efficiency (cd / A) Color coordinates Example 15 5.6 10.2 60.7 (0.340, 0.622) Example 16 5.7 11.3 59.8 (0.341, 0.621) Example 17 5.5 9.8 62.4 (0.339, 0.623) Example 18 5.2 9.5 56.1 (0.338, 0.623) Example 19 5.1 8.4 58.5 (0.338, 0.623) Example 20 5.4 10.2 57.9 (0.340, 0.622) Example 21 5.4 9.6 59.8 (0.339, 0.623) Example 22 5.3 9.1 60.1 (0.338, 0.623) Example 23 5.5 10.1 58.5 (0.340, 0.623) Example 24 5.3 8.9 56.4 (0.338, 0.623) Example 25 5.1 8.7 57.3 (0.338, 0.621) Comparative Example 2 5.0 10.5 49.3 (0.340, 0.621) Comparative Example 3 4.8 9.6 45.2 (0.340, 0.622)

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 (14)

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

In Chemical Formula 1,
Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 Alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or Unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 To C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoyl Amino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiol group , Substituted or unsubstituted C1 to C20 ureide group, substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
L ¹ to L ³ are independently a single bond, 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 or a substituted or unsubstituted C2 to C30 heteroarylene group,
n, a and b are independently an integer of any one of 0 to 2,
R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The method of claim 1,
Wherein the compound for an organic optoelectronic device is represented by the following Formula 2:
(2)

In Formula 2,
Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 Alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or Unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 To C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoyl Amino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiol group , Substituted or unsubstituted C1 to C20 ureide group, substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
L ¹ is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 aquinylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 hetero Arylene group,
n is an integer of any one of 0 to 2,
R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The method of claim 1,
The compound for an organic optoelectronic device is a compound for an organic optoelectronic device is represented by the following formula (3):
(3)

In Formula 3,
Ar ¹ and Ar ² are independently hydrogen, deuterium, halogen, cyano, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 Alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or Unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 To C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoyl Amino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiol group , Substituted or unsubstituted C1 to C20 ureide group, substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
4. The method according to any one of claims 1 to 3,
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 compound for an organic optoelectronic device.
5. The method of claim 4,
Ar ¹ and Ar ² are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinoli Nyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or Unsubstituted trizinyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothio Phenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenofuranyl group, substituted or unsubstituted indenothiophenyl group, substituted or unsubstituted indolodibenzofuranyl group, substituted or non Hwandoen indole Lodi benzo thiophenyl group, a substituted or unsubstituted benzoyl group or a tank cover would The compound for an organic optoelectronic device combinations thereof. The method of claim 1,
Compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas a1 to a44.
[Formula a1] [Formula a2] [Formula a3]

[Formula a4] [Formula a5] [Formula a6]

[Formula a7] [Formula a8] [Formula a9]

[Formula a10] [Formula a11] [Formula a12]

[Formula a13] [Formula a14] [Formula a15]

[Formula a16] [Formula a17] [Formula a18]

Formula A19 Formula A20

[Formula a21] [Formula a22] [Formula a23]

[Formula a24] [Formula a25] [Formula a26]

[Formula a27] [Formula a28] [Formula a29]

[Formula a30] [Formula a31] [Formula a32]

[Formula a33] [Formula a34] [Formula a35]

[Formula a36] [Formula a37] [Formula a38]

[Formula a39] [Formula a40] [Formula a41]

[Formula a42] [Formula a43] [Formula a44]

The method of claim 1,
Wherein the compound for an organic optoelectronic device has a triplet excitation energy (T1) of 2.0 eV or more.
The method of claim 1,
Wherein the organic optoelectronic device is 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,
At least one of the organic thin film layer is an organic light emitting device comprising a compound for an organic optoelectronic device according to any one of claims 1 to 8.
10. The method of claim 9,
The organic thin film layer is selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
The method of claim 10,
The compound for an organic optoelectronic device is an organic light emitting device which is contained in a hole transport layer or a hole injection layer.
The method of claim 10,
Wherein the compound for an organic optoelectronic device is contained in a light emitting layer.
The method of claim 12,
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 9.

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