KR20130074765A - 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 light electric component is provided to present an organic light electric component with a long lifetime, high efficiency, and electrochemical and thermal stabilities by having high electron transport capacity, film stability, thermal stability and triplet excitation energy. CONSTITUTION: A compound for organic light electric component is indicated in the chemical formula 1. In the chemical formula1, Ar^1 is a substituted or a non-substituted C6-30 aryl group, the Ar^2 is a substituted or a non-substituted pyridinyl group or pyrimidinyl based or triazinyl, the R^1 and the R^2 are respectively hydrogen, deuterium, a substituted or a non-substituted C1-10 alkyl group, a substituted or a non-substituted C6-30 aryl group, and a substituted or a non-substituted C2-30 heteroaryl group, or their combination, the L is a single bond, a substituted or a non-substituted C2-10 alkenylene group, a substituted or a non-substituted alkynylene group, a substituted or a non-substituted C6-30 arylene group, a substituted or a non-substituted C2-30 heteroarylene group or their combination, and the Ar^3 is hydrogen, deuterium, or a substituted or a non-substituted C6-30 aryl group or a substituted or a non-substituted C2-30 heteroaryl group.

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 is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ and R ² are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene group or a combination thereof, n is 0 or 3, and Ar ³ is hydrogen, deuterium, 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 represented by Formula 1 may be represented by the following Formula 2.

[Formula 2]

In Formula 2, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ and R ² are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene group or a combination thereof, n is 0 or 3, and Ar ³ is hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted Dibenzofuranyl group or a combination thereof.

Ar ³ may be hydrogen.

Ar ² may be selected from any one of the following Formulas S-1 to S-5.

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

Formula S-5

In S-1 and S-2, * represents a bonding position, in Formulas S-3 to S-5, R ¹ to R ⁴ are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group Or a combination thereof, in Formulas S-3 and S-4, any one of R ¹ to R ⁴ represents a binding position, and in Formula S-5, any one of R ¹ to R ³ represents a binding position. Indicates.

Ar ³ may be selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenyl group.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 3.

(3)

In Formula 3, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, X is -NR'-, -S- or -O-, R 'is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group, substituted or unsubstituted A C2 to C30 hetero aryl group, or a combination thereof.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 4.

[Formula 4]

In Formula 4, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, Ar ⁴ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 5.

[Chemical Formula 5]

In Formula 5, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, Ar ⁴ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-1.

[Formula ad-1]

In Formula ad-1, X ¹ to X ⁸ are each independently, -CR'- or N, and R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, at least one of X ¹ to X ³ is N, and at least one of X ⁴ to X ⁸ is N.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-2.

[Formula ad-2]

In Formula ad-2, X ¹ to X ³ are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and at least one of X ¹ to X ³ is N.

The compound for an organic optoelectronic device may be represented by the formula A-1 to A-36.

[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5] [Formula A-6]

[Formula A-7] [Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11] [Formula A-12]

[Formula A-13] [Formula A-14] [Formula A-15]

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

[Formula A-19] [Formula A-20] [Formula A-21]

[Formula A-22] [Formula A-23] [Formula A-24]

[Formula A-25] [Formula A-26] [Formula A-27]

[Formula A-28] [Formula A-29] [Formula A-30]

[Formula A-31] [Formula A-32] [Formula A-33]

[Formula A-34] [Formula A-35] [Formula A-36]

The compound for an organic optoelectronic device may be represented by the following formula B-1 to B-96.

[Formula B-1] [Formula B-2] [Formula B-3]

[Formula B-4] [Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8] [Formula B-9]

[Formula B-10] [Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14] [Formula B-15]

[Formula B-16] [Formula B-17] [Formula B-18]

Formula B-19 Formula B-20 Formula B-21

[Formula B-22] [Formula B-23] [Formula B-24]

[Formula B-25] [Formula B-26] [Formula B-27]

[Formula B-28] [Formula B-29] [Formula B-30]

[Formula B-31] [Formula B-32] [Formula B-33]

[Formula B-34] [Formula B-35] [Formula B-36]

[Formula B-37] [Formula B-38] [Formula B-39]

[Formula B-40] [Formula B-41] [Formula B-42]

[Formula B-43] [Formula B-44] [Formula B-45]

[Formula B-46] [Formula B-47] [Formula B-48]

[Formula B-49] [Formula B-50] [Formula B-51]

[Formula B-52] [Formula B-53] [Formula B-54]

[Formula B-55] [Formula B-56] [Formula B-57]

[Formula B-58] [Formula B-59] [Formula B-60]

[Formula B-61] [Formula B-62] [Formula B-63] [Formula B-64]

[Formula B-65] [Formula B-66] [Formula B-67] [Formula B-68]

[Formula B-69] [Formula B-70] [Formula B-71] [Formula B-72]

[Formula B-74] [Formula B-74] [Formula B-75] [Formula B-76]

[Formula B-77] [Formula B-78] [Formula B-79] [Formula B-80]

[Formula B-81] [Formula B-82] [Formula B-83] [Formula B-84]

[Formula B-85] [Formula B-86] [Formula B-87] [Formula B-88]

[Formula B-89] [Formula B-90] [Formula B-91] [Formula B-92]

[Formula B-93] [Formula B-94] [Formula B-95] [Formula B-96]

The compound for an organic optoelectronic device may be represented by the formula C-1 to C-49.

[C-1] [C-2] [C-3]

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

[C-7] [C-8] [C-9]

[C-10] [C-11] [C-12]

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

[C-16] [C-17] [C-18]

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

[C-22] [C-23] [C-24]

[C-25] [C-26] [C-27]

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

[C-31] [C-32] [C-33]

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

[C-37] [C-38] [C-39]

[C-40] [C-41] [C-42]

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

[C-46] [C-47] [C-48]

[C-49]

The compound for an organic optoelectronic device may be represented by the following formula D-1 to D-20.

[D-1] [D-2] [D-3]

[D-4] [D-5]

[D-6] [D-7] [D-8]

[D-9] [D-10]

[D-11] [D-12] [D-13]

[D-14] [D-15]

[D-16] [D-17] [D-18]

[D-19] [D-20]

The compound for an organic optoelectronic device may have a triplet excitation energy (T1) of 2.0 eV 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. The alkyl group may be branched, straight-chain or cyclic.

"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 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:

For example, the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohex It means a practical skill.

"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 carbazole derivative refers to a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is substituted with a hetero atom or carbon instead of nitrogen. Specific examples thereof include dibenzofuran (dibenzofuranyl group), dibenzothiophene (dibenzothiophenyl group), fluorene (fluorenyl group) and the like.

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 is a substituted or unsubstituted aryl group is bonded to the nitrogen of the substituted or unsubstituted carbazole, substituted or unsubstituted pyridinyl group, substituted or unsubstituted in the carbazole It may have a core structure in which a substituted pyrimidinyl group or a substituted or unsubstituted triazinyl group is bonded.

The substituted or unsubstituted carbazole is a compound having both hole properties and electronic properties. More specifically, hole properties may be slightly better than electronic properties. However, this may be controlled by a substituent attached to the carbazole.

The substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, or substituted or unsubstituted triazinyl group is a substituent having excellent electronic properties.

By combining a substituent having excellent electronic properties with a carbazole having the hole and electronic properties, the electronic and hole properties of the entire compound may be adjusted.

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. In particular, it may be suitable for the light emitting material.

At least one of the substituents bonded to the core may be a substituent having hole characteristics. Therefore, the compound may satisfy the conditions required in the light emitting layer by reinforcing hole characteristics in the core structure. More specifically, it can be used as a host material of the light emitting layer.

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 is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ and R ² are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene group or a combination thereof, n is 0 or 3, and Ar ³ is hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

R ¹ and R ² are independently 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, or a combination thereof .

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 is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof. The L may be selectively adjusted to determine the conjugation length of the entire compound, and the crystallinity and solubility of the entire compound may be adjusted according to the binding position.

Specific examples of the L 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 anthracenylene group, Substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group, dibenzofurenylene group, dibenzothiophenylene group, thiophenylene group and the like.

The Ar ¹ may be a substituted or unsubstituted C6 to C30 aryl group. Specific examples of Ar1 may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or And an unsubstituted triphenylenyl group.

Due to the presence of Ar ¹ it is possible to improve the thermal stability of the compound and to control the degree of packing between the compounds, thereby controlling the intermolecular stacking.

Ar ¹ may be a substituted or unsubstituted triphenylenyl group. Since the substituted or unsubstituted triphenylenyl group has a bulky structure and produces a resonance effect, the substituted or unsubstituted triphenylenyl group has an effect of suppressing side reactions that may occur in the solid state, thereby increasing the performance of the organic light emitting device.

It can also have the effect of bulking the compound to lower the crystallinity and increase its lifetime.

Unlike the other substituents, the triphenylenyl group has a wider bandgap and a triplet excitation energy, so that the triphenylenyl group does not reduce the bandgap or triplet excitation energy of the compound by binding to carbazole, and thus has a greater advantage.

The compound for an organic optoelectronic device represented by Formula 1 may be represented by the following Formula 2.

[Formula 2]

In Formula 2, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ and R ² are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene group or a combination thereof, n is 0 or 3, and Ar ³ is hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

When L and Ar ³ are sequentially combined as in the compound represented by Formula 2, synthesis of the entire compound may be advantageous. In addition, the stability of the compound can be increased by substituting position 3 of the most reactive carbazole.

More specifically, Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, substituted Or an unsubstituted dibenzofuranyl group or a combination thereof.

For example, when Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenyl group, the effect of substituting the most reactive 3 position in carbazole can be expected. By substituting a stable aromatic compound, improvement of thermal stability and glass transition temperature by molecular weight increase can be expected. In addition, by introducing a bulky aromatic substituent, the non-planarity of the material can be improved, and the effect of poor crystallinity can be expected.

For another example, when Ar ³ is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzofuranyl group, hole injection and transport which may be insufficient with carbazole alone Increasing the role allows the entire compound to exhibit bipolar properties.

When Ar ³ is hydrogen, the molecular weight is reduced, so that the deposition temperature is lowered, thereby improving processability in fabricating a device.

More specifically, the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (3).

(3)

In Formula 3, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, X is -NR'-, -S- or -O-, R 'is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group, substituted or unsubstituted A C2 to C30 hetero aryl group, or a combination thereof.

When the carbazolyl derivative has a hole property as shown in Formula 3, since the carbazolyl derivative has hole properties, the hole injection and transport properties of the entire compound may be improved, and thus the electron and hole properties may be appropriately controlled. .

More specifically, the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (4).

[Formula 4]

In Formula 4, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, Ar ⁴ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof.

When having a bicarbazole-type bond as shown in Formula 4, there is an advantage that the hole injection and transport properties are improved compared to the carbazole.

More specifically, the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (5).

[Chemical Formula 5]

In Formula 5, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group R ¹ to R ⁵ are independently 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, or a combination thereof , L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group or a combination thereof, n is 0 or 3, Ar ⁴ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof.

When the binding position of the bicarbazole structure is the third position of each carbazole as shown in Formula 5, it may be advantageous in terms of ease of synthesis and increasing stability of the compound by replacing the third position, which is more reactive than the other positions. have.

Ar ² may be selected from any one of the following Formulas S-1 to S-5.

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

Formula S-5

In S-1 and S-2, * represents a bonding position, in Formulas S-3 to S-5, R ¹ to R ⁴ are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group Or a combination thereof, in Formulas S-3 and S-4, any one of R ¹ to R ⁴ represents a binding position, and in Formula S-5, any one of R ¹ to R ³ represents a binding position. Indicates.

When Ar ² is any one of Formulas S-1 to S-5, electron injection and transport characteristics may be adjusted according to each substituent.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-1.

[Formula ad-1]

In Formula ad-1, X ¹ to X ⁸ are each independently, -CR'- or N, and R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, at least one of X ¹ to X ³ is N, and at least one of X ⁴ to X ⁸ is N.

In the case of the compound of Formula ad-1, the process temperature may be improved due to the lower molecular weight than derivatives such as pyridine, pyrimidine, and triazine having a diphenyl substituent.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-2.

[Formula ad-2]

In Formula ad-2, X ¹ to X ³ are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and at least one of X ¹ to X ³ is N.

In the case of Chemical Formula ad-2, thermal stability such as glass transition temperature may be improved due to the introduction of biphenyl having excellent thermal stability, and the non-planarity of molecules may be improved due to the introduction of bulky diphenyl substituents to intermolecular interactions. The action can be suppressed.

The compound for an organic optoelectronic device may be any one of the compounds represented by Formulas A-1 to A-36. However, it is not limited thereto.

[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5] [Formula A-6]

[Formula A-7] [Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11] [Formula A-12]

[Formula A-13] [Formula A-14] [Formula A-15]

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

[Formula A-19] [Formula A-20] [Formula A-21]

[Formula A-22] [Formula A-23] [Formula A-24]

[Formula A-25] [Formula A-26] [Formula A-27]

[Formula A-28] [Formula A-29] [Formula A-30]

[Formula A-31] [Formula A-32] [Formula A-33]

[Formula A-34] [Formula A-35] [Formula A-36]

The compound for an organic optoelectronic device may be any one of the compounds represented by Formulas B-1 to B-96. However, it is not limited thereto.

[Formula B-1] [Formula B-2] [Formula B-3]

[Formula B-4] [Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8] [Formula B-9]

[Formula B-10] [Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14] [Formula B-15]

[Formula B-16] [Formula B-17] [Formula B-18]

Formula B-19 Formula B-20 Formula B-21

[Formula B-22] [Formula B-23] [Formula B-24]

[Formula B-25] [Formula B-26] [Formula B-27]

[Formula B-28] [Formula B-29] [Formula B-30]

[Formula B-31] [Formula B-32] [Formula B-33]

[Formula B-34] [Formula B-35] [Formula B-36]

[Formula B-37] [Formula B-38] [Formula B-39]

[Formula B-40] [Formula B-41] [Formula B-42]

[Formula B-43] [Formula B-44] [Formula B-45]

[Formula B-46] [Formula B-47] [Formula B-48]

[Formula B-49] [Formula B-50] [Formula B-51]

[Formula B-52] [Formula B-53] [Formula B-54]

[Formula B-55] [Formula B-56] [Formula B-57]

[Formula B-58] [Formula B-59] [Formula B-60]

[Formula B-61] [Formula B-62] [Formula B-63] [Formula B-64]

[Formula B-65] [Formula B-66] [Formula B-67] [Formula B-68]

[Formula B-69] [Formula B-70] [Formula B-71] [Formula B-72]

[Formula B-74] [Formula B-74] [Formula B-75] [Formula B-76]

[Formula B-77] [Formula B-78] [Formula B-79] [Formula B-80]

[Formula B-81] [Formula B-82] [Formula B-83] [Formula B-84]

[Formula B-85] [Formula B-86] [Formula B-87] [Formula B-88]

[Formula B-89] [Formula B-90] [Formula B-91] [Formula B-92]

[Formula B-93] [Formula B-94] [Formula B-95] [Formula B-96]

The compound for an organic optoelectronic device may be any one of the compounds represented by Formulas C-1 to C-49. However, it is not limited thereto.

[C-1] [C-2] [C-3]

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

[C-7] [C-8] [C-9]

[C-10] [C-11] [C-12]

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

[C-16] [C-17] [C-18]

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

[C-22] [C-23] [C-24]

[C-25] [C-26] [C-27]

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

[C-31] [C-32] [C-33]

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

[C-37] [C-38] [C-39]

[C-40] [C-41] [C-42]

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

[C-46] [C-47] [C-48]

[C-49]

The compound for an organic optoelectronic device may be represented by the following formula D-1 to D-20. However, it is not limited thereto.

[D-1] [D-2] [D-3]

[D-4] [D-5]

[D-6] [D-7] [D-8]

[D-9] [D-10]

[D-11] [D-12] [D-13]

[D-14] [D-15]

[D-16] [D-17] [D-18]

[D-19] [D-20]

In the case where the compound according to one embodiment of the present invention requires both the electronic property and the hole property, it is effective to improve the lifetime of the organic light emitting device and reduce the driving voltage by introducing the functional group having the electron characteristic.

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 Compound A-9

Compound A-10 was synthesized through the following synthesis reactions.

25.930 g (90.31 mmol) of N-phenylcarbazol-3-yl boronic acid, 29.013 g (108.37 mmol) of 2-chloro-4,6-diphenyl pyrimidine in a 1 L round bottom flask equipped with a nitrogen atmosphere stirrer; After mixing 362 mL of tetrahydrofuran and 90 mL of an aqueous 2M-potassium carbonate solution, 3.131 g (2.71 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, and the mixture was heated to reflux for 12 hours under a nitrogen stream. After completion of the reaction, the organic layer was separated and anhydrous magnesium sulfate was added to remove water. The solution was filtered through a silica gel, and then all solvents were removed and recrystallized with dichloromethane and hexane to obtain 35 g of intermediate 1 (yield 82%).

Dissolve 34.3 g (72.27 mmol) of Intermediate 1 in 362 mL of dimethylformamide in a 1 L round bottom flask and stir. 14.15 g (79.50 mmol) of N-bromosuccinimide is dissolved in 70 mL of dimethylformamide, and then slowly added dropwise into the reactor, followed by stirring for 12 hours. The reaction is poured into 1 liter of water to complete the reaction and the solids are filtered off. The solid was washed with water and methanol, and then recrystallized with dichloromethane and hexane to obtain 30 g of intermediate 2 (yield 75%).

In a 500 mL round bottom flask equipped with a nitrogen atmosphere stirrer, intermediate 2 29.2 g (52.73 mmol), bispinacolatodiborone 20.1 g (79.10 mmol), potassium acetate 10.35 g (105.46 mmol), palladium diphenylphosphinoferrocenedi 2.153 g (2.64 mmol) of chloride are added to 210 mL of toluene and stirred. The temperature of the reactor is raised to 110 degrees and stirred for 12 hours. The reaction was filtered to terminate the reaction, and the filtrate was added to the filtrate and stirred, followed by silica gel filtering. After removing all the solvents, the resultant was regenerated with dichloromethane and hexane to obtain 20 g of intermediate 3 (yield 63%).

In a 500 mL round bottom flask equipped with a nitrogen atmosphere stirrer, 19.530 g (32.52 mmol) of Intermediate 3, 12.1 g (39.03 mmol) of 1-bromo-3,5-diphenyl benzene and 130 mL of tetrahydrofuran and 2M-carboxylic acid After mixing 33 mL of aqueous potassium solution, 1.127 g (0.98 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, and the resulting mixture was heated to reflux for 12 hours under a nitrogen stream. After completion of the reaction, the solids formed by adding methanol to the reactor are filtered out. The solids are washed with water and methanol and then dissolved in chlorobenzene by heating. Put the complex call and stir for 30 minutes, and then silica gel filter. After removing all of the solvent, and recrystallized with chlorobenzene and hexane to give 17 g (74% yield) of Compound A-9.

calcd. C ₅₁ H ₃₄ N ₄ : C, 87.15; H, 4.88; N, 7.97; found: C, 87.21; H, 4.78; N, 7.88

Example  2: Preparation of Compound B-1

Compound B-1 was prepared through the following synthesis method.

[Reaction Scheme 1]

343.4 g (151.15 mmol) of N-phenylcarbazol-3-yl boronic acid, 56.26 g (181.38 mmol) of 2-bromo-4,6-diphenyl pyridine in a 1 L round bottom flask equipped with a nitrogen atmosphere stirrer; After mixing 605 mL of tetrahydrofuran and 152 mL of an aqueous 2M-potassium carbonate solution, 5.240 g (4.53 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, and the mixture was heated and refluxed under a nitrogen stream for 12 hours. After completion of the reaction, the organic layer was separated and anhydrous magnesium sulfate was added to remove water. The solution was filtered and then recrystallized with dichloromethane and hexane to obtain 61 g of intermediate 4 (yield 85%).

[Reaction Scheme 2]

In a 1 L round bottom flask, 61 g (129.52 mmol) of Intermediate 4 was dissolved in 500 mL of dimethylformamide and stirred. 25.36 g (142.38 mmol) of N-bromosuccinimide was slowly added dropwise in 140 mL of dimethylformamide. do. The reactor is stirred for 12 hours and then the reaction solution is poured into water to filter out the solids. The solid was recrystallized with dichloromethane and hexane to obtain 62 g of intermediate 5 (yield 87%).

Scheme 3

In a 500 mL round bottom flask equipped with a nitrogen atmosphere stirrer, 25.75 g (46.7 mmol) of intermediate 5, 16.1 g (56.03 mmol) of N-phenylcarbazol-3-yl boronic acid, 186 mL of tetrahydrofuran and 2M potassium carbonate After mixing 94 mL of aqueous solution, 1.619 g (1.40 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, and the mixture was heated to reflux for 12 hours under a nitrogen stream. The solid formed after the completion of the reaction is filtered and washed with water and methanol. The solid is dissolved in toluene by heating, and then stirred with anhydrous magnesium sulfate and complex call, followed by silica gel filter. After removing all solvents, the mixture was recrystallized with toluene and hexane to obtain Compound B-1 23 g (69% yield).

calcd. C ₅₃ H ₃₅ N ₃ : C, 89.17; H, 4.94; N, 5.89; found: C, 89.12; H, 4.78; N, 5.75

Example  3: Preparation of Compound B-57

Compound B-57 was prepared by the following synthesis method.

[Reaction Scheme 4]

In a 1 L round bottom flask equipped with a nitrogen atmosphere stirrer, intermediate 5 66.031 g (119.74 mmol), bispinacolatodiborone 45.609 g (179.60 mmol), potassium acetate 23.504 g (239.47 mmol), palladium diphenylphosphinoferrocenedi 4.889 g (5.99 mmol) of chloride are added to 478 mL of toluene and stirred. The temperature of the reactor is raised to 110 degrees and stirred for 12 hours. The reaction was filtered to terminate the reaction, and the filtrate was added to the filtrate and stirred, followed by silica gel filtering. After removing all the solvents, the resultant was regenerated with dichloromethane and hexane to obtain 61.70 g of intermediate 6 (yield 86%).

Scheme 5

In a 500 mL round bottom flask with a nitrogen atmosphere stirrer, intermediate 6 20.072 g (33.54 mmol), N- (4,6-diphenyl) triazinyl-3-bromocarbazole 13.340 g (27.95 mmol) and tetrahydrofuran After 112 mL and 28 mL of 2M aqueous potassium carbonate solution were mixed, 0.969 g (0.84 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, followed by heating to reflux for 12 hours under a nitrogen stream. After completion of the reaction, the reactant was poured into methanol, the solids were filtered off and washed with water and methanol. The solid was dissolved in chlorobenzene by heating, and stirred with anhydrous magnesium sulfate and complex call, followed by silica gel filter. After removing all the solvents and recrystallized with chlorobenzene to give 17 g (70% yield) of Compound B-57.

calcd. C ₆₂ H ₄₀ N ₆ : C, 85.69; H, 4.64; N, 9.67; found: C, 85.54; H, 4.55; N, 9.78

Example  4: Preparation of Compound C-1

Compound C-1 was prepared in the following manner.

[Reaction Scheme 6]

23.511 g (52.79 mmol) of N-phenyl- (6-phenyl) carbazol-3-yl-boronic acid ester in a 500 mL round bottom flask equipped with a nitrogen atmosphere stirrer, 6-bromo-2- (4-pyri) Dil) pyridine 14.892 g (63.35 mmol) and 211 mL of tetrahydrofuran and 105 mL of 2M-potassium carbonate aqueous solution were mixed, and then 1.83 g (1.58 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto. Heated to reflux for hours. After completion of the reaction, the reaction product was separated from the organic layer and the solvent was removed, and then purified by column chromatography using ethyl acetate as a solvent to obtain compound C-1 13 g (52% yield).

calcd. C ₃₄ H ₂₃ N ₃ : C, 86.23; H, 4.90; N, 8.87; found: C, 86.34; H, 4.85; N, 8.79

Example  5: Preparation of Compound D-4

Compound D-4 was prepared in the following manner.

[Reaction Scheme 7]

54.016 g (121.29 mmol) of N- (4-biphenyl) carbazol-3-yl-boronic acid ester, 2-chloro-4,6-diphenylpyrimidine in a 1 L round bottom flask equipped with a stirrer in a nitrogen atmosphere 38.820 g (145.54 mmol) and 300 mL of tetrahydrofuran were mixed with 120 mL of 2M aqueous potassium carbonate solution, and 4.2 g (3.64 mmol) of tetrakistriphenylphosphinepalladium (0) was added thereto, followed by heating under nitrogen stream for 12 hours. It was refluxed. After completion of the reaction, the reactant was poured into methanol, the solids were filtered off and washed with water and methanol. The solids are dissolved by heating toluene, followed by a silica gel filter and removal of all solvents. Recrystallization with dichlorobenzene afforded 50.6 g (76% yield) of compound D4.

calcd. C ₄₀ H ₂₇ N ₃ : C, 87.40; H, 4.95; N, 7.64; found: C, 87.30; H, 4.75; N, 7.54

(Production of organic light emitting device)

Example  6: Organic photoelectric device  Produce

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor. Using the prepared ITO transparent electrode as an anode, HTM (see material structure below) was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 1200 Å.

[HTM]

The material synthesized in Example 1 was used as a host on the hole transport layer, and PhGD (see the following figure) was doped with phosphorescent green dopant to form a light emitting layer having a thickness of 300 Å by vacuum deposition.

[PhGD]

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 sequentially depositing LiF 5 ′ and Al 1000 ′ on the electron transport layer to form a cathode.

[BAlq] [Alq3]

Example  7

An organic light emitting diode was manufactured according to the same method as Example 6 except for using Example 2 (B-1) instead of Example 1.

Example  8

An organic light emitting diode was manufactured according to the same method as Example 6 except for using Example 3 (B-57) instead of Example 1.

Comparative example  One

An organic light emitting diode was manufactured according to the same method as Example 6 except for using CBP instead of Example 1.

(Performance Measurement of Organic Light Emitting Device)

For each of the organic light emitting diodes manufactured in Examples 6 to 8, current density change, luminance change, and luminous efficiency according to voltage were measured. Specific measurement methods are as follows, and 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-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

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

Host Measurement result at 9000 cd / m2 Driving voltage
(V) Luminous efficiency
(cd / A) Power efficiency
(lm / W) Color coordinates Example 6 6.5 43.3 20.9 0.34, 0.62 Example 7 6.5 44.5 21.5 0.34, 0.62 Example 8 6.5 46.3 22.4 0.34, 0.62 Comparative Example 1 8.5 45.4 16.5 0.33, 0.62

As can be seen in Table 1, the light emission characteristics of the hosts manufactured in Examples 6 to 8 are lower in driving voltage and higher in power efficiency than CBP of Comparative Example 1.

It is believed that this resulted in improved driving voltage, power efficiency, and the like compared to CBP by improving the injection and transfer characteristics of the holes and electrons of the compound due to the introduction of appropriate substituents.

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 (21)

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

In Chemical Formula 1,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group,
R ¹ and R ² are independently 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, or a combination thereof,
L is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof;
n is 0 or 3,
Ar ³ is hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula (2):
(2)

In Formula 2,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group,
R ¹ and R ² are independently 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, or a combination thereof,
L is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof;
n is 0 or 3,
Ar ³ is hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The method of claim 1,
Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted It is a dibenzofuranyl group or a combination thereof The compound for an organic optoelectronic device.
The method of claim 1,
Ar ³ is hydrogen compound for an organic optoelectronic device.
The method of claim 1,
Ar ² is a compound for an organic optoelectronic device is selected from any one of the following formulas S-1 to S-5:
[Formula S-1] [Formula S-2]

[Formula S-3] [Formula S-4]

Formula S-5

In S-1 and S-2,
* Indicates the bonding position,
In Chemical Formulas S-3 to S-5,
R ¹ to R ⁴ are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group or a combination thereof,
In Chemical Formulas S-3 and S-4,
Any one of R ¹ to R ⁴ represents a bonding position,
In Chemical Formula S-5,
Any one of R ¹ to R ³ represents a binding position.
The method of claim 1,
Ar ³ is a compound for an organic optoelectronic device is selected from any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted triphenyl group.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula (3):
(3)

In Formula 3,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group,
R ¹ to R ⁵ are independently 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, or a combination thereof,
L is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof;
n is 0 or 3,
X is -NR'-, -S- or -O-, wherein R 'is 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 or a combination thereof.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula (4):
[Chemical Formula 4]

In Formula 4,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group,
R ¹ to R ⁵ are independently 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, or a combination thereof,
L is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof;
n is 0 or 3,
Ar ⁴ is 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, or a combination thereof.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula (5):
[Chemical Formula 5]

In Formula 5,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Ar ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group,
R ¹ to R ⁵ are independently 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, or a combination thereof,
L is 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, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof;
n is 0 or 3,
Ar ⁴ is 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, or a combination thereof.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula ad-1:
[Formula ad-1]

In the above formula ad-1,
X ¹ to X ⁸ are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted Ring C2 to C30 heteroaryl group or a combination thereof,
At least one of X ¹ to X ³ is N,
At least one of X ⁴ to X ⁸ is N.
The method of claim 1,
Compound for an organic optoelectronic device represented by Formula 1 is a compound for an organic optoelectronic device represented by the following formula ad-2:
[Formula ad-2]

In the above formula ad-2,
X ¹ to X ³ are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted Ring C2 to C30 heteroaryl group or a combination thereof,
At least one of X ¹ to X ³ is N.
The method of claim 1,
The compound for an organic optoelectronic device is any one of the compounds represented by the formula A-1 to A-36.
[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5] [Formula A-6]

[Formula A-7] [Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11] [Formula A-12]

[Formula A-13] [Formula A-14] [Formula A-15]

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

[Formula A-19] [Formula A-20] [Formula A-21]

[Formula A-22] [Formula A-23] [Formula A-24]

[Formula A-25] [Formula A-26] [Formula A-27]

[Formula A-28] [Formula A-29] [Formula A-30]

[Formula A-31] [Formula A-32] [Formula A-33]

[Formula A-34] [Formula A-35] [Formula A-36]

The method of claim 1,
The compound for an organic optoelectronic device is any one of the compounds represented by formulas B-1 to B-96.
[Formula B-1] [Formula B-2] [Formula B-3]

[Formula B-4] [Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8] [Formula B-9]

[Formula B-10] [Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14] [Formula B-15]

[Formula B-16] [Formula B-17] [Formula B-18]

Formula B-19 Formula B-20 Formula B-21

[Formula B-22] [Formula B-23] [Formula B-24]

[Formula B-25] [Formula B-26] [Formula B-27]

[Formula B-28] [Formula B-29] [Formula B-30]

[Formula B-31] [Formula B-32] [Formula B-33]

[Formula B-34] [Formula B-35] [Formula B-36]

[Formula B-37] [Formula B-38] [Formula B-39]

[Formula B-40] [Formula B-41] [Formula B-42]

[Formula B-43] [Formula B-44] [Formula B-45]

[Formula B-46] [Formula B-47] [Formula B-48]

[Formula B-49] [Formula B-50] [Formula B-51]

[Formula B-52] [Formula B-53] [Formula B-54]

[Formula B-55] [Formula B-56] [Formula B-57]

[Formula B-58] [Formula B-59] [Formula B-60]

[Formula B-61] [Formula B-62] [Formula B-63] [Formula B-64]

[Formula B-65] [Formula B-66] [Formula B-67] [Formula B-68]

[Formula B-69] [Formula B-70] [Formula B-71] [Formula B-72]

[Formula B-74] [Formula B-74] [Formula B-75] [Formula B-76]

[Formula B-77] [Formula B-78] [Formula B-79] [Formula B-80]

[Formula B-81] [Formula B-82] [Formula B-83] [Formula B-84]

[Formula B-85] [Formula B-86] [Formula B-87] [Formula B-88]

[Formula B-89] [Formula B-90] [Formula B-91] [Formula B-92]

[Formula B-93] [Formula B-94] [Formula B-95] [Formula B-96]

The method of claim 1,
The compound for an organic optoelectronic device is any one of the compounds represented by the formula C-1 to C-49.
[C-1] [C-2] [C-3]

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

[C-7] [C-8] [C-9]

[C-10] [C-11] [C-12]

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

[C-16] [C-17] [C-18]

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

[C-22] [C-23] [C-24]

[C-25] [C-26] [C-27]

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

[C-31] [C-32] [C-33]

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

[C-37] [C-38] [C-39]

[C-40] [C-41] [C-42]

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

[C-46] [C-47] [C-48]

[C-49]

The method of claim 1,
The compound for an organic optoelectronic device is any one of the compounds represented by the formulas D-1 to D-20.
[D-1] [D-2] [D-3]

[D-4] [D-5]

[D-6] [D-7] [D-8]

[D-9] [D-10]

[D-11] [D-12] [D-13]

[D-14] [D-15]

[D-16] [D-17] [D-18]

[D-19] [D-20]

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.
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.
18. The method of claim 17,
Wherein the organic thin film layer is 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.
19. The method of claim 18,
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.
19. The method of claim 18,
Wherein the compound for an organic optoelectronic device is contained in a light emitting layer.
A display device comprising the organic light emitting device of claim 17.

Images