WO2013100540A1 - Compound for organic optoelectronic device, organic light emitting device containing same, and display device containing said organic light emitting device - Google Patents

Description

Compound for an organic optoelectronic device, an organic light emitting device comprising the same and a display device comprising the organic light emitting device

The present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent life, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the organic light emitting device.

An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.

Organic optoelectronic devices can be divided into two types according to the operation principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.

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

Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.

In particular, organic light emitting diodes (OLEDs) are attracting attention as the demand for flat panel displays increases. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.

Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, 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 excitons formed are moved to the ground state, and light having a specific wavelength is generated.

Recently, it has been known that not only fluorescent light emitting materials but also phosphorescent light emitting materials can be used as light emitting materials of organic light emitting devices, and these phosphorescent light emitting electrons transition from the ground state to the excited state, It is composed of a mechanism in which singlet excitons are non-luminescent transition into triplet excitons through intersystem crossing, and then triplet excitons emit light as they transition to the ground state.

As described above, the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.

In addition, the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase luminous efficiency and stability through the host / dopant system can be used as a light emitting material.

In order for the organic light emitting device to fully exhibit the above-described excellent features, materials constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc. Supported by this stable and efficient material should be preceded, and development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, development of new materials is continuously required. The necessity of such a material development is the same in the other organic optoelectronic devices described above.

In addition, the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has low initial investment cost. Large area has an advantage.

Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range. In particular, compared to conventional LCD (liquid crystal display) as a self-luminous type, even in a dark place or outside light is good cyanity, and no backlight is required, it can reduce the thickness and weight to 1/3 of the LCD.

In addition, the response speed is 1000 times faster than the LCD in microseconds, it is possible to implement a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era. Based on these advantages, we have made rapid technological developments with efficiency of 80 times and lifespan over 100 times since the first development in the late 1980s. Increasingly, large-scaled developments are being made with the introduction of organic light emitting diode panels.

In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer. However, since the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.

In addition, in order to improve the life, it is necessary to prevent the material from crystallizing due to Joule heat generated when the device is driven. Therefore, there is a need for development of organic compounds having excellent electron injection and mobility and high electrochemical stability.

Provided are a compound for an organic optoelectronic device, which can play a role of hole injection and transport or electron injection and transport, and can act as a light emitting host with an appropriate dopant.

An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.

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

[Formula 1]

In Formula 1, L is any one of the following Formulas 2 to 4, L ² and L ³ are independently a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynyl Ethylene group, substituted or unsubstituted C6 to C30 arylene group or substituted or unsubstituted C2 to C30 heteroarylene group, Ar ² and Ar ³ is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted A C6 to C36 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties , n2 and n3 are any integers from 0 to 3, m2 and m3 are 1:

[Formula 2] [Formula 3] [Formula 4]

In Formulas 2 to 4, * at each terminal represents a linking position with L ² and L ³ in Formula 1, and 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 or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to A C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n1 is an integer of any one of 0 to 3, and Ar ¹ is hydrogen, deuterium, substituted or Unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or unsubstituted arylamine group or substituted or ratio And hwandoen hetero arylamine group, m1 is 0 or 1.

The compound for an organic optoelectronic device may be represented by the following formula (5).

[Formula 5]

In Formula 5, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

The compound for an organic optoelectronic device may be represented by the following formula (6).

[Formula 6]

In Formula 6, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

The compound for an organic optoelectronic device may be represented by the following formula (7).

[Formula 7]

In Formula 7, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

M1 and n1 may be 0.

Ar ² and Ar ³ may be a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties.

Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties is substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted carba Zolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted thiazazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted Benzotriazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group , Substituted or unsubstituted purinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted naphpyri Dinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted phenazinyl group or theirs May be a combination.

The substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be represented by any one of the following Chemical Formulas 8 to 12.

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12]

The compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-48.

[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-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]

[Formula A-37] [Formula A-38] [Formula A-39]

[Formula A-40] [Formula A-41] [Formula A-42]

 [Formula A-43] [Formula A-44] [Formula A-45]

[Formula A-46] [Formula A-47] [Formula A-48]

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-48.

[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]

The compound for an organic optoelectronic device may be represented by any one of Formulas C-1 to C-48.

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

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

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

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

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

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

Formula C-19 Formula C-20 Formula C-21

Formula C-22 Formula C-23 Formula C-24

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

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

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

Formula C-34 Formula C-35 Formula C-36

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

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

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

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

The compound for an organic optoelectronic device may be a triplet excitation energy (T1) 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 photosensitive 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 transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination 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 a light emitting layer.

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

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

Compounds having high hole or electron transport properties, film stability thermal stability and high triplet excitation energy can be provided.

Such a compound can be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer. The organic optoelectronic device using the same has excellent electrochemical and thermal stability, and has excellent life characteristics, and may have 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 may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.

100 organic light emitting device 110 cathode

120: anode 105: organic thin film layer

130: light emitting layer 140: hole transport layer

150: electron transport layer 160: electron injection layer

170: hole injection layer 230: light emitting layer + electron transport layer

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

As used herein, unless otherwise defined, “substituted” means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C1 to C10 such as C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc. Mean substituted by 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 of C1 to C10 trifluoroalkyl group or cyano group such as C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group and trifluoromethyl group may be fused to form a ring. .

As used herein, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon.

In the present specification, "combination thereof" means that two or more substituents are bonded to a linking group or two or more substituents are condensed to each other unless otherwise defined.

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.

"Alkenylene group" means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond, and "alkynylene group" means at least two carbon atoms of at least one carbon-carbon triplet. It means a functional group consisting of a bond. The alkyl group, whether saturated or unsaturated, may be branched, straight chain or cyclic.

The alkyl group may be an alkyl group that is 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 functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.

An "aryl group" includes a monocyclic or fused ring polycyclic (ie, a ring that divides adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means containing 1 to 3 hetero atoms selected from the group consisting of N, O, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

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 instead of nitrogen. Specific examples thereof include dibenzofuran (dibenzofuranyl group) and dibenzothiophene (dibenzothiophenyl group).

In the present specification, the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate the injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.

In addition, an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer.

Compound for an organic optoelectronic device according to an embodiment of the present invention includes a core comprising a carbazolyl group and at least one phenylenyl group bonded to the carbazolyl group and a substituent having at least one electronic property bonded to the phenylenyl group. can do.

The substituent having at least one electronic property bonded to the phenylenyl group may be a meta position.

When the substituent is a meta position, the conjugation from the core including the carbazolyl group and the at least one phenylene group bonded to the carbazolyl group to the substituent having electronic properties is broken at the metasubstituent position.

This reduces the band gap between the HOMO level and LUMO level, which occurs when conjugation is connected to the para-position, thereby preventing red light shifting of the compound's emission wavelength. have.

In addition, when the substituent is linked to the meta position from the core, the solubility of the compound is relatively improved as compared to the case connected to the para position, which has the advantage of facilitating material synthesis.

In addition, the carbazolyl group of the core may optionally include a substituent having hole characteristics. In this case, the HOMO and LUMO levels of the entire compound can be appropriately adjusted as necessary, thereby preparing a compound for an organic optoelectronic device having various energy levels.

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 because it includes a substituent having an electronic property of carbazolyl group having excellent hole properties. In particular, it may be suitable for the light emitting material.

In addition, since the substituent having at least one electronic property bonded to the phenyl group of the core may be a meta position, the symmetry in the entire molecule may be reduced, and thus the crystallinity of the compound may be lowered, and thus recrystallization is suppressed in the device.

At least one of the substituents bonded to the core may be a substituent having electronic properties. Therefore, the compound may satisfy the conditions required in the light emitting layer by reinforcing the electronic properties in the carbazole structure having excellent hole properties. 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 band gaps by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.

By using a compound having an appropriate energy level in the organic optoelectronic device according to the substituent of the compound, the hole transport ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in organic chemical and thermal stability It is possible to improve the life characteristics when driving the device.

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

[Formula 1]

In Formula 1, L is any one of the following Formulas 2 to 4, L ² and L ³ are independently a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynyl Ethylene group, substituted or unsubstituted C6 to C30 arylene group or substituted or unsubstituted C2 to C30 heteroarylene group, Ar ² and Ar ³ is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted A C6 to C36 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties , n2 and n3 are any integers from 0 to 3, m2 and m3 are 1:

[Formula 2] [Formula 3] [Formula 4]

In Formulas 2 to 4, * at each terminal represents a linking position with L ² and L ³ in Formula 1, and 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 or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to A C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, n1 is an integer of any one of 0 to 3, and Ar ¹ is hydrogen, deuterium, substituted or Unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or unsubstituted arylamine group or substituted or ratio And hwandoen hetero arylamine group, m1 is 0 or 1.

The compound for an organic optoelectronic device may be a substituted or unsubstituted C2 to C30 heteroaryl group having at least one of Ar ² and Ar ³ , and the compound for an organic optoelectronic device may emit light, holes or Electronic properties; Membrane stability; Thermal stability and high triplet excitation energy (T1).

The two substituents bonded to the phenylenyl group present in Formulas 2 to 4 may be a meta position. When a substituent exists in the meta position, a structure having an asymmetric bipolar characteristic can be manufactured, and the structure of the asymmetric bipolar characteristic can be expected to improve light emitting efficiency and performance of the device by improving hole and electron transfer capability.

In addition, the structure of the compound can be prepared in bulk by the control of the substituent, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be longer.

The compound for an organic optoelectronic device may be represented by Formula 5 more specifically.

[Formula 5]

In Formula 5, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

The compound for an organic optoelectronic device may be represented by Formula 6 more specifically.

[Formula 6]

In Formula 6, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

The compound for an organic optoelectronic device may be represented by the following formula (7).

[Formula 7]

In Formula 7, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substitution having electronic properties Or an unsubstituted C2 to C30 heteroaryl group, at least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and n2 and n3 are any of integers from 0 to 3 One, m2 and m3 are 1, R ¹ and R ² are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group L ¹ represents 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 A C30 heteroarylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group having hole characteristics, and m1 is 0 or 1.

By selectively adjusting the L ¹ to L ^{3 it} is possible to determine the conjugation length of the entire compound, from which it is possible to adjust the HOMO-LUMO bandgap. Through this, it is possible to develop a compound having an appropriate bandgap and wavelength applicable to each of blue, green, and red.

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 and the like.

M1 and n1 may be 0.

Ar ² and Ar ³ may be a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties is substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted Substituted carbazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted cythiazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted A substituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrida Genyl group, substituted or unsubstituted purinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted Substituted naphpyridinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted acridinyl groups, substituted or unsubstituted phenanthrolinyl groups, substituted or unsubstituted phenazinyl groups Or combinations thereof, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties may be a substituent represented by any one of the following Formulas 8 to 12.

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12]

Ar ¹ is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substituted or unsubstituted C2 to C30 heteroaryl group having a hole property, a substitution Or an unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.

More specifically, the substituted or unsubstituted C6 to C30 aryl group having the above hole properties is substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted anthracenyl group , Substituted or unsubstituted fluorenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted spiro-fluorenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or It may be an unsubstituted perenyl group or a combination thereof.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics is substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted Ring indol carbazolyl group;

The aryl group or heteroaryl group which is a substituent bonded to the nitrogen of the substituted or unsubstituted arylamine group and substituted or unsubstituted heteroarylamine group is more specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group , Substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perrylenyl group, substituted or unsubstituted indenyl group , Substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted Is an unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted Substituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted Or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted Quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted Hwandoen phenazine group, may be substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxazine group, or a combination thereof.

The compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-48.

[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-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]

[Formula A-37] [Formula A-38] [Formula A-39]

[Formula A-40] [Formula A-41] [Formula A-42]

[Formula A-43] [Formula A-44] [Formula A-45]

[Formula A-46] [Formula A-47] [Formula A-48]

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-48.

[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]

The compound for an organic optoelectronic device may be represented by any one of Formulas C-1 to C-48.

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

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

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

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

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

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

Formula C-19 Formula C-20 Formula C-21

Formula C-22 Formula C-23 Formula C-24

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

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

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

Formula C-34 Formula C-35 Formula C-36

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

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

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

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

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

Compound for an organic optoelectronic device according to an embodiment of the present invention described above has a maximum emission wavelength of about 320 to 500 nm, triplet excitation energy (T1) is 2.0 eV or more, more specifically 2.0 to 4.0 eV range The charge of the host having a high triplet excitation energy is well transferred to the dopant, thereby increasing the light emitting efficiency of the dopant and lowering the driving voltage by freely adjusting the HOMO and LUMO energy levels of the material. Because of the advantages it can be very useful as a host material or a charge transport material.

In addition, since the compound for an organic optoelectronic device has photoactive and electrical activity, nonlinear optical material, electrode material, color change material, optical switch, sensor, module, wave guide, organic transistor, laser, light absorber, dielectric and separator It can also be very usefully applied to materials such as (membrane).

The compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 90 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.

The compound for an organic optoelectronic device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport 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 comprising the compound for an organic optoelectronic device. In this case, the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like. In particular, in the case of an organic solar cell, a 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, and in the case of an organic transistor, a gate, a source-drain electrode, or the like may be used as an electrode material. Can be used.

Hereinafter, an organic light emitting diode will be described in detail.

Another embodiment of the present invention is 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 any one of the organic thin film layer is an embodiment of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to.

The organic thin film layer which 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 transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. At least one of the layers includes the compound for an organic optoelectronic device according to the present invention. In particular, the hole transport layer or the hole injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention. In addition, when the compound for an organic optoelectronic device is included in a light emitting layer, the compound for an 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 cross-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, the organic light emitting diodes 100, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.

The anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected 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 negative electrode 110 includes a negative electrode material, and the negative electrode 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, or alloys thereof, and LiF / Al. , Multilayer structure materials such as LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, and the like, but are not limited thereto. Preferably, a metal electrode such as aluminum may be used as the cathode.

First, referring to FIG. 1, FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105. The organic thin film layer 105 may exist only as a light emitting layer 130.

Referring to FIG. 2, FIG. 2 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 and an hole transport layer 140 including an electron transport layer as the organic thin film layer 105, as shown in FIG. 2. Likewise, the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport 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 bonding and hole transporting properties with a transparent electrode such as ITO.

Referring to FIG. 3, FIG. 3 is a three-layered organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, and the organic thin film layer 105. The light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.

Referring to FIG. 4, FIG. 4 illustrates a four-layered organic light emitting diode 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105. As a result, the hole injection layer 170 may improve adhesion to ITO used as an anode.

Referring to FIG. 5, FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105. The five-layer organic light emitting device 500 having five layers is present, and the organic light emitting device 500 is effective in lowering the voltage by separately forming the electron injection layer 160.

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, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic optoelectronic device. In this case, the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and the hole blocking layer (not shown) is included in the electron transport layer. It is desirable to provide an organic light emitting device having a simplified structure because it does not need to be formed separately.

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

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

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

The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

Preparation of Compound for Organic Optoelectronic Devices

Example 1: Preparation of Compound A-6

Scheme 1

First Step: Synthesis of Compound (A)

77.49 g (314.88 mmol) of 3-bromocarbazole, 100.78 g (377.86 mmol) of 2-chloro-4,6-dibiphenyl-pyrimidine, 18.89 g of NaH in a 2000 mL round flask in 1200 ml of dimethylformamide at room temperature Stir for 8 hours. After stirring the reaction solution in 2500ml of water, the precipitated solid was washed with methanol and filtered under reduced pressure. The solid was dissolved in chlorobenzene and separated by silica gel to give 135 g (90% yield) of the intermediate compound (A).

[M + H] ⁺ molecular weight 476.37 of A synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Compound (B)

39.93 g (83.8 mmol) of the compound represented by Compound (A), 31.93 g (125.7 mmol) of tetramethyldioxaborolane, 2.7 g (3.35 mmol) of palladium diphenylpyridinoferrocenedichloride, and 24.68 g (251.5 mmol) of potassium acetate Was stirred in 400 ml of dimethylsulfoxide by heating at 110 degrees for 8 hours. The reaction solution was slowly added dropwise to 2000 ml of water to solidify, and this was filtered to give a fleshy solid. The solid was dissolved in 500 ml of dichloromethane, water was removed with anhydrous magnesium sulfate, and then filtered to obtain an organic solution layer. After removing an appropriate amount of the organic solvent, it was dissolved in toluene again and separated by silica gel. The appropriate amount of the solvent was removed and recrystallized in MeOH to give 32 g (73% yield) of the intermediate compound (B).

[M + H] ⁺ molecular weight 523.43 of A1 synthesized by LC-Mass was confirmed.

Third Step: Synthesis of Chemical Formula A-6

22.0 g (56.7 mmol) of 2- (3-bromophenyl) -4,6-difetyltriazine, 32.6 g (62.4 mmol) of the compound represented by compound (B) and tetrakistriphenylphosphinopalladium 3.3 ( 2.8 mmol) was suspended in 250 ml of 2M aqueous potassium carbonate solution and 300 ml of tetrahydrofuran, and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 1000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 25g of compound A-6 (yield 63%).

[M + H] ⁺ molecular weight 704.82 of A1 synthesized by LC-Mass was confirmed.

Example 2: Preparation of Formula A-9

Scheme 2

First Step: Synthesis of Compound (C)

In a 1000 mL round flask, 43.6 g (135.5 mmol) of 3-bromo-6-phenylcarbazole, 43.53 g (162.6 mmol) of 2-chloro-4,6-dibiphenyl-triazine, 8.1 g of NaH in dimethylform 600 ml of amide was stirred for 8 hours at room temperature. The reaction solution was poured into 1200 ml of water, stirred, and the precipitated solid was washed with methanol and filtered under reduced pressure. The solid was dissolved in chlorobenzene and separated with silica gel to give 70 g (yield 93%) of the intermediate compound (C).

[M + H] ⁺ molecular weight 553.45 of A synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Compound (D)

38.3 g (69.3 mmol) of the compound represented by compound (C), 26.4 g (104.4 mmol) of tetramethyldioxaborolane, 2.3 g (2.8 mmol) of palladium diphenylpyridinoferrocenedichloride, and 20.4 g (251.5 mmol) of potassium acetate Was stirred in 400 ml of dimethylsulfoxide by heating at 110 degrees for 8 hours. The reaction solution was slowly added dropwise to 2000 ml of water to solidify, and this was filtered to give a fleshy solid. The solid was dissolved in 500 ml of dichloromethane, water was removed with anhydrous magnesium sulfate, and then filtered to obtain an organic solution layer. After removing an appropriate amount of the organic solvent, it was dissolved in toluene again and separated by silica gel. An appropriate amount of the solvent was removed and recrystallized in MeOH to give 29 g (70% yield) of the intermediate compound (B).

[M + H] ⁺ molecular weight 599.53 of A1 synthesized by LC-Mass was confirmed.

Third Step: Synthesis of Chemical Formula A-9

19.8 g (51.1 mmol) of 2- (3-bromophenyl) -4,6-difetyltriazine, 33.7 g (56.2 mmol) of the compound represented by Compound (D), and 2.95 ((0095) tetrakistriphenylphosphinopalladium 2.6 mmol) was suspended in 250 ml of 2M aqueous potassium carbonate solution and 300 ml of tetrahydrofuran, and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 1000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 27 g (68% yield) of Compound A-6.

[M + H] ⁺ molecular weight 781.90 of A1 synthesized by LC-Mass was confirmed.

Example 3: Preparation of Formula B-18

Scheme 3

First step: synthesis of formula (E)

31.1 g (95.7 mmol) of 3,6-dibromocarbazole, 38.8 g (105.3 mmol) of N-phenylcarbazole-3-tetramethylpinacol ester and 5.53 (4.8 mmol) of tetrakistriphenylphosphinopalladium were dissolved in 2M carbonate. It was suspended in 400 ml of aqueous potassium solution and 550 ml of tetrahydrofuran and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removal of an appropriate amount of the organic solvent, recrystallized in MeOH to give 27 g (58% yield) of Compound (E).

[M + H] ⁺ molecular weight 487.39 of A1 synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Compound (F)

Compound 26.24 g (53.8 mmol) represented by compound (E), 20.5 g (80.7 mmol) of tetramethyldioxaborolane, 1.8 g (2.15 mmol) of palladium diphenylpyridinoferrocenedichloride, and 15.8 g (161.5 mmol) of potassium acetate Was stirred by heating to 300 ml of dimethyl sulfoxide at 110 degrees for 8 hours. The reaction solution was slowly added dropwise to 2000 ml of water to solidify, and this was filtered to give a fleshy solid. The solid was dissolved in 500 ml of dichloromethane, water was removed with anhydrous magnesium sulfate, and then filtered to obtain an organic solution layer. After removing an appropriate amount of the organic solvent, it was dissolved in toluene again and separated by silica gel. An appropriate amount of the solvent was removed and recrystallized in MeOH to give 22 g (76% yield) of the intermediate compound (F).

[M + H] ⁺ molecular weight 534.45 of A1 synthesized by LC-Mass was confirmed.

Third Step: Synthesis of Formula (G)

21.4 g (80.24 mmol) of 2-chloro-4,6-diphenyltriazine, 38.9 g (72.9 mmol) of Compound (F) and 4.21 (3.65 mmol) of tetrakistriphenylphosphinopalladium were mixed with 300 ml of 2M aqueous potassium carbonate solution. It was suspended in 400 ml of tetrahydrofuran and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After an appropriate amount of the organic solvent was removed, it was recrystallized in MeOH to give 32 g (69% yield) of compound (G).

[M + H] ⁺ molecular weight 639.75 of A1 synthesized by LC-Mass was confirmed.

Fourth Step: Synthesis of Chemical Formula B-18

16.37 g (42.28) of compound 29.7 g (46.5 mmol), 2- (3-bromophenyl) -4,6-difetypyrimidine represented by compound (G) in a 1000 mL round bottom flask with a nitrogen atmosphere stirrer. mmol) and 8.12 g (84.5 mmol) of sodium tert-butoxy were dissolved in 500 ml of toluene, and then 1.93 g (2.11 mmol) of palladium dibenzylideneacetone and 1.8 ml of tertiary butyl were added dropwise. The reaction solution was heated and stirred at 110 degrees under a stream of nitrogen for 12 hours. After completion of the reaction, the reaction product was poured with methanol to filter the solids. The solids were dissolved in chlorobenzene again, and activated carbon and anhydrous magnesium sulfate were added to the mixture. The solution was filtered and then recrystallized with chlorobenzene and methanol to give 26 g (yield 65%) of compound B-18.

[M + H] ⁺ molecular weight 946.11 of A1 synthesized by LC-Mass was confirmed.

Example 4: Preparation of Formula B-45

Scheme 4

First step: synthesis of formula (H)

52.2 g (163.8 mmol), 3,6-dibromocarbazole, 2- [4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -phenyl] 66.7 g (180.1 mmol) of dibenzofuran and 9.46 (8.2 mmol) of tetrakistriphenylphosphinopalladium were suspended in 300 ml of a 2M aqueous potassium carbonate solution and 500 ml of tetrahydrofuran, and heated to reflux for 12 hours under a nitrogen stream. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 58 g of compound (E) (yield 73%).

[M + H] ⁺ molecular weight 488.37 of A1 synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Compound (I)

52.5 g (107.5 mmol) of the compound represented by compound (H), 40.9 g (161.2 mmol) of tetramethyldioxaborolane, 3.5 g (4.3 mmol) of palladium diphenylpyridinoferrocenedichloride, and 31.6 g (322.4 mmol) of potassium acetate Was heated to 540 ml of dimethylsulfoxide at 110 degrees for 8 hours and stirred. The reaction solution was slowly added dropwise to 2000 ml of water to solidify, and this was filtered to give a fleshy solid. The solid was dissolved in 500 ml of dichloromethane, water was removed with anhydrous magnesium sulfate, and then filtered to obtain an organic solution layer. After removing an appropriate amount of the organic solvent, it was dissolved in toluene again and separated by silica gel. An appropriate amount of the solvent was removed and recrystallized in MeOH to give 42 g of intermediate compound (I) (yield 73%).

[M + H] ⁺ molecular weight 535.44 of A1 synthesized by LC-Mass was confirmed.

Third step: synthesis of formula (J)

21.4 g (80.1 mmol) of 2-chloro-4,6-diphenyltriazine, 38.9 g (72.8 mmol) of Compound (I) and 4.21 (3.65 mmol) of tetrakistriphenylphosphinopalladium were mixed with 300 ml of 2M aqueous potassium carbonate solution. It was suspended in 400 ml of tetrahydrofuran and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After an appropriate amount of the organic solvent was removed, it was recrystallized in MeOH to give 32 g (69% yield) of compound (G).

[M + H] ⁺ molecular weight 640.73 of A1 synthesized by LC-Mass was confirmed.

Fourth Step: Synthesis of Chemical Formula B-45

17.5 g (45.2) of compound 31.86 g (49.7 mmol), 2- (3-bromophenyl) -4,6-difetypyrimidine, represented by compound (G) in a 1000 mL round bottom flask equipped with a nitrogen atmosphere stirrer mmol) and 8.68 g (90.4 mmol) of sodium tert-butoxy were dissolved in 500 ml of toluene, followed by dropwise addition of 2.07 g (2.26 mmol) of palladium dibenzylideneacetone and 1.9 ml of tertiary butyl. The reaction solution was heated and stirred at 110 degrees under a stream of nitrogen for 12 hours. After completion of the reaction, the reaction mixture was poured into methanol, and the solid was filtered. Then, the solid was dissolved in chlorobenzene, and then activated carbon and anhydrous magnesium sulfate were stirred. The solution was filtered and then recrystallized with chlorobenzene and methanol to obtain 29 g (68% yield) of compound B-18.

[M + H] ⁺ molecular weight 948.08 of A1 synthesized by LC-Mass was confirmed.

Example 5: Preparation of Formula C-24

Scheme 5

First step: synthesis of formula (K)

46.7 g (145.2 mmol) of 3-bromo-6-phenylcarbazole, 2,4-diphenyl-6- [3- (4,4,5,5-tetramethyl- [1,3,2] dioxabo 69.5 g (159.8 mmol) of rolan-2-yl) -phenyl]-[1,3,5] -triazine and 8.4 (7.26 mmol) of tetrakistriphenylphosphinopalladium were added with 300 ml of 2M aqueous potassium carbonate solution and tetrahydrofuran. It was suspended in 400 ml and heated to reflux for 12 hours under a stream of nitrogen. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 58 g (73% yield) of Compound (K).

[M + H] ⁺ molecular weight 550.65 of A1 synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Chemical Formula C-24

36.74 g (66.68 mmol) of compound represented by compound (K), 28.40 g of 4- (3-bromophenyl) -2,6-dipetylpyrimidine (73.34) in a 1000 mL round bottom flask equipped with a nitrogen atmosphere stirrer. mmol) and 12.81 g (133.35 mmol) of sodium tert-butoxy were dissolved in 670 ml of toluene, and then 3.05 g (3.33 mmol) of palladium dibenzylideneacetone and 2.7 ml of tertiary butyl were added dropwise. The reaction solution was heated and stirred at 110 degrees under a stream of nitrogen for 12 hours. After completion of the reaction, the reaction mixture was poured into methanol, and the solid was filtered. Then, the solid was dissolved in chlorobenzene, and then activated carbon and anhydrous magnesium sulfate were stirred. The solution was filtered and then recrystallized with chlorobenzene and methanol to obtain 38 g (67% yield) of compound C-24.

[M + H] ⁺ molecular weight 857.01 of A1 synthesized by LC-Mass was confirmed.

Example 6: Preparation of Formula C-36

Scheme 6

First Step: Synthesis of Formula (L)

60.74 g (186.9 mmol), 2- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -dibenzothiophene 60.74 g (3,6-dibromocarbazole) 63.73 g (205.6 mmol) and 10.8 (9.35 mmol) of tetrakistriphenylphosphinopalladium were suspended in 400 ml of 2M aqueous potassium carbonate solution and 500 ml of tetrahydrofuran, and heated to reflux for 12 hours under a nitrogen stream. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 57 g (71% yield) of the compound (L).

[M + H] ⁺ molecular weight 428.34 of A1 synthesized by LC-Mass was confirmed.

Second Step: Synthesis of Formula (M)

34.78 g (81.2 mmol), 2,4-diphenyl-6- [3- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) 38.88 g (89.3 mmol) of -phenyl]-[1,3,5] -triazine and 4.7 (4.06 mmol) of tetrakistriphenylphosphinopalladium were suspended in 150 ml of 2M aqueous potassium carbonate solution and 250 ml of tetrahydrofuran, followed by nitrogen. It was heated to reflux for 12 hours under air flow. The reaction solution was added to 2000 ml of MeOH, and the crystallized solid was filtered, and then dissolved in monochlorobenzene to separate silica gel / celite. After removing the appropriate amount of the organic solvent, and recrystallized in MeOH to give 35 g (66% yield) of compound (M).

[M + H] ⁺ molecular weight 656.80 of A1 synthesized by LC-Mass was confirmed.

Third Step: Synthesis of Chemical Formula C-36

32.14 g (48.95 mmol) of the compound represented by compound (M) in a 1000 mL round bottom flask equipped with a stirrer under nitrogen atmosphere, 17.23 g (44.5) of 4- (3-bromophenyl) -2,6-difetylpyrimidine mmol) and 8.55 g (88.99 mmol) of sodium tert-butoxy were dissolved in 450 ml of toluene, and then 2.03 g (2.22 mmol) of palladium dibenzylideneacetone and 1.8 ml of tertiary butyl were added dropwise. The reaction solution was heated and stirred at 110 degrees under a stream of nitrogen for 12 hours. After completion of the reaction, the reaction mixture was poured into methanol, and the solid was filtered. Then, the solid was dissolved in chlorobenzene, and then activated carbon and anhydrous magnesium sulfate were stirred. The solution was filtered and then recrystallized with chlorobenzene and methanol to obtain 31 g (72% yield) of compound C-39.

[M + H] ⁺ molecular weight 963.16 of A1 synthesized by LC-Mass was confirmed.

(Manufacture of organic light emitting device)

Example 7 Fabrication of Organic Photonic Device

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. 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 formula) 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 a phosphorescent green dopant was doped with PhGD (see the following formula) at 7 wt% to form a light emitting layer having a thickness of 300 Pa 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]

Examples 8-12

An organic light emitting diode was manufactured according to the same method as Example 7, except for using Examples 2 to 6 instead of Example 1 (A-6).

Comparative Example 1

In Example 7, an organic light emitting diode was manufactured according to the same method as Example 1 (A-6) 'except that Compound R1 was used as a host.

[R-1]

(Performance Measurement of Organic Light Emitting Diode)

For each of the organic light emitting diodes manufactured in Examples 7 to 12 and Comparative Example 1, the current density change, luminance change, and luminous efficiency according to voltage were measured.

(1) Measurement of change of current density according to 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 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) of the same current density (10 mA / cm ² ) was calculated using the brightness, current density, and voltage measured from (1) and (2) above.

Table 1 summarizes the device evaluation results.

Table 1 Classification Host Initial voltage (Vd) Current efficiency (cd / A) Power efficiency (lm / W) Luminance (cd / m ² ) Color coordinates (CIEx) Color coordinates (CIEy) Comparative Example 1 R1 6.90 49.53 23.07 3000 0.333 0.623 Example 7 A-6 3.79 53.6 44.4 3000 0.358 0.615 Example 8 A-9 3.93 56.8 45.5 3000 0.366 0.609 Example 9 B-18 3.84 55.6 45.6 3000 0.346 0.618 Example 10 B-45 4.01 57.8 45.3 3000 0.357 0.611 Example 11 C-24 4.07 59.0 45.6 3000 0.356 0.615 Example 12 C-36 4.07 59.6 46.0 3000 0.368 0.607

When A1, A-9, B-18, B-45, C-24 and C-36 are used as the host, the efficiency of the device is improved compared to that when the comparative material R1 is applied as the host of the light emitting layer. It was confirmed that the driving voltage is lowered.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims (18)

Compound for an organic optoelectronic device represented by the general formula (1): [Formula 1]

In Chemical Formula 1, L is any one of the following Chemical Formulas 2 to 4, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, At least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, n2 and n3 are any one of integers from 0 to 3, m2 and m3 are 1: [Formula 2] [Formula 3] [Formula 4]

In Chemical Formulas 2 to 4, * At both ends represents a linking position with L ² and L ³ in Formula 1, respectively, 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, or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ 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, or a substituted or unsubstituted C2 to C30 hetero Arylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or Unsubstituted arylamine group or substituted or unsubstituted heteroarylamine group, m1 is 0 or 1. The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by the formula (5): [Formula 5]

In Chemical Formula 5, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, At least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, n2 and n3 are any one of integers from 0 to 3, m2 and m3 are 1, 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, or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ 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, or a substituted or unsubstituted C2 to C30 hetero Arylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or Unsubstituted arylamine group or substituted or unsubstituted heteroarylamine group, m1 is 0 or 1. The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by the following formula (6): [Formula 6]

In Chemical Formula 6, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, At least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, n2 and n3 are any one of integers from 0 to 3, m2 and m3 are 1, 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, or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ 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, or a substituted or unsubstituted C2 to C30 hetero Arylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or Unsubstituted arylamine group or substituted or unsubstituted heteroarylamine group, m1 is 0 or 1. The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by the following formula (7): [Formula 7]

In Chemical Formula 7, L ² and 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, Ar ² and Ar ³ are hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C36 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, At least one of Ar ² and Ar ³ is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, n2 and n3 are any one of integers from 0 to 3, m2 and m3 are 1, 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, or a substituted or unsubstituted C2 to C30 heteroaryl group, L ¹ 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, or a substituted or unsubstituted C2 to C30 hetero Arylene group, n1 is an integer of any one of 0 to 3, Ar ¹ is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group having hole characteristics, substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, substituted or Unsubstituted arylamine group or substituted or unsubstituted heteroarylamine group, m1 is 0 or 1. The method of claim 1, M1 and n1 is 0 compound for an organic optoelectronic device. The method of claim 1, Ar ² and Ar ³ is a compound for an organic optoelectronic device that is a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties. The method of claim 1, Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties is substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted carba Zolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted thiazazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted Benzotriazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group , Substituted or unsubstituted purinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted naphpyri Dinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted phenazinyl group or theirs The combination is a compound for an organic optoelectronic device. The method of claim 1, Substituted or unsubstituted C2 to C30 heteroaryl group having an electronic property is a compound for an organic optoelectronic device that is represented by any one of the formulas (8) to 12. [Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12]

The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas A-1 to A-48. [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-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]

[Formula A-37] [Formula A-38] [Formula A-39]

[Formula A-40] [Formula A-41] [Formula A-42]

[Formula A-43] [Formula A-44] [Formula A-45]

[Formula A-46] [Formula A-47] [Formula A-48]

The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas B-1 to B-48. [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]

The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas C-1 to C-48. [Formula C-1] [Formula C-2] [Formula C-3]

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

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

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

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

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

Formula C-19 Formula C-20 Formula C-21

Formula C-22 Formula C-23 Formula C-24

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

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

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

Formula C-34 Formula C-35 Formula C-36

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

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

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

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

The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is triplet excitation energy (T1) 2.0 eV or more. The method of claim 1, The organic optoelectronic device, an organic optoelectronic device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoelectric drum, and a compound for an organic optoelectronic device that is selected from the group consisting of an organic memory device. In 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 the compound for an organic optoelectronic device according to any one of claims 1 to 13. The method of claim 14, 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 15, The compound for an organic optoelectronic device is included in the light emitting layer. The method of claim 16, The compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in the light emitting layer. A display device comprising the organic light emitting device of claim 14.

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