WO2013027906A1 - Compound for an organic optoelectric device, organic light emitting element including same, and display device including the organic light emitting element - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectric device, to an organic light emitting element including same, and to a display device including the organic light emitting element. The compound in chemical formula 1 for an organic optoelectric device is provided, so that an organic optoelectric device can be manufactured having a superior service life, due to having superior electrochemical and thermal stability, and high luminous efficacy even under a low driving voltage.

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 aspect of the invention, there is provided a compound for an organic optoelectronic device represented by the formula (1).

[Formula 1]

In Formula 1, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

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

[Formula 2]

In Formula 2, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

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

[Formula 3]

In Chemical Formula 3, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

The compound for an organic optoelectronic device may be represented by the following formula (4).

[Formula 4]

In Formula 4, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted Oxadiazolyl group, substituted or unsubstituted oxtriazolyl group, substituted or unsubstituted thiatriazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted Substituted 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 naphpyridinyl group, substituted or unsubstituted quinine group Salicylate group, may be substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted arc piperidinyl group, a substituted or unsubstituted phenanthryl trolley group, a substituted or unsubstituted phenacyl group possess, or a combination thereof.

The compound for an organic optoelectronic device may be represented by one of Formulas A1 to A28.

[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

Formula A7 Formula A8 Formula A9

[Formula A10] [Formula A11] [Formula A12]

[Formula A13] [Formula A14] [Formula A15]

[Formula A16] [Formula A17] [Formula A18]

Formula A19 Formula A20 Formula A21

[Formula A22] [Formula A23] [Formula A24]

[Formula A25] [Formula A26] [Formula A27]

Formula A28

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B1 to B28.

[Formula B1] [Formula B2] [Formula B3]

[Formula B4] [Formula B5] [Formula B6]

[Formula B7] [Formula B8] [Formula B9]

[Formula B10] [Formula B11] [Formula B12]

[Formula B13] [Formula B14] [Formula B15]

[Formula B16] [Formula B17] [Formula B18]

[Formula B19] [Formula B20] [Formula B21]

[Formula B22] [Formula B23] [Formula B24]

[Formula B25] [Formula B26] [Formula B27]

[Formula B28]

The compound for an organic optoelectronic device may be represented by any one of Formulas C1 to C47.

[Formula C1] [Formula C2] [Formula C3]

[Formula C3] [Formula C4] [Formula C5]

[Formula C6] [Formula C7] [Formula C8]

[Formula C9] [Formula C10] [Formula C11]

[Formula C12] [Formula C13] [Formula C14]

[Formula C15] [Formula C16] [Formula C17]

Formula C18 Formula C19 Formula C20

[Formula C21] [Formula C22] [Formula C23]

[Formula C24] [Formula C25] [Formula C26]

[Formula C27] [Formula C28] [Formula C29]

[Formula C30] [Formula C31] [Formula C32]

[Formula C33] [Formula C34] [Formula C35]

Formula C36 Formula C37 Formula C38

[Formula C39] [Formula C40] [Formula C41]

[Formula C42] [Formula C43] [Formula C44]

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 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.

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, halogen group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, 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. Substituted by a trifluoroalkyl group or a cyano group.

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" meaning that it does not contain any alkenes or alkyne groups.

"Alkene group" means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond, and "alkyne group" means at least two carbon atoms of at least one carbon-carbon triple bond It means a functional group formed. 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. The alkyl group may be a medium sized alkyl group which is C1 to C10. The alkyl group may be a lower alkyl group which is C1 to C6.

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:

Typical alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl and cyclo It means a functional group which may be substituted with one or more groups individually and independently selected from pentyl group, cyclohexyl group and the like.

"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.

"Spiro structure" means a ring structure having one carbon as a contact point. The spiro structure may also be used as a compound containing a spiro structure or a substituent including a spiro structure.

In the present specification, the hole property means a property that has a conduction property along the HOMO level, thereby facilitating injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.

In addition, in the present specification, the electronic characteristic means a characteristic that has conductivity characteristics along the LUMO level to facilitate the injection and movement of the electrons formed in the cathode into the light emitting layer.

The compound for an organic optoelectronic device according to an embodiment of the present invention has a structure in which a substituent is selectively bonded to a core portion to which two carbazoles are bonded.

Two of the substituents bonded to the core may be a substituent having excellent 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. Thus, the compound may be used as an electron injection layer and a transfer layer or a hole injection layer and a transfer layer.

By using a compound having an appropriate energy level in the organic photoelectric device according to the substituent of the compound, the electron transport ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent life time when driving the organic photoelectric device due to excellent electrochemical and thermal stability. Properties can be improved.

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

In one embodiment of the present invention provides a compound for an organic optoelectronic device represented by the formula (1).

[Formula 1]

In Formula 1, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

The compound represented by Chemical Formula 1 may have a carbazole having excellent bipolar characteristics as a core.

R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl Groups or combinations thereof.

By appropriate combination of the above substituents, it is possible to prepare a compound having a structure excellent in thermal stability or resistance to oxidation.

By a suitable combination of the substituents can be prepared a structure of the asymmetric bipolar (bipolar) characteristics, the structure of the asymmetric bipolar characteristics can be expected to improve the luminous efficiency and performance of the device by improving the major and electron transfer ability.

L ¹ and L ² are the same as or different from each other, and 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 aryl It may be a ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group or a combination thereof.

The substituent in which the pi bond exists among the substituents increases the triplet energy bandgap by controlling the pi conjugate length (π-conjugation length) of the entire compound so that it can be very usefully applied to the light emitting layer of the organic photoelectric device as a phosphorescent host. can do.

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

As described above, Ar ¹ and Ar ² may be the same as or different from each other, and may independently have a substituted or unsubstituted heteroaryl group having electronic properties.

Specific examples of the substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties include substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, and substituted Or an unsubstituted oxadiazolyl group, a substituted or unsubstituted oxatriazolyl group, a substituted or unsubstituted thiatriazolyl group, a substituted or unsubstituted benzimidazolyl group, a 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, quinoline, substituted Or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or non Hwandoen acridine, a substituted or unsubstituted phenanthryl such as the Troll Lin, substituted or unsubstituted phenazine. Combinations of these are also possible.

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

[Formula 2]

In Formula 2, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

That is, the binding position of the carbazole which is the core may be bonded as shown in Formula 2. The binding position may be an advantage in synthesizing the compound to one of the high reactivity of the carbazole or carbazole derivatives.

In addition, when bonded to the position, there is an advantage that can introduce a substituent having an electron transfer / transport characteristics while minimizing the change in the conjugate length of the entire compound that can bring about a change in the energy band.

Details related to the specific substituents of Chemical Formula 2 are omitted because they are similar to Chemical Formula 1 described above.

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

[Formula 3]

In Chemical Formula 3, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

The structure is a structure in which the binding position of both carbazole groups is defined in the structure of the compound for an organic optoelectronic device represented by Formula 1 above. This structure has the advantage of improving the bandgap and triplet energy bandgap because the molecular structure is more non-planarized to limit the conjugate length.

Details related to the specific substituents of Formula 3 are omitted because they are similar to those of Formula 1 described above.

The compound for an organic optoelectronic device may be represented by the following formula (4).

[Formula 4]

In Formula 4, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 To C30 heteroaryl group or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently a substituted or unsubstituted heteroaryl group having electronic properties, and L ¹ and L ² are the same or different from each other 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, a substituted or unsubstituted C2 to C30 Heteroarylene group or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2.

The structure of Formula 4 is a structure defining the binding position of both carbazole of the core in the structure of the formula (1). Such a core structure may have an appropriate HOMO energy and has an advantage of easy synthesis.

Other descriptions of the substituent of Formula 4 will be omitted because it is similar to the description of Formula 1 described above.

The compound for an organic optoelectronic device may be represented by any one of Formulas A1 to A28, but is not limited thereto.

[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

Formula A7 Formula A8 Formula A9

[Formula A10] [Formula A11] [Formula A12]

[Formula A13] [Formula A14] [Formula A15]

[Formula A16] [Formula A17] [Formula A18]

Formula A19 Formula A20 Formula A21

[Formula A22] [Formula A23] [Formula A24]

[Formula A25] [Formula A26] [Formula A27]

Formula A28

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B1 to B28, but is not limited thereto.

[Formula B1] [Formula B2] [Formula B3]

[Formula B4] [Formula B5] [Formula B6]

[Formula B7] [Formula B8] [Formula B9]

[Formula B10] [Formula B11] [Formula B12]

[Formula B13] [Formula B14] [Formula B15]

[Formula B16] [Formula B17] [Formula B18]

[Formula B19] [Formula B20] [Formula B21]

[Formula B22] [Formula B23] [Formula B24]

[Formula B25] [Formula B26] [Formula B27]

[Formula B28]

The compound for an organic optoelectronic device may be represented by any one of the following Formulas C1 to C47, but is not limited thereto.

[Formula C1] [Formula C2] [Formula C3]

[Formula C3] [Formula C4] [Formula C5]

[Formula C6] [Formula C7] [Formula C8]

[Formula C9] [Formula C10] [Formula C11]

[Formula C12] [Formula C13] [Formula C14]

[Formula C15] [Formula C16] [Formula C17]

Formula C18 Formula C19 Formula C20

[Formula C21] [Formula C22] [Formula C23]

[Formula C24] [Formula C25] [Formula C26]

[Formula C27] [Formula C28] [Formula C29]

[Formula C30] [Formula C31] [Formula C32]

[Formula C33] [Formula C34] [Formula C35]

Formula C36 Formula C37 Formula C38

[Formula C39] [Formula C40] [Formula C41]

[Formula C42] [Formula C43] [Formula C44]

The compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 110 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This enables the implementation of high efficiency organic optoelectronic devices.

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 electron transport layer or the electron 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 photoelectric 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 are provided. 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 in particular, when included in the electron transport layer, a hole blocking layer (not shown). Since it is not necessary to form separately, it is desirable to provide an organic light emitting device having a simplified structure.

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 Synthesis of Compound Represented by Formula (A1)

Compound represented by the formula A1 presented as a specific example of the compound for an organic optoelectronic device of the present invention was synthesized by the same method as in Scheme 1 below.

Scheme 1

First Step: Synthesis of Compound (A)

44.3 g (180.3 mmol) of 3-bromocarbazole, 67.1 g (216.3 mmol) of 4-2-bromo-3,5-diphenylpyridine, 3.6 g (36.06 mmol) of copper (I) in a 2000 mL round flask , 37.4 g (270.4 mmol) of potassium carbonate and 6.5 g (36.06 mmol) of 1,10-phenanthrosine were stirred in 800 ml of dimethyl sulfoxide for 8 hours at 150 ° C.

The reaction solution was poured into 2500 ml of water, stirred, and the solid precipitated in the reaction solution was washed with methanol and filtered under reduced pressure to obtain a solid. The solid was dissolved in chlorobenzene and filtered through silica gel to obtain 67 g (yield 78%) of the intermediate compound (A).

LC-Mass synthesized [M + H] ⁺ molecular weight 475.38 was confirmed.

Second Step: Synthesis of Compound Represented by Formula (B)

32.669 g (68.7 mmol) of the compound represented by compound (A), 26.1 g (103.0 mmol) of tetramethyldioxaborole, 3.7 g (2.75 mmol) of palladium iphenylpyridinoferrocenedichloride, and 20.2 g (206.1 mmol) of acetyl potassium ) Was suspended in 400 ml of dimethylsulfoxide and heated to 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 filtered with silica. An appropriate amount of the solvent was removed and recrystallized in MeOH to give 34 g (95% yield) of the intermediate compound (B).

Confirmed [M + H] ⁺ molecular weight 522.25 of A1 synthesized by LC-Mass.

Third Step: Synthesis of Compound Represented by Formula (A1)

20.6 g (43.3 mmol) of the compound represented by Compound (A), 18.8 g (36.1 mmol) of the compound represented by Compound (B) and 1.2 g (1.0 mmol) of tetrakistriphenylphosphinopalladium were dissolved in 100 ml of 2M aqueous potassium carbonate solution. And suspended in 110 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 20g (Yield 70%) of Compound A1.

LC-Mass synthesized [M + H] ⁺ molecular weight of 790.95 was confirmed.

Example 2: Synthesis of Compound Represented by Formula (A7)

23.7 g (49.7 mmol) of the compound represented by the compound (C), 21.6 g (41.4 mmol) of the compound represented by the compound (B) and 1.44 g (1.2 mmol) of tetrakistriphenylphosphinopalladium were added to 110 ml of a 2M aqueous potassium carbonate solution. And suspended in 120 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 removal of an appropriate amount of the organic solvent, and recrystallized in MeOH to give 25g (72% yield) of Compound A7.

Confirmed [M + H] ⁺ molecular weight 792.93 of A7 synthesized by LC-Mass.

Example 3: Synthesis of Compound Represented by Formula (B3)

18.5 g (38.8 mmol) of the compound represented by the compound (D), 16.9 g (32.3 mmol) of the compound represented by the compound (E), and 1.12 g (1.0 mmol) of tetrakistriphenylphosphinopalladium were added to 80 ml of a 2M aqueous potassium carbonate solution. And suspended in 90 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 removal of an appropriate amount of the organic solvent, and recrystallized in MeOH to give 19g (71% yield) of Compound B3.

Confirmed [M + H] ⁺ molecular weight 794.9 of B3 synthesized by LC-Mass.

Example 4: Synthesis of Compound Represented by Formula (B11)

22.3 g (43.3 mmol) of the compound represented by the compound (F), 18.9 g (36.1 mmol) of the compound represented by the compound (E) and 1.25 g (1.1 mmol) of tetrakistriphenylphosphinopalladium were added to 100 ml of a 2M aqueous potassium carbonate solution. And suspended in 110 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, recrystallized in MeOH to give 25g (Yield 75%) of compound B11.

LC-Mass synthesized [M + H] ⁺ molecular weight 830.97 of B11.

Example 5: Synthesis of Compound Represented by Formula (C2)

18.5 g (38.9 mmol) of the compound represented by Compound (G), 17.0 g (32.4 mmol) of the compound represented by Compound (E), and 1.12 g (0.97 mmol) of tetrakistriphenylphosphinopalladium were added to 100 ml of a 2M aqueous potassium carbonate solution. And suspended in 110 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 removal of an appropriate amount of the organic solvent, and recrystallized in MeOH to give 19g (71% yield) of compound C2.

LC-Mass synthesized [M + H] ⁺ molecular weight 792.93 of B11.

(Manufacture of organic light emitting device)

Example 6 Fabrication of Organic Photoelectric Device

The glass substrate coated with ITO (Indium tin oxide) 1500 thin film was washed with distilled water ultrasonic. 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, the following HTM compound was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 1200 Å.

[HTM]

………

… … …

Using the material (A1) synthesized in Example 1 as a host on the hole transport layer, and a phosphorescent green dopant of the following PhGD compound to 7% by weight to form a light emitting layer of 300 Å thickness 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

In Example 6, an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 2 instead of the compound according to Example 1.

Example 8

In Example 6, an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 3 instead of the compound according to Example 1.

Example 9

In Example 6, an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 4 instead of the compound according to Example 1.

Example 10

In Example 6, an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound according to Example 5 instead of the compound according to Example 1.

Comparative Example 1

Example 7

In Example 6, an organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound represented by the following Formula R1 instead of the compound according to Example 1.

[Formula R1]

(Performance Measurement of Organic Light Emitting Diode)

For each organic light emitting device manufactured in Examples 6 to 10 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 Drive voltage (Vd, V) Luminous Efficiency (Cd / A) Power efficiency (lm / W) Luminance (cd / m ² ) Color coordinates CIEx Color coordinates Comparative Example 1 R1 7.0 49.24 22.09 3000 0.333 0.623 Example 6 A1 5.09 59.8 36.9 3000 0.340 0.622 Example 7 A7 5.04 58.4 36.4 3000 0.341 0.621 Example 8 B3 5.37 56.1 32.9 3000 0.339 0.623 Example 9 B11 5.21 53.5 32.3 3000 0.338 0.623 Example 10 C2 5.17 54.9 33.4 3000 0.338 0.623

Compared with the organic light emitting device according to Comparative Example 1, it was found that the organic light emitting device according to Examples 6 to 10 is advantageous in terms of efficiency and driving voltage of the device.

In the results of Table 1, the structure of the two carbazole binding sites of the core 3-3 '(A1 or A7) is 2-3 (the C2) or 2-2' (the B3 or B11) structure It can be seen that it is excellent in terms of efficiency.

However, it can be seen that the structure of the two carbazole binding sites, which are cores, is 2-3 (the C2) or 2-2 '(the B3 or B11) also has better efficiency than Comparative Example 1.

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.

<Description of symbols>

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

Claims (16)

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

In Chemical Formula 1, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently represent a substituted or unsubstituted heteroaryl group having electronic properties, L ¹ and L ² are the same as or different from each other, and 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 aryl A ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2. The method of claim 1, Compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by the following formula (2): [Formula 2]

In Chemical Formula 2, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently represent a substituted or unsubstituted heteroaryl group having electronic properties, L ¹ and L ² are the same as or different from each other, and 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 aryl A ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2. The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device is represented by the following formula (3): [Formula 3]

In Chemical Formula 3, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently represent a substituted or unsubstituted heteroaryl group having electronic properties, L ¹ and L ² are the same as or different from each other, and 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 aryl A ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2. The method of claim 1, The compound for an organic optoelectronic device is a compound for an organic optoelectronic device is represented by the following formula (4): [Formula 4]

In Chemical Formula 4, R ¹ to R ⁶ are the same as or different from each other, and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group Or a combination thereof, Ar ¹ and Ar ² are the same as or different from each other, and independently represent a substituted or unsubstituted heteroaryl group having electronic properties, L ¹ and L ² are the same as or different from each other, and 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 aryl A ethylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, n and m are the same as or different from each other, and are each independently an integer of 0 to 2. The method of claim 1, Substituted or unsubstituted C2 to C30 heteroaryl group having the above electronic properties, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted Oxadiazolyl group, substituted or unsubstituted oxtriazolyl group, substituted or unsubstituted thiatriazolyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted Substituted 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 naphpyridinyl group, substituted or unsubstituted quinine group Compound for an organic optoelectronic device, which is a salinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a combination thereof . Compound for an organic optoelectronic device represented by any one of formulas A1 to A28. [Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

Formula A7 Formula A8 Formula A9

[Formula A10] [Formula A11] [Formula A12]

[Formula A13] [Formula A14] [Formula A15]

[Formula A16] [Formula A17] [Formula A18]

Formula A19 Formula A20 Formula A21

[Formula A22] [Formula A23] [Formula A24]

[Formula A25] [Formula A26] [Formula A27]

Formula A28

Compound for an organic optoelectronic device represented by any one of the formulas B1 to B28. [Formula B1] [Formula B2] [Formula B3]

[Formula B4] [Formula B5] [Formula B6]

[Formula B7] [Formula B8] [Formula B9]

[Formula B10] [Formula B11] [Formula B12]

[Formula B13] [Formula B14] [Formula B15]

[Formula B16] [Formula B17] [Formula B18]

[Formula B19] [Formula B20] [Formula B21]

[Formula B22] [Formula B23] [Formula B24]

[Formula B25] [Formula B26] [Formula B27]

[Formula B28]

Compound for an organic optoelectronic device represented by any one of the formulas C1 to C44. [Formula C1] [Formula C2] [Formula C3]

[Formula C3] [Formula C4] [Formula C5]

[Formula C6] [Formula C7] [Formula C8]

[Formula C9] [Formula C10] [Formula C11]

[Formula C12] [Formula C13] [Formula C14]

[Formula C15] [Formula C16] [Formula C17]

Formula C18 Formula C19 Formula C20

[Formula C21] [Formula C22] [Formula C23]

[Formula C24] [Formula C25] [Formula C26]

[Formula C27] [Formula C28] [Formula C29]

[Formula C30] [Formula C31] [Formula C32]

[Formula C33] [Formula C34] [Formula C35]

Formula C36 Formula C37 Formula C38

[Formula C39] [Formula C40] [Formula C41]

[Formula C42] [Formula C43] [Formula C44]

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 a compound for an organic optoelectronic device according to any one of claims 1 to 9. The method of claim 10, The organic thin film layer is selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. The method of claim 10, The compound for an organic optoelectronic device is an organic light emitting device which is contained in a hole transport layer or a hole injection layer. The method of claim 10, The compound for an organic optoelectronic device is included in the light emitting layer. The method of claim 10, The compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in the light emitting layer. The method of claim 10, The compound for an organic optoelectronic device is used as a fluorescent blue dopant material in the light emitting layer. A display device comprising the organic light emitting device of claim 10.

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