KR20130077471A - Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode - Google Patents

Abstract

PURPOSE: A compound for an organic optoelectronic device is provided to offer triple state excitation energy, high hole or electron transport property, film stability, and thermal stability, and to use the compound as a hole injection/transfer material, a host material, or an electron injecting/transfer material of a light-emitting layer. CONSTITUTION: A compound is denoted by chemical formula 1. In the chemical formula 1: Ar^2 is a substituted or non-substituted C2-30 heteroaryl group with electronic property; Ar^1 is a substituted or non-substituted C6-30 aryl group with hole property, a substituted or non-substituted C2-30 heteroaryl group with hole property, a substituted or non-substituted aryl amine group, or a substituted or non-substituted heteroarylamine group; and L^1-L^3 are a single bond, a substituted or non-substituted C2-10 alkenylene group, a substituted or non-substituted C2-10 alkynylene group, a substituted or non-substituted C6-30 arylene group, or a substituted or non-substituted C2-30 heteroarylene group.

Description

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

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

An organic optoelectronic device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electronic device.

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

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting devices, organic solar cells, organic photo conductor drums, and organic transistors, all of which are used for the injection or transport of holes, An injection or transport material, or a luminescent material.

In particular, organic light emitting diodes (OLEDs) have been attracting attention in recent years as the demand for flat panel displays increases. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

Such an organic light emitting device is a device that converts electric energy into light by applying an electric current to an organic light emitting material, and is usually composed of a structure in which a functional organic layer is interposed between an anode and a cathode. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer in the anode and electrons in the cathode, and the injected holes and the electrons meet and recombine by recombination. High energy excitons are formed. At this time, the exciton formed again moves to the ground state, and light having a specific wavelength is generated.

In recent years, it is known that not only fluorescent light emitting materials but also phosphorescent emitting materials can be used as light emitting materials for organic light emitting devices. Such phosphorescence emission is a phenomenon in which electrons are transferred from a ground state to an excited state, The mechanism consists of a non-luminescent transition of a singlet exciton to a triplet exciton through intersystem crossing, followed by a luminescence of the triplet exciton transitioning to the ground state.

As described above, a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system can be used as a light emitting material in order to increase the light emitting efficiency and stability through the light emitting layer.

In order for the organic luminescent device to fully exhibit the above-described excellent characteristics, a host material and / or a dopant such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, an electron injecting material, The organic material layer for organic light emitting devices has not been sufficiently developed yet. Therefore, development of new materials has been continuously required. The necessity of developing such a material is the same in other organic optoelectronic devices described above.

In addition, the low-molecular organic light-emitting device has good efficiency and long life performance because it is manufactured in the form of a thin film by a vacuum deposition method. The polymer organic light-emitting device uses an inkjet or spin coating method, There is an advantage that the large area is advantageous.

Low molecular organic light emitting devices and polymer organic light emitting devices are attracting attention as next generation displays because they have advantages such as self-emission, fast response, wide viewing angle, ultra-thin, high image quality, durability and wide driving temperature range. Compared to conventional liquid crystal displays (LCDs), it is self-luminous and has good visibility even when dark or external light enters. It can reduce thickness and weight to 1/3 of that of LCD without backlight.

In addition, the response speed is 1000 times faster than that of LCD, so it is possible to realize perfect video without residual image. Therefore, it is anticipated that it will be seen as an optimal display in accordance with the multimedia age in recent years. Based on these advantages, after the first development in the late 1980s, the technology has been rapidly developed 80 times and lifespan 100 times. And organic light-emitting device panels have been announced, and the size of the organic light-emitting device panel is rapidly increasing.

In order to increase the size, it is necessary to increase the luminous efficiency and the lifetime of the device. At this time, the luminous efficiency of the device should be such that the holes and electrons in the light emitting layer are smoothly coupled. However, since the electron mobility of an organic material is generally slower than the hole mobility, in order to efficiently bond holes and electrons in the light-emitting layer, an efficient electron transport layer is used to increase electron injection and mobility from the cathode, It should be able to block the movement of holes.

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

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

Life, efficiency, driving voltage, electrochemical stability, and thermal stability, and a display device including the organic light emitting device.

In one embodiment of the present invention, there is provided a compound for an organic optoelectronic device represented by the following formula (1).

[Formula 1]

In Formula 1, Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group having an electronic property, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substitution or non-having hole properties A substituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group, and L ¹ to L ³ are independently a single bond, a substituted or unsubstituted C2 to C10 alkenyl A ethylene 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, n1 to n3 are independently any one of 0 to 3 is an integer, R ¹ to R ⁶ are independently selected from hydrogen, heavy hydrogen, 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 ring hete An aryl group.

Ar ¹ may be the following Chemical Formula 2 or 3.

[Formula 2] [Formula 3]

In Formulas 2 and 3, R ¹ to R ³ 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 And * represents a position bonded to L ¹ of the formula (1).

Ar ¹ may be the following Formula 4 or 5.

[Formula 4] [Formula 5]

In Formulas 4 and 5, R ¹ to R ³ 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 And * represents a position bonded to L ¹ of the formula (1).

Ar ¹ may be represented by Formula 6 below.

[Formula 6]

In Formula 6, Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, * is a position binding to L ¹ of the formula (1) Indicates.

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 thiaziazolyl 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 a substituent represented by any one of the following Formulas 7 to 11.

[Formula 7] [Formula 8]

[Formula 9] [Formula 10]

[Formula 11]

Ar ³ and Ar ⁴ are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a 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 Substituted triphenylenyl group, substituted or unsubstituted perenyl 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 or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadi Solyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted 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 isoqui Nolinyl 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, It may be a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazineyl group, or a combination thereof.

The compound for an organic optoelectronic device may be represented by any one of Formulas A-1 to A-78.

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

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

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

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

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

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

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

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

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

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

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

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

[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]

[Formula A-49] [Formula A-50] [Formula A-51]

[Formula A-52] [Formula A-53] [Formula A-54]

[Formula A-55] [Formula A-56] [Formula A-57]

[Formula A-58] [Formula A-59] [Formula A-60]

[Formula A-61] [Formula A-62] [Formula A-63]

[Formula A-64] [Formula A-65] [Formula A-66]

[Formula A-67] [Formula A-68] [Formula A-69]

[Formula A-70] [Formula A-71] [Formula A-72]

[Formula A-73] [Formula A-74] [Formula A-75]

[Formula A-76] [Formula A-77] [Formula A-78]

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-84.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula B-64] [Formula B-65] [Formula B-66]

[Formula B-67] [Formula B-68] [Formula B-69]

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

[Formula B-73] [Formula B-74] [Formula B-75]

[Formula B-76] [Formula B-77] [Formula B-78]

[Formula B-79] [Formula B-80] [Formula B-81]

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

The compound for an organic optoelectronic device may have a triplet excitation energy (T1) of 2.0 eV or more.

The organic optoelectronic device may be selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor drum, and an organic memory device.

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

The organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and combinations thereof.

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

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

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

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

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

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

1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that can be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
FIG. 6 is a graph showing lifetime characteristics of devices according to Examples 6 to 10. FIG.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, C1 to C10 alkyl groups such as a C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, A trifluoroalkyl group or a cyano group.

In addition, the substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to Two adjacent substituents among C1 to C10 trifluoroalkyl groups or cyano groups, such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, and a trifluoromethyl group, may be fused to form a ring. .

Means one to three heteroatoms selected from the group consisting of N, O, S and P in one functional group, and the remainder is carbon, unless otherwise defined.

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

As used herein, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.

The alkyl group may be an "unsaturated alkyl group" comprising at least one double bond or triple bond.

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

The alkyl group may be an alkyl group of C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.

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

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

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

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

"Heteroaryl group" means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

In the present specification, the 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), dibenzothiophene (dibenzothiophenyl group), and the like.

In the present specification, the hole property means a property of facilitating the injection into the light emitting layer and the movement in the light emitting layer of the hole formed in the anode due to conduction characteristics along the HOMO level.

Further, the electron characteristic means a property of facilitating the injection of electrons formed in the anode into the luminescent layer and the movement in the luminescent layer due to conduction characteristics along the LUMO level.

The compound for an organic optoelectronic device according to an embodiment of the present invention may include a substituent having an electronic property and a substituent having a hole property in a bicarbazole core.

The carbazolyl group of the core includes a substituent having hole characteristics, and in this case, the HOMO and LUMO levels of the entire compound may 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, the compound for an organic optoelectronic device may be a compound having various energy bandgaps by introducing various substituents to the substituents substituted in the core portion and the core portion.

By using a compound having an appropriate energy level according to the substituent of the compound in an organic optoelectronic device, the hole transporting ability or the electron transporting ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent electrochemical and thermal stability. The lifetime characteristics can be improved when the device is driven.

According to 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, Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group having an electronic property, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substitution or non-having hole properties A substituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group, and L ¹ to L ³ are independently a single bond, a substituted or unsubstituted C2 to C10 alkenyl A ethylene 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, n1 to n3 are independently any one of 0 to 3 is an integer, R ¹ to R ⁶ are independently selected from hydrogen, heavy hydrogen, 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 ring hete An aryl group.

Ar ² may be a substituted or unsubstituted C2 to C30 heteroaryl group having an electronic property, the compound for the organic optoelectronic device due to the substituent is light emitting, hole or electronic properties; Membrane stability; Thermal stability and high triplet excitation energy (T1).

Two carbazole groups that are the bicarbazole core may have a 3-N bond. That is, the third position of one carbazole and the nitrogen position of the other carbazole may be combined. Or a combination of 2-N.

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.

Ar ¹ may be the following Chemical Formula 2 or 3.

[Formula 2] [Formula 3]

In Formulas 2 and 3, R ¹ to R ³ 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 And * represents a position bonded to L ¹ of the formula (1).

Ar ¹ may be the following Formula 4 or 5.

[Formula 4] [Formula 5]

In Formulas 4 and 5, R ¹ to R ³ 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 And * represents a position bonded to L ¹ of the formula (1).

Ar ¹ may be represented by Formula 6 below.

[Formula 6]

In Formula 6, Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, * is a position binding to L ¹ of the formula (1) Indicates.

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.

Ar ² may be a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties, and more specifically, a substituted or unsubstituted C2 to C30 heteroaryl group having electronic properties is a substituted or unsubstituted imidazolyl group, substituted Or unsubstituted triazolyl group, substituted or unsubstituted tetrazolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted oxatriazolyl group, substituted or unsubstituted Substituted thiatriazolyl 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 naphpyridinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted It may be a ring acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group or a combination 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 7 to 11.

[Formula 7] [Formula 8]

[Formula 9] [Formula 10]

[Formula 11]

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, a substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroaryl It may be an amine 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 and the like.

Ar ¹ may be represented by Chemical Formula 6, wherein in Formula 6, Ar ³ and Ar ⁴ are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a 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 peryleneyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted Substituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted Is an unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a 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 Benzoxazineyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazineyl group, substituted or Substituted 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-78, but is not limited thereto.

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

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

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

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

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

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

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

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

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

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

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

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

[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]

[Formula A-49] [Formula A-50] [Formula A-51]

[Formula A-52] [Formula A-53] [Formula A-54]

[Formula A-55] [Formula A-56] [Formula A-57]

[Formula A-58] [Formula A-59] [Formula A-60]

[Formula A-61] [Formula A-62] [Formula A-63]

[Formula A-64] [Formula A-65] [Formula A-66]

[Formula A-67] [Formula A-68] [Formula A-69]

[Formula A-70] [Formula A-71] [Formula A-72]

[Formula A-73] [Formula A-74] [Formula A-75]

[Formula A-76] [Formula A-77] [Formula A-78]

The compound for an organic optoelectronic device may be represented by any one of the following Formulas B-1 to B-84, but is not limited thereto.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula B-64] [Formula B-65] [Formula B-66]

[Formula B-67] [Formula B-68] [Formula B-69]

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

[Formula B-73] [Formula B-74] [Formula B-75]

[Formula B-76] [Formula B-77] [Formula B-78]

[Formula B-79] [Formula B-80] [Formula B-81]

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

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

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

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

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

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

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

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

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

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

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

1 to 5 are sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.

1 to 5, organic light emitting devices 100, 200, 300, 400, and 500 according to an embodiment of the present invention include a cathode 120, a cathode 110, And a structure including at least one organic thin film layer (105).

The anode 120 includes a cathode material. As the anode material, a material having a large work function is preferably used to facilitate injection of holes into the organic thin film layer. Specific examples of the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). And metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO ₂ and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) may be used as the anode.

The cathode 110 includes a cathode material, and the anode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium and the like, , LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca. However, the present invention is not limited thereto. Preferably, a metal electrode such as aluminum may be used as the cathode.

1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 is present as an organic thin film layer 105. The organic thin film layer 105 may exist only in the light emitting layer 130. FIG.

2 illustrates a two-layer organic light emitting device 200 having a light emitting layer 230 including an electron transporting layer and a hole transporting layer 140 as an organic thin film layer 105. As shown in FIG. 2, Similarly, the organic thin film layer 105 may be of a two-layer type including a light emitting layer 230 and a hole transporting layer 140. In this case, the light emitting layer 130 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve the bonding property with a transparent electrode such as ITO and the hole transporting property.

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

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

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

1 to 5, the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, the hole injection layer 170, and the organic thin film layer 105, And combinations thereof include compounds for the organic optoelectronic devices. At this time, the compound for an organic optoelectronic device can be used for the electron transport layer 150 or the electron transport layer 150 including the electron injection layer 160, and when included in the electron transport layer, a hole blocking layer (not shown) It is not necessary to form them separately, and an organic light emitting device having a more simplified structure can be provided.

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

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

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

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

(Preparation of compound for organic optoelectronic device)

Example  1: Preparation of Compound A-1

[Reaction Scheme 1]

In a 1 L round-bottomed flask equipped with a thermometer, a reflux condenser, and a stirrer, 12.8 g of compound I-1 and 19.3 g of compound I-2 were dissolved in 280 mL of toluene in a nitrogen atmosphere. Sodium tert-butoxide, 6.0 g of NaOt-Bu), 1.4 g of trisdibenzylideneacetone dipalladium (Pd2dba3), and 1.3 g of tertiary butyl phosphorus (50% solution in toluene) were added and the reactor was refluxed for 12 hours. After naturally cooling to room temperature, precipitated in 800 mL of methanol and stirred for 1 hour. The resulting solid is filtered, stirred in 800 mL of water for 1 hour in a slurry state, and then filtered again. The filtered solid is dried, dissolved in 500 mL of monochlorobenzene, and passed through a Celite / Silica pad. The solution passed through is concentrated to 200 mL and then naturally cooled to room temperature. The resulting solid is filtered off and washed with 300 mL of acetone. The solid was dried in vacuo at 70 ^° C. for 12 hours to give 14.5 g (58% synthetic yield) of compound A-1 .

Example  2: Preparation of Compound A-3

[Reaction Scheme 2]

In a 1 L round-bottomed flask equipped with a thermometer, a reflux condenser, and a stirrer, 12.7 g of compound I-1 and 19.2 g of compound I-3 were dissolved in 280 mL of toluene in a nitrogen atmosphere. Sodium tert-butoxide, 6.0 g of NaOt-Bu), 1.4 g of trisdibenzylideneacetone dipalladium (Pd2dba3), and 1.3 g of tertiary butyl phosphorus (50% solution in toluene) were added and the reactor was refluxed for 12 hours. After naturally cooling to room temperature, precipitated in 800 mL of methanol and stirred for 1 hour. The resulting solid is filtered, stirred in 800 mL of water for 1 hour in a slurry state, and then filtered again. The filtered solid is dried, dissolved in 500 mL of monochlorobenzene, and passed through a Celite / Silica pad. The solution passed through is concentrated to 200 mL and then naturally cooled to room temperature. The resulting solid is filtered off and washed with 300 mL of acetone. The solid was dried in vacuo at 70 ^° C. for 12 hours to give 18.1 g (75% synthetic yield) of compound A-3 .

Example  3: Preparation of Compound A-7

Scheme 3

In a 1 L round bottom flask equipped with a thermometer, a reflux condenser and a stirrer, 10.0 g of compound I-4 and 19.3 g of compound I-2 were dissolved in 280 mL of toluene in a nitrogen atmosphere. Sodium tert-butoxide, 6.0 g of NaOt-Bu), 1.4 g of trisdibenzylideneacetone dipalladium (Pd2dba3), and 1.3 g of tertiary butyl phosphorus (50% solution in toluene) were added and the reactor was refluxed for 12 hours. After naturally cooling to room temperature, precipitated in 800 mL of methanol and stirred for 1 hour. The resulting solid is filtered, stirred in 800 mL of water for 1 hour in a slurry state, and then filtered again. The filtered solid is dried, dissolved in 500 mL of monochlorobenzene, and passed through a Celite / Silica pad. The solution passed through is concentrated to 200 mL and then naturally cooled to room temperature. The resulting solid is filtered off and washed with 300 mL of acetone. The solid was dried in vacuo at 70 ^° C. for 12 hours to give 15.3 g (70% synthetic yield) of compound A-7 .

Example  4: Preparation of Compound A-10

[Reaction Scheme 1]

A 1 L round bottom flask equipped with a thermometer, a reflux condenser and a stirrer was dissolved in a solution of 12.7 g of compound I-1 and 19.3 g of compound I-5 in 280 mL of toluene in a nitrogen atmosphere. 6.0 g of NaOt-Bu), 1.4 g of trisdibenzylideneacetone dipalladium (Pd2dba3), and 1.3 g of tertiary butyl phosphorus (50% solution in toluene) were added and the reactor was refluxed for 12 hours. After naturally cooling to room temperature, precipitated in 800 mL of methanol and stirred for 1 hour. The resulting solid is filtered, stirred in 800 mL of water for 1 hour in a slurry state, and then filtered again. The filtered solid is dried, dissolved in 500 mL of monochlorobenzene, and passed through a Celite / Silica pad. The solution passed through is concentrated to 200 mL and then naturally cooled to room temperature. The resulting solid is filtered off and washed with 300 mL of acetone. The solid was dried in vacuo at 70 ^° C. for 12 hours to afford 15.7 g of compound A-10 (synthetic yield 65%).

Example  5: Preparation of Compound A-12

[Reaction Scheme 1]

A 1 L round bottom flask equipped with a thermometer, a reflux condenser and a stirrer was dissolved in a solution of 10.0 g of Compound I-4 and 19.3 g of Compound I-5 in 280 mL of toluene in a nitrogen atmosphere. Sodium tert-butoxide, 6.0 g of NaOt-Bu), 1.4 g of trisdibenzylideneacetone dipalladium (Pd2dba3), and 1.3 g of tertiary butyl phosphorus (50% solution in toluene) were added and the reactor was refluxed for 12 hours. After naturally cooling to room temperature, precipitated in 800 mL of methanol and stirred for 1 hour. The resulting solid is filtered, stirred in 800 mL of water for 1 hour in a slurry state, and then filtered again. The filtered solid is dried, dissolved in 500 mL of monochlorobenzene, and passed through a Celite / Silica pad. The solution passed through is concentrated to 200 mL and then naturally cooled to room temperature. The resulting solid is filtered off and washed with 300 mL of acetone. The solid was dried in vacuo at 70 ^° C. for 12 hours to give 17.5 g of compound A-7 (80% synthetic yield).

(Production of organic light emitting device)

Example  6: Organic photoelectric device  Produce

The glass substrate coated with ITO (Indium tin oxide) having 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, 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 A-1 synthesized in Example 1 as a host on the hole transport layer and doped with phosphorescent green dopant to 7% by weight of PhGD compound to form a light emitting layer of 300 Å thickness by vacuum deposition.

[PhGD]

Subsequently, the following BAlq [Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum] compound was stacked to a thickness of 50 kHz on the emission layer, and sequentially the following Alq3: [Tris (8-hydroxyquinolinato) aluminum] compound was laminated to a thickness of 250 Å to form an electron transport layer. An organic light emitting device was manufactured by sequentially depositing LiF 5 ′ and Al 1000 ′ on the electron transport layer to form a cathode.

Balq [Alq3]

Example  7

An organic light emitting diode was manufactured according to the same method as Example 6 except for using A-3 synthesized in Example 2 instead of Example 1.

Example  8

An organic light emitting diode was manufactured according to the same method as Example 6 except for using A-7 synthesized in Example 3 instead of Example 1.

Example  9

An organic light emitting diode was manufactured according to the same method as Example 6 except for using A-10 synthesized in Example 4 instead of Example 1.

Example  10

An organic light emitting diode was manufactured according to the same method as Example 6 except for using A-12 synthesized in Example 5 instead of Example 1.

Comparative example  One

In Example 6, the following compound CT [3,6-diphenyl-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole] instead of Example 1 was used as a host An organic light emitting device was manufactured in the same manner except for the above.

[CT]

(Performance Measurement of Organic Light Emitting Device)

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 in current density with voltage change

For the organic light emitting device manufactured, the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.

(2) Measurement of luminance change according to voltage change

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

(3) Measurement of luminous efficiency

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

(4) device life measurement

Initial luminance was measured at 3,500 cd / m ² . The time until the luminance decreased by 3% was measured.

Table 1 summarizes the device evaluation results.

Classification Host Vd Cd / A cd / m ² CIEx CIEy Life (h) Comparative Example 1 CT 3.3 42.2 3500 0.350 0.620 25 Example 6 A-1 3.7 68 3500 0.34 0.62 100 Example 7 A-3 4.2 59 3500 0.34 0.62 60 Example 8 A-7 3.7 67 3500 0.34 0.62 76 Example 9 A-10 3.7 68 3500 0.34 0.62 > 140 Example 10 A-12 3.6 70 3500 0.33 0.63 86

When Comparative Example 1 is used as a host of the light emitting layer, when Examples 6 to 10 are used as the host, it was confirmed that the efficiency and life of the device is improved.

6 is a graph showing lifetime characteristics of devices according to Examples 6 to 10. FIG.

It can be seen from FIG. 6 that the life characteristics of the devices according to the embodiments 6 to 10 are improved.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100: organic light emitting device 110: cathode
120: anode 105: organic thin film layer
130: luminescent layer 140: hole transport layer
150: electron transport layer 160: electron injection layer
170: Hole injection layer 230: Emission layer + Electron transport layer

Claims (16)

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

In Chemical Formula 1,
Ar ² is a substituted or unsubstituted C 2 to C 30 heteroaryl group having electronic properties,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group having hole characteristics, a substituted or unsubstituted C2 to C30 heteroaryl group having hole characteristics, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroaryl An amine group,
L ¹ to L ³ are independently a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,
n1 to n3 are each independently an integer of 0 to 3,
R ¹ to R ⁶ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The method of claim 1,
Ar ¹ is a compound for an organic optoelectronic device of Formula 2 or 3.
[Chemical Formula 2] < EMI ID =

In the above Formulas 2 and 3,
R ¹ to R ³ 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,
* Represents a position binding to L ¹ of the formula (1).
The method of claim 1,
Ar ¹ is a compound for an organic optoelectronic device of Formula 4 or 5.
[Chemical Formula 4]

In the above formulas (4) and (5)
R ¹ to R ³ 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,
* Represents a position binding to L ¹ of the formula (1).
The method of claim 1,
Ar ¹ is a compound for an organic optoelectronic device of Formula 6:
[Chemical Formula 6]

In Formula 6,
Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Represents a position binding to L ¹ of the formula (1).
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 thiaziazolyl 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,
The substituted or unsubstituted C2 to C30 heteroaryl group having the electronic properties is a compound for an organic optoelectronic device which is represented by any one of the following formulas 7 to 11.
[Chemical Formula 7]

[Formula 9] [Formula 10]

(11)

5. The method of claim 4,
Ar ³ and Ar ⁴ are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a 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 Substituted triphenylenyl group, substituted or unsubstituted perenyl 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 or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadi Solyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted 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 isoqui Nolinyl 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, A substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazinyl group, or a combination thereof.
The method of claim 1,
Compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas A-1 to A-78.
[Formula A-1] [Formula A-2] [Formula A-3]

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

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

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

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

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

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

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

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

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

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

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

[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]

[Formula A-49] [Formula A-50] [Formula A-51]

[Formula A-52] [Formula A-53] [Formula A-54]

[Formula A-55] [Formula A-56] [Formula A-57]

[Formula A-58] [Formula A-59] [Formula A-60]

[Formula A-61] [Formula A-62] [Formula A-63]

[Formula A-64] [Formula A-65] [Formula A-66]

[Formula A-67] [Formula A-68] [Formula A-69]

[Formula A-70] [Formula A-71] [Formula A-72]

[Formula A-73] [Formula A-74] [Formula A-75]

[Formula A-76] [Formula A-77] [Formula A-78]

The method of claim 1,
Compound for an organic optoelectronic device is a compound for an organic optoelectronic device that is represented by any one of the formulas B-1 to B-84.
[Formula B-1] [Formula B-2] [Formula B-3]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula B-64] [Formula B-65] [Formula B-66]

[Formula B-67] [Formula B-68] [Formula B-69]

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

[Formula B-73] [Formula B-74] [Formula B-75]

[Formula B-76] [Formula B-77] [Formula B-78]

[Formula B-79] [Formula B-80] [Formula B-81]

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

The method of claim 1,
Wherein the compound for an organic optoelectronic device has a triplet excitation energy (T1) of 2.0 eV or more.
The method of claim 1,
Wherein the organic optoelectronic device is selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor drum, and an organic memory device.
An organic light emitting device comprising an anode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode,
Wherein at least one of the organic thin film layers comprises the compound for an organic optoelectronic device according to claim 1.
The method of claim 12,
Wherein the organic thin film layer is selected from the group consisting of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and combinations thereof.
The method of claim 13,
Wherein the compound for an organic optoelectronic device is contained in a light emitting layer.
15. The method of claim 14,
Wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in a light emitting layer.
A display device comprising the organic light emitting device of claim 12.

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