KR20090052774A - New anthracene derivatives and organic light emitting diode using the same - Google Patents

Abstract

The present invention relates to a novel anthracene derivative and an organic electric device using the same, and the anthracene derivative may serve as hole injection, hole transport, electron injection and transport, or a light emitting material in an organic electric device including an organic light emitting device. In particular, it can serve as a light emitting host alone. The organic electric element according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

Anthracene Derivatives, Organic Electronic Devices

Description

Novel anthracene derivatives and organic electric devices using the same {NEW ANTHRACENE DERIVATIVES AND ORGANIC LIGHT EMITTING DIODE USING THE SAME}

The present invention relates to a novel anthracene derivative and an organic electric device using the same.

An organic electric device means a device requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electric device can be divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is 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 a form of electric element. The second type is an electrical device in which holes and / 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 the organic electric element include an organic light emitting element, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like, all of which are used to inject or transport holes, inject or transport electrons, or light emitting materials to drive the device. need.

Hereinafter, the organic light emitting device will be described in detail. However, in the organic electroluminescent devices, a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials in order 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 diode, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

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 the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic light emitting device to fully exhibit the above-mentioned excellent characteristics, it is supported that a material that forms 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, etc. is supported by a stable and efficient material. Although it should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials continues to be demanded, and the necessity of such material development is the same in the other organic electric devices described above.

Accordingly, the present inventors have synthesized a novel anthracene derivative, and these compounds are used in the light emitting layer in the organic electronic device, confirming that the efficiency increase, the driving voltage drop, and the stability increase effect of the organic electric device is excellent and completed the present invention. It was.

Accordingly, an object of the present invention is to provide a novel anthracene derivative and an organic electronic device using the same.

The present invention provides novel anthracene derivatives.

In addition, the present invention is an organic electric device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer is an anthracene derivative of the present invention It provides an organic electric element comprising a.

The novel anthracene derivative according to the present invention may serve as a light emitting host alone in organic electronic devices. In addition, the anthracene derivative may serve as hole injection, hole transport, electron injection and transport, or a light emitting material in organic electronic devices including organic light emitting devices. Therefore, the organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

The novel anthracene derivatives according to the invention are characterized in that they comprise a compound represented by formula (1):

In Chemical Formula 1,

n = 0 to 1

A ₁ is a compound represented by Formula 2, A ₂ is a compound represented by Formula 3,

중에서 선택되고,L is

Is selected from,

In Chemical Formulas 2 and 3,

R ₁ , R ₂ , R ₄ and R ₅ are the same or different from each other, and each independently halogen, deuterium, amino, nitrile, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, Selected from the group consisting of C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ cycloalkyl groups, C ₃ to C ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups and C ₅ to C ₄₀ heteroaryl groups C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group of the; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₂ to C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ An amino group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group, and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ an aryl group of C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C ₄₀ of; And halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C of ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or a hetero group, an aryl unsubstituted C ₅ ~ C ₄₀ May be selected from, and may form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic with an adjacent group or form a spiro bond,

R ₃ and R ₆ are the same as or different from each other, and each independently hydrogen; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group of the; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₂ to C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ An amino group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group, and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ an aryl group of C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C ₄₀ of; And halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ Group consisting of C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group It may be selected from, to form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic with adjacent groups or to form a spiro bond.

Preferably, the novel anthracene derivative comprises a compound represented by the following formula (4):

In Chemical Formula 4,

R ₁ and R ₄ are different or R ₂ and R ₅ are different asymmetric, and R ₁ to R ₆ are the same as defined in Chemical Formula 1.

Also preferably, the novel anthracene derivatives include a compound represented by the following formula (5):

In Chemical Formula 5,

R ₁ to R ₆ and L are as defined in the formula (1).

In the anthracene derivative represented by Formula 1 according to the present invention, L preferably includes the following structural formula.

In the anthracene derivatives represented by Formulas 2 and 3 according to the present invention, R ₁ , R ₂ , R ₄ and R ₅ are aryl unsubstituted or substituted with deuterium, alkyl, amino, aryl, heteroaryl or phenyl groups. group; A phenyl group unsubstituted or substituted with an aryl group; It is preferable to select from a condensed ring group and a heteroaryl group.

In addition, in the anthracene derivatives represented by Formulas 2 and 3 according to the present invention, R ₃ and R ₆ are an aryl group unsubstituted or substituted with hydrogen, an aryl group, a heteroaryl group or a condensed ring; Or a phenyl group; It is preferable that it is an amino group substituted by the aryl group, heteroaryl group, or the phenyl group.

Specific examples of the novel anthracene derivatives, in particular the compounds represented by the formula (4) according to the present invention include, but are not limited to, the compounds shown in Table 1 below.

Specific examples of the novel anthracene derivatives according to the present invention, in particular the compounds represented by the formula (5) include, but are not limited to, the compounds shown in Table 2 below.

The anthracene derivative represented by Chemical Formula 1 according to the present invention may be prepared through a Suzuki coupling reaction between a dibromo aryl compound and an anthracene boronic acid compound under a palladium catalyst.

The organic electric device according to the present invention is characterized by using an anthracene derivative represented by Chemical Formula 1.

The organic electric device of the present invention can be manufactured by a conventional method and material for manufacturing an organic electric device except for forming one or more organic material layers using the above-described compounds. Hereinafter, an organic light emitting diode will be exemplified.

The above-described compounds of the present invention may not only serve as light emitting materials alone in the organic light emitting device, but may also serve as light emitting hosts with suitable light emitting dopants or light emitting dopants with suitable light emitting hosts.

In one embodiment of the present invention, the organic light emitting device may have a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, the above-described compound according to the invention the organic material layer of the organic light emitting device Except for use in at least one of the layers can be prepared using a conventional method and material for manufacturing an organic light emitting device. The structure of the organic light emitting device according to the present invention is illustrated in FIG.

For example, the organic light emitting device according to the present invention is a metal oxide or a metal oxide or alloy thereof having a conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

As the cathode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the negative electrode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

As the electron transport material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.

The compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electric devices including organic solar cells, organic photoconductors, organic transistors, and the like.

Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited thereto.

The compound of formula 1 according to the present invention may be prepared by a multistage chemical reaction. The preparation of the compounds is described by the following examples. As shown in the examples, some intermediate compounds are prepared first, and compounds of formula 1 are prepared from the intermediate compounds. Exemplary intermediate compounds are compounds A-N below. In these compounds, "Br" may be substituted with any other reactive atom or functional group.

Production Example  One  Preparation of Compound A

Copper bromide (18 g, 80.0 mmol) and t-butyl nitrite (12 mL, 101 mmol) were dispersed in acetonitrile (250 mL) at 65 ° C., stirred, and 2-amino anthraquinone (15 g, 67.2 mmol) was dissolved in 5 mL. Dropwise slowly over minutes. After gas evolution, the reaction solution was cooled to room temperature, the reaction solution was added to a 20% aqueous hydrochloric acid solution (1 L) and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, dried under reduced pressure, and dried by column chromatography. To give a pale yellow Compound A (14.5 g, 75%).

Production Example  2  : Preparation of Compound B

Dissolve 2-bromonaphthalene (11.0 g, 53.1 mmol) in THF (100 mL) dried under nitrogen atmosphere, and slowly add t-butyllithium (46.8 mL, 1.7 M pentane solution) at -78 ° C and at 1 After stirring for a time, Compound A (6.36 g, 22.0 mmol) prepared in Preparation Example 1 was added thereto. After removing the cooling vessel was stirred for 3 hours at room temperature. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting mixture was dissolved in a small amount of ethyl ether and then petroleum ether was added and stirred for several hours to obtain a solid compound. The solid compound was filtered and dried in vacuo to give Compound B (11.2 g, 93%).

Production Example  3  : Preparation of Compound C

In a nitrogen atmosphere, Compound B (11.2 g, 20.5 mmol) prepared in Preparation Example 2 was dispersed in acetic acid (200 mL), followed by potassium iodine (34 g, 210 mmol) and sodium hypophosphite hydrate (37 g, 420 mmol). After the addition was stirred while boiling for 3 hours. After cooling to room temperature, the mixture was filtered, washed with water and methanol, and dried in vacuo to give a pale yellow compound C (7.2 g, 64%). MS [M] = 509

Production Example  4  : Preparation of Compound D

Compound C (5 g, 9.81 mmol), bis (pinacolato) diboron (2.75 g, 10.9 mmol), potassium acetate (2.89g, 29.4 mmol) and palladium (diphenyl) prepared in Preparation Example 3 under a nitrogen atmosphere. Phosphoferrocene) chloride (0.24 g, 3 mol%) was added to a 250 mL flask, and dioxane (50 mL) was added thereto, followed by reflux at 80 ° C. for 6 hours. After cooling the reaction solution to room temperature, distilled water (50 mL) was added and extracted with methylene chloride (50 mL x 3). The methylene chloride was removed under reduced pressure to give a pale yellow solid. The pale yellow solid was ethanol. Washed and dried to obtain Compound D (5.46 g, 92%).

Production Example  5  : Preparation of Compound E

Under a nitrogen atmosphere, 1,5-dibromophenyl (5 g, 17.5 mmol), 4-bromophenylboronic acid (3.5 g, 17.5 mmol), Pd (PPh ₃ ) ₄ (1.0 g, 0.88 mmol) was added to 2M K. ₂ CO ₃ aqueous solution (10 mL) and THF (200 mL) were added and stirred at reflux for about 24 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain Compound E (4.8 g, 75%): MS [M] = 362

Production Example  6  : Preparation of Compound F

A compound prepared in the same manner as in the preparation of Compound E of Preparation Example 5, except that 2,6-dibromonaphthalene was used instead of 1,5-dibromonaphthalene in the preparation of Compound E of Preparation Example 5. F (4.8 g, 75%) was obtained. MS [M + H] < + > = 362

Production Example  7  : Preparation of Compound G

Compound 1 was prepared in the same manner as in the preparation of Compound E of Preparation Example 5, except that 1,4-dibromonaphthalene was used instead of 1,5-dibromonaphthalene in the preparation of Compound E of Preparation Example 5. G (4.8 g, 75%) was obtained. MS [M + H] < + > = 362

Production Example  8  : Preparation of Compound H

Dissolve bromophenyl (8.3 g, 53.1 mmol) in THF (100 mL) dried under a nitrogen atmosphere, and slowly add t-butyllithium (46.8 mL, 1.7 M pentane solution) at -78 ° C for 1 hour at the same temperature. After stirring, Compound A (6.36 g, 22.0 mmol) prepared in Preparation Example 1 was added thereto. After removing the cooling vessel was stirred for 3 hours at room temperature. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting mixture was dissolved in a small amount of ethyl ether and then petroleum ether was added and stirred for several hours to obtain a solid compound. The solid compound was filtered and dried in vacuo to give compound H (9 g, 93%).

Production Example  9  : Preparation of Compound I

In a nitrogen atmosphere, Compound H (9 g, 20.5 mmol) prepared in Preparation Example 8 was dispersed in acetic acid (200 mL), followed by potassium iodine (34 g, 210 mmol) and sodium hypophosphite hydrate (37 g, 420 mmol). After the addition was stirred while boiling for 3 hours. After cooling to room temperature, the mixture was filtered, washed with water and methanol, and dried in vacuo to obtain a pale yellow compound I (7.2 g, 64%). MS [M] = 409

Production Example  10 : Preparation of Compound J

Compound I (4.8 g, 10.5 mmol), bis (pinacolato) diboron (4.3 g, 12.5 mmol), potassium acetate (4.12 g, 42 mmol) and palladium (diphenylphosphinoferrocene) chloride under nitrogen atmosphere 0.26 g, 3 mol%) was added to a 250 mL flask, and dioxane (50 mL) was added thereto, and the mixture was refluxed at 100 ° C. for 12 hours. After cooling the reaction solution to room temperature, distilled water (50 mL) was added and extracted with methylene chloride (50 mL X 3). Methylene chloride was removed under reduced pressure to give a pale yellow solid. This pale yellow solid was washed with ethanol and dried to obtain compound J (4.5 g, 95%). MS [M] = 456

Production Example  11 : Preparation of Compound K

Dissolve 2- (4-bromophenyl) naphthalene (12.6 g, 53.1 mmol) in THF (100 mL) dried under nitrogen atmosphere, and slowly add t-butyllithium (46.8 mL, 1.7 M pentane solution) at -78 ° C. After stirring at the same temperature for 1 hour, Compound A (6.36 g, 22.0 mmol) prepared in Preparation Example 1 was added thereto. After removing the cooling vessel was stirred for 3 hours at room temperature. Aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting mixture was dissolved in a small amount of ethyl ether and then petroleum ether was added and stirred for several hours to obtain a solid compound. The solid compound was filtered and dried in vacuo to give compound K (14 g, 93%).

Production Example  12  : Preparation of Compound L

Compound J (14 g, 20.5 mmol) prepared in Preparation Example 10 was dispersed in acetic acid (200 mL) under nitrogen atmosphere, followed by potassium iodine (34 g, 210 mmol) and sodium hypophosphite hydrate (37 g, 420 mmol). After the addition was stirred while boiling for 3 hours. After cooling to room temperature, the mixture was filtered, washed with water and methanol, and dried in vacuo to obtain a pale yellow compound L (8.8 g, 65%). MS [M] = 661

Production Example  13 : Preparation of Compound M

Dissolve 2- (7-bromonaphthalene) phenyl (12.6 g, 53.1 mmol) in THF (100 mL) dried under nitrogen atmosphere, and slowly dissolve t-butyllithium (46.8 mL, 1.7 M pentane solution) at -78 ° C. After stirring at the same temperature for 1 hour, Compound A (6.36 g, 22.0 mmol) prepared in Preparation Example 1 was added thereto. After removing the cooling vessel was stirred for 3 hours at room temperature. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting mixture was dissolved in a small amount of ethyl ether and then petroleum ether was added and stirred for several hours to obtain a solid compound. The solid compound was filtered and dried in vacuo to give compound M (14 g, 93%).

Production Example  14  : Preparation of Compound N

In a nitrogen atmosphere, Compound M (14 g, 20.5 mmol) prepared in Preparation Example 13 was dispersed in acetic acid (200 mL), followed by potassium iodine (34 g, 210 mmol) and sodium hypophosphite hydrate (37 g, 420 mmol). After the addition was stirred while boiling for 3 hours. After cooling to room temperature, the mixture was filtered, washed with water and methanol, and dried in vacuo to obtain a pale yellow compound N (8.8 g, 65%). MS [M] = 661

Example  One  Preparation of Chemical Formula 1-1

In a nitrogen atmosphere, Compound C (6.36 g, 12.5 mmol) prepared in Preparation Example 3, Compound I (5.11 g, 12.5 mmol), and Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) prepared in Preparation Example 9 above. ) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 1-1 (8 g, 85%). MS [M + H] < + > = 758

Example  2  Preparation of Chemical Formula 1-6

Under nitrogen atmosphere, compound J (5.7 g, 12.5 mmol) prepared in Preparation Example 10, compound L (8.26 g, 12.5 mmol) prepared in Preparation Example 12, Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) ) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 1-6 (9.6 g, 84%). MS [M + H] < + > = 910

Example  3  Preparation of Chemical Formula 1-28

Under nitrogen atmosphere, compound D (6.95 g, 12.5 mmol) prepared in Preparation Example 4, compound N (8.27 g, 12.5 mmol) prepared in Preparation Example 14, Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) ) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 1-28 (10.4 g, 82%). MS [M + H] < + > = 1010

Example  4  Preparation of Chemical Formula 2-150

Under a nitrogen atmosphere, 1,4-dibromonaphthalene (1.5 g, 5.2 mmol), compound D (6.95 g, 12.5 mmol) prepared in Preparation Example 4, Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 2-150 (4.35 g, 85%). MS [M + H] < + > = 984

Example  5  Preparation of Chemical Formula 2-76

Except for using 2,6-dibromonaphthalene instead of 1,4-dibromonaphthalene in the preparation of formula 2-150 of Example 4, the same as in the preparation of formula 2-150 of Example 4 By the method, formula 2-76 (4.2 g, 82%) was obtained. MS [M + H] < + > = 984

Example  6  Preparation of Chemical Formula 2-3

Except for using 1,5-dibromonaphthalene instead of 1,4-dibromonaphthalene in the preparation of Formula 2-150 of Example 4, the same as in the preparation of Formula 2-150 of Example 4 By the method, formula 2-3 (4.2 g, 82%) was obtained. MS [M + H] < + > = 984

Example  7  Preparation of Chemical Formula 2-271

Under nitrogen atmosphere, Compound E (1.5 g, 4.1 mmol) prepared in Preparation Example 5, Compound D (5.0 g, 9.1 mmol) prepared in Preparation Example 4, Pd (PPh ₃ ) ₄ (0.24 g, 0.21 mmol) ) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 2-271 (3.6 g, 82%). MS [M + H] < + > = 1060

Example  8  Preparation of Chemical Formula 2-187

Except for using the compound F prepared in Preparation Example 5 instead of Compound E in Example 7 in the same manner as in the preparation of Formula 2-271 of Example 7 Formula 2-187 (4.2 g, 82% ) MS [M + H] < + > = 1060

Example  9: Preparation of Formula 2-260

Except for using the compound G prepared in Preparation Example 7 instead of Compound E in Example 7 in the same manner as in the preparation of Formula 2-271 of Example 7 Formula 2-260 (4.2 g, 82% ) MS [M + H] < + > = 1060

Example  10  Preparation of Chemical Formula 2-39

Under nitrogen atmosphere, 2,7-ditriplatenaphthalene (3.7 g, 5.2 mmol), compound J (5.7 g, 12.5 mmol) prepared in Preparation Example 10, Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 2-39 (3.47 g, 85%). MS [M + H] < + > = 784

Example  11  Preparation of Chemical Formula 2-322

Under nitrogen atmosphere, 1,5-dibromopyridine (1.2 g, 5.2 mmol), compound J (5.7 g, 12.5 mmol) prepared in Preparation Example 10, Pd (PPh ₃ ) ₄ (0.3 g, 0.26 mmol) Was added to a 2M K ₂ CO ₃ aqueous solution (80 mL) and THF (150 mL) and stirred at reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture and filtered to obtain a solid. This solid was recrystallized from THF and ethanol to give compound 2-322 (3.25 g, 85%). MS [M + H] < + > = 735

Experimental Example  1 to 4  :

A glass substrate (corning 7059 glass) coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1000 Å was placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. Dispersant was used Fischer Co. product, distilled water was Millipore Co. Secondly filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

3,6-bis-2-naphthylphenylamino-N- [4- (2-naphthylphenyl) amino phenyl] carbazole (800 Å), 4,4'-bis [N- (1) on the ITO electrode -Naphthyl) -N-phenylamino] biphenyl (NPB) (300 Hz), each compound 1-1 prepared in Example (Experimental Example 1), 2-3 (Experimental Example 2), 2-76 ( Experimental Example 3) and 2-150 (Experimental Example 4) (300 Hz), and 9,10-bis-2-naphthyl-2- [4- (N-phenylbenzoimidazoyl) phenyl] anthracene (300 Hz) ) Was sequentially vacuumed to form a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

An amine compound (D1) was used as the dopant material in the emission layer.

12 Å thick lithium fluoride (LiF) and 2000 Å thick aluminum were sequentially deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, aluminum is 2 Å / sec, the vacuum degree during deposition is 2 x 10 ^-7 to 5 x 10 ^-8 torr was maintained.

1 is a diagram illustrating a structure of an organic light emitting device according to an exemplary embodiment of the present invention.

Claims (9)

Anthracene derivative represented by the following formula (1): [Formula 1]

In Chemical Formula 1, n = 0 to 1 A ₁ is a compound represented by Formula 2, A ₂ is a compound represented by Formula 3, L is

Is selected from, [Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3, R ₁ , R ₂ , R ₄ and R ₅ are the same or different from each other, and each independently halogen, deuterium, amino, nitrile, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, Selected from the group consisting of C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ cycloalkyl groups, C ₃ to C ₄₀ heterocycloalkyl groups, C ₆ to C ₄₀ aryl groups and C ₅ to C ₄₀ heteroaryl groups C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group of the; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₂ to C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ An amino group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group, and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ an aryl group of C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C ₄₀ of; And halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C of ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ substituted with one or more groups selected from the heteroaryl group consisting of or a hetero group, an aryl unsubstituted C ₅ ~ C ₄₀ May be selected from, and may form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic with an adjacent group or form a spiro bond, R ₃ and R ₆ are the same as or different from each other, and each independently hydrogen; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ -C ₄₀ alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₃ -C ₄₀ cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₃ ~ C ₄₀ heterocycloalkyl group of the; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₂ to C ₄₀ alkenyl group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ A C ₁ to C ₄₀ alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ An amino group unsubstituted or substituted with one or more groups selected from the group consisting of a C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group, and a C ₅ -C ₄₀ heteroaryl group; Halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ an aryl group of C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of unsubstituted C ₆ ~ C ₄₀ of; And halogen, deuterium, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ Group consisting of C ₅ ~ C ₄₀ heteroaryl group unsubstituted or substituted with one or more groups selected from the group consisting of ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group It may be selected from, to form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic with adjacent groups or to form a spiro bond. The anthracene derivative according to claim 1 comprising a compound represented by the following formula (4): [Formula 4]

In Chemical Formula 4, R ₁ and R ₄ are different or R ₂ and R ₅ are different asymmetrics, and R ₁ to R ₆ are as defined in claim 1 above. The anthracene derivative according to claim 1 comprising a compound represented by the following Formula 5.  [Formula 5]

In Chemical Formula 5, R ₁ to R ₆ and L are as defined in claim 1 above. The anthracene derivative of claim 1, wherein L in Formula 1 comprises the following structural formula:

An organic electric device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is an anthracene derivative according to any one of claims 1 to 4. An organic electric element comprising a. The organic electric device of claim 5, wherein the organic material layer includes a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer include the anthracene derivative. The organic electroluminescent device according to claim 5, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the anthracene derivative. The organic electroluminescent device according to claim 5, wherein the organic material layer includes an electron transport layer, and the electron transport layer includes the anthracene derivative. The organic electronic device of claim 5, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

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