KR20090090568A - New anthracene derivatives and organic electronic device using the same - Google Patents

Abstract

An anthracene derivative is provided to ensure efficiency increase, driving voltage lowering, and stability increase of an organic electronic device when an organic layer of the organic electronic device is formed. An anthracene derivative has a structure represented by chemical formula 1. A method for manufacturing the anthracene derivative comprises a step for reacting a halide aryl compound and a boron compound of which position 9 is substituted with an aryl group in the presence of a palladium catalyst. The organic electronic device comprises a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode.

Description

Novel anthracene derivatives and organic electronic devices using the same {NEW ANTHRACENE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE USING THE SAME}

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

In the present specification, an organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. The organic electronic 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 an electronic device of the form. The second type is an electronic device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

Examples of organic electronic devices include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums and organic transistors, all of which are electron / hole injection materials, electron / hole extraction materials, and electron / hole transport materials for driving the devices. Materials or luminescent materials are required. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material, or a light emitting material all operate 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 and a cathode and an organic material layer therebetween. In this case, the organic material layer is often formed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, 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, and the excitons are at the bottom. When it falls to the state, it becomes light. 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 luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce 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 to fully exhibit the excellent characteristics of the organic light emitting device described above, a material forming 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 this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, the development of new materials is still required.

We have found an anthracene derivative with a novel structure. In addition, when the organic layer of the organic electronic device is formed by using the novel anthracene derivative, it has been found that the effect of increasing the efficiency, lowering the driving voltage, and increasing the stability of the device may be exhibited.

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.

The present invention also provides a method for preparing a novel anthracene derivative, which is prepared by reacting a halide aryl compound with an anthracene boron compound substituted with an aryl group at position 9 carbonyl under a palladium catalyst.

The present invention also provides an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, wherein at least one of the organic layers is the novel anthracene derivative. It provides an organic electronic device comprising a.

The novel anthracene compound according to the present invention may be used as an organic material layer material of organic electronic devices including organic light emitting devices by introducing various aryl groups, heteroaryl groups, arylamino groups, etc. into the anthracene compounds. The organic electronic device including the organic light emitting device using the anthracene compound according to the present invention as a material of the organic material layer has excellent characteristics in efficiency, driving voltage, lifespan, and the like.

The novel anthracene derivatives according to the invention include compounds represented by the following formula (1):

In Chemical Formula 1,

L is a direct bond; C ₆ C ₄₀ aryl group and C ₅ C ₂ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ heteroaryl groups An alkenylene group of ˜C ₄₀ ; And halogen, amino group, nitrile group, nitro group, C ₁ An alkyl group of C ₄₀ , C ₂ C ₄₀ Alkenyl group, C ₁ ~ C ₄₀ Alkoxy group, C ₃ A cycloalkyl group of C ₄₀ , C ₂ A heterocycloalkyl group of C ₄₀ , C ₆ C ₄₀ aryl group and C ₅ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ heteroaryl groups It is selected from the group consisting of C ₄₀ arylene group,

Ar ₁ And Ar ₂ are each or simultaneously, C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups An aryl group of ₄₀ ~ C; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₅ unsubstituted or substituted with one or more groups selected from the group consisting of arylamino groups of C ₄₀ A heteroaryl group of ₄₀ ~ C; And C ₁ An alkyl group of C ₄₀ , C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups It is selected from the group consisting of arylamino groups of ~ C ₄₀ ,

Ar ₃ is hydrogen; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups An aryl group of ₄₀ ~ C; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₅ unsubstituted or substituted with one or more groups selected from the group consisting of arylamino groups of C ₄₀ A heteroaryl group of ₄₀ ~ C; And C ₁ An alkyl group of C ₄₀ , C ₆ Aryl of C ₄₀ , C ₅ ~ C ₄₀ heteroaryl group, and a C ₆ ~ C ₄₀ substituted by at least one group selected from the group consisting of an aryl group or unsubstituted C ₆ of It is selected from the group consisting of arylamino groups of ~ C ₄₀ .

Examples of the substituents are described below, but are not limited thereto.

The alkyl group includes, but is not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

The alkoxy group includes, but is not limited to, methoxy, ethoxy, phenyloxy, cyclohexyloxy, naphthyloxy, isopropyloxy, diphenyloxy and the like.

The aryl group includes a phenyl group, naphthyl group, anthracenyl group, biphenyl group, pyrenyl group, perylene group, tetrahydronaphthyl, derivatives thereof, and the like, but is not limited thereto.

The heteroaryl group includes but is not limited to thienyl, pyridyl, furyl, and the like.

The cycloalkyl group includes a cyclohexyl group, a cyclopentyl group, and the like, but is not limited thereto.

The arylamino group is naphthylamino group, biphenylamino group, anthracenylamino group, 3-methyl-phenylamino group, 4-methyl-naphthylamino group, 2-methyl-biphenylamino group, 9-methyl-anthracenylamino group, diphenylamino group , Phenyl naphthyl amino group, ditolyl amino group, phenyl tolyl amino group, carbazole group, triphenyl amino group and the like, but are not limited thereto.

The arylene group includes, but is not limited to, phenylene, biphenylene, and the like.

The halogen includes fluorine, chlorine, bromine and iodine.

Specific examples of the anthracene derivative represented by Formula 1 include the following compounds, but are not limited thereto.

Hereinafter, a method of preparing the anthracene derivative represented by Chemical Formula 1 will be described.

The anthracene derivative represented by Chemical Formula 1 may be prepared using a general method known in the art, such as a Suzuki bonding reaction, by introducing an aryl substituent, heteroaryl group, arylamino group, etc. into an anthracene group.

Specifically, the anthracene derivative represented by Formula 1 may be prepared by reacting a halide aryl compound with an anthracene boron compound substituted with an aryl group at position 9 carbon under a palladium catalyst.

For example, the anthracene derivative represented by Chemical Formula 1 may be prepared as in the reaction process of Scheme 1 below.

Scheme 1

Anthracene derivative represented by Formula 1 according to Scheme 1 is

1) preparing a compound B by reacting a 2-hydroxy-1-bromonaphthalene compound with a Suzuki coupling to a compound A derivative substituted with an aryl at the 9-position under a palladium (Pd) catalyst,

2) preparing a compound C derivative by adding triflic anhydride to the compound B derivative prepared in step 1), and

3) The compound C derivative prepared in step 2) may be prepared by RZ (OH) ₂ or boronate compound RB (OR) ₂ with Suzuki bonding. In this case, R of the boron compound is the same as Ar ₁ of the anthracene derivative represented by Formula 1 above.

In addition, the organic electronic device according to the present invention is an organic electronic device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, one or more of the organic material layer It characterized in that it comprises a compound of the formula (1).

The organic electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic material layer is formed using the above-described compounds.

Hereinafter, the organic light emitting device will be exemplified.

In one exemplary embodiment of the present invention, the organic light emitting device may have a structure including a first electrode, a second electrode, and an organic material layer disposed therebetween. The organic material layer of the organic light emitting device of the present invention may be a single layer structure consisting of one layer, may be a multilayer structure of two or more layers including a light emitting layer. When the organic material layer of the organic light emitting device of the present invention has a multi-layer structure, for example, it may be a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like are stacked. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers. For example, the organic light emitting device of the present invention may have a structure as shown in FIG. In Fig. 1, reference numeral 1 denotes a substrate, 2 an anode, 3 a hole injection layer, 4 a hole transport layer, 5 an organic light emitting layer, 6 an electron transport layer, and 7 a cathode. An organic light emitting device having a structure as shown in FIG. 1 is generally referred to as an organic light emitting device having a forward structure, but the present invention is not limited thereto and includes an organic light emitting device having a reverse structure. That is, the organic light emitting device of the present invention may have a reverse structure in which a substrate, a cathode, an electron transport layer, an organic light emitting layer, a hole transport layer, a hole injection layer, and an anode are sequentially stacked.

When the organic light emitting device according to the present invention has a multi-layered organic material layer, the compound of Formula 1 is a light emitting layer, a hole transport layer, a layer for simultaneously transporting holes and light emission, a layer for simultaneously emitting light and electron transport, electron transport layer, electron transport And / or injection layers and the like. In the present invention, the compound of Formula 1 is particularly preferably included in the electron transport and / or injection layer or the light emitting layer.

The organic light emitting device according to the present invention may be manufactured using a conventional method and material for manufacturing an organic light emitting device, except that the compound of Formula 1 is used in at least one layer of the organic material layer of the organic light emitting device. For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, in order to fabricate an organic light emitting device having a reverse structure as described above, 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 layer may be formed into a smaller number of layers by using a variety of polymer materials, but not by a deposition process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can manufacture.

As the anode 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); ZnO: Al or SnO ₂ Combinations of oxides with metals such as 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 cathode 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 anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injecting materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transporting 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 thereof include 8-hydroxyquinoline 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 transporting 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 depending on the material used.

The compound according to the present invention may also operate on a similar principle to that applied to organic light emitting devices in organic electronic 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 intended to illustrate the invention, whereby the scope of the invention is not limited.

< Production Example  1> Synthesis of Compound of Formula A1

Formula E (5 g, 10.8 mmol), bis (pinacolato) diboron (2.75 g, 10.8 mmol) and potassium acetate (2.89 g, 29.4 mmol) were suspended in dioxane (50 mL). Palladium (diphenylphosphinoferrocene) chloride (0.24 g, 0.3 mmol) was added to the suspension. The resulting mixture was stirred at 80 ° C. for about 6 hours and cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic extract was dried over magnesium sulfate and concentrated in vacuo. The crude product was washed with ethanol and dried in vacuo to give the boronate compound of formula A1 (3.7 g, yield 67%).

MS: [M + H] ⁺ = 507

< Production Example  2> the following formula C1 Synthesis of Compounds

After dissolving the compound of Formula A1 (4.1 g, 8 mmol) and 1-bromo-2-naphthol (2.2 g, 10 mmol) prepared in Preparation Example 1 in tetrahydrofuran (100 mL), 2M carboxylic acid Aqueous potassium solution was added and tetrakistriphenylphosphino palladium (300 mg, 0.26 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the resulting solid was filtered and dried, and recrystallized with THF / EtOH to prepare the compound of Formula B1 (2.8 g, yield 56%).

MS: [M + H] ⁺ = 523

Triethylamine (0.7 g, 6.5 mmol) and trifluoroacetic anhydride (1.3 g, 9.7 mmol) were gradually added dropwise while adding 60 mL of CH ₂ Cl ₂ to the compound of Formula B1 (2.8 g, 5.4 mmol). It was. The mixture was stirred at room temperature for 2 hours, water and CH ₂ Cl ₂ were added to separate the organic layer, and the organic extract was dried over magnesium sulfate and concentrated in vacuo. Purification with CH ₂ Cl ₂ / EtOH afforded the compound of formula C1 (3.0 g, yield 90%).

MS: [M + H] ⁺ = 619

< Example  1> Formula 1- 2 compound  synthesis

1-Phenylboronic acid (1.9 g, 15.6 mmol) and the compound of Chemical Formula C1 (6.1 g, 9.9 mmol) are completely dissolved in tetrahydrofuran (150 mL), and then 2M aqueous potassium carbonate solution is added thereto. Tetrabistriphenylphosphino palladium (300 mg, 0.26 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the resulting solid was filtered and dried, and recrystallized with THF / EtOH to prepare the compound of Chemical Formula 1-2 (4.2 g, yield 46%).

MS: [M + H] ⁺ = 583

< Example  2> Synthesis of Compound of Formula 1-46

2-Naphthylboronic acid (2.7 g, 15.6 mmol) and the compound of Formula C2 (6.1 g, 9.9 mmol) are completely dissolved in tetrahydrofuran (150 mL), followed by 2M aqueous potassium carbonate solution. Tetrabistriphenylphosphino palladium (300 mg, 0.26 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the resulting solid was filtered and dried, and recrystallized with THF / EtOH to prepare the compound of Formula 1-46 (3.8 g, yield 60%).

MS: [M + H] ⁺ = 633

< Example  3> Synthesis of Compound of Formula 1-47

In Example 1, except that 2-naphthylboronic acid was used instead of 1-phenylboronic acid (1-phenylboronic acid) in the same manner as in Example 1 except that To prepare a compound of Formula 1-47.

MS: [M + H] ⁺ = 633

< Example  4> Synthesis of Compound of Formula 1-53

A compound of Chemical Formula 1-53 was prepared in the same manner as in Example 1, except that 1-naphthylboronic acid was used instead of 1-phenylboronic acid in Example 1.

MS [M + H] ⁺ = 633

< Example  5> Synthesis of Compound of Formula 1-58

In Example 2, except that 2-phenyl-5-thiophenylboronic acid was used instead of 2-naphthylboronic acid. The compound of Formula 1-58 was prepared by the method.

MS [M + H] ⁺ = 665

< Example  6> Formula 1- 1 compound  synthesis

A compound of Chemical Formula 1-1 was prepared in the same manner as in Example 1, except that the compound of Chemical Formula C2 was used instead of the compound of Chemical Formula C1 in Example 1.

MS: [M + H] ⁺ = 583

< Example  7> Formula 1- 77 compound  synthesis

Except that the 9.10-dibromoanthracene compound represented by the formula C3 instead of the compound of the formula C1 in Example 1, 2.2 equivalent of 2-naphthylboronic acid instead of 1-phenylboronic acid In the same manner as in Example 1, a compound of Chemical Formula 1-77 was prepared.

MS [M + H] ⁺ = 835

< Example  8> Synthesis of Compound of Formula 1-88

Except for using the compound of formula (C4) in place of the compound of formula (C1) in Example 1, instead of 1 equivalent of 1-phenylboronic acid (2.2 equivalents), in the same manner as in Example 1 88 Compounds were prepared

MS [M + H] ⁺ = 659

< Experimental Example  1 to 6>

The glass substrate coated with ITO (indium tin oxide) at a thickness of 1,500 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol was carried out and dried, and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.

[HAT]

4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 kV) of the following formula, which is a material for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. Formed.

[NPB]

Subsequently, Formula 1-1 (Experimental Example 1), Formula 1-2 (Experimental Example 2), Formula 1-46 (Experimental Example 3), Formula 1-47 (Experimental Example 4), and Formula 1-53 on the hole transport layer. (Experimental Example 5) and Chemical Formulas 1-88 (Experimental Example 6) were each vacuum deposited to a thickness of 300 kPa to form a light emitting layer. 4% of the following compound N, N, N, N'-tetraphenyl-1,6-pyrendiamine (N, N, N, N'-tetraphenyl-1,6-pyrenediamine) was used as a blue light emitting dopant in the light emitting layer. It was.

Alq ₃ (aluminum tris (8-hydroxyquinoline)) having the following chemical formula was vacuum deposited on the emission layer to form an electron injection and transport layer.

[Alq ₃ ]

On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 2,000 kPa in order to form a cathode.

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 2 Å / sec, the vacuum degree during deposition is 2 × 10 ⁻⁷ to 5 × 10 ⁻⁸ torr was maintained.

As a result of applying a forward electric field with the voltage shown in Table 1 to the organic light emitting device manufactured as described above, light having x and y values as shown in Table 1 based on 1931 CIE color coordinate at a current density of 10 mA / cm 2 was obtained. Was observed.

< Comparative example  1>

In Experimental Example 1, an organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound represented by the following Formula 1 was used instead of the compound represented by Formula 1-2 in Experimental Example 1.

[Formula 1]

As a result of applying a forward electric field with the voltage shown in Table 1 to the organic light emitting device manufactured as described above, light having x and y values as shown in Table 1 based on 1931 CIE color coordinate at a current density of 10 mA / cm 2 was obtained. Was observed.

< Experimental Example  7 to 12

In Experimental Examples 1 to 6, an organic light emitting device was manufactured in the same manner except that no dopant was used.

< Comparative example  2>

In Comparative Example 1, the experiment was conducted in the same manner except that the dopant was not used, and is shown in Table 2.

As a result of applying a forward electric field to the organic light emitting device prepared above at the voltage shown in Table 2, light having x and y values as described in Table 2 below on the basis of 1931 CIE color coordinate at a current density of 10 mA / cm 2 was obtained. Was observed.

As can be seen in Table 2, in the organic light emitting device using the anthracene derivative according to the present invention, the organic light emitting device using the compound represented by the general formula 1 showed higher characteristics in brightness, power efficiency, quantum efficiency, excellent blue Indicated.

1 illustrates an example of an organic light emitting device according to the present invention.

2 is an MS graph of a compound according to the present invention synthesized in Example 1. FIG.

3 is an MS graph of a compound according to the present invention synthesized in Example 2. FIG.

4 is an MS graph of a compound according to the present invention synthesized in Example 3. FIG.

5 is an MS graph of a compound according to the present invention synthesized in Example 6.

6 is an MS graph of a compound according to the present invention synthesized in Example 8. FIG.

7 is a UV graph of a compound according to the present invention synthesized in Example 1.

8 is a UV graph of a compound according to the present invention synthesized in Example 2.

9 is a UV graph of the compound according to the present invention synthesized in Example 3.

10 is a UV graph of the compound according to the present invention synthesized in Example 6.

11 is a PL (photoluminescence) graph of the compound synthesized in Example 8 according to the present invention.

Claims (10)

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

In Chemical Formula 1, L is a direct bond; C ₆ C ₄₀ aryl group and C ₅ C ₂ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ heteroaryl groups An alkenylene group of ˜C ₄₀ ; And halogen, amino group, nitrile group, nitro group, C ₁ An alkyl group of C ₄₀ , C ₂ C ₄₀ Alkenyl group, C ₁ ~ C ₄₀ Alkoxy group, C ₃ A cycloalkyl group of C ₄₀ , C ₂ A heterocycloalkyl group of C ₄₀ , C ₆ C ₄₀ aryl group and C ₅ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ heteroaryl groups It is selected from the group consisting of C ₄₀ arylene group, Ar ₁ and Ar ₂ are each or simultaneously, C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups An aryl group of ₄₀ ~ C; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₅ unsubstituted or substituted with one or more groups selected from the group consisting of arylamino groups of C ₄₀ A heteroaryl group of ₄₀ ~ C; And C ₁ An alkyl group of C ₄₀ , C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups It is selected from the group consisting of arylamino groups of ~ C ₄₀ , Ar ₃ is hydrogen; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₆ unsubstituted or substituted with one or more groups selected from the group consisting of C ₄₀ arylamino groups An aryl group of ₄₀ ~ C; C ₆ Aryl of C ₄₀ , C ₅ C ₄₀ heteroaryl group and C ₆ C ₅ unsubstituted or substituted with one or more groups selected from the group consisting of arylamino groups of C ₄₀ A heteroaryl group of ₄₀ ~ C; And C ₁ An alkyl group of C ₄₀ , C ₆ Aryl of C ₄₀ , C ₅ ~ C ₄₀ heteroaryl group, and a C ₆ ~ C ₄₀ substituted by at least one group selected from the group consisting of an aryl group or unsubstituted C ₆ of It is selected from the group consisting of arylamino groups of ~ C ₄₀ . The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Chemical Formula 1 includes a compound represented by the following Chemical Formulas 1-1 to 1-102:

A method for producing an anthracene derivative according to claim 1, which is prepared by reacting a halide aryl compound and an anthracene boron compound having a carbon number 9 substituted with an aryl group under a palladium catalyst. An organic electronic device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes the anthracene derivative of claim 1 Organic electronic devices. The organic electronic device of claim 4, wherein the organic electronic device is an organic light emitting device. The organic electronic device of claim 5, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. The organic electronic device of claim 5, wherein the organic light emitting device is an organic light emitting device having a reverse structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. The organic electronic device of claim 5, wherein the organic material layer of the organic light emitting device includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer. The organic electronic device of claim 5, wherein the organic material layer of the organic light emitting device includes a light emitting layer, and the light emitting layer includes the anthracene derivative. The method according to claim 5, wherein the organic material layer of the organic light emitting device comprises an electron transport layer, an electron injection layer, or an electron transport and electron injection layer, any one of the electron transport layer, the electron injection layer, and the electron transport and electron injection layer An organic electronic device comprising the anthracene derivative.

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