KR101396647B1 - New anthracene derivatives, preparation method thereof and organic electronic device using the same - Google Patents

Abstract

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

The anthracene derivative according to the present invention can act as a hole injecting, hole transporting, electron injecting, electron transporting or luminescent material in an organic electronic device including an organic light emitting device, and in particular, it can serve as a light emitting host, preferably a green host can do. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

A light emitting material, an organic light emitting element

Description

TECHNICAL FIELD [0001] The present invention relates to a novel anthracene derivative, a method for producing the same, and an organic electronic device using the same. BACKGROUND ART [0002]

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

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device 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 that injects holes and electrons into an organic semiconductor, which forms an interface with the electrode by applying voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor. All of them are used for hole injection or transport materials, electron injection or transport materials, Materials.

Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. 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 a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

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. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material includes blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural colors 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 may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made to solve the above problems occurring in the prior art, and an object of the present invention is to provide a novel anthracene derivative, a method for producing the same, and an organic electronic device using the same.

According to an aspect of the present invention, there is provided an anthracene derivative represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

Q is an arylene group having ₆ to ₂₀ carbon atoms,

R1, R2 and X are each, independently, a halogen, CN, NO _2, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₆ ~ C ₂₀ of the aryl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ of the Substituted with at least one group selected from the group consisting of a cycloalkyl group, a C ₆ to C ₂₀ aryl group, -BRR ', -SiRR'R ", -GeRR'R" and a substituted or unsubstituted C ₅ -C ₂₀ heterocyclic group A substituted or unsubstituted C ₆ -C ₂₀ aryl group; or

Of _{halogen, CN, NO 2, C 1} ~ C 20 alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₆ ~ C ₂₀ aryl amine group, C ₁ ~ C ₂₀ of the A C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₂₀ aryl group, -BRR ', -SiRR'R " and -GeRR'R "and substituted or unsubstituted C ₅ ~ C ₂₀ heterocyclic group of the or unsubstituted C ₅ ~ C ₂₀ substituted with one or more groups selected from the group consisting of a heterocyclic ring,

Wherein R, R 'and R "are each independently selected from the group consisting of hydrogen, a C ₁ to C ₂₀ alkyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₂₀ aryl group or a C ₅ to C ₂₀ heterocyclic ring .

According to a second aspect of the present invention, there is provided a process for preparing an anthracene derivative represented by the general formula (1).

A third aspect of the present invention to achieve the above object is 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 the layer contains an anthracene derivative represented by the general formula (1).

The anthracene derivative according to the present invention can act as a hole injecting, hole transporting, electron injecting, electron transporting or luminescent material in an organic electronic device including an organic light emitting device, and in particular, it can serve as a light emitting host, preferably a green host can do. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

Hereinafter, the present invention will be described more specifically.

One aspect of the present invention relates to an anthracene derivative represented by the above formula (1).

The substituent of formula (1) will be described in more detail as follows.

Preferably, in the anthracene derivative represented by the above formula (1), Q may be phenylene, naphthylene or biphenylene.

R1 and R2 are each independently phenyl; 1-naphthyl; 2-naphthyl; Biphenyl; Triphenyl; 1-tetralinyl; 2-tetralinyl; Stilbene; Fluorenyl; Or anthracenyl substituted with diphenyl, biphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, phenyl or naphthyl; Phenyl substituted with a group selected from the group consisting of phenylthiophenyl, carbazolyl and diphenylamine.

X is preferably a C ₆ -C ₂₀ aryl group including 1-naphthyl, 2-naphthyl, biphenyl, or a substituted or unsubstituted C ₅ -C ₂₀ heterocyclic group.

X is preferably selected from the group consisting of the following structural formulas.

In the above formulas, Ar ₁ to Ar ₅ are the same or different from each other, and each independently phenyl; 1-naphthyl; 2-naphthyl; Biphenyl; Triphenyl; 1-tetralinyl; 2-tetralinyl; Stilbene; Fluorenyl; Or anthracenyl substituted with diphenyl, biphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, phenyl or naphthyl; A phenyl group substituted with a group selected from the group consisting of phenylthiophenyl, carbazolyl, and diphenylamine.

In the anthracene derivative, X is preferably represented by the following formula (2).

(2)

In Formula 2, n, p, q and r are 0 or an integer of 1 to 10, p + q? 1,

L ₁ is directly connected; Of _{halogen, CN, NO 2, C 1} ~ C 20 alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₆ ~ C ₂₀ aryl amine group, C ₁ ~ C ₂₀ of the alkylthiophene group, C ₆ ~ aryl T of C ₂₀ thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ aryl of C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ of the group, -BRR ', -SiRR'R ", -GeRR'R " and a substituted or unsubstituted C ₅ ~ C ₂₀ by at least one group selected from the group consisting of heterocyclic ring groups is substituted or unsubstituted C ₅ ~ C ₂₀ of An arylene group; Or a _{halogen, CN, NO 2, C 1} ~ C 20 alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ arylamine group of C ₂₀ alkyl amine _{group, C 6 ~ C 20, C} 1 ~ C 20 A C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₃ -C ₂₀ cycloalkyl group, a C ₆ -C ₂₀ aryl group, -BRR ', -SiRR'R " and, -GeRR'R "and substituted or unsubstituted C ₅ ~ optionally substituted with one or more groups selected from the group consisting of the C ₂₀ heterocyclic or unsubstituted divalent heterocyclic ring in the C ₅ ~ C ₂₀ group,

L ₂ is a C ₅ to C ₂₀ aryl group,

Wherein R, R 'and R "are each independently selected from the group consisting of hydrogen, a C ₁ to C ₂₀ alkyl group, a C ₃ to C ₂₀ cycloalkyl group, a C ₆ to C ₂₀ aryl group or a C ₅ to C ₂₀ heterocyclic ring Lt; / RTI &

R ₇ and R ₈ are the same or different from each other and each independently hydrogen; halogen; Hydroxyl; Mercapto; Cyano; Nitro; Carbonyl; Carboxyl; Formyl; Substituted or unsubstituted C ₁ -C ₂₀ alkyl; Substituted or unsubstituted C ₂ -C ₁₀ alkenyl; Substituted or unsubstituted C ₂ -C ₇ alkynyl; Substituted or unsubstituted C ₆ -C ₂₀ aryl; Substituted or unsubstituted C ₄ -C ₂₀ heteroaryl; Substituted or unsubstituted C ₃ -C ₇ cycloalkyl wherein the carbon atoms in the ring may be optionally replaced by an oxygen, nitrogen or sulfur atom; C ₄ -C ₇ cycloalkenyl wherein the carbon atoms in the ring may be optionally replaced by an oxygen, nitrogen or sulfur atom; Substituted or unsubstituted C ₁ -C ₂₀ alkoxy; Substituted or unsubstituted C ₂ -C ₁₀ alkenyloxy; Substituted or unsubstituted C ₂ -C ₇ alkynyloxy; Substituted or unsubstituted C ₆ -C ₂₀ aryloxy; A substituted or unsubstituted C ₁ -C ₂₀ alkylamine; Substituted or unsubstituted C ₂ -C ₁₀ alkenylamines; Substituted or unsubstituted C ₂ -C ₇ alkynylamines; Substituted or unsubstituted C ₆ -C ₂₀ arylamine; Substituted or unsubstituted C ₇ -C ₂₀ alkyl aryl amines; Substituted or unsubstituted C ₁ -C ₂₀ alkylsilyl; Substituted or unsubstituted C ₂ -C ₁₀ alkenylsilyl; Substituted or unsubstituted C ₂ -C ₇ alkynylsilyl; Substituted or unsubstituted C ₆ -C ₂₀ arylsilyl; Substituted or unsubstituted C ₇ -C ₂₀ alkylaryl silyl; Substituted or unsubstituted C ₁ -C ₂₀ alkylboranyl; Substituted or unsubstituted C ₂ -C ₁₀ alkenylboranyl; Substituted or unsubstituted C ₂ -C ₇ alkynylboranyl; Substituted or unsubstituted C ₆ -C ₂₀ arylboranyl; Substituted or unsubstituted C ₇ -C ₂₀ alkylaryl boranyl; Substituted or unsubstituted C ₁ -C ₂₀ alkylthio; Substituted or unsubstituted C ₂ -C ₁₀ alkenylthio; Substituted or unsubstituted C ₂ -C ₇ alkynylthio; And a substituted or unsubstituted C ₆ -C ₂₀ arylthio group.

Preferably, R ₇ and R ₈ are the same or different and are each independently selected from the group consisting of hydrogen, cyano, nitro, substituted or unsubstituted C ₁ -C ₂₀ alkyl, substituted or unsubstituted C ₂ -C ₁₀ alkenyl, substituted or unsubstituted C ₃ -C ₇ cycloalkyl, substituted or unsubstituted C ₄ -C ₇ cycloalkenyl, substituted or unsubstituted C ₆ -C ₂₀ aryl, substituted or unsubstituted C ₄ -C ₂₀ heteroaryl Substituted or unsubstituted C ₁ -C ₂₀ alkoxy, substituted or unsubstituted C ₆ -C ₂₀ aryloxy, substituted or unsubstituted C ₁ -C ₂₀ Alkylamine, substituted or unsubstituted C ₆ -C ₂₀ arylamine, substituted or unsubstituted C ₇ -C ₂₀ alkylarylamine, substituted or unsubstituted C ₁ -C ₂₀ alkylsilyl; Substituted or unsubstituted C ₁ -C ₂₀ alkylboranyl, substituted or unsubstituted C ₆ -C ₂₀ arylboranyl, substituted or unsubstituted C ₇ -C ₂₀ alkylarylboranyl, substituted or unsubstituted C ₁ -C ₂₀ alkyl Thio, and substituted or unsubstituted C ₆ -C ₂₀ arylthio groups.

As used herein, the term "substituted or unsubstituted" refers to a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a carbazolyl group, An acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, an acyl group, a nitrile group and an acetylene group.

Specific examples of the compound represented by the formula (1) according to the present invention are shown below, but are not limited thereto.

The second aspect of the present invention relates to a process for producing an anthracene derivative represented by the above formula (1).

The method for producing the anthracene derivative includes:

1) reacting 1-chloroanthraquinone with a boronic acid compound (XQB (OH) ₂ ) to prepare a compound (II)

2) reacting the compound (II) with a bromo compound (R1-Br or R2-Br) to prepare a dihalo compound (III)

3) a step of reacting the dihydric alcohol compound (III) with potassium iodide and sodium hypophosphite to prepare the compound (I).

[Reaction Scheme 1]

In the above Reaction Scheme 1, Q, R 1, R 2, and X are the same as defined in Formula 1 above.

The anthracene derivative according to the present invention is described in detail in the following examples. Those skilled in the art will appreciate that the anthracene derivatives represented by formula (1) Can be easily produced.

A third aspect of the present invention relates to an organic electronic device using the compound of formula (1).

The organic electronic device of the present invention can be produced by a conventional method and material for producing an organic electronic device, except that the above-described compounds are used to form one or more organic material layers.

Hereinafter, the organic light emitting device will be described.

The compounds of the present invention can act as hole-injecting, hole-transporting, electron-injecting, electron-transporting or luminescent materials in organic light emitting devices, Together with a luminescent host, or a suitable luminescent host, can serve as a luminescent dopant.

In one 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 interposed therebetween, and the anthracene derivative represented by Formula 1 according to the present invention May be manufactured using a conventional method and materials for producing an organic light emitting device, except that the organic light emitting device is used for at least one layer of the organic material layer of the 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 may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole injection layer, a hole transporting layer, a hole injecting and transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a material which can be used as a cathode is deposited thereon . ≪ / RTI > In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer 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. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material having high mobility to holes is suitable for transporting holes from the anode or the hole injection layer to the light emitting layer. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing 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 front emission type, a back emission type, or a both-sided emission type, depending on 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 electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

Hereinafter, preferred embodiments of the present invention will be described to facilitate understanding of the present invention. The following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

<Examples>

Example  One : Preparation of Compound (1)

1. Preparation of Compound 1-1

1-Chloroanthraquinone (41.2 mmol, 10.0 g) was completely dissolved in 200 mL of THF and 4,4,5,5-tetramethyl-2- (4- (10- phenyl anthrac- ) -1,3,2-dioxaborane (45.3 mmol, 20.6 g), 50 mL of a 2 M solution of potassium carbonate, tetrakis (triphenylphosphine) palladium (0) mmol, 1.43 g) were added and refluxed for 19 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, and washed several times with water and ethanol to obtain Compound 1-1 (21 g, 96%). MS [M] = 536

2. Preparation of Compound 1-2

Bromophenyl (19.1 mmol, 3.0 g) was completely dissolved in 100 mL of dried THF, and n -butyllithium (6.2 mL, 2.5 M solution in hexane) was slowly added thereto at -78 ° C. After 1 hour, the compound 1-1 (9.3 mmol, 5 g) prepared in the above step 1 was added to the above reaction product. After 30 minutes, the cooling vessel was removed and reacted at room temperature for 3 hours. After the reaction was completed, NH ₄ Cl aqueous solution was added thereto, followed by extraction with ethyl ether. The extracted reaction was dried with anhydrous magnesium sulfate and concentrated. A small amount of ethyl ether was added thereto, and the mixture was stirred, and ethanol was added thereto and stirred. Then, the reaction product was filtered and dried to obtain a di-alcohol compound 1-2 (4.74 g, 95%). MS [M] = 518 (- H ₂ O form)

3. Preparation of Compound 1

The compound 1-2 (3.6 g, 6.77 mmol), potassium iodide (1.12 g, 6.77 mmol) and sodium hypophosphite (7.18 g, 67.7 mmol) were refluxed in 100 mL of acetic acid for 3 hours. The reaction product was cooled to room temperature, filtered, washed several times with water and ethanol, and then dried to obtain Compound 1 (2.90 g, 65%). MS [M] = 658

Example  2 : Preparation of compound 4

1. Preparation of Compound 2-1

1-Chloroanthraquinone (41.2 mmol, 10.0 g) was completely dissolved in 200 mL of THF. To this was added 4,4,5,5-tetramethyl-2- (4- (10- (2-naphthyl) (45.3 mmol, 22.9 g), 50 mL of a 2 M solution of potassium carbonate, and tetrakis (triphenylphosphine) palladium (0) 0)] (1.24 mmol, 1.43 g) was added and refluxed for 19 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and washed several times with water and ethanol to obtain Compound 2-1 (23 g, 96%). MS [M] = 586

2. Preparation of Compound 2-2

Bromophenyl (19.1 mmol, 3.0 g) was completely dissolved in 100 mL of dried THF, and n -butyllithium (6.2 mL, 2.5 M solution in hexane) was slowly added thereto at -78 ° C. After 1 hour, the compound 2-1 (9.3 mmol, 5.4 g) prepared in the above 1 was added to the above reaction product. After 30 minutes, the cooling vessel was removed and reacted at room temperature for 3 hours. After the reaction was completed, NH ₄ Cl aqueous solution was added thereto, followed by extraction with ethyl ether. The extracted reaction was dried with anhydrous magnesium sulfate and concentrated. A small amount of ethyl ether was added thereto, and the mixture was stirred, and ethanol was added thereto and stirred. Then, the reaction product was filtered and dried to obtain the diol compound 1-2 (6.56 g, 95%). MS [M] = 724 (- H 2 O form)

3. Preparation of Compound 4

The compound 2-2 (5.0 g, 6.77 mmol), potassium iodide (1.12 g, 6.77 mmol) and sodium hypophosphite (7.18 g, 67.7 mmol) were refluxed in 100 mL of acetic acid for 3 hours. The reaction product was cooled to room temperature, filtered, washed several times with water and ethanol, and then dried to obtain Compound 4 (3.1 g, 65%). MS [M] = 708

Example  3 : Preparation of Compound 10

1. Preparation of Compound 3-1

1-Chloroanthraquinone (41.2 mmol, 10.0 g) was completely dissolved in 200 mL of THF, and 4,4,5,5-tetramethyl-2- (3- (1,8- phenyl) anthrac- (0) [tetrakis (triphenylphosphine) palladium (0)) was added to 50 ml of a 2 M solution of potassium carbonate, ] (1.24 mmol, 1.43 g) was added and the mixture was refluxed for 19 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, and washed several times with water and ethanol to obtain Compound 3-1 (24.2 g, 96%). MS [M] = 612

2. Preparation of compound 3-2

Bromophenyl (19.1 mmol, 3.0 g) was completely dissolved in 100 mL of dried THF, and n -butyllithium (6.2 mL, 2.5 M solution in hexane) was slowly added thereto at -78 ° C. After 1 hour, the compound 3-1 (9.3 mmol, 5.7 g) prepared in the above step 1 was added to the above reaction product. After 30 minutes, the cooling vessel was removed and reacted at room temperature for 3 hours. After the reaction was completed, NH ₄ Cl aqueous solution was added thereto, followed by extraction with ethyl ether. The extracted reaction was dried with anhydrous magnesium sulfate and concentrated. A small amount of ethyl ether was added thereto, and the mixture was stirred, and ethanol was added thereto and stirred. Then, the reaction product was filtered and dried to obtain a dihalo compound 3-2 (6.8 g, 95%). MS [M] = 750 (- H 2 O form)

3. Preparation of Compound 10

The compound 3-2 (3.42 g, 6.77 mmol), potassium iodide (1.12 g, 6.77 mmol) and sodium hypophosphite (7.18 g, 67.7 mmol) were refluxed in 100 mL of acetic acid for 3 hours. The reaction product was cooled to room temperature, filtered, washed several times with water and ethanol, and then dried to obtain Compound 10 (3.2 g, 65%). MS [M] = 734

Example  4 : Preparation of compound 14

1. Preparation of compound 4-1

1-Chloroanthraquinone (41.2 mmol, 10.0 g) was completely dissolved in 200 mL of THF, and 4,4,5,5-tetramethyl-2- (3- (5- phenylthiophen- ) -1,3,2-dioxaborane (45.3 mmol, 21.9 g), 50 mL of a 2 M solution of potassium carbonate, tetrakis (triphenylphosphine) palladium (0) mmol, 1.43 g) were added and refluxed for 19 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, and washed several times with water and ethanol to obtain Compound 4-1 (16.7 g, 96%). MS [M] = 442

2. Preparation of compound 4-2

Bromophenyl (19.1 mmol, 3.0 g) was completely dissolved in 100 mL of dried THF, and n -butyllithium (6.2 mL, 2.5 M solution in hexane) was slowly added thereto at -78 ° C. After 1 hour, the compound 4-1 (9.3 mmol, 4.1 g) prepared in the above 1 was added to the above reaction product. After 30 minutes, the cooling vessel was removed and reacted at room temperature for 3 hours. After the reaction was completed, NH ₄ Cl aqueous solution was added thereto, followed by extraction with ethyl ether. The extracted reaction was dried with anhydrous magnesium sulfate and concentrated. A small amount of ethyl ether was added thereto, and the mixture was stirred, and ethanol was added thereto and stirred. Then, the reaction product was filtered and dried to obtain the diol compound 4-2 (5.3 g, 95%). MS [M] = 580 (- H 2 O form)

3. Preparation of compound 14

The compound 4-2 (4.05 g, 6.77 mmol), potassium iodide (1.12 g, 6.77 mmol) and sodium hypophosphite (7.18 g, 67.7 mmol) were refluxed in 100 mL of acetic acid for 3 hours. The reaction product was cooled to room temperature, filtered, washed several times with water and ethanol, and then dried to obtain Compound 14 (2.5 g, 65%). MS [M] = 564

Experimental Example  One

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) thin film with a thickness of 1000 Å was immersed in distilled water containing dissolved dispersant and ultrasonically cleaned. The dispersing agent was a product of Fischer Co., and distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, the substrate was ultrasonically cleaned in the order of isopropyl alcohol, acetone, and methanol solvent, dried, and transported by a plasma cleaner. The substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

N, N'-bis (2-naphthylphenyl) aminophenyl] carbazole (800 Å), 4,4'-bis [N- (NPB) (300 ANGSTROM), compounds 1, 4, 10 and 14 (300 ANGSTROM) prepared in Examples 1 to 4, and 9,10-bis (300 ANGSTROM) were sequentially deposited by thermal vacuum deposition to form a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer in this order.

In the light emitting layer, the following amine compound D1 was used as a dopant material.

Comparative Example  1 to 3

An organic light emitting device was prepared in the same manner as in Experimental Example 1 except that the following compounds A, B, and C were used instead of the compounds 1, 4, 10, and 14 in Experimental Example 1.

The light emitting layer materials and experimental results used in the Experimental Examples and Comparative Examples are summarized in Table 1 below.

[Table 1]

The compounds of formula (I) according to the present invention appear to have two fluorescent chromophores in one molecule due to the presence of two or more fluorescent chromophores, that is, Q linked to anthracene and X. In particular, when an anthracene moiety and X are chemically bonded to each other when they are at an ortho or meta position other than a para position, they do not greatly affect conjugation with each other, Lt; / RTI &gt; Therefore, a molecular structure that can contain two carriers per molecule can be expected to increase the efficiency.

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

Claims (14)

An anthracene derivative represented by the following Formula 1: [Chemical Formula 1]

In Formula 1, Q is a phenylene group, R1 and R2 are each independently an aryl group of C ₆ ~ C _20, X is a heterocyclic group of C ₅ ~ C ₂₀ substituted with a C ₆ ~ C ₂₀ aryl group. delete 3. The compound of claim 1, wherein R1 and R2 are each independently selected from the group consisting of phenyl; 1-naphthyl; 2-naphthyl; Biphenyl; Triphenyl; Stilbene; Or an anthracene derivative, characterized in that it is fluorenyl. delete delete delete delete The anthracene derivative according to claim 1, wherein the compound of formula (1) is selected from the group consisting of the following structural formulas: [Compound 14]

[Compound 15]

1) reacting 1-chloroanthraquinone with a boronic acid compound (XQB (OH) ₂ ) to prepare a compound (II) 2) reacting the compound (II) with a bromo compound (R1-Br or R2-Br) to prepare a dihalo compound (III) 3) reacting the dialcohol compound (III) with potassium iodide and sodium hypophosphite to prepare a compound (I) A process for producing an anthracene derivative represented by the following Reaction Scheme 1: [Reaction Scheme 1]

In the above Reaction Scheme 1, Q is a phenylene group, R1 and R2 are each independently an aryl group of C ₆ ~ C _20, X is a heterocyclic group of C ₅ ~ C ₂₀ substituted with a C ₆ ~ C ₂₀ aryl group. 1. An organic electronic 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 represented by formula 1 shown in claim 1 or 3 &Lt; / RTI &gt; wherein the anthracene derivative comprises an anthracene derivative. [Claim 11] The organic electroluminescent device according to claim 10, wherein the organic layer includes at least one of a hole injection layer, a hole transport layer, and a layer simultaneously injecting holes and transporting holes, wherein one of the layers is an anthracene derivative represented by Formula 1 &Lt; / RTI &gt; The organic electronic device according to claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises an anthracene derivative represented by the general formula (1). The organic electronic device according to claim 10, wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises an anthracene derivative represented by the above formula (1). 11. The organic electronic device according to claim 10, 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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