KR101405736B1 - New anthracene derivatives and organic electronic device using the same - Google Patents

Abstract

The present invention relates to a novel anthracene derivative and an organic electronic device using the same. The anthracene derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting and transporting, or light emitting material in an organic electronic device including an organic light emitting device. The anthracene derivative according to the present invention can serve as a luminescent host in an organic electronic device alone, and in particular, can serve as a blue host, and is used as a luminescent host in a luminescent layer, thereby exhibiting excellent characteristics in terms of efficiency, driving voltage and stability .

An anthracene derivative, a light emitting layer, an organic electronic device,

Description

TECHNICAL FIELD [0001] The present invention relates to a novel anthracene derivative and an organic electronic device using the same.

The present invention relates to a novel anthracene derivative 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 / or electrons into an organic semiconductor that interfaces with an electrode by applying a 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), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. 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 can be classified into 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 yet been sufficiently developed. 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.

Accordingly, the present inventors synthesized novel anthracene derivatives. As a result, it has been found that compounds can be used as a light emitting host in hole injection, hole transport, electron injection and transport, or as a light emitting material in an organic electronic device, And that the stability-enhancing effect is excellent, and the present invention has been completed.

Accordingly, it is an object of the present invention 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 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 a novel An organic electronic device comprising an anthracene derivative is provided.

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

The novel anthracene derivative of the present invention includes a compound represented by the following general formula (1).

In Formula 1,

n is an integer of 1 to 5,

Ar1 and Ar2 are the same or different and independently represent hydrogen; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ the aryl group, C ₅ ~ C ₂₀ heteroaryl group, an arylamine group, heavy hydrogen, -SiRR'R "and -GeRR'R" C ₁ ~ by at least one group selected from the group consisting of a substituted or unsubstituted C ₂₀ of An alkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ A substituted or unsubstituted C ₂ to C ₂₀ aryl group, a substituted or unsubstituted aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" An alkenyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ A substituted or unsubstituted C ₂ to C ₂₀ aryl group, a substituted or unsubstituted aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" An alkynyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A cycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A heterocycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ Substituted or unsubstituted C ₆ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R "and -GeRR'R" An aryl group; And C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C of the ₂₀ aryl group, C ₅ ~ C ₂₀ heteroaryl group, an arylamine group, heavy hydrogen, -SiRR'R "and -GeRR'R" a C ₅ ~ C ₂₀ substituted or unsubstituted by at least one group selected from the group consisting of -R ', -R''are each independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group.

In addition, the novel anthracene derivatives of the present invention include compounds represented by the following general formula (2).

In Formula 2,

n is an integer of 1 to 5,

Ar 3 to Ar 6 are the same or different and independently represent hydrogen, a C ₁ to C ₂₀ alkyl group, 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 Selected from the group consisting of a C ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" with at least one substituted or unsubstituted C ₁ ~ C ₂₀ alkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ Substituted or unsubstituted C ₂ -C ₂₀ aryl group, C ₅ -C ₂₀ heteroaryl group, arylamine group, deuterium, -SiRR'R ", and -GeRR'R" An alkenyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ A substituted or unsubstituted C ₂ to C ₂₀ aryl group, a substituted or unsubstituted aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" An alkynyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A cycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A heterocycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ Substituted or unsubstituted C ₆ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R "and -GeRR'R" An aryl group; And C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C of the ₂₀ aryl group, C ₅ ~ C ₂₀ heteroaryl group, an arylamine group, heavy hydrogen, -SiRR'R "and -GeRR'R" a C ₅ ~ C ₂₀ substituted or unsubstituted by at least one group selected from the group consisting of R 2, R 3 and R 4 are each independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group.

The novel anthracene derivatives of the present invention include compounds represented by the following general formula (3).

In the above formula (3)

n is an integer of 1 to 5,

Ar7 to Ar9 are the same or different and are different and independently represent hydrogen; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ the aryl group, C ₅ ~ C ₂₀ heteroaryl group, an arylamine group, heavy hydrogen, -SiRR'R "and -GeRR'R" C ₁ ~ by at least one group selected from the group consisting of a substituted or unsubstituted C ₂₀ of An alkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ A substituted or unsubstituted C ₂ to C ₂₀ aryl group, a substituted or unsubstituted aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" An alkenyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ A substituted or unsubstituted C ₂ to C ₂₀ aryl group, a substituted or unsubstituted aryl group, a C ₅ to C ₂₀ heteroaryl group, an arylamine group, a deuterium, -SiRR'R "and -GeRR'R" An alkynyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A cycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ C ₃ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R ", and -GeRR'R" A heterocycloalkyl group; A C ₂ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ Substituted or unsubstituted C ₆ to C ₂₀ substituted or unsubstituted aryl groups, C ₅ to C ₂₀ heteroaryl groups, arylamine groups, deuterium, -SiRR'R "and -GeRR'R" An aryl group; And C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C of the ₂₀ aryl group, C ₅ ~ C ₂₀ heteroaryl group, an arylamine group, heavy hydrogen, -SiRR'R "and -GeRR'R" a C ₅ ~ C ₂₀ substituted or unsubstituted by at least one group selected from the group consisting of R 2, R 3 and R 4 are each independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group.

In the general formulas (1) to (3), Ar 1 to Ar 9 are preferably each independently aryl such as phenyl, biphenyl and naphthyl; An arylamine group; A condensed ring group of an aliphatic ring and an aromatic ring; An aryl group substituted with a heteroaryl group; Carbazole substituted aryl; An arylamine group substituted with at least one group selected from -SiRR'R "and -GeRR'R"; And aryl substituted with an arylamine group substituted or unsubstituted with -SiRR'R "or -GeRR'R".

The definition of the above-mentioned substituent will be described in detail as follows.

"Alkyl" means a straight or branched saturated monovalent hydrocarbon moiety of 1 to 20, preferably 1 to 10, more preferably 1 to 6 carbon atoms. The alkyl group may be optionally substituted by one or more halogen substituents. Examples of alkyl groups include methyl, ethyl, propyl, 2-propyl, n-butyl, iso-butyl, tert- butyl, pentyl, hexyl, dodecyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, But are not limited to, dichloromethyl, trichloromethyl, iodomethyl, bromomethyl and the like.

"Alkenyl" means a straight or branched chain monovalent hydrocarbon moiety of 2 to 20, preferably 2 to 10, more preferably 2 to 6 carbon atoms comprising at least one carbon-carbon double bond . The alkenyl group may be bonded through a carbon atom containing a carbon-carbon double bond or through a saturated carbon atom. The alkenyl group may be optionally substituted by one or more halogen substituents. Examples of the alkenyl group include but are not limited to ethenyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, pentenyl, 5-hexenyl and dodecenyl.

"Alkynyl" refers to a straight or branched chain monovalent hydrocarbon moiety of from 2 to 20 carbon atoms, preferably from 2 to 10, more preferably from 2 to 6 carbon atoms comprising at least one carbon-carbon triple bond do. Alkynyl groups may be bonded through a carbon atom comprising a carbon-carbon triple bond or through a saturated carbon atom. The alkynyl group may be optionally substituted by one or more halogen substituents. For example, ethynyl and propynyl, but are not limited thereto.

"Cycloalkyl" means a saturated or unsaturated nonaromatic monovalent monocyclic, bicyclic or tricyclic hydrocarbon moiety of 3 to 12 ring carbons, optionally substituted with one or more halogen substituents. (E.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cyclooctyl, decahydronaphthalenyl, adamantyl, norbonyl Hept-5-enyl), and the like, but are not limited thereto.

"Aryl" means a monovalent monocyclic, bicyclic, or tricyclic aromatic hydrocarbon moiety having 6 to 20, preferably 6 to 12, ring atoms, optionally substituted with one or more halogen substituents, and the like . Examples of the aryl group include, but are not limited to, phenyl, anthracenyl, biphenyl, pyrenyl, naphthalenyl, fluorenyl, derivatives thereof and the like.

Examples of the heteroaryl group include, but are not limited to, a substituted or unsubstituted pyridyl group, a bipyridyl group, a quinolyl group, and an isoquinolyl group.

The compound represented by Formula 1 is preferably an anthracene derivative selected from Compounds 1-1 to 1-54 of Table 1 below.

The compound represented by Formula 2 is preferably an anthracene derivative selected from the compounds 2-1 to 2-12 of Table 2 below.

In addition, the compound represented by Formula 3 is preferably an anthracene derivative selected from Compounds 3-1 to 3-10 of Table 3 below.

The present invention also provides a process for preparing anthracene derivatives represented by the above general formulas (1), (2) and (3).

The anthracene derivative according to the present invention can be prepared by Suzuki coupling reaction of a dibromoaryl compound and an anthracene boronic acid compound under a palladium catalyst. Specific production methods are described in the following Production Examples.

The present invention also provides an organic electronic device using the compounds represented by Formulas (1), (2) and (3).

The organic electronic device of the present invention can be produced by a conventional method and materials for producing an organic electronic device, except that an anthracene derivative of the present invention is used to form one or more organic layers.

Hereinafter, an organic light emitting device using the anthracene derivative of the present invention will be exemplified.

The anthracene derivative can act as a luminescent material, in particular, as a hole injecting, a hole transporting, an electron injecting and transporting, or a luminescent material in an organic luminescent device. In addition to a suitable luminescent dopant, It can serve as a luminescent dopant with the host.

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 layer disposed therebetween. The organic layer in the organic light emitting device of the present invention may have a single layer structure of one layer or a multilayer structure of two or more layers including a light emitting layer. When the organic material layer of the organic light emitting diode of the present invention has a multilayer structure, it may have a structure in which, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are stacked.

However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers. For example, the organic light emitting device of the present invention may have a structure as shown in FIG. 1, reference numeral 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injecting layer, 4 denotes a hole transporting layer, 5 denotes an organic light emitting layer, 6 denotes an electron transporting layer and 7 denotes a cathode. The organic light emitting device having the structure as shown in FIG. 1 is generally referred to as an organic light emitting device having a normal structure. However, the present invention is not limited to this 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 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.

In the case where the organic light emitting device according to the present invention has a multilayer organic material layer, the compounds of the above Chemical Formulas 1 to 3 may be used for a light emitting layer, a hole injecting layer, a hole transporting layer, a layer for simultaneously transporting and emitting light, Layer, an electron transport layer, an electron transport layer, and / or an injection layer. In the present invention, it is particularly preferable that the compound represented by Chemical Formula 1, Chemical Formula 2 or Chemical Formula 3 is included in the light emitting layer.

The organic electroluminescent device according to the present invention can be produced by a conventional method for producing an organic electroluminescent device and a method for producing the same using an anthracene derivative represented by the general formula (1), (2) or (3) . ≪ / RTI > 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, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate in order to fabricate an organic light emitting device having a reverse structure as described above.

The organic material layer may be formed by using a variety of polymer materials in a smaller number of layers by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process, Can be manufactured.

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-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. 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 in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited thereto.

The compounds of formulas (1), (2) and (3) according to the present invention can be prepared by a multistage chemical reaction. The preparation of these compounds is described by the following examples. As shown in the examples, some of the intermediate compounds are first prepared, and the compounds of the formulas (1), (2) and (3) are prepared from the intermediate compounds. Illustrative intermediate compounds are the following compounds A-K. In these compounds, "Br" may be substituted with any other reactive atom or functional group.

[Chemical A] [Compound B] [Compound C] [Compound D] [Compound E]

[Chemical F] [Compound G] [Compound H] [Compound I]

[Chemical J] [Compound K]

Compounds having substituents in the parentheses were prepared in the same manner as in Preparation Example of Compound A to Compound K, and the final compounds were synthesized using the compounds.

PREPARATION EXAMPLE 1 Preparation of Compound A

It was dissolved in 9-bromo-10- (2-naphthyl) anthracene (10 g, 26 mmol) and 4-bromo-benzene-boronic acid (4.7 g, 23.5 mmol) to THF (150 ㎖) under nitrogen atmosphere, K ₂ CO ₃ (7 g, 52 mmol) was dissolved in H ₂ O (50 mL) and Pd (PPh ₃ ) ₄ (0.6 g, 0.52 mmol) was added thereto and the mixture was refluxed for about 17 hours. After completion of the reaction, 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 redissolved in THF, purified by column chromatography, and recrystallized from THF and ethanol to obtain Compound A (4.8 g, 40%). MS [M + H] < + > = 459

PREPARATION EXAMPLE 2 Preparation of Compound B

Compound B (4.0 g, 40%) was prepared in the same manner as in Production Example 1, except that 3-bromobenzeneboronic acid was used in place of 4-bromobenzeneboronic acid in Preparation Example 1. MS [M + H] < + > = 459

PREPARATION EXAMPLE 3 Preparation of Compound C

(4.8 g, 10.5 mmol), bis (pinacolato) diboron (3.19 g, 12.5 mmol), potassium acetate (4.12 g, 42 mmol) and palladium (diphenylphosphinoferrocene) chloride 0.26 g, 3 mol%) was placed in a 250 ml flask, and dioxane (50 ml) was added thereto, followed by reflux at 100 ° C for 12 hours. The reaction solution was cooled to room temperature, distilled water (50 ml) was added, and the mixture was extracted with methylene chloride (50 ml × 3). The methylene chloride was removed under reduced pressure to give a pale yellow solid. The pale yellow solid was washed with ethanol and dried to obtain Compound C (5.5 g, 95%).

PREPARATION EXAMPLE 4 Preparation of Compound (D)

Compound D (5.5 g, 95%) was obtained in the same manner as in Production Example 3, except that Compound B prepared in Preparation Example 2 was used instead of Compound A in Preparation Example 3.

PREPARATION EXAMPLE 5 Preparation of Compound E

(18 g, 80.0 mmol) and t-butylnitrite (12 mL, 101 mmol) were dispersed and stirred in acetonitrile (250 mL) at 65 ° C, 2-aminoanthraquinone (15 g, 67.2 mmol) Was slowly added dropwise over 5 minutes. When gas evolution was completed, the reaction solution was cooled to room temperature and the reaction solution was added to a 20% aqueous hydrochloric acid solution (1 L) and extracted with dichloromethane. The residual moisture of the organic layer was removed with anhydrous magnesium sulfate, and the organic layer was dried under reduced pressure. Separation by column chromatography gave compound E (14.5 g, 75%) as pale yellow.

PREPARATION EXAMPLE 6 Preparation of Compound F

2-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in THF (100 mL) dried under a nitrogen atmosphere and t-butyllithium (46.8 mL, 1.7 M pentane solution) was added slowly at -78 deg. After stirring for a period of time, the compound E (6.36 g, 22.0 mmol) prepared in Preparation Example 5 was added. After the cooling vessel was removed, the mixture was stirred at room temperature for 3 hours. 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, petroleum ether was added, and the mixture was stirred for several hours to obtain a solid compound. The solid compound was filtered and vacuum dried to obtain Compound F (11.2 g, 93%).

PREPARATION EXAMPLE 7 Preparation of Compound G

The compound F (11.2 g, 20.5 mmol) prepared in Preparative Example 6 was dispersed in acetic acid (200 mL) under nitrogen atmosphere and potassium iodine (34 g, 210 mmol) and sodium hypophosphite hydrate (37 g, Followed by boiling and stirring for 3 hours. After cooling at room temperature, the mixture was filtered, washed with water and methanol, and vacuum dried to obtain light yellow compound G (7.2 g, 64%). MS [M] = 509

PREPARATION EXAMPLE 8 Preparation of Compound H

Compound H (4.0 g, 40%) was obtained in the same manner as in Production Example 1, except that Compound G was used instead of 9-bromo-10- (2-naphthyl) anthracene in Preparation Example 1 . MS [M + H] < + > = 585

PREPARATION EXAMPLE 9 Preparation of Compound (I)

Compound I (5.5 g, 95%) was obtained in the same manner as in Production Example 3, except that Compound H prepared in Preparation Example 8 was used instead of Compound A in Production Example 3.

PREPARATION EXAMPLE 10 Preparation of Compound J

(10 g, 16 mmol) and 2-thiophene boronic acid (2.2 g, 17.4 mmol) were dissolved in THF (150 mL) under nitrogen atmosphere, and K ₂ CO ₃ (6.5 g, 48 mmol) was dissolved in H ₂ O (50 mL). Finally, Pd (PPh ₃ ) ₄ (0.5 g, 0.48 mmol) was added and the mixture was refluxed for about 17 hours. After completion of the reaction, 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 redissolved in THF, purified by column chromatography, and recrystallized from THF and ethanol to obtain yellow compound J (7.0 g, 75%). MS [M + H] < + > = 588

PREPARATION EXAMPLE 11 Preparation of Compound K

Compound J (7 g, 11.9 mmol) prepared in Preparation Example 10 was dissolved in chloroform, N-bromosuccinimide (2.3 g, 13 mmol) was added thereto, and the mixture was stirred for 3 hours. The resulting precipitate was filtered off under reduced pressure, and then dissolved in THF and recrystallized with ether to obtain Compound K (7.1 g, 90%). MS [M + H] < + > = 667

Example 1 Preparation of Compound 1-2

Under N ₂ gas flow, 2,6-dibromo-thiophene (1 g, 4.1 mmol), the compound prepared in Preparative Example 3 C (4.4 g, 8.7 mmol ), and _{Pd (PPh 3) 4 (0.2} g, 0.18 mmol) was added to a 2M aqueous K ₂ CO ₃ solution (100 mL) and THF (100 mL), and the mixture was stirred under reflux for about 6 hours. After completion of the reaction, 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 obtain Compound 1-2 (2.86 g, 83%). MS [M] = 841

Example 2 Preparation of Compound 1-3

In the preparation of Formulas 1-2 of Example 1, the same procedure as in the preparation of Formulas 1-2 of Example 1 was repeated except that the compound obtained by introducing the 1-naphthyl group instead of the compound C prepared in Preparation Example 3 was used. (4.2 g, 82%) was obtained in the same manner. MS [M + H] < + > = 841

≪ Example 3 > Preparation of Compound 1-10

The preparation of Formulas 1-2 of Example 1 was repeated except that the compound D prepared in Preparation Example 4 was used instead of the compound C prepared in Preparation Example 3, To obtain the compound of formula 1-10 (4.2 g, 82%). MS [M + H] < + > = 841

Example 4 Preparation of Compound 1-11

In the preparation of Formulas 1-2 of Example 3, the same procedure as in the preparation of Formulas 1-10 of Example 3 was repeated except that the compound obtained by Preparative Example 3 was used in place of the compound 1-naphthyl group (4.2 g, 82%) was obtained in the same manner. MS [M + H] < + > = 841

≪ Example 5 > Preparation of compound 2-2

Under N ₂ gas flow, 2,6-dibromo-thiophene (1 g, 4.1 mmol), prepared in Preparation 9 Compound I (5.5 g, 8.7 mmol) , and _{Pd (PPh 3) 4 (0.2} g, 0.18 mmol) was added to a 2M aqueous K ₂ CO ₃ solution (100 mL) and THF (100 mL), and the mixture was stirred under reflux for about 6 hours. After completion of the reaction, 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 obtain Compound 2 (2.86 g, 83%). MS [M] = 1093

Example 6 Preparation of Compound 3-3

N under a _second air stream, the compound I, prepared in example 11 (2 g, 2.9 mmol) , the compound prepared in Preparative Example 3 C (1.6 g, 3.19 mmol ), Pd (PPh 3) 4 (0.1 g, 0.09 mmol) were added to a 2M aqueous K ₂ CO ₃ solution (100 mL) and THF (100 mL), and the mixture was refluxed and stirred for about 6 hours. After completion of the reaction, 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 obtain Compound 3-3 (2.6 g, 95%). MS [M] = 967

<Experimental Example 1>

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 detergent was a product of Fischer Co. The 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, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

N, N'-bis (2-naphthylphenyl) aminophenyl] carbazole (800 Å), 4,4'-bis [N- (NPB) (300 ANGSTROM), the host material (300 ANGSTROM) and 9,10-bis-2-naphthyl-2- [4- (N Phenylbenzoimidazoyl) phenyl] anthracene (300 Å) 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. As the dopant material in the light emitting layer, a styrylamine compound D1 or D2 represented by the following formula was used as shown in Table 4 below. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

&Lt; Comparative Experimental Example &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compounds were used instead of the compounds prepared in Examples 1 to 6 in Experimental Example 1.

Comparative compound

When a forward electric field of 6 V was applied to the organic light emitting device manufactured according to Experimental Example 1, blue light corresponding to 1700 nit was observed, and the organic light emitting device manufactured according to Experimental Example 1 and Comparative Experimental Example 1 Are shown in Table 5 below. &Lt; tb &gt; &lt; TABLE &gt;

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

DESCRIPTION OF THE REFERENCE NUMERALS

1. Substrate 2. Anode

3. Hole injection layer 4. Hole transfer layer

5. Organic luminescent layer 6. Electron transport layer

7. Cathode

Claims (16)

An anthracene derivative represented by the following Formula 1: &Lt; Formula 1 >

In Formula 1, n is an integer of 1 to 5, Ar 1 and Ar 2 are the same or different and are each independently a C ₆ to C ₂₀ aryl group; An arylamine group of C ₆ to C ₂₀ ; A condensed ring group of an aliphatic ring and an aromatic ring; A C ₆ -C ₂₀ aryl group substituted with a heteroaryl group; A C ₆ to C ₂₀ aryl group substituted with a carbazole; A C ₆ -C ₂₀ arylamine group substituted with at least one group selected from -SiRR'R "and -GeRR'R"; And -SiRR'R "or -GeRR'R" as one selected from an aryl group of a C ₆ ~ C ₂₀ substituted with a substituted or unsubstituted arylamine group, and Each of -R, -R, and -R "is independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group. delete The anthracene derivative according to claim 1, wherein the compound represented by Formula 1 comprises the compound 1-1 to 1-52 of Table 1 below: [Table 1]

An anthracene derivative represented by the following formula 2: (2)

In Formula 2, n is an integer of 1 to 5, Ar 3 to Ar ₆ are the same or different and are each independently a C ₆ to C ₂₀ aryl group; An arylamine group of C ₆ to C ₂₀ ; A condensed ring group of an aliphatic ring and an aromatic ring; A C ₆ -C ₂₀ aryl group substituted with a heteroaryl group; A C ₆ to C ₂₀ aryl group substituted with a carbazole; A C ₆ -C ₂₀ arylamine group substituted with at least one group selected from -SiRR'R "and -GeRR'R"; And -SiRR'R "or -GeRR'R" as one selected from an aryl group of a C ₆ ~ C ₂₀ substituted with a substituted or unsubstituted arylamine group, and Each of -R, -R, and -R "is independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group. delete The anthracene derivative according to claim 4, wherein the compound represented by Formula 2 comprises the compounds 2-1 to 2-10 of Table 2 below: [Table 2]

An anthracene derivative represented by the following formula (3): (3)

In the above formula (3) n is an integer of 1 to 5, Ar7 to Ar9 are the same or different and each independently represents a C ₆ to C ₂₀ aryl group; An arylamine group of C ₆ to C ₂₀ ; A condensed ring group of an aliphatic ring and an aromatic ring; A C ₆ -C ₂₀ aryl group substituted with a heteroaryl group; A C ₆ to C ₂₀ aryl group substituted with a carbazole; A C ₆ -C ₂₀ arylamine group substituted with at least one group selected from -SiRR'R "and -GeRR'R"; And -SiRR'R "or -GeRR'R" as one selected from an aryl group of a C ₆ ~ C ₂₀ substituted with a substituted or unsubstituted arylamine group, and Each of -R, -R, and -R "is independently selected from the group consisting of a C ₁ to C ₂₀ alkyl group, 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 ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₂₀ aryl group, and a C ₅ to C ₂₀ heteroaryl group. delete The anthracene derivative according to claim 7, wherein the compound represented by the formula (3) comprises the compounds 3-1 to 3-10 shown in the following Table 3: [Table 3]

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 formed by the method according to any one of claims 1, 3, 4, 6, 7 And an anthracene derivative of any one of &lt; RTI ID = 0.0 &gt; 9. &Lt; / RTI &gt; 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) drum, and an organic transistor. 12. The organic electronic device according to claim 11, wherein the organic light emitting device is an organic light emitting device having a forward structure in which an anode, one or more organic layers and a cathode are sequentially stacked on a substrate. [Claim 12] The organic electronic device of claim 11, wherein the organic light emitting device is an organic light emitting device having a reverse structure in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate. [Claim 12] The organic electronic device according to claim 11, wherein the organic light emitting element includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the anthracene derivative. The organic electronic device according to claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the anthracene derivative. 11. The organic electronic device according to claim 10, wherein the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron transporting layer comprises the anthracene derivative.

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