JPH09111234A - Organic electroluminescent element material and organic electroluminescent element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject material with a specific metal complex as constituent, having high luminescence intensity, luminescent efficiency and electron transferability, having high electron injectability from cathode, thus easy to make elements and useful for e.g. large-area and full-color display elements excellent in heat resistance and reliability. SOLUTION: This material consists of a metal complex with structure of the formula [X is N or CH; R<1> -R<8> are each H, a halogen, (substituted) alkyl(thio), (substituted) aryl(oxy), (substituted) alkoxy, (substituted) aryl(thio), (mono- or di-substituted) amino, OH, siloxy, acyl, carbamoyl, carboxylic acid group, sulfonic acid group, alicyclic group, carbocyclic aromatic group or heterocyclic group; M is a metal such as group II metal; (n) is 1-3], and is obtained, for example, by complex-forming reaction between a compound of formula II and the corresponding metal compound.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence (EL) element used for a flat light source or a display, and more particularly to a high brightness optical element.

[0002]

2. Description of the Related Art An EL device using an organic substance is expected to be used as an inexpensive, large-area, full-color display device of a solid light emitting type, and many developments have been made. Generally EL
Is composed of a light-emitting layer and a pair of opposed electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons are recombined with holes in the light emitting layer, and energy is emitted as light when the energy level returns from the conduction band to the valence band.

[0003] Conventional organic EL elements are compared with inorganic EL elements.
In all, the driving voltage was high, and the light emission luminance and light emission efficiency were low.
In addition, the characteristic deterioration was remarkable, and it had not been put to practical use.
Recently, high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less
EL layered with organic compound-containing thin film
Devices have been reported and are of interest (Applied Field
Zix Letters, 51, 913, 1987
reference). In this method, the metal chelate complex is converted into a phosphor layer,
Amine-based compounds are used for the hole injection layer to create
Light emission was obtained, and the luminance was 1000 at a DC voltage of 6 to 7 V.
cd / m ^TwoAchieves maximum luminous efficiency of 1.5lm / W
It has performance close to the practical range. However,
Organic EL devices up to now have improved emission
Has been improved, but does not yet have sufficient emission brightness.
No.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide an organic electroluminescent device having a high emission luminance and excellent stability when used repeatedly.
L element. As a result of intensive studies by the present inventors,
It has been found that an organic EL device using at least one layer of an organic EL device material of the compound represented by the general formula [1] has high emission luminance and excellent stability upon repeated use, and has led to the present invention. .

[0005]

That is, the present invention relates to an organic electroluminescent element material represented by the following general formula [1].

General formula [1]

Embedded image [In the formula, X represents N or CH, and R ¹ to R ⁸
Are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted An alkylthio group, a substituted or unsubstituted arylthio group, an amino group, a mono- or di-substituted amino group, a hydroxyl group, a siloxy group, an acyl group, a carbamoyl group, a carboxylic acid group,
A sulfonic acid group, an aliphatic ring group, a carbocyclic aromatic group or a heterocyclic group is shown. M represents a metal. n represents an integer of 1 to 3. ]

Furthermore, the present invention is an organic electroluminescent device comprising a light emitting layer or an organic compound thin film layer including a light emitting layer between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material. It is an organic electroluminescence device.

Furthermore, the present invention provides an organic electroluminescent device comprising a plurality of organic compound thin film layers including a light emitting layer between a pair of electrodes, wherein the organic electroluminescent device material is contained between the light emitting layer and the cathode. It is an organic electroluminescent element formed by forming a layer.

Further, the present invention is the above organic electroluminescent device, wherein a layer containing a triphenylamine derivative is formed between the light emitting layer and the cathode.

BEST MODE FOR CARRYING OUT THE INVENTION

The metal complex of the present invention has a strong property as an n-type semiconductor and has a large electron transporting ability. Furthermore, since the energy generated during the formation of the complex is low, the bond between the metal and the ligand of the formed metal complex is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.

Specific examples of the substituents R ¹ to R ⁸ of the ligand of the general formula [1] are chlorine, bromine, iodine, a halogen atom of fluorine, a methyl group, an ethyl group, a propyl group and a butyl group. Group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, substituted or unsubstituted alkyl group such as trichloromethyl group, phenyl group, naphthyl group, 3-methylphenyl group, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3
-Substituted or unsubstituted aryl groups such as trifluoromethylphenyl group and 3-nitrophenyl group, methoxy group,
n-butoxy group, tert-butoxy group, trichloromethoxy group, trifluoroethoxy group, pentafluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group, 1,1,1,3,3,3-hexa Fluoro-2-
Substituted or unsubstituted alkoxy group such as propoxy group, 6- (perfluoroethyl) hexyloxy group, phenoxy group, p-nitrophenoxy group, p-tert-butylphenoxy group, 3-fluorophenoxy group, pentafluorophenyl group A substituted or unsubstituted aryloxy group such as 3-trifluoromethylphenoxy group, a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, a substituted or unsubstituted alkylthio group such as a trifluoromethylthio group, A substituted or unsubstituted arylthio group such as phenylthio group, p-nitrophenylthio group, p-tert-butylphenylthio group, 3-fluorophenylthio group, pentafluorophenylthio group, 3-trifluoromethylphenylthio group, Cyano group B group, amino group, methylamino group,
Mono- or di-substituted amino groups such as diethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group, bis (acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bisacetoxypropyl ) Amino group, acylamino group such as bis (acetoxybutyl) amino group, hydroxyl group, siloxy group, acyl group, methylcarbamoyl group, dimethylcarbamoyl group, ethylcarbamoyl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, phenyl Carbamoyl group such as carbamoyl group, carboxylic acid group, sulfonic acid group, imide group, cyclopentane group, aliphatic ring group such as cyclohexyl group, carbocyclic aromatic group such as phenyl group, naphthyl group and biphenyl group, pyridine group , Pi Heterocyclic aromatic groups such as gin group, pyrimidine group, pyridazine group, triazine group, indole group, quinoline group, acridine group, etc., heterocyclic groups such as pyrrolidine group, dioxane group, piperidine group, morpholine group, piperazine group and trithian group There are ring groups, etc.

In the above general formula [1], M is
Beryllium, zinc, cadmium, aluminum, gallium, indium, yttrium, scandium, magnesium, calcium, strontium, cobalt, iron,
Copper or nickel is shown, but not limited to. Of these, Group II metals are particularly preferable. n varies depending on the valence of the metal atom, and is 2 in the case of a divalent metal atom and 3 in the case of a trivalent metal atom.

When the metal complex compound of the present invention is used in an organic EL device, it has a high luminous efficiency, a high electron transporting property, and a high electron injecting property from the cathode. is there. Furthermore, since it has a melting point of 300 ° C. or higher, it has excellent heat resistance.

An example of the method for synthesizing the compound represented by the general formula [1] of the present invention is shown below. The metal complex represented by the general formula [1] is synthesized by a complex forming reaction between a corresponding metal compound and a compound represented by the following general formula [2]. General formula [2]

Embedded image

Examples of the metal compound which forms a complex with the compound represented by the general formula [2] include halide salts such as chlorides and bromides, sulfates, nitrates, metal alkoxides such as ethoxy metal and isopropoxide metal. , Or a metal compound partially substituted with acetylacetonate. A metal alkoxide is preferable in the synthesis from the viewpoint of reactivity and safety, but the synthesis is not limited thereto.

The solvent used in the synthesis is methanol, ethanol, chloroform, isopropyl alcohol, ethyl acetate, acetonitrile, 1,4-dioxane, tetrahydrofuran, benzene, toluene, xylene, n-hexane, dimethylformamide, quinoline, sulfolane,
It is selected from water etc. The reaction temperature is determined by the metal complex formation rate of the ligand. It is preferably 0 to 250 ° C, more preferably 20 to 80 ° C. The reaction is performed for 10 minutes to 24 hours. The synthesis conditions are determined by conditions such as a metal compound, a ligand, a solvent, and a catalyst, and are not limited thereto.

Representative examples of the compound of the general formula [1] of the present invention are specifically shown in Table 1, but not limited thereto.

[0018]

[Table 1]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

The above metal complex can be obtained to the required purity by washing with water, an organic solvent, recrystallization from a suitable solvent, sublimation purification method, or the like, or a combination thereof.

An organic EL device is a device in which a single or multilayer organic thin film is formed between an anode and a cathode. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light-emitting layer contains a light-emitting material and may further contain a hole-transport material or an electron-transport material for transporting holes injected from an anode or electrons injected from a cathode to the light-emitting material. The multilayer type is (anode / hole injection layer / light emitting layer /
There is an organic EL device having a multilayer structure of (cathode), (anode / light-emitting layer / electron injection layer / cathode), and (anode / hole injection layer / light-emitting layer / electron injection layer / cathode). The compound of the general formula [1] can transport carriers such as holes or electrons, but since it has a better electron transporting property, its electron transporting property is used to make an electron injection layer, an electron transporting layer and an electron transporting property. It can be used for light emitting layers. In addition, an organic EL device using an organic thin film containing this compound emits strong fluorescence when an electric field is applied, and thus it can be used as a light emitting material, and it is possible to select a high emission brightness and an emission wavelength by optimal selection. Became possible.

When the organic EL element has a multi-layered structure, it is possible to prevent deterioration of brightness and life due to quenching. Further, if necessary, two or more kinds of a light emitting material, a doping material, a hole transporting material for carrying carriers and an electron transporting material can be used in combination. Also,
The hole injection layer, the light-emitting layer, and the electron injection layer may each be formed in a layer structure of two or more layers, and an element structure in which holes or electrons are efficiently injected from the electrode and transported in the layer is selected. You.

The conductive material used for the anode of the organic EL element is preferably one having a work function larger than 4 eV, such as carbon, aluminum, vanadium, iron, cobalt,
Nickel, tungsten, silver, gold, platinum, palladium and the like and alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. . The conductive material used for the cathode is preferably one having a work function of less than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium,
Lithium, ruthenium, manganese and the like and alloys thereof are used, but not limited thereto. The anode and the cathode may be formed by two or more layers if necessary.

In the organic EL device, it is desirable that at least one of them is sufficiently transparent in the emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate is also transparent. The transparent electrode is set so as to secure a predetermined translucency by a method such as vapor deposition or sputtering using the above conductive material. The electrode on the light emitting surface desirably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include a transparent resin such as a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. .

For formation of each layer of the organic EL element according to the present invention, any method such as a dry film forming method such as vacuum deposition and sputtering, and a wet film forming method such as spin coating and dipping can be applied. The film thickness is not particularly limited, but each layer needs to be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too small, pinholes or the like are generated in the thin film, and sufficient light emission luminance cannot be obtained even when an electric field is applied. Normal film thickness is 5 nm
To 10 μm is suitable, but 10 nm to 0.
The range of 2 μm is more preferable.

In the case of the wet film forming method, the material forming each layer is chloroform, tetrahydrofuran, dioxane,
A thin film is formed by dissolving or dispersing in a suitable solvent such as ethanol, but any solvent may be used. Also,
Appropriate resins and additives may be used in any of the thin films in order to improve film-forming properties and prevent pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and light-sensitive resins such as poly-N-vinyl carbazole and polysilane. Examples of the conductive resin include conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

Examples of the light emitting material or doping material that can be used in the organic EL device of the present invention include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone,
Naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinyl anthracene , Diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene and the like, and their derivatives, but are not limited thereto.

The hole-transporting material has the ability to transport holes, has an excellent hole-injecting effect on the light-emitting layer or the light-emitting material, and has an electron-injecting layer or electrons for excitons generated in the light-emitting layer. Examples thereof include compounds that prevent migration to transport materials and have excellent thin film forming ability. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, poly Arylalkane, stilbene, butadiene,
Benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine and the like, and derivatives thereof, and polyvinyl carbazole,
Although there are polymer materials such as polysilane and conductive polymer,
It is not limited to these.

The electron-transporting material has the ability to transport electrons, has an excellent electron-injecting effect on the light-emitting layer or the light-emitting material, and has a hole-injecting layer or hole-transporting layer for excitons generated in the light-emitting layer. Examples thereof include compounds that prevent transfer to the material and have excellent thin film forming ability. For example, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxadiazole, thiadiazole, tetrazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone and the like, and derivatives thereof. However, the present invention is not limited to this. Further, an electron accepting substance may be added to the hole transporting material and an electron donating substance may be added to the electron transporting material to sensitize.

The compound of the general formula [1] of the present invention can be used in a light emitting layer as a light emitting material.
At least one of the doping material, the hole transporting material and the electron transporting material may be contained in the same layer. In addition, since the compound of the general formula [1] has a high electron transporting ability, it can be used in the electron injecting layer or the electron transporting layer between the light emitting layer and the cathode.

In order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device or silicon oil or the like is enclosed to protect the entire device. It is also possible to do so.

As described above, in the present invention, since the compound of the general formula [1] is used for the organic EL device, it is possible to increase the emission brightness. In addition, this device is extremely stable against heat and current, and because it can obtain practically usable light emission brightness at low voltage, deterioration and light emission time that have been a big problem until now Was greatly improved, and it was possible to contribute to the improvement of the life of the organic EL element. . The organic EL element of the present invention can be applied to a flat panel display such as a wall-mounted television, a light source such as a copier or a printer, a light source such as a liquid crystal display or an instrument, a display board, a sign lamp, etc. , Its industrial value is very large.

[0038]

The present invention will be described in more detail based on the following examples.

(Synthesis Example 1) 6.0 g of diethoxyzinc and 300 ml of absolute ethanol were placed in a flask and stirred at 60 ° C. After all the diethoxyzinc had dissolved, a solution of 9.0 g of 2- (2-benzotriazolyl) -p-cresol at 700C was added dropwise to 700 ml of absolute ethanol. After stirring at room temperature for 1 hour, the precipitated solid was filtered, washed with anhydrous ethanol, and dried under vacuum to obtain 8.9 g of a yellowish white powder. Elemental analysis, mass spectrometry, infrared absorption spectrum and NMR spectrum of the yellowish white powder were measured, and it was found that the powder was Compound (1). FIG. 1 shows an infrared absorption spectrum of the compound (1).

Example 1 A compound (43) represented by the following chemical structure was vacuum-deposited on a washed glass plate with an ITO electrode to give a film thickness of 50 nm.
Was obtained. Then, the compound (1) was vacuum-deposited as a light-emitting material to form a light-emitting layer having a film thickness of 50 nm, and then the compound (44) was vacuum-deposited as an electron transport layer to obtain an electron transport layer having a film temperature of 50 nm. An electrode having a film thickness of 150 nm was formed on it by an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. Hole injection layer,
The light emitting layer and the cathode were vapor-deposited under the conditions of a substrate temperature of room temperature in a vacuum of 10 ⁻⁶ Torr. This element has a DC voltage of 1
At 0 V, emission of luminescence of 6000 (cd / m ² ) was obtained,
The luminous efficiency is 0.81 (lm / W) and the chromaticity is x =
It was 0.420 and y = 0.510.

Embedded image Compound (43)

Embedded image Compound (44)

Examples 2 to 36 Organic EL devices were prepared in the same manner as in Example 1 except that the compounds shown in Table 2 were used as the light emitting material.
Luminance and luminous efficiency were measured at V. Table 2 shows the results.

[0042]

[Table 2]

Example 37 Compound (43) was applied onto a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a thickness of 30 nm. Then, the compound (1) was vapor-deposited to form a light emitting layer having a film thickness of 30 nm. An electrode with a film thickness of 150 nm is formed on it by an alloy in which magnesium and silver are mixed at a ratio of 10: 1, and organic E
An L element was obtained. The hole injecting layer, the light emitting layer, the electron injecting layer, and the cathode were vapor-deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. This device has a DC voltage of 12V and 500
Light emission of 0 cd / m ² was obtained.

Example 38 On a washed glass plate with an ITO electrode, compound (8),
2- (4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxadiazole, N, N'-
(4-Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine and polycarbonate resin are dissolved and dispersed in chloroform at a ratio of 3: 2: 3: 2, and spin-coated. A light emitting layer having a film thickness of 100 nm was obtained by the method. An electrode having a thickness of 150 nm was formed thereon with an alloy of magnesium and silver mixed at a ratio of 10: 1 to obtain an organic EL device. Cathode is 10 ^-6 Torr
In a vacuum at a substrate temperature of room temperature. This device produced a light emission of 1500 cd / m ² at a DC voltage of 12V.

Examples 39 to 43 Organic EL devices were produced in the same manner as in Example (38) except that the compounds shown in Table 3 were used instead of the compound (8), and the luminance and luminous efficiency at a DC voltage of 12 V were obtained. Was measured. Table 3 shows the results.

[0046]

[Table 3]

Example 44 Compound (1) was added on a washed glass plate with an ITO electrode.
Poly-N-vinylcarbazole was dissolved and dispersed in chloroform at a ratio of 3: 5, and a light emitting layer having a film thickness of 100 nm was obtained by a spin coating method. An electrode having a thickness of 150 nm was formed thereon with an alloy of magnesium and silver mixed at a ratio of 10: 1 to obtain an organic EL device. The light emitting layer and the cathode
It was vapor-deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. This element is 1000 cd / d at a DC voltage of 12V.
A light emission of m ² was obtained.

Example 45 Compound (43) was applied onto a washed glass plate with an ITO electrode.
Was dissolved and dispersed in chloroform, and a hole injection layer having a thickness of 30 nm was obtained by spin coating. Then, the compound (25) is vapor-deposited to form a light-emitting layer having a thickness of 50 nm, and then 2- (4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxadiene is formed by a vacuum vapor deposition method. An electron injection layer having a film thickness of 20 nm of azole was obtained. in addition,
An alloy of magnesium and silver mixed at a ratio of 10: 1 with a film thickness of 15
An 0 nm electrode was formed to obtain an organic EL device. Light-emitting layer,
The electron injection layer and the cathode were formed in a vacuum of 10 ⁻⁶ Torr.
The deposition was performed at a substrate temperature of room temperature. The device emitted light of 6500 cd / m ² at a DC voltage of 12 V.

Example 46 Compound (43) was applied onto a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a thickness of 30 nm. Next, the compound (1) was vapor-deposited to form a light-emitting layer having a thickness of 30 nm, and an electron injection layer having a thickness of 20 nm of the compound (11) was obtained by vacuum vapor deposition. An electrode having a thickness of 150 nm was formed thereon with an alloy of magnesium and silver mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injecting layer, the light emitting layer, the electron injecting layer, and the cathode were vapor-deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. The device emitted light of 6300 cd / m ² at a DC voltage of 12 V.

The organic EL device shown in this embodiment has an emission luminance of 5000c in a device structure of two layers or more.
It was d / m ² or more, and it was possible to obtain high luminous efficiency in all cases. Further, when all the organic EL elements shown in this example were made to emit light continuously at 3 mA / cm ² ,
Light emission stable for 000 hours or more could be observed. The organic EL device of Example 1 had a stable emission luminance for 1000 hours or longer, and almost no dark spots were observed, whereas the organic EL device of Comparative Example 1 produced under the same conditions was 500 hours or less. The light emission time was less than half of the initial light emission luminance, the number of dark spots was large, and the number increased and became large as the life time was measured. This is because the adhesion between the light emitting layer on which the tris (8-hydroxyquinoline) aluminum complex is formed and the cathode electrode layer is close to each other, that the tris (8-hydroxyquinoline) aluminum complex does not easily form a thin film having a uniform film thickness, It is considered that there is a large difference in work function between the layer and the cathode. From the above results, the organic EL of the present invention was formed in the light emitting layer and the layer between the light emitting layer and the cathode.
The organic EL device using the device material has achieved a long life of the light emitting device.

The organic EL device of the present invention achieves improvement of luminous efficiency and luminous brightness and prolongation of life, and is used together with a light emitting material, a doping material, a hole transporting material, an electron transporting material and a sensitizing material. There is no limitation on the agent, resin, electrode material, etc., and the method for producing the element.

[0052]

The organic EL device material of the present invention uses a novel metal complex as a light emitting material as a constituent. The organic EL element showed light emission with higher luminous efficiency than that of the conventional one, and a long-life organic EL element could be obtained. Also,
The organic EL device using the organic EL device material of the present invention between the cathode of the device and the light emitting layer had a longer life than the conventional device. As described above, by using the compound shown in the present invention in at least one layer of an organic EL device, it becomes possible to easily produce an organic EL device having high emission brightness, high emission efficiency and long life.

[Brief description of the drawings]

FIG. 1 is an infrared absorption spectrum diagram of compound (1).

Claims (4)

[Claims] 1. An organic electroluminescence element material represented by the following general formula [1]. General formula [1] [In the formula, X represents N or CH, and R ¹ to R ⁸
Are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted An alkylthio group, a substituted or unsubstituted arylthio group, an amino group, a mono- or di-substituted amino group, a hydroxyl group, a siloxy group, an acyl group, a carbamoyl group, a carboxylic acid group,
A sulfonic acid group, an aliphatic ring group, a carbocyclic aromatic group or a heterocyclic group is shown. M represents a metal. n represents an integer of 1 to 3. ] 2. An organic electroluminescent device comprising a light emitting layer or an organic compound thin film layer including a light emitting layer between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material according to claim 1. An organic electroluminescence device characterized by the above. 3. An organic electroluminescent device comprising a plurality of organic compound thin film layers including a light emitting layer between a pair of electrodes, wherein the organic electroluminescent device material according to claim 1 is contained between the light emitting layer and the cathode. An organic electroluminescence device comprising a layer for forming an organic electroluminescence device. 4. A layer containing a triphenylamine derivative is further formed between the light emitting layer and the anode.
The organic electroluminescence device described.