JP3067469B2 - Organic electroluminescence device - Google Patents

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) device used for a flat light source and a display.

[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. In general EL element
The element 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, holes are injected from the anode side , and the electrons recombine with holes in the light emitting layer, and the energy level is changed to the conduction band. This is a phenomenon in which energy is emitted as light when returning to the valence band from.

[0003] Conventional organic EL devices have a higher driving voltage and lower luminous brightness and luminous efficiency than inorganic EL devices.
In addition, the characteristic deterioration was remarkable, and it had not been put to practical use.
2. Description of the Related Art In recent years, an organic EL in which a thin film containing an organic compound having high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less is laminated.
Devices have been reported and are of interest (see Applied Physics Letters, vol. 51, p. 913, 1987). In this method, the metal chelate complex is converted into a phosphor layer,
High brightness green light emission is obtained by using an amine compound for the hole injection layer, and the brightness is several hundreds at a DC voltage of 6 to 7V.
It achieves cd / m ² and maximum luminous efficiency of 1.5 lm / W, and has performance close to the practical range. However,
The emission intensity of organic EL elements up to now has been improved by improving the structure, but does not yet have sufficient emission luminance. In addition, there is a major problem that the stability upon repeated use is poor. Therefore, at present, it is desired to develop an organic EL device having higher emission luminance and excellent stability when repeatedly used.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic EL device having a high luminous intensity and excellent stability when used repeatedly. As a result of intensive studies by the present inventors, an organic EL device using an organic compound represented by the general formula [1] for a light-emitting layer or a hole transport layer has high emission intensity and high stability when used repeatedly. It was found to be excellent and led to the present invention.

[0005]

That is, a first aspect of the present invention is an organic electroluminescent device having a light-emitting layer composed of one or more organic compound thin films between a pair of electrodes, wherein at least one layer has the following general formula: An organic electroluminescence device which is a layer containing the compound represented by [1].

The general formula [1]

Embedded image [Wherein, R ¹ to R ¹² each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, a mono- or di-substituted amino group, an acylamino group, a hydroxyl group, an alkoxy group, a mercapto group , Alkyloxy group, alkylthio group, aryloxy group, arylthio group, siloxy group, acyl group, cycloalkyl group, carbamoyl group, carboxylic acid group, sulfonic acid group, substituted or unsubstituted aliphatic group, substituted or unsubstituted It represents an aliphatic ring group, a substituted or unsubstituted carbocyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group, or a substituted or unsubstituted heterocyclic group. Also, R ¹ and R ² are
The is R ³ and R ^4, a substituted or unsubstituted aliphatic type ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic May be formed. ]

According to a second aspect of the present invention, there is provided an organic electroluminescent device having a light emitting layer comprising one or more organic compound thin films between a pair of electrodes, wherein the light emitting layer contains a compound represented by the general formula [1]. The organic electroluminescent device is a layer.

According to a third aspect of the present invention, there is provided an organic electroluminescence device having a light emitting layer comprising one or more organic compound thin films between a pair of electrodes, wherein the hole injection layer comprises a compound represented by the general formula [1]. It is an organic electroluminescence element which is a layer containing.

Examples of the group of the compound represented by the general formula [1] in the present invention and a substituent atom or a substituent added to the group include a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, Carboxy group, sulfone group, amino group, acylamino group, ester group, mono- or di-substituted amino group, alkoxy group, mercapto group, or methyl group, ethyl group, propyl group, butyl group, sec
-Butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, aminomethyl group, acetooxymethyl group, acetooxyethyl group, acetooxypropyl group,
Acetooxybutyl group, hydroxymethyl group, hydroxylethyl group, hydroxylpropyl group, hydroxylbutyl group, vinyl group, styryl group, acetylene group, alkoxy group, mercapto group, alkyloxy group, alkylthio group, aryloxy group, arylthio group, A substituent such as a siloxy group, an acyl group, a cycloalkyl group, a carbamoyl group and a substituted or unsubstituted acyclic hydrocarbon group,
Cyclopropyl group, cyclohexyl group, 1,3-cyclohexadienyl group, 2-cyclopenten-1-yl group,
2,4-cyclopentadiene-1-ylenyl group, phenyl group, biphenylenyl group, triphenylenyl group, tetraphenylenyl group, 2-methylphenyl group, 3-nitrophenyl group, 4-methylthiophenyl group, 3,5-dicyano A substituted or unsubstituted monocyclic hydrocarbon group such as phenyl group, o-, m- and p-tolyl group, xylyl group, o-, m- and p-cumenyl group, mesityl group, pentalenyl group, indenyl group, Naphthyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group,
Fluorenyl group, anthryl group, anthraquinonyl group,
3-methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, 2-ethyl-
1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, colonenyl group, trinaphthenyl group, heptaphenyl group, heptacenyl Group, pyranthrenyl group, substituted or unsubstituted condensed polycyclic hydrocarbon such as ovalenyl group, thienyl group, furyl group, pyrrolyl group,
Imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, quinazolinyl, carbazolyl, acridinyl, phenazinyl, furfuryl, isothiazolyl , Isoxazolyl group, furazanyl group, phenoxazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2-methylpyridyl group,
A substituted or unsubstituted heterocyclic group such as a 3-cyanopyridyl group or a substituted or unsubstituted aromatic polycyclic group, a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group Group, pentyloxy group, hexyloxy group, stearyloxy group, phenoxy group, methylthio group, ethylthio group, propylthio group, butylthio group, sec-butylthio group, t
tert-butylthio group, pentylthio group, hexylthio group, heptylthio group, octylthio group, phenylthio group, amino group, methylamino group, dimethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group , Bis (acetooxymethyl) amino group, bis (acetooxyethyl) amino group, bis (acetooxypropyl) amino group, bis (acetooxybutyl) amino group, dibenzylamino group, methylsulfamoyl group, dimethylsulfo Famoyl, ethylsulfamoyl, diethylsulfamoyl, propylsulfamoyl, butylsulfamoyl, phenylsulfamoyl, diphenylsulfamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl Yl, diethylcarbamoyl, propylcarbamoyl, butylcarbamoyl, phenylcarbamoyl, methylcarbonylamino, ethylcarbonylamino, propylcarbonylamino, butylcarbonylamino, phenylcarbonylamino, methoxycarbonylamino, ethoxy Carbonylamino group, propoxycarbonylamino group, butoxycarbonylamino group, phenoxycarbonyl group,
2- (2-ethoxyethoxy) ethoxy group, 2- (2-
An ethoxyethoxy) ethylthio group, a 2- [2- (2-methoxyethoxy) ethoxy] ethylthio group,
It is not limited to these substituents.

The kind, number and position of the substituent atoms or substituents of the compound of the formula [1] used in the present invention are not particularly limited.

The compound of the general formula [1] of the present invention can be prepared by, as a first synthesis method, reacting a 9,10-diaminophenanthrene derivative and a halobenzene derivative in a nitrogen atmosphere in an organic solvent or without solvent in the presence of a base and a catalyst. It can be obtained by reacting at a predetermined temperature for a predetermined time. As a second synthesis method, 9,10-phenanthrenequinone and an aniline derivative are reacted in the presence of an acid catalyst to form a diimino derivative, and then reduced to obtain a diamine derivative, which is obtained by reacting the diamine derivative with a halobenzene derivative. However, the present invention is not limited to these synthetic methods.

The halogen atom of the halobenzene derivative used in the synthesis of the compound of the general formula [1] includes chlorine, bromine, iodine and the like. The base used in the present invention includes inorganic bases such as potassium carbonate, lithium hydroxide, and sodium hydroxide, pyridine, picoline, triethylamine, N-methylpyrrolidine, 1,5-diazabicyclo [5,4,0] undecene. Organic bases such as (DBU) can be mentioned. Examples of the catalyst used in the present invention include copper powder, copper oxide, copper halide, and copper sulfate. The solvent used in the present invention may be any solvent capable of dissolving the raw materials and causing the reaction. For example, solvents such as toluene, xylene, nitrobenzene, dimethyl sulfoxide, N, N-dimethylformamide and the like can be mentioned. As the acid catalyst, concentrated sulfuric, p- toluenesulfonic acid, polyphosphoric acid, TiCl _4, AlCl _3, and the like polyethylene sulfonic acid. As a reducing agent, Zn, S
n, H ₂ / Pt, H ₂ / Pd, H ₂ / Ni and the like.

Hereinafter, typical examples of the compound of the general formula [1] used in the present invention are specifically shown in Table 1, but the present invention is not limited to the following typical examples.

[0014]

[Table 1]

[0015]

[0016]

FIGS. 1 to 3 show an organic EL used in the present invention.
An example of a schematic diagram of the device is shown. In the figure, generally, electrode 2, 2 is an anode, and electrode B, 6 is a cathode. Further, there is an organic EL device laminated with a layer structure of (electrode A / light-emitting layer / electron injection layer / electrode B), and the compound of general formula [1] can be suitably used in this device structure. . Since the compound of the general formula [1] has both strong light emission and large carrier transport ability, the hole injection layer 3,
Either of the light emitting layer 4 and the electron injection layer 5 can be used as a light emitting substance, a light emitting auxiliary, and a carrier transporting substance.

The light-emitting layer 4 of FIG. 1 may include, if necessary, a light-emitting substance, a light-emitting auxiliary material, a hole-transport material for transporting carriers, and an electron-transport material, in addition to the compound of the general formula [1] of the present invention. Can also be used. In the structure of FIG. 2, the light emitting layer 4 and the hole injection layer 3 are separated. With this structure, the hole injection efficiency from the hole injection layer 3 to the light emitting layer 4 is improved, and the light emission luminance and the light emission efficiency can be increased. in this case,
For luminous efficiency, it is desirable that the luminescent substance used in the luminescent layer itself has an electron transporting property, or that the luminescent layer is made to have an electron transporting property by adding an electron transporting material to the luminescent layer.

The structure shown in FIG. 3 has an electron injection layer 5 in addition to the hole injection layer 3 to improve the efficiency of recombination of holes and electrons in the light emitting layer 4. In this manner, by making the organic EL element have a multilayer structure, it is possible to prevent a decrease in luminance and life due to quenching. 2 and 3, the light-emitting substance, the light-emitting auxiliary material, the hole-transporting material for transporting carriers, and the electron-transporting material can be used in combination, if necessary.

As the conductive substance used for the anode of the organic EL element, those having a work function of more than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum , Palladium and the like, alloys thereof, metal oxides such as tin oxide and indium oxide called ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the cathode, those having a work function of less than 4 eV are preferable, and magnesium, calcium, tin, lead, titanium,
Yttrium, lithium, ruthenium, manganese, and the like and alloys thereof are used, but are not limited thereto.

In the organic EL device, at least one of the electrode A indicated by 2 and the electrode B indicated by 6 is desirably sufficiently transparent in the emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate 1 is also transparent. The transparent electrode is set so as to secure a predetermined light transmittance by a method such as vapor deposition or sputtering using the above-described conductive substance. The electrode that extracts light emission
It is desirable that the light transmittance be 10% or more.

The substrate 1 is not limited as long as it has a mechanical and thermal strength and is transparent. Examples thereof include a glass substrate, a polyethylene plate, a polyethersulfone plate, and a polypropylene plate. Transparent resin.

Each layer of the organic EL device according to the present invention can be formed by any of a dry film forming method such as vacuum evaporation and sputtering and a wet film forming method such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate thickness. If the film thickness is too large, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too small, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. Normal film thickness is from 10 nm to 10
μm, preferably in the range of 100 Angstroms to 2000 Angstroms.

In the case of the wet film forming method, a thin film is formed by using a solution in which a material for forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane or the like. May be. Further, in any of the organic layers, an appropriate resin or additive may be used for improving film forming properties, preventing pinholes in the film, and the like. Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, urethane, polysulfone, polymethyl methacrylate, and polymethyl acrylate;
Examples thereof include photoconductive resins such as N-vinylcarbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.

The present organic EL device has a light emitting layer, a hole injection layer,
In the electron injection layer, if necessary, in addition to the compound of the general formula [1], a known light emitting substance, light emission auxiliary material, hole transport material, and electron transport material can also be used.

Known light-emitting substances or auxiliary materials for light-emitting substances include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene. , Coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, oxine, aminoquinoline, imine, diphenylethylene, vinylanthracene, diaminocarbazole,
Examples include, but are not limited to, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, and the like, and derivatives thereof.

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 substance, and has an electron injection layer or an electron exciton generated in the light emitting layer. Compounds that prevent transfer to a transport material and have excellent thin film forming ability can be used. 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 a capability of transporting electrons, has an excellent electron injecting effect on a light emitting layer or a light emitting substance, and has a hole injection layer or a hole transporting function of excitons generated in the light emitting layer. Compounds that prevent transfer to a material and have excellent thin film forming ability are exemplified. For example, fluorenone, anthraquinodimethane, diphenylquinone, thiopyran dioxide, oxadiazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane,
Examples include, but are not limited to, anthrones and derivatives thereof. The sensitization can also be performed by adding an electron accepting substance to the hole transporting material and adding an electron donating substance to the electron transporting material.

In the organic EL devices shown in FIGS. 1, 2 and 3, the compound of the general formula [1] of the present invention can be used for any layer, and in addition to the compound of the general formula [1], At least one of a light emitting substance, a light emission auxiliary material, a hole transport material, and an electron transport material may be contained in the same layer. In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or silicon oil or the like is sealed to protect the entire device. It is also possible. As described above, in the present invention, since the compound of the general formula [1] was used for the organic EL device, the luminous efficiency and the luminous brightness could be increased. Also,
This element is extremely stable against heat and current, and furthermore, it can emit light that can be used practically at a low driving voltage, so that the degradation, which was a major problem up to now, can be greatly reduced. Was. 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 and the like as a plane light emitter. , Its industrial value is very large.

[0030]

The present invention will be described in more detail with reference to the following examples. (Synthesis example) Synthesis method of compound (1) 9,10-diaminophenanthrene 5
g, 85 g of iodobenzene, 21 g of caustic potash and 0.2 g of copper sulfate pentahydrate at 250 ° C. under a nitrogen atmosphere.
For 12 hours. After completion of the reaction, the mixture was cooled to 60 ° C., diluted with ethyl acetate, and filtered. The residue obtained by concentrating the filtrate under reduced pressure was recrystallized from toluene to give a melting point of 212.
C., 7.2 g of compound (1) as a yellowish white powder was obtained. Synthesis method of compound (2) 800 ml of toluene, 36 g of 9,10-phenanthrenequinone, 62 g of p-toluidine and 70 ml of pyridine were added to a flask, and after cooling to 5 ° C, titanium tetrachloride 10
A solution of 0 g dissolved in 350 ml of toluene was added dropwise. Thereafter, the reaction was carried out at 20 ° C. for 8 hours. After completion of the reaction, water 12
After adding 00 ml and 350 ml of ethyl acetate to carry out liquid separation, the organic layer was concentrated under reduced pressure. Ethanol 3 in concentrate
After adding 50 ml and heating under reflux, the mixture was cooled to room temperature and filtered to obtain 42.2 g of 9,10-di (4-methylanilino) phenanthrene as a pale yellow powder. Next, p-
A mixture of 4.3 g of iodotoluene, 1.3 g of potassium carbonate, 5 mg of cuprous chloride, and 0.9 g of 9,10-di (4-methylanilino) phenanthrene was heated at 190 ° C. under a nitrogen stream.
For 30 hours. 80 ml of water and 80 ml of chloroform were added to the reaction mixture, and the mixture was separated. The residue obtained by concentrating the chloroform layer under reduced pressure was recrystallized from n-hexane to give Compound (2) having a melting point of 228 ° C in 0.1 ml. 85g
Obtained.

Example 1 An organic EL device was manufactured by forming a light emitting layer of the compound (1) on a washed glass plate with an ITO electrode by a vacuum evaporation method. The light emitting layer was deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. An electrode having a thickness of 1500 angstroms was formed thereon using an alloy obtained by mixing magnesium and silver at a ratio of 10: 1 to obtain the organic EL device shown in FIG. This device emitted light of 49 cd / m ² at a DC voltage of 10 V.

Example 2 Compound (2) was dissolved and dispersed in chloroform on a washed glass plate with an ITO electrode, and a light emitting layer was formed by spin coating to obtain a light emitting layer having a thickness of 500 Å. And one more magnesium and silver
An electrode having a thickness of 1500 angstroms was formed from an alloy mixed at 0: 1 to obtain an organic EL device having the structure shown in FIG. This device emitted light of 35 cd / m ² at a DC voltage of 10 V.

Example 3 Compound (3) was placed on a washed glass plate with an ITO electrode.
N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine and poly-N-vinylcarbazole in chloroform at a ratio of 3: 2: 5 It was dissolved and dispersed, and a light emitting layer having a thickness of 500 Å was obtained by spin coating. On top of this, a 15: 1 alloy of magnesium and silver mixed at a ratio of 10: 1
An electrode having a thickness of 00 Å was formed to obtain the organic EL device shown in FIG. This device emitted 70 cd / m ² of light at a DC voltage of 10 V.

Example 4 N, N'-diff was placed on a washed glass plate with ITO electrodes.
Enyl-N, N '-(3-methylphenyl) -1,1'-
Biphenyl-4,4'-diamine is vacuum deposited to form 30
A hole injection layer having a thickness of 0 Å was obtained. Next
Then, the film thickness of the compound (4) is 500 angstroms by a vacuum evaporation method.
Create a strom light-emitting layer, over which magnesium
Angstro with an alloy of 10: 1 silver and silver
Forming an electrode having a film thickness of
Obtained. The hole injection layer and the light emitting layer are 10 ^-6Torr vacuum
In this case, evaporation was performed under the condition of a substrate temperature of room temperature. This element
About 220 cd / m at DC voltage 10V^TwoOf light emission
Was. From these results, it was found that the compound of the present invention has an electron transporting property.
It turns out that it is a light substance.

Example 5 Compound (5) was vacuum-deposited on a cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 300 Å. Next, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light-emitting layer having a thickness of 500 angstroms, and an electrode having a thickness of 1500 angstroms made of an alloy obtained by mixing magnesium and silver at a ratio of 10: 1. Was formed to obtain an organic EL device shown in FIG. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. This element
Light emission of about 380 cd / m ² was obtained at a DC voltage of 10 V.

Example 6 N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'- was placed on a washed glass plate with an ITO electrode.
Biphenyl-4,4′-diamine was vacuum-deposited to obtain a hole injection layer having a thickness of 300 Å. Then
A 200-Å-thick light-emitting layer of compound (6) was formed by vacuum evaporation, and [2] was formed by vacuum evaporation.
-(4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxadiazole] to obtain an electron injection layer having a thickness of 200 Å. An electrode having a thickness of 1500 angstroms was formed thereon using an alloy obtained by mixing magnesium and silver at a ratio of 10: 1 to obtain an organic EL device shown in FIG. This element is approximately 450 cd at 10 V DC
/ M ² was obtained.

When all the organic EL devices shown in this example were continuously emitted at 1 mA / cm ² , 10
Stable light emission could be observed for 00 hours or more. The organic EL device of the present invention achieves luminous efficiency, improved luminous brightness and longer life, and a luminescent material used in combination therewith,
Luminescence auxiliary materials, hole transport materials, electron transport materials, sensitizers,
It does not limit the resin, the electrode material and the like, and the element manufacturing method.

[0038]

According to the present invention, it is possible to obtain an organic EL device having higher luminous efficiency, higher luminance and longer life than the conventional one.

[0039]

[Brief description of the drawings]

FIG. 1 is a cross-sectional view illustrating a schematic structure of an organic EL device used in an example.

FIG. 2 is a sectional view showing a schematic structure of an organic EL device used in Examples.

FIG. 3 is a sectional view illustrating a schematic structure of an organic EL device used in an example.

[Explanation of symbols]

 1. Substrate 2. Electrode A3. 3. Hole injection layer Light emitting layer 5. Electron injection layer 6. Electrode B

Claims (3)

(57) [Claims] 1. An organic electroluminescence device comprising a light emitting layer comprising one or more organic compound thin films between a pair of electrodes, wherein at least one layer is a layer containing a compound represented by the following general formula [1]. An organic electroluminescent device, comprising: General formula [1] [Wherein, R ¹ to R ¹² each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, a mono- or di-substituted amino group, an acylamino group, a hydroxyl group, an alkoxy group, a mercapto group , Alkyloxy group, alkylthio group, aryloxy group, arylthio group, siloxy group, acyl group, cycloalkyl group, carbamoyl group, carboxylic acid group, sulfonic acid group, substituted or unsubstituted aliphatic group, substituted or unsubstituted It represents an aliphatic ring group, a substituted or unsubstituted carbocyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group, or a substituted or unsubstituted heterocyclic group. Also, R ¹ and R ² are
The is R ³ and R ^4, a substituted or unsubstituted aliphatic type ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic May be formed. ] 2. An organic electroluminescence device having a light emitting layer comprising one or more organic compound thin films between a pair of electrodes, wherein the light emitting layer is a layer containing a compound represented by the general formula [1]. The organic electroluminescent device according to claim 1, wherein: 3. An organic electroluminescence device having a light emitting layer comprising a plurality of organic compound thin films between a pair of electrodes, wherein the hole injection layer is a layer containing a compound represented by the general formula [1]. The organic electroluminescent device according to claim 1, wherein: