JPH07150136A - Organic electroluminescent device - Google Patents

Abstract

PURPOSE:To improve stability during repeated use and luminous intensity by incorporating a specific compd. into the luminescent layer. CONSTITUTION:A transparent anode A2 with a thickness of 10nm to 10mum gel is formed from a conductive substance having a work function higher than 4eV on a transparent substrate 1 having sufficient mechanical and thermal strengths by vapor deposition or sputtering. On the anode A2 is formed a luminescent layer 4 which comprises at least one thin org. compd. layer of which at least one layer contains a compd. of formula I and/or formula II (wherein A and B are each an alicyclic, an arom. hydrocarbon, an arom. heterocyclic, or a hetrocyclic group; X<1>, X<2>, Y<1>, and y<2> are each O, S, Se, Te, NR<1>, or PR<2>; and R<1> and R<2> are each II, halogen, cyano, nitro, amino, ester, mono- or di- substd. amino, acylamino, hydroxyl, alkoxy, etc.) and, if necessary, a luminescent substance, an assistant luminescent substance, a hole transport substance, etc. On the luminescent layer 4 is formed a transparent cathode B6 with a thickness of 10nm to 10mum from a conductive substance having a work function lower than 4eV by vapor deposition or sputtering.

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.

[0002]

2. Description of the Related Art An EL element using an organic substance is expected to be used as a solid-state light emitting type inexpensive large area full color display element, and many developments have been made. Generally EL
Is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting 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, this is a phenomenon in which 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.

A conventional organic EL element has a higher driving voltage and lower emission brightness and emission efficiency than an inorganic EL element.
In addition, the deterioration of the characteristics was remarkable and it was not put to practical use.
In recent years, an organic EL in which thin films containing an organic compound having a high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less are laminated
The device has been reported and is of great interest (see Applied Physics Letters, 51, 913, 1987).

In this method, a metal chelate complex is used for the phosphor layer and an amine compound is used for the hole injection layer to obtain high-luminance green light emission, and the luminance is several 1 at a DC voltage of 6 to 7V.
The maximum luminous efficiency is 00 cd / m ² and the maximum luminous efficiency is 1.5 lm / W, which is close to the practical range. However, although the organic EL devices to date have improved the emission intensity due to the improved structure, they still do not have sufficient emission brightness. Further, it has a big problem that it is inferior in stability when repeatedly used. Therefore, under the present circumstances, it is desired to develop an organic EL device having a larger emission brightness and excellent stability in repeated use.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic EL device having a large emission intensity and excellent stability in repeated use. As a result of diligent studies by the present inventors, an organic EL device using the organic compound represented by the general formula [1] and / or the general formula [2] has a large emission intensity and is stable in repeated use. The inventors have found that they are excellent and have reached the present invention.

[0006]

[Means for Solving the Problems] That is, the first invention is an organic electroluminescence device comprising a light emitting layer composed of one or more organic compound thin films between a pair of electrodes, at least one of which is represented by the following general formula: [1] and /
Alternatively, the organic electroluminescence device is a layer containing the compound represented by the general formula [2].

General formula [1]

[0008]

[Chemical 1]

General formula [2]

[0010]

[Chemical 2]

[In the formula, A and B are each independently a substituted or unsubstituted aliphatic ring group, a substituted or unsubstituted carbocyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group. Represents a group or a substituted or unsubstituted heterocyclic group. −
X ¹ −, −X ² −, ═Y ¹ and ═Y ² are each independently
Indicates O, S, Se, Te, NR ¹ or PR ² . R ¹ and R ² are each independently 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, an 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 aliphatic ring Represents a group, a substituted or unsubstituted carbocyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group, or a substituted or unsubstituted heterocyclic group.

The second invention is an organic electroluminescence device having a light emitting layer composed of one or a plurality of organic compound thin films between a pair of electrodes, wherein the light emitting layer is represented by the general formula [1] and / or the general formula. It is an organic electroluminescence device which is a layer containing the compound represented by [2].

Examples of the group of the compounds represented by the general formulas [1] and [2] in the present invention and the substituent atom or the substituent to be added to the group include a hydrogen atom, a halogen atom, a cyano group, Nitro group, 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, acetoxymethyl group, acetoxyethyl group, acetoxypropyl group, acetoxybutyl group, Hydroxymethyl group, hydroxylethyl group, hydroxylpropyl group,
Substituents such as hydroxylbutyl group, vinyl group, styryl group, acetylene group, alkoxy group, mercapto group, alkyloxy group, alkylthio group, aryloxy group, arylthio group, siloxy group, acyl group, cycloalkyl group, 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-yridenyl group, phenyl group, biphenylenyl group, triphenylenyl group, tetraphenylenyl group, 2-methylphenyl group , 3-nitrophenyl group, 4-methylthiophenyl group, 3,5-dicyanophenyl group, o-, m- and p
-Tolyl group, xylyl group, o-, m- and p-cumenyl group, substituted or unsubstituted monocyclic hydrocarbon group such as mesityl group, pentalenyl group, indenyl group, naphthyl group,
Azulenyl group, heptanenyl 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-chloroperenylyl group Substituted or unsubstituted condensation of, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptacenyl group, pyrantrenyl group, ovalenyl group, etc. Polycyclic hydrocarbon, thienyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, quinolyl group, isoquinolyl group, phthalazinyl group, quinoki Linyl group, quinazolinyl group, carbazolyl group, acridinyl group, phenazinyl group, furfuryl group, isothiazolyl group, isoxazolyl group, flazanyl group, phenoxazinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, 2-methylpyridyl group, 3 -Substituted or unsubstituted heterocyclic group such as cyanopyridyl group or substituted or unsubstituted aromatic vinyl group, hydroxyl group, methoxy group, ethoxy group, propoxy group, butoxy group, sec-butoxy group, tert-butoxy group , Pentyloxy, hexyloxy, stearyloxy, phenoxy, methylthio, ethylthio, propylthio, butylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, heptylthio, octyl Ruthio group, phenylthio group, amino group, methylamino group, dimethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group, bis (acetooxymethyl) amino group, bis (acetoxy group Ethyl) amino group, bis (acetooxypropyl) amino group, bis (acetooxybutyl) amino group, dibenzylamino group, methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, diethylsulfamoyl group Group, propylsulfamoyl group, butylsulfamoyl group, phenylsulfamoyl group, diphenylsulfamoyl group, methylcarbamoyl group, dimethylcarbamoyl group, ethylcarbamoyl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group Group, phenylcarbamoyl group, methylcarbonylamino group, ethylcarbonylamino group, propylcarbonylamino group, butylcarbonylamino group, phenylcarbonylamino group, methoxycarbonylamino group, ethoxycarbonylamino group, propoxycarbonylamino group,
Butoxycarbonylamino group, phenoxycarbonyl group, 2- (2-ethoxyethoxy) ethoxy group, 2-
(2-Ethoxyethoxy) ethylthio group, 2- [2-
(2-Methoxyethoxy) ethoxy] ethylthio group and the like, but not limited to these substituents.

The kind, number, and position of the substituent atom or substituent in the compounds of the general formulas [1] and [2] used in the present invention are not particularly limited. Hereinafter, typical examples of the compounds of the general formula [1] and the general formula [2] used in the present invention are specifically illustrated in Table 1, but the present invention is not limited to the following typical examples. .

[0015]

[Table 1]

[0016]

[0017]

[0018]

[0019]

1 to 3 show the organic EL used in the present invention.
An example of a schematic view of the device is shown. In the figure, generally, the electrode A 2 is an anode, and the electrode B 6 is a cathode. In addition to these layer configurations, there is an organic EL element in which (electrode A / light emitting layer / electron injection layer / electrode B) is laminated in this order,
The compound of the general formula [1] can be preferably used also in this device constitution.

Since the compounds of the general formulas [1] and [2] have both strong light emission and large carrier transport ability, they can be used in any of the hole injection layer 3, the light emitting layer 4 and the electron injection layer 5. It can be used as a luminescent substance, a luminescence auxiliary, and a carrier transport substance. In the light emitting layer 4 of FIG. 1, if necessary,
In addition to the compounds of the general formula [1] and the general formula [2] of the present invention, a light emitting substance, a light emission assisting material, a hole transporting material for transporting carriers, and an electron transporting material 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 brightness and the light emission efficiency can be increased. In this case, for light emission efficiency, the light emitting substance itself used in the light emitting layer has an electron transporting property, or an electron transporting material is added to the light emitting layer to make the light emitting layer have an electron transporting property. desirable.

The structure of 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. As described above, by forming the organic EL element into a multi-layer structure, it is possible to prevent a decrease in brightness and life due to quenching. Also in the elements of FIGS. 2 and 3, if necessary, a light emitting substance, a light emission auxiliary material, a hole transporting material for carrier transport, and an electron transporting material can be used in combination.

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

In the organic EL device, it is desirable that at least one of the electrode A shown by 2 and the electrode B shown by 6 is 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 made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrode that takes out the emitted light is
It is desirable that the light transmittance is 10% or more. Board 1
Is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include transparent resins such as glass substrates, polyethylene plates, polyether sulfone plates, and polypropylene plates. .

For forming each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition and sputtering, and wet film forming methods 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 thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. Normal film thickness is 10 nm to 10
It is in the range of μm, and preferably in the range of 100 Å to 2000 Å.

In the case of the wet film forming method, a thin film is formed by using a solution in which the material forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane, etc., which solvent is used. May be. Further, in any of the organic layers, an appropriate resin or additive may be used in order to improve the film-forming property and prevent pinholes in the film. Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polysulfone, polymethylmethacrylate, and polymethylacrylate; photoconductive resins such as poly-N-vinylcarbazole and polysilane; and polythiophene. Examples thereof include conductive resins such as polypyrrole.

The present organic EL device comprises 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] or the general formula [2], a known light emitting substance, light emission auxiliary material, hole transporting material, electron transporting material can be used. . In that case, the compound of the general formula [1] or the general formula [2] is used as a main luminescent material, and the following known luminescence auxiliary material is doped, or the following known luminescence auxiliary material is used as a main luminescent material. ] Or a compound of the general formula [2] can be doped to obtain an organic EL device having appropriate emission brightness and emission wavelength. The doping amount of the light emission assisting material depends on each material and may be any amount, but 0.1 to 50 parts by weight of the light emission assisting material, preferably 0.5 to 100 parts by weight of the light emitting substance. A doping amount of 10 parts by weight is desirable.

Known luminescent substances or auxiliary substances of luminescent 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 their derivatives.

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-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, fullerocyanines, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolthione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene , Benzidine type triphenylamine,
Examples thereof include, but are not limited to, styrylamine-type triphenylamine, diamine-type triphenylamine and the like, their derivatives, and polymeric materials such as polyvinylcarbazole, polysilane and conductive polymers.

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 substance, 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, fluorenone, anthraquinodimethane, diphenylquinone, thiopyran dioxide, oxadiazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane,
Examples include, but are not limited to, anthrone and derivatives thereof. It is also possible to sensitize 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] and the compound of the general formula [2] can be used in any of the layers. At least one of the hole transport material and the electron transport material may be contained in the same layer.

Further, 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 sealed in the entire device. It is also possible to protect As described above, in the present invention, since the compound of the general formula [1] and / or the general formula [2] is used for the organic EL device, the luminous efficiency and the luminous brightness can be increased. In addition, this device is extremely stable against heat and current, and because it can obtain practically usable light emission brightness at a low driving voltage, it can significantly reduce deterioration, which was a major problem until now. I was able to.

The organic EL device of the present invention can be used as a flat panel display such as a wall-mounted television or a flat light-emitting body.
It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, marker lights, etc., and its industrial value is very large.

[0035]

The present invention will be described in more detail based on the following examples. In the examples, “part” means “part by weight”.

(Synthesis Example) Method for synthesizing compound (2) In a flask, 20 parts of phenylthioglycolic acid-o-carboxylic acid and 100 parts of sodium hydroxide were melted, cooled, diluted with water and diluted with water. After neutralizing a part of sodium with an acid, 30 parts of red blood salt was added and then filtered and washed with water to obtain 16 parts of a red precipitate. As a result of analyzes such as mass spectrometry and infrared absorption spectrum, it was confirmed that it was thioindigo represented by the compound (2).

Example 1 Compound (1) was dissolved and dispersed in chloroform on a washed glass plate with an ITO electrode, and a light emitting layer was formed by a spin coating method to obtain a light emitting layer having a thickness of 500 Å. On top of that, add 1 magnesium and 1 silver
An electrode having a film thickness of 1500 angstrom was formed from the alloy mixed at 0: 1 to obtain the organic EL device shown in FIG. With this device, light emission of about 35 cd / m ² was obtained at a DC voltage of 10 V.

Example 2 An organic EL device was prepared by forming a light emitting layer of the compound (2) on a washed glass plate with an ITO electrode by a vacuum deposition method. The light emitting layer was vapor-deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. An electrode having a film thickness of 1500 angstrom was formed on it by an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain the organic EL device shown in FIG. With this device, light emission of about 35 cd / m ² was obtained at a DC voltage of 10 V.

Example 3 On a cleaned glass plate with ITO electrodes, N, N'-diff
Phenyl-N, N '-(3-methylphenyl) -1,1'-
Vacuum deposition of biphenyl-4,4'-diamine to give 30
A hole injection layer having a film thickness of 0 angstrom was obtained. Next
Then, the film thickness of the compound (2) is 500 angstrom by the vacuum deposition method.
Create a luminescent layer of strom and on top of it magnesium
1500 angstrom with alloy of 10: 1 and silver
To form an electrode having a film thickness of the organic EL element shown in FIG.
Obtained. 10 for the hole injection layer and the light emitting layer ^-6Torr vacuum
In, vapor deposition was carried out under the condition that the substrate temperature was room temperature. This element is
Approximately 280 cd / m at a DC voltage of 10 V²Emission of
It was From this result, the compound of the present invention emits electrons.
It turns out that it is a light substance.

Example 4 On a cleaned glass plate with an ITO electrode, N, N'-diff
Phenyl-N, N '-(3-methylphenyl) -1,1'-
Vacuum deposition of biphenyl-4,4'-diamine to give 30
A hole injection layer having a film thickness of 0 angstrom was obtained. Next
Then, the film thickness of the compound (6) is 500 angstrom by the vacuum deposition method.
Create a luminescent layer of strom and on top of it magnesium
1500 angstrom with alloy of 10: 1 and silver
To form an electrode having a film thickness of the organic EL element shown in FIG.
Obtained. 10 for the hole injection layer and the light emitting layer ^-6Torr vacuum
In, vapor deposition was carried out under the condition that the substrate temperature was room temperature. This element is
Approximately 210 cd / m at a DC voltage of 10 V²Emission of
It was From this result, the compound of the present invention emits electrons.
It turns out that it is a light substance.

Example 5 N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-on a cleaned glass plate with ITO electrodes
Vacuum deposition of biphenyl-4,4'-diamine to give 30
A hole injection layer having a film thickness of 0 angstrom was obtained. Then, the 8-aluminum quinolinol complex 10 is formed by vacuum deposition.
0 parts and 5 parts of the compound (6) were co-evaporated in a vacuum of 10 ⁻⁶ Torr to form a light emitting layer having a film thickness of 500 Å, and an alloy in which magnesium and silver were mixed at a ratio of 10: 1 was 1500 angstrom. An electrode having a film thickness of 1 was formed to obtain the organic EL device shown in FIG. The device emitted light of about 520 cd / m ² at a DC voltage of 10 V.

Comparative Example 1 N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-on a cleaned glass plate with an ITO electrode.
Vacuum deposition of biphenyl-4,4'-diamine to give 30
A hole injection layer having a film thickness of 0 angstrom was obtained. Then, the 8-aluminum quinolinol complex was formed into 1 by vacuum evaporation.
Co-depositing in a vacuum of 0 ^-6 Torr to form a light emitting layer having a film thickness of 500 Å, and forming an electrode having a film thickness of 1500 Å with an alloy obtained by mixing magnesium and silver at a ratio of 10: 1, The organic EL device shown in FIG. 2 was obtained. The device emitted light of about 120 cd / m ² at a DC voltage of 10 V.

From the results of Example 5 and Comparative Example 1, it was found that the emission brightness can be greatly improved by doping the compound of the present invention into the light emitting layer as a light emission assisting material for other known light emitting substances. It was Furthermore, 1 mA / c
After continuous light emission at m ² , it was found that the light emission time was improved by 5 times or more.

Example 6 N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-on a cleaned glass plate with ITO electrodes
Biphenyl-4,4'-diamine was vacuum-deposited to obtain a hole injection layer having a film thickness of 300 Å. Then
A light-emitting layer having a film thickness of 200 Å of the compound (23) was formed by a vacuum evaporation method, and further, [2- (4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxa was formed by a vacuum evaporation method. Diazole] film thickness 20
A 0 angstrom electron injection layer was obtained. On top of that, an alloy of magnesium and silver mixed at a ratio of 10: 1 has a film thickness of 150.
An organic E shown in FIG. 3 is formed by forming a 0 angstrom electrode.
An L element was obtained. This device has about 340
Light emission of cd / m ² was obtained.

When all the organic EL devices shown in this example were made to continuously emit light 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 improvement in luminous efficiency, luminous brightness, and long life.
Luminescent auxiliary material, hole transport material, electron transport material, sensitizer,
The resin, the electrode material and the like and the method for manufacturing the element are not limited.

[0046]

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

[0047]

[Brief description of drawings]

FIG. 1 is a sectional view showing a schematic structure of an organic EL element used in Examples 1 and 2.

FIG. 2 is a cross-sectional view showing a schematic structure of an organic EL element used in Examples 3, 4, 5 and Comparative Example 1.

FIG. 3 is a cross-sectional view showing a schematic structure of an organic EL device used in Example 6.

[Explanation of symbols]

 1. Substrate 2. Electrode A 3. Hole injection layer 4. Light emitting layer 5. Electron injection layer 6. Electrode B

Claims (2)

[Claims] 1. In an organic electroluminescence device comprising a light emitting layer composed of one or a plurality of organic compound thin films between a pair of electrodes, at least one layer is represented by the following general formula [1] and / or general formula [2]. An organic electroluminescence device comprising a layer containing the compound shown. General formula [1] General formula [2] [In the formula, A and B are each independently a substituted or unsubstituted aliphatic ring group, a substituted or unsubstituted carbocyclic aromatic ring group, a substituted or unsubstituted heterocyclic aromatic ring group,
It represents a substituted or unsubstituted heterocyclic group. -X ^1- , -X ²
-, = Y ¹ and = Y ² are each independently O, S, S
e, Te, NR ¹ or PR ² is shown. R ¹ and R ² are
Independently of each other, hydrogen atom, halogen atom, cyano group,
Nitro group, amino group, ester group, mono- or di-substituted amino group, acylamino group, hydroxyl group, alkoxy group, 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 aliphatic ring group, substituted or unsubstituted carbocyclic aromatic ring group, substituted or It represents an unsubstituted heterocyclic aromatic ring group or a substituted or unsubstituted heterocyclic group. ] 2. In an organic electroluminescence device having a light emitting layer composed of one or a plurality of layers of an organic compound thin film between a pair of electrodes, the light emitting layer is represented by the general formula [1] and / or the general formula [2]. It is a layer containing a compound, The organic electroluminescent element of Claim 1 characterized by the above-mentioned.