JPH07102251A - Material for organic electroluminescent device and organic electroluminescent device produced using the same - Google Patents

Abstract

PURPOSE:To obtain an org. electroluminescent device which is resistant to degradation and has high luminance and emissivity by using a compd. (e.g. phthalonitrile) coordinated to boron as the luminescent layer. CONSTITUTION:A boron compd. and a compd. coordinated to boron are stirred under heating in an org. solvent to give a compd. of formula I (wherein R<1> to R<6> are each H, halogen, alkyl, cyano, amino, hydroxyl, etc., provided the two adjacent groups may combine with each other to form a ring ; and X<1>, X<2> and X<3> are each-N= or-CR<7>= provided R<7> is the same as R<1> to R<6>). More specifically, boron trichloride, phthalonitrile, and chloronaphthalene are heated to give a compd. of formula II. The resulting compd. is used to form a luminescent layer on a glass plate having an ITO electrode, and on the luminescent layer is formed a thin-film electrode, thus giving an electroluminescent device with an emission of 80 cd/m<2> at 10V d.c. The compd. of formula I has a large hole transport capacity and is useful as a carrier transport substance both in a hole transport layer and in a luminescent layer.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to organic electroluminescence (EL) used for flat light sources, display devices and the like.
The present invention relates to a device material, and further relates to an organic EL device using the same.

[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, the metal chelate complex is added to the phosphor layer,
High-luminance green light emission is obtained by using an amine compound in the hole injection layer, and the luminance is several hundreds at a DC voltage of 6 to 7V.
It has cd / m ² and a maximum luminous efficiency of 1.5 lm / W, which is close to the practical range. However,
The organic EL devices to date have been improved in emission intensity due to the improved structure, but have not yet had 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.

[0004]

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 study by the present inventors, an organic EL element using at least one layer of the organic EL element material represented by the general formula [1] has high emission intensity and excellent stability in repeated use. The present invention has been found out.

[0005]

That is, the first invention is an organic electroluminescence device material characterized by being represented by the following general formula [1].

General formula [1]

[Chemical 2] [Wherein R ¹ to R ⁶ are each independently a hydrogen atom,
Halogen atom, alkyl group, 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 unsubstituted heterocyclic aromatic ring group, substituted or unsubstituted Represents a heterocyclic group. In addition, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted heterocyclic aromatic ring group, and a substituted or unsubstituted heterocyclic ring between adjacent substituents. May be formed. X ¹ , X ² and X ³ are each independently-
N = or -C (R ⁷⁾ is a =. R ⁷ is R ¹ to R ⁶
Means a substituent similar to. L is a halogen atom, a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted Alternatively, it represents an unsubstituted arylthio group. ]

The second invention is an organic electroluminescence device having a light emitting layer consisting of one or more organic compound thin films between a pair of electrodes, at least one of which contains a compound represented by the general formula [1]. It is an organic electroluminescence element which is a layer.

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

Examples of the group of the compound represented by the general formula [1] and the substituent atom or the substituent to be added to the group in the present invention 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, acetoxymethyl group, acetoxyethyl group, acetoxypropyl group,
Acetoxybutyl 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-yridenyl 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, 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-chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptaenyl Group, pyrantrenyl group, substituted or unsubstituted fused polycyclic hydrocarbon such as ovarenyl group, 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, quinoxalinyl 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,
Substituted or unsubstituted heterocyclic group such as 3-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 Group, pentyloxy group, hexyloxy group, stearyloxy group, phenoxy group, methylthio group, ethylthio group, propylthio group, butylthio group, sec-butylthio group, t
ert-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, dimethylsulfate Famoyl group, ethylsulfamoyl group, diethylsulfamoyl group, propylsulfamoyl group, butylsulfamoyl group, phenylsulfamoyl group, diphenylsulfamoyl group, methylcarbamoyl group, dimethylcarbamoyl group, ethylcarbamoyl group -Yl group, diethylcarbamoyl group, propylcarbamoyl group, butylcarbamoyl group, phenylcarbamoyl group, methylcarbonylamino group, ethylcarbonylamino group, propylcarbonylamino group, butylcarbonylamino group, phenylcarbonylamino group, methoxycarbonylamino group, ethoxy Carbonylamino 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,
It is not limited to these substituents. Further, these substituents may further have any substituent.

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

The compound of the present invention can be obtained by heating and stirring boron or a boron compound and a compound capable of coordinating with boron in a suitable organic solvent.

Any boron or boron compound may be used in the synthesis of the compound of the present invention, and examples thereof include boron halide, boron acetate, boron acetylacetonate, boron alkoxide and boron hydroxide. The compound capable of coordinating with boron may be any compound, and examples thereof include compounds such as phthalonitrile and aminoiminoisoindolenin. The catalyst used in the present invention may be any catalyst as long as it dissolves the raw materials and causes the reaction. For example, toluene, xylene, nitrobenzene, dimethyl sulfoxide, N,
Examples thereof include solvents such as N-dimethylformamide, 1-chloronaphthalene, quinoline, and sulfolane. It is also possible to use a base for accelerating the reaction, which is an inorganic base such as potassium carbonate, lithium hydroxide, sodium hydroxide, pyridine, picoline, triethylamine, N-methylpyrrolidine, 1 , 5-diazabicyclo [5,4,0] undecene (DBU). The reaction temperature is not particularly limited, but a temperature range of 100 ° C to 250 ° C, preferably 150 ° C to 220 ° C is preferable. The synthesized compound can be washed and purified with water, an acid, an alkali and an organic solvent such as methanol and acetone. Further, the purity of the compound can be improved by physical purification such as sublimation purification.

Representative examples of the compounds of the present invention are specifically shown in Table 1 below, but the present invention is not limited to the following representative examples.

[0014]

[Table 1]

[0015]

[0016]

[0017]

[0018]

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. There is also an organic EL device having a layer structure of (electrode A / light emitting layer / electron injection layer / electrode B), and the compound of the general formula [1] can be preferably used in this device structure. Since the compound of the general formula [1] has a large hole transporting ability, it can be used as a carrier transporting substance in any of the hole injecting layer 3 and the light emitting layer 4. Also,
In the light emitting layer, it is also possible to use it as a doping agent of an appropriate light emitting substance to promote the proper selection of the emission wavelength and the increase of the emission intensity.

In the light emitting layer 4 of FIG. 1, in addition to the compound of the general formula [1] 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 may be used. it can. The structure of FIG. 2 has a light emitting layer 4 and a 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. The compound of the general formula [1] found by the present invention can be optimally used in any device structure.

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.

The substrate 1 is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. Examples include transparent resins.

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 liquid 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 resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, urethane, polysulfone, polymethylmethacrylate, and polymethylacrylate, and poly-
Examples thereof include photoconductive resins such as N-vinylcarbazole and polysilane, and conductive resins such as polythiophene and polypyrrole.

This 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], a known light emitting substance, light emission auxiliary material, hole transporting material, or electron transporting material can be used.

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, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, poly Aryl alkane, stilbene, butadiene,
Benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and their derivatives, and polyvinylcarbazole,
There are polymer materials such as polysilane and conductive polymers,
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 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] of the present invention can be used in the light emitting layer or the hole injecting layer. Further, in addition to the compound of the general formula [1], at least one kind 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. Further, in order to improve the stability of the organic EL element obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the element or silicon oil or the like is enclosed to protect the entire element. It is also possible. As described above, in the present invention, since the compound of the general formula [1] is used for the organic EL element, 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. Organic E of the present invention
The L element may be applied to a flat panel display such as a wall-mounted TV, a light source for a copying machine or a printer, a light source for a liquid crystal display or instruments, a display plate, a marker lamp, etc. The value is enormous.

[0032]

EXAMPLES The present invention will now be described in detail based on examples. (Synthesis example) Method for synthesizing compound (7) 25 g of boron trichloride, 81.8 g of phthalonitrile and 400 g of 1-chloronaphthalene were placed in a cooled flask, heated under a nitrogen atmosphere and reacted at 170 ° C for 2 hours. Let After completion of the reaction, the mixture was cooled to room temperature and filtered with methanol and water to obtain 73.5 g of compound. The obtained compound was analyzed by mass spectrometry, infrared absorption spectrum, and NMR spectrum, and was found to be compound (7).

Example 1 Compound (7) was added onto a washed glass plate with an ITO electrode.
N, N'-diphenyl-N, N '-(3-methylphenyl) -1,1'-biphenyl-4,4'-diamine, poly-N-vinylcarbazole into chloroform at a ratio of 3: 2: 5. It was dissolved and dispersed, and a light emitting layer having a film thickness of 1000 angstrom was obtained by a spin coating method. On top of that, 1: 1 with an alloy of magnesium and silver mixed 10: 1
An electrode having a film thickness of 500 Å was formed to obtain the organic EL device shown in FIG. This element is DC voltage 10V
At that time, light emission of 80 cd / m ² was obtained.

Example 2 Compound (23) was applied onto a washed glass plate with an ITO electrode.
Was vacuum-deposited to obtain a hole injection layer having a film thickness of 300 Å. Then, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light emitting layer having a film thickness of 500 angstrom, and an electrode having a film thickness of 1500 angstrom is formed on the alloy by mixing magnesium and silver in a ratio of 10: 1. Was formed to obtain the organic EL device shown in FIG. The hole injecting layer and the light emitting layer were vapor-deposited in a vacuum of 10 ⁻⁶ Torr at a substrate temperature of room temperature. This element is
Light emission of about 320 cd / m ² was obtained at a DC voltage of 10 V.

Example 3 A hole transport layer having a film thickness of 200 angstroms of compound (29) was formed on a washed glass plate with an ITO electrode by spin coating, and a tris (8-hydroxyquinoline) aluminum complex was vacuum deposited. To form a light emitting layer having a film thickness of 500 angstroms, and further, a film thickness of [2- (4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxadiazole] 20 by a vacuum evaporation method.
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 a DC voltage of 10 V
Light emission of cd / m ² was obtained.

When all the organic EL devices shown in this example were made to emit light continuously 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.

[0037]

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.

[Brief description of drawings]

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

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

FIG. 3 is a sectional view showing a schematic structure of an organic EL element used in Example 3.

[Explanation of symbols]

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

Claims (3)

[Claims] 1. An organic electroluminescent device material represented by the following general formula [1]: General formula [1] [Wherein R ¹ to R ⁶ are each independently a hydrogen atom,
Halogen atom, alkyl group, 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 unsubstituted heterocyclic aromatic ring group, substituted or unsubstituted Represents a heterocyclic group. In addition, a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted heterocyclic aromatic ring group, and a substituted or unsubstituted heterocyclic ring between adjacent substituents. May be formed. X ¹ , X ² and X ³ are each independently-
N = or -C (R ⁷⁾ is a =. R ⁷ is R ¹ to R ⁶
Means a substituent similar to. L is a halogen atom, a hydroxyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted mercapto group, a substituted or unsubstituted alkyloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted Alternatively, it represents an unsubstituted arylthio group. ] 2. 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, wherein at least one layer is provided.
An organic electroluminescence device, which is a layer containing the organic electroluminescence device material described above. 3. An organic electroluminescence device comprising a light emitting layer consisting of one or a plurality of organic compound thin films between a pair of electrodes, wherein the hole injection layer is a layer containing the organic electroluminescence device material according to claim 1. An organic electroluminescence device characterized in that