JPH08298186A - Organic electroluminescence element material and organic electroluminescence element using this organic electroluminescence element material - Google Patents

Abstract

PURPOSE: To enhance emitting efficiency and emitting brightness in red color emission further to improve stability when used repeatedly, by using a prescribed compound as an element material. CONSTITUTION: In a compound as shown by a formula I or a formula II having strong fluorescence, besides using as an emitting material, doping is performed by optimum ratio in an emitting material of quinoline metal complex or the like in an emitting layer, and optimum selection of high emitting efficiency and emitting wavelength can be performed. This compound is contained desirably by 0.001 to 50wt.% the emitting material. [in the formula, R<1> to R<4> : hydrogen, halogen atom, amino group, mono or di substitution amino group, hydroxyl group, mercapt group, cyano group or substitution or non-substitution of the group, that is, namely alkyl group, alkoxy group, thioalkoxy group, aryloxy group, arylthio group, grease annular group, aromatic annular group, double group annular group, R<5> to R<10> : hydrogen or substitution or non-substitution of the group, that is, namely alkyl group, grease annular group, aromatic annular group, double group annular group, n is 0 to 2 integer].

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 element.

[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 100c at a DC voltage of 6 to 7V.
d / m ² , maximum luminous efficiency of 1.5 lm / W is achieved,
It has the performance close to the practical range. However, although the organic EL devices to date have improved the emission intensity due to the improved structure, they do not yet have sufficient emission brightness.
Further, it has a big problem that it is inferior in stability when repeatedly used.

In order to improve the light emission efficiency of an organic EL device, a technique of forming a light emitting layer by doping a host material as a light emitting material with a guest material has been disclosed. For example, tris (8-hydroxyquinoline) aluminum complex is used as a host substance in the light emitting layer, and coumarin dye or the like or 4-dicyanomethylene-2-methyl-6-p-dimethylaminostyryl-4H-pyran (DCM) dye is used for fluorescence. Organic EL device doped as a crystalline guest material (Journal of Applied Physics, vol. 65, page 3610, 1
989), but the luminous efficiency of these organic EL elements is not sufficient, and they are not suitable for red light emission applications for full color.

An organic EL device in which a tris (8-hydroxyquinoline) aluminum complex is used as a host substance and a quinacridone or a quinazoline compound is doped as a fluorescent guest substance in a light-emitting layer is disclosed (Japanese Patent Laid-Open No. 05-205).
-70773). However, these organic E
Although the initial light emission efficiency of the L element is improved, there is no change in the light emission color before and after doping, and there is a problem of deterioration when continuously emitting light, which is a serious problem in practical use. This is because it is difficult to do the technique of doping a small amount of the fluorescent guest substance in the light emitting layer, and in the disclosed quinacridone or quinazoline compound, pigment molecules are strongly aggregated in the light emitting layer. It is difficult to do so uniformly. For this reason, a fluorescent guest material that can be easily doped uniformly in the light emitting layer,
At present, there is a demand for the development of an organic EL device for red light emission, which has a high luminous efficiency and is excellent in stability during repeated use.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic EL device having high luminous efficiency, red light emission and excellent stability in repeated use. As a result of diligent studies by the present inventors, the organic EL device using at least one organic EL device material of the compound represented by the general formula [1] has a high red emission efficiency and stability during repeated use. The present invention has been found to be superior to the present invention.

[0007]

That is, the present invention relates to an organic electroluminescence device material which is a compound represented by the following general formula [1].

General formula [1]

[0009]

Embedded image

[In the formula, R ^{1 to} R ⁴ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, an amino group. , Mono- or di-substituted amino group, hydroxyl group, mercapto group, cyano group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted alicyclic group, substituted or unsubstituted aromatic ring Represents a group, a substituted or unsubstituted heterocyclic group (bonded by adjacent substituents to each other to form a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group R ⁵ and R ⁶ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted It represents a substituted aromatic ring group or a substituted or unsubstituted heterocyclic group. n shows the integer of 0-2. ]

Furthermore, the present invention relates to an organic EL device material comprising a compound represented by the following general formula [2].

General formula [2]

[0013]

[Chemical 4]

[In the formula, R ^{7 to} R ¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aromatic ring group,
Represents a substituted or unsubstituted heterocyclic group (adjacent substituents may be bonded to each other to form a substituted or unsubstituted heterocyclic group). ]

Further, the present invention is an organic EL device having a light emitting layer comprising a light emitting layer or a plurality of organic compound thin films including a light emitting layer between a pair of electrodes, at least one of which is represented by the general formula [1] or the general formula. The present invention relates to an organic EL device which is a layer containing the compound represented by [2].

Furthermore, the present invention is an organic EL device having a light emitting layer or a plurality of organic compound thin films including the light emitting layer formed between a pair of electrodes, wherein the light emitting layer is a quinoline metal complex and the general formula [1] or the general formula. Organic E represented by [2]
The present invention relates to an organic electroluminescence device which is a layer containing an L device material.

Typical examples of the substituent atom and the substituent bonded to the compound represented by the general formula [1] or the general formula [2] of the present invention are as follows. Examples of the hydrogen atom and halogen atom include fluorine, chlorine, bromine and iodine. The substituted or unsubstituted alkyl group includes a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group and a trichloromethyl group. , Trifluoromethyl group, cyclopropyl group, cyclohexyl group, 1,3-cyclohexadienyl group, 2-cyclopenten-1-yl group, 2,4-cyclopentadiene-1-yridenyl group and the like. Examples of the substituted or unsubstituted alkoxy group include methoxy group, ethoxy group, propoxy group, n-butoxy group, sec-butoxy group, te.
There are rt-butoxy group, pentyloxy group, hexyloxy group, stearyloxy group, trifluoromethoxy group and the like. As the substituted or unsubstituted thioalkoxy group,
Examples include methylthio group, ethylthio group, propylthio group, butylthio group, sec-butylthio group, tert-butylthio group, pentylthio group, hexylthio group, heptylthio group, octylthio group and the like.

Examples of the mono- or di-substituted amino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, diphenylamino group and bis (acetooxymethyl) group.
As a substituted or unsubstituted aryloxy group such as an amino group, a bis (acetooxyethyl) amino group, a bis (acetooxypropyl) amino group, a bis (acetooxybutyl) amino group, a dibenzylamino group, a phenoxy group, There are p-tert-butylphenoxy group, 3-fluorophenoxy group and the like. Examples of the substituted or unsubstituted arylthio group include a phenylthio group and a 3-fluorophenylthio group. Examples of the substituted or unsubstituted alicyclic group include cyclohexyl group, cyclooctyl group and 4-methylcyclohexyl group.

The substituted or unsubstituted aromatic ring group includes phenyl group, biphenylenyl group, triphenylenyl group, tetraphenylenyl group, 3-nitrophenyl group, 4
-Methylthiophenyl group, 3,5-dicyanophenyl group, o-, m- and p-tolyl group, xylyl group, formyl 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-chloroperenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group, hepta Examples include a phenyl group, a heptacenyl group, a pyrantrenyl group, an ovarenyl group and the like.

As the substituted or unsubstituted heterocyclic group,
Thionyl 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 , A flazanyl group, a phenoxazinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a 2-methylpyridyl group, a 3-cyanopyridyl group, and the like, but the substituents are not specifically limited.

The benzoxazine derivative represented by the general formula [1] or [2] is an α-keto acid or an α-keto acid.
-Obtained by cyclizing an aminophenol with a ketoester (Journal of Heterocyclic Chemistry, Vol. 22, p. 1275, 1985), and when adding a styryl or butadiene bond, a conventional synthetic method is used. However, the method is not limited to this method.

Representative examples of the compound of the present invention are specifically shown in Table 1, but the invention is not limited thereto.

[0023]

[Table 1]

[0024]

[0025]

[0026]

[0027]

[0028]

The organic EL element is an element in which a single-layer or multi-layer 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 the anode or electrons injected from the 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 multi-layer structure of (cathode), (anode / light emitting layer / electron injection layer / cathode), and (anode / hole injection layer / light emitting layer / electron injection layer / cathode). Since the compound of the general formula [1] or the general formula [2] has strong fluorescence, it can be used as a light emitting material. However, the compound of the general formula [1] or the general formula [2] is doped in the light emitting layer at an optimum ratio as a doping material. By doing so, high luminous efficiency and optimum selection of emission wavelength became possible.

A metal complex such as tris (8-hydroxyquinoline) aluminum complex is used as the light emitting material (host substance) of the light emitting layer, and a compound of the general formula [1] or general formula [2] is used as the light emission auxiliary material (guest substance). And has high emission brightness and excellent stability during repeated use.
An element can be obtained. The compound of the general formula [1] or the general formula [2] is preferably contained in the light emitting layer in an amount of 0.001% by weight to 50% by weight, and more preferably 0.01% by weight to the host substance. Wt% to 5 wt%
The range of is effective. The compound of the general formula [1] or the general formula [2] of the present invention has high solubility in a solvent in a wet film-forming method such as a spin coating method, and thus can be uniformly present in each layer used. . Therefore, for example, even when the light emitting material is doped in the light emitting layer, the carriers injected from the respective electrodes can be recombined uniformly in the light emitting layer, and the organic EL device has high brightness and long life. Is extremely effective for producing

In the light emitting layer, in addition to the light emitting material and the light emitting auxiliary material, a hole transporting material or an electron transporting material can be used if necessary.

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 injecting layer, the light emitting layer, and the electron injecting layer may each be formed of a layer structure of two or more layers, and a device structure in which holes or electrons are efficiently injected from the electrode and transported in the layer is selected. It

The conductive material used for the anode of the organic EL device 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 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. . The conductive material used for the cathode is preferably one having a work function smaller 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 to these. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.

In the organic EL element, it is desirable that at least one of them is sufficiently transparent in the emission wavelength region of the element in order to emit light efficiently. It is also desirable that the substrate is transparent. The transparent electrode is set using the above-mentioned conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate has mechanical and thermal strength and is not limited as long as it 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 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 5nm to 10μ
The range of m is preferred, but the range of 10 nm to 0.2 μm is more preferred.

In the case of the wet film-forming method, the material forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane to form a thin film.
The solvent may be any. Further, in any of the thin films, 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, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and poly-N-
Examples thereof include photoconductive resins such as vinylcarbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additives include antioxidants, ultraviolet absorbers, plasticizers and the like.

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, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran , Thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene and the like, and derivatives thereof, but are not limited thereto.

As the quinoline complex which is a light emitting material, a tris (8-hydroxyquinoline) aluminum complex is preferable, but in addition to this, bis (8-hydroxyquinoline).
Zinc, bis (8-hydroxyquinoline) magnesium,
Bis (benzo (f) -8-hydroxyquinoline) copper, bis (2-methyl-8-hydroxyquinoline) aluminum oxide, tris (8-hydroxyquinoline) gallium, tris (8-hydroxyquinoline) indium,
Tris (5-methyl-8-hydroxyquinoline) aluminum, 8-hydroxyquinoline lithium, tris (5
-Chloro-8-hydroxyquinoline) aluminum and the like.

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 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 an 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. Examples include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, thiadiazole, tetrazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane, anthrone, quinacridone and their derivatives. However, the present invention is not limited to these. 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] or the general formula [2] of the present invention is preferably used as a light emitting material or as a doping material in a light emitting layer, and is a light emitting material, a doping material, a hole transporting material. And at least one of the electron transport materials may be contained in the same layer.

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] or the general formula [2] is used for the organic EL device, the luminous efficiency 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 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 is a flat panel display such as a wall-mounted television, a light source such as a copying machine or a printer as a plane light emitting body, a light source such as a liquid crystal display or an instrument,
It is expected to be applied to display boards, marker lights, etc., and its industrial value is extremely large.

[0044]

The present invention will be described in more detail based on the following examples. Method for synthesizing compound (5) In a flask, 7-dimethylamino-3-methyl-1,
14. 10 g of 4-benzoxazin-2-one, 12 g of phthalaldehyde and 40 ml of acetic anhydride were added, and the mixture was heated and stirred at 140 ° C. for 4 hours, and the precipitated crystal was separated by filtration, washed with acetone, and dried to obtain pinkish red needle-like crystals. 8 g was obtained. Elemental analysis,
The compound (5) was confirmed by molecular weight analysis, infrared absorption spectrum and NMR spectrum.

Examples 1 to 30 On a cleaned glass plate with ITO electrodes, N, N '-(4
-Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine was vacuum-deposited to obtain a hole injection layer having a film thickness of 50 nm. Then, tris (8-hydroxyquinoline) aluminum complex and Table 1
The compound of the present invention described in 1. above is vacuum-co-evaporated at a weight ratio of 50: 1 to form a light-emitting layer having a film thickness of 50 nm.
An alloy of magnesium and silver mixed at a ratio of 10: 1 with a film thickness of 15
An electrode having a film thickness of 0 nm was formed to obtain an organic EL device. The hole injection layer, the light emitting layer and the cathode were vapor-deposited in a vacuum of 10 ⁻⁶ Torr and at a substrate temperature of room temperature. The results shown in Table 2 were obtained for this device at a DC voltage of 5V.

[0046]

[Table 2]

Example 31 N, N '-(4
-Methylphenyl) -N, N '-(4-n-butylphe
Nil) -phenanthrene-9,10-diamine under vacuum
After that, a hole injection layer having a film thickness of 50 nm was obtained. Then,
Lis (8-hydroxyquinoline) aluminum complex and book
The compound (5) of the invention was mixed with chloroform in a weight ratio of 50: 1.
Dissolve and disperse in a film and spin coating to a film thickness of 5
A 0 nm emission layer was obtained. On top of that, add magnesium and silver
An electrode with a thickness of 150 nm is formed from the alloy mixed at 10: 1
Then, an organic EL device was obtained. 1 for the hole injection layer and the cathode
0 ^-6Vapor deposition under conditions of substrate temperature and room temperature in Torr vacuum
did. This device emits red light at a DC voltage of 5V,
1300 cd / m²The emission luminance of was obtained.

Example 32 On a washed glass plate with an ITO electrode, tris (8-hydroxyquinoline) aluminum complex, compound (12) of the present invention, N, N '-(4-methylphenyl) -N, N'.
-(4-n-butylphenyl) -phenanthrene-9,
10-diamine and a polycarbonate resin (Teijin Kasei: Panlite L-1250) were dissolved and dispersed in chloroform at a ratio of 2: 0.05: 2: 5, and a light emitting layer having a thickness of 100 nm was obtained by spin coating. On top of that, an alloy in which magnesium and silver are mixed at a ratio of 10: 1 has a film thickness of 150 n.
An electrode of m was formed to obtain an organic EL device. 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. The device emitted red light at a DC voltage of 5 V and emitted light of 470 cd / m ² .

Example 33 N, N '-(4
-Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine was vacuum-deposited to obtain a hole injection layer having a film thickness of 50 nm. Next, the tris (8-hydroxyquinoline) aluminum complex and the compound (24) of the present invention are dissolved and dispersed in chloroform at a ratio of 100: 1, and a film thickness of 30 is obtained by spin coating.
nm emission layer is made, and magnesium and silver 1
An electrode having a thickness of 100 nm was formed from an alloy mixed with 0: 1 to obtain an organic EL element. 10 for the hole injection layer and the light emitting layer
Deposition was carried out in a vacuum of ^-6 Torr at a substrate temperature of room temperature. This device is observed to emit red light at a DC voltage of 5V, and
A light emission luminance of 220 cd / m ² was obtained.

Example 34 An organic EL device was manufactured in the same manner as in Example 33 except that only the compound (20) of the present invention was used as the light emitting material in the light emitting layer.
A device was created. The device emitted red light at a DC voltage of 5 V, and an emission luminance of 1050 cd / m ² was obtained.

Example 35 N, N '-(4
-Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine was vacuum-deposited to obtain a hole injection layer having a film thickness of 50 nm. Then, a tris (8-hydroxyquinoline) aluminum complex and the compound (27) of the present invention were formed in a ratio of 100: 1 by a vacuum co-evaporation method to form a light emitting layer having a film thickness of 30 nm, and further by a vacuum evaporation method [2- ( 4-tert-butylphenyl) -5
An electron injection layer having a film thickness of 20 nm of-(biphenyl) -1,3,4-oxadiazole] was obtained. An electrode having a film thickness of 150 nm was formed on it with an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL element. The hole injecting layer, the light emitting layer, the electron injecting layer, and the cathode were vapor-deposited under the conditions of the substrate temperature and room temperature in a vacuum of 10 ⁻⁶ Torr. This device emits red light at a DC voltage of 5 V and the emission is about 1780 cd / m ^2.
The emission luminance of was obtained.

When all the organic EL devices shown in this example were made to emit light continuously at 3 mA / cm ² , 10
Although stable light emission could be observed for more than 00 hours, the organic EL element of the comparative example manufactured under the same conditions had a luminance of less than half of the initial light emission luminance at an emission time of 300 hours or less, which is an effect of the organic EL element of the present invention. Was obvious. This is the general formula [1] or the general formula [2] used in the organic EL device of the present invention.
The compound (1) has extremely high solubility in a solvent and is therefore most suitable for wet film-forming methods such as spin coating and dipping. In addition, it is easy to evaporate when heated in vacuum, and therefore dry compounding such as vapor deposition and sputtering. As for the film, it is possible to form a uniform and smooth thin film. Therefore, the organic EL which is uniformly present in the light emitting material, can solve the decrease in light emitting efficiency due to concentration quenching, and has a high light emitting efficiency.
It has become possible to easily fabricate the device. The organic EL device of the present invention achieves improvement of luminous efficiency, luminous brightness and prolongation of life, and is used together with a luminescent substance, a doping material, a hole transporting material, an electron transporting material, a sensitizer and a resin. There is no limitation on the electrode material, etc. and the method for manufacturing the element.

[0053]

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. This is because by using the compound shown in the present invention in an organic EL device, wet and dry film forming methods are easy, and the compound is uniformly present in the light emitting material, and the decrease in light emission efficiency due to concentration quenching can be solved. , Organic E with high luminous efficiency
It has become possible to easily manufacture an L element.

Claims (4)

[Claims] 1. An organic electroluminescence device material, which is a compound represented by the following general formula [1]. General formula [1] [Wherein R ^{1 to} R ⁴ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, an amino group, a mono or A di-substituted amino group,
Hydroxyl group, mercapto group, cyano group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted alicyclic group, substituted or unsubstituted aromatic ring group, substituted or unsubstituted heterocyclic group Represents a ring group (may be bonded to adjacent substituents to form a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic group); R ⁵ , R ⁶
Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aromatic ring group, or a substituted or unsubstituted heterocyclic group. n shows the integer of 0-2. ] 2. An organic electroluminescence device material, which is a compound represented by the following general formula [2]. General formula [2] [Wherein, R ^{7 to} R ¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group. Represents a ring group (adjacent substituents may be bonded to each other to form a substituted or unsubstituted heterocyclic group). ] 3. An organic electroluminescence device having a light emitting layer or a plurality of organic compound thin films including a light emitting layer formed between a pair of electrodes, at least one layer of which is made of the organic electroluminescence device material according to claim 1 or 2. An organic electroluminescence device, which is a layer containing the organic electroluminescence device. 4. An organic electroluminescence device having a light emitting layer or a plurality of organic compound thin films including the light emitting layer formed between a pair of electrodes, wherein the light emitting layer is a quinoline metal complex and the organic electroluminescent device according to claim 1 or 2. An organic electroluminescence device, which is a layer containing a luminescence device material.