JP2000012229A - Organic electroluminescent element material and organic electroluminescent element using same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a reliable organic electroluminescent element material and an organic electroluminescent element having high luminance and high luminous efficiency, and lowering degradation of the luminescence. SOLUTION: This organic electroluminescent element material is represented by the general formula, and it is used for the organic electroluminescent element. In the formula, Ar1 and Ar2 each is a substituted or nonsubstituted aryl group, and Ar3 is a substituted or nonsubstituted arylene group. Then, (n) is an integer of 1-10.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence (EL) device used for a flat light source and a display.

[0002]

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

[0003] Conventional organic EL devices have a higher driving voltage and lower luminous brightness and luminous efficiency than inorganic EL devices.
In addition, the characteristic deterioration was remarkable, and it had not been put to practical use.
2. Description of the Related Art In recent years, an organic EL in which a thin film containing an organic compound having high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less is laminated.
Devices have been reported and are of interest (see Applied Physics Letters, 51, 913, 1987). In this method, the metal chelate complex is converted into a phosphor layer,
High brightness green light emission is obtained by using an amine compound for the hole injection layer, and the brightness is 100 c at a DC voltage of 6 to 7 V.
d / m ² and maximum luminous efficiency of 1.5 lm / W,
Has performance close to the practical range. However, organic EL devices up to now have improved light emission intensity due to the improved structure, but do not yet have sufficient light emission luminance.
In addition, there is a major problem that the stability upon repeated use is poor.

[0004]

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

[0005]

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

[0006]

Embedded image

[Wherein, Ar ¹ and Ar ² represent a substituted or unsubstituted aryl group, and Ar ³ represents a substituted or unsubstituted arylene group. N is 1 to 1
Represents an integer up to 0. Further, the present invention relates to the above organic electroluminescent device material, wherein n is an integer of 1 to 4.

The present invention also relates to an organic electroluminescent device having a plurality of organic compound thin films including a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer containing the organic electroluminescent device material. Related to the element. In addition, the present invention relates to an organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material.

Further, the present invention relates to an organic electroluminescence device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, wherein at least one of the holes in the hole injection zone between the light emitting layer and the anode is as described above. The present invention relates to an organic electroluminescence device which is a layer containing a material for an organic electroluminescence device. It is.

[0010]

DETAILED DESCRIPTION OF THE INVENTION

Ar ¹ and Ar ^{2 in the} compound represented by the general formula [1] of the present invention represent a substituted or unsubstituted aryl group. Examples of the substituted or unsubstituted aryl group include a phenyl group, a 4-ethylphenyl group, a biphenyl group,
Methylbiphenyl group, 4-cyclohexylbiphenyl group, terphenyl group, quarterphenyl group, 4-chlorophenyl group, 3-nitrophenyl group, 4-cyanophenyl group, 4-methoxyphenyl group, 3-methylthiophenyl group, 3,5 -Dicyanophenyl, 4-trifluoromethoxyphenyl, o-, m-, and p-tolyl, xylyl, o-, m-, and p-cumenyl;
Mesityl group, 4-phenoxyphenyl group, 4- (α, α
-Dimethylbenzyl) phenyl group, 4- (N, N-dimethyl) aminophenyl group, 4- (N, N-diphenyl)
Aminophenyl group, pentalenyl group, indenyl group, naphthyl group, 5-methylnaphthyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthryl group, anthraquinolyl group, 3
-Methylanthryl group, phenanthryl group, triphenylene group, pyrenyl group, chrysenyl group, 2-ethyl-1-
Chrysenyl group, picenyl group, perylenyl group, 6-chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, colonenyl group, trinaphthenyl group, heptaphenyl group, heptaenyl group, Examples include a pyranthrenyl group and an ovalenyl group.

Ar ³ in the compound represented by the general formula [1] of the present invention represents a substituted or unsubstituted arylene group. Specific examples of the arylene group include Ar ¹ and A
arylene groups corresponding to an aryl group exemplified in the description of r ² and the like. A phenylene group and a naphthalene group are preferred in terms of availability of raw materials.

In the general formula [1] of the present invention, n is an integer from 1 to 10, preferably from 1 to 4, more preferably from 2 to 4.

Phenane of the compound represented by the general formula [1]
Tren ring, Ar¹, Ar^TwoAnd Ar ^ThreeThe above hydrogen atom is
It may be substituted by another substituent. Substituent type
The halogen atom, cyano group, nitro group,
Is an unsubstituted alkyl group, substituted or unsubstituted alkoxy
A substituted or unsubstituted alkylthio group,
Or unsubstituted amino group, substituted or unsubstituted alkyl
There is an amino group.

In the present invention, the compound represented by the general formula [1] can be synthesized, for example, by the following method. It is obtained by reacting bis (bromoaryl) phenanthrene with an aromatic diamine compound in a nitrobenzene solvent at 200 ° C. for 50 hours together with a catalyst such as potassium carbonate or copper.

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

[0017]

[Table 1]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

An organic EL device is a device in which a single or multilayer organic compound thin film is formed between an anode and a cathode. In the case of a single layer type, a light emitting layer is provided between an anode and a cathode. The light-emitting layer contains a light-emitting material, and additionally has a hole-injection material, a hole-transport material or an electron-injection material, and an electron-transport material for transporting holes injected from an anode or electrons injected from a cathode to the light-emitting material. May be contained. The electron injection material is a material capable of injecting electrons from the cathode, and the electron transport material is a material capable of transporting the injected electrons to the light emitting layer. The hole injection material is a material capable of injecting holes from the anode, and the hole transport material is a material capable of transporting the injected holes to the light emitting layer.

The multilayer type includes (anode / hole injection zone / light-emitting layer / cathode), (anode / light-emitting layer / electron injection zone / cathode),
(Anode / Hole injection zone / Emitting layer / Electron injection zone / Cathode)
There is an organic EL element stacked in a multilayer structure of the above.

The compound represented by the general formula [1] of the present invention is a compound having strong fluorescence in a solid state and has excellent electroluminescence properties, so that it can be used in a light emitting layer as a light emitting material. Further, by doping the compound of the general formula [1] as a doping material in the light emitting layer at an optimum ratio in the light emitting layer, it is possible to select a high light emitting efficiency and an optimum light emitting wavelength. Further, the compound of the general formula [1] can transport carriers such as holes or electrons, but can be used as a hole injecting layer because it has better hole transportability. When the hole injection zone is composed of two or more layers, it can be used for any hole injection layer.

By using a compound of the general formula [1] as a doping material (guest material) as a host material of the light emitting layer, an organic EL device having high emission luminance can be obtained.
The compound of the general formula [1] is desirably contained in the light emitting layer in a range of 0.001% by weight to 50% by weight relative to the host material, and more preferably 0.01% by weight to 1% by weight.
A range of 0% by weight is effective.

Examples of the host material usable in combination with the compound of the general formula [1] include a quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, triazole, imidazole, oxazole, oxazole Diazole,
Stilbene, butadiene, benzidine triphenylamine, styrylamine triphenylamine, diamine triphenylamine fluorenone, diaminoanthracene triphenylamine, diaminophenanthrene triphenylamine, anthraquinodimethane, diphenoquinone, thiadiazole, tetrazole, perylene Examples include tetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, triphenylene, anthrone, and derivatives thereof, and conductive polymer materials such as polyvinylcarbazole and polysilane.

Conversely, it is also possible to change the luminescent color by using the compound of the general formula [1] as a host material and using another doping material. Doping materials used with the general formula [1] 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 complexes, aminoquinoline metal complexes, imines, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene and the like, and derivatives thereof, but are not limited thereto. It is not something to be done.

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

The organic EL element has a multi-layer structure, so that a decrease in luminance and life due to quenching can be prevented. If necessary, a combination of two or more kinds of light emitting materials, doping materials, hole injecting materials for injecting carriers, and electron injecting materials can also be used. Also,
The hole injection layer, the light-emitting layer, and the electron injection layer may each be formed in a layer structure of two or more layers, and an element structure in which holes or electrons are efficiently injected from the electrode and transported in the layer is selected. You.

The conductive material used for the anode of the organic EL device preferably has a work function of more than 4 eV, and includes carbon, aluminum, vanadium, iron, cobalt,
Nickel, tungsten, silver, gold, platinum, palladium and the like and alloys thereof, ITO substrate, metal oxide such as tin oxide and indium oxide called NESA substrate, and organic conductive resin such as polythiophene and polypyrrole are used. . The conductive material used for the cathode is preferably one having a work function of less than 4 eV, such as magnesium, calcium, tin, lead, titanium, yttrium,
Lithium, ruthenium, manganese and the like and alloys thereof are used. Representative examples of the alloy include magnesium / silver, magnesium / indium, and lithium / aluminum, but are not limited thereto. The ratio of the alloy is controlled by the heating temperature, atmosphere, and degree of vacuum, and an appropriate ratio is selected. The anode and the cathode may be formed by two or more layers if necessary.

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

Each layer of the organic EL device according to the present invention can be formed by any of a dry film forming method such as vacuum evaporation and sputtering and a wet film forming method such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate thickness. If the film thickness is too large, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too small, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. Normal thickness is 5nm to 10μ
The range of m is suitable, but the range of 10 nm to 0.2 μm is more preferable.

In the case of the wet film forming method, a material for forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane or the like to form an organic compound thin film, but any solvent may be used. . In any of the thin films, a suitable resin or additive may be used to improve film forming properties, prevent pinholes in the film, and the like. Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and photoconductive materials such as poly-N-vinyl carbazole and polysilane. And conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

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

The electron injecting material has a capability of injecting 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 injecting excitons generated in the light emitting layer. Compounds that prevent transfer to a material and have excellent thin film forming ability are exemplified. For example, quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxadiazole, thiadiazole, tetrazole, perylenetetracarbon Acid, fluorenylidenemethane, anthraquinodimethane,
Examples include, but are not limited to, anthrones and derivatives thereof. Alternatively, an electron accepting substance may be added to the hole injecting material, and an electron donating substance may be added to the electron injecting material for sensitization.

In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device or silicon oil is sealed to protect the entire device. It is also possible.

[0044]

The present invention will be described in more detail with reference to the following examples. In this example, an organic E having an electrode area of 2 mm × 2 mm was used.
The characteristics of the L element were measured.

Method for synthesizing compound (1) In 5 g of nitrobenzene, 1.46 g of 9,10-bis (4-bromophenyl) phenanthrene, 1.52 g of diphenylamine, 3.1 g of potassium carbonate, and 0.1 g of copper powder were added.
13 g was added, and the mixture was heated and stirred at 200 ° C. for 50 hours under a nitrogen atmosphere. After cooling, the mixture was diluted with 30 g of water and extracted with ethyl acetate. After removing ethyl acetate, the residue was purified by column chromatography using silica gel, recrystallized, and then purified by sublimation (yield 0.7 g). The formation of the compound was confirmed by NMR, FD-MS, and IR.

Example 1 N, N '-(3) was placed on a washed glass plate with ITO electrodes.
-Methylphenyl) -N, N'-diphenyl-1,1-
Biphenyl-4,4-diamine (TPD) is vacuum deposited
Thus, a hole injection layer having a thickness of 20 nm was obtained. Then the compound
(1) is vapor-deposited to form a light-emitting layer having a thickness of 40 nm;
(8-Hydroxyquinoline) aluminum complex (Alq
3) was deposited to obtain an electron injection layer having a thickness of 30 nm. That
A film made of an alloy of magnesium and silver mixed at a ratio of 10: 1
An organic EL element was obtained by forming an electrode having a thickness of 100 nm. Correct
The hole injection layer and the light emitting layer are 10^-6In a Torr vacuum,
The deposition was performed under the condition of a plate temperature of room temperature. This element has a DC voltage of 5
Light emission luminance of 300 cd / m at V ^Two, Maximum light emission luminance 2100
0 cd / m^TwoBlue-green with luminous efficiency 2.6lm / W at 5V
Color emission was obtained. Next, 3 mA / cm^TwoAt a current density of
As a result of a life test in which this device was continuously lit,
Light emission of more than 1/2 of the degree is held for more than 10,000 hours
Was.

Examples 2 to 35 Organic EL devices were produced in the same manner as in Example 1 except that the compounds shown in Table 2 were used in place of the compound (1) in the light emitting layer. This device exhibited the emission characteristics shown in Table 2.

[0048]

[Table 2]

[0049]

Example 36 A compound (3) was vacuum-deposited on a washed glass plate with an ITO electrode to form a 100-nm-thick light-emitting layer, on which an alloy obtained by mixing magnesium and silver at a ratio of 10: 1 was used. An electrode having a thickness of 150 nm was formed to obtain an organic EL device. The light emitting layer and the cathode were deposited at a substrate temperature of room temperature in a vacuum of 10 ^-6 Torr. This element has a DC voltage of 5
Light emission luminance of 35 cd / m ² at V, maximum light emission luminance of 2200 c
Blue-green light with a luminous efficiency of 0.5 lm / W at d / m ² and 5 V was obtained. Next, as a result of a life test in which the device was continuously caused to emit light at a current density of 3 mA / cm ² , light emission of 1/2 or more of the initial luminance was maintained for 5000 hours or more.

Example 37 Compound (4) was vapor-deposited on a washed glass plate with an ITO electrode to form a hole injection layer having a thickness of 80 nm.
lq3 was deposited to obtain a light-emitting layer having a thickness of 20 nm. An electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. This element has a DC voltage of 5V
At 80 cd / m ² , maximum luminous luminance of 9000 cd
/ M ² , luminescence with a luminous efficiency of 1.0 lm / W at 5 V was obtained. Next, at a current density of 3 mA / cm ² , as a result of a life test in which the device was continuously illuminated, it was found that half of the initial luminance was obtained.
The above light emission was held for 3000 hours or more.

Example 38 A hole injection layer having a thickness of 50 nm was formed by vapor deposition of TPD on a washed glass plate with an ITO electrode.
3 was deposited to obtain a light emitting layer having a thickness of 20 nm. Compound (2
4) was vapor-deposited to form an electron injection layer having a thickness of 60 nm, and an electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. This element has a DC voltage of 5
Emission luminance of 110 cd / m ² at V, maximum emission luminance of 5000
Light emission with a luminous efficiency of 1.4 lm / W at cd / m ² and 5 V was obtained. Next, at a current density of 3 mA / cm ² , as a result of a life test in which the device was continuously lit, the initial luminance was 1%.
/ 2 or more light emission was maintained for 3000 hours or more.

Example 39 TPD was vacuum-deposited on a washed glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 20 nm. Then
N, N '-(4-methylphenyl) -N, N'-(4-n
-Butylphenyl) -phenanthrene-9,10-diamine and the compound (2) were deposited at a weight ratio of 100: 1 to form a light emitting layer having a thickness of 40 nm, Alq3 was deposited, and an electron injection layer having a thickness of 10 nm was formed. I got On top of that, an alloy in which aluminum and lithium are mixed at a ratio of 25: 1 has a thickness of 100 nm.
Was formed to obtain an organic EL device. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. This device has a light emission luminance of 320 cd / m ² at a DC voltage of 5 V, a maximum light emission luminance of 18000 cd / m ² ,
Light emission with a luminous efficiency of 2.8 lm / W at 5 V was obtained.
Next, as a result of a life test in which the device was continuously lit at a current density of 3 mA / cm ² , luminescence of １ ／ or more of the initial luminance was maintained for 10000 hours or more.

Example 40 TPD was vacuum-deposited on a cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 20 nm. Next, the compound (1) and rubrene were evaporated at a weight ratio of 100: 1 to form a light emitting layer having a thickness of 40 nm, and Alq3 was evaporated to obtain an electron injection layer having a thickness of 10 nm. An electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 ^-6 Torr at a substrate temperature of room temperature. This device has a luminance of 18 at a DC voltage of 5 V.
0 cd / m ² , maximum light emission luminance 17000 cd / m ² , 5 V
In this case, yellow luminescence with a luminous efficiency of 2.5 lm / W was obtained.
Next, as a result of a life test in which the device was continuously lit at a current density of 3 mA / cm ² , luminescence of １ ／ or more of the initial luminance was maintained for 10000 hours or more.

Examples 41 to 44 Organic EL devices were produced in the same manner as in Example 40 except that the compounds shown in Table 3 were used as the doping compounds in the light emitting layer. This device exhibited the emission characteristics shown in Table 3.

[0056]

[Table 3]

Example 45 On a washed glass plate with ITO electrodes, 4, 4 ', 4 "
-Tris [N- (3-methylphenyl) -N-phenyl
[Amino] triphenylamine by vacuum evaporation to a film thickness of 40
As a result, a hole injection layer having a thickness of nm was obtained. Then, 4,4'-bis [N
-(1-Naphthyl) -N-phenylamino] biphenyl
(Α-NPD) is vacuum deposited to form a second positive electrode having a thickness of 10 nm.
A hole injection layer was obtained. Further, the compound (1) is vacuum-deposited.
To form a light emitting layer having a thickness of 30 nm.
Methyl-8-hydroxyquinolinato) (1-phenolic
G) Vacuum deposition of gallium complex and electron injection with a thickness of 30 nm
An inlay is created, over which magnesium and silver are added 10: 1.
An electrode with a thickness of 150 nm is formed from the alloy mixed in
EL device was obtained. The hole injection layer and the light emitting layer are 10^{- 6}T
Vapor deposition was performed at a substrate temperature of room temperature in a vacuum of orr.
This device has a light emission luminance of 330 (cd / m) at a DC voltage of 5 V.
^Two), Maximum emission luminance 26000 (cd / m^Two), Luminous efficiency
A blue-green emission of 3.2 (lm / W) was obtained.

Examples 46 to 79 Organic EL devices were produced in the same manner as in Example 45, except that the compounds shown in Table 4 were used instead of the compound (1) in the light emitting layer. This device exhibited the emission characteristics shown in Table 4.

[0059]

[Table 4]

[0060]

Example 80 Compound (9) was placed on a washed glass plate with an ITO electrode.
Tris (8-hydroxyquinoline) aluminum complex,
TPD, polycarbonate resin (PC-A) 3: 2:
It was dissolved in tetrahydrofuran at a weight ratio of 3: 8, and a 100-nm-thick light-emitting layer was obtained by spin coating. An electrode having a thickness of 150 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. This device emits light at a luminance of 12 cd /
m ² , a maximum light emission luminance of 3100 cd / m ² , and light emission of 0.5 lm / W at 5 V were obtained. Next, 3 mA / c
As a result of a life test in which the device was continuously lit at a current density of m ² , luminescence of １ ／ or more of the initial luminance was maintained for 3,000 hours or more.

The organic EL device of the present invention achieves improvement in luminous efficiency, luminous brightness and long life, and is used together with a luminescent material, a doping material, a hole injection material, an electron injection material, and a sensitizer. It does not limit the agent, resin, electrode material and the like, and the element manufacturing method.

[0063]

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

Claims (5)

[Claims] 1. An organic electroluminescent device material represented by the following general formula [1]. General formula [1] [Wherein, Ar ¹ and Ar ² represent a substituted or unsubstituted aryl group, and Ar ³ represents a substituted or unsubstituted arylene group. N represents an integer of 1 to 10. ] 2. The method according to claim 1, wherein n is an integer from 1 to 4.
The organic electroluminescent device material according to the above. 3. An organic electroluminescent device having a plurality of organic compound thin films including a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer containing the organic electroluminescent device material according to claim 1. Luminescent element. 4. An organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material according to claim 1. Luminescent element. 5. An organic electroluminescence device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, at least one layer in a hole injection zone between the light emitting layer and the anode. The organic electroluminescent element which is a layer containing the organic electroluminescent element material of the above.