JPH11354278A - Organic electroluminescence element material and organic electroluminescence element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a highly efficient blue luminescent element for which a dope coloring matter is not used by making compound of bisamino styryl benzene derivative compound as an element material and making it possible utilize the material as a blue luminescent material with excellent color purity or a material having both functions of a positive hole transport and luminescence. SOLUTION: As for compound shown by a formula, all hydrogen on a benzene ring are substituted, fluorescence of a shorter wavelength is provided and, preferably, a fluorescence maximum wavelength is determined for 480 nm or below. In the formula, R<1> to R<4> : substitutional groups, R<5> to R<8> : hydrogen or substitional groups, Ar<1> , Ar<2> : aromatic bonding groups and Ar<3> to Ar<6> : aromatic groups are shown. It is desirable that R<1> to R<4> are alkyl groups, R<5> to R<6> are hydrogen atoms and further Ar<1> , Ar<2> are non-substitution phenylene groups. It is desirable that this compound is an organic EL element having a luminescent layer or a laminated body of a plurality of organic layers including the luminescent layers between a cathode and an anode and one or more layers having this compound are constituted to have both functions of a positive hole transport and luminescence. The compound as low molecular compound is allowable and may be used as the skeleton of a principal chain of high molecular compound or a bonding remaining group of a polymer principal chain.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device material of a bisaminostyrylbenzene derivative and an organic electroluminescence (hereinafter abbreviated as "EL") device using the same.

[0002]

2. Description of the Related Art At present, research and development on various display elements are active. Among them, an organic EL element is capable of obtaining high-luminance light emission at a low voltage, and is attracting attention as a promising display element. For example, an EL element which forms an organic thin film by vapor deposition of an organic compound is known (Applied Physics Letters, vol. 51, p. 913, 1987).
Year). This organic EL device has a laminated structure of an electron transporting material and a hole transporting material, and its luminous characteristics are greatly improved as compared with a conventional single-layer type device.

As a means for improving the luminous efficiency of the stacked EL device, a method of doping a fluorescent dye is known. For example, the organic EL device doped with a coumarin dye described in Journal of Applied Physics, Vol. 65, p. 3610, 1989 has a remarkably improved luminous efficiency as compared with a non-doped device.

In general, in an organic EL device, the emission color required depends on the application, but light of a desired wavelength can be extracted by changing the type of fluorescent dye used. For example, in consideration of use as a full-color display, a backlight, and an illumination light source, three primary colors or white are required. In order to emit three primary colors or white light, light emission in the blue part is essential. However, there is a problem that the number of fluorescent dyes that emit light in the blue part with high efficiency and excellent durability is small.

In organic EL devices such as the above-mentioned stacked devices, it is important to develop an effective hole transport material. For example, the bisaminostyrylbenzene derivative described in JP-A-7-216351 is an effective hole transporting material because it has a higher molecular weight and a higher Tg than a monosubstituted benzene derivative. It is a compound that emits blue-green to green fluorescence. Even if a layer containing this benzene derivative is doped with a blue light-emitting dye, it is theoretically difficult to obtain blue light emission, and improvement has been demanded.

Also, an EL using the above-mentioned doped dye is used.
Although the luminous efficiency of the device is greatly improved, the suitability for production is low, such as the necessity of incorporating a very small amount of dye into the device, and when a small amount of doped dye is decomposed over time, the device characteristics are greatly deteriorated. There's a problem. The above problem can be solved if a compound having both functions of a host material such as a hole transport material and a light emitting material that emits light of a desired color can be solved, but in general, when the concentration of such a compound is increased, the concentration of the compound increases. There has been a problem that the luminous efficiency is greatly reduced due to the association of compounds, the formation of exciplexes, and the like.

[0007]

SUMMARY OF THE INVENTION The object of the present invention is to develop a compound which has both functions as a blue light-emitting dye and a hole transport material and has high luminous efficiency in view of the above-mentioned conventional situation. Another object of the present invention is to provide an EL device material and an EL device having high luminous efficiency without using a doped dye by using the compound.

[0008]

In order to achieve the above object, an EL device material and an EL device according to the present invention have the following constitutions. An organic electroluminescent device material, which is a compound represented by the general formula (1).

[0009]

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[0010] (wherein, R ¹ to R ⁴ represents a substituent, R ⁵
To R ⁸ represents a hydrogen atom or a substituent. Ar ¹ , Ar ²
Represents an aromatic linking group. Ar ^{3 to} Ar ⁶ represent an aromatic group. An organic electroluminescent device comprising at least one compound represented by the general formula (1).

[0011] (wherein, R ¹ to R ⁴ represents a substituent, R ⁵
To R ⁸ represents a hydrogen atom or a substituent. Ar ¹ , Ar ²
Represents an aromatic linking group. Ar ^{3 to} Ar ⁶ represent an aromatic group. The organic electroluminescent device as described above, wherein R ^{1 to} R ^{4 in} the general formula (1) are an alkyl group. The organic electroluminescent device according to the above or the above, wherein R ^{5 to} R ^{8 in} the general formula (1) are hydrogen atoms. The organic electroluminescent device according to any one of the above and the above, wherein Ar ¹ and Ar ^{2 in} the general formula (1) are phenylene groups. The fluorescence maximum wavelength (λ) of the compound represented by the general formula (1)
max) is 480 nm or less, the organic electroluminescent element according to any one of the above and the above. The organic electroluminescent device according to any one of the above, wherein the organic electroluminescent device has at least one single compound layer of the general formula (1), and the layer has both functions of hole transport and light emission. Luminescent element. Wherein the organic layer has a laminated structure,
The organic electroluminescent device according to any one of the above.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by the above general formula (1) will be described in detail. R ^{1 to} R ⁴ represent a substituent. Examples of the substituent include, for example, an alkyl group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms,
Particularly preferably, it has 1 to 8 carbon atoms, and examples thereof include methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, and particularly preferably having 2 carbon atoms.
-8, for example, vinyl, allyl, 2-butenyl, 3
-Pentenyl and the like. ), An alkynyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 1 carbon atoms)
2, particularly preferably having 2 to 8 carbon atoms, such as propargyl and 3-pentynyl. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, and naphthyl). Carbonyl group (preferably having 1 carbon atom
-20, more preferably 1-16 carbon atoms, particularly preferably 1-12 carbon atoms, such as acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl,
Dimethylaminocarbonyl, phenylaminocarbonyl and the like can be mentioned. ), A substituted amino group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, dimethylamino,
Examples include methylcarbamoyl, ethylsulfonylamino, dimethylaminocarbonylamino, phthalimide and the like. ), A sulfonyl group (preferably having 1 to 2 carbon atoms)
It has 0, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl. ), A sulfo group, a carboxyl group, a heterocyclic group (preferably containing any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, and particularly preferably carbon Formulas 2 to 12, for example, imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl group, etc.), hydroxy group, alkoxy group (preferably having 1 to 20 carbon atoms, more preferably carbon atom) Number 1
To 16, particularly preferably 1 to 12 carbon atoms, for example, a methoxy group, a benzyloxy group and the like. ), An aryloxy group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 16 carbon atoms, and particularly preferably having 6 to 12 carbon atoms.
And examples thereof include a phenoxy group and a naphthyloxy group. ), A halogen atom (preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a thiol group,
Alkylthio group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms)
And an arylthio group (preferably having 6 to 20 carbon atoms, more preferably having 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, for example, a phenylthio group and the like). ) And a cyano group. These substituents may be further substituted, and R ¹ and R ² groups or R ³ and R ⁴ groups may be linked to form an unsaturated ring.

Among the substituents represented by R ^{1 to} R ⁴ , preferably a substituted or unsubstituted alkyl group or aromatic group (for example, an aryl group, an aromatic heterocyclic group (preferably having 1 to carbon atoms) 50, more preferably 1 to 30 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as a pyridyl group, a quinolyl group, a thiophene group, a carbazolyl group and an oxadiazolyl group)), particularly preferably substituted or unsubstituted And more preferably a methyl group.

R ^{5 to} R ⁸ represent a hydrogen atom or a substituent. Examples of the substituent include, for example, the examples of the substituent described above for R ¹ . R ^{5 to} R ⁸ are preferably a hydrogen atom, an alkyl group, a cyano group, or an aromatic group, particularly preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

Ar ¹ and Ar ² are aromatic linking groups (preferably having 1 to 36 carbon atoms, particularly preferably having 2 to 2 carbon atoms).
4, more preferably 3 to 12 carbon atoms. Examples thereof include a phenylene group, a naphthylene group, an anthracenylene group, a pyridylene group, a thienylene group and the like. These linking groups may further have a substituent. Ar ¹ may be linked to Ar ³ or Ar ⁴ directly or on a substituent to form a nitrogen-containing heterocycle. Ar ² may be linked to Ar ⁵ or Ar ⁶ directly or on a substituent to form a nitrogen-containing heterocycle. Ar ¹ and Ar
² is preferably a substituted or unsubstituted phenylene group or a pyridylene group, particularly preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group.

Ar^Three~ Ar⁶Is an aromatic group (preferably charcoal
Prime number 1 to 36, particularly preferably carbon number 2 to 24, furthermore
It preferably represents 3 to 12 carbon atoms). Examples of this aromatic group
As the R¹Examples of the aromatic groups mentioned in
You. Ar^ThreeAnd Ar^FourAnd Ar ^FiveAnd Ar⁶Is directly or
It may be linked on a substituent to form a ring. Ar^Three~ Ar
⁶Is preferably a substituted or unsubstituted phenyl group,
Tyl, pyridyl, pyrenyl, and anthracenyl groups
And particularly preferably substituted or unsubstituted phenyl.
And naphthyl and pyridyl groups.
Or a substituted or unsubstituted phenyl group.

The compound represented by the general formula (1) may be a low molecular weight compound or a high molecular weight compound in which the residue represented by the general formula (1) is connected to the polymer main chain (preferably, by weight). Average molecular weight of 1,000 to 5,000,000, particularly preferably 5,000 to 2,000,000, more preferably 1
0000-1,000,000) or a high molecular weight compound having a skeleton of the general formula (1) in the main chain (preferably a weight average molecular weight of 1,000 to 5,000,000, particularly preferably 50
00 to 2,000,000, more preferably 10,000 to
1,000,000). In the case of a high molecular weight compound, it may be a homopolymer or a copolymer with another monomer. The compound represented by the general formula (1) is preferably a low molecular weight compound.

Examples of the compound represented by the general formula (1) are shown below, but the present invention is not limited thereto.

[0019]

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[0020]

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[0021]

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[0022]

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The compound represented by the general formula (1) can be produced by a known synthesis method.

Next, an EL device containing the compound represented by the general formula (1) of the present invention will be described. The method for forming the organic layer of the EL element containing the bisaminostyrylbenzene derivative compound represented by the general formula (1) of the present invention is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, and molecular. Methods such as a lamination method and a coating method are used, and resistance heating evaporation and a coating method are preferable in terms of characteristics and production.

The EL device of the present invention is a device in which a light emitting layer or a plurality of organic compound thin films (organic layers) including a light emitting layer are formed between a pair of anode and cathode electrodes. , A hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers may have another function. Various materials can be used for forming each layer.

The laminated structure of the EL device of the present invention includes, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer,
An element configuration having an electron injection layer may be mentioned, and a single compound may serve as a plurality of layers. Although the layer configuration of the element is not particularly limited, for example, the element configuration has a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in this order.

The anode supplies holes to the hole injecting layer, the hole transporting layer, the light emitting layer, and the like. A metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof is used. And is preferably a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (hereinafter abbreviated as “ITO”), or gold, silver, chromium,
Metals such as nickel, and mixtures or laminates of these metals and conductive metal oxides; inorganic conductive substances such as copper iodide and copper sulfide; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; and ITO
And the like, and a conductive metal oxide is preferable, and ITO is particularly preferable in terms of productivity, high conductivity, transparency, and the like. The thickness of the anode can be appropriately selected depending on the material, but is preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm to 500 nm.

As the anode, a layer formed on a soda lime glass, an alkali-free glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass in order to reduce ions eluted from the glass. Further, when soda lime glass is used, it is preferable to use a glass coated with a barrier coat such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength. When glass is used, the thickness is usually 0.2 mm or more, preferably 0.7 mm or more.

Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (such as a sol-gel method), and a coating of an ITO dispersion are used. The film is formed by the method described above. In addition, the anode can reduce the driving voltage of the element or increase the luminous efficiency by washing or other treatment. For example, in the case of ITO, UV-ozone treatment, plasma treatment and the like are effective.

The cathode supplies electrons to the electron injecting layer, the electron transporting layer, the light emitting layer, etc., and provides the adhesion between the negative electrode such as the electron injecting layer, the electron transporting layer, the light emitting layer and the ionization potential. , Stability and the like. As the material of the cathode, metals, alloys, metal halides, metal oxides, electrically conductive compounds, or mixtures thereof can be used, and specific examples thereof include alkali metals (eg, Li, Na, K, etc.) and Fluoride, alkaline earth metal (eg, Mg, Ca, etc.) and its fluoride, gold,
Silver, lead, aluminum, sodium-potassium alloy or a mixed metal thereof, lithium-aluminum alloy or a mixed metal thereof, magnesium-silver alloy or a mixed metal thereof, indium, rare earth metals such as ytterbium and the like, preferably It is a material having a work function of 4 eV or less, more preferably aluminum, lithium-
An aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof, or the like is used. The cathode is
Not only a single-layer structure of the compound and the mixture but also a stacked structure including the compound and the mixture can be employed.
The thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm.
m to 1 μm.

The cathode is manufactured by a method such as an electron beam method, a sputtering method, a resistance heating evaporation method, a coating method, and the like. The metal can be evaporated alone or two or more components can be evaporated at the same time. Furthermore, a plurality of metals can be vapor-deposited at the same time to form an alloy electrode, or a previously prepared alloy may be vapor-deposited. Further, the sheet resistance of the anode and the cathode is preferably low, and several hundred Ω / □
The following is preferred.

The material of the light emitting layer is capable of injecting holes from an anode or a hole injection layer or a hole transport layer and applying electrons from a cathode or an electron injection layer or an electron transport layer when an electric field is applied. Any material can be used as long as it can form a layer having a function, a function of transferring injected charges, and a function of providing a field of recombination of holes and electrons to emit light. A preferred light emitting layer contains the bisaminostyrylbenzene derivative represented by the general formula (1) of the present invention, but other light emitting materials can be used in combination.
Examples of other light emitting materials include benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives Oxadiazole derivative, aldazine derivative, pyrazine derivative, cyclopentadiene derivative, bisstyrylanthracene derivative, quinacridone derivative, pyrrolopyridine derivative, thiadiazolopyridine derivative, cyclopentadiene derivative, styrylamine derivative, aromatic dimethylidin compound, 8-quinolinol Polythiophene, polyphenylene, polyphenylene vinylene, such as metal complexes of derivatives and various metal complexes represented by rare earth complexes And the like of the polymer compound. The combination ratio of the bisaminostyrylbenzene derivative and the other light emitting material can be appropriately selected as needed. The thickness of the light emitting layer is not particularly limited, but is usually 1
It is preferably in the range of nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 50 μm.
0 nm.

The method of forming the light emitting layer is not particularly limited, but includes resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip coating, etc.), and LB method. A method such as resistance heating evaporation and a coating method are preferred.

The material of the hole injection layer and the hole transport layer has one of a function of injecting holes from the anode, a function of transporting holes, and a function of blocking electrons injected from the cathode. Anything should do. Specific examples thereof include bisaminostyrylbenzene derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, and pyrazolones represented by the general formula (1) of the present invention. Derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrins -Based compounds, polysilane-based compounds, poly (N-vinylcarbazole) derivatives, aniline-based copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene And the like. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. . The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. In the present invention, the bisaminostyrylbenzene derivative represented by the general formula (1) may be contained in any one of the hole injection layer, the hole transport layer, and the light emitting layer. May be contained in any of them.

As a method for forming the hole injection layer and the hole transport layer, a vacuum evaporation method and an LB method, and a method in which the material of the hole injection layer and the hole transport layer is dissolved or dispersed in a solvent and coated (spinning). Coating method, casting method, dip coating method, etc.). In the case of a coating method, the material can be dissolved or dispersed in a solvent together with a resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, and polyphenylene oxide. , Polybutadiene,
Poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. .

The material of the electron injecting layer and the electron transporting layer is not limited as long as it has a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode. Good. Specific examples thereof include triazole derivatives, oxazole derivatives, oxadiazole derivatives,
Heterocyclic tetracarboxylic anhydrides such as fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene perylene, and phthalocyanine derivatives And various metal complexes typified by metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as ligands. The thickness of the electron injection layer and the electron transport layer is not particularly limited, but is usually 1 nm to 5 μm.
The range is preferably 5 nm to 1 μm.
m, and more preferably 10 nm to 500 nm. The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-mentioned materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

As the method for forming the electron injection layer and the electron transport layer, a vacuum evaporation method, an LB method, and a method in which the materials for the electron injection layer and the electron transport layer are dissolved or dispersed in a solvent and coated (spin coating method, cast method) Method, dip coating method, etc.). In the case of the coating method, the material can be dissolved or dispersed together with the resin component,
As the resin component, for example, those exemplified in the case of forming the hole injection layer and the hole transport layer can be applied.

As the material of the protective layer, elements such as moisture and oxygen are used.
A device that prevents elements that promote element degradation from entering the element
What is necessary is just to have a function. As a specific example
Is In, Sn, Pb, Au, Cu, Ag, Al, T
i, metal such as Ni, MgO, SiO, SiO_Two, Al_Two
O_Three, GeO, NiO, CaO, BaO, Fe_TwoO_Three,
Y _TwoO_Three, TiO_TwoMetal oxides such as MgF_Two, Li
F, AlF_Three, CaF_TwoSuch as metal fluoride, polyethylene
, Polypropylene, polymethyl methacrylate, poly
Imide, polyurea, polytetrafluoroethylene, poly
Lichlorotrifluoroethylene, polydichlorodifluoro
Roethylene, chlorotrifluoroethylene and dichlorodi
Copolymer with fluoroethylene, tetrafluoroethylene
Monomer containing at least one comonomer and at least one comonomer
Obtained by copolymerizing a product, cyclic in the copolymer main chain
Fluorinated copolymer having structure, water absorption of 1% or more
Substances, moisture-proof substances having a water absorption of 0.1% or less, and the like.
You.

The method for forming the protective layer is not particularly limited. For example, a vacuum evaporation method, a sputtering method, a reactive sputtering method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, a plasma polymerization method ( High frequency excitation ion plating), plasma CVD, laser CVD, thermal CVD, gas source CVD, and coating can be applied.

[0040]

EXAMPLES Specific examples of the present invention will be described below, but the embodiments of the present invention are not limited to these examples. [Synthesis of Compound (1-1) belonging to General Formula (1)]
As shown in the following reaction formula, 2 g of a bisphosphonic acid durene derivative (b) and 2.5 g of 4-formylphenyldiphenylamine (c) are dissolved in 20 ml of dimethylformamide, and 1.1 g of t-BuOK is added thereto. Stirred. Water was added to the reaction solution, and the precipitated solid was separated by filtration.
Washing with acetonitrile gave crude crystals. Crystallization was performed with chloroform / methanol to obtain 1.2 g of a white solid (1-1). When the fluorescence spectrum in chloroform was measured, it was 477 (nm) (1 mmol / l).

[0041]

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[Production and Evaluation of EL Element] Comparative Example 1 A washed ITO substrate was set in a vapor deposition apparatus, and TPD
(N, N'-diphenyl-N, N'-ditolyl-benzidine) and the following compound (a) were co-deposited at a ratio of 20: 1 to 40 nm, and then TAZ (1-phenyl-2- (pt-butyl) was evaporated. (Phenyl) -5-biphenyl-1,3,4-triazole was deposited to a thickness of 20 nm and Alq (tris (8-hydroxyquinolinato) aluminum) to a thickness of 40 nm.
mm) and a co-deposition of 50 nm of magnesium: silver = 10: 1 in a vapor deposition apparatus.
Was deposited. Using a source measure unit 2400 manufactured by Toyo Technica, a DC constant voltage was applied to the EL obtained above.
The light was applied to the element to emit light, and the luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation, and the emission wavelength was measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. When a voltage of 8 V was applied, ELmax: 505 (nm)
Green light emission of (x, y) = (0.20, 0.39) was obtained,
Its maximum luminance was 522 cd / m ² (13 V).

[0043]

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Comparative Example 2 40 mg of polyvinyl carbazole, PBD (2- (p-
t-butylphenyl) -5-biphenyl-1,3,4-
Oxadiazole) 12 mg, the above compound (a) 1 mg
Was dissolved in 2 ml of dichloroethane and spin-coated on the washed ITO substrate. The thickness of the formed organic thin film was about 130 nm. A mask (a mask having a light-emitting area of 5 mm × 5 mm) patterned on the organic thin film is provided, and magnesium: silver = 10: 1 is set to 50 n in a vapor deposition apparatus.
After co-evaporation, 50 nm of silver was evaporated. When a voltage of 12 V was applied, ELmax: 505 (nm) (x,
y) = (0.18, 0.38) green light emission was obtained, and its maximum luminance was 408 cd / m ² (19 V).

Example 1 A device was prepared and evaluated in the same manner as in Comparative Example 1, except that the compound (1-1) obtained in the above Synthesis Example was used instead of the compound (a) used in Comparative Example 1. When a voltage of 7 V was applied, ELm
ax: 470 (nm) (x, y) = (0.15, 0.1
3) Blue light emission was obtained, and the highest luminance was 1500 cd / m.
² (12 V).

Example 2 A device was prepared and evaluated in the same manner as in Comparative Example 2, except that the compound (1-1) used in the above Synthesis Example was used instead of the compound (a) used in Comparative Example 2. When a voltage of 12 V was applied, E
Lmax: 470 (nm) (x, y) = (0.14,
0.12) blue light emission, the highest luminance of which is 633 cd
/ M ² (21 V).

Example 3 A washed ITO substrate was placed in a vapor deposition apparatus, and the same compound (1-1) as in the above synthesis example was vapor-deposited to a thickness of 40 nm.
Z (1-phenyl-2- (pt-butylphenyl)-
20 n of 5-biphenyl-1,3,4-triazole
m, Alq (tris (8-hydroxyquinolinato) aluminum) was deposited to a thickness of 40 nm. A mask (a mask having a light-emitting area of 5 mm × 5 mm) patterned on an organic thin film is provided, and magnesium: silver = 10:
1 was co-evaporated to 50 nm, and then 50 nm of silver was evaporated. 1
When a voltage of 0 V was applied, ELmax: 471 (n
m) (x, y) = (0.15, 0.20) light emission is obtained,
Its maximum luminance was 961 cd / m ² (15 V).

Similarly, when an EL device containing a compound other than the above-mentioned compound (1-1) belonging to the bisaminostyrylbenzene derivative represented by the general formula (1) of the present invention was evaluated, light was emitted in the blue portion. It has been confirmed that the compound has such a function as a hole transport material.

The bisaminostyrylbenzene derivative of the present invention can be used as a light emitting material and a hole transporting material. When the bisaminostyrylbenzene derivative of the present invention is used,
It was found that an EL element having light emission in the blue portion could be manufactured.

[0050]

The bisaminostyrylbenzene derivative of the present invention represented by the general formula (1) is different from the conventional bisaminostyrylbenzene derivative in that the benzene ring is completely substituted. The bisaminostyrylbenzene derivative of the present invention has shorter-wavelength fluorescence than the bisaminostyrylbenzene derivative (for example, the compound (a)) used in the conventional EL device, and is used as a blue light emitting material having high color purity. Available. In addition, the compound can be used as a compound having both a hole transporting material and a light emitting material. By using the compound, a highly efficient blue light emitting device without using a doped dye can be manufactured.

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[Procedure amendment]

[Submission date] September 3, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Claim 1

[Correction method] Change

[Correction contents]

Embedded image (Wherein, R ^{1 to} R ⁴ represent a substituent, R ^{5 to} R ⁸ represent a hydrogen atom or a substituent, Ar ¹ and Ar ² represent an aromatic linking group, and Ar ^{3 to} Ar ⁶ represent an aromatic group. Represents a group.)

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0009

[Correction method] Change

[Correction contents]

[0009]

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Claims (8)

[Claims] 1. An organic electroluminescent device material, which is a compound represented by the general formula (1). Embedded image (Wherein, R ^{1 to} R ⁴ represent a substituent, R ^{5 to} R ⁸ represent a hydrogen atom or a substituent, Ar ¹ and Ar ² represent an aromatic linking group, and Ar ^{3 to} Ar ⁶ represent an aromatic group. Represents a group.) 2. An organic electroluminescence device comprising an organic layer containing at least one compound represented by the general formula (1) according to claim 1. 3. The organic electroluminescence device according to claim 2, wherein R ^{1 to} R ^{4 in} the general formula (1) are an alkyl group. 4. The organic electroluminescent device according to claim 2, wherein R ^{5 to} R ^{8 in} the general formula (1) are hydrogen atoms. 5. The organic electroluminescent device according to claim ² , wherein Ar ¹ and Ar ^{2 in} the general formula (1) are phenylene groups. 6. The organic compound according to claim 2, wherein the compound represented by the general formula (1) has a maximum fluorescence wavelength (λmax) of 480 nm or less. Electroluminescence element. 7. The composition according to claim 2, wherein the compound has at least one single compound layer of the general formula (1), and the layer has both functions of hole transport and light emission.
The organic electroluminescent device according to any one of the above. 8. The organic electroluminescent device according to claim 2, wherein the organic layer has a laminated structure.