JP2001172284A - Organic light emission element material and organic light emission element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a specific silicon-containing hole transport compound and provide an organic light emission element having high luminance and excellent in durability by using the same. SOLUTION: This organic light emission element material is a compound having a silicon-containing structure expressed by general formula (1) (at least either one of X and Y is a hole transporting group; Z is an atomic group capable of forming a 3-8 membered silicon-containing ring; X, Y and Z may form a cyclic structure in which a part of the structure is mutually bonded). This organic light emission element is provided by using the same compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a specific silicon-containing hole transporting compound, an organic light emitting device material using the same, and an organic light emitting device.

[0002]

2. Description of the Related Art At present, research and development on various display elements are active. Among them, organic light emitting (EL) elements, which can obtain high-luminance light emission at a low voltage, have been attracting attention as promising display elements. I have. For example, an EL element that forms an organic thin film by vapor deposition of an organic compound is known (Applied Physiology).
cs Letters, 51, p. 913-, (1987)). The organic light-emitting device described in the document has a laminated structure of an electron transporting material and a hole transporting material, and its light-emitting characteristics are greatly improved as compared with a conventional single-layer type device. Examples of hole transport materials used in this stacked device include triarylamine derivatives represented by TPD (N, N'-di-m-tolyl-N, N'-diphenylbenzidine), pyrrole, carbazole Π-electron-rich aromatic compounds such as thiophene and thiophene are known as excellent hole transport materials. However, these compounds have high crystallinity, and it is known that an organic light emitting device using these compounds as a hole transport material has a problem in raw storage stability.
As a means for solving this problem, in the case of a triarylamine derivative, a technique of introducing a condensed polycyclic aromatic group or using a compound group with improved symmetry has been proposed by App.
l.Phys.Lett. 56 , 799 (1990), Polymer Preprints (ACS)
349 (1997). In addition, the same study was carried out for nitrogen-containing heterocyclic compounds such as carbazole derivatives, and a technique for polymerizing the compounds was disclosed in Appl.Phys.Lett. 63 , 2627 (1992).
3) etc. The inventors have also studied techniques for improving the deterioration of the raw storage stability of the organic light emitting device derived from the hole transport material.

[0003]

SUMMARY OF THE INVENTION It is an object of the present invention to develop a silicon-containing compound having a good hole-transporting ability and to produce an organic light-emitting device having high luminance and excellent storage stability of the device. To develop organic light emitting device materials.

[0004]

Means for Solving the Problems The present invention has been achieved by the following compounds, organic EL device materials and organic EL devices.

1) A compound represented by the general formula (1).

[0006]

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At least one of X and Y is a hole transporting group. Z is an atomic group capable of forming a 3- to 8-membered ring containing silicon. X, Y, and Z may form a cyclic structure in which a part of the structure is connected to each other. 2) The compound according to item 1, wherein in the compound represented by formula (1), at least one of the groups represented by X and Y contains a tertiary amine. 3) In the compound represented by the general formula (1), at least one of the groups represented by X and Y contains a condensed or non-condensed π-electron-rich aromatic heterocycle. 2. The compound according to item 1. 4) a compound represented by the general formula (1) according to any one of items 1 to 3,
Or, an organic light-emitting device material comprising a precursor thereof. 5) The organic light emitting device material according to item 4, wherein at least one of X, Y, and Z in the general formula (1) contains a polymerizable group and contains a polymer compound derived therefrom. 6) An organic light emitting device having at least one organic light emitting device material according to item 4 or 5. 7) The organic light-emitting device according to item 5 or 6, wherein at least one of the organic layers is formed by coating.

[0008]

DESCRIPTION OF THE PREFERRED EMBODIMENTS First, a compound represented by the general formula (1)
The compound will be described. Compound represented by general formula (1)
Is a silicon source where the hole transporting group is a part of a cyclic structure.
It is a compound having a structure substituted with a child. First, the hole transportability
X and Y, which are groups possessed, will be described. X and Y are silicon sources
Represents a substitutable group or atom, at least one of which
Represents a group having a hole transporting property. Preferably both
A group having a hole transporting property, and more preferably
They have the same structure. A group having a hole transporting property
The compounds to be provided include various structures in the art.
Compounds are known. For example, first of all, the first to third grade nitrogen sources
Compounds having an atom, that is, amine derivatives
You. Among them, aromatic hydrocarbon groups or heteroaromatics
Amines substituted by an aromatic ring group are preferred, and among them,
Tertiary amines whose substituents are all aromatic hydrocarbons
Compounds that are an amino group or a heteroaromatic ring group are preferred.
No. The following can be cited as heterogeneous electrons.
It is an aromatic compound. In this example, the heteroatom has a ring structure.
5-membered heteroaromatic contained in the structure, and
These are condensed with each other or with aromatic hydrocarbons
Can be mentioned. List one example
And, for example, pyrrole, thiophene, furan, indore
, Carbazole, benzothiophene, benzofuran,
Dibenzothiophene, dibenzofuran, indolizine
And so on. Furthermore, a compound having a nitrogen atom
As compounds, hydrazone compounds, pyrazolone compounds,
Droxylamine compound, alkoxyamine compound, etc.
Can also be used as a compound to provide a group having a hole transporting property
Noh. Next, the annular structure formed by Z is explained.
I do. Rings formed with Z that are characteristic of the compounds of the present invention
The state structure represents a 3- to 8-membered ring structure containing a silicon atom. This
The atoms that form the cyclic structure of
It may contain atoms. Give examples of its heteroatoms
And oxygen, nitrogen, sulfur, selenium, and phosphorus
Atom, silicon atom, boron atom, etc.
You. Among them, preferably, a silicon atom is part of its ring structure.
A hydrocarbon ring, or an oxygen atom, a nitrogen atom,
Or a silicon-containing heterocycle containing a sulfur atom. This
May be a ring having aromaticity. X, Y, Z
Is a ring in which a part of the structure is further linked to each other.
May be formed. Groups represented by X, Y, Z, and
Various substituents other than hydrogen atoms can be substituted in the atomic group
Noh. To list the examples, a halogen atom (for example,
Fluorine, chlorine, bromine, iodine), shea
Group, formyl group, or substituted or unsubstituted
A kill group (preferably having 1 to 30 carbon atoms, more preferably
The numbers are 1 to 15. For example, a methyl group, a t-butyl group,
And a clohexyl group. ), Alkenyl group
(Preferably 2-30 carbon atoms, more preferably 2-15 carbon atoms
It is. For example, vinyl group, 1-propenyl group, 1-butene
2-yl group, cyclohexen-1-yl group and the like.
You. ), Alkynyl group (preferably having 2 to 30 carbon atoms,
Preferably it has 2 to 15 carbon atoms. For example, an ethynyl group, 1-
And a propynyl group. ), Aryl groups (preferred)
Or 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms.
You. For example, phenyl, tolyl, xylyl, naph
Tyl group, biphenylyl group, pyrenyl group and the like.
You. ), A heterocyclic group (preferably a 5- or 6-membered ring)
Or may be condensed with another ring. Examples of heteroatoms include
Examples include a nitrogen atom, an oxygen atom, and a sulfur atom. Like
Or 2 to 30 carbon atoms, more preferably 2 to 15 carbon atoms.
You. For example, pyridyl group, piperidyl group, oxazolyl
Group, oxadiazolyl group, tetrahydrofuryl group, thie
And the like. ), Primary to tertiary amino groups (ami
Group, alkylamino group, arylamino group, dialkyi
Ruamino group, diarylamino group, alkylaryl group
Amino group, heterocyclic amino group, bisheterocyclic amino group
And so on. It is preferably a tertiary amino group, having 1 to 30 carbon atoms.
More preferably, it has 1 to 16 carbon atoms. For example, dimethylami
Group, diphenylamino group, phenylnaphthylamino group
And the like. ), Imino group (-CR₁₁= NR₁₂Or -N
= CR_{1 Three}R₁₄Group represented by Where R₁₁~ R₁₄Is a hydrogen atom,
Alkyl group, aryl group, heterocyclic group, alkoxy group,
A group selected from a reeloxy group and a primary to tertiary amino group.
You. Preferably 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms
It is 15. ), An alkoxy group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 15 carbon atoms. For example,
Ci, ethoxy, cyclohexyloxy, etc.
Can be ), An aryloxy group (preferably having 6 to 3 carbon atoms)
It has 0, more preferably 6 to 15 carbon atoms. For example, Feno
Xy, 1-naphthoxy, 4-phenylphenoxy
And so on. ), An alkylthio group (preferably carbon
It has 1 to 30, more preferably 1 to 15 carbon atoms. For example,
Methylthio, ethylthio, cyclohexylthio, etc.
And so on. ), An arylthio group (preferably carbon
It has 6 to 30, more preferably 6 to 15 carbon atoms. For example,
Examples include a phenylthio group and a tolylthio group. )
Rubonamide group (preferably having 1 to 30 carbon atoms, more preferably
It has 1 to 15 carbon atoms. For example, an acetamido group,
Benzoylamide group, N-methylbenzoylamide group, etc.
No. ), Sulfonamide group (preferably carbon number
It has 1 to 30, more preferably 1 to 15 carbon atoms. For example,
Tansulfonamide group, benzenesulfonamide group, p-
And a toluenesulfonamide group. ), Cal
Bamoyl group (preferably having 1 to 30 carbon atoms, more preferably
It has 1 to 15 carbon atoms. For example, unsubstituted carbamoyl
Group, methylcarbamoyl group, dimethylcarbamoyl group,
Phenylcarbamoyl group, diphenylcarbamoyl group,
And a dioctylcarbamoyl group. ), Sur
Famoyl group (preferably having 1 to 30 carbon atoms, more preferably
Has 1 to 15 carbon atoms. For example, unsubstituted sulfamoi
Group, methylsulfamoyl group, dimethylsulfamoy
Group, phenylsulfamoyl group, diphenylsulfa
Moyl group, dioctylsulfamoyl group and the like.
You. ), An alkylcarbonyl group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 15 carbon atoms. For example, Acet
Group, propionyl group, butyroyl group, lauroyl group
And so on. ), Arylcarbonyl group (preferably
Has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. An example
For example, benzoyl group, naphthoyl group, etc.
You. ), An alkylsulfonyl group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 15 carbon atoms. For example, methane
Sulfonyl group, ethanesulfonyl group and the like.
You. ), An arylsulfonyl group (preferably having 6 to 3 carbon atoms)
It has 0, more preferably 6 to 15 carbon atoms. For example, Benze
Sulfonyl group, p-toluenesulfonyl group, 1-naphthale
And a sulfonyl group. ), Alkoxycal
Bonyl group (preferably having 1 to 30 carbon atoms, more preferably
It is a prime number 1-15. For example, a methoxycarbonyl group, d
Toxoxycarbonyl group, butoxycarbonyl group, etc.
Can be ), An aryloxycarbonyl group (preferably
It has 6 to 30 carbon atoms, more preferably 6 to 15 carbon atoms. example
Phenoxycarbonyl group, 1-naphthoxycarbonyl group
And the like. ), Alkylcarbonyloxy group
(Preferably 1-30 carbon atoms, more preferably 1-15 carbon atoms
It is. For example, an acetoxy group, a propionyloxy
Group, butyroyloxy group and the like. ), Ally
Carbonyloxy group (preferably having 6 to 30 carbon atoms,
Preferably it has 6 to 15 carbon atoms. For example, benzoyloki
And a 1-naphthoyloxy group. ), C
Rethane group (preferably having 1 to 30 carbon atoms, more preferably charcoal
It is a prime number 1-15. For example, methoxycarbonamide
Group, phenoxycarbonamide group, methylaminocarbo
And amido groups. ), Ureido group (preferred
It preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms.
For example, methylaminocarbonamide group, dimethylamino
Nocarbonamide group, diphenylaminocarbonamide
And the like. ), A carbonate group (preferably
It has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms. example
For example, methoxycarbonyloxy group, phenoxycarboni
And a luoxy group. ). further,
The compound represented by the general formula (1) has the silicon-containing ring structure
Compound having a structure as a part of its repeating unit
May be formed. In this case, ethylenic in X, Y, Z
May cause polymerizable groups such as unsaturated bonds, or condensation polymerization
Such as carboxyl, amino and ester groups
Containing a compatible group and polymerizing the group
Or a compound represented by the general formula (1)
The polymer is formed while the precursor forms the compound skeleton of the general formula (1).
May be formed.

Regarding the compound represented by the general formula (1), a compound having a structure finally exhibiting a function can be used as it is, regardless of whether it is a low molecular weight or a high molecular weight. The precursor may be used in an organic light-emitting device, and after or during the construction of the device, a physical or chemical post-treatment may be used to guide the final structure. When used as a low molecular weight compound, the molecular weight is preferably in the range of 200 to 5,000, preferably 300 to 2,000. When used as a polymer compound, the average molecular weight (Mw) is preferably in the range of 2,000 to 100,000, preferably 5,000 to 100,000.

The compound represented by the general formula (1) can be synthesized by a known method. The most common method is to first introduce a structure corresponding to Z from a halogenosilane compound, and then introduce a structure represented by X or Y. The general synthesis scheme is described below, followed by specific examples of the compound of the present invention. The invention is of course not limited by these specific examples.

[0011]

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[0012]

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[0013]

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[0014]

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[0015]

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[0016]

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[0017]

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[0018]

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[0019]

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Next, a light emitting device containing the compound of the present invention will be described. The method for forming the organic layer of the light-emitting element containing the compound of the present invention is not particularly limited, and a method such as resistance heating evaporation, electron beam, sputtering, molecular lamination, coating, or an inkjet method is used. From the viewpoint of characteristics and production, resistance heating evaporation and coating are preferred.

The light-emitting device of the present invention is a device in which a light-emitting layer or a plurality of organic compound thin films including the light-emitting layer is formed between a pair of anode and cathode electrodes. , 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 anode supplies holes to the hole injection layer, the hole transport 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. It is possible to use 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 (ITO), or metals such as gold, silver, chromium, and nickel, and furthermore, these metals and conductive metal oxides. Mixtures or laminates, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO, and the like. Oxides,
In particular, ITO is 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 usually 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 manufacturing 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 dispersion of indium tin oxide are used. The film is formed by a method such as coating. The anode can be cleaned or otherwise treated to lower the device's drive voltage,
It is also possible to increase the luminous efficiency. For example, in the case of ITO, UV-ozone treatment, plasma treatment and the like are effective.

The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, and the like. The cathode has good adhesion, ionization potential, and the like between the negative electrode such as the electron injection layer, the electron transport layer, and the light emitting layer. It is selected in consideration of stability and the like. As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples thereof include an alkali metal (for example, L
i, Na, K, Cs, etc.) and their fluorides, alkaline earth metals (eg, Mg, Ca, etc.) and their fluorides, gold,
Silver, lead, alnium, sodium-potassium alloy or mixed metal thereof, lithium-aluminum alloy or mixed metal thereof, magnesium-silver alloy or mixed metal thereof, indium, rare earth metal such as ytterbium, and the like, preferably A material having a work function of 4 eV or less, more preferably aluminum, a lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof, or the like. The cathode can have not only a single-layer structure of the compound and the mixture, but also a stacked structure including the compound and the mixture. The thickness of the cathode can be appropriately selected depending on the material, but is usually 10 nm.
-5 μm is preferable, and more preferably 50 μm.
nm to 1 μm, and more preferably 100 nm to 1 μm.
m. A method such as an electron beam method, a sputtering method, a resistance heating evaporation method, or a coating method is used for manufacturing the cathode, and a metal can be evaporated alone or two or more components can be simultaneously evaporated. Further, an alloy electrode can be formed by depositing a plurality of metals at the same time, or an alloy prepared in advance may be deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

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 when applying an electric field and also injecting electrons from a cathode or an electron injection layer or an electron transport layer. 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. Preferably, the light emitting layer contains the amine compound of the present invention, but other light emitting materials can also be used. For example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives, oxadiazole derivatives, aldazine derivatives , Pyrazine derivative, cyclopentadiene derivative,
Bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidin compounds, various metal complexes represented by 8-quinolinol derivative metal complexes and rare earth complexes, Polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene are exemplified. Although the thickness of the light emitting layer is not particularly limited, it is usually 1 nm to 5 nm.
It is preferably in the range of μm, more preferably 5 nm to
It is 1 μm, and more preferably 10 nm to 500 nm. The method for 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.), LB, and ink jet. 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. Should be fine. In the present invention, the compound of the general formula (1) is used for this purpose. 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.
Examples of the method for forming the hole injection layer and the hole transport layer include a vacuum deposition method, an LB method, an inkjet method, and a method in which the hole injection and transport agent is dissolved or dispersed in a solvent and coated (spin coating method, casting method, Dip coating method) is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate, ABS resins, polyurethanes, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, and the like.

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, or 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, carbidiimide derivatives, fluorenylidene methane derivatives, distyrylpyrazine derivatives, naphthalene perylene, and phthalocyanines And various metal complexes represented by metal complexes of derivatives, 8-quinolinol derivatives, metal phthalocyanines, and 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.
m, more preferably 5 nm to 1
μm, 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. Examples of the method for forming the electron injecting layer and the electron transporting layer include a vacuum deposition method, an LB method, an ink jet method, and a method in which the electron injecting and transporting agent is dissolved or dispersed in a solvent and coated (spin coating method, casting method, dip coating method). Etc.) are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.

As the material of the protective layer, any material may be used as long as it has a function of preventing a substance that promotes element deterioration such as moisture and oxygen from entering the element. As a specific example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO ₂ , Al ₂ O ₃ , G
eO, NiO, CaO, BaO, Fe 2 O 3, Y 2 O 3, T
metal oxides such as iO ₂ , MgF ₂ , LiF, AlF ₃ , C
aF ₂ metal fluorides such as, polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, poly-dichloro-difluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, At least one with tetrafluoroethylene
A copolymer obtained by copolymerizing a monomer mixture containing a kind of comonomer, a fluorinated copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more, a water absorption of 0.1% The following moisture-proof substances are listed. There is no particular limitation on the method of forming the protective layer, for example, a vacuum evaporation method,
Sputtering method, reactive sputtering method, MBE
(Molecular beam epitaxy) method, cluster ion beam method,
An ion plating method, a plasma polymerization method (high-frequency excitation ion plating method), a plasma CVD method, a laser CVD method, a thermal CVD method, a gas source CVD method, a coating method, and an inkjet method can be applied.

[0029]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. (Example 1) ITO on a 25 mm x 25 mm x 0.7 mm glass substrate
Film formed with a thickness of 150 nm (Tokyo Sanyo Vacuum Co., Ltd.)
Was used as a transparent support substrate. After etching and washing the transparent support substrate, about 10 nm of copper phthalocyanine was deposited. next
The TPD (N, N'-bis (3-methylphenyl) -N, N'-diphenylbenzidine) of about 40 nm and the third layer of Alq (tris (8-hydroxyquinolinato) aluminum) of about 60 nm in order of 10 ^-3. Vapor deposition was performed at a substrate temperature of room temperature in a vacuum of 1010 ⁻⁴ Pa. A patterned mask (a mask with a light-emitting area of 5 mm x 5 mm) is placed on the organic thin film, and magnesium: silver = 10: 1 is co-deposited at 250 nm in a vapor deposition device, and then 300 nm of silver is vapor-deposited to produce the element 101. did. EL devices 102 to 108 having exactly the same composition as 101 except that three comparative compounds and four compounds of the present invention were used instead of TPD for device 101 were produced. Using a source measure unit 2400 manufactured by Toyo Technica, a DC constant voltage is applied to the EL element to emit light, and the brightness is measured by a luminance meter BM-8 manufactured by Topcon Corporation.The emission wavelength is measured by a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. It measured using. Table 1 shows the results.

[0030]

[Table 1]

[0031]

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Further, these elements were sealed in an autoclave replaced with argon gas, and heated under a heating condition of 85 ° C. for 1 hour.
Table 2 shows the results of the same luminance measurement and light emission surface observation after storage for 0 days.

[0033]

[Table 2]

As is clear from the results shown in Table 1, it can be seen that the devices 102 to 104 using the comparative compound can only emit light of lower luminance than the type device 101. In contrast, in the devices 105 to 108 using the hole transport material of the present invention,
Light emission of more than type was observed. Furthermore, from the results in Table 2, it can be seen that in the device using the compound of the present invention, a remarkable performance as compared with the type was obtained in terms of durability.

Example 2 40 mg of poly (N-vinylcarbazole (PVK)) and 2,5-bis (1-naphthyl) -1,3 were deposited on an ITO glass substrate etched and washed in the same manner as in Example 1. ,Four-
A solution prepared by dissolving 12 mg of oxadiazole and 10 mg of coumarin-6 in 3 ml of 1,2-dichloroethane was spin-coated. At this time, the thickness of the organic layer was about 120 nm. Next, a cathode was vapor-deposited in the same manner as in Example 1 to produce an EL element 201. Element 2
On the other hand, EL devices 202 to 205 having exactly the same composition as 201 were prepared except that two comparative compounds and two compounds of the present invention were used instead of PVK. Using a source measure unit 2400 manufactured by Toyo Technica, a DC constant voltage is applied to the EL element to emit light, and the brightness is measured by a luminance meter BM-8 manufactured by Topcon Corporation.The emission wavelength is measured by a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. It measured using. Table 3 shows the results.

[0036]

[Table 3]

[0037]

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As is evident from the results in Table 3, it can be seen that the devices 202 and 203 using the comparative compound only emitted light of lower luminance than the type device 201. In contrast, in the devices 204 and 205 using the hole transport material of the present invention,
Light emission of higher brightness than the type was observed.

By using the compound having a silicon-containing ring structure of the present invention, an organic light-emitting device having high luminance and excellent durability can be obtained.

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Claims (7)

[Claims] 1. A compound represented by the general formula (1). Embedded image At least one of X and Y is a hole-transporting group, Z is an atomic group capable of forming a 3- to 8-membered ring containing silicon, and X, Y, and Z have a part of the structure. An annular structure connected to each other may be formed. 2. A compound represented by the general formula (1):
The compound according to claim 1, wherein at least one of the groups represented by X and Y contains a primary to tertiary amine. 3. A compound represented by the general formula (1):
2. The compound according to claim 1, wherein at least one of the groups represented by X and Y contains a condensed or non-condensed π-electron-rich aromatic heterocycle. 4. An organic light-emitting device material comprising a compound represented by the general formula (1) according to claim 1 or a precursor thereof. 5. The organic light emitting device material according to claim 4, wherein at least one of X, Y and Z in the general formula (1) contains a polymerizable group and contains a polymer compound derived therefrom. 6. An organic light emitting device comprising at least one organic light emitting device material according to claim 4. 7. The organic light-emitting device according to claim 5, wherein at least one of the organic layers is formed by coating.