JP3211994B2 - Tetrafunctional styryl compound and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a tetrafunctional styryl compound and a method for producing the same, and more particularly, to a tetrafunctional styryl compound capable of emitting light with high luminance and high efficiency when used as a light emitting material of an organic electroluminescence device. The present invention relates to a compound and a method for producing the compound.

[0002]

2. Description of the Related Art EL devices utilizing electroluminescence have the characteristics of high visibility due to self-luminescence and excellent impact resistance because they are completely solid devices. , Thin display elements, backlights for liquid crystal displays, flat light sources, and the like. An EL element currently in practical use is a dispersion-type EL element. This dispersion-type EL element has several tens of volts and 10 kHz.
Since the above AC voltage is required, the driving circuit is complicated. On the other hand, organic thin film EL devices can reduce the driving voltage to about 10 V and emit light with high luminance, and have been actively studied in recent years, and many organic thin film EL devices have been developed (CWTang and SAVAN Slyke, Appl.Phys.L
ett., vol. 51, pp. 913-915 (1987); JP-A-63-264.
629). These organic thin film EL devices are of a stacked type of a transparent electrode / a hole injection layer / a light emitting layer / a back electrode, and holes can be efficiently injected into the light emitting layer by the hole injection layer. In the structure of the organic thin-film EL device, an organic EL thin-film device using a tetraphenylbutadiene compound derivative in a light-emitting layer (JP-A-59-194393, JP-A-4-96990) and a styryl compound (European Patent Publication No. 0388768, JP-A-4-18489
No. 2, JP-A-3-205478), however, these materials have a problem that they are easily crystallized, and uniform light emission cannot be obtained. Further, in recent years, an organic EL device containing a trifunctional compound derived from the styryl compound as a light emitting material has been disclosed (Japanese Unexamined Patent Application Publication No. Hei.
296595) has a problem that the luminance and the luminous efficiency are low.

[0003]

Means for Solving the Problems Accordingly, the present inventors have:
As a result of intensive studies to solve the above problems, it has been found that the above problems can be solved by using a tetrafunctional compound obtained by improving a trifunctional compound as a light emitting material of an organic EL device.

The present invention has been completed based on such findings. That is, the present invention provides a compound represented by the general formula (I):

[0005]

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(Wherein, Ar represents a tetravalent aromatic hydrocarbon group having 6 to 20 carbon atoms, and R ² , R ³ , R ⁶ , and R ⁷ each represent a hydrogen atom, a substituted or unsubstituted C 6 Represents an aryl group having from 20 to 20 or an alkyl group having from 1 to 6 carbon atoms.
R ¹ , R ⁹ , R ⁴ , R ¹⁰ , R ⁵ , R ¹¹ , R ⁸ , and R ¹² each represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, Number 4-1
8 represents a heterocyclic group. Here, even if R ^{1 to} R ¹² are the same,
They may be different from each other. Further, R ¹ and R ⁹ , R ⁴
And R ¹⁰ , R ⁵ and R ¹¹ , and R ⁸ and R ¹² are each bonded to a substituted group to form a substituted or unsubstituted saturated 5-membered ring or a substituted or unsubstituted saturated 6-membered ring. Is also good. However, R ¹ and R ^9, R ⁴ and R ^10, R ⁵ and R ^11, R ⁸
Excludes cases where R and R ¹² are both alkyl groups. Here, the substituent is an alkyl group having 1 to 6 carbon atoms, 1 to 6 carbon atoms.
An alkoxy group, an aryloxy group having 6 to 18 carbon atoms,
It represents a phenyl group, amino group, cyano group, nitro group, hydroxyl group or halogen. These substituents may be single or plurally substituted. The present invention provides a tetrafunctional styryl compound represented by the general formula (II):

[0007]

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(Wherein R ² , R ³ , R ⁶ , and R ⁷ are the same as above. R ¹³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, which may be the same or different. .) And a general formula (III)

[0009]

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(Wherein R ¹ , R ⁹ , R ⁴ , R ¹⁰ , R ⁵ ,
R ¹¹ , R ⁸ and R ¹² are the same as described above. The present invention provides a method for producing the above tetrafunctional styryl compound by reacting a ketone represented by the formula (1).

The present invention is a tetrafunctional styryl compound represented by the general formula (I). Here, in the general formula (I), Ar is

[0012]

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A tetravalent aromatic hydrocarbon such as phenanthrene; perylene; 1,2-benzanthracene; naphthacene; chrysene; and quarterphenylene, which may be monosubstituted or plurally substituted. Further, the substituents may be bonded to each other to form a saturated or unsaturated 5- or 6-membered ring. R ² , R ³ , R ⁶ and R ⁷ are, for example, phenyl, naphthyl, biphenyl, terphenyl,
An aryl group having 6 to 20 carbon atoms represented by an anthralyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, or a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group , Sec-butyl group, t-butyl group, i-pentyl group, t-pentyl group,
An alkyl group having 1 to 6 carbon atoms represented by a neopentyl group, an n-hexyl group, an i-hexyl group or the like, or hydrogen. Among them, those in which the substituent is hydrogen, methyl, or phenyl are preferred because of easy production. Further, these aryl groups or alkyl groups may be substituted or unsubstituted,
It may be single substituted or plural substituted. R ¹ , R ⁹ ,
R ⁴ , R ¹⁰ , R ⁵ , R ¹¹ , R ⁸ , and R ¹² are, for example, methyl, ethyl, n-propyl, i-propyl, n-
1 to 1 carbon atoms such as butyl group, i-butyl group, sec-butyl group, t-butyl group, i-pentyl group, t-pentyl group, neopentyl group, n-hexyl group and i-hexyl group.
6 carbon atoms represented by an alkyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, anthralyl group, phenanthryl group, pyrenyl group, perylenyl group, etc.
And a heterocyclic group having 4 to 18 carbon atoms represented by an aryl group of 20 to 20 or a pyrazyl group, a pyridyl group, a quinolyl group, a carbazolyl group, a quinoxalyl group, or the like. These alkyl groups, aryl groups or heterocyclic groups may be substituted or unsubstituted, and may be single-substituted or multiple-substituted. However, R ¹ and R ^9, R ⁴ and R ^10, R ⁵ and R ^11, R ⁸ and R ¹²
Are not alkyl groups (for example, a combination of acetone or methyl ethyl ketone in the general formula (III)). Further, R ¹ and R ⁹ , R ⁴ and R ¹⁰ , R ⁵
And R ¹¹ , or R ⁸ and R ¹² may be bonded to a substituted group to form a substituted or unsubstituted saturated 5-membered ring or a substituted or unsubstituted saturated 6-membered ring. As a specific example of such a ring structure, 9-fluorenone is mentioned as a ketone compound represented by the general formula (III). Here, examples of the substituent include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, an i-pentyl group, and a t-group. An alkyl group having 1 to 6 carbon atoms such as -pentyl group, neopentyl group, n-hexyl group, i-hexyl group,
Methoxy, ethoxy, propoxy, i-propoxy, butyloxy, i-butyloxy, sec-
C1-C6 alkoxy groups such as butyloxy group, i-pentyloxy group, t-pentyloxy group, n-hexyloxy group, C6-C18 aryloxy groups such as phenoxy group and naphthyloxy group, phenyl group , An amino group, a cyano group, a nitro group, a hydroxyl group or a halogen. Specifically, as the amino group,

[0014]

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(In the formula, R ¹⁴ and R ¹⁵ represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted. R ¹⁴ and R ¹⁵ may be the same or different. Or a compound represented by the formula:

The tetrafunctional styryl compound represented by the general formula (I) is obtained by reacting a tetrakis arylene phosphonate represented by the general formula (II) with a ketone represented by the general formula (III). Can be synthesized by This reaction is usually performed in a polar solvent in the presence of a base in a temperature range from 0 ° C. to the boiling point of the solvent used (Wi
ttig-Horner reaction). Where the general formula (II)
R ¹³ represents an alkyl group having 1 to 4 carbon atoms and a phenyl group, and is preferably a methyl group or an ethyl group. The tetrakis arylene phosphonate represented by the general formula (II) is represented by the general formula (IV)

[0017]

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Wherein R ² , R ³ , R ⁶ , R ⁷ and A
r is the same as above. X represents a halogen, and may be the same or different. )) And a trialkyl phosphite compound. As the reaction solvent used in the synthesis of the tetrafunctional styryl compound, a polar solvent such as a hydrocarbon, an alcohol, or an ether is preferable. Specifically, methanol; ethanol; isopropanol; butanol; 2-methoxyethanol; 1,2-dimethoxyethane; bis (2-methoxyethyl) ether; dioxane; tetrahydrofuran; toluene; xylene; dimethyl sulfoxide; N, N-dimethyl Formamide; N
-Methylpyrrolidone; 1,3-dimethyl-2-imidazolidinone; Particularly, tetrahydrofuran and dimethyl sulfoxide are preferred. Further, as the base, an alcoholate such as caustic soda, caustic potash, sodium amide, sodium hydride, n-butyllithium, sodium methylate, and potassium tert-butoxide is preferable, and n-butyllithium and potassium tert-butoxide are particularly preferable.

The tetrafunctional styryl compounds (1) to (36) used in the present invention (hereinafter, compounds (1) to (36))
(36). ), But the present invention is not limited thereto.

[0020]

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[0021]

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[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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Such a tetrafunctional styryl compound can be obtained by using EL
It can be effectively used as a light emitting material in a device. When this tetrafunctional styryl compound is used as a light emitting layer,
For example, it can be formed by making the tetrafunctional styryl compound of the general formula (I) into a thin film by a known method such as a vapor deposition method, a spin coating method, and a casting method, but it is particularly preferable to use a molecular deposition film. Here, the molecular deposition film is a thin film formed by depositing the compound from a gaseous state or a film formed by solidifying the compound from a solution state or a liquid phase state. Shows,
Usually, this molecular deposition film can be distinguished from a thin film (molecule accumulation film) formed by the LB method. Further, as disclosed in JP-A-59-194393, the binder is prepared by dissolving a binder such as a resin and the compound in a solvent to form a solution. It can be formed into a thin film by the method described above. The thickness of the light emitting layer formed in this manner is not particularly limited and can be appropriately selected according to the situation, but is usually selected in the range of 5 nm to 5 μm.

The light emitting layer of this EL device has the following features. (1) When an electric field is applied, holes can be injected by an anode or a hole injection transport layer, and electrons can be injected by a cathode or an electron injection layer. Function, (2) transport function of moving injected charges (electrons and holes) by the force of an electric field, and (3) light emission that provides a field of recombination of electrons and holes inside the light emitting layer, which is connected to light emission. It has functions and the like. Note that there may be a difference between the ease with which holes are injected and the ease with which electrons are injected, and the transportability represented by the mobility of holes and electrons may be large or small. Is preferably transferred. The compound represented by the general formula (I) used for the light emitting layer generally has an ionization energy of 6.0 e.
Since it is smaller than about V, it is relatively easy to inject holes if an appropriate anode metal or anode compound is selected. Further, since the electron affinity is higher than about 2.8 eV, if an appropriate cathode metal or cathode compound is selected, it is relatively easy to inject electrons, and also excellent in the ability to transport electrons and holes. Further, since the solid-state fluorescence is strong, the ability to convert an excited state formed at the time of recrystallization of electrons and holes of the compound or its aggregate or crystal, to light is large.

The EL device using the compound of the present invention has various configurations, but basically has a configuration in which the light emitting layer is sandwiched between a pair of electrodes (anode and cathode). If necessary, a hole injection / transport layer or an electron injection layer may be interposed. As an intervening method, there is mixing into a polymer or simultaneous adsorption. Specifically, (1) anode / light-emitting layer / cathode, (2) anode / hole injection / transport layer / light-emitting layer / cathode,
Examples of (3) anode / hole injection / transport layer / light-emitting layer / electron injection layer / cathode, and (4) anode / light-emitting layer / electron injection layer / cathode, etc. The hole injecting and transporting layer and the electron injecting layer are not necessarily required, but the presence of these layers further improves the light emitting performance. In addition, in the device having the above-described structure, it is preferable that each of the devices is supported by a substrate, and the substrate is not particularly limited, and is made of a material conventionally used in an EL device, such as glass, transparent plastic, or quartz. Can be used.

As the anode in this EL element, a metal, an alloy, an electrically conductive compound having a high work function (4 eV or more) and a mixture thereof are preferably used as an electrode material. A specific example of such an electrode material is A
u and a dielectric transparent material such as CuI, ITO, SnO ₂ , and ZnO. The anode can be produced by forming a thin film from these electrode substances by a method such as vapor deposition or sputtering. When light is extracted from this electrode, the transmittance is desirably higher than 10%, and the sheet resistance of the electrode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually 10 nm to 1 μm, preferably 10 to 1 μm.
It is selected in the range of 200 nm.

On the other hand, as the cathode, a metal, an alloy, an electrically conductive compound having a small work function (4 eV or less), and a mixture thereof as an electrode material are used. Specific examples of such an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, a magnesium / copper mixture, Al / AlO ₂ , and indium. The cathode can be manufactured by forming a thin film of these electrode substances by a method such as vapor deposition or sputtering. Further, the sheet resistance as an electrode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm.
To 1 μm, preferably in the range of 50 to 200 nm. In this EL device, it is convenient that one of the anode and the cathode is transparent or translucent because it transmits light, so that the efficiency of extracting light is good.

As described above, the structure of the EL device using the compound of the present invention has various modes, and the hole injecting / transporting layer in the EL device having the structure (2) or (3) is
A layer made of a hole transporting compound, which has a function of transmitting holes injected from the anode to the light emitting layer, and has a hole injecting and transporting layer interposed between the anode and the light emitting layer. Many holes are injected into the light emitting layer at a low electric field. In addition, electrons injected from the cathode or the electron injection layer into the light emitting layer are accumulated near the interface in the light emitting layer due to the electron barrier existing at the interface between the light emitting layer and the hole injection transport layer, and the light emission of the EL element is reduced. Efficiency is improved and an EL element having excellent light emitting performance is obtained.

The hole transporting compound used in the hole injecting / transporting layer is disposed between two electrodes to which an electric field is applied. When holes are injected from the anode, the holes are appropriately transferred to the light emitting layer. A compound capable of transmitting to, for example, 10 ⁴ to 10 ⁶ V
/ Cm when applying an electric field of at least 10 ^-6 cm ² / (V
(Seconds) is preferable. There is no particular limitation on such a hole transporting compound as long as it has the above-mentioned preferable properties. Conventionally, in a photoconductive material, a compound commonly used as a hole charge transport material or a hole transporting material of an EL device is used. Any of the known materials used for the injection transport layer can be selected and used.

As the charge transport material, for example, a triazole derivative (as described in US Pat. No. 3,112,197) and an oxadiazole derivative (US Pat.
89,447), imidazole derivatives (described in JP-B-37-16096, etc.), polyarylalkane derivatives (US Pat. No. 3,611)
5,402, 3,820,989, 3,5
No. 42,544, Japanese Patent Publication No. 45-555, 5
1-110983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, and JP-A-55-15695.
Nos. 3 and 56-36656), pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. Nos. 3,180,729 and 4,278,746; No. 88064, 55-8806
No. 5, No. 49-105537, No. 55-51
Nos. 086 and 56-80051 and 56-8
Nos. 8141 and 57-45545 and 54-
And phenylenediamine derivatives (U.S. Pat. No. 3,615,404, JP-B-51-10105, JP-B-46-3712, and JP-A-47-47). JP-A-25-25336, JP-A-54-53435, JP-A-54-1105
Nos. 36 and 54-119925) and arylamine derivatives (U.S. Pat. No. 3,567,4).
50, 3,180,703, 3,24
Nos. 0,597, 3,658,520 and 4,2
No. 32,103, No. 4,175,961, No. 4,012,376, JP-B-49-35702, JP-A-39-27577, and JP-A-55-1442.
Nos. 50, 56-119132 and 56-2
No. 2437, West German Patent No. 1,110,518, etc.), amino-substituted chalcone derivatives (U.S. Pat. No. 3,526,501) and oxazole derivatives (U.S. Pat. No. 3,526,501). No. 3,257,203), styrylanthracene derivatives (described in JP-A-56-46234, etc.), and fluorenone derivatives (described in JP-A-54-110837). ), Hydrazone derivatives (US Pat. No. 3,71
No. 7,462, JP-A-54-59143, JP-A-55-52063, JP-A-55-52064,
JP-A-55-46760, JP-A-55-85495, JP-A-57-1350, and JP-A-57-148749.
And stilbell derivatives (JP-A-61-210363, JP-A-61-2284).
No. 51, No. 61-14642, No. 61-72
Nos. 255, 62-47646, 62-3
Nos. 6,674, 62-10652, 62-
Nos. 30255, 60-93445, 60
-94462, JP-A-60-174747, JP-A-60-175052) and the like.

The above compounds can be used as hole transporting compounds. The following porphyrin compounds (described in JP-A-63-295695) and aromatic tertiary amine compounds and styrylamine compounds ( U.S. Pat. No. 4,127,412, JP-A-53-2703
Nos. 3, 54-58445 and 54-149.
Nos. 634 and 54-64299 and 55-7
Nos. 9450, 55-144250, 56
-119132, 61-295558,
It is preferable to use the aromatic tertiary amine compound as the hole transporting compound, particularly those described in JP-A-61-98353 and JP-A-63-295695.

Representative examples of the porphyrin compound include:
Porphyrin; 5,10,15,20-tetraphenyl-21H, 23H-porphyrin copper (II);
15,20-tetraphenyl-21H, 23H-porphyrin zinc (II); 5,10,15,20-tetrakis (pentafluorophenyl) -21H, 23H-porphyrin; silicon phthalocyanine oxide; aluminum phthalocyanine chloride; phthalocyanine (metal-free Dilithium phthalocyanine; copper tetramethyl phthalocyanine; copper phthalocyanine; chromium phthalocyanine; zinc phthalocyanine; lead phthalocyanine; titanium phthalocyanine oxide; magnesium phthalocyanine;
Representative examples of the aromatic tertiary compound and styrylamine compound include N, N, N ′, N′-tetraphenyl- (1,1′-biphenyl) -4,4′-diamine;
N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine; 2,2-bis (4-di-p-tolylamino Phenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl- (1,1′-biphenyl) -4,
4'-diamine; 1,1-bis (4-di-p-tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p- Tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N'-di (4-methoxyphenyl)-(1,1'-biphenyl)
-4,4'-diamine; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether;
4'-bis (diphenylamino) quadriphenyl;
N, N, N-tri (p-tolyl) amine; 4- (di-p
-Tolylamine) -4 '-[4 (di-p-tolylamine) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylamino Stilbene; N-
Phenylcarbazole and the like.

The hole injecting and transporting layer in the EL device may be composed of one or more of these hole transporting compounds, or may be a hole transporting compound of a different kind from the layer. It may be a laminate of injection and transport layers. On the other hand, the electron injecting layer (electron injecting and transporting layer) in the EL device having the constitution (3) is made of an electron transfer compound, and has a function of transferring electrons injected from the cathode to the light emitting layer. I have. There is no particular limitation on such an electron transfer compound, and any one of conventionally known compounds can be selected and used. Preferred examples of the electron transfer compound include:

[0043]

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Nitro-substituted fluorenone derivatives such as

[0045]

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Thiopyran dioxide derivatives such as

[0047]

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Diphenylquinone derivatives (those described in Polymer Preprints, Japan, Vol. 37, No. 3, page 681 (1988), etc.), or

[0049]

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[Journal of Applied Physics], vol. 27,
269 (1988)] and anthraquinodimethane derivatives (JP-A-57-149259, JP-A-58-55450, and 61-22515).
No. 1, No. 61-233750, No. 63-10
4061), fluorenylidenemethane derivatives (JP-A-60-69657 and JP-A-60-69657).
143,768, 61-148159, etc.), anthrone derivatives (JP-A-61-2).
Nos. 25151 and 61-233750), and the following general formula (A) or (B)

[0051]

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(Wherein, Ar ^{1 to} Ar ³ and Ar ⁵ each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and Ar ⁴ represents a substituted or unsubstituted arylene having 6 to 20 carbon atoms. Which represents a group). Here, the aryl group includes a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, a pyrenyl group, and the like. And the like. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group. The compound represented by formula (A) or (B) is preferably a compound capable of forming a thin film. Specific examples of the compound represented by the general formula (A) or (B) include:

[0053]

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[0054]

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[0055]

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And the like.

"Appl. Phys. Lett." Vol. 55, No. 148
Oxadiazole derivatives disclosed on page 9 (1989) can be mentioned. The hole injecting / transporting layer and the electron injecting layer are layers having any one of an injecting property, a transporting property, and a barrier property of electrification. In addition to the above-described organic materials, crystalline materials such as Si-based, SiC-based, and CdS-based Alternatively, an inorganic material such as an amorphous material can be used. The hole injection transport layer and the electron injection layer using an organic material can be formed in the same manner as the light emitting layer, and the hole injection transport layer and the electron injection layer using an inorganic material are formed by a vacuum evaporation method, sputtering, or the like. Although it is possible to use any of organic and inorganic materials, it is preferable to form by a vacuum deposition method for the same reason as in the light emitting layer.

Next, an example of a preferred method for producing an EL device using the compound of the present invention will be described for each device of each constitution. EL comprising the above anode / light-emitting layer / cathode
First, a thin film made of a desired electrode material, for example, a material for an anode is deposited or sputtered on a suitable substrate so as to have a thickness of 1 μm or less, preferably 10 to 200 nm. After forming an anode, a thin film of a tetrafunctional styryl compound represented by the general formula (I), which is a light emitting material, is formed thereon, and a light emitting layer is provided. Examples of the method for thinning the luminescent material include spin coating, casting, and the like.
Although there is a vapor deposition method and the like, a vapor deposition method is preferable because a uniform film is easily obtained and a pinhole is hardly generated. When this vapor deposition method is used for thinning the light emitting material, the vapor deposition conditions vary depending on the type of the organic compound used for the light emitting layer to be used, the target crystal structure of the molecular deposition film, the association structure, and the like. Boat heating temperature 50-40
0 ° C., degree of vacuum 10 ⁻⁵ to 10 ⁻³ Pa, deposition rate 0.01 to 5
0 nm / sec, substrate temperature -50 to + 300 ° C, film thickness 5
It is desirable to select an appropriate value in the range of nm to 5 μm. Next, after forming this light emitting layer, a thin film made of a material for a cathode is formed thereon by a method such as vapor deposition or sputtering so as to have a thickness of 1 μm or less, preferably 50 to 200 nm. Is provided, a desired EL element is obtained. In the production of this EL element, the production order can be reversed, and the cathode, the light emitting layer, and the anode can be produced in this order.

A hole injection / transport material is provided between a pair of electrodes.
In the case of a device comprising an anode / light-emitting layer / cathode in which a light-emitting material and an electron-injecting material are mixed and sandwiched between electrodes to form a light-emitting layer, for example, a material for the anode may be provided on a suitable substrate. A thin film composed of a hole injecting and transporting material, a light emitting material, an electron injecting material, a binder such as polyvinyl carbazole or the like, or forming a thin film from this solution by a dip coating method to form a light emitting layer. And a thin film made of a cathode material is formed thereon. Here, an element material to be a material of the light emitting layer may be further vacuum-deposited on the manufactured light emitting layer, and a thin film made of a cathode material may be formed thereon. Alternatively, a hole injecting and transporting material, an electron injecting material, and a light emitting material are simultaneously deposited to form a light emitting layer,
A thin film made of a cathode material may be formed thereon.

Next, a method for manufacturing an EL device comprising an anode / a hole injection / transport layer / a light emitting layer / a cathode will be described. First, an anode is formed in the same manner as in the case of the above EL device, and then the anode is formed thereon. Then, a thin film made of a hole transport compound is formed by a spin coating method or the like, and a hole injection / transport layer is provided.
The conditions at this time may be in accordance with the conditions for forming the thin film of the light emitting material. Next, a desired EL element can be obtained by sequentially providing a light emitting layer and a cathode on the hole injecting and transporting layer in the same manner as in the case of manufacturing the EL element. In addition,
Also in the production of this EL element, the production order is reversed,
It is also possible to produce a cathode, a light emitting layer, a hole injection / transport layer, and an anode in this order. Further, a method of manufacturing an EL device composed of an anode / a hole injection / transport layer / a light emitting layer / an electron injection layer / a cathode will be described. First, as in the case of the EL device, the anode, the hole injection / transport layer are formed. After sequentially providing a layer and a light emitting layer, a thin film made of an electron transfer compound is formed on the light emitting layer by a spin coating method or the like, an electron injection layer is provided, and then a cathode is formed on the EL element. By providing the EL device in the same manner as in the case of manufacturing, a desired EL element can be obtained. In the production of this EL element, the production order may be reversed, and the anode, the electron injection layer, the light emitting layer, the hole injection transport layer, and the anode may be produced in this order.

When a DC voltage is applied to the EL device obtained in this manner, a voltage of about 1 to 30 V is applied with the positive polarity of the anode and the negative polarity of the cathode. Observable from the side. Also, even if a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, the anode is + and the cathode is-.
It emits light only when the state is reached. The waveform of the applied alternating current may be arbitrary.

[0062]

Next, the present invention will be described in more detail with reference to Examples, Application Examples and Application Comparative Examples. Example 1

[0063]

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1,2,4,5-tetrakis (bromomethyl
Le) benzene 25.0 g (0.056 mol, Aldrich)
Made) and 44.7 g (0.269 mol) of triethyl phosphite
The reaction was performed at an internal temperature of 130 ° C. After the reaction, n-hexane
After washing with 50 ml and leaving overnight, a white precipitate
occured. The obtained white precipitate had a yield of 36.5 g (yield 94).
%), Melting point: 49-52.5 ° C. Also, proton nuclei
Magnetic resonance (¹H-NMR, standard: tetramethylsilane
(TMS), solvent: CDCl_Three) As a result of the measurement, δ = 7.1 ppm (s, 2H, H of the central aromatic ring) δ = 4.0 ppm (q, 16H, —CH of the ethoxy group)_Two−
H) δ = 3.35 ppm (d, 8H,³¹P-CH_TwoCouplin
H, J = 20 Hz) δ = 1.20 ppm (t, 24H, —CH of ethoxy group)_Three
H). Next, 2.0 g of this phosphonate ester (0.0
03 mol), 2.8 g (0.015 mol) of benzophenone and
And potassium-t-butoxide 2.1 g (0.013 mol)
To 30 ml of dimethyl sulfoxide (DMSO)
The suspension was reacted at room temperature (18 to 19 ° C.). Obtained
The reaction was left overnight and 50 ml of methanol was added.
The precipitated yellow powder was filtered and the filter cake obtained was filtered.
The product was purified using a Ricagel column. The resulting yellow powder
The powder had a yield of 0.9 g (38% yield) and a melting point of 231.5 to 23.
2.5 ° C. Also,¹H-NMR (reference: tetrame
Tylsilane (TMS), solvent: CDCl _Three) Measurement result
As a result, δ = 7.1 ppm (s, 40H, H of terminal phenyl) δ = 6.6 ppm (s, 2H, H of central phenylene) δ = 6.7 ppm (s, 4H, H of olefin). As a result of mass spectrometry (FD-MS), M⁺(M /
Z = 790), M²⁺(M / Z = 395) only
(See FIG. 1). Furthermore, the result of elemental analysis (() is calculated
Value), C₆₄H₄₆C: 94.03% (94.14%) H: 5.97% (5.86%) From the above, the target tetrafunctional styryl compound
It was confirmed that (8) was synthesized.

Embodiment 2

[0066]

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3,3 ', 5,5'-tetrakis (bromo
10.5 g (0.020 mol) of methyl) biphenyl and phosphorus
Triethyl acid (17.28 g, 0.10 mol) at an internal temperature of 110 ° C
Was reacted. After completion of the reaction, 50 milliliters of n-hexane was used.
15.5 g (quantitative) of a clear viscous liquid when washed with torr
Obtained. Also,¹H-NMR (reference: tetramethylsi
Run (TMS), solvent: CDCl _Three) As a result of the measurement, δ = 7.3 ppm (s, 4H, of the central biphenylene ring)
H) δ = 7.1 ppm (s, 2H, of the central biphenylene ring
H) δ = 4.0 ppm (q, 16H, —CH of ethoxy group)_Two−
H) δ = 3.1 ppm (d, 8H,³¹P-CH_TwoCoupling
H, J = 20 Hz) δ = 1.2 ppm (t, 24H, —CH of ethoxy group)_Threeof
H). Next, 2.5 g of this phosphonate ester (0.0
033 mol), 3.13 g of benzophenone (0.017 mol)
1.7 g of potassium tert-butoxide (0.015
Mol) were suspended in 35 ml of DMSO and allowed to stand at room temperature (1
(8-19 ° C). Release the resulting reaction overnight
After the addition, 50 ml of methanol was added and precipitated.
The filter cake obtained by filtering the yellow powder is applied to a silica gel column.
And purified. The resulting white powder has a yield of 0.81.
g (yield 28%), melting point 223-225 ° C. Ma
Was¹H-NMR (reference: tetramethylsilane (TM
S), solvent: CDCl _Three) As a result of measurement, δ = 7.2 ppm (s, 40H, H of terminal phenyl) δ = 6.5 to 7.2 ppm (m, 10H, central biphenylene)
And vinyl H). As a result of mass spectrometry (FD-MS), M⁺(M /
Z = 866), M²⁺(M / Z = 433) only detected
(See FIG. 2). Furthermore, the result of elemental analysis (() is calculated
Value), C₆₈H₅₀C: 94.07% (94.19%) H: 5.93% (5.81%) From the above, the desired tetrafunctional styryl compound (2
0) was confirmed to be synthesized.

Embodiment 3

[0069]

Embedded image

The above compound as a by-product of the reaction of Example 2
1.06 g of A was obtained. This compound A is white powder
And the melting point was 177 to 178 ° C. Also,¹H-N
MR (reference: tetramethylsilane (TMS), solvent: C
DCI _Three) As a result of the measurement, δ = 7.2 ppm (s, 30H, H of the terminal phenyl group) δ = 6.6 to 6.9 ppm (m, 9H, biphenylene at the center)
H of ring and vinyl) δ = 3.9 ppm (q, 2H, -CH of ethoxy group)_Two-
H) δ = 2.8 ppm (d, 2H,³¹P-CH_TwoCoupling
H, J = 20 Hz) δ = 1.2 ppm (t, 3H, —CH of ethoxy group)_Threeof
H). Also, as a result of mass spectrometry (FD-MS), M⁺
(M / Z = 838) indicates that Compound A was synthesized.
Was confirmed. Next is this phosphonate
Compound A 1.0 g (0.0012 mol), 4,4'-dimethoate
0.38 g (0.0016 mol) of xybenzophenone and
0.22 g (0.002 mol) of potassium tert-butoxide
Suspended in 30 ml of DMSO, room temperature (18-20
C). After leaving the obtained reaction product overnight,
White powder precipitated by adding 50 ml of tanol
Is filtered through a silica gel column.
Was. The resulting white plate crystals had a yield of 0.23 g (yield
21%), melting point 138-147 ° C. Also,¹
H-NMR (reference: tetramethylsilane (TMS), dissolved
Medium: CDCl _Three) As a result of the measurement, δ = 7.2 ppm (s, 38H, H of the terminal phenyl group) δ = 6.4 to 7.2 ppm (m, 10H, central biphenylene)
And H of vinyl) δ = 3.6 ppm (d, 6H, H of methoxy group). As a result of mass spectrometry (FD-MS), M⁺(M /
Z = 926), M²⁺(M / Z = 463) only detected
(See FIG. 3). From the above, the desired tetrafunctional styryl compound
It was confirmed that the product (23) was synthesized.

Embodiment 4

[0072]

Embedded image

3,3 ', 5,5'-tetrakis [(die
Tyl phosphoryl) methyl] biphenyl 1.5 g (0.002
0 mol), 3.6 g of 4-diphenylaminobenzophenone
(0.0104 mol) and potassium tert-butoxide 1.
0 g (0.009 mol) in 35 mL of DMSO
It became cloudy and reacted at room temperature (20-25 ° C) for 5 hours. Get
After standing the reaction product overnight, 80% methanol water 40
Milliliter was added and the precipitated pale yellow powder was filtered
Was. The obtained filter cake is applied to a silica gel column (developing solvent: acetic acid).
Mixture of ethyl ester (2 parts by weight) and n-hexane
(1 part by weight). The resulting pale yellow powder
Has a yield of 1.3 g (43% yield) and a melting point of 150 to 170 ° C.
Met. Also,¹H-NMR (reference: tetramethylsi
Run (TMS), solvent: CDCl _Three) As a result of the measurement, δ = 7.32 to 6.93 ppm (m, 82H, terminal phenyl)
H of the group and the central biphenylene ring) δ = 6.75 to 6.67 pm (d, 4H, H of the vinyl group). As a result of mass spectrometry (FD-MS), M⁺(M /
Z = 1534), M²⁺(M / Z = 767) only detected
(See FIG. 4). Furthermore, the results of elemental analysis (()
Arithmetic), C₁₁₆H₈₆H_FourC: 90.76% (90.71%) H: 5.58% (5.64%) N: 3.66% (3.65%) From the above, the desired tetrafunctional styryl compound (2
It was confirmed that 2) was synthesized.

Application Example 1 A transparent support substrate was prepared by providing a 100 mm thick ITO film (corresponding to an anode) on a 25 mm × 75 mm × 1.1 mm glass substrate by vapor deposition. This transparent support substrate is subjected to ultrasonic cleaning with isopropyl alcohol for 5 minutes, and further washed in pure water for 5 minutes.
After ultrasonic cleaning for 20 minutes, the substrate was cleaned at a substrate temperature of 150 ° C. for 20 minutes using a UV ion cleaner (manufactured by Samco International). The transparent support substrate is dried with a dry nitrogen gas, fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Nippon Vacuum Technology Co., Ltd.), and mounted on a molybdenum resistance heating boat with phthalocyanine (CuPc) coordinated with Cu. .) To 200
mg, and N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (hereinafter referred to as resistance heating of another molybdenum boat) , TPD) in a molybdenum resistance heating boat and 1,2,4,5-tetrakis (2,2-diphenyl) represented by the compound (8) obtained in Example 1. Vinyl) benzene (hereinafter referred to as (D
PV) abbreviated as ₄ B. ) Was added. Next, after the vacuum layer was decompressed to 4 × 10 ⁻⁴ Pa, the heating boat containing CuPc was energized and heated to 350 ° C., and deposited on the transparent support substrate at a deposition rate of 0.1 to 0.3 nm / sec. A CuPc layer having a thickness of 20 nm was formed by vapor deposition. At this time, the substrate temperature was room temperature. Then, the heating boat containing the TPD is energized and heated to 215 ° C., and the evaporation rate is set to 0.1 to 0.3.
TPD was vapor-deposited on the CuPc layer at nm / sec to form a TPD layer having a thickness of 40 nm. The substrate temperature at this time was also room temperature. The CuPc layer thus provided and the TPD
Two of the layers correspond to the hole injection transport layer. Then, (D
PV) ₄ by supplying an electric current to the heating boat containing B 250 ° C.
To the above TPD at a deposition rate of 0.1 to 0.3 nm / sec.
A light emitting layer having a thickness of 40 nm was provided by vapor deposition on the layer. Next, the transparent support substrate on which the three organic layers were laminated was taken out of the vacuum chamber, and a stainless steel mask was placed on the light-emitting chamber, and was fixed to the substrate holder again. Then, the molybdenum resistance heating boat tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq _3.) Was deposited in the vacuum chamber put 200 mg. Further, a molybdenum resistance heating boat containing 1 g of magnesium ribbon and a tungsten basket containing 500 mg of silver wire were attached to a vacuum chamber. After that, the vacuum tank is 1 × 1
The pressure was reduced to 0 ^-4 Pa. After reducing the pressure, the boat containing Alq ₃ was heated to 270 ° C., and Alq ₃ was deposited on the light emitting layer at a deposition rate of 0.1 to 0.3 nm / sec to form an Alq ₃ having a thickness of 40 nm.
_Three layers (corresponding to an electron injection layer) were provided. Subsequently, silver is deposited at a deposition rate of 0.1 nm / sec by energizing a basket containing silver wires, and at the same time, magnesium is deposited at a deposition rate of 1.4 to 2.0 nm / sec by energizing a boat containing a magnesium ribbon. did. By this dual simultaneous evaporation, a 20 nm-thick magnesium-silver layer (corresponding to a cathode) was formed on the Alq ₃ layer. When a direct current of 10 V was applied using the ITO electrode of the device as an anode and the magnesium-silver layer as a cathode, a current having a current density of 77 mA / cm ² flowed, and light emission of Blue Green having a peak wavelength of 494 nm was obtained. The luminance at this time is 250 cd / m ² ,
The luminous efficiency was 0.60 lumen / W. The resulting luminescence was determined to emission from (DPV) and solid state fluorescence of ₄ B since it substantially matches (DPV) ₄ B.

Application Example 2 On a glass substrate of 25 mm × 75 mm × 1.1 mm by an evaporation method
100 nm thick ITO film (corresponding to anode)
Was used as a transparent support substrate. This transparent support substrate is
Ultrasonic cleaning with alcohol for 5 minutes, and further in pure water for 5 minutes.
After ultrasonic cleaning for 5 minutes, UV ion cleaner (Samcoin
Substrate) at substrate temperature of 150 ° C for 20 minutes
Washed. Dry this transparent support substrate with dry nitrogen gas
Substrate holder for commercially available vapor deposition equipment (manufactured by Japan Vacuum Engineering Co., Ltd.)
To the molybdenum resistance heating boat and CuPc
200 mg, and the resistance of another molybdenum boat
Add 200mg of TPD to the heating and add another molybdenum
The compound obtained in Example 2 (2
0), 3,3 ', 5,5'-tetrakis (2,
2-diphenylvinyl) biphenyl (hereinafter, (DPV)
_FourAbbreviated as Bi. ) Was added. Then vacuum layer
Is 4 × 10^-FourAfter reducing the pressure to Pa, before CuPc
The heating boat was energized and heated to 350 ° C, and the evaporation rate
0.1 to 0.3 nm / sec.
A 0 nm CuPc layer was provided. The substrate temperature at this time is
It was warm. And to the heated boat with TPD
Energize and heat to 215 ° C, evaporation rate 0.1-0.3nm
TPD is deposited on the CuPc layer at a rate of
nm TPD layer was provided. The substrate temperature at this time is also room temperature
there were. The CuPc layer and the TPD layer
The two layers correspond to a hole injection transport layer. Then, (DP
V)_Four296 ° C by supplying electricity to the heating boat containing Bi
To the above TPD at a deposition rate of 0.1 to 0.3 nm / sec.
A light emitting layer having a thickness of 40 nm was provided by vapor deposition on the layer. Next
Then, the transparent support substrate on which the three organic material layers are laminated is vacuumed.
Remove from the tank and place stainless steel
The mask was arranged and fixed to the substrate holder again. Next
Alq for molybdenum resistance heating boat_ThreeTo 200
mg was deposited in a vacuum chamber. In addition, magnesium
Molybdenum resistance heating boat with 1g of ribbon and silver
Tungsten basket with 500mg wire
And were mounted in a vacuum chamber. After that, the vacuum chamber is 1 × 10^-FourP
The pressure was reduced to a. After decompression, Alq _ThreeTwo boats
Heats to 70 ° C and emits light at a deposition rate of 0.1 to 0.3 nm / sec.
Alq on the layer_ThreeIs deposited to a thickness of 40 nm._Threelayer
(Corresponding to an electron injection layer). Continue with silver wire
Energizing the basket and depositing silver at a deposition rate of 0.1 nm / sec.
At the same time as vapor deposition on boat with magnesium ribbon
Energize to deposit magnesium at a deposition rate of 1.4 to 2.0 nm / sec.
Evaporated. By this binary simultaneous evaporation, Alq_ThreeFilm on layer
20-nm thick magnesium-silver layer (corresponding to cathode) formed
Was done. The ITO electrode of this device was used as the anode,
When a direct current of 10 V was applied using the silver layer as a cathode,
Current density of 12 mA / cm^TwoCurrent flows
Blue light with a peak wavelength of 462 nm was obtained. At this time
Has a luminance of 240 cd / m ^TwoAnd the luminous efficiency is 0.64 Lu
-W / W. The resulting luminescence is (DPV)_FourB
(DPV) because it almost matches the solid-state fluorescence of i_FourBi
It was confirmed that light was emitted from.

Application Example 3 Instead of the compound (20) used in the application example 2 as the light emitting layer, a compound represented by the compound (23) obtained in Example 3 was used.
(2,2-di (4-methoxyphenyl) vinyl-3 ′,
Except that 5,5′-tris (2,2-diphenylvinyl) biphenyl (hereinafter abbreviated as (DM-DPV ₃ ) ₄ Bi) was used and the boat temperature at the time of vapor deposition of this compound was changed to 328 ° C. The operation was performed in the same manner as in Application Example 2. When a direct current of 10 V was applied using the ITO electrode of the obtained device as an anode and the magnesium-silver layer as a cathode, the current density was 1
A current of 3 mA / cm ² flows and a peak wavelength of 48
Greenish Blue emission of 5 nm was obtained. At this time, the luminance was 214 cd / m ² and the luminous efficiency was 0.2.
It was 52 lumens / W. The resulting luminescence is (DM-
DPV _{3) 4} and a solid fluorescence Bi since almost conforming (DM-DPV ₃₎ was identified as emission from ₄ Bi.

APPLICATION COMPARATIVE EXAMPLE 1 A transparent supporting substrate was prepared by providing a 100-nm thick ITO film (corresponding to an anode) on a 25 mm × 75 mm × 1.1 mm glass substrate by vapor deposition. This transparent support substrate is subjected to ultrasonic cleaning with isopropyl alcohol for 5 minutes, and further washed in pure water for 5 minutes.
After ultrasonic cleaning for 20 minutes, the substrate was cleaned at a substrate temperature of 150 ° C. for 20 minutes using a UV ion cleaner (manufactured by Samco International). The transparent support substrate is dried with dry nitrogen gas, fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Nippon Vacuum Technology Co., Ltd.), and placed in a molybdenum resistance heating boat with CuPc.
200 mg of TPD and 200 mg of TPD for resistance heating of another molybdenum boat, and further synthesized as a comparative example in another molybdenum resistance heating boat.
-Tris (2,2-diphenylvinyl) biphenyl

[0078]

Embedded image

(Hereinafter, (DPV)_ThreeAbbreviated as B. ) To 20
0 mg was added. Then, the vacuum layer was 4 × 10^-FourReduced to Pa
After applying pressure, energize the heating boat containing CuPc
Heat to 350 ° C. and pass through at a deposition rate of 0.1 to 0.3 nm / sec.
A 20 nm-thick CuPc layer is deposited by evaporation on a bright support substrate.
I did. At this time, the substrate temperature was room temperature. And T
Energize the heating boat with PD and heat up to 215 ° C.
The CuPc layer was heated at a deposition rate of 0.1 to 0.3 nm / sec.
A TPD layer having a thickness of 40 nm is provided by vapor deposition of TPD on the
Was. The substrate temperature at this time was also room temperature. Like this
The two layers of the CuPc layer and the TPD layer provided by
Applicable to layers. Then, (DPV)_ThreeThe module containing B
Energize the heat boat and heat to 245 ° C, evaporation rate 0.1
Vapor deposited on the TPD layer at a rate of ~ 0.3 nm / sec.
nm light emitting layer. Next, the three organic layers are stacked.
Remove the layered transparent support substrate from the vacuum chamber and place it on the light-emitting chamber.
Place a stainless steel mask on the
Fixed to the rudder. Next, a molybdenum resistance heating
Alq_ThreeAnd put 200mg in a vacuum chamber
Was. In addition, molybdenum containing 1g of magnesium ribbon
500mg silver wire and 500mg silver wire
The basket made of tungsten was attached to a vacuum chamber. That
After that, the vacuum chamber is^-FourThe pressure was reduced to Pa. After decompression, A
lq _ThreeHeat the boat containing 270 ° C to the evaporation rate
Alq on the light emitting layer at 0.1 to 0.3 nm / sec_ThreeDepositing a film
Alq with a thickness of 40 nm_ThreeLayer (corresponding to the electron injection layer)
Was. Then, supply electricity to the basket containing silver wire and
At a deposition rate of 0.1 nm / sec, silver is deposited and
Energizing the boat containing the um ribbon and depositing at a rate of 1.4 to 2.0
Magnesium was deposited at nm / sec. This dual simultaneous deposition
As a result, Alq_Three20 nm thick magnesium layer
A silver layer (corresponding to the cathode) was formed. This device's ITO
With the pole as the anode and the magnesium-silver layer as the cathode,
When 10 V was applied, the current density was 5 mA /
cm^TwoPurp with a peak wavelength of 460 nm
light Blue emission was obtained. The luminance at this time is 1
5 cd / m^TwoAnd the luminous efficiency is 0.11 lumen / W
there were. The resulting luminescence is (DPV)_ThreeWith the solid fluorescence of B
Because they almost match (DPV)_ThreeLight emission from B and confirmation
Was done. Thus, a trifunctional styryl compound is more tetrafunctional than
Using a styryl compound as the light-emitting material provides better brightness and
And the luminous efficiency was high.

[0080]

As described above, the EL device using the tetrafunctional styryl compound of the present invention has excellent luminous efficiency and enables high-luminance light emission. Therefore, the tetrafunctional styryl compound of the present invention can be used as an electrophotographic photosensitive member,
It can be used effectively in fluorescent whitening dyes.

[Brief description of the drawings]

FIG. 1 is a mass spectrum of the compound (8) obtained in Example 1.

FIG. 2 Compound (20) obtained in Example 2 obtained in Example 2
3 is a mass spectrometry spectrum.

FIG. 3 is a mass spectrometry spectrum of the compound (23) obtained in Example 3.

FIG. 4 is a mass spectrometry spectrum of the compound (22) obtained in Example 4.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI C07C 17/26 C07C 17/26 25/24 25/24 41/30 41/30 43/166 43/166 43/176 43/176 43/178 43/178 C 43/20 43/20 C 209/68 209/68 211/50 211/50 211/54 211/54 253/30 253/30 255/50 255/50 C07D 209/14 C07D 209 / 14 // C09K 9/02 C09K 9/02 A (56) References JP-A-5-125359 (JP, A) JP-A-3-73595 (JP, A) Synthesis (1988) No. 4 p. 330-p. 331 (58) Fields investigated (Int.Cl. ⁷ , DB name) CA (STN) CAOLD (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A compound of the general formula (I) (In the formula, Ar represents a C 6-20 tetravalent aromatic hydrocarbon group, and R ² , R ³ , R ⁶ , and R ⁷ each represent a hydrogen atom or a substituted or unsubstituted C 6-20 an aryl group or an alkyl group having 1 to 6 carbon atoms, .R ^1, R
⁹ , R ⁴ , R ¹⁰ , R ⁵ , R ¹¹ , R ⁸ , and R ¹² are each a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or 4 to 18 carbon atoms. Represents a heterocyclic group. Here, R ^{1 to} R ¹² may be the same or different from each other. Further, R ¹ and R ⁹ , R ⁴ and R ¹⁰ , R
⁵ and R ¹¹ , and R ⁸ and R ¹² may be each bonded to a substituted group to form a substituted or unsubstituted saturated 5-membered ring or a substituted or unsubstituted saturated 6-membered ring. However,
Except when both R ¹ and R ⁹ , R ⁴ and R ¹⁰ , R ⁵ and R ¹¹ , and R ⁸ and R ¹² are alkyl groups. Here, the substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a phenyl group, an amino group, a cyano group, a nitro group, a hydroxyl group or a halogen. Is shown. These substituents may be single or plurally substituted. A) a tetrafunctional styryl compound represented by the formula: 2. A compound of the general formula (II) (Wherein, R ² , R ³ , R ⁶ , and R ⁷ are the same as described above.
R ¹³ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group, and may be the same or different. ) And a general formula (III) (Wherein R ¹ , R ⁹ , R ⁴ , R ¹⁰ , R ⁵ , R ¹¹ , R ⁸ and R ¹² are the same as above). 2. The method for producing a tetrafunctional styryl compound according to item 1.