JP2961915B2 - Distyryl compound and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel distyryl compound and a method for producing the same. The distyryl compound of the present invention is specifically an organic photoconductive material for electrophotography,
It can be used as a fluorescent whitening agent, an optical recording material, an electrochromic device, or an electroluminescent device.

[0002]

2. Description of the Related Art Conventionally, various organic compounds usable as a photoconductive material are known, such as anthracene derivatives, anthraquinone derivatives, imidazole derivatives, carbazole derivatives, hydrazone derivatives, styryl derivatives and the like. Asymmetric distyryl compounds are disclosed in JP 175052 or JP-A-62-120346. However, at present, satisfactory characteristics have not been obtained.

[0003]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and has as its object to provide a novel distyryl compound which is different from any of the above structures. Another object of the present invention is to provide a photoreceptor using the novel distyryl compound in a charge transport layer. Another object of the present invention is to provide an electroluminescent device using the novel distyryl compound for a charge transport layer.

[0004]

Means for Solving the Problems The present invention provides the following general formula [I]:

Embedded image [Wherein, R ₁ represents an alkyl group or an aryl group which may have a substituent; R ₂ represents an alkyl group, an aralkyl group or an aryl group which may have a substituent; R ₃ is an alkyl group , A vinyl group, an ethynyl group, a benzyl group, an aryl group which may have a substituent, a furyl group, a thienyl group, an alkoxy group, an aralkyloxy group, a phenoxy group, an alkylthio group, an aralkylthio group or a phenylthio group. And a method for producing the same.

[0005] The distyryl compound represented by the general formula [I] has excellent charge transportability.

In the general formula [I], R ₁ represents an alkyl group such as a methyl group or an ethyl group, or an aryl group such as a phenyl group or a naphthyl. The aryl group may have a substituent such as a lower alkyl group, a lower alkoxy group, a phenyl group, and a halogen atom. R ₂ represents an alkyl group such as a methyl group or an ethyl group, an aralkyl group such as benzyl or phenethyl, or an aryl group such as a phenyl group or a naphthyl group. The aryl group may have a substituent such as a lower alkyl group, a lower alkoxy group, a phenyl group, and a halogen atom. R ₃ is an alkyl group such as a methyl group, an ethyl group or a propyl group, an alkenyl group such as a vinyl group,
Alkynyl group such as ethynyl group, aralkyl group such as benzyl group or phenethyl group, aryl group such as phenyl group or naphthyl group, furan, thiophene or 1,
Heterocyclic residue such as 3-dioxaindane, alkoxy group such as methoxy or ethoxy, benzyloxy group, aralkyloxy group such as phenethyloxy group, phenoxy group, methylthio group, alkylthio group such as ethylthio group,
Represents an aralkylthio group such as a benzylthio group or a phenylthio group. The aryl group may have one or more substituents such as a C1 to C4 alkyl or alkoxy group, a halogen atom, a hydroxyl group, and the like.

Specific examples of the distyryl compound represented by the general formula [I] include those having the following structural formulas.

[0008]

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[0009]

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[0010]

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[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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The distyryl compound represented by the general formula [I] can be synthesized by the following two methods.
That is, the distyryl compound represented by the general formula [I] is represented by the following general formula [II]:

Embedded image [In the formula, R ₁ is the general formula [same meaning as R ₁ in I], R ₄
Represents a lower alkyl group] and the following general formula [III]

Embedded image [Wherein, R ₂ and R ₃ represent R in the general formula [I] of claim 1.
And _2, R ₃ are as defined. And an aldehyde compound represented by the following formula:
The following general formula [IV] or [V]:

Embedded image [Wherein, R ₃ has the same meaning as R ₃ in formula [I]; R ₅ represents a lower alkyl group. ]

Embedded image [Wherein, R ₃ has the same meaning as R ₃ in formula [I]; X represents a halogen atom] and the following formula [VI]:

Embedded image [Wherein, R _1, R ₂ have the same meanings as R _1, R ₂ in the general formula [I]. By reacting with an aldehyde compound represented by the following formula: The phosphorus compound represented by the general formula [II] or [IV] used in the synthesis of the present invention can be easily prepared by heating the corresponding halomethyl compound and trialkyl phosphite directly or in a solvent such as toluene or xylene. Can be manufactured. Trialkyl phosphite as an alkyl group having 1 to 4 carbon atoms,
Particularly, a methyl group and an ethyl group are preferable. The phosphorus compound represented by the general formula [V] can be easily produced by heating the corresponding halomethyl compound and triphenylphosphine directly or in a solvent such as toluene or xylene. The general formula [I obtained as described above
I], [IV] or [a phosphorus compound of the general formula represented by V] [III] or [an aldehyde compound represented by VI], the presence of a basic catalyst, a temperature of about 100 ⁰ C from room temperature To react. As a solvent in the reaction,
For example, hydrocarbons, alcohols, ethers are good,
Methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, bis (2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene, dimethylsulfoxide, N, N-dimethylformamide, N-
Methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and the like can be mentioned. Among them, polar solvents such as N,
N-dimethylformamide and dimethylsulfoxide are preferred. As the basic catalyst (condensing agent), an alcoholate such as sodium hydroxide, potassium hydroxide, sodium amide, sodium hydrogen and sodium methylate, and potassium tert-butoxide is used. The reaction temperature is about ⁰ C
It can be selected from a wide range of up to about 100 ⁰ C.
Preferably from ¹⁰ 0 Celsius to about 80 ⁰ C. The distyryl compound represented by the general formula [I] of the present invention can be used as a charge transport material of a photoreceptor by utilizing its charge transport property, particularly, high photoconductivity at the time of light irradiation. In addition, it can be used for a charge transport layer of an electroluminescence element by utilizing its conductivity.

First, the case where the distyryl compound represented by the general formula [I] is used as a charge transport material for a photoreceptor will be described. Various types of photoreceptors are known as photoreceptors, and the distyryl-based charge transport material of the present invention can be applied to any of the photoreceptors. For example, a single-layer photoreceptor having a photosensitive layer formed by dispersing a charge generating material and a charge transport material in a resin binder on a support, or a charge generating layer having a charge generating material as a main component is provided on a support. And a so-called laminated photoreceptor provided with a charge transport layer thereon. One or more distyryl compounds of the present invention are used as a charge transport material. The distyryl compound acts as a photoconductive substance, and can transport the charge carriers generated by absorbing light extremely efficiently.

Further, since the distyryl compound of the present invention is excellent in ozone resistance and light stability, a photosensitive member excellent in durability can be obtained. Furthermore, the distyryl compound of the present invention has good compatibility with the binder resin, hardly precipitates crystals, and contributes to an improvement in sensitivity.

As the charge generating material, bisazo pigments,
Triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, cyanine dyes, styryl dyes, pyrylium dyes, azo pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinones Organic substances such as pigments, bisbenzimidazole pigments, indathrone pigments, squarium salt pigments, azulene pigments, phthalocyanine pigments, selenium, selenium,
Inorganic substances such as selenium alloys such as tellurium, selenium and arsenic, cadmium sulfide, cadmium selenide, zinc oxide, and amorphous silicon. In addition, any material that absorbs light and generates charge carriers at an extremely high probability can be used.

Examples of suitable binder resins include, but are not limited to, saturated polyester resins, polyamide resins, acrylic resins, ethylene-vinyl acetate resins, ionically crosslinked olefin copolymers (ionomers), styrene −
Thermoplastic resins such as butadiene block copolymer, polycarbonate, vinyl chloride-vinyl acetate copolymer, cellulose ester, polyimide, styrene resin; epoxy resin, urethane resin, silicone resin, phenol resin, melamine resin, xylene resin, alkyd resin Thermosetting resin such as thermosetting acrylic resin; photocurable resin; and photoconductive resin such as polyvinyl carbazole, polyvinyl pyrene, polyvinyl anthracene, and polyvinyl pyrrole. These can be used alone or in combination. These electrically insulating resins were measured alone to be 1 × 10
It is desirable to have a volume resistance of ¹² Ω · cm or more.

In order to produce a single-layer type photoreceptor, fine particles of a charge generating material are dispersed in a resin solution or a solution in which a charge transporting material and a resin are dissolved, and this is coated on a conductive support and dried. Good. At this time, the thickness of the photosensitive layer is 3 to 3
0 μm, preferably 5 to 20 μm. If the amount of the charge generating material used is too small, the sensitivity is poor, and if it is too large, the chargeability is deteriorated, the mechanical strength of the photosensitive layer is reduced, and the proportion in the photosensitive layer is 1 part by weight of the resin. 0.
The range is from 0.01 to 2 parts by weight, preferably from 0.2 to 1.2 parts by weight. The ratio of the charge transporting material is 0.2 to 2 parts by weight, preferably 0.3 to 1.3 parts by weight, based on 1 part by weight of the resin. If the amount is less than 0.2 parts by weight, the sensitivity is poor, and the change in sensitivity during repeated use is large. If the amount is more than 2 parts by weight, the durability is deteriorated, and the surface potential is decreased when used repeatedly.

In order to prepare a laminated photoreceptor, a charge generation material is vacuum-deposited on a conductive support, or is applied by dissolving in a solvent such as an amine. After coating and drying the coating solution prepared by dispersing in the solution in which the binder resin is dissolved if any,
A solution containing a charge transporting material and a binder is coated thereon and dried. At this time, the thickness of the charge generation layer is 4
The thickness is preferably 3 μm or less, more preferably 2 μm or less, and the thickness of the charge transport layer is 3 to 30 μm, and preferably 5 to 50 μm. The proportion of the charge transporting material in the charge transporting layer is 0.2 to 2 parts by weight, preferably 0.3 to 2 parts by weight per 1 part by weight of the binder resin.
1.3 parts by weight.

The photoreceptor of the present invention comprises, together with a binder resin, a plasticizer such as halogenated paraffin, polybiphenyl chloride, dimethylnaphthalene, dibutylphthalate, O-terphenyl, chloranyl, tetracyanoethylene,
Electron-withdrawing sensitizers such as 2,4,7-trinitrofluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, methyl violet, rhodamine B; Sensitizers such as cyanine dyes, pyrylium salts and thiapyrylium salts may be used. As the electrically insulating binder resin used in the present invention, a binder such as a thermoplastic resin or a thermosetting resin, a photocurable resin, or a photoconductive resin known per se, which is electrically insulating, can be used. . As the conductive support used in the photoreceptor of the present invention, a foil or plate of copper, aluminum, silver, iron, nickel or the like in the form of a sheet or a drum is used, or these metals are used as a plastic film. Etc. that are vacuum-deposited, electroless-plated, etc., or those in which a layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is applied or deposited on a support such as paper or a plastic film. Can be

Examples of the constitution of a photoreceptor using the distyryl compound of the present invention are schematically shown in FIGS. Figure 1 shows the substrate
(1) A photoreceptor having a photosensitive layer (4) formed by mixing a photocharge generating material (3) and a charge transport material (2) with a binder, wherein the distyryl compound of the present invention is used as a charge transport material. Used. FIG. 2 shows a function-separated type photoconductor having a charge generation layer (6) as a photosensitive layer and a charge transport layer (5). The charge transport layer (5) is formed on the surface of the charge generation layer (6). I have. The distyryl compound of the present invention is contained in the charge transport layer (5). FIG. 3 shows a function-separated type photoreceptor having a charge generation layer (6) and a charge transport layer (5) as in FIG. 2, but the charge transfer layer (5) has a surface opposite to FIG. A generation layer (6) is formed. FIG. 4 shows that the surface of the photoreceptor of FIG. 1 is further provided with a surface protective layer (7).
A function-separated type photoconductor having (6) and a charge transport layer (5) may be used. FIG. 5 shows that an intermediate layer (8) is provided between the substrate (1) and the photosensitive layer (4). The intermediate layer (8) has improved adhesiveness, improved coating properties, protected the substrate, It can be provided to improve the charge injection property from the substrate to the photosensitive layer.

As the material used for the intermediate layer, polyimide, polyamide, nitrocellulose, polyvinyl butyral, polyvinyl alcohol, aluminum oxide and the like are suitable, and the film thickness is desirably 1 μm or less.

The distyryl compound represented by the general formula [I] of the present invention can be applied to a charge transport layer of an electroluminescent device by utilizing its charge transport property. Less than,
A case where the distyryl-based compound of the present invention is applied to a charge transport layer of an electroluminescence device will be described. The organic electroluminescent element is composed of at least an organic light emitting layer and a charge transport layer containing a distyryl compound between electrodes. FIG. 6 schematically shows an electroluminescent element. In the figure, reference numeral (11) denotes an anode, on which a charge transport layer (12), an organic light emitting layer (13), and a cathode (14) are sequentially laminated. It contains a distyryl compound represented by the general formula [I]. By applying a voltage to the anode (11) and the cathode (14), the organic light emitting layer (13) develops color.

Anode of organic electroluminescent element
As the conductive material used as (11), those having a work function of more than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, copper, zinc,
Tungsten, silver, tin, gold and their alloys,
Tin oxide and indium oxide are used. The metal forming the cathode (14) preferably has a work function of less than 4 eV, and magnesium, calcium, titanium, yttrium, lithium, gadolinium, ytterbium, ruthenium, manganese, and alloys thereof are used. In the organic electroluminescence element, at least the anode (11) or the cathode (14) is a transparent electrode so that light emission can be seen. At this time, if a transparent electrode is used for the cathode, the transparency is likely to be lost. Therefore, it is preferable that the anode be a transparent electrode. In the case of forming a transparent electrode, a conductive material as described above may be formed on a transparent substrate by means of vapor deposition, sputtering, or the like so as to secure a desired light-transmitting property. As a transparent substrate, it has a moderate strength, when producing an electroluminescent element,
It is not adversely affected by heat due to vapor deposition and the like, and is not particularly limited as long as it is transparent.Examples of such a material include a glass substrate and a transparent resin such as polyethylene, polypropylene, polyether sulfone, and polyether ether ketone. It is also possible to use. As a transparent electrode formed on a glass substrate, commercially available products such as ITO and NESA are known, and those may be used.

The charge transport layer (12) is made of the above-mentioned general formula [I]
May be formed by vapor deposition of a distyryl compound represented by the following formula, or by spin coating an appropriate resin solution of the distyryl compound. When formed by the vapor deposition method, the thickness is usually 0.01 to 0.3 μm, and when formed by the spin coating method, the content of the distyryl compound to the binder resin is about 20 to 80% by weight. The thickness may be about 0.05 to 1.0 μm.

An organic light emitting layer is formed on the thus formed charge transport layer (12). As the organic light-emitting material used for the organic light-emitting layer, known materials can be used. For example, epidolidine, 2,5-bis [5,7-di-t-pentyl-2-benzoxazolyl] thiophene, 2,2′- (1,
4-phenylenedivinylene) bisbenzothiazole, 2,
2 ′-(4,4′-biphenylene) bisbenzothiazole,
5-methyl-2- {2- [4- (5-methyl-2-benzoxazolyl) phenyl] vinyl} benzoxazole,
5-bis (5-methyl-2-benzoxazolyl) thiophene, anthracene, naphthalene, phenanthrene, pyrene, chrysene, perylene, perinone, 1,4-diphenylbutadiene, tetraphenylbutadiene, coumarin,
Macridine stilbene, 2- (4-biphenyl) -6-phenylbenzoxazole, aluminum trisoxine, magnesium bisoxin, bis (benzo-8-quinolinol) zinc, bis (2-methyl-8quinolinolate) aluminum oxide, indium tris Oxine, aluminum tris (5-methyloxin), lithium oxine, gallium trioxin, calcium bis
(5-chlorooxin), polyzinc-bis (8-hydroxy-5-quinolinonyl) methane) dilithium epindridione, zinc bisoxin, 1,2-phthaloperinone,
Examples thereof include 2-naphthaloperinone. Also, common fluorescent dyes such as fluorescent coumarin dyes, fluorescent perylene dyes, fluorescent pyran dyes, fluorescent thiopyran dyes,
Fluorescent polymethine dyes, fluorescent merocyanine dyes, fluorescent imidazole dyes and the like can also be used. Among them, particularly preferred are chelated oxinoid compounds. The organic light-emitting layer may have a single-layer structure of the above-described light-emitting substance, or in order to adjust characteristics such as the color of light emission and the intensity of light emission,
It may have a multilayer structure. Next, the above-described cathode is formed on the organic light emitting layer.

As described above, the charge transport layer (12) is provided on the anode (11).
The case where the light emitting layer (13) and the cathode (14) are sequentially laminated to form an organic luminescence element has been described.
A light emitting layer (13), a charge transport layer (12) and an anode may be sequentially laminated on (14). One set of transparent electrodes is made of a suitable lead wire (15) such as nichrome wire, gold wire, copper wire, platinum wire, etc.
And the organic luminescence element is connected to both electrodes with an appropriate voltage.
Light is emitted by applying (Vs). The organic electroluminescence device of the present invention is applicable to various display devices, display devices, and the like. Hereinafter, the present invention will be described with reference to specific examples. In the following examples, “parts” means “parts by weight” unless otherwise specified.

Synthesis Example Synthesis Example of Compound [1]

Embedded image 4.51 g (0.01 mol) of the aldehyde compound and 2.28 g (0.09 g) of diethyl benzylphosphonate
(1 mol) was added and dissolved in 50 ml of dimethylformamide (DMF). While cooling the obtained solution to 5 ° C., a suspension containing 1.68 g of potassium-t-butoxide in 50 ml of dimethylformamide was dropped into the solution. The obtained solution was stirred at room temperature for 4 hours, and then treated at 80 ° C. for 2 hours to complete the reaction. The obtained mixture was added to 500 ml of water, and neutralized with dilute hydrochloric acid. After 30 minutes, the precipitated crystals were filtered. The filtered product was washed with water, dissolved in toluene, and separated and purified by silica gel column chromatography. After distilling off toluene from the effluent, recrystallization from ethanol gave 3.8 g (yield 72.4%) of pale yellow crystals. Melting point was 76-78 ° C. The results of the elemental analysis are as follows (as C ₄₀ H ₃₁ N).

[0034]

[Table 1] Table 1 {C (%) H (%) N (%)}計算 Calculated value 91.43 5.90 2.67 ───────────────────── Experimental value 91.40 5.85 2.75 ───────────────────── ────────────

The infrared absorption spectrum (KBr tablet method) of the product is shown in FIG. The infrared absorption spectrum was measured using a model 1710FTIR (manufactured by PerkinElmer) under the conditions of a resolution of 4 cm ^-1 and five scans.

SYNTHESIS EXAMPLES 2-17 The aldehyde compounds and phosphorus compounds shown in Tables 2 to 5 were used in place of the aldehyde compounds and phosphorus compounds used in Synthesis Example 1, except that A distyryl compound was synthesized. In the table, the melting point, recrystallization solvent, and elemental analysis results of each product are shown. Compounds [2], [4], [9], [21], [23], [2]
4], [27], and [39], the infrared absorption spectra are shown in FIGS. 8 to 15, respectively.

[0037]

[Table 2]

[0038]

[Table 3]

[0039]

[Table 4]

[0040]

[Table 5]

[0041]Application of function-separated photoreceptor to charge transport material  Application Example 1 Bisazo represented by the following general formula [A] as a charge generating substance
Compound:

Embedded image 1 part of polyvinyl butyral resin (BM-2; manufactured by Sekisui Chemical Co., Ltd.) was dispersed in a sand mill together with 50 parts of cyclohexanone and 30 parts of tetrahydrofuran. The obtained dispersion liquid of the bisazo compound was applied on an aluminum drum so as to have a dry film thickness of 0.2 μm, and dried.

On the charge generation layer thus obtained, 2 parts of a distyryl compound [2] as a charge transporting substance and 2 parts of a polycarbonate resin (Panlite K-1300; manufactured by Teijin Chemicals Ltd.) were added to 16 parts of tetrahydrofuran. Apply the mixed and dissolved solution so that the dry film thickness becomes 20 μm,
It was dried to form a charge transport layer. Thus, 2
Thus, an electrophotographic photoreceptor having a photosensitive layer composed of two layers was obtained.
The photosensitive member No. Number one.

Application Examples 2 to 8 Photosensitive members were produced in the same manner as in Application Example 1 except that the distyryl compound [2] in Application Example 1 was replaced with a distyryl compound shown in Table 6 below. Each of the photoconductors obtained in these application examples has the photoconductor No. Numbered 2 to 8.

[0044]

Table 6 Table 6-------------------------------------------------------------------------------------------- 2 3 4 5 6 7 8 ------------------------------------- distyryl [3] [9] [ 15] [21] [23] [30] [39] Compound No. −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−

Comparative Examples 1 to 4 The same procedures as in Application Example 1 were carried out except that the distyryl compound [2] in Application Example 1 was replaced by a charge transport material shown in Table 7 below.
A photoreceptor was produced in the same manner as described above. The photoconductors obtained in these comparative examples were designated as photoconductor Nos. 9-11 are attached.

[0046]

[Table 7]

The photosensitive member No. Nos. 1 to 12 are commercially available electrostatic copying machines (Minolta Camera; EP-47).
0Z), corona charged at −6 KV, initial surface potential V ₀ (V), exposure amount E _1/2 (lux · sec) required to reduce initial potential to １ ／, left in the dark for 1 second Then, the decay rate DDR ₁ (%) of the initial potential was measured. Table 8 shows the measurement results.
Are shown together.

[0048]

Table 8 Table 8 ------------------------------------------------------------------------------------------- V ₀ (V) E _1/2 (lux · sec) DDR ₁ (%) −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− -1 -650 0.8 3.0 2 -650 0.6 3.1 3 -640 0.5 3.44 -650 0.7 2.9 5 -650 0.6 3.0 6 -650 0 5.5 3.27 -660 0.6 2.78 -650 0.7 2.9 9 -650 5.6 3.0 10 -660 3.2 2.5 11 -650 1.8 3.1 12 -650 3.5 2.9 -------------------------------------------------------------------------

As is clear from the above, by applying the distyryl compound of the present invention to the charge transporting material of the photoreceptor, the lamination type or the single layer type has a sufficient charge holding ability and a dark decay rate for the photoreceptor. A photoreceptor that is small enough to be used and that has excellent sensitivity can be obtained.

[0050]Charge transport material for electroluminescent devices
Application  Application Example 9 Distyryl compound on indium tin oxide coated glass
A thin film having a thickness of 500 ° was formed from the product [2] by vapor deposition. Next
Then, aluminum trisoxine is vapor-deposited at 500Å.
A thin film was formed to have a thickness of. Next, as a cathode, Mg and Ag having an atomic ratio of 10: 1 and a thickness of 2 were used.
A thin film of 2,000 mm was formed. In this way, organic
A toroluminescence device was manufactured.

Application Examples 10 to 15 In the application example 9, instead of using the distyryl compound [2], the distyryl compounds [3], [9], [1]
5], [21], [23], and [30], except that the organic electroluminescent device was manufactured in exactly the same manner as in Application Example 1.

Comparative Examples 5 to 7 An organic electroluminescent device was produced in the same manner as in Example 1 except that the following compound was used in place of the distyryl compound [2]. (Comparative Example 5): N-ethylcarbazole-3-carbaldehyde-N-methyl, N-phenylhydrazone (Comparative Example 6): 2,5-bis (p-diethylaminophenyl) -1,3,4-oxadi Azole (Comparative Example 7): N, N, N-tri (p-tolyl) amine

[0053]Evaluation  The electroluminescence device obtained in Application Example 9 was
Using the glass electrode as the anode and applying a bias voltage
5mA / cm^TwoAt a current density of 1 hour. Initial output
Is 0.1 mW / cm^TwoFrom 0.095mW / cm^TwoHas dropped. Sa
When operated for 1 hour, 0.090 mW / cm^TwoDropped to
Was. Similarly, application examples 10 to 12 and comparative examples 5 to 7
Operation tests for the electroluminescent devices
became. Table 9 shows the results.

[0054]

[Table 9]

According to the present invention, when a specific distyryl compound is contained in the charge transporting layer, an organic electroluminescence device having high light emission intensity and excellent durability can be obtained.

[0056]

The present invention has provided a novel distyryl compound. The distyryl compound provided by the present invention can be used for a photoreceptor and a charge transport layer of an electroluminescent device. The photoreceptor to which the distyryl compound of the present invention is applied to the charge transport layer is excellent in the photoreceptor characteristics such as sensitivity, charge transportability, initial surface potential, and dark decay rate, and has less light fatigue upon repeated use.

[Brief description of the drawings]

FIG. 1 is a schematic view of a dispersion type photoconductor in which a photoconductive layer is laminated on a conductive support.

FIG. 2 is a schematic view of a function-separated type photoconductor in which a charge generation layer and a charge transport layer are laminated on a conductive support.

FIG. 3 is a schematic view of a function-separated type photoconductor in which a charge transport layer and a charge generation layer are laminated on a conductive support.

FIG. 4 is a schematic diagram of a photosensitive member having a photosensitive layer and a surface protective layer formed on a conductive support.

FIG. 5 is a schematic diagram of a photosensitive member having an intermediate layer and a photosensitive layer formed on a conductive support.

FIG. 6 shows a schematic sectional view of an electroluminescent element.

FIG. 7 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 8 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 9 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 10 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 11 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 12 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 13 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 14 is a view showing an infrared absorption spectrum of a distyryl compound example of the present invention.

FIG. 15 is a view showing an infrared absorption spectrum of an example of a distyryl compound of the present invention.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 323/29 C07C 323/29 C07D 307/52 C07D 307/52 333/20 333/20 (72) Inventor Keiichi Inagaki Osaka, Osaka 2-3-13 Azuchicho, Chuo-ku, Osaka Osaka Kokusai Building Minolta Camera Co., Ltd. In-house (58) Field surveyed (Int.Cl. ⁶ , DB name) C07C 211/54 C07C 209/68 C07C 213/08 C07C 217 / 80 C07C 319/20 C07C 323/29 C07D 307/52 C07D 333/20 CA (STN) REGISTRY (STN)

Claims (3)

(57) [Claims] 1. The following general formula [I]: [Wherein, R ₁ represents an alkyl group or an aryl group which may have a substituent; R ₂ represents an alkyl group, an aralkyl group or an aryl group which may have a substituent; R ₃ is an alkyl group , A vinyl group, an ethynyl group, a benzyl group, an aryl group which may have a substituent, a furyl group, a thienyl group, an alkoxy group, an aralkyloxy group, a phenoxy group, an alkylthio group, an aralkylthio group or a phenylthio group. The distyryl compound represented by these. 2. The following general formula [II]: [Wherein, R ₁ has the same meaning as R 1 in the general formula [I] of claim ₁ and R ₄ represents a lower alkyl group] and the following general formula [III]: [Wherein, R ₂ and R ₃ represent R in the general formula [I] of claim 1.
And _2, R ₃ are as defined. And an aldehyde compound represented by the following general formula [I]: A method for producing a distyryl compound represented by the formula: 3. The following general formula [IV] or [V]: [Wherein, R ₃ has the same meaning as R ₃ in formula [I] of claim 1; R ₅ represents a lower alkyl group. ] [Wherein, R ₃ has the same meaning as R ₃ in the general formula [I] of claim 1; X represents a halogen atom] and the following general formula [VI]: [Wherein R ₁ and R ₂ represent R 1 in the general formula [I] of claim 1.
₁ and R ₂ have the same meaning. And an aldehyde compound represented by the following general formula [I]: A method for producing a distyryl compound represented by the formula: