JP2927017B2 - New styryl compound, photoreceptor and electroluminescent device using the styryl compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound having a styryl structure. The styryl compound can be used as a light-sensitive material, and more specifically, can be used as a charge-transporting substance for a photoreceptor or an electroluminescent device.

[0002]

2. Description of the Related Art Various organic compounds which can be used as a photosensitive material or a charge transporting material are conventionally known, for example, anthracene derivatives, anthraquinone derivatives, imidazole derivatives, carbazole derivatives, styryl derivatives, styryl derivatives and the like. JP-A-2-154270 discloses the following general formula:

Embedded image [Wherein R _{1 to} R ₅ , Ar ₁ , Ar ₂ and n are those described in the above publication], and JP-A-1-142646 discloses the following general formula:

Embedded image [Wherein, R _{1 to} R ₆ are the same as those described in the above publication], and JP-A-60-98437 discloses the following general formula:

Embedded image [Wherein R _{1 to} R ₄ , Ar ₁ , Ar ₂ and n are those described in the above publication]. However, when the above-mentioned materials are applied to, for example, a photoreceptor, it is basically required that they have excellent photosensitivity or charge transportability,
Furthermore, compatibility with other members, durability, weather resistance, and the like are also required, and there is no material that satisfies such characteristics.

[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 styryl compound which is different from any of the above structures. Another object of the present invention is to provide a photoreceptor using the novel styryl compound. The present invention
It is another object of the present invention to provide an electroluminescence device using the novel styryl compound for a charge transport layer.

[0004]

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

[0005]

Embedded image A styryl compound represented by the formula:

In the general formula [I], Ar ₁ and Ar ₅ each represent an aryl group such as phenyl and naphthyl. Ar ₅ may further be a heterocyclic residue such as thiophene, furan or dioxaindan. These groups may have a substituent such as an alkyl group, an alkoxy group, and a halogen atom. Ar ₂ , Ar ₃ and Ar ₄ each represent an arylene group, for example, an arylene group such as phenylene and naphthylene, and these groups may have a substituent such as an alkyl group, an alkoxy group or a halogen atom.
R ₁ , R ₂ and R ₃ each represent an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, an aralkyl group such as a benzyl group or a phenethyl group, an aryl group such as phenyl or naphthyl;
Or a residue of a heterocyclic ring such as pyrrole or thiophene. These groups are alkyl groups, alkoxy groups,
It may have a substituent such as a halogen atom. R ₃ may further be a hydrogen atom.

Specific examples of the compound having a styryl structure 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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The styryl compound represented by the general formula [I] can be synthesized by a usual method. For example,
The following general formula [II]:

Embedded image [Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , R ₁ and R ₂ have the same meaning as in the above general formula [I]], and the following general formula [III]:

Embedded image [Wherein, Ar ₅ and R ₃ have the same meaning as in the above general formula [I];
₄ and R ₅ represent an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group forming a phosphonium salt. By subjecting the phosphorus compound represented by the formula to a condensation reaction. R ₄ and R _{5 in} the phosphorus compound represented by the general formula [III] are particularly preferably a cyclohexyl group, a benzyl group, a phenyl group, or an alkyl group.

As the reaction solvent in the above method, for example, hydrocarbons, alcohols and ethers are preferable, and 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. Examples of the condensing agent include sodium hydroxide, sodium hydroxide, sodium amide, sodium hydrogen, and alcoholates such as sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, potassium-t-butoxide, and n-butyllithium.

[0018] The reaction temperature can be selected in a wide range from about ⁰ 0 Celsius to about 100 ⁰ C. Preferably 10 to 80 ⁰
C. The compound [II] used in the present invention
I] uses a corresponding quaternary phosphonium salt, for example a triphenylphosphonium salt, instead of the phosphorus compound,
The styryl compound [I] may be synthesized by condensing with the aldehyde compound [II] via the phosphorylene step according to the method of Wittig.

These styryl compounds may be used alone or as a mixture. It is also possible to use a mixture with another charge transporting substance, for example, a hydrazone compound.
The styryl compound represented by the general formula [I] is excellent in photosensitivity and charge transportability, can be used very effectively as a photoconductive material, and is particularly excellent in charge transportability.

The styryl compound represented by the general formula [I] of the present invention can be used as a photosensitive material for a photoreceptor, particularly as a charge transporting substance. Further, it can be used for a charge transporting layer of an electroluminescent element by utilizing its charge transporting property.

First, the case where the styryl compound represented by the general formula [I] is used as a charge transport material of a photoreceptor will be described. Various types of photoconductors are known as the photoconductor, and the styryl compound of the present invention can be applied to any of the photoconductors. 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 styryl compounds of the present invention are used as a charge transport material. The styryl compound acts as a charge transport material,
Charge carriers generated by absorbing light can be transported extremely efficiently.

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

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 quinone pigments , Selenium alloys such as selenium, selenium / tellurium, selenium / 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.

In order to prepare a laminated photoreceptor, a charge generation material is vacuum-deposited on a conductive support, or is applied by dissolving it in a solvent such as an amine, or a pigment must be coated with an appropriate solvent or a suitable solvent. 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 may contain, together with a binder resin, a plasticizer such as halogenated paraffin, polyphenyl biphenyl, dimethylnaphthalene, dibutyl phthalate, O-terphenyl, chloranil, 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 styryl 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 transporting material (2) with a binder, wherein the styryl compound of the present invention is used as a charge transporting material. Used. FIG. 2 shows a function-separated type photoreceptor 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 (6). The charge transport layer (5) contains the styryl compound of the present invention. 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 a surface protective layer on the surface of the photoreceptor of FIG.
(7), and the photosensitive layer (4) is a charge generating layer (6).
And a function-separated type photoconductor having a charge transport layer (5). FIG. 5 shows an intermediate layer between the substrate (1) and the photosensitive layer (4).
(8), the intermediate layer (8) has improved adhesion,
It can be provided to improve coatability, protect the substrate, and improve charge injection 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 styryl compound represented by the general formula [I] of the present invention can be applied to a charge transport layer of an electroluminescence device by utilizing its charge transport property. Hereinafter, a case where the styryl 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 styryl compound between electrodes. FIG. 6 schematically shows an electroluminescent element. In the figure, (11) is an anode,
A charge transport layer (12), an organic light emitting layer (13), and a cathode (14) are sequentially laminated thereon, and the styryl compound represented by the general formula [I] is provided on the charge transport layer. It contains. When a voltage is applied to the anode (1) and the cathode (4), the organic light emitting layer (3) develops color.

Anode of organic electroluminescence 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, or may be formed by spin coating a suitable solution or resin solution of the styryl compound. When formed by a vapor deposition method, the thickness is usually 0.01 to 0.3 μm, and when formed by a spin coating method, the content of the styryl compound to the binder resin is about 20 to 500% 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 connected to each electrode with a suitable lead wire (15) such as a nichrome wire, a gold wire, a copper wire, a platinum wire, etc.
The organic luminescence element emits light when an appropriate voltage (Vs) is applied to both electrodes.

The organic electroluminescent 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
Unless otherwise specified, it means “parts by weight”.

Synthesis Example 1 Synthesis Example of Compound [3]

Embedded image 2.28 g of a phosphonate compound represented by the following formula:

Embedded image Was dissolved in 50 ml of dimethylformamide. While cooling the resulting solution below ^{5 0} C, it was added dropwise to a suspension containing potassium -ter- butoxide 5g in dimethylformamide 70 ml. Then, after stirring at room temperature for 8 hours, the mixture was left overnight. The obtained mixture was added to 900 ml of ice water and neutralized with dilute hydrochloric acid. After about 30 minutes, the precipitated crystals were filtered. The filtration product was washed with water and further purified by recrystallization with acetonitrile to obtain 4.7 g of yellow needle crystals (yield 7).
6%). Melting point (mp) was 83-84 ⁰ C. The results of the elemental analysis are as follows (as C ₄₆ H ₃₈ N ₂ ).

[Table 1] Table 1 {C (%) H (%) N (%)}計算 Calculated 89.32 6.14 4.53 ───────────────────── Experimental 89.28 6.09 4.41 ─────────赤 外 Further, the infrared absorption spectrum of the obtained compound is shown in FIG.

Synthesis Example 2 Synthesis of compound [8]

Embedded image 4.03 g of the phosphonate represented by the formula and 5.44 g of the aldehyde compound represented by the formula 1 were dissolved in 100 ml of dimethylformamide. While cooling the obtained solution to 5 ° C. or lower, a suspension containing 5 g of potassium ter-butoxide in 70 ml of dimethylformamide was added dropwise.
Then, after stirring at room temperature for 8 hours, the obtained mixture was added to 900 ml of ice water and neutralized with dilute hydrochloric acid. After about 30 minutes, the precipitated crystals were filtered, and the obtained main component was washed with water, dissolved in toluene, and separated and purified by silica gel column chromatography (developing solvent: toluene). After distilling off toluene from the effluent, recrystallization from acetonitrile gave 5.6 g of pale yellow crystals (81% yield). Melting point (mp) was 78-80 ° C. The results of the elemental analysis are as follows (as C ₅₂ H ₄₂ N ₂ ).

[Table 2] Table 2 {C (%) H (%) N (%)}計算 Calculated 89.91 6.05 4.03 ───────────────────── Experimental 89.87 6.01 3.95 ─────────赤 外 FIG. 8 shows the infrared absorption spectrum of the compound obtained.

Example 1 Application of Photosensitive Material to Charge Transporting Material Example 1 Bisazo compound represented by the following general formula [A]

Embedded image 0.45 part of a polyester resin (Vylon 200; manufactured by Toyobo Co., Ltd.) and 0.45 part of the resin were dispersed together with 50 parts of cyclohexanone by a sand grinder. The resulting dispersion of the bisazo compound was applied on a 100 μm-thick aluminized mylar using a film applicator so that the dry film thickness was 0.3 g / m ^2, and then dried.

On the charge generation layer thus obtained, 70 parts of styryl compound [2] and polycarbonate resin
(Panlite K-1300; manufactured by Teijin Chemicals Ltd.)
-A solution dissolved in 400 parts of dioxane was dried to a film thickness of 16
It was applied to a thickness of μm and dried to form a charge transport layer. Thus, an electrophotographic photoreceptor having two photosensitive layers was obtained.

The photoreceptor thus obtained was subjected to a commercially available electrophotographic copying machine (EP-470Z, manufactured by Minolta Camera Co., Ltd.).
Corona charging at −6 Kv, initial surface potential V ₀ (V), exposure amount E _1/2 (lux · se
c) Decay rate DD of initial potential when left in the dark for 1 second
R ₁ (%) was measured.

Examples 2 to 4 In the same manner as in Example 1, but with the same constitution, except that styryl compound [2] used in Example 1 was replaced with styryl compounds [3], [4], [6] Were prepared respectively. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 5 A bisazo compound represented by the following general formula [B]:

Embedded image 0.45 parts, polystyrene resin (molecular weight 40000)
45 parts were dispersed together with 50 parts of cyclohexanone by a sand grinder.

The obtained dispersion of the bisazo compound was applied to a thickness of 1
Using a film applicator, the film was coated on a 00 μm aluminized mylar using a film applicator to a dry film thickness of 0.3 g / m ² and then dried. A solution obtained by dissolving 70 parts of a styryl compound [7] and 70 parts of a polyarylate resin (U-100; manufactured by Unitika Ltd.) in 400 parts of 1,4-dioxane is obtained on the thus obtained charge generation layer. It was applied to a thickness of 16 μm and dried to form a charge transport layer. Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced.

Examples 6 to 8 In the same manner as in Example 5, but with the same constitution, except that the styryl compound [7] used in Example 5 was replaced with styryl compounds [8], [9], [10] Were prepared respectively.
V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 9 Polycyclic quinone pigment represented by the following general formula [C]:

Embedded image 0.45 parts, polycarbonate resin (Panlite K-1
3000: Teijin Chemicals Ltd.) 0.45 part of dichloroethane 5
It was dispersed by a sand mill together with 0 parts. The resulting dispersion of the polycyclic quinone pigment was applied onto a 100-μm-thick aluminized mylar using a film applicator so that the dry film thickness was 0.4 g / m ^2, and then dried. A styryl compound is placed on the charge generation layer thus obtained.
[11] A solution prepared by dissolving 60 parts of polyarylate resin (U-100; manufactured by Unitika) in 50 parts of 400 parts of 1,4-dioxane so as to have a dry film thickness of 18 μm is dried, and then dried for charge transport. A layer was formed. Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced.

Examples 10 to 11 In the same manner as in Example 9, except that the styryl compounds [15] and [17] are used instead of the styryl compound [11] used in Example 9, respectively. The body was made. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 12 A perylene pigment represented by the following general formula [D]

Embedded image 0.45 part of butyral resin (BX-1; manufactured by Sekisui Chemical Co., Ltd.) was dispersed in a sand mill together with 50 parts of dichloroethane. The resulting perylene pigment dispersion was applied on a 100 μm-thick aluminized mylar using a film applicator so that the dry film thickness was 0.4 g / m ^2, and then dried. A solution obtained by dissolving 50 parts of a styryl compound [19] and 50 parts of a polycarbonate resin (PC-Z; manufactured by Mitsubishi Gas Chemical Co., Ltd.) in 400 parts of 1,4-dioxane was dried on the charge generation layer thus obtained. Coating was performed so that the film thickness became 18 μm to form a charge transport layer. Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced.

Examples 13 and 14 The same method as in Example 12 was employed, except that the styryl compounds [20] and [25] were used instead of the styryl compound [19] used in Example 12. The body was made. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 15 0.45 part of titanyl phthalocyanine, butyral resin
0.45 part (BX-1; manufactured by Sekisui Chemical Co., Ltd.) was dispersed together with 50 parts of dichloroethane by a sand mill. Using a film applicator, the obtained dispersion of the phthalocyanine pigment was put on an aluminized mylar having a thickness of 100 μm.
The coating was applied so that the dry film thickness became 0.3 g / m ^2, and then dried. On the charge generation layer thus obtained, 50 parts of a styryl compound [30] and a polycarbonate resin (PC
-Z; manufactured by Mitsubishi Gas Chemical Company) 50 parts with 1,4-dioxane 4
The solution dissolved in 00 parts was applied to a dry film thickness of 18 μm to form a charge transport layer. Thus, 2
An electrophotographic photoreceptor having a photosensitive layer composed of layers was prepared.

Examples 16 to 17 In the same manner as in Example 15, except that the styryl compounds [31] and [32] were used instead of the styryl compound [30] used in Example 15, respectively. The body was made. V ₀ , E _1/2 , and DDR ₁ of the photoreceptor thus obtained were measured in the same manner as in Example 1.

Example 18 50 parts of copper phthalocyanine and 0.2 parts of tetranitro copper phthalocyanine were dissolved in 500 parts of 98% concentrated sulfuric acid with sufficient stirring, and the mixture was poured into 5000 parts of water. After precipitating the conductive material composition, it was filtered, washed with water, and dried at 120 ° C. under reduced pressure. 10 parts of the photoconductive composition thus obtained were mixed with 22.5 parts of a thermosetting acrylic resin (Acrydic A405; manufactured by Dainippon Ink) and a melamine resin (Super Beckamine J).
820; manufactured by Dainippon Ink and the like) 7.5 parts, styryl compound
[36] 15 parts were placed in a ball mill pot together with 100 parts of a mixed solvent in which methyl ethyl ketone and xylene were mixed in the same amount, and dispersed for 48 hours to prepare a photosensitive coating solution. This coating solution was applied on an aluminum substrate and dried. About 15μ thick
A photosensitive layer of m was formed to produce a photosensitive member. The photoreceptor thus obtained was subjected to the same method as in Example 1, except that corona charging was performed at +6 Kv, and V ₀ , E _1/2 , and DDR ₁ were measured.

Examples 19 to 21 In the same manner as in Example 18, but having the same constitution, except that the styryl compound [36] used in Example 18 was replaced with styryl compounds [37], [39], and [40] Were prepared respectively. Example 1 of the photoreceptor thus obtained was used.
V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 8.

Comparative Examples 1 to 4 The same composition as in Example 18 except that the styryl compound used in Example 18 was replaced by the following compound
Example 18 except that [E], [F], [G], and [H] were used.
A photoreceptor was produced in exactly the same manner as described above.

Embedded image With respect to the photoreceptor thus obtained, V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 18.

Comparative Examples 5 to 7 In the same manner as in Example 18 and having the same constitution, except that the styryl compound used in Example 18 was replaced by the following compound
A photoconductor was prepared in the same manner as that of Example 18 except that [I], [J] and [K] were used.

Embedded image With respect to the photoreceptor thus obtained, V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 15. Examples 1-2
1. V ₀ , E _1/2 , DD of the photoreceptors obtained in Comparative Examples 1 to 7
Tables 3 and 4 collectively show the measurement results of R ₁ .

[0058]

Table 3 Table 3 −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− V0 (V) E _1/2 (luxsec) DDR ₁ ( %)----------------------Example 1 -650 0.9 3.0 Example 2 -640 2 2.7 Example 3 -650 1.1 3.2 Example 4 -660 1.0 3.0 Example 5 -650 0.8 2.8 Example 6 -640 0.7 3.3 Example 7-650 0.8 3.0 Example 8 -650 0.7 2.9 Example 9 -640 1.3 3.4 Example 10 -660 0.9 2.8 Example 11 -640 1.1 3.5 Example 12 -650 1.4 3.0 Example 13 -640 0.8 3.2 Example 14 -660 0.7 2.7 Example 15 -650 1.0 2.9 Example 16 -660 0. 8 2.5 Example 17 -650 0.9 2.9 Example 18 +610 0.9 13.5 Example 19 +620 0.6 12.0 Example 20 +610 0.5 12.8 Example 21 +630 0 .8 11.7 ---------------------------------------------------------------------------

[0059]

[Table 4] Table _{4 ------------------------------ V0 (V) E 1/2} (luxsec) DDR 1 ( %)---------------------------Comparative Example 1 +620 15.0 12.0 Comparative Example 2 +610 10.2 11. 5.5 Comparative Example 3 +600 6.5 13.7 Comparative Example 4 +610 14.3 12.2 Comparative Example 5 +620 13.4 9.8 Comparative Example 6 +630 7.8 10.0 Comparative Example 7 +610 8.2 11 .7 ---------------------------------------------------------------------------

As can be seen from Tables 3 and 4, the photoreceptor of the present invention has a sufficient charge retention ability, whether it is a laminated type or a single layer type, and has a dark decay rate small enough to be used as a photoreceptor. And the sensitivity is excellent. Furthermore, a commercially available electrophotographic copying machine (Minolta Camera Co., Ltd .; EP-350Z)
Was performed on the photoreceptor of Example 9 by using the photoreceptor of Example 9, and even when 1000 copies were made, the initial and final images had excellent gradation, no change in sensitivity, and a clear image was obtained. This indicates that the photoreceptor of the present invention has stable repetition characteristics.

[0061]

The present invention provides a novel styryl compound. The styryl 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 styryl compound of the present invention is applied to the charge transport layer has excellent 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 diagram 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 in which a photosensitive layer and a surface protective layer are formed on a conductive support.

FIG. 5 is a schematic diagram of a photoconductor in which an intermediate layer and a photosensitive layer are formed on a conductive support.

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

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

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

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 333/20 C07D 333/20 C09K 9/02 C09K 9/02 A G03G 5/06 313 G03G 5/06 313 H05B 33/14 H05B 33/14 A

Claims (3)

(57) [Claims] 1. The following general formula [I]: [Wherein, Ar ₁ represents an aryl group which may have a substituent; Ar ₂ , Ar ₃ and Ar ₄ each represent an arylene group which may have a substituent; Ar ₅ represents a substituent R ₁ and R ₂ each represent an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent; R ₃ represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent. ] The styryl compound represented by these. 2. The following general formula [I]: [Wherein, Ar ₁ represents an aryl group which may have a substituent; Ar ₂ , Ar ₃ and Ar ₄ each represent an arylene group which may have a substituent; Ar ₅ represents a substituent R ₁ and R ₂ each represent an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent; R ₃ represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent. A photoreceptor containing the styryl compound represented by the formula (1) as a charge transporting substance. 3. The following general formula [I]: [Wherein, Ar ₁ represents an aryl group which may have a substituent; Ar ₂ , Ar ₃ and Ar ₄ each represent an arylene group which may have a substituent; Ar ₅ represents a substituent R ₁ and R ₂ each represent an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent; R ₃ represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group which may have a substituent. ] The electroluminescent element containing the styryl compound represented by these as a charge transport material.