JP2812618B2 - Electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor in which a styryl compound having an enamine structure is contained in a photosensitive layer formed on a conductive support. Things.

[0002]

2. Description of the Related Art Conventionally, in electrophotography, selenium, cadmium sulfide, amorphous silicon, zinc oxide and the like, which are inorganic substances, have been widely used in a photosensitive layer of an electrophotographic photosensitive member. However, in recent years, many studies have been made on using an organic photoconductive material as an electrophotographic photosensitive member.

Here, the basic properties required for an electrophotographic photoreceptor are as follows: (1) high chargeability of the charge by corona discharge in a dark place; and (2) charge obtained by the corona charge obtained. Low attenuation in the dark,
(3) that the charge is quickly dissipated by light irradiation;
(4) The residual charge after light irradiation is small, (5) The residual potential increases due to repeated use, the initial potential decreases little, and (6) The change in electrophotographic characteristics due to temperature and humidity is small. It is.

[0004] Conventional inorganic electrophotographic photoreceptors such as selenium and cadmium sulfide have conditions as photoreceptors in terms of basic properties, but have problems in manufacturing, such as strong toxicity and film properties. Difficult, not much plasticity,
It has disadvantages such as high manufacturing cost. Looking further into the future, the depletion of resources has led to a desire for the use of inorganic to organic photoreceptors over these inorganic substances, whose production is limited, and also in terms of toxic pollution.

In view of these points, research on electrophotographic photosensitive members made of organic substances has been actively conducted in recent years.
As a result, electrophotographic photosensitive members using various organic substances have been proposed and some of them have been put to practical use. Generally speaking, organic ones have better transparency than inorganic ones,
It has advantages such as light weight, easy film forming property, positive and negative charging properties, and easy production of a photoreceptor.

As typical examples of organic electrophotographic photoreceptors proposed so far, there are, for example, polyvinyl carbazole and its dielectric, but these are not necessarily sufficient in film property, plasticity, solubility, adhesiveness and the like. In addition, those obtained by sensitizing polyvinyl carbazole with a pyrylium salt dye (Japanese Patent Publication No. 48-25658) and those sensitized with polyvinyl carbazole and 2,4,7-trinitroflorenone (U.S. Pat. No. 3,484,237), but those satisfying the above-mentioned basic properties required of the photoreceptor, such as mechanical strength and high durability, are described below. Not yet obtained.

In recent years, for example, US Pat. No. 3,791,82
As seen in No. 6, so-called function-separated type photoconductors in which the two functions of the photoconductive substance, that is, the generation of carriers and the movement of the generated carriers are performed by different compounds, have been actively proposed. Many of such functionally separated photoreceptor carrier transfer materials are low molecular weight organic compounds, and those that satisfy the basic properties required for photoreceptors from a wide range of compounds are only very limited compounds. .

In Japanese Patent Application Laid-Open No. 2-51162, an electrophotographic photosensitive member having considerable sensitivity has been developed by using a styryl compound containing an enamine group as a carrier transfer material.

[0009]

SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photosensitive member having high sensitivity and high durability. In particular, the photoreceptor of the present invention has excellent stability to temperature and humidity, has high charging characteristics, hardly causes a decrease in photosensitivity even when used repeatedly, and provides a photoreceptor free from deterioration such as missing of a toner image. It is.

The present inventors have studied the above-mentioned photoconductive substance having high sensitivity and high durability, and a styryl compound having a novel enamine structure represented by the following general formula (I) is extremely effective. Then, based on this finding, they made intensive studies and completed the present invention. That is, in the present invention, the photosensitive layer formed on the conductive support has the general formula (I)

[0011]

Embedded image [In the formula, A and B represent a hydrogen atom (excluding the case where both A and B are hydrogen atoms), an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a group having 1 carbon atom. And R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or a group having 1 to 1 carbon atoms. 5 is an alkyl group, R ² is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent, An alkyl group or a hydrogen atom, a is a hydrogen atom or an electron donating substituent,
n is an integer of 1 to 3 (provided that when n is 2 or more, a
May be the same or different, and may form a ring with each other. The present invention provides an electrophotographic photoreceptor comprising an enamine group-containing styryl compound represented by the formula:

The enamine group-containing styryl compound of the general formula (I) according to the present invention can be synthesized by various methods, but can usually be synthesized by the following synthesis process. That is, an aniline derivative (VIII) is obtained by dehydration condensation of a diarylacetaldehyde derivative represented by the following formula (VI) and an aniline derivative represented by the following formula (VII).

[0013]

Embedded image [Wherein, R ¹ , a, and n have the same meanings as described above.] Next, the aniline derivative is subjected to a formylation substitution reaction with phosphorus oxychloride and dimethylformamide or phenylmethylformamide to obtain an aldehyde compound (structural formula (IX), R ² = H).

Alternatively, an acylation substitution reaction is carried out with aluminum chloride and various acid chloride derivatives to obtain a carbonyl compound (structural formula (IX)).

[0015]

Embedded image [Wherein R ¹ , R ² , a, and n have the same meaning as described above. Next, an aldehyde compound represented by the formula (IX) (R ² =
H) or the carbonyl compound is reacted with a Wittig reagent comprising various substituents (formula (X)) to obtain the enamine group-containing styryl compound (I) of the present invention.

[0016]

Embedded image In the definitions of R ¹ , R ² , A and B in the above formulas (I) to (IV), the substituents in the terms “aryl group”, “aralkyl group” and “heterocyclic group” include methyl and ethyl. And lower alkoxy groups such as methoxy and ethoxy. Each of the above groups preferably has one or two of these substituents.

As the "aryl group", C6-C14
(E.g., phenyl, naphthyl, anthryl). As the “aralkyl group”, a phenyl-C _1-3 alkyl group (eg, benzyl,
Phenethyl and the like). The “heterocyclic group” includes a 5- or 6-membered ring having one or two N atoms, and a 5-membered ring having one O, N or S atom. These heterocyclic groups may be condensed with a benzene ring.

Specific examples of the term "optionally substituted aryl group" in the definition of R ¹ , R ² , A and B include phenyl, p-tolyl, p-methoxyphenyl, 3,5- Xylyl, 1-naphthyl, 2-naphthyl, 2-methyl-1
-Naphthyl, 9-anthryl and the like. R ¹ ,
Specific examples of the term “optionally substituted aralkyl group” in the definition of R ² , A and B include benzyl, p-methylbenzyl, p-methoxybenzyl, 3,5-dimethylbenzyl and the like. Can be

The term "alkyl group having 1 to 4 carbon atoms" in the definitions of A and B includes methyl, ethyl, propyl, i-propyl, n-butyl, sec-butyl and the like.
Specific examples of the term "heterocyclic group optionally having substituent (s)" in the definitions of R ¹ and R ² include 1-pyridyl, 2-pyridyl, N-ethyl-3-carbazole, 2-furyl, −
Furyl, 5-methyl-2-furyl, 2-thenyl, 3-
Methyl-2-phenyl, 3-methyl-2-furyl and the like.

In the definition of R ¹ and R ² , the term “C 1-5”
Specific examples of the "alkyl group of" include methyl, ethyl, propyl, i-propyl, n-butyl, sec-butyl,
n-pentyl and the like. Specific examples of the term "electron-donating substituent" in the definition of a include lower alkyl groups such as methyl and ethyl, lower alkoxy groups such as methoxy and ethoxy, N, N-dimethylamino, N, N-diethylamino And the like.

Next, styryl compounds having an enamine structure according to the present invention will be exemplified, but the present invention is not limited thereto.

[0022]

[Table 1]

[0023]

[Table 2]

[0024]

[Table 3]

[0025]

[Table 4]

[0026]

[Table 5]

[0027]

[Table 6]

[0028]

[Table 7]

[0029]

[Table 8]

[0030]

[Table 9]

[0031]

[Table 10]

[0032]

[Table 11]

[0033]

[Table 12]

[0034]

[Table 13]

[0035]

[Table 14]

[0036]

[Table 15]

[0037]

[Table 16]

[0038]

[Table 17]

[0039]

[Table 18]

[0040]

[Table 19]

[0041]

[Table 20] Among these exemplified compounds, in particular, electrophotographic properties, cost,
Those having an excellent synthetic surface are those in which R ¹ is a phenyl group, a p-tolyl group and a p-methoxy group, and R ² is a hydrogen atom, a methyl group, an ethyl group, a phenyl group, a p-tolyl group and a
A methoxyphenyl group, A and B are phenyl groups, p-
And a styryl compound having an enamine structure when a is a hydrogen atom, a methyl group, a methoxy group or a dimethylamino group, which is a tolyl group, a p-methoxyphenyl group, a 1-naphthyl group or a 9-anthryl group.

In addition, it is not easy to directly synthesize an enamine compound by a dehydration condensation with a corresponding acetaldehyde derivative for an enamine group-containing styryl compound in which the enamine moiety is not diaryl but dialkyl or alkyl / aryl. 2 of isomerization and isomerization
A process is required, and there is a problem in synthesis. As will be described later, the styryl compound containing a dialkylenamine group has no problem in sensitivity, but has a problem in durability such as generation of pinholes after 10,000 actual photographing agings. This is considered to be due to the fact that the / arylenamine moiety is not chemically stable and easily decomposed at this position. On the other hand, the photoreceptor using the enamine compound comprising diphenyl of the present invention did not show any pinholes and was chemically stable.

The electrophotographic photoreceptor according to the present invention comprises one or two of the above-mentioned styryl compounds containing an enamine group.
It is obtained by containing more than one kind, resulting in extremely high performance. Further, other styryl compounds (for example, β-
Phenyl- [4- (dibenzylamino)] stilbene,
β-phenyl- [4- (N-ethyl-N-phenylamino)] stilbene, 1,1-bis (4-diethylaminophenyl) -4,4-diphenylbutadiene, a triphenylamine compound (for example, 4-methoxy- 4 '-(4
-Methoxystyryl) triphenylamine, 4-methoxy-4'-styryltriphenylamine) or a hydrazone compound (for example, 4- (dibenzylamino) benzaldehyde-N, N-diphenylhydrazone, 4- (ethylphenylamino) benzaldehyde- N, N-diphenylhydrazone, 3,3-bis [4'-diethylaminophenyl] acrolein-N, N-diphenylhydrazone and the like can also be contained.

Various methods can be considered for using the styryl compound having an enamine structure as an electrophotographic photosensitive member. For example, a styryl compound having an enamine structure and a sensitizing dye, if necessary, by adding a chemical sensitizer or an electron-withdrawing compound, and dissolving or dispersing in a binder resin are provided on a conductive support. Or a sensitizing dye or an azo-based pigment or a pigment represented by a phthalocyanine-based pigment on a conductive support in the form of a laminated structure that can be a carrier generating layer and a carrier moving layer having high charge carrier generation efficiency. If necessary, a styryl compound having an enamine structure of the present invention is dissolved or dispersed in a binder by adding an antioxidant compound or an electron withdrawing compound on the carrier generation layer provided as a carrier generation layer, and this is provided as a carrier transport layer. Although there is a laminated photoreceptor made of such a material, any of these cases can be applied.

In preparing a photoreceptor using the styryl compound having an enamine structure of the present invention, a metal drum,
Coating with the help of a polymeric film-forming binder onto a support such as a metal plate, conductively treated paper, or plastic film. In this case, in order to further increase the sensitivity, it is desirable to add a sensitizer and a substance that imparts plasticity to the binder for forming a polymerizable film as described later to form a uniform photoreceptor film.

These polymerizable film-forming binders include various ones depending on the field of use. That is, in the field of photoconductors for copiers or printers,
Preferred are polystyrene resin, polyvinyl acetal resin, polysulfone resin, polycarbonate resin, polyphenylene oxide resin, polyester resin, alkyd resin, polyarylate resin, and the like. These can be used alone or 2
You may mix and use more than one kind. Among them, polystyrene,
Resins such as polycarbonate, polyarylate, and polyphenylene oxide have a volume resistance of 10 ¹³ Ω or more, and are excellent in film properties, potential characteristics, and the like.

The amount of these binders to be added to the styryl compound having an enamine structure of the present invention is 0.2 to 20 times by weight, preferably 0.5 to 5 times by weight. When the ratio is less than 2, a styryl compound having an enamine structure precipitates from the surface of the photoreceptor, and when the ratio exceeds 20 times, the sensitivity is remarkably reduced. For use in a printing plate, an alkaline binder is particularly required. The alkaline binder is an acidic group soluble in water or an alcoholic alkaline solvent (including a mixed system), for example, an acid anhydride group, a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group, a sulfonamide group, or a sulfonimide group. Is a polymer substance having It is preferable that these alkaline binders usually have a high acid value of 100 or more.

A binder resin having a large acid value easily dissolves in an alkaline solvent or easily swells. Examples of these binder resins include styrene: maleic anhydride copolymer, vinyl acetate: maleic anhydride copolymer, vinyl acetate: crotonic acid copolymer, methacrylic acid: methacrylic acid ester copolymer, phenolic resin, and methacrylic acid. Acid: styrene: methacrylate copolymer and the like. The ratio of these resins to the photoconductive organic substance may be substantially the same as in the case of a photoconductor for a copying machine.

Next, sensitizing dyes added to the photosensitive layer include triphenylmethane dyes represented by methyl violet, crystal violet, night blue and Victoria blue, erythrosine, rhodamine B, rhodamine 3R, acridine orange , Acridine dyes represented by flapeosin and the like, thiazine dyes represented by methylene blue and methylene green, capri blue,
Oxazine dyes such as Meldora Blue, other cyanine dyes, styryl dyes, pyrium salt dyes,
Thiopyrilium salt dyes and the like. In the photosensitive layer, as a photoconductive pigment which generates charge carriers with extremely high efficiency by light absorption, various metal phthalocyanines, metal-free phthalocyanines, phthalocyanine-based pigments such as halogenated metal-free phthalocyanines, perylene imide, perylene anhydride Azo pigments such as perylene pigments, bisazo pigments, and trisazo pigments; quinacridone pigments; and anthraquinone pigments.

In particular, metal-free phthalocyanine pigments, titanyl phthalocyanine pigments, fluorenylidene, bisazo pigments containing a fluorenone ring as pigments that generate charge carriers,
Those using bisazo pigments and trisazo pigments comprising aromatic amines provide high sensitivity and provide excellent electrophotographic photoreceptors. Further, the aforementioned dyes may be used as the charge carrier generating substance. These dyes may be used alone, but they often generate charge carriers with higher efficiency by coexisting with a pigment. Apart from the above-mentioned spectral sensitizers, it is necessary to add various chemical substances for the purpose of preventing an increase in residual potential, a decrease in charge potential, a decrease in sensitivity, etc. for repeated use. .

The substances to be added include tribenzylamine, tetrabenzyl-p-xylenediamine,
-Chloroanthraquinone, benzoquinone, 2,3-dichloronaphthoquinone, naphthoquinone, 4,4'-dinitrobenzophenone, 4,4'-dichlorobenzophenone,
4-nitrobenzophenone, 4-nitrobenzalmalone dinitrile, α-cyano-β- (p-cyanophenyl)
Ethyl acrylate, 9-anthracenylmethylmalondinitrile, 1-cyano-1- (p-nitrophenyl)-
Electron-withdrawing compounds such as 2- (p-chlorophenyl) ethylene and 2,7-dinitrofluorenone;

In addition, an antioxidant, an anti-curl agent, a leveling agent, and the like can be added as necessary to the photosensitive member. The styryl compound having an enamine structure of the present invention is dissolved or dispersed in an appropriate solvent together with the above-mentioned various additives depending on the form of the photoreceptor, and the coating solution is coated on the conductive support described above. And dried to produce a photoreceptor.

As the coating solvent, benzene, toluene,
Aromatic hydrocarbons such as xylene and monochlorobenzene,
Halogenated hydrocarbons such as methylene chloride and dichloroethane, dioxane, dimethoxymethyl ether, solvents such as dimethylformamide alone or as a mixture of two or more solvents or, if necessary, alcohols, acetonitrile, and a solvent such as methyl ethyl ketone are further added and used. be able to.

[0054]

EXAMPLES Next, examples of the present invention will be described in more detail, but the present invention is not limited thereto. Synthesis Example 1 (Exemplified Compound No. 2) Diphenylamine and diphenylacetaldehyde were dehydrated and condensed in benzene under a p-toluenesulfonic acid catalyst to give N- (2,2-diphenylvinyl) -diphenylamine (melting point: 149.0 to 150. 0 ° C.). The compound thus obtained was subjected to formylation with dimethylformamide and phosphorus oxychloride to give 4 [N- (2.2-
[Diphenylvinyl) -N-phenyl] aminobenzaldehyde (melting point: 144.5-145.0 ° C) was obtained. The benzaldehyde compound thus obtained was reacted with potassium-t-butoxide and diethyl p-methylbenzylphosphonate at 0 ° C. in tetrahydrofuran to obtain Exemplified Compound No. 2 (melting point: 78.0-79.0 ° C.).
The recrystallization was performed with ethanol.

Synthesis Example 2 (Exemplified Compound No. 13) 4 [N- (2,2-diphenylvinyl) -N-phenyl] aminobenzaldehyde (synthesized in the same manner as in Synthesis Example 1 above), potassium-t -Butoxide and α
By reacting diethyl-methylbenzylphosphonate in tetrahydrofuran at 0 ° C, Exemplified Compound No. 1
3 (melting point: 103.5-104.5 ° C.) was obtained. The recrystallization was performed with ethanol.

Synthesis Example 3 (Exemplified Compound No. 83) Diphenylacetaldehyde and diphenylamine were dehydrated and condensed in benzene to give N- (2,2-diphenylvinylidene) -N-phenylaniline (melting point: 149.0 to 15).
0.0 ° C). Then, the thus obtained N- (2,
2-Diphenylvinylidene) -N-phenylaniline is formylated with phosphorus oxychloride and dimethylformamide to give 4- [N- (2,2-diphenylvinylidene) -N-phenylamino] -benzaldehyde (mp 144.5-145). 0.0 ° C). Furthermore, 4- [N- (2,2-diphenylvinylidene) thus obtained is obtained.
[N-phenyl] aminobenzaldehyde in tetrahydrofuran is reacted with diethyl α-phenylbenzylphosphonate and potassium-t-butoxide to give Exemplified Compound No. 83 (melting point 120.0-121.
0 ° C.). The recrystallization solvent was ethanol.

Synthesis Example 4 (Exemplified Compound No. 124) N- (2,2-diphenylvinylidene) -N-phenylaniline (synthesized in the same manner as in Synthesis Example 3) was prepared using aluminum chloride and acetyl chloride. Acetylation gives 4- [N- (2,2-diphenylvinylidene) -N
-Phenyl] aminoacetophenone (melting point 142.0-
142.5 ° C). Furthermore, 4-
[N- (2,2-diphenylvinylidene) -N-phenyl] aminoacetophenone in tetrahydrofuran
-Diethyl methylbenzylphosphonate and potassium-t-
Exemplified compound N by reacting with butoxide
o. 124 (mp 135.5-136.5 ° C) was obtained.
The recrystallization solvent was ethanol.

Synthesis Example 5 (Exemplified Compound No. 130) Phenylmethylamine and diphenylacetaldehyde were dehydrated and condensed in benzene in the presence of a p-toluenesulfonic acid catalyst to give N- (2,2-diphenylvinyl) -phenylmethylamine (melting point 93.5-94.5 ° C). Subsequently, formylation was performed using dimethylformamide and phosphorus oxychloride, and 4- [N- (2,2-diphenylvinyl)-
[N-methyl] aminobenzaldehyde was obtained. The thus obtained 4- [N- (2,2-diphenylvinyl)-
[N-methyl] aminobenzaldehyde, potassium-t-
By reacting butoxide and diethyl p-methoxybenzylphosphonate in tetrahydrofuran at 0 ° C., Compound No. 1 is obtained. 130 (melting point 112.5-11
(3.5 ° C.). The recrystallization solvent was ethanol.

Examples 1 to 5 and Comparative Example 1 An aluminum-evaporated polyester film (80 μm thick) was used as a support, and the following structural formula

[0060]

Embedded image Is added to a 1% THF solution in which a phenoxy resin (manufactured by Union Carbide; PKHH) is dissolved in the same amount as the resin, and then a paint conditioner (manufactured by Red Level) having a diameter of 1.5 mm is added. The dispersion was performed for about 2 hours together with the glass beads, and the mixture was applied and dried by a doctor blade method. The film thickness after drying is 0.2
μ. On the pigment layer (charge generation layer), the exemplary compound No. 1, No. 2, No. 3, No. 6,
No. 13, No. 109, no. 124, no. 13
0 and No. Each of 1 g of 133 was coated with a 15% solution of 1.2 g of polyarylate resin (manufactured by Unitika; U-100) in methylene chloride by a squeezing doctor, and a resin-styryl compound solid solution phase having a dry film thickness of 25 μm ( (A charge transfer layer).

The laminated electrophotographic photoreceptor thus produced was subjected to an electrostatic recording paper tester (Kawaguchi Electric; SP-42).
8) The electrophotographic characteristics were evaluated. The measurement conditions were as follows: applied voltage: -6 kV, static: No. 3, from −700 V to −100 by white light irradiation (irradiation light: 5 lux)
Exposure amount E ₁₀₀ required to attenuate the V (lux-sec)
And the initial potential V ₀ (−volt) were measured, and the values are shown in Table 2.
1 is shown.

Further, using the same apparatus, an initial potential V ₀ (−volt) after the same operation was performed 10,000 times with one cycle of charge-discharge (discharge light: irradiation with white light at 40 lux for 1 second) as one cycle. ) And the exposure E ₁₀₀ (looks / second)
₀ and examined the changes in the E _100. As a comparative example, instead of the enamine group-containing styryl compound of the present invention, an enamine group-containing styryl compound having the following structure (melting point of 85 to 87) was used.
An electrophotographic photoreceptor was prepared in exactly the same manner as above except that the charge transfer layer was formed using the method described in JP-A-2-51162, and the electrophotographic properties were measured. The results are shown in Table 21 as Comparative Example 1. .

[0063]

Embedded image

[0064]

[Table 21] From Table 21, there is no remarkable difference in sensitivity and repetition characteristics between the enamine group-containing styryl compound of the present invention and the exemplified enamine group-containing styryl compound of Comparative Example 1. Next, continuous actual photograph aging (10000 times) was performed. Table 2 shows the pinhole occurrence rate per unit area after aging.
2 is shown.

[0065]

[Table 22] As is clear from Table 22 above, continuous real image aging (1
0000 times), the styryl compound of Comparative Example 1 was observed to have a drop phenomenon due to the occurrence of pinholes, indicating that the printing durability was inferior to that of the present invention.

Examples 10 and 11 x-type non-metallic phthalocyanine (manufactured by Dainippon Ink; Fastgen Blue 8) on an aluminum-evaporated polyester film
120) 0.4 g of vinyl chloride: vinyl acetate copolymer resin (manufactured by Sekisui Chemical Co., Ltd .; Eslex M) was added to 30 ml of an ethyl acetate solution in which 0.3 g was dissolved, and dispersed in a paint conditioner for about 20 minutes. It was applied by a doctor blade method, and a charge generation layer was formed so that the film thickness after drying was 0.4 μm.

On the charge generation layer, Compound No. 2
9 and No. 9 A polyarylate layer containing 125% of a styryl compound having an enamine structure of 50% by weight was laminated to prepare a two-layer photoreceptor. The energy (E ₅₀ ) required for halving the potential of the present photoreceptor and the initial potential V ₀ (−volt) were obtained using the 780 nm spectral light. The results are shown in Table 23. The laser printer (WD-580P) manufactured by Sharp was remodeled, the photoreceptor was attached to the drum, and continuous blank copy (Non Co
py Aging) was performed 10,000 times, and then the initial potential decreased.
The degree of decrease in sensitivity was examined. The results are shown in Table 23.

[0068]

[Table 23] As can be seen from this table, the photoconductor was very sensitive and highly charged. Also, in the result of 10,000 continuous blank copies, there was almost no change in the value compared with the first blank copy.

Examples 12 to 20 Anodized aluminum substrate surface (alumite layer: 7)
μ), 1 g of a styryl compound having an enamine structure of the present invention, 1.1 g of a polyarylate resin represented by the following structural formula, and N, N-3,5-xylyl-
3. 4-xylyl-3,4,9,10-perylenetetracarboximide 0.15 g and UV absorber
A solution in which 05 g was dissolved in methylene chloride (an imide compound was partially dispersed) was applied by an applicator to obtain a single-layer photoreceptor having a dry film thickness of 20 μm.

[0070]

Embedded image In this way, the electrophotographic characteristics of the photoreceptor were measured by an electrostatic recording paper test apparatus. The measurement conditions were as follows: applied voltage: +5.5 k
V, static: No. 3 was performed. The exposure amount E ₁₀₀ (lux · second) required to reduce from +700 V to +100 V by white light irradiation was measured, and the value is shown in Table 24. In addition, Perform a blank copy test of 10,000 times, the degree of reduction in sensitivity (E ₁₀₀₎ are also shown in Table 24.

[0071]

[Table 24]

Example 21 and Comparative Example 2 Further, in order to prove the stability of the styryl compound having an enamine structure of the present invention, a stability test of the compound was performed. That is, the styryl compound having an enamine structure of the present invention (exemplified compound No. 83) and the styryl compound having an enamine structure described in JP-A-2-51162 as Comparative Example 2 (used in Comparative Example 1) are organic solvents. Each was dissolved in acetonitrile at the same concentration (including a styryl compound having an enamine structure of about 5% in the solution), left in a dark place at room temperature, and the degree of decomposition after 5 minutes and 3 days was determined by liquid chromatography. The chromatograms are shown in FIGS. 1 to 4 and the results are shown in Table 25.

[0073]

[Table 25] As is clear from the chromatograms of FIGS. 1 to 4 and Table 25, the styryl compound having an enamine structure of the present invention is:
Decomposition is hardly recognized even after 3 days,
It is clear that the content of the styryl compound having an enamine structure described in JP-A-2-51162 used as Comparative Example 1 was reduced by 10%, and decomposition occurred.

[0074]

The photoreceptor using the styryl compound having an enamine structure of the present invention was found to be an electrophotographic photoreceptor having good sensitivity repetition characteristics and excellent sensitivity even in positive charging.

[Brief description of the drawings]

FIG. 1 is a chromatogram of an exemplary compound of the present invention measured by liquid chromatography after 5 minutes.

FIG. 2 is a chromatogram of an exemplary compound of the present invention measured by liquid chromatography three days later.

FIG. 3 is a chromatogram of a conventional exemplary compound measured by liquid chromatography after 5 minutes.

FIG. 4 is a chromatogram of a conventional exemplary compound measured by liquid chromatography three days later.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Akiko Masuda 22-22 Nagaikecho, Abeno-ku, Osaka-shi, Osaka Inside Sharp Corporation (72) Inventor Kazuhiro Enomoto 22-22 Nagaikecho, Abeno-ku, Osaka-shi, Osaka Sharp Corporation (56) References JP-A-2-51162 (JP, A) JP-A-2-184857 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G03G 5/00-5 / 16

Claims (7)

(57) [Claims] 1. A photosensitive layer formed on a conductive support,
General formula (I) [In the formula, A and B represent a hydrogen atom (excluding the case where both A and B are hydrogen atoms), an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a group having 1 carbon atom. And R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or a group having 1 to 1 carbon atoms. 5 is an alkyl group, R ² is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent, An alkyl group or a hydrogen atom, a is a hydrogen atom or an electron donating substituent,
n is an integer of 1 to 3 (provided that when n is 2 or more, a
May be the same or different, and may form a ring with each other. An electrophotographic photoreceptor comprising an enamine group-containing styryl compound represented by the formula: 2. An enamine group-containing styryl compound represented by the formula (II): [Wherein R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or an alkyl group having 1 to 5 carbon atoms. Yes, R ³
Is a hydrogen atom or an electron donating substituent. The electrophotographic photoreceptor according to claim 1, which is a compound of the formula (1). 3. An enamine group-containing styryl compound represented by the formula (III): [Wherein R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or an alkyl group having 1 to 5 carbon atoms. is there. The electrophotographic photoreceptor according to claim 1, which is a compound of the formula (1). 4. An enamine group-containing styryl compound represented by the formula (IV): [Wherein R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or an alkyl group having 1 to 5 carbon atoms. is there. The electrophotographic photoreceptor according to claim 1, which is a compound of the formula (1). 5. A styryl compound containing an enamine group having the formula (V): [Wherein R ¹ is an aryl group which may have a substituent, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent or an alkyl group having 1 to 5 carbon atoms. is there. The electrophotographic photoreceptor according to claim 1, which is a compound of the formula (1). 6. The photosensitive layer contains a carrier transporting substance and a carrier generating substance, wherein the carrier transporting substance has the general formula (I)
The electrophotographic photoreceptor according to claim 1, which is a styryl compound containing an enamine group. 7. A photosensitive layer comprising a carrier generating layer containing a carrier generating substance and a carrier transporting layer containing a carrier transporting substance, wherein the carrier transporting substance is an enamine represented by the general formula (I): The electrophotographic photoreceptor according to claim 1, which is a group-containing styryl compound.