JPS63155052A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain an org. electrophotographic sensitive body which has an excellent electrification characteristic and is easily producible by providing a photosensitive layer contg. a specific bisazo compd. CONSTITUTION:The electrophotographic sensitive body contains the bisazo compd. expressed by the formula (I). [In the formula (I), X1 denotes a substd. or unsubstd. alkyl group or substd. or unsubstd. phenyl group, X2 denotes a hydrogen atom, -CN group, -CONH2 group, -COOR group or -COR group (R denotes a methyl group or ethyl group), X3 and X4 denote a hydrogen atom; halogen atom; nitro group; alkoxy group or substd. or unsubstd. alkyl group. D denotes an -Ar-Ar- group or -Ar-Y-Ar- group. (Ar denotes a substd. or unsubstd. phenylene group, Y denotes a -CH2- group, -CH=CH- group, -O- group, -CO- group, -COHN- group, -NHCONH- group, -S- group, -S-S- group, -SO- group, -SO2- group or -NH- group.)] The org. photoconductive material which yields the electrophotographic sensitive body having high sensitivity and high durability is thereby obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a photographic photoreceptor. More specifically, the present invention relates to a highly sensitive electrophotographic photoreceptor having a photosensitive layer containing a bisazo compound.

Conventional technology Traditionally, inorganic materials such as selenium, cadmium sulfide, and zinc oxide have been widely used in the photosensitive layer of electrophotographic photoreceptors, but in recent years, organic photoconductive materials such as polyvinyl carbazole have been used. Many attempts have been made to use it in the photosensitive layer of electrophotographic photoreceptors.

The basic characteristics required for an electrophotographic photoreceptor are (I)
(2) The charge caused by corona charging is difficult to attenuate in the dark; (3) the xin is quickly dissipated by light irradiation; (4) light Low residual charge after irradiation1
etc.

Selenium is an inorganic photoreceptor for electrophotography.

Cadmium sulfide, lead oxide, etc. have the basic characteristics mentioned above, but they have manufacturing problems such as being highly toxic, having poor film forming properties, lack of flexibility, and high manufacturing costs. have

On the other hand, research into the use of organic photoconductive materials, typified by polyvinylcarbazole compounds, in the photosensitive layer of electrophotographic photoreceptors has progressed, and some of them have been put into practical use. In general, organic photoconductive materials have advantages over inorganic materials in that they have better transparency, are lighter in weight, are easier to form, and are easier to manufacture into photoreceptors. Despite having such many advantages, organic photoconductive materials have been widely used as electrophotographic photoreceptors.

While the invention seeks to solve the problem, it is desired to develop an organic photoconductive material that provides an electrophotographic photoreceptor with high sensitivity and high durability.

Means for Solving the Problems The present inventors have made earnest efforts to solve the above-mentioned problems, and as a result they have arrived at the present invention.

or a substituted or unsubstituted phenyl group.

X2 is a hydrogen atom, -CN group, -〇 〇 NH2 group,
C0OR group or -〇〇R group (where R represents a methyl group or ethyl group), x3 and x4 represent a hydrogen atom; -logen atom; a nitro group; an alkoke group or a substituted or unsubstituted alkyl group . Or -Ar-Ar- group or -
Represents an Ar-Y-Ar- group. (Here, Ar is a substituted or unsubstituted unison group, and Y is a -CH2- group.

-CH=CH-g, -0- group, -C〇- group, -CO
NH- group.

-NHCONH- group, -8- group, -5-S- group, -80- group.

-5o2- group or -NH- group f: 达su)] is provided.

The present invention will be explained in detail below.

In the formula (I), Xl represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group,
Alkyl groups such as butyl groups; aralkyl groups such as bethyl and phenethyl groups; alkoxyalkyl groups such as methoxyethyl and ethoxynoethyl groups; anoalkyl groups such as anoethyl and abutyl groups; phenyl groups; Examples include substituted phenyl groups such as chlorphenyl, methoxy7phenyl, nitrophenyl, tolyl, and quinolyl.

In the formula CI), X3 and x4 represent a frozen candy atom; a halogen atom; a nitro group; an alkokino group or a substituted or unsubstituted alkyl group; specific examples thereof include a hydrogen atom; a chlorine atom, a bromine atom, Nitro group; Alkyl group such as methyl group, 1fk group, propyl group, butyl group; I-rogenated alkyl group such as chloroethyl group, furomoether group, and group, ethoxy group, propochine group,
Alcoquine groups such as butquine groups are mentioned.

In the formula CI), D is an -Ar-Ar- group or an -Ar-Y-Ar- group, and Ar is a substituted or unsubstituted phenylene group, and examples of the substituent include a methyl group and an ethyl group. Alkyl groups such as chlorine atoms, bromine atoms, etc.; rogen atoms such as chlorine atoms, bromine atoms; alkoxy groups such as metquine groups and ethoxy groups; anlu groups such as acetyl groups and benzoyl groups; nitro groups, sulfonic acid groups, and carboxyl groups. Examples include acid groups.

The bisazo compound represented by the formula CI) can be obtained, for example, as follows. In other words, in the formula (II), the formula (II) has the same meaning as in the above formula (I), and the formula Cu1l) HN-D-NH2C1[l] Produced by campling a tetrazonium salt of an aromatic diamino represented by the formula (Ill), where the insides have the same meanings as in the above formula (I). can do.

The Seiko photographic photoreceptor of the present invention has a photosensitive layer containing one or more bisazo compounds represented by the formula CI).

The Naruko photographic photoreceptor of the present invention will be explained in detail.

Generally, electrophotographic photoreceptors are prepared by providing a subbing layer on a conductive support and laminating a photosensitive layer thereon.

This photosensitive layer is roughly divided into two types: a single-layer photosensitive layer that has charge generation and charge transfer functions, and a two-layer photosensitive layer that has charge generation and charge transfer functions in separate layers. The functional layer is called a charge generation layer, and the layer with a charge transfer function is called a charge transfer layer.

A two-layer type photosensitive layer is also called a functionally separated type, and a single-layer type photosensitive layer is also called a dye-sensitized type or a charge generating agent non-uniformly dispersed type.

The bisazo compound of formula (I) is a single-layer photosensitive layer.

Although it can be applied to any two-layer type photosensitive layer, the case where it is applied to a two-layer type photosensitive layer will be explained first.

The bisazo compound represented by formula (I) and the binder described below are mixed with an organic solvent such as ketones having a boiling point of about 100°C or less (
acetone, methyl ethyl ketone, diethyl ketone, etc.),
Alcohols C (methanol, , THE', ethyl acetate, etc. and deposited on a support provided with an undercoating layer if necessary to a thickness of 0.01 to 1 μm, preferably 0.05 to 0.2 μm.
Apply to a thickness of 300 mL (when dry) and air dry or heat dry (usually 30 mL thick).
(conducted at ~90°C) to form a charge generation layer. Next, a layer known as a charge transfer agent is formed by dissolving a hydrazone compound, an amine compound, a pyrazoline compound, a carbazole compound, and a binder (to be described later) in the above-mentioned organic solvent, and depositing a layer on the charge generation layer to a thickness of 1 to 20 Itm. A charge transfer layer is formed by coating the mixture with a wafer and drying or heating to obtain an electrophotographic photoreceptor having a two-layer type photosensitive layer. (Fig. 1) Next, in the case of a single-layer type photosensitive layer, the compound of formula (1), the charge transfer agent as described above, and the binder described later are dissolved or dispersed in the organic solvent as described above, and if desired, an undercoating is applied. It is coated onto the support provided with the layer to a thickness of 3 to so1tm, preferably 5 to 20 μm (when dry), and air-dried or heated (usually carried out at 30 to 90°C) to form a single-layer photosensitive layer. An electrophotographic photoreceptor is obtained. (Ki 2) The bisazo compound of formula (I) gives particularly good results when applied to a two-layer type photosensitive layer.

In the above, the binder is a vinyl polymer.

Polymers such as polyesters, polycarbonates, and polymethacrylates are used, and the binder thereof is a bisazo compound of general formula (I).

0 for the charge transfer agent or both together.
It is used 3 to 20 times, preferably 0.5 to 5 times (by weight). Further, as the conductive support, a drum or sheet made of metal such as aluminum or copper, or a laminate or vapor deposited product of these metal foils can be used. Furthermore, a subbing layer provided on the support as necessary has a thickness of, for example, 0.5 to
polyurethane, polyacrylonitrile, nylon, phohar, and casein to a thickness of 30 μm (when dry).

Gelatin or the like is dissolved in water or an organic solvent such as DMF, dioxane, THF, etc., and then applied onto a support.

It is provided by heating and drying (usually carried out at 50 to 150°C).

The electrophotographic photoreceptor of the present invention can be used as a photoreceptor for Seiko photography in the same manner as conventional inorganic electrophotographic photoreceptors, and the electrophotographic photoreceptor of the present invention can be used as a photoreceptor for Seiko photography in the same manner as conventional inorganic electrophotographic photoreceptors. The band due to eccentricity is large in quantity and has excellent charge retention properties as well as excellent charge dissipation properties due to light irradiation. In addition, it has excellent resistance to repeated use of fi electric discharges, so it has sufficient practical value as a substitute for conventionally used inorganic electrophotographic photoreceptors. The electrophotographic photoreceptor of the present invention does not lose the characteristics of an organic photoreceptor, such as being transparent and lightweight, having good film-forming properties, and being easy to manufacture.

Example The present invention will be explained in more detail by way of Examples.

In addition, the middle part of the example means parts by weight.

Bisazo compound having the above structure (maximum absorption wavelength s 3
1 part m (in DMF)) shift 5 parts cx le x p 7
The mixture was poured into a solution of 95 parts of saturated polyester resin ("Vylon 200J" manufactured by Toyobo Co., Ltd.) in a solution of 2 parts, and treated in a ball mill for 10 hours to obtain a dispersion.

This dispersion was applied onto a polyester film on which aluminum was vapor-deposited using a wire bar so that the film thickness after drying was 0.2 μm, and dried to form a charge generation layer.

5 parts of the hydrazone compound and 5 parts of polycarbonate resin (Niepilon S-2000J manufactured by Mitsubishi Gas Chemical Co., Ltd.) were dissolved in 70 parts of N,N-dimethylformamide-toluene hot medium (coulometric ratio +:1), and this was dissolved in A charge transfer layer was formed by coating the charge generation layer with a wire coater so that the film thickness after drying was 15 μm and drying.In this way, the electrophotographic photosensitive layer of the present invention having a two-layer photosensitive layer was formed. A photoreceptor was obtained. This photoreceptor was charged by a corona discharge of 16 KV in a dark place, and then exposed to white light. The amount of exposure required for the surface potential to decay to half of the initial surface potential was determined. When half-decreased exposure amount (Z +/2) was measured, S
, 51uX, l1leC.

Examples 2-11 The bisazo compound in Example 1 was replaced.

Xl, X2. An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 1, except that a bisazo compound having a structure corresponding to the following formula (It/) in which X5 and x4 are shown in Table 1 was used. Half-reduced amount of lightning (I!+/2)
was measured. (Table 1) Table 1 Example 12 Electrophotography having a photosensitive layer consisting of two layers in the same manner as in Example 1 except that a pyrazoline compound having the following material formula was used in place of the hydrazone compound in Example 1. When I made a photoconductor and measured the half-life exposure (E1/2), it was 5.
．． +lux, θec.

Example 13 0.1 part of bisazo compound in Example 1 and Example 12
4 parts of the pyrazoline compound in 50 parts of N,N-dimethylformamide-toluene CM amount ratio 1:1) was added to 50 parts of methacrylic resin (Mitsubishi Rayon Co., Ltd. [Acriveso] MDJ).
A dispersion liquid was obtained by adding 4 parts to a bath solution and processing in a ball mill for 20 hours.

This dispersion was applied with a wire bar onto a polyester film on which aluminum had been vapor-deposited so that the film thickness after drying would be 20 μm, and then dried. In this way, a genuine photoreceptor having a photosensitive layer consisting of one layer was prepared, and the half-life exposure (E 1/2 ) was measured to be 8.81 uX, S
ec te was there.

Effects of the Invention: A genuine photoreceptor has been replaced with an organic type photoreceptor which has excellent charging characteristics and is easy to manufacture.

[Brief explanation of the drawing]

Figure 1: Schematic diagram of a two-layer photoreceptor for electrophotography Figure 2: Schematic diagram of a single-layer photoreceptor for electrophotography In Figures 1 and 2, 1: Support 2: Subbing layer 3: Charge generation Layer 4: Charge transfer layer 5: Photosensitive layer.

Claims (1)

[Claims] 1. Formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) [In formula (I), X_1 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group. , X_2 is a hydrogen atom, -CN group, -CONH_2 group, -COOR group or -COR group (where R represents a methyl group or ethyl group), X_3 and X_4 are hydrogen atoms; halogen atoms;
Nitro group; represents an alkoxy group or a substituted or unsubstituted alkyl group. Also, D is -Ar-Ar- group or -Ar-Y
-Ar- represents a group. (Here, Ar is a substituted or unsubstituted phenylene group, Y is a -CH_2- group, -CH=CH
- group, -O- group, -CO- group, -CONH- group, -NH
CONH- group, -S- group, -S-S- group, -SO- group,
-SO_2- group or -NH- group)] An electrophotographic photoreceptor characterized by containing a bisazo compound represented by: -SO_2- group or -NH- group.