JPS60106860A - Hydrazone derivative and production thereof - Google Patents

Abstract

NEW MATERIAL:Hydrazone derivatives of formula I wherein Ar is (substd.) phenyl; R is lower alkyl, benzyl, (substd.) phenyl. EXAMPLE:Compd. of formula III. USE:Charge transfer substances (which form a photosensitive layer together with a charge generating substance, has proper dark place charging potential and rapidly dissipates charges by light irradiation) for use in electrophotographic material. PREPARATION:A hydrazine derivative of formula III is reacted with an equimolar amount of an aldehyde compd. of formula IV in an org. solvent such as lower alcohol, cyclic ether or N,N-dimethylamide.

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a novel human 2-sin compound and a method for producing the same, and more particularly, it relates to a novel human 2-sin compound and a method for producing the same, and more particularly, to a novel human 2-sine compound that is effective as a charge-transfer material in an electrophotographic photoreceptor containing a charge-generating material and a charge-transfer material. This invention relates to a functional human 2sin compound and its production method.

BACKGROUND OF THE INVENTION Conventionally, inorganic materials such as selenium, cadmium sulfide, and zinc oxide have been used as photoconductive materials for photoreceptors used in electrophotography. The "electrophotographic method" referred to here generally refers to a method in which a photoconductive photoreceptor is first charged with "C" by, for example, corona discharge in a dark place, and then imagewise exposed to selectively dissipate the charge only in the exposed areas. It's quiet tm
An image is obtained, and this latent image area is treated with a dye called toner, 1p4q.
This is one of the image forming methods in which an image is visualized using a developing means using electrostatic fine particles made of a colorant and a binder such as a polymeric substance.

In such electrophotography, the basic characteristics required of the photoreceptor are (l) the ability to be charged to an appropriate potential in the dark, (2) less dissipation of charge in the dark, and (3) the ability to charge to an appropriate potential in the dark. ) Examples include scales that quickly dissipate charge when exposed to light. 5 The conventionally used inorganic photoreceptors have many advantages and at the same time various drawbacks, so in recent years, electrophotographic photoreceptors using many organic substances have been proposed and have not been put into practical use. There is something that has been done. Above all, it absorbs light,
A photoreceptor consisting of a substance that generates charge carriers (hereinafter referred to as a charge generation substance) and a substance that accepts and moves the generated charge carriers (hereinafter referred to as a charge transfer substance) generates and moves charge carriers. Compared to photoreceptors made of the same material,
Because materials suitable for each function can be selected from a wide range of materials, it is known to provide unprecedented high sensitivity.

Requirements for the materials used in this type of photoreceptor include that the charge-generating substance absorbs the desired light and generates charge carriers, that the charge carrier generation efficiency is high, and that it is easy to process to produce the photoreceptor. Can be mentioned. On the other hand, the charge transfer substance has the following characteristics: it easily accepts charge carriers from the charge generation substance, the charge carriers move quickly, and it does not absorb in the photosensitive region of the charge generation substance. What should be noted in particular is that suitable charge transfer substances differ depending on the charge generation substance. If the combination of charge-generating material and charge-transfer material is not appropriate, a sufficient charge level may not be obtained in the dark, or the density of the resulting image may be low due to insufficient charge dissipation during light irradiation. , the scalp becomes dirty.

In general, those with a high charge level 4 in the dark tend to have poor charge dissipation, and those with good charge dissipation tend to have a low charge level5. Depends on the moving substance. Practically speaking, the charge level is 4, which is sufficient to dissipate the charge so as not to stain the background, and to obtain sufficient image formation.
An appropriate combination is selected that yields the highest value.

A large number of charge-generating substances have been proposed, and some particularly effective ones include CI Pigment Blue 25 (Color Index 21180), Azo Pigment with Carbasol Bone Core (Japanese Patent Application Laid-open No. 53-95033)! j Azo pigment with phenylamine bone core (JP-A-53-132347), Azo pigment with styrylstilbene bone core (JP-A-53-133445)
Examples include azo pigments having dienyl oxadiazole cores (Japanese Unexamined Patent Publication No. 54-127 "42") and azo pigments having fluorenone cores (Japanese Unexamined Patent Publication No. 54-22834). Different transport materials are suitable for the generation materials.

Purpose The purpose of the present invention is to provide a compound that effectively functions as a charge transfer substance in an electrophotographic photoreceptor, that is, when used together with various charge generation substances, has an appropriate charging potential in the dark and has a high charge potential when irradiated with light. It is an object of the present invention to provide a hydrazone compound whose charge quickly dissipates and a method for producing the same.

Structure The present invention relates to a hydrazone derivative represented by the general formula (1) (wherein Ar represents a 1d-substituted or unsubstituted phenyl group, and R represents a lower alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group), Furthermore, a general compound characterized by reacting a human dielectric conductor represented by the general formula (...) (where Ar and R are the same as the general formula (υ)) and an aldehyde compound represented by the formula (III). The present invention relates to a method for producing a hydrazone derivative represented by formula (1) (wherein Ar and R are the same as above).

Examples of substituents for the phenyl group of Ar or R include alkyl groups such as methyl and ethyl, alkoxy groups such as methoxy and ethoxy, and halogen atoms such as chlorine and bromine.

The hydrazone compound of the present invention is a colorless or pale yellow crystalline substance at room temperature, and is obtained by reacting a hydrazine derivative of the general formula Cl) and an aldehyde compound of the formula (I[l) in an equimolar ratio in a suitable organic solvent. It can be easily obtained by forcing it.

This dehydration condensation reaction can be promoted by adding an acid as is generally known, and for example, an inorganic acid such as hydrochloric acid, dilute sulfurized acid, etc., and an organic acid such as acetic acid are used. As the organic solvent used as the reaction solvent, almost any organic solvent can be used as long as it dissolves the reaction system, including lower alcohols such as methanol and ethanol, 1,4-dioxane, and tetrahydrofuran. Cyclic ethers, cellosolves such as methyl cello sorzo, ethyl cello sorzo, N,N-dimethylformamide,
Examples include acetic acid. The reaction temperature varies depending on the reaction medium; when using N,N-dimethylformamide, etc., which has good solubility in the reaction system, the reaction proceeds at room temperature, and when using ethanol, etc., which has a low solubility in the reaction system at room temperature, the reaction proceeds. It is desirable to heat to reflux. ～・Even in the case of deviation, the reaction is 1 to 5
Finish in time.

Specific examples of the hydrazone compound represented by the general formula (1) thus obtained (A1-8 are as shown below).

CHs Effect The hydrazone compound of the present invention functions effectively as a charge transfer substance in an electrophotographic photoreceptor, and has an appropriate charging potential in the dark when used with various charge generation substances. Moreover, the charge quickly dissipates upon irradiation with light.

Hereinafter, the effects of the present invention will be specifically illustrated by Examples (manufacturing examples of human 2-sin compounds according to the present invention) and Application Examples (applications to electrophotographic photoreceptors).

Example 4-N,N-diphenylnaphthaldehyde 32,4 t
(0.1 mol) was dissolved in 100$ of N,N-dimethylformamide, and 1N salt rR5d was added thereto while stirring! -Methyl-l-phenylhydrazine 14.7
t (0.12 mol) was added dropwise over 30 minutes. After further stirring at room temperature for 1 hour, 200 ml of water was added, and the precipitate precipitated was collected, dried, and recrystallized from ethyl acetate-ethanol to obtain the desired product (compound point 1).

In addition, compound J16. A hydrazone compound of s was obtained. Also, 1,
The hydrazone compound No. 8 was obtained using 1-zienylhydrazine.

The yield, melting point, and elemental analysis values of each hydrazone compound are shown in the table below. The infrared absorption spectrum of the hydrazone compound A1 (KBrj tablet method) is shown.

Application example As a charge generating substance, 76 parts of Guianpuru (CI Pigment Sol-25, CI 21180), 1260 parts of a 2-part tetrahydrofuran solution of polyester 46111 (Vylon 200, manufactured by Toyobo Co., Ltd.) and 3700 parts of tetrahydrofuran were mixed in I-Lumil. The resulting dispersion was applied onto the aluminum surface of the electrically conductive support using a doctor blade and air-dried to form a charge generating layer with a thickness of about 1 μm.

On the other hand, as a charge transfer substance, 2 parts of IFx 1 human dicine compound, polycarbonate resin (1300
, manufactured by Yaodai Co., Ltd.) and 16 parts of Tetoshihyde O7 ton were mixed and dissolved to form a solution, which was then applied onto the charge generation layer using a doctor blade and heated at 80°C for 2 minutes.
Then, it was dried at 105° C. for 5 minutes to form a charge transport layer with a thickness of about 20 μm, thereby producing a photoreceptor tomb 1.

In addition, a total of three types of photoreceptors shown in the table below were prepared by changing the charge transfer substance (hydrazone compound) and charge generation substance.

(Left below) Photoreceptors A1 to A3 thus produced were tested using a commercially available electrostatic copying paper tester (P428 newly manufactured by KK Kawayo Electric Seisakusho).
20 KV or +6 KV corona discharge using
After charging for 2 seconds, leave it in a dark place for 20 seconds,
Measure the surface potential Vpo (volts) at that time, and then irradiate the photoreceptor surface with tungsden lamp light so that the illumination intensity is 4.5 lux, so that the surface potential is 1/2 of Vpo.
The exposure amount E1/2 (looks/second) was calculated by measuring the time (seconds) required for this to occur. The results are shown in Table-3.

Table 3 Each of the photoreceptors described above was printed using a commercially available electrophotographic copying machine, and then light was irradiated through the original image to form an electrostatic latent image. When the developed image (toner image) was electrostatically transferred onto plain paper and fixed, a clear uA transferred image was obtained. A similarly clear transferred image was obtained when a wet developer was used as the developer.

[Brief explanation of the drawing]

The figure shows the infrared absorption spectrum (KBr tablet method) of 41 hydrazone compounds. Procedural Amendment Written January 1, 1980 Kazuo Wakasugi, Commissioner of the Japan Patent Office 1. Indication of the case 1988 Patent No. 214098 2. Relationship to the title of the invention case Patent applicant Nakamagome, Ota-ku, Tokyo 1-3-6 (674) Ricoh Co., Ltd. - Representative Hama 1) Hiro 4, Agent 5, Details of the "Detailed Description of the Invention" of the specification to be amended Contents of the amendment l) No. 17 Correct the charge generating substance column for photoresist 1 in Table 2 on page 1 to "Diane Blue". 2) "Same as photosensitive rest 1" in the charge generating material package of photoreceptor A3 in Table 2 on the same page is corrected. that's all

Claims (1)

[Claims] 16 Represented by the general formula (1) (wherein, Ar represents a substituted or unsubstituted 7-enyl group, and R represents a lower alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group) Hydrazone derivative. 2. A hydrazine derivative represented by the general formula (■n (in the formula, Ar represents a substituted or unsubstituted phenyl group, R represents a lower alkyl group, a benzyl group, or a substituted or unsubstituted phenyl group) and the formula (1) The general formula (
A method for producing a hydrazone derivative represented by [] (wherein Ar and R are the same as in general formula (II)).