JPS63301958A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To prevent deterioration in sensitivity even in the case of using a polymer as a binder by using a specified organometallic polymer as the binder of a pigment, electron donating compd., or electron accepting compd. for a photosensitive body. CONSTITUTION:The photosensitive body contains the organometallic polymer obtained by polycondensing disilane represented by the formula R<1>SiCl2-SiR3<2>, each of R<1> and R<2> being H atom. or a hydrocarbon residue, independent of each other, and at least one of them being a hydrocarbon residue, with an organic boron chloride compound represented by the formula R2<3>BCl2, R<3> being H atom. or a hydrocarbon residue, in the presence of an alkaline metal. The pigment is dispersed into said polymer in the case of a single layer structure, and the layer into which the pigment is dispersed is used as the charge generating layer in the case of a multilayer structure, and said polymer itself is used as the charge transfer layer, and when needed, the electron donating compd. or electron accepting compd. is used or another polymer is used in combination with it, thus permitting the obtained photosensitive body to be high in sensitivity and superior in durability even in the case of using the polymer as the binder.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor. Specifically, the present invention relates to an electrophotographic photoreceptor containing a specific organometallic polymer.

[Conventional technology]

Organic compound-based electrophotographic photoreceptors are made by combining various pigments such as phthalonanine pigments, diazo pigments, and perylene pigments with polyvinyl carbazole, oxadiazole, hydrazone, pyrazoline, etc., and inorganic photoconductors such as selenium and cadmium sulfide. Compared to electrophotographic photoreceptors made of compounds, various combinations have been proposed that have advantages such as non-polluting properties and high productivity, as well as high sensitivity and excellent durability.

[Problem that the invention seeks to solve]

Although the organic compound-based electrophotographic photoreceptors described above are excellent, pigments, oxadiazole, hydrazone, birapurin, etc. alone do not provide a good film, and it is necessary to use various binders.

However, when various known polymers are used as binders, there is a problem in that the sensitivity of the photoreceptor decreases, and there is a desire to develop a more preferable combination of photoreceptors.

[Failure to solve the problem]

The inventors of the present invention have conducted extensive studies on methods for solving the above problems, and have completed the present invention.

That is, the present invention provides general formula R'5iC12-3iR'
+ (wherein R1 and R2 are each independently a hydrogen atom or a hydrocarbon residue, and at least one is a hydrocarbon residue) and a disilane of the general formula R'2B C
It is an electrophotographic photoreceptor containing an organometallic polymer obtained by polycondensing a boron chloride compound represented by I□ (wherein R3 is a hydrogen atom or a hydrocarbon residue) with an alkali metal.

What is important in the present invention is that the electrophotographic photoreceptor contains a specific organometallic polymer.

A single layer structure is achieved by dispersing the pigment in the organometallic polymer described below, and if necessary, an electron-donating compound or an electron-accepting compound is used in combination, or another polymer compound is used as a binder. It's okay. In the case of a multilayer structure, a pigment dispersed in an organometallic polymer (described later) is used as the charge generation layer (at this time, another polymer compound may be used as a binder), and the charge transfer layer is The organometallic polymer itself, which will be described later, is used, or if necessary, an electron-donating compound or an electron-accepting compound is used in combination, or another polymer compound is used as a binder.

In the present invention, the organometallic polymer specified is obtained by polycondensing a disilane represented by the general formula I and a boron chloride compound represented by the general formula (2) with an alkali metal. Each of the chlorides used in the polymerization vessel is known; for example, the former is industrially available trichlorodisilane,
It can be obtained by reacting tetrachlorodisilane, pentachlorodisilane or hexachlorodisilane with a Grignard reagent having a corresponding hydrocarbon residue, followed by distillation separation if necessary, and the latter is an industrially available trihalogenated It can also be obtained by reacting boron with a Grignard reagent having the corresponding hydrocarbon residue, lithium aluminum hydride, aluminum alkyl hydrogen, and the like.

The polycondensation reaction can be produced, for example, by carrying out a reaction similar to the method of dehalogenating polycondensation of dihalogenodisilane (Yoichi Nagai, Photochemistry of Silicon Compounds and its Applications Symposium Abstracts, pages 3-4). In addition, a general method for polycondensation is to use the above-mentioned disilane and boron chloride mixture as raw materials and react them with metals or alloys such as sodium, lithium, magnesium, etc. Then, dehalogenation polycondensation is performed to produce an organometallic polymer. be able to. Here, a part of disilane can also be replaced with dichlorosilane. As a specific method of synthesis, for example, R,
C, West, Comprehensive Orga
nicChemistry, Vol 2. Chapter
r9.4. P365-387 (19B2).

(edited by G, Wilkinson et
al, Pergamon Press+Ne11 Yo
rk).

Various disilane can be used and there are no particular restrictions, such as (CL)3Si-3iCh(CH3), (CH
3) 3Si-5iC1□Chis, (C8-SiR2
3) z(CJs)Si-3iCI□(CIl:l),
(C2H5):l5i-SiCI□(CIl3),
(CH-SiR23) 3si-5iCI□(C3H?
Examples include disilanes such as ) or compounds in which the hydrocarbon residue of these compounds is replaced with another hydrocarbon residue.

In the present invention, the molar ratio of disilane units to boron units in the organometallic polymer is usually about 1:0.01 to 1:1, and if there are too many boron units, a high molecular weight product cannot be obtained, so it is preferable. do not have. It is also possible to replace 0 to 50 mol% of the disilane units with monosilane (dichlorosilane).

In the present invention, it is important to use the above-mentioned organometallic polymer as a dispersion medium for the pigment, electron-accepting compound, or electron-accepting compound of the electrophotographic photoreceptor, or as a charge transfer layer. There are no particular limitations on the electron-accepting compound or the binder used in combination.

Pigments include Abu pigments such as Sudan Red, Guianpuru-, and Jenas Gree B; Quinone pigments such as Algol Yellow, Pyrenequinone, and Indanthrene Brilliant Violet RRP; Indigo pigments such as Quinocyanine pigments; Perylene pigments; Indigo and Thioindigo; and India First Orange. Examples include bisbenzimidazole pigments for toners, phthalocyanine pigments such as copper phthalocyanine and metal-free phthalocyanine, and quinacridone pigments.

Examples of electron-donating compounds include anthracene, pyrene, phenanthrene, coronene, indole, carbazole,
Oxazole, isoxazole, thiazole, imidazole, pyrazole, oxadiazole, birapurin,
Examples include compounds such as thiadiazole and triazole.

Examples of electron-accepting compounds include trinitrofluorenone, dicyanohenzene, tetracyanohenzene, trinitrohenzene, dinitroanthracene, and the like.

Further, binders that can be used in combination include polyester, polystyrene, polyvinyl chloride, polyvinyl acetate, acrylic resin, methylcellulose, polycarbonate, and the like.

The photoreceptor of the present invention is usually produced by coating the above-mentioned single-layer or multilayer photosensitive layer on a conductive support layer. To prevent injection, provide a layer of aluminum oxide, indium oxide, tin oxide, polypropylene resin, acrylic resin, methacrylic resin, polyvinyl chloride resin, epoxy resin, polyester resin, alkyd resin, polyurethane resin, polyimide resin, etc. You can also do it.

〔Example〕

The present invention will be explained below with reference to Examples.

Example 1 Trimethylphenyldichlorodisilane ((C113)2
(C6Hs)Si-5+ (CIli)CI2) and n-
Butyl dichloroboron (1:0.05 molar ratio) was polycondensed with 2 moles of sodium metal in toluene.
Weight average molecular weight in terms of polystyrene measured in C) 7
400 and the boron content is 4 mol%.
0 parts by weight and β-type copper phthalocyanine (manufactured by Toyo Inc. a@,
A solution obtained by dispersing 1 part by weight of Lionol Blue NCB Tonor in 100 parts by weight of toluene was applied onto a 100μ thick aluminum plate using a film applicator, and then dried to form a coating film 8μ thick. Obtained.

The characteristics of the electrophotographic photoreceptor thus obtained were measured using an electrostatic paper analyzer EP manufactured by Kawaguchi Electric ■.
Measured using -8100.

First, a corona discharge of ν at -6 was performed for 2 seconds, and the initial surface potential was measured. After that, it was left in a dark place for 2 seconds, and then passed through a color glass filter IR-80 (manufactured by Hoya Glass) and exposed to an illuminance of 20 lux. The half-life exposure was measured by exposing it to light.

Further, the same operation was performed with corona discharge at +6 kV and measurements were made.

These results are shown in the table.

Example 2 Trimethylphenyldichlorodisilane ((Ct13)z(C6■5)Si-5i(CI(z)
CI□ and (CH3)(C6Hs)CISi-5i (C
H,) 2C1] and n-hexyldichloroboron (molar ratio of disilane and boron is 1:0.1)
A polydisilane with a molecular weight of 5200 and a boron content of 7 mol% as measured by GPC, which was obtained by polycondensation of
A photoreceptor was prepared in the same manner as in Example 1, except that the photoreceptor was used, and its performance was examined. The results are shown in the table.

〔Effect of the invention〕

The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in a wide range of electrophotographic applications such as laser printers, CRT printers, and electrophotographic plate-making systems, and has industrial value. .

Claims (1)

[Claims] 1. Represented by the general formula R^1SiCl_2-SiR^2_3 (wherein R^1 and R^2 are each independently a hydrogen atom or a hydrocarbon residue, and at least one is a hydrocarbon residue.) disilane and the general formula R^3_2BCl
An electrophotographic photoreceptor containing an organometallic polymer obtained by polycondensing a boron chloride compound represented by _2 (wherein R^3 is a hydrogen atom or a hydrocarbon residue) with an alkali metal.