JPS63172273A - Photoconductive film and electrophotographic sensitive body using said film - Google Patents

Abstract

PURPOSE:To obtain a photoconductive film having photoconductivity of high sensitivity and an electrophotographic sensitive body using said film by using a specific photoconductive org. compd. CONSTITUTION:The photoconductive film contains at least one kind of the 0-quinodimethane compd. expressed by the formula. In the formula, R1-R6 denote a hydrogen atom, halogen atom, monovalent org. residue or residue in which the adjacent two groups form a condensation ring with the 0- quinodimethane compd. The electrophotographic sensitive body is provided with a photosensitive layer having the photoconductive film contg. at least one kind of the 0-quinodimethane compd. expressed by the formula on a conductive base. Said compd. is used as a photoconductive compd. for electrophotography, more particularly as a carrier generating material, by which the electrophotographic sensitive body having the excellent sensitivity is obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a photoconductive coating containing a novel organic photoconductive compound and an electrophotographic photoreceptor using the same.

"Prior Art and its Problems" As electrophotographic photoreceptors, those having a photosensitive layer containing an inorganic photoconductive compound as a main component, such as ceresin, zinc oxide, or cadmium sulfide, have been widely known. However, these materials are not satisfactory in terms of properties such as thermal stability and durability, and also have problems in production and handling due to their toxicity.

On the other hand, electrophotographic photoreceptors having a photosensitive layer containing an organic photoconductive compound as a main component are relatively easy to manufacture, inexpensive, and easy to handle. It has attracted attention in recent years because it has many advantages such as superior thermal stability. Poly-N-vinylcarbazole is the most well-known such organic photoconductive compound;
．． Electrophotographic photoreceptors having a photosensitive layer containing as a main component a charge transfer complex formed from a Lewis acid such as 7-1-linitro-9-fluorenone have already been put to practical use.

Further, electrophotographic photoreceptors are known that have a functionally separated photosensitive layer of a laminated type or a dispersion type in which the carrier generation function and the carrier transport function of the photoconductor are assigned to separate substances, respectively. For example, an electrophotographic photoreceptor having a photosensitive layer consisting of a carrier generation layer made of an amorphous selenium thin film and a carrier transport layer containing poly-N-vinylcarbazole as a main component has already been put into practical use.

Furthermore, attempts have been made to use organic photoconductive compounds as both the carrier-generating substance and the carrier-transporting substance in the electrophotographic photoreceptor having the above-mentioned functionally separated photosensitive layer.

In this case, carrier generating substances include azo dyes, phthalocyanine dyes, anthraquinone dyes, perylene dyes,
Cyanine dyes, chiapyrylium dyes, squareium dyes, etc. are known. Further, as carrier transport substances, amine derivatives, oxazole derivatives, oxadiazole derivatives, triphenylmethane derivatives, etc. are known.

These carrier-generating substances and carrier-transporting substances are
When it does not have the ability to form a film by itself, it is used in combination with various binders to form a film. Then, an electrophotographic photoreceptor is formed by laminating a layer having a carrier-generating substance and a layer having a carrier-transporting substance on a conductive support, or it contains a carrier-generating substance and a carrier-transporting substance in a dispersed state. 2. Description of the Related Art Electrophotographic photoreceptors formed of layers are known.

However, electrophotographic photoreceptors using organic photoconductive compounds as carrier generating substances still have lower photoconductive sensitivity and durability than those using inorganic photoconductive compounds. Currently, there are very few products that can be put into practical use.

"Object of the Invention" An object of the present invention is to provide a highly sensitive photoconductive coating and an electrophotographic photoreceptor using the same by employing a novel organic photoconductive compound.

"Structure of the Invention" The photoconductive film according to the present invention is characterized by containing at least one type of 0-quinodimethane compound represented by the following general formula (1).

(In the formula, 81 to R6 represent a hydrogen atom, a halogen atom, a monovalent organic residue, or a residue that forms a condensed ring with two adjacent base quinodimethane compounds.) The photographic photoreceptor is characterized in that a photosensitive layer having a photoconductive coating containing at least -fi compounds of the 0-quinodimethane compound represented by the general formula (1) is provided on a conductive support.

Until now, there has been no attempt to use the 0-quinodimethane compound represented by the general formula (1) as a photoconductive compound for electrophotography. It was discovered that an electrophotographic photoreceptor having excellent sensitivity could be obtained by using chlorine as a generating substance, and the present invention was completed.

In the general formula (1), R0 to R6 represent a hydrogen atom, a halogen atom, a monovalent organic residue, or a residue that forms a condensed ring with two adjacent groups or an O-quinodimethane compound, Here, the -valent Yoiki residues include alkyl groups, alkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aralkyl groups, acyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted styryl group, nitro group, hydroxy group, carboxyl group,
Examples include ester groups, cyanogen groups, substituted or unsubstituted arylazo groups, and groups in which the carbon skeletons of these organic residues are substituted with heteroatoms such as nitrogen atoms, oxygen atoms, and sulfur atoms.

Specific examples of the compound represented by the general formula (1) include the following.

H3 The compound represented by the general formula (1) can be synthesized according to the reaction formula shown in FIG. In addition, in the figure, the symbols in the formula have the same meanings as the symbols in the general formula (1). Details of this synthesis method can be found in Anc+ew, Chem,
80.798-799 (1968).

The electrophotographic photoreceptor of the present invention uses the organic photoconductive compound represented by the general formula (1) as a calice generating substance, and can have, for example, the following configuration.

As shown in FIG. 1 or 2, a laminate of a carrier generation layer 2 containing a carrier generation substance as a main component and a carrier transport layer 3 containing a carrier transport substance as a main component on a conductive support 1 is formed. A photosensitive layer 4 is provided. FIG. 1 shows an example in which the carrier transport layer 3 is provided on the carrier generation layer 2, and FIG. 2 shows an example in which the carrier generation layer 2 is provided on the carrier transport layer 3.

As shown in FIG. 3 or 4, a photosensitive layer 4 similar to that described above is provided on a conductive support 1 with an intermediate layer 5 interposed therebetween.

As shown in FIG. 5 or 6, a fine particle carrier generating substance 7 is contained in a layer 6 mainly composed of a carrier transporting substance.
A photosensitive layer 4 formed by dispersing is directly on the conductive support 1,
Alternatively, it is provided via the intermediate layer 5.

The conductive support 1 may be a metal plate, or paper or plastic made conductive by coating, vapor depositing, or laminating a conductive compound such as a conductive polymer or indium oxide, or a metal thin film such as aluminum, palladium, or gold. is used.

The carrier generation layer 2 is formed by forming a carrier generation substance represented by the general formula (1) into fine particles in a dispersion medium using a ball mill, a homomixer, a sand mill, a colloid mill, etc.
If necessary, a dispersion obtained by mixing and dispersing with a binder is applied, or a solution obtained by dissolving a carrier-generating substance into a binder in a solvent is applied by dipping, spraying,
It can be formed by coating using a method such as a spinner method.

In this case, examples of the binder include phenol resin, polyester resin, vinyl acetate resin, polycarbonate resin, polypeptide resin, cellulose resin, polyvinylpyrrolidone, polyethylene oxide, polyvinyl chloride resin, starch, polyvinyl alcohol, acrylic resin, etc. Polymer resin, methacrylic copolymer resin, silicone resin,
Polyacrylonitrile copolymer resin, polyacrylamide, polyvinyl butyral, etc. can be used.

Note that the carrier generation layer 2 can also be formed by forming a compound represented by the general formula (1) into a thin film by a method such as vacuum deposition.

The carrier transport layer 3 can be formed by dispersing or dissolving a carrier transport substance in a binder similar to the above and applying the same. In the present invention, the carrier transport substance is not particularly limited, but for example, amine derivatives, oxazole derivatives, oxadiazole derivatives, triphenylmethane derivatives, etc. can be used.

The intermediate layer 5 disposed between the conductive support 1 and the photosensitive layer 4 has a barrier function and an adhesive function, and is made of, for example, casein, polydonyl alcohol, nitrocellulose, ethylene-acrylic. It can be formed from acid copolymers, polyamides (nylon 6, nylon 66, nylon 610, copolymerized nylons, alkoxymethylated nylons, etc.), polyurethane, gelatin, aluminum oxide, and the like.

Further, the photosensitive layer 4 is formed by dispersing a fine particulate carrier generating substance 7 in a layer 6 mainly composed of a carrier transporting substance, by dispersing or dissolving the carrier transporting substance in the binder as described above, Furthermore, it can be formed by applying a liquid in which a carrier generating substance is dispersed.

"Examples of the invention" Examples 1 to 5 2 parts by weight of butyral resin and 10 parts by weight of isopropyl alcohol
The five types of 0 listed in the table below are added to a solution containing 0 parts by weight.
-Quinodimethane compound (the above structural formulas (2), (3), (
5 parts by weight of the compounds represented by 4), (6), and (9) were ground in a ball mill and dispersed to prepare five types of coating liquids. Then, each coating solution was applied onto a 50 gm AI plate using a doctor blade so that the film thickness after drying was 0.3 um, and dried to form a charge generation layer.

Next, 5 parts by weight of a hydrazone compound represented by the following structural formula and 5 parts by weight of polyvinylcarbazole are dissolved in 70 parts by weight of monochlorobenzene, and this is placed on the charge generation layer so that the film thickness after drying is 20 um. It was coated using a doctor blade as described above and dried to form a charge transport layer.

Next to the five types of electrophotographic photoreceptors obtained in this way,
Electrostatic charging test device (manufactured by Kawaguchi Electric ■, EPA-8100
(type), statically corona-charged to -6 with ■, then observed dark decay for 5 seconds, and set the illuminance to 151'ux.
The photoelectric properties were evaluated by observing the optical attenuation after exposure for 5 seconds. The initial charging potential (VO) and sensitivity (E
l/2) and residual potential (VR) are shown in the table below.

"Effects of the Invention" As explained above, according to the present invention, by using the novel organic photoconductive compound represented by the general formula (1), a photoconductive coating having high sensitivity photoconductivity and An electrophotographic photoreceptor can be obtained using the same. Therefore, the present invention can be widely applied to all electrophotographic application fields such as electrophotographic close-up machines, laser printers, LED printers, and CRT printers.

[Brief explanation of the drawing]

1, 2, 3, 4, 5, and 6 are sectional views showing different specific examples of the layer structure of the electrophotographic photoreceptor according to the present invention, and FIG. 7 is the sectional view according to the present invention. It is a figure showing a reaction formula for synthesizing an 0-quinodimethane compound used in . Figure 1 Figure 3 Figure 5 Figure 2 Figure 6

Claims (2)

[Claims] (1) A photoconductive film characterized by containing at least one type of 0-quinodimethane compound represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (In the formula, R_1 to R_6 are hydrogen atoms, halogen atoms, 1
represents a valent organic residue, or a residue in which two adjacent groups form a condensed ring with the O-quinodimethane compound. ) (2) An electrophotographic photoreceptor characterized in that a photosensitive layer having a photoconductive film containing at least one type of 0-quinodimethane compound represented by the following general formula (1) is provided on a conductive support. . ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (In the formula, R_1 to R_6 are hydrogen atoms, halogen atoms, 1
represents a valent organic residue, or a residue in which two adjacent groups form a condensed ring with the O-quinodimethane compound. )