JPH03184945A - New diamino compound - Google Patents

Abstract

NEW MATERIAL:,2-Bias(5-amino-1-naphthyl)ethylene of formula I. USE:An intermediate for disazo compounds useful as a photoconductive material. PREPARATION:(A) 1,2-Bis(5-nitro-1-naphthyl)ethylene synthesized from (1) 5- nitronaphthoaldehyde and (2) diethyl(5-nitro-1-naphthylmethylene)phosphonate and (B) iron powder are suspended in N,N-dimethyl formamide followed by addition of concentrated hydrochloric acid and water and, while stirring vigorous ly, a reaction is made at 80-90 deg.C for 10hr, thus obtaining the objective compound of the formula I. When the present compound is diazotized into a compound of formula II (X is anionic functional group) and this compound is reacted with another compound of formula III (R is H, alkyl, alkoxy, NO2, dialkylamino or halogen; n is 2 or 3), a compound of formula IV useful as a photoconductive material.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to novel diamino compounds. In particular, this compound is useful in the production of disazo compounds useful as photoconductive materials for electrophotographic photoreceptors.

[Prior Art] Inorganic photoreceptors using inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used in electrophotography. ``Electrophotography'' generally refers to a method in which a photoconductive photoreceptor is first charged in a dark place by corona discharge, etc., and then subjected to imagewise exposure to selectively discharge the charges in the exposed areas, leaving the unexposed areas free of electrostatic charge. This is one of the image forming methods in which an image is left behind and this latent image is visualized by a developing means using toner or the like to form an image. The basic characteristics required of the photoreceptor used in such electrophotography are (
1) It can be appropriately charged in the dark, (2) It has excellent charge retention in the dark and there is little discharge of charge, (3) It has high photosensitivity and the charge is quickly discharged by light irradiation. In addition, it has excellent mechanical strength and flexibility.

Although the conventional inorganic photoreceptors have several advantages, they also have various disadvantages.

For example, the selenium photoreceptor currently widely used is the one described above (1
Although the conditions of ) to (3) are satisfied to a considerable extent, the mechanical strength and flexibility are not satisfactory. In particular, as various processes have been adopted in recent electrophotography methods, photoreceptors that are compatible with all of these processes have come to be required.For example, flexible shapes are required. However, the selenium photoreceptor has low flexibility and is difficult to produce in such a shape. Similar drawbacks can also be cited for inorganic photoreceptors other than selenium photoreceptors.

In recent years, in order to eliminate the drawbacks of these inorganic photoreceptors, organic electrophotographic photoreceptors using various organic photoconductive materials have been researched and developed, and have been put into practical use. For example, a photoreceptor in which a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-dolinitrofluoren-9-one is provided on a support (see U.S. Pat. No. 3,484,237). A photoreceptor with a photosensitive layer containing poly-N vinylcarbazole sensitized with a biryllium salt dye (see Japanese Patent Publication No. 48-25658), a photoreceptor with a photosensitive layer containing a disazo pigment as a main component (Japanese Patent Publication No. (see Japanese Patent Application Laid-Open No. 47-10735), and a photoreceptor provided with a photosensitive layer containing a eutectic complex consisting of a dye and a resin as a main component (see Japanese Patent Application Laid-open No. 47-10735).

Among organic photoreceptors, a functionally separated photoreceptor is attracting attention, in which the generation of charge carriers and the movement of the generated charge carriers are performed by a charge generation substance and a charge transfer substance, respectively. Typical configuration examples of this type of photoreceptor include:
One provided with a photosensitive layer containing a charge generation substance and a charge transfer substance, and a layer containing a charge generation substance (charge generation/main layer);
It is known to have a laminated type photosensitive layer in which a layer containing a charge transfer substance (charge transfer layer) is laminated.

[Problems to be Solved by the Invention] Although the conventional organic photoreceptors have improved the mechanical properties and flexibility of the inorganic photoreceptors to a certain extent, they generally have low photosensitivity and do not meet the requirements for electrophotographic photoreceptors. It's not completely satisfying.

In general, the characteristics of an electrophotographic photoreceptor are greatly influenced by the materials used, the manufacturing method, etc., but they are particularly dependent on the photoconductive material.

[Means to solve the problem]

The present inventors have discovered that disazo compounds are extremely effective as photoconductive materials.

The present invention provides novel diamino compounds useful as intermediates for their synthesis.

The present invention is a diamino compound represented by formula (I).

The present invention is a novel compound, which can be converted into a photoconductive material disazo compound, for example, in the following manner. This compound is disazotized to form a tetrazonium salt represented by (X represents an anionic functional group), and then =4- This tetrazonium salt and the general formula (I [I) (R is hydrogen, an alkyl group, an alkoxy group) , represents a nitro group, a dialkylamino group or a halogen, and n is 2 or 3
A compound represented by the formula (IV) (IV) (wherein R and n are the same as above) can be obtained by reacting a compound represented by the formula (IV).

Next, production examples of the compounds of the present invention, as well as melting points, analytical values, and infrared absorption spectra are shown as examples.

[Example] 1 synthesized from 5-nitronaphthaldehyde and diethyl (5-nitro-1-naphthylmethylene) phosphonate
, 2-bis(5-nitro-1-naphthyl)ethylene 18
．． 5gr and 27.9gr of iron powder were suspended in 800mQ of N,N-dimethylformamide, and further added with 10rnQ of concentrated hydrochloric acid.
and 10 d of water were added.

The reaction was carried out at 80-90° C. for 10 hours with vigorous stirring.

The mixture was allowed to cool, the insoluble portion was filtered off, and the solvent of the filtrate was distilled off to obtain yellow crystals. After washing with water and drying, chlorobenzene-N, N
Recrystallization was performed from a -dimethylformamide mixed solvent to obtain yellow needle crystals.

Yield 10.9gr (70.0%) Melting point 253.0-255.0℃ Elemental analysis value (as C,, H,, N) CH-N Actual value 85.15 5.74 8.44 Calculated value ( 85,13) (5,85) (8,64) Infrared absorption spectrum (KBr tablet method) - As shown in Figure 1.

〔Effect of the invention〕

The compounds of the present invention are novel compounds and are useful as intermediates for the synthesis of disazo compounds for photoconductive materials.

[Brief explanation of drawings]

FIG. 1 is an infrared absorption spectrum of the compound of the present invention.

Claims (1)

[Claims] 1. Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A diamino compound represented by