JPS5857742B2 - Denshiya Shin Youkoudou Densou - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photoconductive layer for electrophotography containing a novel homopolymer of a carbazole derivative or a copolymer of the carbazole derivative and another vinyl monomer as an active ingredient.

A number of organic photoconductive polymers are known in the art, and these organic photoconductors have various advantages over inorganic photoconductors such as selenium.

That is, this type of organic photoconductor itself has film-forming ability, and the formed film has self-supporting properties, so that it can be used as it is for electrons without using a binding resin or support as in the case of inorganic photoconductors. Since it can be used as a photographic light-sensitive material, it facilitates the production of the light-sensitive material and reduces its manufacturing cost.

Moreover, this film is almost transparent, flexible, and strong, so it can be used as a second original image in diazo copying or as a belt-shaped photosensitive material.

However, since most of these organic photoconductors have too low sensitivity, they have a major practical drawback that they can compete with the highly sensitive inorganic photoconductors.

The present invention eliminates such drawbacks, and not only has the above-mentioned points of the organic photoconductor, but also has sufficient sensitivity and meets almost all the practical requirements in the field of copying and recording. The object of the present invention is to provide an electrophotographic photosensitive material that satisfies the following.

That is, the feature of the photoconductive layer for electrophotography of the present invention is that the homogeneous polymer of N-acrylamidomethylcarbazole represented by formula (1) or the N-acrylamidomethylcarbazole (hereinafter referred to as compound (I)) and other vinyl monomer The main component is a copolymer of

Compound (I) is a new compound that combines the known carbazole represented by formula (n) and NCH-CH represented by formula (III).
C0NHCH20H・・・・・・・・・・・・・・・
...(II) It can be produced by condensation reaction with 1-hydroxymethylacrylamide in a solvent such as tetrahydrofuran, 4-dioxane, acetonitrile, etc. in the presence of a catalyst of p-toluenesulfonic acid at room temperature.

In order to obtain a homogeneous polymer of compound (1), compound (I
) in, for example, N-N dinotylformamide, add α·αl azobisisobutyronitrile (polymerization initiator), and hold at about 80°C for about 10 hours while blowing dry nitrogen, and then It can be poured into a large amount of methanol, and the resulting precipitate can be separated and dried.

Copolymers of compound (I) and other vinyl monomers can be obtained by conventionally well-known polymerization methods.

Note that the vinyl monomers used here include N-vinylcarbazole, N-vinyl 3,6-cyclocarhasol, N-vinyl 3,6-dibromocarbazole, N-vinyl 3,6-dibromocarbazole, and
- N-vinyl carbazole derivatives such as vinyl-3 alkyl carbazole, vinyl anthracene, vinyl phenanthrene, vinyl dibenzothiophene, vinyl naphthalene, vinyl pyrene styrene, methyl acrylate, methyl methacrylate, butyl acrylate-1, butyl methacrylate, acrylonitrile, N-methylol acrylamide, Acrylamide etc. can be used, but this "
When the "other vinyl monomer" does not inherently have photoconductivity, such as styrene, the proportion of compound (I) in the copolymer is preferably 50 mo1% or more.

However, in the case of a photoconductive material such as N-vinylcarbazole, the compound (I
) may be in any range.

The thus obtained homopolymer of compound (I) or copolymer with other vinyl monomers is formed into a film by a conventional method such as a solution casting method (for example, tetrahydrofuran is used as a solvent). Materials are obtained.

In addition, a known dye such as a known Lewis acid such as 2,4,7-trinitrofluorenone or a merocyanine dye may be added to this polymer or copolymer as a sensitizer.

Polymeric materials such as polycarbonate, ethylcellulose and polyurethane can also be added as bond strengtheners.

Further, if necessary, the resulting film can be used as a photoconductive layer, and this can be provided on a support such as a conductively treated paper-film or a bottom plate with or without an adhesive layer.

The photosensitive material obtained by the present invention is as described above, but in order to obtain copies from this photosensitive material, the photosensitive material (or photoconductive layer) is charged and exposed to light using a xerographic method to form an electrostatic latent image. This may be developed with a liquid or powder developer and fixed.

Note that since developer particles remain in the photosensitive material after use, they are removed by cleaning.

It is also possible to provide a photosensitive material having a structure in which the photoconductive layer of the present invention is sandwiched between a support layer and a transparent insulating layer.
Electrophotographic methods using such photosensitive materials include, for example, Japanese Patent Publications No. 42-23910, No. 43-2627, No. 43-24.748, No. 47-17871, No. 48
Various proposals have been made in, for example, Japanese Patent No. 2965-2965.

Examples are shown below.

Example 1 N-dimethylformamide (10TLl) obtained by rectifying N-acrylamidomethylcarbazole (13?) and α·α′-azobisisobutyronitrile (3,0■) represented by formula (I) and kept at 80° C. for 10 hours while blowing dry nitrogen gas.

After cooling, the reaction solution was poured into a large amount of methanol, the resulting scuttling was separated, and after drying, reprecipitation was performed again in a tetrahydrone-methanol system to produce a white powder (1,zP yield 92%).
I got it.

The polymer thus obtained forms a film tougher than, for example, a tetrahydrofuran solution, and is a carbazole derivative (N-
It is a polymer of acrylamide methylcarbazole).

This N-acrylamidomethylcarbazole polymer 0.
5?12.4.7-Dolinitrofluorenone 0.631
is dissolved in 4.51 parts of tetrahydrofuran.

An electrophotographic light-sensitive material was prepared by applying this solution onto a polyester support coated with aluminum using a doctor blade set at an 8 mil gap and removing the solvent.

This photosensitive material for electrophotography was charged with a corona discharge of -6 at room temperature using a device equipped with a tungsten bulb (20 lux) and a surface electrometer (vibration capacitance type).
Thereafter, the amount of surface potential attenuation due to exposure of the tungsten bulb was investigated, and E'/2 (Lux - sec, half-reduced exposure amount) was determined as the sensitivity, and the following results were obtained.

E J/2: 9.8Lux -5ecExample 2 N-acrylamidomethylcarbazole polymer 0.5C1 obtained in Example 1, sensitizer (Japanese Patent Application Laid-Open No. 1203-1983)
Composite dye described in No. 6/f68.2 (p-chlorophenyl)-6-medoxybensohylylium perchlorate and 2-(p-methoxystyryl)-3-phenyl-4-methoxy-6-methyl-1・Composite dye produced from 4-benzopyran) J, 2■ and 2.5% of tetrahydrofuran
It was dissolved in 1.

An electrophotographic light-sensitive material was prepared by applying this solution onto a support made of aluminum-deposited polyester using a doctor blade set at an 8 mil gap and removing the solvent.

This electrophotographic light-sensitive material was processed in the same manner as in Example 1 to obtain E1.
/2, the following results were obtained.

E ] /2: 31.5 Lux -sec Example 3 N-acrylamidomethylcarbazole (1,3!P) represented by formula (1), methyl methacrylate (40■)
, α・α′-azobisisobutyronitrile (to labor)
The mixture was kept at 80° C. for 10 hours while adding rectified N-N-dimethylformamide.

After cooling, the reaction solution was poured into a large amount of methanol, and the resulting scuttling was separated, dried, and reprecipitated again using tetrahydrofuran and methanol to obtain a white powder (12i yield: 90%).

As a result of measuring infrared absorption spectra (film method), poly-N-acrylamidomethylcarbazole (Example 1)
Absorption was observed at 1730 m', which was not observed in the compound obtained in (1), indicating that it is a copolymer.

The polymer obtained here formed a film tougher than, for example, a tetrahydrofuran solution.

0.50 P of this N-acrylamidomethylcarbazole-methyl methacrylate copolymer 2,4,7-trinitrophenanthrenequinone is dissolved in 4651 tetrahydrofuran.

An electrophotographic light-sensitive material was prepared by applying this solution onto a support made of aluminum-deposited polyester using a doctor blade set at an 8 mil gap and removing the solvent.

This electrophotographic light-sensitive material was processed in the same manner as in Example 1 to obtain E1.
/2, the following results were obtained.

Claims (1)

[Claims] 1. A photoconductive layer for electrophotography containing as a main component a homogeneous polymer of N-acrylamidomethylcarbazole or a copolymer of N-acrylamidomethylcarbazole and another vinyl monomer represented by the following formula (2).