JPS58181051A - Organic photoconductor - Google Patents

Abstract

PURPOSE:To provide high sensitivity in a wavelength region of >=750nm, by using a specified org. photoconductor. CONSTITUTION:A compound represented by the general formula is used as an org. photoconductor. In the formula, X is S, O or Se, each of R1 and R2 is optionally substituted aryl, R3 is optionally substituted aryl or heterocyclic, each of R4-R7 is H, halogen, alkyl or alkoxy, n is 1 or 2, when n is 2, R4 and R4 may be different from each other, and R5 and R5 may be different from each other, and A(-) is an anion.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a pyrylium photoconductor suitable for an electrophotographic photoconductor, particularly a long wavelength photosensitive conductor suitable for an electrophotographic photoconductor used in an electrophotographic printer using a semiconductor laser as a light source. IJ relates to lithium photoconductor.

An abrasive photographic printer that uses a laser as a light source modulates the laser using an fC* signal according to image information, and scans the modulated laser light onto a photoreceptor using a galvano mirror or the like. After forming the Iw layer, a desired regeneration pattern can be formed by sequentially performing toner development and transfer. The lasers used at this time were generally helium-cadmium (oscillation wave:
441.6 nrn) and helium-neon (oscillation 121
1:632.8 nm).

Therefore, is the photoreceptor used for such a light source?
It only needs to be spectrally sensitized to about 65 Qnm, for example, a photosensitive layer using a charge transfer combination of polyvinylcarbazole and trinitrofluoreno/, or a tellurium vapor-deposited layer sensitized by selenium used as a photoreceptor. A photosensitive layer consisting of a selenium vapor-deposited layer formed on a conductive layer as a charge transport layer, and a selenium-tellurium vapor-deposited layer formed on the selenium vapor-deposited layer. Those using sensitized cadmium sulfide in the photosensitive layer, and those using a photosensitive layer that is functionally separated into a charge generation layer and a charge transport layer containing organic pigments and sensitized to long wavelengths. etc. are known.

Incidentally, in recent years, semiconductor lasers have been developed that are small in size, low in cost, and capable of being directly modified. However, this semiconductor laser has an oscillation wavelength of 759 nm.
This makes it difficult to use semiconductor lasers in electrophotographic printers because the photoreceptor as described above has no or almost no sensitivity in the wavelength region of 7501 m or more. ing.

In addition, the photoreceptor is sensitized to increase the sensitivity wavelength range to 7500.
Attempts have been made to make it more than m, but at this time the $1 light layer
The configuration is changed to vIS, and the setting of manufacturing conditions is 1+1i@L
This has the disadvantage that the sensitizing dye used may become dull, or the used sensitizing dye may fade during repeated electrification, making it impossible to perform sensitization using a semiconductor laser.

It also has absorption characteristics on the long wavelength side of 75Qnm or more [2
Generally, organic compounds exhibiting phototetraelectricity with high sensitivity are often unstable against heat and humidity, and have drawbacks such as being complicated to handle.

The object of the present invention is to provide an organic phototetraconductor which eliminates the above-mentioned drawbacks.

Another purpose of this project is to use a ``Kameko photographic method printer V'' using a laser as a light source.
, the barrel electric body is to be used.

Another object of the present invention is to provide an organic photoconductor for an electrophotographic photoreceptor used in an electrophotographic printer VC using a semiconductor laser as a light source having an oscillation wavelength of 75 Qnm or more.

Another object of the present invention is to provide an organic photoconductor for electrophotographic photoreceptors that has high sensitivity in a wavelength range of 750 nm or more.

That is, the present invention is characterized in that a pyrylium dye represented by the following general formula (1) is used as an organic photoconductor.

General formula (1) In the formula, X represents a sulfur atom, an oxygen atom or a selenium atom.

Bulk and cylindrical groups are substituted or unsubstituted aryl groups (phenyl, α-naphthyl, β-naphthyl, tolyl, xylyl, methoxyphenyl, dimethoxyphenyl, chlorophenyl, bromophenyl, dichlorophenyl, cyfromophenyl,)'dichlorophenyl, trichlorophenyl Such)
shows.

The bulk contains substituted or undirected aryl groups (phenyl, α
-naphthyl, β-naphthyl, nottralyl, hrenyl, tolyl, xylyl, biphenyl, methquinophenyl,
Dichlorophenyl, ethoxyphenyl, dichlorophenyl, amylogyphenyl, nitrophenyl, dimethylaminophenyl, diethylaminophenyl, diethylaminophenyl, dipenodylaminophenyl, diphenylaminophenyl, chlorophenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, bromophenyl, cyflomophenyl, etc.) or substituted or unsubstituted heterocyclic groups (3-carbazolyl, 9-methyl-3-carbazolyl, 9-ethyl-3-carbazolyl, 7-nitro-9
-Ethyl-3-carbazolyl, 2-pyridyl, 4-pyridyl, 2-quinolyl, 4-thousandolyl, 3-indolyl, 2-phenyl-3-y)"IJyl, l-methyl-2-phenyl- 3-indolyl, etc.). Melon, 1
(,, Hikone and Toshi are water IC atom, halogen atom (- element atom, bromine atom, fluorine atom), alkyl group (methyl,
(2) Ethyl, propyl, butyl, amyl, hexyl,
octyl, nonyl) or alkoxy groups (methoxy,
Etquin, propoxy, butoxy, amyloki 7, etc.). nVi-, 1 or 2.

, 1. ,. KA8゜O, lζ, □So. Here we go. They may be the same or <, different (3), and the clusters may be the same or different.

Aj represents an interstitial iodine/eg, barchlorate, -fluoroborate, iodide, chloride, bu-ide, sulfute, periodide, (4)P-)luenesulfonate, and the like.

Next, representative examples of the organic light guide of the present invention represented by general formula (1) are shown below.

333- The bi-IJ-IJium dye of the present invention can be obtained, for example, by reacting 2,6-diphenyl-4-methylthiapyrylium salt with 4-diethylaminobenozaldehyde. This reaction can be carried out in the presence of an amine or in a carboxylic anhydride.

1) When attached with the presence of an amine. Various solvents are used as the solvent at this time, but in particular alcohols such as ethanol, nitriles such as acetonitrile, ketones such as methyl ethyl ketone, nitro compounds such as nitrobenzene, halogenated hydrocarbons such as Tetrachloreta 7, etc. are used, preferably alcohols such as ethanol.

Examples of amines include 1,712 and tertiary alkylamines having 1 to 25 carbon atoms such as piperidine, triethylamine, and hexylamine, aromatic h-amino acids having 6 to 25 carbon atoms such as aniline and dimenaline, pyridine, quinoline, etc. Including! Bulk unsaturated IJI ring compounds are used.

The amount of amine is 1'(0,
1-10 mol, preferably 0.5-2 mol H, are used. A large excess of amine may also be used as a solvent. Reaction time is 30 minutes to 10 hours, preferably 1 hour to 3 hours.
The reaction temperature is 1111 tL from around 50° C. to the a stream temperature of the solvent or amine, preferably around the reflux temperature. The solvent is 2,6-diphenyl-4
1 to 100 m, preferably 3 to 1 o, of -methylthiopyrylium salt lf are used.

if) JI@water-gel-bic acid reaction is carried out, the amount of carboxylic anhydride, for example acetic anhydride #''i2.6
-diphenyl-4-methylthiapyrylium salt lf is 1 to 20-1, preferably 2 to 10-1. The reaction time is 1 minute to 1 hour, preferably 3 to 20 minutes. The reaction temperature f ranges from around 80°C to reflux temperature (140°C), preferably around 100°C.

An example of synthesis of a typical biryllium salt used in the present invention will be shown.

Synthesis Example 111 Illustration/16 (to) pyrylium) 2.6
-diphenyl-4-methylpyrylium verchlorate 5
．． 01 and 4-) Methylaminobe/dualdehyde 3.7f
was heated in 140-degree acetic anhydride at 95° C. for 20 minutes.

Next, let it cool and treat the precipitate with vinegar #7 t/anhydrous vinegar 1 t.
1i! = l/l Nyosho recrystallization yielded dye 1.82.

Melting point, 271-272℃ Elemental analysis Molecular formula C, 7mO, NC/calculated value (X
) Experimental value C%) C67,8568,01 H5,O75,11 N 2.93 2.88
Synthesis Example 2 (TiobiIJIJum of the above-mentioned example (4))
BiIJ obtained in Synthesis Example 1
Beryllium 142 ((c)) was dispersed in acetone 150, and sulfurized nose lf was dissolved in 10 m/ml of water, a pressurized liquid was added, and the mixture was stirred for 2 minutes. 20% perchloric acid (15%) and water (150%) were added to this solution, stirred for 1 hour, and left to stand. After filtering the precipitate, it was recrystallized with acetic acid/acetic anhydride=1/1 to obtain dye 1.11.

Melting point 277-281.5℃ Elemental analysis Molecular formula C2,H2,0,N CI S
Calculated value (%) Experimental value (X) C' 65.64 65.88H4,9
14,84 86496,5 These bi-IJ IJ-um dyes exhibit photoconductivity by themselves, and may be used as a photoreceptor by incorporating them into a suitable binder and forming a film. Preference is given to using it as a sensitizer for photoconductive substances. Examples of useful photoconductive materials include cadmium sulfide,
Inorganic photoconductive substances such as zinc oxide, amorphous selenium, selenium alloys, selenium-arsenic, anthracene, pyrene, N-ethylcarbazole, N-ingrovircarbazole, N-
Methyl-N-7enylhydrazino-3-methylidene-9
-Ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-
diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N,N-diphenylhydrazino-3-
Methylidene-1o-ethylphenoxadi/, P-diethylaminobenzaldehyde N, N-diphenylhydrazo/, P-diethylaminobenzaldehyde N-α-
Naphthyl-N-phenylhydrazone, P-pyrrolidinobenzaldehyde-N, N-diphenylhydrazone, 1,
3.3-) Hydrazones such as IJ metelindoleni/-ω-aldehyde-N,N-diphenylhydrazone, P-diethylbenzaldehyde-3-methylbenzthiazolinone-2-hydrazo7, 2,5-bis( P-diethylaminophenyl)-1,3,4-oxadiazole, l-phenyl-3-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline,
1-[quinolyl f211-3- (P-diethylaminostyryl) -5-(P --)ethylaminophenyl)pyrazoline, 1-[pyridyl (21) -3-(P
-diethylaminostyryl) -s-(p-,>ethylaminophenyl)pyrazoline/Nl [6-medoxybilinol+21] -3-(P-diethylaminostyryl) -5-(P-diethylaminophenyl)pyrazoline, l- [pyridyl f3) l) -3=(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[lepidyl f2+) -3-(
P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, i-(pyridyl T21)
-3-(P-diethylaminosteryl)-4-methyl-5-(P-diethylaminophenyl)pyrazoli/,
1-(pyridyl f2+') -3-(α-methyl-P
-diethylaminostyryl')-5-(P-diethylaminophenyl)pyrazoly/% l-phenyl-3-(P
-diethylaminostyryl)-4-, Ifk-5-(P
-diethylaminophenyl)pyrazoline, l-7enyl-3-(α-benzyl-P-1 ethylaminostyryl)
-5-(P-diethylaminophenyl)pyrazoline, spiropyrazoline and other pyrazolines, 2-(P-diethylaminostyryl)-6-ethylaminopenzuoxazole, 2-(P-diethylaminophenyl)-4-(
Oxazole compounds such as P-diethylaminophenyl)-5-(2-p-rollophenyl)oxazole, 2-(
Thiazole compounds such as P-diethylaminostyryl)-6-dinithylaminobenzothiazole, triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, 1.1-bis(4-
N,N-diethylamino-2-methylphenyl)hebuta/, 1.1.2° 2-Tetrakis(4,-N,N-dimethylamine-2-methylphenyl)ethane and other polyarylalkalka/@,tri Low molecular weight organic photoconductive substances such as phenylamine or poly-N-vinylcarbazole, polyvinylpyrene, polyvinyl acetal/, polyvinylpyrenedi/, poly-9-vinylphenylanthracene, helenol formaldehyde N 1ift, ethylcarbazole formaldehyde ginger Examples include polymeric organic photoconductive substances such as. The biryllium dye in the composition can generally be contained in the film-forming composition in a proportion of 0.0001 to 30% by weight, with a preferred content of 0.05 to 50% by weight.

The binder contained in the composition can be selected from a wide range of film-forming resins. Specific examples of resins that can be used include polyvinyl butyral, polyvinyl acetal, polystyrene, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, acrylic resin, phenolic resin, polyamide, polysulfone, polyvinyl butyral, polyvinyl alcohol, Polyvinyl acetate, polyester, polycarbonate, cellulose resin, etc. can be used.

In the electrophotographic photoreceptor of the present invention, the dye can be contained in the binder in an amorphous state, and the dye can also be contained in the form of particles. The organic solvent used when containing in an amorphous state varies depending on the binder used and the type of organic photoconductive substance mentioned above, but generally dichloromethane, chloroform, vertical tetrachloride, 1. l
-dichloroethane, 1,2-dichloroethane, Ll, 2
-) IJ Dichloroethane Halogenated hydrocarbons such as chlorobenzene, furomobenzene, and 1,2-dichlorobenzene are preferred. In addition, when it is contained in the binder in the form of particles, organic solvents that dissolve the binder and the hydrazone compound, such as alcohols such as methanol, ethanol, and isopropanol, and keto/fs1N, N −
Amides such as dimethylformamide and N,N-dimethylacetamide, sulfokinds such as dimethyl sulfoxide, ethers such as detrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, or benzene, Aromatics such as toluene, phosphorus, ligroin, and the like can be used.

The composition containing the P-171J dye of the present invention can be coated using coating methods such as dip coating, spray coating, spinner coating, bead coating, Mayer-Par coating, blade coating, roller coating, and curtain coating. It can also be used for coating. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying can be carried out at a temperature of 30° C. to 200° C. for a time ranging from 5 minutes to 2 hours, either stationary or under ventilation. The dry thickness of the coating layer formed by coating is suitably 10 microns to 100 microns, preferably 20 microns to 60 microns.

In another embodiment of the invention, eutectic complexes of the aforementioned pyridium dyes and polymers containing alkylizofodiaryleph moieties can be used as photoconductive materials. The method for forming this eutectic complex is described in U.S. Pat. No. 3,684,502.
No. 87757175, etc. Specifically, an organic solvent that dissolves both a pyrylium dye and a polymer having a repeating unit of alkylidene diarylene (for example, dichloromethane, chloroform, 1 salt (tlE element, 1. l -dichloroethane, 1
．． 2-) Conditions for forming a eutectic complex by bathing in chloroethane, 1,1゜2-trichloroethane, chlorobenzene, promobe/zene, l,2-dichloroenzene (Ef) halogenated hydrocarbons) Eutectic by adding a non-polar liquid (e.g. hydrocarbons such as hexa/, octa/, deca/, dodecane, Toluev% 2,2.4-)IJ methylpentane, ligroin, etc. after reacting under It depends on obtaining the precipitate.

Polymers having repeating units of alkylyzo/)arylene moieties that form eutectic complexes with these pyrylium dyes are
It is as described in F.

In a preferred embodiment of the present invention, in an electrophotographic photoreceptor RC in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer, the charge generation substance is added to the charge generation substance according to the general formula (11) or the above-mentioned pyrylium dye. A eutectic structure can be used.The charge generation layer is
In order to obtain a sufficient absorption interval, a thin film layer, e.g.
Preferably, the thin film layer has a thickness of 0.01 micron to 1 micron.

This means that most of the amount of incident I7 light is absorbed by the electrogenic layer, producing many llIC charge carriers, and that the generated charge carriers are recombined or trapped (trapped).
? This is due to the need to inject into the charge transport layer without deactivation.

The charge generation layer can be formed by dispersing the above-mentioned PIIJIJium dye or eutectic complex in a suitable binder and coating it on the substrate 1, and forming a vapor deposited film using a lid made of vacuum vapor deposition. can be obtained by Binders that can be used to form the peel generation layer by Coating 1 can be selected from a wide variety of 48-carbon resins, including organic photoconductive polymers such as poly(N-vinylcarbazole), poly(vinyl anthra7), and poly(vinylpyrene). You can choose from. Preferably polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.)
, polycarbonate, polyester, phenoxy resin,
Polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose Al
Examples include insulating resins such as lubricant, urethane resin, epoxy resin, casei resin, polyvinyl alcohol, and polyvinylpyrrolidone. The resin contained in Kosei 11- is suitably 80][IX to F1, preferably 40% by weight or less.

The solvent for dissolving these resins varies depending on the type of resin, and is preferably selected from those that do not affect the underlying charge transport 1 or the undercoat layer. Examples of organic solvents include alcohols such as methanol, ethanol, and isopropanol, ketones such as acetone, methyl ethyl ketone, and chlorohexanone, and alcohols such as N,N-dimethylformamide and N,N-dimethylacetamide. sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, dichloroethylene, dichloroethylene, aliphatic halogenated hydrocarbons such as benozene,
Toluene, quinolene, ligroin, mo/l lobenzene, cyclobenzene natonaromatics, etc. can be used.

Coating methods include dip coating, spray coating, spinner coating, bead coating,
This can be carried out using a coating method such as a Mayer coating method, a blade coating method, a roller coating method, or a curtain coating method. For drying, it is preferable to dry to the touch at a constant temperature and then heat dry. Heat drying at a temperature of 30°C to 200°C for 5 minutes to 2
It can be carried out stationary or on a blower for a range of hours.

The charge transport layer is electrically superior to the charge generation layer described above, and is capable of receiving and receiving charge carriers injected from the charge generation layer in the presence of a single field and transporting these charge carriers to the surface. It has a function. At this time, this charge transport layer may be laminated on or under the charge generation layer. However, it is desirable that the charge transport layer is laminated on the charge generation layer.

Substance that transports charge carriers in the charge transport layer (hereinafter referred to as F
1) #-i, the above-mentioned charge generation 1
Preferably, it is substantially insensitive to the wavelength range of electromagnetic waves to which it is sensitive. The term "magnetic wave" as used herein includes a broad definition of "light ray" that includes r-wave + X-rays, ultraviolet light + ciT visual light -9 near-infrared rays, infrared rays, far-infrared rays, and the like. The photosensitive wavelength range of the charge transport layer is different from that of the charge generation layer -gk
Or when they overlap, the charge carriers generated by introspection trap each other, resulting in a decrease in sensitivity.

As the charge transport substance, the above-mentioned low molecular weight organic photoconductive substances and bulk organic photoconductive substances can be used. In addition to these organic charge transport materials, inorganic materials such as K, selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can also be used.

Further, these charge transport materials can be used alone or in combination of two or more kinds.

When the charge transport material does not have film-forming properties, a film can be formed by selecting an appropriate binder. mW that can be used as a binder includes, for example, acrylic resin, polyarylate, polyester, polycarbonate,
Polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone,
Examples include insulating resins such as polyacrylamide, polyamide, #JI rubber, and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthramono, and polyvinylpyrene.

Since charge@transmission1 shield has a limit in its ability to transport acidic carriers, it is not possible to make the film thicker than necessary. Typically it is 5 microns to 30 microns, with a preferred range of 8 microns to 20 microns. When forming the charge transport layer by coating, an appropriate coating method as described above can be used.

Furthermore, the bicarbonate dye of the present invention is provided on a substrate that serves as a conductive layer. As a body with a conductive layer,
I-J: 1 The substrate itself is conductive, such as aluminum, aluminum alloy, copper, lead, stainless steel,
Vanadium, molybdenum, chromium, titanium, nickel, indium, gold, platinum, etc. can be used, and in addition, aluminum, aluminum alloys, indium oxide, tin oxide, indium oxide-tin oxide alloys, etc. can be used by vacuum evaporation. Plastics with coated layers (e.g. polyethylene, polypropylene, polyvinyl chloride,
Polyethylene terephthalate, acrylic resin, polyethylene terephthalate, etc.), conductive particles (for example, carpon-like, silver particles, etc.) are coated on plastic with a suitable binder, and conductive particles are coated on the plastic. Plastic or paper impregnated with a nine-substrate or a four-electrode polymer can be used.

A subbing layer having a barrier function and an adhesive function can also be provided between the conductive layer and the photosensitive layer. The subbing layer is made of casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6,
Nylon 66° Nylon 610. The film thickness of the OF4 film, which can be formed from copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc., is suitably 7 to 5 microns, preferably 3 microns to #io, s microns.

The biryllium dye of the present invention can be applied to a photoconductor used in an electrophotographic printer or an electrophotographic plate-making system using a process using a laser as a light source.
can be used.

According to the present invention, compared to conventional laser photoreceptors,
Significantly high sensitivity can be achieved in a wavelength range of Qnm or more.

Hereinafter, the present invention will be explained with reference to Examples.

Example 1 Ammonia aqueous solution of casein (casein/11.2 g, 28N ammonia water 1
g1 water 222d) is applied by dip coating method, dried and applied i11. Form a subbing layer of og/m'.

Next, a coating liquid having the composition F is prepared and applied.

The solution was applied by dipping so that the coating rate of dry bond was 10g/m''.

Coating liquid l-phenyl-3-(P-diethylaminostyryl)-
5-(p-diethylaminophenyl)pyrazoline
5f Poly-4,4'-dioxydiphenyl-2,2'-propane carbonate (molecular weight 30,000) 5f Thiobi-171Jum dye of the above example (% f4) 0.2f 1.1-dichloroethane 70 - Produced like this The electrophotographic photoreceptor made with 200.65X (relative 111 degrees)! After 11gl1, Kawaguchi Heavy Industries Seiden Copying Paper Testing Equipment Mo
Q5[ by static method using del 5P-428
After corona charging (V.) with V and holding for 10 seconds in a dark place, the potential retention rate (Vk-X) and sensitivity (E% microjoule/cd) tm were determined. At this time, the light source was a gallium arsenide semiconductor laser (oscillation wavelength: 830 nm).
sm) was used. These results are shown in Table 1.

Table 1 Vo: -510 Volts Vk: 86N E% -06 micro unit/1 Example 2 The coating liquid of the following composition was used in place of the 9 coating liquid used in Example 1. After making a photoreceptor in exactly the same manner as 1, the characteristics were measured. The results are shown in Table 2.

Coating liquid Holi [ethylenenocricol-CO-bis(hydroxy/ethoxy/phenyl) propantilephthalate)] 2.5f
P-2 Ethylaminobenzaldehyde-N,N-diphenylhydrazoy 1. Of the above examples,
16+41 thiovinium dye 0.2f dichloromethane 40m Table 2 VO: -530 Volts Vk: 84% E% 204 microjoules/cII Example 3 In place of the coating liquid used in Example 1, A photoreceptor was prepared in exactly the same manner as in Example 1, except for nine points, using a coating liquid having the composition described above, and then its characteristics were measured. The results are shown in Table 3.

Coating liquid Poly-N-vinylcarbazole 5v (molecules 130000) Polyester (manufactured by DuPont: Polyester Adhesive 49000: solid content 2ON) 3f Thiobi IJ IJum dye of the above-mentioned screen (4) 0.2 t
Monochlorobenzene 6〇-Table 3 Vo: -410 volts Vk near 6% g%: fi3 microjoules/j Example 4 In place of the diluter tLV used in Example 1, a coating liquid with the following composition was used. Other than that, a photoreceptor was prepared in exactly the same manner as in Example 1, and then its characteristics were measured. This binding is shown in Table 4.

Triphenylamine 7 3f polystyrene 3 is the thiopyrylium of the above-mentioned illustrative noodles (4)! 1GI0.2r Monochlorpe/Zen
50-Table 4 Vo: -460 Volts Vk: 83N EI: 1.4 Microgel/-Act) II 5
~12 In place of the thiopyrylium dye in the coating liquid used when creating the photoreceptor of Example 2, BiIJ I shown in Table 5 was used.
A coating solution was prepared in the same manner as in Example N2, except that Jum dye was used, and then a photoreceptor was produced. The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. These results are shown in Table i15.

ig5 table example pyrylium dye ■. Vk
B% (Volt) (%) (Microzi 1-1) 5
Mu (3) -500800,76m (
7) -510820,57716(10)
520 81 0.88
, &(12) −480821,594
(17) -500840,910, &(21'
) -510821,0114(23)
-460801,8124(27) -450
812,3 Examples 13 to 15 Example 4 was performed except that the pyrylium dye shown in Table 1jI6 was used instead of the pyrylium dye in the coating solution used when the photoconductor of Example 4 was prepared. Coating solution v4 was prepared in the same manner as above, and then a photoreceptor was prepared. 7 for each photoreceptor
7 Tometry was performed in the same manner as in Example 1. These results tl-6th! ! ! Shown below.

Chapter 6 Table 13 Demon (3') -440802,0
14A(7) -450821,515-(1
7) -470801,711! Example 16 Case 7 in aqueous ammonia 11k (casei 711.2 F, 28% aqueous ammonia 1 f) on aluminum/sheet.

222 mg of water) It was coated with MyEver and dried so that the film thickness after drying was 1.0 microns.

Next, 1 t of ThiopiIJ lithium salt of the above example t(4)
and Polymer Taki 4 (poly(4,4-isopropylide/diphenylenecarbo*-)) lof were added to 420-dichloromethane and stirred for 4 hours to dissolve and form a eutectic complex composition.

This eutectic monolithic composition was applied onto the previously formed casein layer using an extrusion hopper coating machine so that the film thickness after drying was 0.8 μm, and after drying, toluene was added to form an aggregate. Charge generation +1 t- formed by eutectic complex coating.

Next, P-diethylaminobenzaldehyde-N-α
-Naphthyl-N-phenylhydrazone 5t and polymethyl methacrylate resin (number average molecular weight 100,000)
5f was dissolved in benzene 70-, and this was applied onto the charge generation layer using Mayer Parr so that the film thickness after drying would be 12 microns, and dried to form a charge transport layer.

Cent/tometry of this photoreceptor was performed in the same manner as in Example 1. These results are shown in Table 7.

Table 7 Vo: -570 volts vk: 91% B34: 0.3 microjoules/cd Example 17 In place of the thiopyrylium salt of At41 used in Example 16, the thiopyrylium salt of A(7) was used. A photoreceptor was prepared in exactly the same manner as in Example 16, and then sensitometry was performed in the same manner as in Example 1. These results are shown in Table 8.

Table 8 Vo: -550 Gelt Vk: 92% gt, ): o, s microjoule/je, J-J

Claims (1)

[Claims] An organic photoconductor represented by the above general formula (1). General formula (1) (In the formula, the laminated -X represents a sulfur atom, an oxygen atom, or a selenium atom. Hato and Peng represent a substituted or unsubstituted aryl group. R+s represents a substituted or unsubstituted aryl group. Represents an aryl group or a substituted or unsubstituted heterocyclic group.Kan, he, 鵵, and re represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group.n is l or Vi2.However,
When n is 2, ^ may be the same or different, and 攬 may be the same or different (-,). A Fi indicates a pure ion. )