JPS6267554A - Photosensitive composition - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body which is applied to various photoconductors and has high sensitivity and a stable potential characteristic in repetitive use by incorporating at least one of a specific disazo compd. or specific tetra kisazo compd. into said body. CONSTITUTION:This photosensitive body contains at least one kind of the disazo compd. expressed by formula [1] or the tetra kisazo compd. expressed by formula [2]. In the formula, Cp denotes a coupler residue, Ar denotes a devalent arom. carbon ring group, divalent arom. heterocyclic group or the substituent thereof, R<1> denotes an alkyl group, aralkyl group, aryl group or the substituent thereof, R<2> denotes a hydrogen atom, electron attractive group or substd. or unsubstd. alkyl group, R<3> denotes a hydrogen atom or electron attractive group, R<4> denotes a hydrogen group, halogen group, alkyl group, alkoxy group, aryl group, aryloxy group or the substituent thereof. X is the atom group expressed by formula (II). The optical information recording medium having a long shelf life, high sensitivity and substantial S/N ratio is thus obtd.

Description

DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a photoconductive composition characterized by containing a novel disazo compound or tetrakisazo compound. It also relates to a heat mode optical information recording medium in which state changes are caused by a high-density energy beam (secondary recording and reproduction is performed).

``Prior art'' Electrophotography has already been published by Carlson in US Patent No. 2 Kotoku 6.
As disclosed in No. 7, a photoconductive material consisting of a support coated with an insulating substance in the dark whose electrical resistance changes depending on the amount of radiation received during image exposure is used. This photoconductive material is generally given a uniform surface charge in the dark after dark adaptation for a suitable period of time.The material is then given a uniform surface charge in the dark after dark adaptation for a suitable period of time. The surface charge or electrostatic latent image thus left on the surface of the photoconductive material layer (electrophotographic photosensitive layer) is then imaged by a pattern of radiation which has the effect of reducing the surface charge according to the surface charge. is contacted with a suitable electrolytic indicator material, ie, toner, to form a visible image.

The toner is contained in an insulating liquid or in a dry carrier, and in either case, it can be deposited on the surface of the electrophotographic photosensitive layer depending on the charge pattern.

The deposited display material can be fixed by known means such as heat, pressure, and solvent vapor. Also, the electrostatic latent image is the second
The electrostatic latent image can be similarly transferred to a second support (e.g. paper, film, etc.).
It is also possible to develop the image there. Electrophotography is one of the image forming methods that forms images in this manner.

The basic characteristics required of an electrophotographic photoreceptor in such an electrophotographic method are (1) an appropriate potential in a dark place (
(2) less charge dissipates in the dark; and (3) scales that quickly dissipate charge when irradiated with light.

Conventionally, selenium, cadmium sulfide, zinc oxide, and the like have been used as photoconductive materials for electrophotographic photoreceptors.

However, while these inorganic substances have many advantages, they also have various disadvantages.

For example, selenium, which is currently widely used, is
Although the condition (3) is fully satisfied, the manufacturing conditions are difficult, the manufacturing cost is high, there is no single flexible sheet, it is difficult to process into a belt shape, and it is sensitive to heat and mechanical shock. It also has some drawbacks, such as the need for careful handling. Cadmium sulfide and zinc oxide are used as electrophotographic photoreceptors by dispersing them in resin as a binder, but
Due to mechanical defects such as hardness, tensile strength, and abrasion resistance, it cannot be used repeatedly as it is.

In recent years, in order to eliminate the drawbacks of these inorganic materials, electrophotographic photoreceptors using various organic materials have been proposed and put into practical use (
Some are served twice. For example, an electrophotographic photoreceptor (US Pat. No. 3,4t
tg, r32), poly-N-vinylcarbazole sensitized with pyrylium salt dye (Tokuko Shogu♂-2!Otsu!
♂), electrophotographic photoreceptors whose main components are organic pigments (JP-A-7-32JT, t3), electrophotographic photoreceptors whose main components are eutectic complexes consisting of dyes and resins (JP-A-4T7-) /θ
7/ri etc.

Electrophotographic photoreceptors using such organic materials can be produced by appropriately selecting a binder (= coating), so it is possible to provide an extremely productive and inexpensive photoreceptor, and improve mechanical properties and flexibility. In addition, the selection of dyes and organic pigments (= therefore, the sensitivity wavelength can be controlled freely). However, on the other hand, the photosensitivity is low and it is not suitable for repeated use, so it does not fully meet the requirements for electrophotographic photoreceptors. There wasn't.

The present inventors have conducted intensive research to solve the drawbacks of the conventional electrophotographic photoreceptors, and as a result, an electrophotographic photoreceptor using a photoconductive composition containing a novel disazo compound and a tetrakisazo compound has been developed. The present invention was achieved by discovering that it has sufficient sensitivity and durability for practical use.

On the other hand, conventional recording methods in which information recording media (i.e., irradiated with high energy density beams to change physical property constants such as transmittance, reflectance, and refractive index) produce images with extremely high resolution and contrast. It is suitable for recording computer output and transmitted time-series signals because it has the following characteristics: it is possible to add information later, and it can record at the same time as it is exposed. COM (Computer Output Micro) has the advantages of
It is applied to micro facsimiles, printing plates, optical discs, etc.

For example, recording media used in optical disk technology can store high-density information using approximately 72 or so small optically detectable pits in the form of spiral or circular tracks. This kind of disk (writes two information (= is,
The surface of the laser sensitive layer is scanned with two focused laser beams, and only the surface irradiated with this laser beam forms pits.
The pits are formed in the form of spirals or circular tracks.

In the heat mode recording method, the laser sensitive layer absorbs thermal energy when irradiated with a laser beam, and forms small pits at the locations by evaporation or melting.

The information recorded on the optical disc in this way is detected by scanning the laser along the track (-) and reading the optical changes in the areas where pits are formed and the areas where pits are not formed.

Information recording media that can perform heat mode recording have conventionally been formed using thin films of metals and/or metal oxides, semimetallic dielectrics, etc. on transparent supports such as plastics, or those containing self-oxidizing binders and dyes. Recording media have been used in which a thin film is provided as a recording layer and a protective layer is provided on the thin film.

However, conventional thin films mainly composed of inorganic substances have a high reflectance for laser light (2), so the efficiency of laser use decreases, and therefore (= high sensitivity characteristics cannot be obtained, or There were problems such as a significant increase in the output of the laser light.

On the other hand, organic compounds generally have problems such as their absorption characteristics becoming unstable as the wavelength range increases and being easily decomposed by a slight increase in temperature.

Therefore, the "direct read after write" capability CDRAW(di
Rect read and write)] A recording medium (2) that has a high absorption efficiency compared to the required laser beam (2), sufficient focus control when reading records (2) that has a reflectance that allows for recording images, etc. A recording medium containing an organic thin film that has to satisfy various characteristics such as stability and the like has not necessarily been developed that is fully satisfactory from the point of view of practicality.

The present inventors have achieved the present invention (2) as a result of intensive research in order to eliminate the above-mentioned drawbacks.

"Problems to be Solved by the Invention" An object of the present invention is to provide a photoconductive composition that can be applied to various photoconductors. Still another object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity and stable potential characteristics during repeated use.

Another object of the present invention is to provide an optical information recording medium that has high storage stability, high sensitivity, and a sufficient S/N ratio.

"Means for Solving the Problem" The present invention is characterized by containing at least one kind of a disazo compound represented by the following general formula [1] or a tetrakisazo compound represented by the following general formula [k]. It is a photosensitive composition.

/+I r+X1+
7 ShiJ general formula [1
] and [2] (= in which Cp represents a coupler residue. Ar represents a covalent aromatic carbocyclic group, a -valent aromatic heterocyclic group, or a substituent thereof.

R1 represents an alkyl group, an aralkyl group, an aryl group or a substituted product thereof.

R2 represents a hydrogen atom, an electron-withdrawing group, or a substituted or unsubstituted alkyl group.

R3 represents a hydrogen atom or an electron-withdrawing group.

R4 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or a substituted product thereof.

X is an atomic group represented by the following general formula (n).

R (However, R5 and R6 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or a substituted product thereof, and R5 and R6 are bonded to each other to form a fused polycyclic aromatic ring. may be formed.

l and n represent 0 or an integer of /~, and m represents θ or /. ) q represents O or /, and if q is Q, -N=N-C
p is directly bonded to any position of Ar.

The disazo compound and tetrakisazo compound of the present invention will be explained in detail.

In general formulas [1] and [here:2], Cp represents a coupler residue, and is preferably selected from the coupler components shown below.

Rt R' 2 is condensed with the ring term in the above formula in which the hydroxy group and Y are bonded to form an aromatic ring or a heterocycle (these rings may be substituted or unsubstituted). represents an atomic group necessary for , Y is a hydrogen atom, -CONRloRII
, -COORIOl-CONHNRloRII, -CO
NHN=CI(-RIO or R7 represents an alkyl group, a phenyl group, or a substituent thereof; R8 is a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a substituted or unsubstituted represents a substituted amine group, R9 represents an alkyl group, an aromatic ring group, a heteroaromatic ring group, or a substitute thereof; RIO and R11 represent a hydrogen atom, an alkyl group, an aromatic ring group, a heteroaromatic ring group; or a substitute thereof.

When R1 is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, intyl group, hexyl group, octyl group, nonyl group, dodecyl group, isopropyl group, isobutyl group, There are methyl group, dermeterbentyl group, 5ec-butyl group, and tert-butyl group. When R1 is an alkyl group having a substituent, specific examples of the substituent include chlorine, bromine, fluorine as a halogen atom, methoxy group, ethoxy group, propoxy group, butoxy group, inthyloxy group, and aryloxy group as an alkoxy group. As a group, phenoxy group, 〇-tolyloxy group, m-tolyloxy group, p-tolyloxy group, /-naphthyloxy group, corneraphtheroxy group, dialkylamino group as dimethylamino group, diethylamino group, dipropylamino group, N-methyl -N-ditylamino group, N
-ethyl-N-propylamino group, N-methyl-N-propylamino group, diphenylamino group as diarylamino group, methylthio group, ethylthio group, propylthio group as alkylthio group, bi-lysine group as N-containing heterocyclyl group , /-pi includes a radionyl group, a morpholino group, and a /-pyrrolidyl group. An example of an alkyl group having a substituent is an alkyl group in which any one of these substituents is bonded to at least/any carbon atom of the above-mentioned alkyl group.

When R1 is an unsubstituted aralkyl group, specific examples thereof include benzyl group, phenethyl group, /-naphthylmethyl group, λ
-Naphthylmethyl group, /-anthrylmethyl group, and benzhydryl group. In the case of an aralkyl group having a substituent, specific examples of the substituent include the same groups as the substituents of the alkyl group having a substituent described above, and any of these substituents can be any carbon atom of the aralkyl group described above. is an example of an aralkyl group having a substituent.

When R1 is an unsubstituted aryl group, specific examples thereof include phenyl group, /-naphthyl group, λ-naphthyl group, anthryl group, pyrenyl group, acenaphthynyl group, and fluorenyl group. In the case of an aryl group having a substituent, specific examples of the substituent include the same substituents as the alkyl group having a substituent mentioned above, and in addition, as an alkyl group, a methyl group,
Ethyl group, propyl group, butyl group, pentyl group, isopropyl group, isobutyl group, in has a methyl group, and an aryl group in which at least one of these substituents is bonded to the carbon atom of the above-mentioned aryl group This is an example of an aryl group having a substituent.

In the case of R2 and R3 electron-trapping groups, specific examples include a nitro group, a cyano group, and a halogen atom (eg, a chlorine atom, a bromine atom, a fluorine atom, etc.).

When R2 and R4 are substituted or unsubstituted alkyl groups, specific examples include the same groups as the above-mentioned examples of substituted or unsubstituted alkyl groups for R1.

When R4 is a halogen atom, specific examples include a fluorine atom, a chlorine atom, a bromine atom, and the like. R4
When is an unsubstituted alkoxy group, aryl group, or aryloxy group, specific examples thereof include alkoxy groups such as methoxy group, ethoxy group, and propoxy group, aryl groups such as phenyl group and naphthyl group, phenoxy group, and naphthoxy group. The aryloxy group can be mentioned. When R4 is an alkoxy group, aryl group, or aryloxy group having a substituent, the substituent can be the same as the substituent described above when R1 is a substituted alkyl group.

Specific examples of R5 and R6 include the same groups as the above-mentioned specific examples of R4. When R5 and Ra combine with each other to form a condensed polycyclic aromatic ring, specific examples of the condensed polycyclic aromatic ring include a naphthalene ring, an anthracene ring, and the like.

R7 is an alkyl group, preferably an alkyl group having 1 to 2 carbon atoms or a phenyl group.

When R7 is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, hunthyl group, hexyl group, isopropyl group, isobutyl group, isoamyl group, -inhexyl group, and neo is a methyl group. ,tert
-Butyl group, etc. can be mentioned.

When R7 is a substituted alkyl group, the substituent is a hydroxy group, an alkoxy group having /~/2 carbon atoms, a cyan group, an amine group, an alkylamino group having /~/2 carbon atoms, or a carbon number /~/2.
/2 alkyl group, dialkylamino group, halogen atom, number of carbon atoms ~/! aryl groups, etc.

Other examples include hydroxyalkyl groups (e.g., hydroxymethyl group, λ-hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, etc.), alkoxyalkyl groups (e.g., methoxymethyl group, 2-methoxyethyl group, 3-hydroxypropyl group, etc.), -methoxypropyl group, ethoxymethyl group, coethoxyethyl group, etc.), cyanoalkyl group (
For example, cyanmethyl group, cocyanoether group, etc.), aminoalkyl group (e.g., aminomethyl group, co-aminoethyl group, 3-aminopropyl group, etc.), (alkylamino)alkyl group (e.g., (methylamine)methyl group,
λ-(methylamine)ethyl group, (ethylamino)methyl group, etc.), (dialkylamino)alkyl group (e.g., (dimethylamino)methyl group, λ-(dimethylamino)ethyl group, etc.), halogenoalkyl group (e.g. , fluoromethyl group, chloromethyl group, bromomethyl group, etc.), and aralkyl groups (eg, benzyl group, phenethyl group, etc.).

When R7 is a substituted phenyl group, examples of the substituent include a hydroxy group, an alkoxy group having 7 to 7.2 carbon atoms, a cyano group, an amino group, an alkylamino group having 7 to 2 carbon atoms, and a 7-carbon group having 7 to 2 carbon atoms.
a dialkylamino group having co alkyl groups of ~/2;
Examples include halogen atoms, alkyl groups having 7 to 7 carbon atoms, and nitro groups. Examples thereof include hydroxyphenyl group, alkoxyphenyl group (e.g., methoxyphenyl group, ethoxyphenyl group, etc.), cyanophenyl group, aminophenyl group, (alkylamine)phenyl group (e.g., (methylamine)phenyl group, (ethylamino) phenyl group, etc.), (dialkylamine) phenyl group (e.g. dimethylamino) phenyl group, etc.), halogenophenyl group (e.g. Eva, fluorophenyl group, chlorophenyl & iromophenyl group, etc.), alkylphenyl group (e.g. eva, tolyl group, eterphenyl group, cumenyl group, xylyl group, mesityl group, etc.), nitrophenyl group, and these substituents (2 or 3 of each other (which may be the same or different))
(The position of the substituent or the mutual positional relationship between the substituents is arbitrary).

R8 is a hydrogen atom, a lower alkyl group having a carbon number of /~B, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group having an alkoxy group having a carbon number of /~/2, an aryloxy group having an aryloxy group having a carbon number of 6 to 2θ A carzenyl group and a substituted or unsubstituted amine group are preferred.

When R8 is a substituted amine group, seven specific examples include methylamine group, ethylamino group, propylamine group, phenylamino group, tolylamino group, benzylamino group, phenethylamino group, dimethylamino group, diethylamino group,
Examples include diphenylamino group.

When R8 is a lower alkyl group, specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, and the like.

When R8 is an alkoxycarbonyl group, specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, an impropoxycarbonyl group, a benzyloxycarbonyl group, and the like.

When R8 is an aryloxycarbonyl group, specific examples of () include a phenoxycarbonyl group, a doloxycarbonyl group, and the like.

R9 and R11 are alkyl groups with carbon number/~λθ, aromatic ring groups such as phenyl groups and naphthyl groups, oxygen atoms, nitrogen atoms, and sulfur atoms such as dibenzofuranyl groups, carbazolyl groups, and benzocarbazolyl groups. Heteroaromatic ring groups including these or substituted products thereof are preferred.

When R9 or R11 is a substituted or unsubstituted alkyl group, examples thereof include the same groups as the above-mentioned examples of the substituted or unsubstituted alkyl group for R7.

When R9 or R11 is a substituted aromatic group such as a substituted phenyl group, a substituted naphthyl group, a substituted heteroaromatic group containing a heteroatom such as a substituted dibenzofuranyl group or a substituted carbazolyl group, examples of the substituent include a hydroxy group, Cyano group, nitro group, norogen atom (e.g., fluorine atom, chlorine atom,
bromine atom, etc.), an alkyl group having /~/2 carbon atoms (e.g.
(methyl group, ethyl group, propyl group, isopropyl group, etc.)
, a haloalkyl group having /~/2 carbon atoms (e.g., chloromethyl group, trifluoromethyl group, trichloroether group, etc.), an alkoxy group having /~/2 carbon atoms (e.g., methoxy group, ethoxy group, propoxy group, butoxy group) group, pentyloxy group, isopropoquine group, imbutoxy group, isoamyloxy group, tert-butoxy group, neo-interoxy group, etc.), amine group, alkylamino group having /~/2 carbon atoms (e.g. methylamino group, ethyl amino group, propylamine group, etc.), dialkylamino group having /~/2 carbon atoms (e.g. dimethylamino group, diethylamino group, N
-methyl-N-ethylamino group, etc.), an arylamino group having 6 to 2 carbon atoms (for example, a phenylamino group, a tolylamino group, etc.), and a carbon number of 6 to 2 carbon atoms. A diarylamino group (for example, diphenylamino group, etc.) having two aryl groups, a carboxyl group, an alkali metal carboxylad group (an example of an alkali metal (cation), Na, K.

, ■Ll, etc.), alkali metal sulfonate groups (alkali
e Examples of glue metals (cations), Na, K XLl, etc.), alkylcarbonyl groups (e.g., acetyl groups, propionyl groups, benzylcarbonyl groups, etc.), arylcarbonyl groups having an aryl group with a carbon number of Examples include benzoyl group, toluoyl group, alkylthio group having 7 to 2 carbon atoms (e.g., methylthio group, ethylthio group, etc.), or arylthio group having 7 to 2 carbon atoms (e.g., phenylthio group, tolylthio group, etc.). The number of substituents is 7 to 3, and when multiple substituents are bonded, they may be the same or different from each other, and may be in any combination. The bonding position is arbitrary.

RIO includes hydrogen atoms, alkyl groups having up to 20 carbon atoms, aromatic ring groups such as phenyl groups and naphthyl groups, oxygen atoms such as dibenzofuranyl groups, carbazolyl groups, and benzocarbazolyl groups, nitrogen atoms, and sulfur. There are heteroaromatic ring groups containing atoms or substituents thereof.

When RIO is a substituted or unsubstituted alkyl group, aromatic substituent, or heteroaromatic ring group, the same groups as the above-mentioned R9 and all are mentioned, and Y is ~C0NRIO
RII, -CONHNR10R11 or together with the attached nitrogen or carbon atom can form a ring. Specific examples include a pyrrolidine ring, py is a lysine ring,
The morpholine ring, cyclopentane ring, and cyclohexane ring can be substituted at any position from the 3-position to the r-position of the phthalene ring, but it is preferable to substitute at the .

Ar represents a covalent aromatic carbocyclic group, a divalent aromatic heterocyclic group, or a substituent thereof. Specific examples thereof include a covalent aromatic carbocyclic group, a covalent aromatic carbocyclic group, and a substituted product thereof as shown in the following structure.

Examples of the substituent include the same groups as the above-mentioned substituents for R9 and RIJ2.

Further 1: Specific examples of cp include the coupler residues shown in Table 1.

Specific examples of the disazo compound represented by the general formula [1] are shown in Table 2 (when q=O) and Table 3 (when q=/).

n)\
The electrophotographic photoreceptor of the present invention comprises a disazo compound or a tetrakisazo compound represented by the general formula [1] or [ko].
It has an electrophotographic photosensitive layer containing one or more species. Various types of electrophotographic photoreceptors are known, and the electrophotographic photoreceptor of the present invention may be any type of photoreceptor, but it usually has an electrophotographic photoreceptor structure of the type exemplified below. .

(a) An electrophotographic photosensitive layer comprising a disazo compound or a tetrakisazo compound dispersed in a binder or a charge carrier transport medium is provided on a conductive support.

(b) A charge carrier generation layer containing a disazo compound or a tetrakisazo compound as a main component is provided on a conductive support, and a charge carrier transporting medium layer is provided thereon.

The disazo compound or tetrakisazo compound of the present invention acts as a photoconductive substance, and when it absorbs light, it generates charge carriers with extremely low efficiency, and the generated charge carriers can also be transported using the disazo compound or tetrakisazo compound as a medium. However, it is more effective to use a charge carrier transporting compound as a medium.

To prepare an electrophotographic photoreceptor of type (a), fine particles of a disazo compound or a tetrakisazo compound are dispersed in a binder solution or a solution in which a charge carrier transport compound and a binder are dissolved, and this is coated on a conductive support. Just dry it. The thickness of the electrophotographic photosensitive layer at this time is 3~
30μ, preferably 3 to θμ.

In order to produce an electrophotographic photoreceptor of type (b), a disazo compound or a tetrakis azo compound is vacuum-deposited on a conductive support, or a disazo compound or a tetrakis azo compound is dissolved in a solvent such as an amine, and then applied. Fine particles of an azo compound are dispersed in a suitable solvent or, if necessary, a solvent in which a binder is dissolved, coated and dried, and then a solution containing a dicharge carrier transporting compound and a binder is coated and dried. At this time, the thickness of the disazo compound or tetrakisazo compound layer serving as the charge carrier generation layer is preferably not more than daμ, preferably not more than λμ, and the thickness of the charge carrier transport medium layer is 3 to 30μ, preferably !~-〇μ.
Good.

The disazo compound or tetrakisazo compound used in the photoreceptor of type (a) and [with] is Zeelmil,
Particle size is determined using a dispersing machine such as a sand mill or vibration mill. μ or less,
Preferably, it is used after being ground to a size smaller than microμ.

If the amount of the disazo compound or tetrakisazo compound used in the electrophotographic photoreceptor of type (a) is too small, the sensitivity will be poor, and if it is too large, the strength of the electrophotographic photosensitive layer will be weakened due to poor charging properties. However, the proportion of the disazo compound or tetrakisazo compound in the electrophotographic photosensitive layer is 0.01 to 2 times the weight of the binder, preferably 0.0! 〜/weight times is good, and the ratio of the charge carrier transport compound added as necessary is 0.1 to 0.1 to the binder.
The amount is preferably 2 times by weight, preferably 0.3 to 7.3 times by weight. Further, in the case of a charge carrier transport compound that can itself be used as a binder, the amount of the disazo compound or tetrakisazo compound added is 0.00% relative to the binder. Q nor θ
,! It is preferable to use twice the amount by weight.

In addition, when forming a disazo compound- or tetrakisazo compound-containing layer that becomes a charge carrier generation layer in an electrophotographic photoreceptor using a binder resin (type), the amount of the disazo compound or tetrakisazo compound used relative to the binder resin (two types) is o.
, i weight or more is preferable, and if it is less than that, sufficient photosensitivity cannot be obtained. The proportion of the charge carrier transport compound in the charge carrier transport medium is preferably 0.2 to 2 times, preferably 0.2 to 7.3 times the weight of the binder. When using polymeric charge carrier transport compounds which themselves can be used as binders, other binders can also be used without the need for other binders.

In addition, type (b) photoreceptor (second patent application Sho J-9-J)
3//3rd issue, special request! Tar/θ Tata θg issue, special request! Charge carrier transport compounds such as hydrazone compounds and oxime compounds can be added to the charge carrier generation layer as described in the specification.

When producing the electrophotographic photoreceptor of the present invention, additives such as a plasticizer or a sensitizer may be used together with the binder.

Examples of the conductive support used in the electrophotographic photoreceptor of the present invention include a metal plate made of aluminum, copper, or zinc, a plastic sheet made of polyester, or a plastic film (aluminum, indium oxide, 5N02
A material coated with a conductive material such as evaporated or dispersed thereon, or paper treated with a conductive treatment is used.

As the binder, it is preferable to use a film-forming polymer that is hydrophobic, has a high dielectric constant, and is electrically insulating. Examples of such high molecular weight polymers include, but are not limited to, the following.

Polycarbonate, polyester, polyester carbonate, methacrylic resin, acrylic resin.

polyvinyl chloride, polyvinylidene chloride, polystyrene,
Polyvinyl acetate, styrene-butadiene copolymer, vinylidene chloride-7crylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-
Maleic anhydride copolymer, silicone resin, silicone-alkyd resin, phenol-formaldehyde 41 fat,
Styrene-alkyd resin, poly-N-vinylcarbazole These binders can be used alone or in a mixture of two or more.

Plasticizers include biphenyl, chlorinated biphenyl, o-f-ruphenyl, p-terphenyl, cyphthyl phthalate, dimethyl glycol phthalate, dioctyl phthalate,
Triphenyl phosphate, methylnaphthalene, benzophenone,! m-paraffin, polypropylene, polystyrene,
Dilauryl teodiprobionate! , j-dinitrosalicylic acid, various fluorohydrocarbons, and the like.

In addition, silicone oil or the like may be added to improve the surface properties of the electrophotographic photoreceptor.

Sensitizers include chloranil, tetracyanoethylene,
Examples include methyl violet, rhodamine B1 cyanine dye, merocyanine dye, pyrylium dye, and thiapyrylium dye.

Compounds that transport charge carriers are generally classified into two types: compounds that transport electrons and compounds that transport holes, and both can be used in the electrophotographic photoreceptor of the present invention. Compounds that transport electrons include compounds having an electron-withdrawing group, such as +i2. t, 7-t+) Ni rotor fluorenone 5.21ri,! 12-tetranitro 9-fluorenone, terdicyanomethylene = 2,4t,
7-trinitrofluorenone, 9-dicyanomethyleneco.

4t,j,7-tetranitrofluorenone, tetranitrocarbazole chloranil, 2,3-dichloro-! , 4
-dicyanobenzoquinone, 2.4t, 7-dolinitro-9,10-phenanthrenequinone, tetrachlorophthalic anhydride, tetracyanoethylene, tetracyanoquinodimethane, and the like.

Compounds that transport holes include compounds having an electron donating group, such as polymers, (1) Tokko Sho J'
Polyvinylcarbazole and derivatives thereof described in Japanese Patent No. 1-10966, (2) Japanese Patent Publication No. 4t3-/167, Japanese Patent Publication No. 4t3-/ri/? Polyvinylpyrene, polyvinylanthracene, polyvinyl chloride described in λ publication
(¥'-dimethylaminophenyl)-! Vinyl polymers such as -7-enyl-oxazole, poly-1J-3-vinyl-N-2-fk carbazole, (3) Japanese Patent Publication No. 4t3-191
Polyacenaphthylene, polyindene, described in Publication No. 93,
Polymers such as copolymers of acenaphthylene and styrene, (4)% condensation resins such as pyrene-formaldehyde resins, 7'rompyrene-formaldehyde resins, and ethylcarbazole-formaldehyde resins described in Publication No. 74-/39110.

(5) Tokukai Akira! Otsu-90713 and Tokukai Sho! 6-/#
/! Various triphenylmethane polymers described in JO publication.

In addition, low-molecular compounds include (6) triazole derivatives described in U.S. Patent No. 3//2/97, etc.; (7) triazole derivatives described in U.S. Patent No. 3//94t4t7, etc. Oxadiazole derivatives, (8) Special Publication Show 3
Imidazole spinners described in Publication No. 7-16096, etc. (9) U.S. Patent No. 34134102, Kjr CoQ9
♂ri issue, same 3!4t Kodada issue, special public show 4t! -Evening!
No. Tokko Akira! /-10913, Tokukai Akira! /-ta j22
Issue 4, Tokukai Akira! ! -/θt6 to No. 7, Tokukai Akira! j-/
No. J-4913, Japanese Patent Publication No. Shoj Buichi 366! Specifications, publications, etc. 1: Polyarylalkane derivatives described, α1 U.S. Patent No. 3/10729, U.S. Patent No. 4t2
7F7 da No. 6, Tokukai Shojjr-Itθgoda No., Tokukai Sho!
j-1rO6Jr, Tokukai Showa Date 10Jr! No. 37,
Tokukai Shoj! -J'1Ort issue, Tokukai Sho! 4-100! /
No., JP-A No. 4-/♂/4-t/, No. 77-4-tj
Oke issue, Tokukai Akira! Goo//No. 2637, Tokukai Akira! J'-
Pyrazoline derivatives and zerazolone derivatives described in 74114tIs specification, gazette, etc.

αυ U.S. Patent No. 3t/! No. 4104, Tokuko Shoj/-
No. 1010j, Tokukai Sho! Dar♂34t3! No., Tokukai Akira!
Goo/10♂3 issue, Tokukai Akira! Da//Tata=! No. 416-37/2, Japanese Patent Publication Sho Guar No. 21336, patent publications, etc.
j2θλ, West German Patent (DAS) ///θjar,
U.S. Patent No. 3710703, U.S. Patent No. 3.24tO
J-97, US Patent No. 3tjrjJQ, US Patent No. 4t232103, US Patent No. 4t/7! Ri No. 37,
U.S. Patent No. 4tO/2376, JP-A-Shojj-/4t4
t2j-0, Tokukai Sho! Otsu-//9/32 issue, Tokuko Sho 3
#77, arylamine derivatives described in JP-A-74-224t37, publications, etc. (13 Amino-converted chalcone derivatives described in U.S. Pat. , α 荀 N,N-bicalbasil derivatives described in US Pat. styryl anthracene derivatives described in et.

α mark U.S. Patent No. 37/741≦λ, Unexamined Japanese Patent Publication No. 4! RI/4t3 (corresponding to U.S. Patent No. 4'/60917), JP-A-Shojj-j2θg-3, JP-A-Sho! ! -! −〇 Otogu issue, Tokukai Akira! ! --4tt7bu0% Tokukai Showa 3! -11
No. 4191, JP-A-Shoj7-//J! No. θ, JP-A-77-
/l/74t? No., Tokukai Akira! 2-104t/4tgt specification etc., hydrazone visiting conductor, 翰 U.S. Patent No. 794t1, U.S. Patent No. 4t0
4t7ri4t9, US Patent No. 412B! Wata Q, US Patent 4t Co23/Nu 6, US Patent 4t7! Tata♂9
No. 2, benzidine derivatives described in US Patent No. 4t3Qtoot, etc. ■ JP-A-Sho! ♂-/9θ9! No. 3, Tokukai Akira! Day 9rj
4tO, JP-A-79-97/9TR, JP-A-Sho! Tar/ri! Otsu! Examples include stilbene derivatives described in Publication No. 1 and the like.

In the present invention, the compound that transports charge carriers is (1
The present invention is not limited to the compounds listed in ) to (a), and all charge carrier transport compounds known so far can be used.

Two or more types of these charge transport materials may be used in combination depending on the case.

In addition, in the photoreceptor obtained as described above, an adhesive layer or a barrier layer can be provided between the conductive support and the photosensitive layer, if necessary. Materials used for these layers include, in addition to the high molecular weight polymer used for the binder, gelatin, casein, polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, and JP-A-Sho! Targ No. 2 Da No. 7, (=vinylidene chloride polymer latex described in JP-A-Sho! Ter//4tj4t4, styrene-butadiene polymer latex or aluminum oxide, etc., and the thickness of these layers is 7
It is preferably less than μm.

Although two electrophotographic photoreceptors of the present invention have been described in detail above, the electrophotographic photoreceptor of the present invention generally has characteristics such as high sensitivity and excellent durability.

The electrophotographic photoreceptor of the present invention can be widely applied in fields such as photoreceptors for printers using lasers and cathode ray tubes as light sources, as well as electrophotographic copying machines.

The photoconductive composition containing the disazo compound or tetrakisazo compound of the present invention can be used as a photoconductive layer in the image pickup tube of a video camera, or as a photoconductive layer on a one-dimensional or two-dimensional array of semiconductor circuits for performing known signal transfer or scanning. It can be used as a photoconductive layer of a solid-state imaging device having a light-receiving layer (photoconductive layer) provided over the entire surface. Also, in A, Ghosh et al.
, K.

Qhosh,'l'om peng,J,Appl,p
hys,,<t9(/,2),! 9F2 (/9';#
It can also be used as a photoconductive layer in solar cells as described in )).

The disazo compound or tetrakisazo compound of the present invention can also be used as photoconductive colored particles in a photoelectrophoresis system and colored particles in a dry or wet electrophotographic developer.

Further, the disazo compound or tetrakisazo compound of the present invention may be used in Japanese Patent Publication Nos. 37-77732 and 36-190.
No. 63, Tokukai Sho! ! −/≦/ko! θ No., JP-A-Shoj7-/
4t74j4, it is dispersed in an alkali-soluble resin solution such as a phenolic resin together with the above-mentioned charge carrier transporting compounds such as oxadiane derivatives and hydrazone derivatives, and is applied to a conductive support such as aluminum. J:-2 After coating and drying, image exposure, toner development, and etching with aqueous alkaline solution (2) A printing plate with high resolution, high durability, and high sensitivity can be obtained, and a printed circuit can also be created.

Next, an example of using the photosensitive composition of the present invention as an optical information recording medium will be described.

That is, the optical information recording medium of the present invention is constructed by forming an organic thin film containing at least the disazo compound or tetrakisazo compound of the present invention on a support,
The organic thin film can be formed using various methods such as vacuum evaporation coating of the above-mentioned compound.

When using the coating method, the organic solvents include alcohols (for example, methanol, ethanol, impropatol, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), amides (for example, N, N-dimethylformamide,
N,N-dimethylacetamide, etc.), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), ethers (e.g., tetrahydrofuran, dioxane, monoglyme, diglyme, etc.), halogenated hydrocarbons (e.g., methylene chloride) , chloroform, methylchloroform, carbon tetrachloride, monochlorobenzene, dichlorobenzene, etc.) can be used alone or in combination.

The binder for the dye can be selected from known natural or synthetic resins, and specifically, cellulose resins (e.g. EVA, nitrocellulose, cellulose phosphate, cellulose acetate, cellulose butyrate, methyl cellulose, ethyl cellulose, methyl cellulose, etc.), acrylic resins (e.g., polymethyl methacrylate, polybutyl methacrylate, polybutyl acrylate, polymethacrylic acid, polyacrylamide, polymethacrylamide, polyacrylonitrile, etc.), vinyl resins (e.g., polystyrene, polyvinyl acetate, etc.) , polyvinyl chloride, polyvinyl alcohol, polyvinylpyrrolidone, etc.), polycarbonates, polyesters, polyamide resins, epoxy resins, phenol resins, polyolefin resins (e.g., polyethylene, polypropylene, etc.), synthetic copolymer resins, etc. . Application is by spray,
This can be carried out using general-purpose coating methods such as roller coating, spinner coating, and blade coating.

When forming an organic thin film with a resin, the content of the disazo compound or tetrakisazo compound in the thin film! Preferably at ~0% by weight/! ~? It is 0 weight i%, and the rest is a binder.

Further, the vapor deposition thickness or dry thickness of the organic thin film is 702 m or less, preferably 702 m or less.

Furthermore, an anti-fading agent and a coloring agent can be contained in the organic thin film as required.

The material of the support used in the present invention is known to those skilled in the art, and may be transparent or opaque to the laser beam used. Specifically, glass, quartz,
Ceramics, paper, metals, plastics (e.g.
(acrylic resin, methacrylic resin, polyester resin, polyolefin resin, polystyrene resin, polyamide resin, polycarbonate resin, etc.).

When writing and recording is performed by irradiating a laser beam from the support side, it must be transparent to the laser beam.On the other hand, when writing and recording is performed from the opposite side of the support, that is, the surface of the recording layer. , need not be transparent to laser light. However, when reading and reproducing using transmitted light,
Must be transparent to readout laser light. On the other hand, when readout and reproduction is performed using reflected light, the readout laser beam (transparent or opaque may be used).Furthermore, the support may be provided with guide grooves formed with unevenness as necessary. Further, an undercoat layer made of, for example, an ultraviolet curing resin may be provided.

The optical information recording medium of the present invention is basically one in which an organic thin film is provided on the above-mentioned support, but if necessary, between the support and the organic thin film, aluminum, silver, A reflective layer such as a vapor deposited layer or a laminate layer of a reflective metal such as chromium or tin can be provided.

Information is recorded on the organic thin film by the formation of pits in the organic thin film due to the thermal effect of irradiation with focused laser beams.If the depth of the pits is made the same as the thickness of the organic thin film, the pit area (= To reproduce information, if a laser beam with the same wavelength as the laser beam used for writing is used, but with a lower intensity, the readout beam will be largely reflected in the pit area, but in the non-pit area. This is done by detecting the difference between the reflected light from pit-formed areas and non-pit-formed areas.Another method is to use a laser beam of the first wavelength that is absorbed by the organic thin film. It is also possible to perform real-time recording and playback (using a laser beam of the second wavelength that substantially passes through the two organic thin films. This is done by responding to changes in

Further, it is also possible to use a recording medium having a configuration in which two recording media having the same configuration as described above are arranged so that the organic thin films face each other.

"Examples" Next, the present invention will be specifically explained using synthesis examples and examples, but the present invention is not limited to the examples. In the examples, "parts" indicate "parts by weight."

Synthesis Example (Synthesis of Disazo Compound &da in Table 2) Although detailed synthesis will be omitted, first, the intermediate N,N'-diethyl-N was synthesized according to the following synthetic route.

N/i-s(4t-aminophenyl)-ethylenediamine (G-j) was synthesized.

(G-/) (G-2) (G-J) (G-4t) (G-t) p, w, Hifumoto (P, W,) (ickmott.

J, Chem, Soc, (C), /? ≦
6.6≦6), N-ethylaniline (G
-/) and/, N from 2-dibromoethane (G-co),
N'-Siete-N, N'-diphenyl-ethylenediamine (G-3) was synthesized. Next, N,N'-diethyl-N,N'-diphenyl-ethylenediamine was nitrated by a conventional method to give a dinitro compound (G-1), and this product was converted to N,N-dimethylformamide (D
MF) with iron and hydrochloric acid to form the intermediate N, N'-
Diethyl-N,N'-bis(4t-7minophenyl)-ethylenediamine (G-j) was obtained.

N, N'-diethyl-NN' obtained above
-Bis(couaminophenyl)-ethylenediamine! ,
+ g (θ, 0.2 mol) in concentrated hydrochloric acid 30 ml and water y□
The mixture was added to dilute hydrochloric acid prepared from ml and stirred well at room temperature for 30 minutes.

The mixture was then cooled to 0.6C and added 3.0% sodium nitrite. 'A solution of 12g dissolved in water/11ml.
It was added dropwise over a period of about 2θ minutes at 'C. Thereafter, the mixture was stirred at the same temperature for 7 hours, and after filtering off a small amount of unreacted substances, 11 ml of hydrofluoric acid was added to the filtrate, and the precipitated crystals were collected by filtration. The crystals were washed with a small amount of cold water and then dried to obtain red crystals of bisdiazonium fluoroborate 7, 1 gg (yield: 7%).

Next, 2 g of the diazonium salt thus obtained and 72 g of 2-hydroxy-3-naphthoic acid anilide (A(Cp-/) in Table 1) as a coupler were mixed with N,N-
Dimethylformamide, dissolved in 200 m/1, 2 g of sodium acetate and water/! A solution consisting of ml o'
The mixture was added dropwise over a period of about 20 minutes at a temperature of 30°C, and then stirred at room temperature for about 1 hour. After that, the generated precipitate was collected by filtration, and
After washing with 1 ml of water, this was washed with 10 ml of acetone,
After drying, 2.73g of bisazo compound (yield ♂3%)
I got it.

The decomposition temperature of this compound was 2700C or higher.

The elemental analysis values and absorption spectrum are as follows.

Elemental analysis value molecular formula woC52H46N804 (!l: site Cchi
N% N% Calculated value 73.7g! , 74t/j, 23
Fruitful 4 li direct 23. Otsu / j, j”
, 2 /J, J/IR absorption spectrum (KB
r tablet) Absorption of amide: /J7jcm" FD mass spectrum m/e == 74 is the molecular ion peak example of Otsu/Disazo compound synthesized in the synthesis example
Bis(diethylamino)-1, B/-dimethyltriphenylmethane! Part and 5 parts of polycarbonate of bisphenol A to dichloromethanta! This was ground and mixed in a mail mill to prepare a solution, and this coating solution was coated on a conductive transparent support (10 gμm
A vapor-deposited film of indium oxide is provided on the surface of a polyethylene terephthalate film. An electrophotographic photoreceptor having a single-layer electrophotographic photosensitive layer with a thickness of about r μm was prepared by coating the mixture on a surface resistance/θ3Ω) and drying it.

This electrophotographic photoreceptor was charged with a corona discharge of +jKV (: to +<toov) using an electrostatic copying paper tester (Model 5P-4T2♂), and then charged with tungsten with a color temperature of 27!+toK. The surface was irradiated with light using a lamp so that the surface potential became 4t luX, the time required for the surface potential to attenuate to half of the initial surface potential was determined, and the half-decrease exposure amount (Eso mA!ux, sea) was measured. 2. jl″luX, Sec.

In Examples 4 to 4, the azo compounds shown in Table 6 were used instead of the disazo compounds synthesized in the synthesis examples.
An electrophotographic photoreceptor having a single layer structure was prepared in the same manner as in Example 1, and the half-reduced exposure amount E50 due to positive charging was measured. The results obtained are shown in Table 6.

Table 3 Example/6 1 part of the disazo compound synthesized in Synthesis Example and 1 part of polyester resin (trade name: Vylon 200, manufactured by Toyobo ■) were mixed with tetrahydrofuran! After dispersing in a ball mill for 20 hours with a solution dissolved in O part, using a wire round rond, a conductive support (2 parts, a polyethylene terephthalate film with a thickness of 2 μm and an aluminum vapor-deposited film provided on the surface.Surface electrical resistance A charge generation layer having a thickness of 0.!μm was prepared on a two-wheel cloth (two-wheeled cloth) by drying.

Next, on the charge generation layer, 3.4 parts of p-(diphenylamino)hensaldehyde N'-methyl-N'-phenylhydrazone and the polycarbonate moiety of bisphenol A were mixed with 73.3 parts of dichloromethane and 2 parts of 2-dichloroethane.
B. The solution dissolved in the ≦ part was coated using a wire round rond and dried to form a charge transport layer with a thickness of 77 μm, thereby producing an electrophotographic photoreceptor having an electrophotographic photosensitive layer consisting of two layers.

This photoreceptor was charged with a corona discharge of 14KV (initial surface potential when charged for 2 to 3 seconds).Then, light from a tungsten lamp was irradiated to the surface of the photoreceptor with an illumination intensity of 30JJux, and the surface potential was increased. The surface potential (residual potential) VR was measured when exposed at an exposure amount of half (-attenuation) of the initial surface potential VO and an exposure amount of E50 and ≦θlux, sec.

Further, similar measurements were repeated 0 times at 30θ. The results are shown in Table 7.

Table 7 Examples 77 to 3j In Example/g, the same as Example/6 except that the azo compound shown in the 'lc' table was used instead of the disazo compound synthesized in the Synthesis Example. An electrophotographic photoreceptor was prepared, and the half-decrease exposure amount E50 was measured in the same manner as in Examples.The results are shown in Table 1.

Table 2 further Examples 77-3! Regarding the electrophotographic photoreceptor, measurements were repeated 30Q0 times in the same manner as in Example/B, and the initial surface potential Vo, half-life exposure Eso, and residual potential all showed little variation, and were extremely stable and excellent. Ta.

Comparative Examples/~2 Example/6 (: Same as Example/6 except that disazo compounds represented by the following structural formulas (1) and (II) are used instead of the disazo compound synthesized in the synthesis example used in An electrophotographic photoreceptor having a two-layer structure was prepared, and the initial surface potential VO% half-reduced exposure amount Eso and residual potential V were prepared in the same manner as in Example 6.
R was measured. Furthermore, as is clear from the results of the test F, which was repeated 3θθ0 times in the same manner as in Example 7g: extremely,
It is excellent.

Example 36 0 parts of the trisazo compound synthesized in Synthesis Example, a copolymer of benzyl methacrylate and methacrylic acid ([
[η] 100 parts of 3θ0C methyl ethyl ketone = θ, /co, methacrylic acid-containing J, 2.9%) was added to 660 parts of dichloromethane, and the mixture was ultrasonically dispersed.

This dispersion was coated on a grained aluminum plate with a thickness Q of 23 mm and dried to prepare an electrophotographic photosensitive printing plate material having an electrophotographic photosensitive layer with a dry film thickness of <mm.

After charging the surface potential of the photosensitive layer to approximately +6θ0v by corona discharge (+, <KV) on this sample in a dark place, tungsten light with a color temperature of 2rj4t0 was applied to the sample surface (yellow illuminance, 2.0v). 0, when exposed with Jux, the half-reduced exposure amount is 3
, j lux, sec.

Next (2.) Reduce the surface potential of this sample to approximately +4tOOV in the dark.
After being electrically charged, it was brought into close contact with a transparent original with a positive image and imagewise exposed. This was dissolved in l5oper H (Esso Standard, petroleum solvent)/17117θ parts (: fine particles (=dispersed polymethyl methacrylate (toner)).
! By adding 0.0 parts of soybean oil lecithin and 0.0 parts of soybean oil lecithin, a clear positive toner image could be obtained by immersing the prepared toner in a liquid developer.

Further, the toner image was fixed by heating at 1000C for 3 seconds. This printing plate material is metasilicate) IJium hydrate 7
0 parts to 97,790 parts of glycerin, ethylene glycol! ! θ
part, and ethanol/! By immersing it in a solution dissolved in the θ portion for about 7 minutes and washing it with water while lightly brushing it; the electrophotographic photosensitive layer in the area to which the toner was not attached was removed, and a printing plate was obtained.

Also, instead of using liquid developer, the obtained electrostatic latent image can be used with Xerox 3! After developing with a magnetic brush using a θθ toner (manufactured by Fuji Xerox ■), the image was fixed by heating at RO0C for 30 seconds. Next 1: A printing plate was also obtained by removing portions of the photosensitive layer to which toner was not attached using an alkaline solution.

Hamadastar gθθCD, the printing plate made in this way
Very clear prints with no stains printed using an offset printing machine using a conventional method! I was able to print the guide.

Example 37 Nitrocellulose solution (manufactured by Daicel Chemical Industries, Ltd., methyl ethyl ketone, 2.Iwt related solution solution ogz The disazo compound My, 3.og synthesized in the synthesis example and 10θg of tetrahydrofuran were mixed and sufficiently dispersed. This dispersion was mixed with acrylic Spinner coating method (10θor
pm) and then dried at a temperature of ♂0°C for 2 hours (
film thickness 0.3 μm). The recording medium prepared in this manner was mounted on a turntable, and while rotating the turntable with a motor to /70θr, p, m, the spot side /θmW and l'MH2 were focused to /, 0 μm.
Helium-neon laser light (oscillation wavelength 63 nm)
) was irradiated onto the surface of the recording layer in the form of a track to perform recording.

When the surface of the recorded recording layer was observed using a scanning electron microscope, clear pits were observed.

Furthermore, when the above-mentioned laser beam with low output power was incident on this recording medium and the reflected light was detected, a waveform having a sufficient S/N ratio was obtained.

Claims (1)

[Scope of Claims] A photosensitive composition characterized by containing at least one of a disazo compound represented by the following general formula [1] or a tetrakisazo compound represented by the following general formula [2] thing. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [1] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [2] In the general formulas [1] and [2], Cp represents a coupler residue. Ar represents a divalent aromatic carbocyclic group, a divalent aromatic heterocyclic group, or a substituent thereof. R^1 represents an alkyl group, an aralkyl group, an aryl group, or a substituted product thereof. R^2 represents a hydrogen atom, an electron-withdrawing group, or a substituted or unsubstituted alkyl group. R^3 represents a hydrogen atom or an electron-withdrawing group. R^4 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or a substituted product thereof. X is an atomic group represented by the following general formula [3]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [3] (However, R^5 and R^6 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, or a substituent thereof, R^5 and R^6 may be combined with each other to form a condensed polycyclic aromatic ring. l and n are 0 or an integer of 1 to 6, m is 0 or 1.) q is 0 or 1, and when q is 0, -N=N-Cp is directly bonded to any position of Ar.