JPH0549104B2 - - Google Patents

Description

[Detailed description of the invention]

"Industrial Application Field" The present invention relates to a photoconductive composition containing a novel disazo compound or tetrakisazo compound. The present invention also relates to a heat mode optical information recording medium that performs recording and reproduction by causing a state change using a high-density energy beam. ``Prior art'' Electrophotography has already been covered by Carlson's U.S. patent.
No. 2,297,691 discloses a photoconductive material consisting of a support coated with a dark insulating material whose electrical resistance changes depending on the dose of radiation received during image exposure. The photoconductive material is generally first given a uniform surface charge in the dark after dark adaptation for a suitable period of time. The material is then imagewise exposed to a pattern of radiation that has the effect of reducing the surface charge depending on the relative energy contained in different parts of the radiation pattern. The surface charge or electrostatic latent image thus left on the surface of the photoconductive material layer (electrophotographic photosensitive layer) then becomes a visible image when the surface is contacted with a suitable electrometric indicator material, i.e., toner. . 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. The electrostatic latent image can also be transferred to a second support (e.g. paper, film, etc.).
can be transferred to Similarly, the electrostatic latent image is
It is also possible to transfer the image to a support and develop it there. Electrophotography is one of the image forming methods in which images are formed in this manner. The basic characteristics required of an electrophotographic photoreceptor in such electrophotography are (1) ability to be charged to an appropriate potential in the dark, (2) less dissipation of charge in the dark, ( 3) The charge can be quickly dissipated by light irradiation. Conventionally, materials used as photoconductive materials for electrophotographic photoreceptors include selenium, cadmium sulfide,
These include zinc oxide. However, while these inorganic materials have many advantages, they also have various disadvantages. For example, selenium, which is currently widely used, satisfies conditions (1) to (3) above, but
It also has drawbacks such as difficult manufacturing conditions, high manufacturing costs, lack of flexibility, difficulty in processing it into a belt shape, and sensitivity to heat and mechanical shock, requiring careful handling. Cadmium sulfide and zinc oxide are used as electrophotographic photoreceptors by being dispersed in a resin as a binder, but they cannot be used as they are because of mechanical drawbacks such as smoothness, hardness, tensile strength, and abrasion resistance. Cannot be used repeatedly. In recent years, electrophotographic photoreceptors using various organic materials have been proposed in order to eliminate the drawbacks of these inorganic materials, and some of them have been put into practical use. For example, poly-N-vinylcarbazole and 2,4,7
-Electrophotographic photoreceptor consisting of trinitrofluoren-9-one (US Patent No. 3,484,237), poly-N-vinylcarbazole sensitized with pyrylium salt dye (Japanese Patent Publication No. 1983-25658), mainly composed of organic pigments. There is an electrophotographic photoreceptor (Japanese Patent Application Laid-Open No. 47-37543) containing a eutectic complex consisting of a dye and a resin (Japanese Patent Application Laid-Open No. 47-10785). Electrophotographic photoreceptors using such organic materials are
Since it can be produced by coating by appropriately selecting a binder, a photoreceptor with extremely high productivity and low cost can be provided, and its mechanical properties and flexibility can also be improved. Furthermore, the wavelength of light sensitivity can be freely controlled by selecting the dye and organic pigment. However, on the other hand, it had low photosensitivity and was not suitable for repeated use, so it did not fully meet the requirements as an electrophotographic photoreceptor. As a result of intensive research to eliminate the drawbacks of the conventional electrophotographic photoreceptors, the present inventors have discovered that an electrophotographic photoreceptor using a photoconductive composition containing a novel tetrakisazo compound has been successfully put into practical use. The present invention was achieved by discovering that it has high sensitivity and high durability that can be used for. On the other hand, conventional recording methods in which a beam of high energy density is irradiated onto an information recording medium to change physical property constants such as transmittance, reflectance, and refractive index, produce images with extremely high resolution and contrast. It has the advantages of being suitable for recording computer output and transmitted time-series signals, as it has the characteristics of being able to obtain information, add information later, and record simultaneously with exposure. have
COM (Computer Output Micro),
It is applied to microfacsimile, printing plates, optical disks, etc. For example, the recording medium used in optical disk technology is
Optically detectable small pits of around 1 μm can be formed into spiral or circular tracks to store high-density information. To write information on such a disk, a focused laser is scanned over the surface of the laser sensitive layer, and only the surface irradiated with this laser beam forms pits, and these pits are formed in the form of spiral or circular tracks. do.
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 affected locations by evaporation or melting. The information recorded on the optical disk in this way is
It is detected by scanning a laser along the track and reading the optical changes in the areas where pits are formed and those where pits are not formed. Conventionally, information recording media that can perform heat mode recording include 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 to laser light, which reduces the efficiency of laser use and therefore makes it impossible to obtain high sensitivity characteristics, or the laser light during recording. There were problems such as a significant increase in output. 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 slight increases in temperature. Therefore, "direct read after write" capability [DRAW
(direct read and write)] is required for a recording medium that has high absorption efficiency for the laser beam used, a reflectance that allows sufficient focus control when reading records, or a stable recorded image. However, a recording medium containing an organic thin film that is sufficiently satisfactory from a practical point of view has not yet been developed. The present inventors have arrived at the present invention as a result of intensive research 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 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 Problems" The present invention is characterized by the fact that the storage medium represented by the following general formulas [] and [] has a high absorption efficiency for the laser beam used, and that the focus control during recording and reading is performed. A recording medium containing an organic thin film that is sufficiently satisfactory from a practical point of view must satisfy various characteristics such as having a sufficient reflectance for recording, or the stability of a recorded image. Not yet. The present inventors have arrived at the present invention as a result of intensive research 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 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 Problems" The present invention provides a photosensitive composition containing at least one disazo compound or tetrakisazo compound represented by the following general formulas [] and []. It is. In the general formulas [] and [], Cp represents a coupler residue, and is preferably selected from the coupler components shown below.

【formula】

【formula】

【formula】

【formula】

[expression] or

[Formula] X is necessary for condensation with the benzene ring in the above formula to which the hydroxy group and Y are bonded to form an aromatic ring or a heterocycle (these rings may be substituted or unsubstituted) Y represents a hydrogen atom, -CONR ⁴ R ⁵ , -COOR ⁴ , -CONHNR ⁴ R ⁵ , -
CONHN=CH−R ⁴ or

[Formula] represents. R ¹ represents an alkyl group, a phenyl group, or a substituted product thereof, and R ² represents a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, or a substituted or unsubstituted amino group. R ³ represents an alkyl group, an aromatic ring group, a heteroaromatic ring group, or a substituent thereof, and R ⁴ and R ⁵ represent a hydrogen atom, an alkyl group, an aromatic ring group, a heteroaromatic ring group, or a substituent thereof. represents a permutation product of. Z is

[Formula] represents -O-, -S- or -Se-. R ⁶ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryl group having 1 to 12 carbon atoms.
There are an alkoxycarbonyl group having an alkoxy group, an aryloxycarbonyl group having 6 to 20 carbon atoms, and an acyl group having 1 to 20 carbon atoms. When R ⁶ is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group,
Examples include isobutyl group, isohexyl group, neopentyl group, and tert-butyl group. When R ⁶ is a substituted alkyl group, the substituent is:
Hydroxy group, alkoxy group having 1 to 12 carbon atoms, cyano group, alkylamino group having 1 to 8 carbon atoms, dialkylamino group having two alkyl groups having 1 to 8 carbon atoms, halogen atom, having 6 to 15 carbon atoms There are aryl groups, etc. Examples thereof include hydroxyalkyl groups (e.g., hydroxymethyl group, 2-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, 2-ethoxyethyl group, etc.), cyanoalkyl group (e.g. cyanomethyl group, 2-cyanoethyl group, etc.), (alkylamino)alkyl group (e.g.
(methylamino)methyl group, 2-(methylamino)
ethyl group, (ethylamino)methyl group, etc.), (dialkylamino)alkyl group (e.g., (dimethylamino)methyl group, 2-(dimethylamino)ethyl group, etc.), halogenoalkyl group (e.g., fluoromethyl group, chloro methyl group, bromomethyl group, etc.), aralkyl group (eg, benzyl group, phenethyl group, etc.). When R ⁶ is an unsubstituted alkoxycarbonyl group,
Specific examples thereof include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, and benzyloxycarbonyl group. When R ⁶ is an unsubstituted aryl group or an unsubstituted aryloxycarbonyl group, specific examples thereof include a phenyl group, a naphthyl group, a pyridyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, and the like. When R ⁶ is an unsubstituted acyl group, specific examples include an acetyl group, a propionyl group, a benzoyl group,
Examples include naphthoyl group and nicotinoyl group. When R ⁶ is a substituted alkoxycarbonyl group, substituted aryloxycarbonyl group, or substituted acyl group, the substituent can be the same as the substituent for the substituted alkyl group in R ⁶ described above, and the number of substituents is 1. from 3 to 3, and when multiple substituents are bonded, they may be the same or different from each other, and may be in any combination;
Further, the bonding position of the substituent is arbitrary. X is a group capable of bonding with the benzene ring to which the hydroxy group and Y are bonded to form an aromatic ring such as a naphthalene ring or anthracene ring, or a heterocyclic ring such as an indole ring, carbazole ring, benzocarbazole, or dibenzofuran ring. . When X is an aromatic ring or a heterocyclic ring having a substituent, the substituent is a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, etc.), a lower alkyl group, preferably a lower alkyl group having 1 to 8 carbon atoms. (For example, methyl group, ethyl group, propyl group, butyl group, isopropyl group, isobutyl group, etc.), and the number of substituents is 1 or 2, and when there are 2 substituents, they are may be the same or different. R ¹ is an alkyl group, preferably having 1 carbon number
There are ~12 alkyl or phenyl groups. When R ¹ is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group,
Isobutyl group, isoamyl group, isohexyl group,
Examples include neopentyl group and tert-butyl group. When R ¹ is a substituted alkyl group, the substituent includes a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group having 1 to 12 carbon atoms, and an alkyl group having 1 to 12 carbon atoms. Dialkylamino group having 2, halogen atom, carbon number 6-15
aryl groups, etc. Examples include hydroxyalkyl groups (e.g. hydroxymethyl group,
2-hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, etc.), alkoxyalkyl group (e.g., methoxymethyl group, 2-hydroxypropyl group, etc.),
methoxyethyl group, 3-methoxypropyl group, ethoxymethyl group, 2-ethoxyethyl group, etc.), cyanoalkyl group (e.g. cyanomethyl group, 2-ethoxyethyl group, etc.)
cyanoethyl group, etc.), aminoalkyl group (e.g.
(aminomethyl group, 2-aminoethyl group, 3-aminopropyl group, etc.), (alkylamino)alkyl group (for example, (methylamino)methyl group, 2-(methylamino)ethyl group, (ethylamino)methyl group, etc. ), (dialkylamino)alkyl group (e.g., (dimethylamino)methyl group, 2-(dimethylamino)
ethyl group, etc.), halogenoalkyl groups (eg, fluoromethyl group, chloromethyl group, bromomethyl group, etc.), and aralkyl groups (eg, benzyl group, phenethyl group, etc.). When R ¹ is a substituted phenyl group, the substituent includes a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group having 1 to 12 carbon atoms, and an alkyl group having 1 to 12 carbon atoms. Dialkylamino group having 2, halogen atom, carbon number 1-6
There are alkyl groups, nitro groups, etc. Examples include hydroxyphenyl group, alkoxyphenyl group (e.g., methoxyphenyl group, ethoxyphenyl group, etc.), cyanophenyl group, aminophenyl group, (alkylamino)phenyl group (e.g., (methylamino)phenyl group, (ethylamino)phenyl group, etc.), (dialkylamino)phenyl group (e.g., dimethylamino)phenyl group, etc.), halogenophenyl group (e.g., fluorophenyl group, chlorophenyl group, bromophenyl group, etc.), alkylphenyl group (e.g. , tolyl group, ethyl phenyl group, cumenyl group, xylyl group, mesityl group, etc.),
Lists a nitrophenyl group and a substituent having two or three of these substituents (which may be the same or different) (the position of the substituents or the positional relationship between the substituents is arbitrary) be able to. R ² is a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group having an alkoxy group having 1 to 12 carbon atoms, or an aryloxy group having an aryloxy group having 6 to 20 carbon atoms. A carbonyl group and a substituted or unsubstituted amino group are preferred. When R ² is a substituted amino group, specific examples thereof include methylamino group, ethylamino group, propylamino group, phenylamino group, tolylamino group, benzylamino group, phenethylamino group, dimethylamino group, diethylamino group, diphenylamino group, etc. be able to. When R ² is a lower alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group,
Examples include isopropyl group and isobutyl group. When R ² is an alkoxycarbonyl group, specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, an isopropoxycarbonyl group, a benzyloxycarbonyl group, and the like. When R ² is an aryloxycarbonyl group, specific examples thereof include a phenoxycarbonyl group and a toroxycarbonyl group. R ³ and R ⁵ include aromatic ring groups such as alkyl groups having 1 to 20 carbon atoms, phenyl groups, and naphthyl groups;
A heteroaromatic ring group containing an oxygen atom, a nitrogen atom, a sulfur atom, etc., such as a dibenzofuranyl group, a carbazolyl group, a benzocarbazolyl group, or a substituted product thereof is preferred. When R ³ or R ⁵ 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 R ¹ . When R ³ or R ⁵ 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, an example of the substituent is a hydroxy group. , cyano group, nitro group, halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, etc.), alkyl group having 1 to 12 carbon atoms (e.g., methyl group, ethyl group, propyl group, isopropyl group, etc.) having 1 carbon number
~12 perfluoroalkyl groups (e.g. trifluoromethyl group, pentafluoromethyl group, perfluorobutyl group, perfluorohexyl group, etc.), alkoxy groups having 1 to 12 carbon atoms (e.g. methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, isopropoxy group, isobutoxy group, isoamyloxy group, tert-butoxy group, neopentyloxy group, etc.), amino group, alkylamino group having 1 to 12 carbon atoms (e.g. methylamino group, ethyl amino group, propylamino group, etc.), dialkylamino group having 1 to 12 carbon atoms (e.g., dimethylamino group, diethylamino group, N-
methyl-N-ethylamino group, etc.), carbon number 6-12
arylamino group (e.g., phenylamino group, tolylamino group, etc.), diarylamino group having two aryl groups having 6 to 15 carbon atoms (e.g.,
diphenylamino group, etc.), carboxyl group, alkali metal carboxylate group (examples of alkali metals (cations), Na, K, Li, etc.), alkali metal sulfonato groups (examples of alkali metals (cations), Na, K, Li etc.), alkylcarbonyl groups (e.g. acetyl group, propionyl group, benzylcarbonyl group, etc.), arylcarbonyl groups having an aryl group having 6 to 12 carbon atoms (e.g. benzoyl group, toluoyl group, alkylthio group having 1 to 12 carbon atoms), groups (e.g., methylthio group, ethylthio group, etc.), or arylthio groups having 1 to 12 carbon atoms (e.g., phenylthio group, tolylthio group, etc.), and the number of substituents is 1 to 3, When multiple substituents are bonded, they may be the same or different from each other and may be in any combination, and the bonding positions of the substituents may be arbitrary. R ⁴ is a hydrogen atom and has 1 carbon atom. ~20 alkyl groups, aromatic ring groups such as phenyl groups, naphthyl groups, heteroaromatic ring groups containing oxygen atoms, nitrogen atoms, sulfur atoms such as dibenzofuranyl groups, carbazolyl groups, benzocarbazolyl groups, or There are these substituents. When R ⁴ is a substituted or unsubstituted alkyl group, aromatic substituent, or heteroaromatic ring group, the above-mentioned R ³ and
The same groups as in the case of R ⁵ can be mentioned. Also, Cp

In the case of [formula] and

[Formula] and Y is −CONR ⁴ R ⁵ , −CONHNR ⁴ R ⁵ or

In the case of [Formula], R ⁴ and R ⁵ can form a ring together with the nitrogen atom or carbon atom to which they are bonded. Specific examples include a pyrrolidine ring, a piperidine ring, a morpholine ring, a cyclopentane ring, and a cyclohexane ring. L ₁ and L ₂ represent a hydrogen atom or an electron-withdrawing group. Specific examples of electron-withdrawing groups include halogen atoms (for example, fluorine atoms, chlorine atoms, bromine atoms, etc.), nitro groups, cyano groups, and alkoxycarbonyl groups (methoxycarbonyl groups, ethoxycarbonyl groups, etc.). . Ar represents a divalent aromatic carbocyclic group, a divalent aromatic heterocyclic group, or a substituent thereof. Specific examples thereof include divalent aromatic carbocyclic groups, divalent aromatic carbocyclic groups, and substituted products thereof shown in the following structures.

【formula】

【formula】

【formula】

【formula】

【formula】

[Formula] As the substituent, the same groups as the above-mentioned substituents for R ³ and R ⁵ can be mentioned. Examples of B ¹ and B ² include hydrogen atoms, halogen atoms (e.g., chlorine atoms, bromine atoms, iodine atoms), alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, and alkyl groups having 1 to 6 carbon atoms. alkoxycarbonyl group,
There are aryl groups having 6 to 15 carbon atoms, aryloxy groups having 6 to 15 carbon atoms, and aryloxycarbonyl groups having 6 to 15 carbon atoms. However, B ₁ and B ₂ are never both hydrogen atoms. When B ¹ and B ² are substituted or unsubstituted alkyl groups, alkoxy groups, alkoxycarbonyl groups, aryl groups, aryloxy groups, or aryloxycarbonyl groups, the alkyl and aryl moieties of these structures are the same as the above-mentioned R The same groups as the substituted or unsubstituted alkyl group and aryl group in ⁶ can be mentioned. The coupler residue Cp is used from the viewpoint that it provides an electrophotographic photosensitive layer with high photosensitivity and that the manufacturing raw material compound can be easily obtained, so that the trisazo compound can be manufactured at low cost.

[Formula] is preferred. Moreover, as X, a benzene ring, a carbazole ring, and a dibenzofuran ring are preferable, and as Y,

[Formula] is preferred. As R ⁴ and R ⁵ , a phenyl group in which one has a hydrogen atom and the other has a substituent is preferable. Substituents for phenyl groups include alkyl groups such as methyl and ethyl groups, halogen atoms such as fluorine, chlorine and bromine, alkoxy groups such as methoxy and ethoxy groups, and perfluoroalkyl groups such as trifluoromethyl. is preferred. A more preferred example of a substituent is a trifluoromethyl group or a combination of a trifluoromethyl group and a halogen atom. Specific examples of the disazo compound represented by the general formula [] are shown in Table 1 (indicated by the substituents of the general formula []).

【table】

【table】

[Table] Next, specific examples of tetrakisazo compounds represented by the general formula [] are shown in Table 2 (general formula []
).

【table】

[Table] Table 3 shows the structure of the coupler residue Cp used in Tables 1 and 2.

【table】

【table】

【table】

[Table] The novel disazo compounds and tetrakisazo compounds used in the present invention can be easily produced by using known reactions. That is, the corresponding amino compound of the general formula [] is diazotized according to a conventional method, the obtained diazonium salt is isolated, and then it is dissolved in a suitable solvent such as N,N-
It can be easily synthesized by carrying out a coupling reaction with the above-mentioned coupler residues (eg, naphthol AS couplers) in dimethylformamide in the presence of an alkali, such as sodium acetate or sodium hydroxide. When the composition of the present invention is used in an electrophotographic photomaterial, a disazo compound represented by the above general formula or
It has an electrophotographic photosensitive layer containing one or more tetrakisazo compounds. Various forms 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 high efficiency, and the generated charge carriers can also be transported using the disazo compound or tetrakisazo compound as a medium. You can, but
It is more effective to use a charge carrier transport compound as a medium for transport. To create 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 preferably 3 to 30 microns, preferably 5 to 20 microns. To prepare an electrophotographic photoreceptor of type (b), a disazo compound or a tetrakisazo compound is vacuum-deposited on a conductive support, or the disazo compound or a tetrakisazo compound is dissolved in a solvent such as an amine and applied. It is obtained by dispersing fine particles of the compound in a suitable solvent or, if necessary, in a solvent in which a binder is dissolved, coating and drying, and then coating and drying a solution containing a charge carrier transport compound and a binder thereon. The thickness of the disazo compound or tetrakisazo compound layer serving as the charge carrier generation layer at this time is 4μ or less, preferably 2μ or less,
The thickness of the charge carrier transport medium layer is preferably 3 to 30 microns, preferably 5 to 20 microns. The disazo compound or tetrakisazo compound used in the photoreceptors of types (a) and (b) is processed by a dispersing machine such as a ball mill, sand mill, or vibration mill to determine the particle size.
It is used after being ground to 5μ or less, preferably 2μ or less. When the amount of disazo compound or tetrakisazo compound used in the electrophotographic photoreceptor of type (a) is too small, the sensitivity will be poor, and when it is too large, the charging property will be poor, and the strength of the electrophotographic photosensitive layer may be weakened. However, the proportion of the disazo compound or tetrakisazo compound in the electrophotographic photoreceptor layer is 0.01 to 2 times the weight of the binder, preferably 0.05 to 2 times the weight of the binder.
The ratio of the charge carrier transporting compound added as needed is preferably 0.1 to 2 times, preferably 0.3 to 1.3 times the weight of the binder.
In the case of a charge carrier transporting compound which itself can be used as a binder, the amount of the disazo compound or tetrakisazo compound added is preferably 0.01 to 0.5 times the weight of the binder. Furthermore, when forming a disazo compound- or tetrakisazo compound-containing layer to serve as a charge carrier generation layer in the electrophotographic photoreceptor of type (b), the amount of the disazo compound or tetrakisazo compound used is preferably 0.1 times or more by weight relative to the binder resin. 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 0.01 to 10 times the weight of the binder, preferably 0.2 to 10 times the weight of the binder.
2.0 times by weight is preferred. If a polymeric charge carrier transport compound is used which itself can be used as a binder, no other binder can be used. In addition, for the type (b) photoreceptor, a patent application was filed in 1983.
No. 53183, Patent Application No. 109906, Patent Application No. 1983-
As described in each specification of No. 118414, charge carrier transport compounds such as hydrazone compounds and oxime compounds can be added to the charge carrier generation layer. When producing the electrophotographic photoreceptor of the present invention, additives such as a plasticizer or a sensitizer may be used together with the binder. The conductive support used in the electrophotographic photoreceptor of the present invention includes a metal plate such as aluminum, copper, or zinc, a plastic sheet such as polyester, or a plastic film on which a conductive material such as aluminum, indium oxide, or SnO ₂ is deposited. , dispersed coating, or conductive treated paper. 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-acrylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, Vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone-alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, poly-N-vinylcarbazole. These binders can be used alone or as a mixture of two or more. Plasticizers include biphenyl, biphenyl chloride,
o-terphenyl, p-terphenyl, dibutyl phthalate, dimethyl glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, polypropylene, polystyrene, dilaurylthiodipropionate, 3,5-dinitrosalicylic acid, various fluorocarbons Examples include hydrocarbons. In addition, silicone oil or the like may be added to improve the surface properties of the electrophotographic photoreceptor. Examples of the sensitizer include chloranil, tetracyanoethylene, methyl violet, rhodamine B, cyanine dye, merocyanine dye, pyrylium dye, thiapyrylium dye, and the like. 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 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 9-dicyanomethylene-2,4 , 7-trinitrofluorenone, 9-dicyanomethylene-
2,4,5,7-tetranitrofluorenone, tetranitrocarbazole chloranil, 2,3-dichloro-5,6-dicyanobenzoquinone, 2,
Examples include 4,7-trinitro-9,10-phenanthrenequinone, tetrachlorophthalic anhydride, tetracyanoethylene, and tetracyanoquinodimethane. Compounds that transport holes include compounds having an electron-donating group, such as polymers, such as (1) polyvinylcarbazole and its derivatives described in Japanese Patent Publication No. 34-10966, (2) Japanese Patent Publication No. 43-18674. Polyvinylpyrene, polyvinylanthracene, poly-2-vinyl-4-(4'-dimethylaminophenyl)-5-phenyl-oxazole, poly-3-vinyl-N-ethyl described in Japanese Patent Publication No. 43-19192 Vinyl polymers such as carbazole, (3) Polymers such as polyacenaphthylene, polyindene, copolymerization of acenaphthylene and styrene, etc. described in Japanese Patent Publication No. 19193-1983, (4) Polymers such as those described in Japanese Patent Publication No. 1987-13940, etc. Condensation resins such as pyrene-formaldehyde resin, bromopyrene-formaldehyde resin, and ethylcarbazole-formaldehyde resin described in . (5) Various triphenylmethane polymers described in JP-A-56-90883 and JP-A-56-161550. In addition, low molecular weight ones include (6) triazole derivatives described in U.S. Patent No. 3,112,197, etc., (7) oxadiazole derivatives, described in U.S. Pat. No. 3,189,447, etc., (8) Imidazole derivatives described in Japanese Patent Publication No. 37-16096, etc., (9) U.S. Patent Nos. 3615402, 3820989,
No. 3542544, Special Publication No. 1977-555, Special Publication No. 1971-
No. 10983, JP-A-51-93224, JP-A-55-
No. 108667, JP-A-55-156953, JP-A-56-
Polyarylalkane derivatives described in 36656 specification, publications, etc., (10) U.S. Patent No. 3180729, U.S. Patent No. 4278746
No., JP-A-55-88064, JP-A-55-88065,
JP-A-49-105537, JP-A-55-51086, JP-A-56-80051, JP-A-56-88141, JP-A-Sho
No. 57-45545, JP-A No. 112637-1983, JP-A-55
Pyrazoline derivatives and pyrazolone derivatives described in -74546 specification, publications, etc. (11) U.S. Patent No. 3615404 specification, Japanese Patent Publication No. 1983-
No. 10105, JP-A No. 1983-83435, JP-A No. 1983-
No. 110836, Japanese Patent Application Publication No. 119925, Publication No. 119925, Publication No. 119925, Publication No. 119925-
Phenylenediamine derivatives described in No. 3712, Japanese Patent Publication No. 47-28336, publications, etc. (12) U.S. Patent No. 3567450, Japanese Patent Publication No. 49-35702,
West German Patent (DAS) No. 1110518, US Patent No.
3180703, U.S. Patent No. 3240597, U.S. Patent No.
3658520, U.S. Patent No. 4232103, U.S. Patent No.
No. 4175961, U.S. Patent No. 4012376, Japanese Unexamined Patent Publication No. 1987-
No. 144250, JP-A-56-119132, JP-A No. 119132-
Arylamine derivatives described in No. 27577, JP-A-56-22437, publications, etc. (13) Amino-substituted chalcone derivatives described in U.S. Pat. No. 3,526,501, (14) U.S. Pat. No. 3,542,546 N written in books etc.
N-bicalbasil derivatives, (15) oxazole derivatives described in US Pat. No. 3,257,203, etc., (16) styryl anthracene derivatives described in JP-A-56-46234, etc., (17) JP-A-54- Fluorenone derivatives described in the specification of No. 110837 etc., (18) U.S. Patent No. 3717462, JP-A No. 59143-1987 (corresponding to U.S. Patent No. 4150987), JP-A-55-
No. 52063, JP-A-55-52064, JP-A-55-
46760, JP-A-55-85495, JP-A-57-11350
Hydrazone derivatives disclosed in JP-A-57-148749, JP-A-57-104144, etc. (19) U.S. Patent No. 4047948, U.S. Patent No. 4047949
No. 4,265,990, U.S. Pat. No. 4,273,846
No. 4,299,897, U.S. Pat. No. 4,306,008
and the benzidine derivatives described in the specification. In the present invention, the compound that transports charge carriers is not limited to the compounds listed in (1) to (19), and all hitherto known charge carrier transporting compounds can be used. Two or more types of these charge transport materials may be used in combination depending on the case. In addition, the photoreceptor obtained in the above manner has the following properties:
An adhesive layer or 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-59-
These include the vinylidene chloride polymer latex described in Japanese Patent Publication No. 84247, the styrene-butadiene polymer latex or aluminum oxide described in JP-A-59-114544, and the thickness of these layers is preferably 1 μm or less. The electrophotographic photoreceptor of the present invention has been described in detail above, and the electrophotographic photoreceptor of the present invention generally has the characteristics of 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 tetrakisazo compound of the present invention can be used as a photoconductive layer in the image pickup tube of a video camera, and can be applied over the entire surface of 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 image sensor having a light-receiving layer (photoconductive layer). Also,
AK Ghosh, Tom Feng, J.
Appl. Phys., 49(12), 5982 (1978)), it can also be used as a photoconductive layer in solar cells. 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 can be used in Japanese Patent Publication No. 37-17162, Japanese Unexamined Patent Publication No. 55-55
No. 19063, JP-A-55-161250, JP-A-57-
As disclosed in each publication No. 147656, the above-mentioned charge carrier transporting compounds such as oxadiazole derivatives and hydrazone derivatives are dispersed in an alkali-soluble resin solution such as a phenol resin, and the mixture is dispersed on a conductive support such as aluminum. After coating, drying, image exposure, toner development, and etching with an alkaline aqueous solution, printing plates with high resolution, high durability, and high sensitivity can be obtained, and printed circuits 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. It can be formed using various methods such as vapor deposition coating. When using the coating method, examples of organic solvents include alcohols (e.g., methanol, ethanol, isopropanol, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), amides (e.g., 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, diglyme, etc.) chlorobenzene, 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., nitrocellulose, cellulose phosphate, cellulose acetate, cellulose butyrate, methylcellulose, ethylcellulose) , butyl 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, polyvinyl chloride, polyvinyl alcohol, polyvinylpyrrolidone, etc.),
Polycarbonates, polyesters, polyamide resins, epoxy resins, phenol resins, polyolefin resins (eg, polyethylene, polypropylene, etc.), synthetic copolymer resins, and the like can be used. Application can be carried out using general-purpose coating methods such as spraying, roller coating, spinner coating, and blade coating. When forming an organic thin film together with a resin, the content of the disazo compound or tetrakisazo compound in the thin film is 5 to 90% by weight, preferably 15% by weight.
~80% by weight, the remainder being binder. Further, the vapor deposited thickness or dry thickness of the organic thin film is 10 μm or less, preferably 2 μm 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. Specific examples include glass, quartz, ceramics, paper, metals, plastics (eg, 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 read and reproduced using transmitted light, it must be transparent to the read laser beam. On the other hand, when reading and reproducing are performed using reflected light, it may be transparent or opaque to the reading laser beam.
Further, the support may be provided with a guide groove formed of unevenness, if necessary, or may be provided with an undercoat layer made of, for example, an ultraviolet curing resin. The optical information recording medium of the present invention basically has an organic thin film provided on the above-mentioned support, but if necessary, aluminum, silver, chromium, etc. may be added between the support and the organic thin film. A reflective layer such as a vapor deposited layer or a laminate layer of a reflective metal such as tin can be provided. The recording of information is carried out by the formation of pits in the organic thin film by the thermal effect of irradiation with a focused laser beam on the organic thin film. When the depth of the pit is made the same as the thickness of the organic thin film, the reflectance in the pit region can be increased. Reproducing information has the same wavelength as the laser beam used for writing, but if a laser beam with low intensity is used, the reading light will be largely reflected at the pit area.
It will be absorbed in the non-pit area,
This is performed by detecting the difference in reflected light from the pit-formed portion and the non-pit-formed portion. Another method is to use a laser beam to perform real-time recording of a first wavelength that is absorbed by the organic thin film, and use a laser beam of a second wavelength that substantially passes through the organic thin film for reproduction. The regeneration laser beam is activated by responding to changes in the reflection phase caused by the different film thicknesses in pitted and non-pitted areas. 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. In this case, since the organic thin film is isolated from the outside air, it can be protected from dust, scratches, and contact with harmful gases, and the preservation of the recording layer is significantly improved. Laser beams applied to the optical information recording medium of the present invention include Ar laser, He-Ne laser, He-Ne laser, and He-Ne laser.
Gas lasers such as CD lasers are also possible. "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 compound No. A-8) Annlen der Hemie
A dinitro compound obtained by condensing thiophene-3,4-dibromo-2,5-dicarbaldehyde synthesized by the method described in Chemie) 532 250 (1937) and p-nitrobenzyl cyanide using a piperidine catalyst. to reduce thiophene-3,4-dibromo-
2,5-bis[2-cyano-2-(p-aminophenyl)ethylenyl] was synthesized. Add 5.3g (0.01mol) of this diamino compound to 20% of concentrated hydrochloric acid.
ml and dilute hydrochloric acid prepared from 60 ml of water, stirred on a 60°C water bath, cooled to 0°C, and added a solution of 1.5 g of sodium sulfite dissolved in 20 ml of water dropwise at 0°C over about 30 minutes. did. Then, after stirring at the same temperature for 1 hour and separating a small amount of unreacted materials,
20 ml of 42% borofluoric acid was added to the solution and the precipitated crystals were collected. After washing these crystals with a small amount of water, they were dried to give 6.7 g of colored crystals of diazonium salt (yield:
92%). Next, 2.6 g of the diazonium salt obtained in this way
(3.53 mmol) and 1.9 g (7.22 mmol) of 2-hydroxy-3-naphthoic acid anilide (Cp-1 in Table 3) were added in 100 ml of N,N-dimethylformamide.
and cooled to 0°C. 10 ml of a 10% aqueous sodium acetate solution was added dropwise to this solution at 0°C, and the mixture was stirred at room temperature for 2 hours. Next, the generated precipitate was collected, washed with 300 ml of water, washed with 200 ml of acetone, and dried to obtain 3.4 g of disazo compound No. A-8. (Yield 90%) The decomposition temperature of this compound was 270°C or higher.
In addition, ν = 2200 cm ^-1 (CN absorption) and ν = 1670 cm ^-1 (amide absorption) are seen in the infrared absorption spectrum, and a peak of m/e = 1074 molecular ion + 1 is seen in the FD-mass spectrum. It was done. Example 1 1 part of a diazo compound represented by Compound No. A-1 of the present invention and 4,4'-bis(diethylamino)-
Add 5 parts of 2,2'-dimethyltriphenylmethane and 5 parts of bisphenol A polycarbonate to 95 parts of dichloromethane, grind and mix in a ball mill to prepare a solution, and apply this coating solution using a wire round rod. A conductive transparent support (100 μm
An indium oxide vapor-deposited film is provided on the surface of a polyethylene terephthalate film. surface resistance
10 ³ Ω) and dried to prepare an electrophotographic photoreceptor having a single-layer electrophotographic photosensitive layer with a thickness of about 8 μm. This electrophotographic photoreceptor was tested at +5KV using an electrostatic copying paper tester (SP-428 model manufactured by Kawaguchi Electric Co., Ltd.).
The surface is charged to +400V by corona discharge, and then the surface is irradiated with light at 4lux using a tungsten lamp with a color temperature of 2854〓, and the time required for the surface potential to attenuate to half of the initial surface potential. The half-reduction exposure amount E ₅₀ (lux·sec) was measured and found to be 10.8lux·sec. Examples 2 to 8 In Example 1, a monolayer structure was prepared in the same manner as in Example 1, except that a disazo compound or a tetrakisazo compound shown in Table 4 was used instead of the disazo compound of Compound No. A-1. An electrophotographic photoreceptor was prepared, and the half-reduction exposure amount E ₅₀ due to normal voltage was measured in the same manner as in Example 1. The results obtained are shown in Table 4.

[Table] Example 9 Disazo compound 5 represented by compound No. A-6
and 5 parts of polyester resin (trade name: Vylon 200, manufactured by Toyobo Co., Ltd.) were dispersed in a ball mill for 20 hours with a solution of 50 parts of tetrahydrofuran. Using a wire round rod, the conductive support ( An aluminum vapor-deposited film was provided on the surface of a 75 μm polyethylene terephthalate film (surface electrical resistance: 4×10 ² Ω) and dried to produce a charge generation layer with a thickness of 0.5 μm. Next, p-(diphenylamino) is added on top of the charge generation layer.
Polycarbonate of 3.6 parts of benzaldehyde N'-methyl-N'-phenylhydrazone and bisphenol A -4 parts of carbonate and 13.3 parts of dichloromethane 1,2
- Apply a solution dissolved in 26.6 parts of dichloroethane using a wire round rod and dry to a thickness of 11 μm.
An electrophotographic photoreceptor having a two-layer electrophotographic photosensitive layer was prepared by forming a charge transport layer of m. When this photoreceptor is charged by -6KV corona discharge, the initial surface potential is V ₀ , and then the illumination intensity on the photoreceptor surface is reduced to 0 lux with the light from the tungsten lamp.
The surface potential (residual potential) V when exposed to light with an exposure amount of ₅₀ and 10 lux sec, and the exposure amount required for the surface potential to attenuate to half of the initial surface potential V _{0 R} was measured for each. Similar measurements were also repeated 3000 times.
The results are shown in Table 5.

[Table] Examples 10 to 28 In Example 9, the procedure was repeated in the same manner as in Example 9, except that the disazo compound and tetrakisazo compound shown in Table 6 were used instead of the disazo compound represented by compound No. A-6. An electrophotographic photoreceptor having a two-layer structure was prepared, and the half-decrease exposure amount E ₅₀ was prepared in the same manner as in Example 9.
was measured. The results are shown in Table 6.

[Table] Example 29 Disazo compound 5 represented by compound No. A-1
40 parts of the hydrazone compound used in Example 9 and 100 parts of a copolymer of benzyl methacrylate and methacrylic acid ([η] 30°C methyl ethyl ketone = 0.12, methacrylic acid content 32.9%) were added to 660 parts of dichloromethane, and Dispersed sound waves. This dispersion was coated on a grained aluminum plate with a thickness of 0.25 mm and dried to prepare an electrophotographic photosensitive printing plate material having an electrophotographic photosensitive layer with a dry film thickness of 6 mm. The surface potential of the photosensitive layer was charged to about +600V by corona discharge (+6KV) on this sample in a dark place, and then the sample surface was exposed to tungsten light with a color temperature of 2854〓 at an illuminance of 2.0lux, which caused a half-reduced exposure. The amount is
It was 8.1lux・sec. Next, raise the surface potential of this sample to about + in the dark.
After being charged to 400V, the image was exposed by bringing it into close contact with a transparent original with a positive image. Contains a toner prepared by adding 5 parts of polymethyl methacrylate (toner) dispersed in fine particles and 0.01 part of soybean oil lecithin to 1000 parts of Isoper H (Etsuo Standard Co., Ltd., petroleum-based solvent). When immersed in a liquid developer, a clear positive toner image could be obtained. The toner image was further fixed by heating at 100° C. for 30 seconds. This printing plate material was mixed with 70 parts of sodium metasilicate hydrate, 140 parts of glycerin, and ethylene glycol.
By immersing it in a solution of 550 parts and 150 parts of ethanol for about 1 minute and washing it with a stream of water while lightly brushing, the electrophotographic photosensitive layer in the areas to which toner was not attached was removed, and a printing plate was obtained. . In addition, instead of a liquid developer, the obtained electrostatic latent image is used as a toner for Xerox 3500 (Fuji Xerox Co., Ltd.).
After developing with a magnetic brush using a commercially available product (manufactured by J.D. Co., Ltd.), the image was fixed by heating at 80°C for 30 seconds. Next, a printing plate was also obtained by removing the photosensitive layer in the areas to which toner was not attached using an alkaline solution. The printing plate made in this way is used as a Hamada star.
Using a 600CD offset printing machine, we were able to print 50,000 sheets of extremely clear prints with no spot stains using conventional methods. Example 30 Nitrocellulose solution (manufactured by Daicel Chemical Industries, Ltd.,
Methyl ethyl ketone 25wt% solution) 10g, compound
3.0 g of the disazo compound represented by No. A-6 and 100 g of tetrahydrofuran were mixed and sufficiently dispersed. After applying this dispersion to an acrylic substrate using the spinner coating method (1000r.pm), the temperature
It was dried at 80°C for 2 hours (film thickness 0.3 μm). The recording medium produced in this way was mounted on a turntable, and while the turntable was rotated by a motor at 1800 rpm, the focus was focused on a spot side of 1.0 μm.
Recording was performed by irradiating the surface of the recording layer with a helium-neon laser beam (oscillation wavelength: 633 nm) of 10 mW and 8 MHz in the form of a track. When the surface of the recorded recording layer was observed using a scanning electron microscope, clear pits were observed. Furthermore, when the above laser beam with a low output was made incident on this recording medium and the reflected light was detected, a waveform with a sufficient S/N ratio was obtained.

Claims (1)

[Scope of Claims] 1. A photosensitive composition containing at least one disazo compound or tetrakisazo compound represented by the following general formula [] or []. In the general formulas [] to [], Cp represents a coupler residue. L ¹ and L ² represent a hydrogen atom or an electron-withdrawing group. Z represents [formula] [formula] [formula] or [formula]. However, R ⁶ represents a hydrogen atom, a lower alkyl group, an aryl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, or a substituted product thereof. Ar represents a divalent aromatic carbocyclic group, a divalent aromatic heterocyclic group, or a substituent thereof. ^{B 1} and B ² represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, an aryl group, an aryloxy group, an aryloxycarbonyl group, or ^a substituted product thereof; may be the same or different groups. However, B ¹ and B ² are never both hydrogen atoms. m and n represent 0, 1, and 2.