JPS6019148A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body high in sensitivity and superior in durability by incorporating a specified disazo pigment as an electrostatic charge generating substance and at least one of three specified kinds of compds. as a charge transfer substance in a photosensitive layer. CONSTITUTION:A compd. used as a charge generating layer is represented by formula I in which A1 is a group of formula II or the like; X is an atomic group necessary to form an optionally substd. aromatic ring or hetero ring condensed with a benzene ring; Y is -CON(R<4>, R<5>) or -COOR<5>; R<4> is H, alkyl, or the like; and R<5> is alkyl or an optionally substd. aromatic or hetero ring. A compd. used as a charge transfer substance is represented by any of formulae III, IV, and Vin which R<6> is alkoxy or optionally substd. amino; R<7>, R<8> are each H, halogen, alkyl, or the like; R<9> is H, alkyl, or optionally substd. phenyl; R<10>, R<11> are each optionally substd. alkyl or the like; R<12> is 1-4C alkyl or halogen; and A2 is a condensed 5- or 6-membered hetero ring. A photosensitive layer superior in photoconductive characteristics is obtained by incorporating the charge generating substance and the charge transfer substance in the same layer or each in separate layers, respectively to form a laminated layer.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor in which an electrophotographic photosensitive layer containing a charge generating substance and a charge transporting substance is provided on a conductive support.

Conventionally, selenium,
There are inorganic substances such as cadmium sulfide and zinc oxide.

Electrophotography has already been published by Carlson in US Patent No. 227T.
As disclosed in the specification of No. 1, 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 one image exposure is used. 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 with 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) becomes a visible image when the surface is then contacted with a suitable electrometric indicator material, i.e., toner. .

Toner is contained in an insulating liquid or in a dry carrier, but in either case there is no charge or ? It can be deposited on the surface of the electrophotographic photosensitive layer depending on the turn. The layered display material is
Fixing can be accomplished by known means such as heat, pressure, and solvent vapor. Further, one electrostatic latent can be transferred to a second support (for example, paper, film, etc.). Similarly, it is also possible to transfer an electrostatic latent image to a first support and develop it there. 6 Electrophotography is one of the image forming methods that forms an image in this way. .

The basic characteristics required of an electrophotographic photoreceptor in such electrophotography are (1) ability to be charged to an appropriate potential in the dark, and (2) dissipation of charge in the dark. (3) The charge can be quickly dissipated by light irradiation.

Traditionally used! 1. It is true that these inorganic materials have many advantages, but also have a number of disadvantages. For example, Sele/, which is currently widely used, fully satisfies the conditions (1) to (3) above, but the manufacturing conditions are difficult, the manufacturing cost is high, it is not flexible, and it can be processed into a belt shape. It also has disadvantages, such as being difficult to clean, and being sensitive to heat and mechanical damage, so care must be taken when handling it. Valued cadmium and zinc oxide are dispersed in 40-4 flit as a binder and used as electrophotographic photoreceptors, but they have mechanical drawbacks such as smoothness, hardness, tensile strength, and abrasion resistance. Therefore, it cannot be used repeatedly as is.

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, an electrophotographic photoreceptor made of poly-N-vinylcarbazole and 21≠,7-dolinitrofluorene (U.S. Pat.
2J7), poly-N-vinylcarbazole sensitized with pyri-11um base color (@Kosho 4#-2!l, 68
), an electrophotographic photoreceptor whose main component is all organic pigments [JP-A-Kokai Akihiro 7-371≠3], an electrophotographic photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (l Kakei-Kaisho≠7-) 10733
) etc.

Although these organic electrophotographic photoreceptors have improved the mechanical properties and flexibility of the inorganic electrophotographic photoreceptors to some extent, they generally have low photosensitivity and are not suitable for repeated use, so they do not meet the requirements of electrophotographic photoreceptors. It wasn't completely satisfying.

Now, the photoconductive process of an electrophotographic photoreceptor consists of (1) a process of generating charges by exposure, and (2) a process of transporting charges.

(Selenium photosensitive plate is an example of performing (11 and (2) with the same material.) On the other hand, an example of (11 and (2) being performed with different materials is amorphous selenium and poly-N-vinylcarxol). A non-functional i+gauy electrophotographic photoreceptor in which (1) and (2) are performed using different materials expands the selection range of materials and, accordingly, improves the sensitivity and acceptability of the electrophotographic photoreceptor. It has the advantage that electrophotographic properties such as '# potential are improved, and materials convenient for preparing electrophotographic photoreceptor coatings can be selected from a wide range.

Many proposals have been made for such non-functional i',1 type electrophotographic photoreceptors, but only a few of these have been put into practical use, and most of them have some drawbacks. The reality is that we have no choice but to use it.

Moreover, the combination of a charge-generating substance and a charge-transporting substance has not been theoretically handled to date.
The reality is that various combinations are being investigated through trial and error.

An object of the present invention is to provide a 1L photoreceptor with high sensitivity and excellent durability.

Namely, 1. The object of the present invention (1) contains a disazo pigment represented by the following general formula CI as a charge-generating substance, and at least one of the compounds represented by general formulas [■] to (IV'l) as a charge-transporting substance. This could be achieved by using an electrophotographic photoreceptor characterized by containing one of the above.

Ll) In formula (1), AI is ■ ■(,3
Represents an atomic group necessary to form an aromatic MJ or a heterocycle (these rings may be ++;:? ist or unsubstituted) condensed with Zenri, and 几1 is an alkyl group, Represents a phenyl group or a [d-substituted derivative thereof.

R2 represents a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkyl/carboxyl group, an aryloxycarbonyl group, a radical i'i+σ exchange, or an unsubstituted amino group; Represents an aromatic ring group, an Izumi aromatic ring group, or a deity of these.

R4(,- is a hydrogen atom, an alkyl group, a phenyl M i
fc represents these substitutions.

R,7 (IV) H″6 is an alkoxy group, an aralkyloxy group, or an aralkyloxy group.1
t13 "It" stands for unsubstituted or substituted alkyl, phenyl-1V, or 1 or 13 and 1 or 14 are linked and represent an oxygen ring containing a nitrogen atom. represents a group capable of forming , and R14 and R14 may be rotated or different from each other.

R7 and {circle around (,8) may be the same or different groups and represent a hydrogen atom, a halogen atom, an alkyl group or a lower alkogine group.

R9 represents a hydrogen atom, an alkyl group, an unsubstituted group or a phenyl group having a substituent.

R10, ■"&:t each unsubstituted or substituent carbon J, straight chain or branched alkyl group with 7 to 7 atoms, unsubstituted or substituent carbon number 7 to 20 linear or branched aralkyl groups, or hydrogen atoms of a fused polycyclic aromatic hydrocarbon of the formula 1, 17 (formula or 1 ring number 2 to 1) having no 1d or 1θ substituent ' 11M represents a heptavalent group (aryl group) excluding 1, and R and R may be the same or different from each other.

H and 12 represent an arulyl group having a carbon number of 1 to 1, or a halogen atom.

A2 represents a fused hetero jp ring or a fused two-membered hetero ring represented by the following structural formula; 1゜Zl and Z2 may be the same f=Jt or different atoms<, s, o, N-1 (, CF, , represents an alkyl group having 1 to 0 carbon atoms).

B 15 is a hydrogen atom, an alkyl group, an aralkyl group, an alkoxy group, an aryloxynor, an acyl group, an alkyl group
'/jy represents a sulfonyl group, an aryloxycarbonyl group, a halogen atom, a monoalkylamino group, a dialkylamino group, an amide group or a nitro group.

Regarding the disazo pigment represented by the general formula CI), further =¥L <Description-rZ>.

X is condensed with the benzene ring to which the hydroxyl group and Y are bonded to form an aromatic ring such as a naphthalene/ring anthracene ring or a ring ring such as an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzofurano ring, etc. It is a possible group.

When X is an aromatic ring or a double purple ring system having a cup group,
14 Substituents include a halogen atom (e.g., fluorine atom, chlorine+!L atom, odor atom, etc.), a lower alkyl group, preferably a lower alkyl group with carbon number/~ (e.g., methyl group, ethyl group, propyl group). group, butyl group, impyl group, isobutyl group, etc.), and the number of substituents is 7 or 2, and if there are 2 substituents, they may be the same or different. good.

■Also is an alkyl group, preferably carbon number 1~/2
an alkyl group or a phenyl group.

When R1 is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, inbutyl group, isoamyl group, isoamyl group, neopentyl group, tert-butyl group. You can list basics, etc.

When R1 is an alkyl group, the substituent is a hydroxy group, an alkoxy group with carbon T=4i/~/2, a cyano group, an amino group, an alkylamino group with a carbon number of /~/2, a carbon number/~ Examples include a dialkylamino group having one argyl group of /2, a halogen atom, and an aryl group having t to /2 carbon atoms. Examples include hydroxyalkyl groups (e.g., hydroxymethyl, co-hydroxyethyl, 3-
hydroxypropyl group (1,2-hydro dipropyl group, etc.), alkoxyalkyl group (for example, methoxymethyl group).

Comethoxyether group, 3-methoxypropyl group.

ethquinmethyl group, 2-ethoxyethyl group, etc.), cyanoalkyl group (e.g., cyanmethyl group, λ-cyanoethyl group, etc.), aminoalkyl group (e.g., aminomethyl group, co-aminoethyl group, 3-aminopropyl group, etc.), (
alkylamino)alkyl% (9jl is (methylamino)methyl group, λ-(methylamino)ethyl group, (
ethylamino)methyl4), (dialkylamino)alkyl group (e.g., (dimethylamino)methyl group, 2-(
dimethylamino) methyl group, etc.) % halogenoalkyl group (
Examples include fluoromethyl group, chloromethyl group, bromomethyl group, etc.) and aralkyl groups (eg, benzyl group, phenethyl group, etc.).

R is a plane] Diphenyl group, substituents include hydroxy group, alkoxy group with carbon number / ~ /, 2, cyano group, aminonor, alkylamino group with carbon number 1 ~ 7.2, charcoal,
; a dialkylamino group having two argyl groups of /~/2, a halogen atom, an alkyl group having 1 to 2 carbon atoms, and nitro$. An example! : hydroxyphenyl group, alkoxyphenyl'Q (HJeu, methoxyphenyl group, etoxyphenyl group, etc.), anophenyl group, aminophenyl group=i+4. (Alkylamino)phenyl! (e.g., (methylamino)phenyl group, (ethylamino)phenyl group, etc.), (dialkylamino)phenyl group (e.g., dimethylamino)phenyl group, etc.), halochenophenyl group (e.g., fluorophenyl group, chlorophenyl group, etc.) bromophenyl group, etc.), alkylphenyl groups (for example, tolyl group, ethylphenyl group, cumenyl group, quinryl group, mesityl group, etc.), nitrophenyl group, and substituents thereof (which may be the same or different from each other).

) can be substituted with -2111'j or with three substituents (the positional relationship between the substituents at position 1 or a plurality of the substituents is arbitrary).

■ Examples include a hydrogen atom, a lower alkyl group with a carbon number of /~B, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group that has all alkoxy groups with a carbon number of /~/2, and an aryloxy group with a carbon number of 6 to 20. A 1γ-aryloxycarbonyl group and a 1α-substituted or unsubstituted amino group are preferred.

When R2 is a substituted amino group, specific examples include methylamino group, etelamino group, propylamino group, phenylamino group, tolylamino group, benzylamino group, phenethylamino group, dimethylamino group, 4-dienylamino group, diphenylamino group. etc. can be given.

When R2 is a lower alkyl group, specific examples include a methyl group, an ethyl group, a propyl group, and a butyl group.

Examples include inpropyl group and isobutyl group.

When 几2 is an alkoxycarbonyl group, specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propoquinecarbonyl group, a butoxycargenyl group, an impropoxycarbonyl group, a benzyloxycarbonyl group, and the like.

When R2 is an aryloxycarbonyl group, specific examples include phenoxycarbonyl M and a doareoxycarbonyl group.

It3 and ■(・5 are alkyl groups with up to 20 carbon atoms, aromatic ring groups such as phenyl groups and naphthyl groups, oxygen atoms and nitrogen atoms such as dibenzofuranyl groups, carbazolyl groups, and benzocarbazolyl groups) , a heteroaromatic ring group containing a sulfur atom, or a substituted product thereof.

When 几3sun or 几 is a substituted or unsubstituted alkyl group, the same examples as the substituted or unsubstituted thylkyl group in the above-mentioned ratio can be cited.

When 3 or R is a substituted aromatic group such as a substituted phenyl group, a tσ-naphthyl group, a substituted heteroaromatic group containing a heteroatom such as a substituted dibenzofuranyl group or a substituted carbazolyl group, Examples of groups include hydroxyl group, cyano group, nitro group, halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, etc.), alkyl group with carbon number/~lλ (e.g., methyl group, ethyl group, propyl group, isopropyl group) base, etc.),
Alkoxy with a carbon number of l~/2, $ (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, ba/thyloxy group, impropoxy group, imbutoxy group, inamyloxy group, 1ert-butoxy group, neo pentyloxy group, etc.), amine group, alkylamino group having 1 to 2 carbon atoms (for example, methylamino group, etelamino group, propylamino group, etc.).

A dialkylamino group having 2 to 2 carbon atoms (e.g., dimethylamino group, 7 diethylamine groups, N-methyl-N-etheramino group, etc.), an arylamino group having 6 to 1 carbon atoms (e.g., phenylamino group).

tolylamino group, etc.), an aryl group with carbon number t~/j,
Two diarylamino groups (for example, diphenylamino groups, etc.), carboxyl groups, alkali metal carboxylado groups (examples of alkali metals (cations), Na, K
, Li■, etc.), alkali metal sulfonate groups (eg, alkali gold! f4 (lu ion), Na■, Ni■, Li■, etc.), alkyl carbonyl groups (for example, acetyl group, propionyl group).

benzylcarbonyl group (%), arylcarvinyl group having 1 to 6 carbon atoms (e.g., benzoyl group, toluoyl group, alkylthio group having 7 to 12 carbon atoms),
For example, methylthio group, etherthio group, etc.), or arylthio group having /~/2 carbon atoms (e.g., phenylthio group, tolylthio group, etc.), (the number of substituents is 7 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 are arbitrary. R4 is a hydrogen atom, a carbon number / ~, 200 alkyl groups, phenyl groups, or their combinations.

When R is a substituted or unsubstituted alkyl group or phenyl group, the same groups as the above-mentioned examples of the substituted or unsubstituted alkyl group and phenyl group can be mentioned.

A1 derived from a coupler provides a photoconductive composition or an electrophotographic photosensitive layer with high photosensitivity, and the viewpoint is that a disazo compound can be produced at low cost because the raw material compound for production can be easily obtained. to/1 In addition, as X, a benzene ring, a carbazo/L-ring,
A dibenzofuran ring is preferred, and as Y, compounds represented by general formulas [■] to [IV] will be explained in more detail below.

R6 (1) 7 alkoxy group or (as aralkyloxy group, alkoxy group with carbon number/~7.2, carbon number/
There are ~/, 2 aralkyloxy groups, and specific examples thereof include methoxy group, ethoxy group, propoxy group, butoxy group, octyloxy group, penzyloxy group, and (.

In the case of There is an alkyl group having 1 to 2 carbon atoms.

As a substituent for the alkyl group having a substituent represented by B13 and R14, an alkoxy group having 1-hiro carbon atoms;
Aryloxy group having 6 to 7.2 carbon atoms, hydroxy group,
Examples thereof include an aryl group having t to 12 carbon atoms, a cyano group, and a halogen atom. ■Specific examples of alkyl groups having substituents represented by t13 and H,14 include a)
For example, Metquin methyl.

Alkoxyalkyl such as methoxyether, ethoxymethyl, ethoxyethyl, ethoxypropyl, methoxybutyl, propoquinmethyl, b) phenoxymethyl, phenoxyethyl, naphthoxymethyl, phenoxy is 11-aloxyalkyl such as methyl, C) hydroxymethyl , hydroxyethyl, hydroxypropyl, hydroxyoctyl.

d) aralkyl such as benzyl, phenethyl, ω, ω-diphenylalkyl% e)
Preferred are cyanoalkyls such as cyanomethyl, cyanoethyl, cyanopropyl, abutyl, and octyl, and f) haloalkyls such as chloromethyl, bromomethyl, chloroether, bromopentyl, and chlorooctyl.

The phenyl group represented by B 13 and B 14 is (
Specific examples of the 1a substituent in the case of a phenyl group which may have a substituent and have a W substituent include a) carbon number/~7
．． 2 alkyl group, b) alkoxy group with carbon number 1,
C) an aryloxy group with carbon number t to 7, d) carbon number 2 to
acyl group, e) an alkoxycarbonyl group with a carbon number of λ~, lt, f) a halogen atom, g) a monoalkylamino group substituted with a carbon alkyl group, h) a carbon number of 7~ Examples include an alkyl group such as a butydialkylamino group, 1) an amide group having 2 to 1 carbon atoms, and J) a nitro group.

a) As an alkyl group with carbon number/~/2, methyl group, eternol, linear or branched propyl group, butyl group, pebyl group, hexyl M, b) As an alkoxy group with carbon number/~/2 Methoxy group, etochyne group, propochyne group, butoquinog, c>AIJ-Luo*'/group as phenoxy group, 0-1In- or p-hlyloxy group, d) as acyl group, acetyl group, propionyl group,
Benzoyl group, 〇-1m- or p-toluoyl group, e
) As an alkoxycarbonyl group having 2 carbon atoms, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group.

f) As a halogen atom, chlorine atom, bromine p, or fluorine atom 1g) As a monoalkylamino group substituted with an alkyl group having from 1 to 3 carbon atoms, methylamino group, ethylamino group, butylamino group, h) Number of carbon atoms Dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group% N-methyl-N-ethylamino group, i) as a dialkylamino group substituted with / to ≠ alkyl group;
As an amide group, an acetamide group, a propionamide group,
D Other substituents include a nitro group.

The heterocycle formed by connecting R13 and R14 is preferably a heterocycle represented by the following structural formula.

As B 6 , a 1d”ψ amino group is preferable, and Bl
Substituted amino groups are preferred when 3 and 14 are methyl, ether, benzyl, phenyl, or tolyl groups. In particular, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, N
-Menal-N-phenyl-termino group.

Substitutions such as p-ethyl-N-phenylamino groups are particularly preferred.

H5' and ■(,8 are water mantle atoms; chlorine atoms,
Bromine atom, fluorine atom, etc.)・Rogen atom: Number of carbon atoms such as methyl, ethyl group, propyl group, butylene group, etc. / - Hiro's alkyl group; Number of carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, etc. /~≠ alkoxy groups, etc. Among them, hydrogen atoms, methyl groups, methoxy groups, etc. are preferred.

Specific examples of 几9 include hydrogen atoms: methyl group, ethyl group,
Examples include alkyl groups having a carbon number of /~≠ such as propyl J, I'-, butyl groups, and phenyl groups with or without substituents. The phenyl group having a substituent k is the same as the phenyl group having a substituent represented by the above-mentioned LJR. Preferred among R are water red atom, methyl group, ethyl group, phenyl group, p-(cy)
thylamino) phenyl group.

When BIO and R11 are unsubstituted alkyl groups, specific examples thereof include methyl group, ethyl group, propyl group, butyl group,
Pentyl group, hexyl group, octyl group.

Nonyl group, dodecyl group, isopropyl group, isobutyl group, isopentyl group, and ≠-methyl include butyl group, 5ec-butyl group, and tert-butyl group.

In the case of an alkyl group having a substituent, specific examples of the substituent include salt, bromine, fluorine as a chlorine atom, methoxy group, ethquine group, propoxy group, butoxy group, pentyloxy group, etc. as an alkoxy group. - as a phenoquine group, O-tolyloxy group, m-tolyloxy group, p-tolyloxy group, l-naphthyloxy group,
2-naphthyloxy group, dialkylamine group as dimethylamino group, diethylamino group, dipropylamino group, hemethyl-N-etheramino group, N-etherubepropylamino group, N-methyl-N-propylamino group, alkylthio group , methylthio, ethylthio, propylthio, and N-containing hezoloneclyl groups include piperidino, /-piperazinyl, morpholino, and /-pyrrolidyl groups. An alkyl group in which any of these substituents is bonded to at least/any carbon atom of the aforementioned alkyl group is an example of an alkyl group having a 1a substituent.

When R'', 1( is an unsubstituted aralkyl group, specific examples include be/zyl group, phenethyl group, l-s7tylmethyl group, λ-naphthylmethyl group, /-anthrylmethyl group,
It has a benzhydryl group. In the case of an aralkyl group having a substituent, specific examples of the substituent include the above-mentioned substituents, and one of these groups is bonded to at least one carbon atom of the above-mentioned aralkyl group. This is an example of an aralkyl group having a substituent.

0 When R and R are unsubstituted aryl groups.

Specific examples thereof include phenyl group, /-naphthyl group, λ-naphthyl group, anthryl group, pyrenyl group, acenaphthynyl group, and fluorenyl group. When the aryl group is placed, the above-mentioned d-
Sakaki group and other alkyl groups.

There are methyl group, ethyl group, propyl group, butyl group, pentyl group, isopropyl group, isobutyl group, and isopentyl group, and at least one of these 11-substituted groups is bonded to the carbon atom of the above-mentioned aryl group. This is an example of an aryl cancer in which the aryl group has a substituent.

Among 0 RlR, preferable groups include a phenyl group on one side and a methyl group, an ethyl group, a be/zyl group, or a phenyl group on the other side.

Specific examples of B 12 include a methyl group, an ethyl group, and a propyl group as an alkyl group having 7 to 7 carbon atoms.

There are isobutyl group and tert-butyl group.

Furthermore, examples of the halogen atom include a fluorine atom, a bromine atom, and an iodine atom.

Among the compounds represented by the general formulas i) to (IV), the compound represented by the general formula (II) is preferable ◎ More preferably, in the compound of the general formula (11), 几7, R8 and几9 is a hydrogen atom, and one of BIO and H, 11 is a phenyl group, the other is a methyl group, phenyl group, benzyl group, or ethyl group, and R6 is N,
Specific examples of A1 of the disazo pigment represented by N-diphenylamine general formula CI) are shown in Table n'S 7.

[■]

Specific examples of charge transport materials represented by the general formulas [,11) to [1v]! is shown below.

B -(11 -121 -1al B -(41 CH3 B -(sl B -(++1 B -i71 [U-(8) -t91 113 B -(IOl B -+E B -((support) B -1 Country l bow l B - (141 13-(strip B -t161 B-(1η B -f181 B - stab B-(4 B-(2) l B -((goods) B -i■ B -(wandering 13-1 Sea bream B -i Jun l-13 B-i ■ [3-(4) The photographic photoreceptor of the present invention contains the disazo compound represented by the general formula (1) /p+ or two or more Electrophotographic photoreceptors in the form of various rods are known, but the electrophotographic photoreceptor of the present invention may be any type of photoreceptor; however, it is generally exemplified below. It has a type of electrophotographic photoreceptor structure.

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

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

The disazo compound of the present invention acts as a phototetraelectric substance, and when it absorbs light, it generates charge carriers with extremely high efficiency.The generated charge carriers can also be transported using the disazo compound as a medium, but the charge tB It is even more effective to transport the body-hollowing compound as a vehicle.

In order to prepare an electrophotographic photoreceptor of type (1), fine particles of a disazo compound are dispersed in a solution containing a charge carrier transporting compound and a binder, and the dispersion is coated on a conductive support and dried. The thickness of the electrophotographic photosensitive layer at this time was 3
~30μ, preferably! ~20μ is good.

To create an electrophotographic photoreceptor of type (2), a disazo compound is vacuum-deposited on a conductive support, or dissolved in a solvent such as amine and coated, or fine particles of a disazo compound are coated on a conductive support with a suitable solvent or If necessary, after dispersing the binder in a solvent and coating and drying, a solution containing the charge carrier transport compound and the binder is coated and dried in step 1.7. At this time, the thickness of the disazo compound layer which becomes the charge carrier generation layer is ≠ μ or less, and the necking mechanism is λ
The thickness of the charge carrier transport medium layer is preferably 3 to 30 μm.
, preferably j-20μ.

The disazo compound used in the photoreceptors of types (1) and (2) is used after being ground to a particle size of jtt or less, preferably 2 μm or less, using a dispersing machine such as a ball mill, sand mill, or vibration mill.

If the amount of the disazo compound used in the type (1) Seiko photographic photoreceptor is too small, the sensitivity will be poor; if it is too large, the charging property will be poor, the strength of the electrophotographic photosensitive layer will be weakened, and the electrophotographic The ratio of the disazo compound in the photosensitive layer to the binder is 0.0/~-211f bone times,
The ratio of the charge Ju body transport compound to the binder is preferably 0.0j to 0.0 times the weight. /~2 times the weight,
Preferably, the range is 0.3 to 3 times by weight.

Further, when forming a disazo compound-containing layer which becomes a charge carrier generation layer in the electrophotographic photoreceptor of type (2),
The amount of disazo compound to be used relative to the binder resin is 1 times or more by weight, and if it is less than that, sufficient photosensitivity cannot be obtained. The ratio of the charge conjugate transport compound in the cargo carrier transport medium is 0.2 to λ K times, preferably 0 to ζ inder.
．． 3 to 3 times the weight is preferred.

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 conductive supports used in the electrophotographic photoreceptor of the present invention include metal plates such as aluminum, steel, and lead, plastic materials such as polyester, and plastic films coated with 4-electrode materials such as aluminum and 8N02.
Alternatively, dispersion coating or conductive treated paper may be used.

Examples of the binder include condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polyketone, and polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polycrylamide. Any insulating and adhesive resin can be used.

Biphenyl and chlorinated biphenyl are used as plasticizers.

0-terphenyl, P-terphenyl, cyphthyl phthalate, dimethyl glycol phthalate, diocthyl phthalate, triphenyl s acid, methylnaphthalene, benzophenone, chlorinated/ξ mirafin polypropylene,
Polystyrene, dilaurylthiodipropionate, 3,
Examples include 5-dinitrosalicylic acid and various fluorohydrocarbons.

In addition, in order to improve the surface quality of the TL photographic A photoreceptor,
You may also add gold such as silicone oil.

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

An adhesive layer or barrier layer can be provided between the conductive support and the photosensitive layer, if desired. The material used for these layers is polyamide.

The thickness of the layers of nitrocellulose and aluminum oxide is preferably 7 μm or less.The electrophotographic photoreceptor of the present invention has been described in detail above.The electrophotographic photoreceptor of the present invention generally has low sensitivity and low durability. The electrophotographic photosensitive layer of the present invention can be widely applied to electrophotographic copying machines as well as photoreceptors for printers that use lasers and cathode ray tubes as light sources. .

The photoisoelectric composition containing the disazo 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 that perform 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, A, ,1(.

Ghosh, Tom, Feng, J, Al) pl, ph
ys.

Geta (/, 2)! As described in 9, 2(/97.r) & C, it can also be used as a light guide layer of a solar cell.

The shredded charge-generating substance represented by the general formula (1) and the charge-transporting substance represented by the general formulas [11) to [IV] of the present invention were prepared in a quantity BF337-/7/12, JP-A No. Akihito
Ma-7ri No. 063, Tokukai Showa 6! -/17230 publications, Q! As disclosed in Japanese Patent No. 71, it is dispersed in an alkali-soluble resin solution such as a phenol resin, coated on a conductive support such as aluminum, dried, and subjected to image exposure, toner development, Etching with aqueous alkaline solutions not only allows printing plates with high resolution, high durability, and high sensitivity to be obtained, but also enables the creation of printed circuits.

Next, the present invention will be specifically explained using actual examples, but the present invention is not limited to these examples. In addition, "part" in the examples indicates "heavy part". Example 1 Disazo pigment, compound & A-/J part and polyester resin l
it: (Part name Pyro/200. Manufactured by Toyobo R19)! After dispersing in a ball mill for 20 hours with a solution of 411 parts of tetracracked polyethylene terephthalate, a wire round rod was used to deposit Fluminilum on the surface 1 of a polyethylene terephthalate film of 7jam. Something planned.

Surface electricity4. [(Anti-1O3Ω) was coated and dried to prepare a charge generation layer having a thickness of /am. .

Next, a charge transport material is applied on the charge generation layer, and a compound door B-t3 is applied.
．． 1 part of polycarbonate to bisphenol and 13.3 parts of dichloromethane.

A solution in which 2 tons of Kodichloroethane was dissolved was coated using a wire round rod 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 electrophotographic photoreceptor was charged with +00 VVC by corona discharge of 10 KV using a IL viewing paper tester (SP-G2R type manufactured by Kawaguchi Electric), and then charged with a color temperature of 30,000 ■ In the evening, the source is irradiated with a Gesten lamp so that its surface becomes kerosene, and the time required for the surface potential to decay to half of the initial surface potential is halved: E5'.

(Lux, 5ec) Ih++ w and it was 2.4!
-(IJl, +x.

5ec). The λ process of charging and exposure was performed for 3000
After repeating the test several times, E5o hardly changed.

Examples 2 to 33 As a disazo pigment, instead of the compound iK A -/,
Electrophotography was carried out in exactly the same manner as in Example 1, except that the compounds shown in Table 2 were used as a charge-transmitting substance (-) in place of compound AB-A, and the compounds shown in Table 2 were used. A photoreceptor was created.

Each photoconductor was subjected to a half-exposure dose using the same method as in Example 1.
111 was established.

The results are shown in Table 1.

As can be seen from Table 2 Tatsugai-2, the electrophotographic photoreceptor of the present invention includes:
Comparative Examples 1 to 3 In place of Compound &6 as a charge transport substance, the following comparative compounds were used.
I: A secondary photoreceptor was prepared and the half-decreased amount of light was measured. The results are shown in Table 3.

Comparative Compound C-/-2-3 Table 3 Example 34° disazo pigment compound jFak//part, charge transport substance compound AB A 3 parts, polyester resin (trade name Byron, 100 Toyobo Tonden) 3 parts Add this to 9j parts of dichloromethane, grind and mix this in a ball mill to prepare a solution, and apply this e-cloth solution to a wire round iron for 7.1 minutes to a shim electrically impregnated support (100 mm). An indium oxide vapor film is provided on the surface of a polyethylene/7-dephthalate film.
> Dry the cloth.

Thickness aril single layer type 'ii1. Electrophotographic photoreceptor having a light layer 'r: f; l'l: Liu 1. Ta.

Regarding this electrophotographic 1μ light body, electrostatic copying paper test sandwich (
+s K using Kawaguchi 4 machines (Kasei, 5P-φ2r type)
The corona discharge of Take your time and let it fade.The amount of light E5G (Lux, 5
When measuring ec), <', ! (, Tiux
-5ec). 411 electric light path 2 steps 3θO
b5o after O-turning lζ also hardly changed.

Patent Applicant 'd± Photographic Film Co., Ltd. Procedural Amendment Showa, 11//Month//Date 1, Incident Display Showa! Patent Application No. 12J'--J No. 2
, Title of the invention Electrophotographic photoreceptor 3, Relationship to the case of the person making the amendment Appointment of patent applicant Location 210 Nakanuma, Minamiashigara City, Kanagawa Prefecture Name (52)
0) Fuji Photo Film Co., Ltd. 4. Subject of amendment 1. Detailed explanation of the invention in the specification" Column 5. Self-answer and amendment.

2) ≠ page 7, line 73 "7 parts by weight" "007 parts by weight" and correct it.

Claims (1)

[Scope of Claims] An electrophotographic photoreceptor comprising a photosensitive layer provided on a conductive support, which contains a disazo pigment represented by the following general formula (1) as a charge-generating substance, and has the general formulas □[11) to [ IV
) An electrophotographic photoreceptor comprising at least one compound represented by the following as a charge transporting substance. ] CI) [In Formula 13, A1 is 3 X is an aromatic ring or a heterocyclic ring condensed with the benzene ring in the above formula to which the hydroxyl group and Y are bonded (these rings may be substituted or unsubstituted) ), R1 represents an alkyl group, a phenyl group, or a substituent thereof, and R2 represents a hydrogen atom, a lower alkyl group, a carbamoyl group, a carboxyl group, an alkoxycarboxyl group. , represents an aryloxycarbonyl group, an unsubstituted or unsubstituted amino group. R3 and R5 represent an alkyl group, an aromatic ring group, a heteroaromatic ring group, or a substituent thereof; R4 represents a hydrogen atom, an alkyl group, a phenyl group; and ta represents a substituent thereof. 1 and 7 [■] ■ and 6 are alkoxy threads and aralkyloxy groups. i
t 13 and 1t14 represent an unsubstituted or substituted alkyl group or phenyl group, or 13 and 14 represent a group that can be linked to form a nitrogen atom-containing heterocycle; 4 may be the same or different from each other. 几7 and R may be the same or different groups, and represent a hydrogen atom, a halogen atom, an alkyl group, or a lower alkoxy group. R9 is a hydrogen atom, an alkyl group , represents a phenyl group which is unsubstituted or has a substituent. RIO and Bll are straight-chain groups having 1 to 12 carbon atoms which are unsubstituted or have a substituent, f?-, a branched alkyl group, Substituted or substituted straight chain or branched aralkyl group having 7 to 20 carbon atoms, or unsubstituted or unsubstituted monocyclic or ring 0.2
It represents a heptavalent group (aryl group) obtained by removing a hydrogen atom from a condensed polycyclic aromatic hydrocarbon of ≠ to ≠, and R and ≠ may be the same or different from each other. Further, a carbazole ring may be formed. B12 represents an alkyl group with a carbon number of ~g, or a logen atom. A2 represents a fused j-membered hetero ring or a fused condensate 2-membered ring represented by the following structural formula. Z and A2 may be the same or different atoms, and represent s, o, N I (, 16 (n 16 is an alkyl group with a carbon number of 1 to 1). 1415 is a water zero atom, an alkyl group , an aralkyl group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a halogen atom, a quinoalkyl amino group, a dialkylamino group, an amide radical, or a nitro group.