Naphthylenediamine derivative and electrophotosensitive material using the same

BACKGROUND OF THE INVENTION
The present invention relates to a novel naphthylenediamine derivative which is suitably used as an electric charge transferring material, particularly hole transferring material in applications such as solar battery, electroluminescent device, electrophotosensitive material, etc., and an electrophotosensitive material using the same, which is used for image forming apparatuses such as electrostatic copying machine, laser beam printer, etc.
As the electric charge transferring material to be used for the above applications, there have been known various organic compounds such as carbazole compound, oxadiazole compound, pyrazoline compound, hydrazone compound, stilbene compound, phenylenediamine compound, benzidine compound, etc.
These electric charge transferring materials are normally used in a state where they are dispersed in a membrane of a suitable binding resin. In case of electrophotoconductor, for example, so-called organic photoconductor (OPC) such as single-layer type photoconductor comprising a single-layer type photosensitive layer wherein the above electric charge transferring material and an electric charge generating material which generates an electric charge due to light irradiation are dispersed in a binding resin, multi-layer type photoconductor comprising an electric charge transferring layer containing the above electric transferring material and an electric charge generating layer containing an electric charge generating material, etc. are normally used.
Such an organic photoconductor has an advantage that it is easily produced in comparison with an inorganic photoconductor using an inorganic semi-conductor material and can select its material from electric charge generating material, electric charge transferring material, binding resin, etc., thereby offering a great degree of freedom for design of performance.
Typical examples of the electric charge transferring material include an m-phenylenediamine derivative represented by the general formula (71): ##STR2## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent or an aryl group which may contain a substituent; R.sup.10a, R.sup.10b, R.sup.10c and R.sup.10d are same or different and indicate a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent or an aryl group which may contain a substituent; and f, g, h and i are the same or different and indicate an integer of 1 to 5.
The above m-phenylenediamine derivative is superior in compatibility with binding resin and also superior in electric charge transferring capability. However, the m-phenylenediamine derivative has a problem that it is insufficient in stability and is liable to be deteriorated or decomposed when it changed into a singlet excited state where a reactivity is high due to light irradiation.
The reason is that electrons at a HOMO (Highest Occupied Molecular Orbital) level, which have relation to transferring of holes, are localized on carbons at the 4- and 6-positions of the benzene ring, which constitute a center skeleton of the molecule, thereby increasing a chemical reactivity of these positions.
Therefore, the electrophotosensitive material using the above m-phenylenediamine derivative as the electric charge transferring material has a problem that the m-phenylenediamine derivative causes a photochemical reaction in case of repeating processes of charging, exposure and discharging to form a deteriorated substance, which causes the deterioration of sensitivity and increase in charging, which results in insufficient durability.
SUMMARY OF THE INVENTION
It is a main object of the present invention is to provide a novel electric charge transferring material which is superior in electric charge transferring capability, compatibility with binding resin and stability.
It is another object of the present invention to provide an electrophotosensitive material using the above electric charge transferring material, which has a high sensitivity and an excellent durability.
The present inventors have studied to improve the stability of the material by introducing a naphthalene ring having a quenching effect, i.e. effect of accelerating deactivation from a photoexcited state in place of a benzene ring constituting a center skeleton of the above phenylenediamine derivative, and then carried out a molecular designing of the naphthylenediamine derivative as a novel compound.
As a result, it has been found that, when two 6-membered rings constituting the naphthalene ring are respectively substituted with one nitrogen atom, the resulting derivative is inferior in compatibility with binding resin because a symmetry of the molecule is high and, furthermore, the resulting derivative has low electric charge transferring capability, resulting in being unsuitable for practical use.
Therefore, the present inventors have further studied about the position where naphthalene rings are substituted with two nitrogen atoms. As a result, it has been found that a naphthylenediamine derivative represented by the general formula (1): ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent or an aryl group which may have a substituent; R.sup.5a, R.sup.5b, R.sup.5c, R.sup.5d, R.sup.5e and R.sup.5f are same or different and indicate a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group which may have a substituent, an alkoxy group which may have a substituent or an aryl group which may have a substituent; and a, b, c and d, which respectively indicate substituting numbers of the groups R.sup.1, R.sup.2, R.sup.3 and R.sup.4, are the same or different and indicate an integer of 1 to 5, has the following features.
(1) Since an asymmetry of the molecule becomes higher, the compatibility with binding resin is the same as that of the m-phenylenediamine derivative or it becomes higher.
(2) Regarding the above naphthylenediamine derivative, electrons at the HOMO level, which have relation to transfer of holes, are non-localized to spread through the molecule because of the following two main factors:
1 four phenyl groups substituted on the respective nitrogen atoms are located close each other, and
2 electrons at the HOMO level in the center naphthalene ring are not localized like the benzene ring, and they are liable to spread through the ring, which results in non-localization. As a result, the mobility of the electric charge becomes better than that of the m-phenylenediamine derivative in cooperation with the fact that the naphthalene ring has a .pi. electron conjugate system larger than that of the benzene ring. Therefore, the electric charge transferring capability is further improved.
(3) As described above, regarding the naphthylenediamine derivative wherein electrons at the HOMO level are non-localized, a stereoscopic distribution of electrons is in a plane. Therefore, when this naphthylenediamine derivative as the electric charge transferring material is contained in the photosensitive layer of the electrophotosensitive material, together with an electric charge generating material, an interaction with the electric charge generating material, i.e. action of drawing an electric charge (particularly, hole) generated in the electric charge generating material becomes strong to improve the electric charge generation efficiency of the electric charge generating material. As a result, the sensitivity of the photosensitive material is improved.
(4) As described above, the naphthylenediamine derivative wherein electrons at the HOMO level are non-localized has not a position where electrons are localized to enhance a chemical reactivity, like the center benzene ring in the m-phenylenediamine derivative. Therefore, the stability at the time of light irradiation becomes excellent in cooperation with the fact that the center naphthalene ring has a quenching effect as described above. Thus, the present invention has been accomplished.
That is, the naphthylenediamine derivative of the present invention is characterized by being represented by the above general formula (1).
Also, the electrophotosensitive material of the present invention is characterized by providing a photosensitive layer containing the above naphthylenediamine derivative (1) on a conductive substrate.
Furthermore, the present inventors have found that it becomes possible to impart a high sensitivity to the photosensitive material and to improve the durability thereof by containing at least one selected from the following compounds represented by the general formulas (2), (3), (4), (5) and (6).
2,4,7-trinitrofluorenonimine derivative represented by the general formula (2): ##STR4## wherein R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent, an aryl group which may contain a substituent, an aralkyl group which may contain a substituent or a phenoxy group which may contain a substituent.
Diphenoquinone derivative represented by the general formula (3): 0 ##STR5## wherein R.sup.F, R.sup.G, R.sup.H and R.sup.I are same or different and indicate a hydrogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent, an aryl group which may contain a substituent or an aralkyl group which may contain a substituent.
Ethylated nitrofluorenonimine derivative represented by the general formula (4): ##STR6## wherein R.sup.J, R.sup.K, R.sup.L, R.sup.M and R.sup.N are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent, an aryl group which may contain a substituent, an aralkyl group which may contain a substituent or a phenoxy group which may contain a substituent; and .alpha. is an integer of 1 to 4.
Tryptoanthrine derivative represented by the general formula (5): ##STR7## wherein R.sup.O and R.sup.P are same or different and indicate an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent or a nitro group; and .beta. and .gamma. are the same or different and indicate an integer of 0 to 3.
Tryptoanthrinimine derivative represented by the general formula (6): ##STR8## wherein R.sup.Q, R.sup.R, R.sup.S, R.sup.T and R.sup.U are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent, an aryl group which may contain a substituent, an aralkyl group which may contain a substituent or a phenoxy group which may contain a substituent; and .delta. is an integer of 1 to 4.
Another electrophotosensitive material of the present invention is characterized by providing a photosensitive layer containing the naphthylenediamine derivative (1) and 2,4,7-trinitrofluorenonimine derivative (2), a photosensitive layer containing the naphthylenediamine derivative (1) and diphenoquinone derivative (3), a photosensitive layer containing the naphthylenediamine derivative (1) and ethylated nitrofluorenonimine derivative (4), a photosensitive layer containing the naphthylenediamine derivative (1) and tryptoanthrine derivative (5) or a photosensitive layer containing the naphthylenediamine derivative (1) and tryptoanthrinimine derivative (6) on a conductive substrate.
Normally, when a hole transferring material and an electron transferring material are contained in the same layer, both materials forms a charge transfer complex to cause deterioration of the electric charge transferring capability of the whole photosensitive layer, which results in deterioration of the sensitivity of the photosensitive material.
However, in case of combination of the naphthylenediamine derivative (1) (hole transferring material) with the 2,4,7-trinitrofluorenonimine derivative (2), diphenoquinone derivative (3), ethylated nitrofluorenonimine derivative (4), tryptoanthrine derivative (5) or tryptoanthrinimine derivative (6), all of which are electron transferring materials, no charge transfer complex is formed in the layer even if both transferring materials are contained in a high concentration at which holes and electrons are efficiently transferred. Therefore, it shows such an unusual action that the hole transferring material and electron transferring material can efficiently transfer holes and electrons, respectively.
Therefore, the efficiency of electrons, which are remained as a trap of holes in the photosensitive layer, to be charged from the photosensitive layer is improved and the residual potential is lowered, thereby improving the sensitivity of the photoconductor. As described above, the generation of the trap is prevented so that an increase in charging (increase in surface potential and residual potential) is not generated when the image is repeatedly formed, and the durability of the photosensitive material is improved.
It also became apparent that a photosensitive material containing the naphthylenediamine derivative (1) and any one of the above five sorts of electron transferring materials has a specific action, i.e. particularly excellent light resistance to ultraviolet light.
That is, when ultraviolet light is irradiated to the photosensitive material, the naphthylenediamine derivative (1) becomes a singlet excited state where a reactivity is high, and is liable to be deteriorated or decomposed. However, when any one of the above five sorts of electron transferring materials is present in the same layer, these derivatives having excellent electron acceptive properties show a quenching effect, i.e. effect of accelerating deactivation from a photoexcited state. Therefore, deterioration of the material and formation of a radical are inhibited, thereby improving the light resistance.
Particularly, this effect is remarkably observed in the 2,4,7-trinitrofluorenonimine derivative (2), however, it is also observed in other four sorts of electron transferring materials. It is assumed that a specific chemical structure in the respective materials (e.g. imine skeleton, in case of 2,4,7-trinitrofluorenonimine derivative (2)) affords this effect, but a definite mechanism thereof has never been apparent.
Furthermore, the present inventors have found that it becomes possible to impart a higher sensitivity to the photosensitive material and to improve the durability thereof by blending a phenylenediamine derivative represented by the general formula (7): ##STR9## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are same or different and indicate a hydrogen atom, a halogen atom, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent or an aryl group which may contain a substituent; R.sup.10a, R.sup.10b, R.sup.10c and R.sup.10d are same or different and indicate a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group which may contain a substituent, an alkoxy group which may contain a substituent or an aryl group which may contain a substituent; and f, g, h and i are the same or different and indicate an integer of 1 to 5! including the above m-phenylenediamine derivative represented by the general formula (71) into a photosensitive layer containing the naphthylenediamine derivative (1), as is apparent from the Examples described hereinafter, although the mechanism is not apparent.
Also, the present inventors have found that it becomes possible to impart a further higher sensitivity to the photoconductor and to further improve the durability thereof by using the above combination system of the naphthylenediamine derivative (1) and phenylenediamine derivative (7) (both are hole transferring materials) in combination with any one of the above five sorts of electron transferring materials, because of the effect due to the above two sorts of hole transferring materials and effect due to the combination of the above-described hole transferring material and electron transferring material.
Accordingly, another electrophotosensitive material of the present invention is characterized by providing a photosensitive layer containing the naphthylenediamine derivative (1) and phenylenediamine derivative (7) and, if necessary, at least one of the above five sorts of electron transferring materials on a conductive substrate.

BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a graph illustrating the results of infrared spectroscopic analysis of the naphthylenediamine derivative of Example 1 according to the present invention.
FIG. 2 is a graph illustrating the results of infrared spectroscopic analysis of the naphthylenediamine derivative of Example 3 according to the present invention.

DETAILED EXPLANATION OF THE INVENTION
Examples of the halogen atom corresponding to the groups R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5a to R.sup.5f in the above general formula (1) include fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
Examples of the alkyl group include lower alkyl groups having 1 to 6 carbon atoms, such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, hexyl group, etc.
Examples of the alkoxy group include lower alkoxy groups having 1 to 6 carbon atoms, such as methoxy group, ethoxy group, isopropoxy group, butoxy group, tertiary butoxy group, hexyloxy group, etc.
Examples of the aryl group include phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, o-terphenyl group, etc.
Examples of the substituent with which the alkyl group, alkoxy group and aryl group may be substituted include the above alkyl group, halogen atom, alkoxy group, etc.
The naphthylenediamine derivative wherein the groups R.sup.1 to R.sup.4 and R.sup.5a to R.sup.5e indicate a hydrogen atom, simultaneously, is inferior in compatibility with binding resin in spite of the asymmetry of the above molecular structure. Therefore, it is preferred that the groups R.sup.1 to R.sup.4 and R.sup.5a to R.sup.5e do not indicate a hydrogen atom, simultaneously.
The substituting number of the groups R.sup.1, R.sup.2, R.sup.3 and R.sup.4 defined by the symbol a, b, c and d in the general formula (1) can be optionally selected within a range of 1 to 5, respectively.
In the naphthylenediamine derivative (1) of the present invention, the substitution position of two nitrogen atoms is limited to any one of two 6-membered rings constituting the napthalene ring, as described above. For example, four sorts such as 2,3-naphthylenediamine derivative represented by the general formula (11): ##STR10## 1,2-naphtylenediamine derivative represented by the general formula (12): ##STR11## 1,3-naphthylenediamine derivative represented by the general formula (13): ##STR12## and 1,4-naphthylenediamine derivative represented by the general formula (14): ##STR13## belong to the naphthylenediamine derivative of the present invention (in the above respective formulas R.sup.1 to R.sup.4, R.sup.5a to R.sup.5f and a to d are as defined above).
Among these four sorts of naphthylenediamine derivatives, the 2,3-naphthylenediamine derivative represented by the general formula (11) and 1,3-naphthylenediamine derivative represented by the general formula (13) are particularly preferred.
The former derivative (11) is superior in electric charge transferring capability due to the above effect of non-localization of electrons at the HOMO level because four phenyl groups substituted on two nitrogen atoms are located close each other, and is also particularly superior in stability at the time of light irradiation. In addition, it seemed that such a 2,3-naphthylenediamine derivative (11) has low asymmetry of the molecule in comparison with the 1,3-naphthylenediamine derivative (13). However, the derivative has a right compatibility with binding resin for practical use because a slight torsion is formed in the molecular structure due to a steric hindrance of phenyl groups substituted on two nitrogen atoms and the non-symmetry is enhanced.
Accordingly, regarding the electrophotosensitive material comprising a photosensitive layer containing the 2,3-naphthylenediamine derivative (11), the electric charge generation efficiency in the electric charge generating material is improved because of excellent electric charge transferring capability of the derivative (11) and, at the same time, the residual potential at the time of image formation is lowered and the sensitivity is improved. In addition, the electrophotosensitive material comprising a photosensitive layer containing the 2,3-naphthylenediamine derivative (11) is also superior in durability because of stability of the derivative (11).
Non-limited examples of the 2,3-naphthylenediamine derivative include the compounds represented by the formulas (11-1) to (11-27). ##STR14##
On the other hand, regarding the latter 1,3-naphthylenediamine derivative (13), four phenyl groups substituted on two nitrogen atoms are located separately in comparison with the 2,3-naphthylenediamine derivative (11). However, four phenyl groups are located close each other in comparison with those wherein two 6-membered rings constituting the naphthalene ring is respectively substituted with one nitrogen atom. Therefore, the derivative has a right electric charge transferring capability for practical use and stability at the time of light irradiation due to the effect of non-localization of electrons at the HOMO level. Furthermore, it is particularly superior in compatibility with binding resin because of strong asymmetry of the molecule.
Therefore, the electrophotosensitive material using the above 1,3-naphthylenediamine derivative (13) has the same sensitivity characteristics as those of the derivative using the 2,3-naphthylenediamine derivative (11), and is also superior in durability.
Example of the 1,3-naphthylenediamine derivative include the compounds represented by the formulas (13-1) to (13-26). ##STR15##
The naphthylenediamine derivative (1) of the present invention can be synthesized by various methods. For example, the 2,3-naphthylenediamine derivative represented by the following general formula (11a), wherein the groups R.sup.1 to R.sup.4 indicate the same group R.sup.11, simultaneously, and the substituting number k and position to be substituted on the phenyl group are the same, among the compounds included in the 2,3-naphthylenediamine derivative (11) can be synthesized according to the following reaction scheme.
That is, a 2,3-naphthylenediamine derivative represented by the general formula (1a) is mixed with an iodobenzene derivative represented by the general formula (1b) in a molar ratio of 1:4, together with copper powder, copper oxide or halogenated copper, and the mixture is reacted under the presence of a basic substance to synthesize a 2,3-naphthylenediamine derivative (11a). ##STR16##
In order to synthesize a similar derivative which belongs to the 1,3-naphthylenediamine derivative (13), the same amount of a 1,3-naphthylenediamine derivative represented by the general formula (1c): ##STR17## may be used in place of the 2,3-naphthylenediamine derivative (1a) as a starting material in the above reaction.
In addition, the compound represented by the following general formula (11b), wherein the groups R.sup.1 and R.sup.3 indicate the same group R.sup.12, simultaneously, and the substituting number m and position to be substituted on the phenyl group are the same; the groups R.sup.2 and R.sup.4 indicate the same group R.sup.13, simultaneously, and the substituting number n and position to be substituted on the phenyl group are the same; and the groups R.sup.12 and R.sup.13 are different each other, or the substituting numbers m and n are different or position of the groups R.sup.12 and R.sup.13 to be substituted on phenyl groups are different, among the compounds included in the 2,3-naphthylenediamine derivative (11) can be synthesized according to the following reaction scheme.
That is, an acetylated 2,3-naphthylenediamine derivative represented by the general formula (1d) is mixed with an iodobenzene derivative represented by the general formula (1e) in a molar ratio of 1:2, together with copper powder, copper oxide or halogenated copper, and the mixture is reacted under the presence of a basic substance to synthesize a reaction intermediate represented by the general formula (1f). ##STR18##
Then, this reaction intermediate is deacetylated by reacting with hydrochloric acid etc. in a suitable solvent to give a second intermediate. The obtained second intermediate is similarly reacted with an iodobenzene derivative represented by the general formula (1h) in a molar ratio of 1:2 to synthesize a 2,3-naphthylenediamine derivative (11b). ##STR19##
In order to synthesize a similar derivative which belongs to the l,3-naphthylenediamine derivative (13), the same amount of an acetylated 1,3-naphthylenediamine derivative represented by the general formula (1i): ##STR20## may be used in place of the acetylated 2,3-naphthylenediamine derivative (1d) as a starting material in the above reaction.
The naphthylenediamine derivative of the present invention is suitably used as an electric charge transferring material, particularly hole transferring material in applications such as solar battery, electroluminescent device, electrophotosensitive material, etc., and can also be used in other various fields.
The electrophotosensitive material of the present invention comprises a photosensitive layer containing at least one sort of the above naphthylenediamine derivative (1) on a conductive substrate. The photosensitive layer is classified into two types, i.e. a single-layer type photosensitive layer and a multi-layer type photosensitive layer. The present invention can be applied to both photosensitive layers.
The action and effect of the electrophotosensitive material using the naphthylenediamine derivative (1) as the hole transferring material and, if necessary, phenylenediamine derivative (7) and at least one sort of the above five sorts of electron transferring materials in combination is remarkably observed in the single-layer type photosensitive layer, particularly. In that case, there is an advantage that the resulting photosensitive material can be used for positive and negative charging. However, it is also possible to use it for the above-described multi-layer type photosensitive layer, as a matter of course.
The single-layer type photosensitive layer can be formed by applying a coating solution, which is prepared by dissolving or dispersing at least naphthylenediamine derivative among the naphthylenediamine derivative (1) and phenylenediamine derivative (7) as the electron transferring material, an electric charge generating material and a binding resin and, if necessary, at least one sort of the above five sorts of electron transferring materials in a suitable solvent, on a conductive substrate using a means such as application, followed by drying.
In addition, the multi-layer type photosensitive layer can be formed by forming an electric charge generating layer containing an electric charge generating material on a conductive substrate using a means such as deposition or application. Next, a coating solution containing a naphthylenediamine derivative (1) as an electron transferring material and a binding resin is applied on the electric charge generating layer using a means such as application, followed by drying to form an electric charge transferring layer. To the contrary, an electric charge transferring layer may be formed on a conductive substrate and then an electric charge generating layer may be formed thereon.
In case of multi-layer type photosensitive layer, the electron transferring material is normally contained in the electric charge generating layer, but it may also be contained in the electric charge transferring layer. In addition, the phenylenediamine derivative (7) as the hole transferring material is normally contained in the electric charge transferring layer, together with the naphthylenediamine derivative (1), but it may also be contained in the electric charge generating layer.
Examples of the electric charge generating material include powder of inorganic photoconductive materials (e.g. selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide, .alpha.-silicon), azo pigments, bisazo pigments, perylene pigments, anthanthrone pigments, phthalocyanine pigments, indigo pigments, triphenylmethane pigments, therene pigments, toluidine pigments, pyrazoline pigments, quinacridone pigments, dithioketopyrrolopyrrole pigments, and the like. These electric charge generating materials can be used alone or in combination thereof according to the range of sensitivity of the electrophotosensitive material.
As the electric charge generating material suitable for an organic electrophotosensitive material having sensitivity at a wavelength within a range of not less than 700 nm, for example, there are phthalocyanine pigments such as X-type metal-free phthalocyanine, oxotitanyl phthalocyanine and the like. The electrophotosensitive material using these phthalocyanine pigments as the electric charge generating material and the naphthylenediamine derivative (1) as the electron transferring material has a high sensitivity in the above range of the wavelength. For example, it is suitably used for digital optical system image forming apparatuses such as laser beam printer and facsimile.
On the other hand, as the electric charge generating material which is suitable for the organic electrophotosensitive material having high sensitivity in the visible range, there are azo pigments, perylene pigments, etc. The electrophotosensitive material using these pigments as the electric charge generating material and the naphthylenediamine derivative (1) as the electron transferring material has a high sensitivity in the visible range. For example, it can be suitably used for analogue optical system image forming apparatuses such as electrostatic copying machine, etc.
The naphthylenediamine derivative (1) as the electron transferring material can be used alone or in combination with the 2,4,7-trinitrofluorenonimine derivative (2), diphenoquinone derivative (3), ethylated nitrofluorenonimine derivative (4), tryptoanthrine derivative (5), tryptoanthrinimine derivative (6) or phenylenediamine derivative (7), as described above. Furthermore, it can also be used in combination with other electric charge transferring materials which have hitherto been known.
Examples of the halogen atom, alkyl group, alkoxy group and aryl group, which correspond to the groups R.sup.A, R.sup.B, R.sup.C, R.sup.D and R.sup.E in the above general formula (2) representing the 2,4,7-trinitrofluorenonimine derivative, include the same groups as those described above. In addition, examples of the aralkyl group include benzyl group, benzhydryl group, phenethyl group, etc. As substituents which may substituted on these groups or the naphthyl group, there are the same groups as those described above.
Examples of the 2,4,7-trinitrofluorenonimine derivative (2) include the compounds represented by the formulas (2-1) to (2-20). ##STR21##
Examples of the halogen atom, alkoxy group, aryl group and aralkyl group, which correspond to the groups R.sup.F, R.sup.G, R.sup.H and R.sup.I in the above general formula (3) representing the diphenoquinone derivative, as well as substituents which may be substituted on these groups include the same groups as those described above. Examples of the alkyl group include cyclic alkyl groups such as cyclohexyl group, etc., in addition to the above respective groups.
Examples of the diphenoquinone derivative (3) include the compounds represented by the formulas (3-1) to (3-9). ##STR22##
Examples of the halogen atom, alkyl group, alkoxy group, aryl group and aralkyl group, which correspond to the groups R.sup.J, R.sup.K, R.sup.L, R.sup.M and R.sup.N in the above general formula (4) representing the ethylated nitrofluorenonimine derivative, as well as substituents which may be substituted on these groups or phenoxy group include the same groups as those described above.
Examples of the ethylated nitrofluorenonimine derivative (4) include the compounds represented by the formulas (4-1) to (4-9). ##STR23##
Examples of the alkyl group and alkoxy group, which correspond to the groups R.sup.O and R.sup.P in the above general formula (5) representing the tryptoanthrine derivative, as well as substituents which may be substituted on these groups include the same groups as those described above.
Examples of the tryptoanthrine derivative (5) include the compounds represented by the formulas (5-1) to (5-5). ##STR24##
Examples of the halogen atom, alkyl group, alkoxy group, aryl group and aralkyl group, which correspond to the groups R.sup.Q, R.sup.R, R.sup.S, R.sup.T and R.sup.U in the above general formula (6) representing the tryptoanthrinimine derivative, as well as substituents which may be substituted on these groups or phenoxy group include the same groups as those described above.
Examples of the tryptoanthrinimine derivative (6) include the compounds represented by the formulas (6-1) to (6-11). ##STR25##
Examples of the halogen atom, alkyl group, alkoxy group and aryl group, which correspond to the groups R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10a to R.sup.10d in the above general formula (7) representing the phenylenediamine derivative, as well as substituents which may be substituted on these groups include the same groups as those described above.
The phenylenediamine derivative (7) is classified into three sorts according to the position of two nitrogen atoms to be substituted on the center benzene ring, e.g. o-, m- and p-phenylenediamine derivatives. In the present invention, two sorts of them such as m-phenylenediamine derivative represented by the general formula (71): ##STR26## and o-phenylenediamine derivative represented by the general formula (72): ##STR27## are suitably used (in the above formulas R.sup.6 to R.sup.9, R.sup.10a to R.sup.10d and f to i are as defined above) in view of intensity of an interaction with the naphthylenediamine derivative, compatibility with other materials, electric charge transferring capability, etc.
Examples of the m-phenylenediamine derivative (71) include the compounds represented by the formulas (71-1) to (71-3). ##STR28##
Examples of the o-phenylenediamine derivative (72) include the compound represented by the formula (72-1): ##STR29##
Examples of the other electric charge transferring material which may be used in combination with the above respective electric charge transferring materials include various electron transferring materials and hole transferring materials.
Examples of the electron transferring material among electric charge transferring materials include electron attractive materials such as benzoquinone compound, naphthoquinone compound, malononitrile, thiopyran compound, tetracyanoethylene, tetracyanoquinodimethane, chloroanil, bromoanil, 2,4,7-trinitro-9-dicyanomethylenefluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, dinitrobenzene, dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride, dibromomaleic anhydride, etc., high-molecular compounds obtained by polymerizing the above electron attractive materials, and the like.
Examples of the hole transferring material include electron donative materials such as nitrogen-containing cyclic compounds and condensed polycyclic compounds, for example, diamine compounds other than naphthylenediamine derivative (1) and phenylenediamine derivative (7); diazole compounds such as 2,5-di(4-methylaminophenyl)-1,3,4-oxadiazole, etc.; styryl compounds such as 9-(4-diethylaminostyryl)anthracene, etc.; carbazole compounds such as polyvinyl carbazole, etc.; pyrazoline compounds such as 1-phenyl-3-(p-dimethylaminophenyl)pyrazoline, etc.; hydrazone compounds; triphenylamine compounds; indol compounds; oxazole compounds; isooxazole compounds, thiazole compounds; thiadiazole compounds; imidazole compounds; pyrazole compounds; triazole compounds and the like.
These electric charge transferring materials can also be used alone or in combination thereof. Further, when using an electric charge transferring material having film forming properties such as polyvinyl carbazole, the binding resin is not necessarily required.
Examples of the binding resin include thermoplastic resins such as styrene polymer, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, acrylic polymer, styrene-acrylic copolymer, polyethylene, ethylene-vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, polycarbonate, polyarylate, polysulfon, diaryl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, etc.; crosslinking thermosetting resins such as silicone resin, epoxy resin, phenol resin, urea resin, melamine resin, etc.; photosetting resins such as epoxy acrylate, urethane acrylate, etc. These binding resins can be used alone or in combination thereof.
Additives such as sensitizers, fluorene compounds, ultraviolet absorbers, plasticizers, surfactants, leveling agents, etc. can be added to the photosensitive layer, in addition to the above respective components. In order to improve sensitivity of the electrophotosensitive material, there may be used sensitizers such as tertphenyl, halonaphthoquinones, acenaphthylene, etc. in combination with the electric charge generating agent.
In the multi-layer photosensitive material, the electric charge generating material and the binding resin, both of which constitute the electric charge generating layer, may be used in various proportions. It is preferred that 5 to 1000 parts by weight, particularly 30 to 500 parts by weight of the electric charge generating material is used, based on 100 parts by weight of the binding resin.
The electric charge transferring material and the binding resin, both of which constitute the electric charge transferring layer, can be used in various proportions within such a range as not to prevent the transmission of the electric charge and as to prevent the crystallization of the electric charge transferring material. It is preferred that 10 to 500 parts by weight, particularly 25 to 200 parts by weight of the electric charge transferring material containing the naphthylenediamine derivative (1) is used, based on 100 parts by weight of the binding resin so as to easily transfer the electric charge generated in the electric charge generating layer due to light irradiation. The amount of the electric charge transferring material is that of the naphthylenediamine derivative (1) when the naphthylenediamine derivative (1) is used alone. When using the naphthylenediamine derivative (1) in combination with the other electric charge transferring material, the amount of the electric charge transferring material is the total amount of both derivatives. For example, when using the naphthylenediamine derivative (1) in combination with the phenylenediamine derivative (7), the proportion (weight ratio) of both derivatives is preferably within a range of 20:80 to 80:20 (naphthylene derivative (1):phenylenediamine derivative (7)).
Regarding the thickness of the multi-layer type photosensitive layer, it is preferred that the thickness of the electric charge generating layer is about 0.01 to 5 .mu.m, particularly about 0.1 to 3 .mu.m and the thickness of the electric charge transferring layer is about 2 to 100 .mu.m, particularly about 5 to 50 .mu.m.
In the single-layer type photosensitive material, it is suitable that 0.1 to 50 parts by weight, particularly 0.5 to 30 parts by weight of the electric charge generating material and 20 to 500 parts by weight, particularly 30 to 200 parts by weight of the electric charge transferring material containing the naphthylenediamine derivative (1) are used, based on 100 parts by weight of the binding resin. The amount of the electric charge transferring material is that of the naphthylenediamine derivative (1) when the naphthylenediamine derivative (1) is used alone. When using the naphthylenediamine derivative (1) in combination with the other electric charge transferring material, the amount of the electric charge transferring material is the total amount of both derivatives.
In the system using the hole transferring material such as naphthylenediamine derivative (1), phenylenediamine derivative (7), etc. in combination with the electron transferring material such as 2,4,7-trinitrofluorenonimine derivative (2), diphenoquinone derivative (3), ethylated nitrofluorenonimine derivative (4), tryptoanthrine derivative (5), tryptoanthrinimine derivative (6), phenylenediamine derivative (7), etc., the proportion (weight ratio) of both transferring materials is preferably within a range of 90:10 to 40:60 (hole transferring material:electron transferring material).
Furthermore, in the system using the naphthylenediamine derivative (1) in combination with the phenylenediamine derivative (7), the proportion (weight ratio) of both transferring materials is preferably within a range of 20:80 to 80:20 (naphthylenediamine derivative (1):phenylenediamine derivative (7)).
It is preferred that the film thickness of the single-layer type photosensitive layer is 5 to 100 .mu.m, particularly 10 to 50 .mu.m.
A barrier layer may be formed, in such a range as not to injure the characteristics of the electrophotosensitive material, between the conductive substrate and the electrophotosensitive layer in the single-layer type photosensitive material, or between the conductive substrate and the electric charge generating layer, between the conductive substrate and the electric charge transferring layer or between the electric charge generating layer and the electric charge transferring layer in the multi-layer type photosensitive material. Further, a protective layer may be formed on the surface of the electrophotosensitive material.
As the conductive substrate on which the above respective layers are formed, various materials having conductivity can be used, and examples thereof include metals such as iron, aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, brass, etc.; plastic materials vapor-deposited or laminated with the above metal; glass materials coated with aluminum iodide, tin oxide, indium oxide, etc.
The conductive substrate may be made in the form of a sheet or a drum according to the structure of the image forming apparatus to be used. The substrate itself may have conductivity or only the surface of the substrate may have conductivity. It is preferred that the conductive substrate has a sufficient mechanical strength when used.
When the above respective layer constituting the electrophotosensitive material are formed by a coating method, the electric charge generating material, the electric charge transferring material, the binding resin, etc. may be dispersed/mixed with a suitable solvent by a known method, for example, using a roll mill, a ball mill, an atriter, a paint shaker, a supersonic dispenser, etc. to prepare a coating solution, which is applied by a known means and then allowed to dry.
As the solvent for preparing the coating solution, there can be used various organic solvents, and examples thereof include alcohols such as methanol, ethanol, isopropanol, butanol, etc.; aliphatic hydrocarbons such as n-hexane, octane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, etc.; ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, etc.; ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc.; esters such as ethyl acetate, methyl acetate, etc.; dimethylformaldehyde, dimethylformamide, dimethyl sulfoxide, etc. These solvents may be used alone or in combination thereof.
In order to improve dispersibility of the electric charge transferring material and electric charge generating material as well as smoothness of the surface of the photosensitive layer, there may be added surfactants, leveling agents, etc. to the coating solution.
EXAMPLES
The following Examples and Comparative Examples further illustrate the present invention.
Example 1
Synthesis of N,N,N', N'-tetrakis(3-methylphenyl)-2,3-naphthyenediamine
2,3-Naphthylenediamine (15.8 g) represented by the formula (1A): ##STR30## m-iodotoluene (87.2 g) represented by the formula (1B): ##STR31## potassium carbonate (27.6 g) and copper powder (2 g) were added in 300 ml of nitrobenzene, and the mixture was refluxed while a nitrogen gas was blowing into this reaction system under vigorous stirring for 24 hours. The water content produced in the reaction was removed out of the reaction system by azeotropic distillation with nitrobenzene.
After the reaction solution was cooled, the inorganic substance was filtered off. Further, nitrobenzen was distilled off by steam distillation to give the residue, which was dissolved in cyclohexane. The solution was purified by subjecting to silica gel column chromatography and cyclohexane was distilled off to give a white precipitation. Then, the white precipitation was recrystallized from n-hexane to give the titled compound represented by the above formula (11-2) as an objective product (20.5 g, yield: 39.5%).
The results of the infrared spectroscopic analysis of the above compound are shown in FIG. 1. In addition, the results of the elemental analysis are shown below.
Elemental analysis (%):
Calcd.: C, 87.98; H, 6.61; N, 5.40
Found: C, 87.89; H, 6.66; N, 5.44
Example 2
Synthesis of N,N,N',N'-tetrakis(4-isopropylphenyl)-2,3-naphthylenediamine
According to the same manner as that described in Example 1 except for using 98.4 g of 4-isopropyl-iodobenzene represented by the formula (1C): ##STR32## in place of m-iodotoluene represented by the formula (1B), the titled compound represented by the above formula (11-6) was obtained as an objective product (22.8 g, yield: 35.6%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%),
Calcd.: C, 86.18; H, 9.44; N, 4.37
Found: C, 86.01; H, 9.51; N, 4.47
Example 3
Synthesis of N,N'-bis(3-methylphenyl)-N,N'-bis(3-isopropylphenyl)-2,3-naphthylenediamine
N,N'-diacetyl-2,3-naphthylenediamine (12.1 g) represented by the formula (1D): ##STR33## m-iodotoluene (21.8 g) represented by the above formula (1B), potassium carbonate (13.8 g) and copper powder (1 g) were added in 150 ml of nitrobenzene, and the mixture was refluxed while a nitrogen gas was blowing into this reaction system under vigorous stirring for 24 hours. The water content produced in the reaction was removed out of the reaction system by azeotropic distillation with nitrobenzene.
After the reaction solution was cooled, the inorganic substance was filtered off. Further, nitrobenzen was distilled off by steam distillation to give the residue, which was added in 100 ml of tetrahydrofuran, together with 10% hydrochloric acid. The mixed solution was deacetylated by refluxing for two hours to give N,N'-bis(3-methylphenyl)-2,3-naphthylenediamine represented by the formula (1E): ##STR34##
Then, this compound (8.46 g), 3-isopropyliodobenzene (12.3 g) represented by the formula (1F): ##STR35## potassium carbonate (13.8 g) and copper powder (1 g) were added in 150 ml of nitrobenzene, and the mixture was refluxed while a nitrogen gas was blowing into this reaction system under vigorous stirring for 24 hours. The water content produced in the reaction was removed out of the reaction system by azeotropic distillation with nitrobenzene, according to the same manner as that described above.
After the reaction solution was cooled, the inorganic substance was filtered off. Further, nitrobenzene was distilled off by steam distillation to give the residue, which was dissolved in cyclohexane. The solution was purified by subjecting to silica gel column chromatography and cyclohexane was distilled off to give a white precipitation. Then, the white precipitation was recrystallized from n-hexane to give the titled compound represented by the above formula (11-8) as an objective product (6.35 g, yield: 22.1%).
The results of the infrared spectroscopic analysis of the resultant compound are shown in FIG. 2. In addition, the results of the elemental analysis are shown below.
Elemental analysis (%):
Calcd.: C, 87.75; H, 7.37; N, 4.88
Found: C, 87.80; H, 7.33; N, 4.89
Example 4
Synthesis of N,N,N', N'-tetrakis(4-biphenylyl)-2,3-naphthylenediamine
According to the same manner as that described in Example 1 except for using 112.0 g of 4-iodobiphenyl represented by the formula (1G): ##STR36## in place of m-iodotoluene represented by the formula (1B), the titled compound represented by the above formula (11-12) was obtained as an objective product (24.6 g, yield: 32.1%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%),
Calcd.: C, 90.82; H, 5.52; N, 3.65
Found: C, 90.56; H, 5.65; N, 3.78
Example 5
Synthesis of N,N'-bis(3-methylphenyl)-N,N'-bis(4-ethylbiphenyl-4-yl)-2,3-naphthylenediamine
According to the same manner as that described in Example 3 except for using 15.4 g of 4-ethyl-4'-iodobiphenyl represented by the formula (1H): ##STR37## in place of 3-isopropyl-iodobenzene represented by the formula (1F), the titled compound represented by the above formula (11-13) was obtained as an objective product (9.82 g, yield: 23.1%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%):
Calcd.: C, 90.30; H, 6.40; N, 3.29
Found: C, 90.21; H, 6.45; N, 3.33
Example 6
Synthesis of N,N,N',N'-tetrakis(3-methylphenyl)-1,3-naphthylenediamine
According to the same manner as that described in Example 1 except for using 15.8 g of 1,3-naphthylenediamine represented by the formula (1I): ##STR38## in place of 2,3-naphthylenediamine represented by the formula (1A), the titled compound represented by the above formula (13-2) was obtained as an objective product (14.7 g, yield: 28.3%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%):
Calcd.: C, 87.98; H, 6.61; N, 5.40
Found: C, 87.78; H, 6.66; N, 5.55
Example 7
Synthesis of N,N'-bis(3-methylphenyl)-N,N'-bis(3-isopropylphenyl)-1,3-naphthylenediamine
According to the same manner as that described in Example 3 except for using 12.1 g of N,N'-diacetyl-1,3-naphthylenediamine represented by the formula (1J): ##STR39## in place of N,N'-diacetyl-2,3-naphthylenediamine represented by the formula (1D), the titled compound represented by the above formula (13-7) was obtained as an objective product (5.72 g, yield: 19.9%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%):
Calcd.: C, 87.75; H, 7.37; N, 4.88
Found: C, 87.69; H, 7.25; N, 4.94
Example 8
Synthesis of N,N'-bis(4-methylphenyl)-N,N'-bis(4'-ethylbiphenyl-4-yl)-1,3-naphthylenediamine
According to the same manner as that described in Example 3 except for using 12.1 g of N,N'-diacetyl-1,3-naphthylenediamine represented by the formula (1J) in place of N,N'-diacetyl-2,3-naphthylenediamine represented by the formula (1D), using 21.8 g of p-iodotoluene represented by the formula (1K): ##STR40## in place of m-iodotoluene represented by the formula (1B) and using 15.4 g of 4-ethyl-4'-iodobiphenyl represented by the formula (1H) in place of 3-isopropyl-iodobenzene represented by the formula (1F), the titled compound represented by the above formula (13-12) was obtained as an objective product (8.71 g, yield: 20.5%).
The results of the elemental analysis of the above compound are shown below.
Elemental analysis (%):
Calcd.: C, 90.30; H, 6.40; N, 3.29
Found: C, 90.39; H, 6.45; N, 3.25
Examples 9 to 15 and Comparative Example 1
(Single-layer type photosensitive material for digital light source)
Parts by weight of X-type metal-free phthalocyanine represented by the formula (8-1): ##STR41## as the electric charge generating material, 100 parts by weight of an electric charge transferring material and 100 parts by weight of polycarbonate as the binding resin were mixed/dispersed with 800 parts by weight of tetrahydrofuran as the solvent using a ball mill for 50 hours to prepare a coating solution for single-layer type electrophotosensitive layer. Then, this coating solution was applied on an aluminum tube as the conductive substrate by a dip coating method, followed by hot-air drying at 110.degree. C. for 30 minutes to produce a single-layer type electrophotosensitive material for digital light source, which has a single-layer type photosensitive layer of 25 .mu.m in film thickness.
The electric charge transferring material used in the Examples is a naphthylenediamine derivative of the present invention. The respective compounds of the naphthylenediamine derivative are shown by the number of the above compounds in Table 1. In addition, the electric charge transferring material used in the Comparative Example is a m-phenylenediamine derivative represented by the above formula (71-1).
The electrophotosensitive materials of the above Examples and Comparative Example were subjected to the following initial electric characteristics test (I) and electric characteristics test (I) after repeated exposure, and their characteristics were evaluated.
Initial electric characteristics test (I)
By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of the electrophotosensitive materials of the respective Examples and Comparative Examples to charge the surface at +700.+-.20V, and a surface potential V.sub.0 (V) was measured. Then, monochromatic light having a wavelength of 780 nm (half-width: 20 nm) and a light intensity of 10 .mu.J/cm.sup.2 from white light of a halogen lamp as an exposure light source through a band-pass filter was irradiated on the surface of the electrophotosensitive material for 1.5 seconds (irradiation time) and the time which is necessary for the above surface potential to be reduced to half was measured, thereby calculating a half-life exposure E.sub.1/2 (.mu.J/cm.sup.2). Further, a surface potential at the time at which 0.5 seconds has passed since the beginning of exposure was measured as a residual potential V.sub.r (V).
Electric characteristics test (I) after repeated exposure
An electrophotosensitive material of the respective Examples and Comparative Examples was fit with a laser beam printer (Model TC-650, manufactured by Mita Industrial Co., Ltd.) and, after the image was formed 10,000 times, a surface potential V.sub.0 (V) and a residual potential V.sub.r (V) were measured using the above drum sensitivity tester according to the same manner as that described above. Then, a change in measured value from the initial value (i.e. .DELTA.V.sub.0 (V) and .DELTA.V.sub.r (V)) was determined.
The results are shown in Table 1.
In the following tables, "CTM" denotes "charge transferring
TABLE 1______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 9 11-2 706 49 1.35 -15 +5Ex. 10 11-6 701 54 1.36 -20 +4Ex. 11 11-8 702 48 1.40 -25 +7Ex. 12 11-13 700 51 1.36 -24 +9Ex. 13 13-2 702 42 1.36 -20 +9Ex. 14 13-7 700 53 1.37 -15 +5Ex. 15 13-12 703 49 1.39 -25 +8Comp. Ex. 1 71-1 700 130 2.45 -220 +55______________________________________
Examples 16 to 21 and Comparative Example 2
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a perylene pigment represented by the formula (9-1): ##STR42## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 2, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the following initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated.
Initial electric characteristics test (II)
By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of the electrophotosensitive materials of the respective Examples and Comparative Examples to charge the surface at +700 V.+-.20V, and a surface potential V.sub.0 (V) was measured. Then, white light from a halogen lamp as an exposure light source (light intensity: 10 lux) was irradiated on the surface of the electrophotosensitive material for 1.5 seconds (irradiation time) and the time which is necessary for the above surface potential to be reduced to half was measured, thereby calculating a half-life exposure E.sub.1/2 (lux.multidot.second). Further, a surface potential at the time at which 0.5 seconds has passed since the beginning of exposure was measured as a residual potential V.sub.r (V).
Electric characteristics test (II) after repeated exposure
An electrophotosensitive material of the respective Examples and Comparative Examples was fit with an electrostatic copying machine (Model DC2556, manufactured by Mita Industrial Co., Ltd.) and, after the image was formed 10,000 times, a surface potential V.sub.0 (V) and a residual potential V.sub.r (V) were measured using the above drum sensitivity tester according to the same manner as that described above. Then, a change in measured value from the initial value (i.e. .DELTA.V.sub.0 (V) and .DELTA.V.sub.r (V)) was determined.
The results are shown in Table 2.
TABLE 2______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 16 11-2 700 125 1.75 -15 +15Ex. 17 11-8 701 135 1.73 -20 +10Ex. 18 11-13 699 135 1.79 -30 +10Ex. 19 13-2 700 130 1.76 -15 +10Ex. 20 13-7 701 136 1.75 -20 +15Ex. 21 13-10 695 134 1.80 -25 +15Comp. Ex. 2 71-1 703 195 2.48 -90 +55______________________________________
Examples 22 to 28 and Comparative Example 3
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-1): ##STR43## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 3, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 3.
TABLE 3______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 22 11-2 698 95 1.35 -20 +5Ex. 23 11-8 702 70 1.32 -30 +15Ex. 24 11-13 698 65 1.48 -20 +15Ex. 25 11-6 701 49 1.30 -15 .+-.0Ex. 26 13-2 700 96 1.34 -21 +5Ex. 27 13-7 706 69 1.32 -29 +20Ex. 28 13-10 698 67 1.48 -20 +10Comp. Ex. 3 71-1 701 124 1.60 -215 +45______________________________________
Examples 29 to 38 and Comparative Example 4
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-2): ##STR44## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 4, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 4.
TABLE 4______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 29 11-2 695 80 1.30 -20 +5Ex. 30 11-8 699 69 1.45 -40 +15Ex. 31 11-13 698 52 1.40 -15 +20Ex. 32 11-6 702 44 1.43 -55 +10Ex. 33 11-14 702 43 1.45 -45 +15Ex. 34 11-18 705 42 1.40 -40 +15Ex. 35 11-20 704 45 1.46 -10 +15Ex. 36 13-2 695 82 1.30 -15 +5Ex. 37 13-7 700 70 1.42 -45 +10Ex. 38 13-10 698 56 1.42 -20 +20Comp. Ex. 4 71-1 702 131 1.72 -180 +55______________________________________
Examples 39 to 45 and Comparative Example 5
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-3): ##STR45## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 5, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 5.
TABLE 5______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 39 11-2 698 75 1.29 -30 +20Ex. 40 11-8 698 60 1.50 -35 +20Ex. 41 11-13 701 54 1.40 -10 +35Ex. 42 11-6 702 45 1.50 -20 +15Ex. 43 13-2 698 77 1.30 -30 +10Ex. 44 13-7 698 62 1.48 -40 +25Ex. 45 13-10 700 50 1.41 -10 +40Comp. Ex. 5 71-1 703 124 1.62 -165 +40______________________________________
Examples 46 to 51 and Comparative Example 6
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-4): ##STR46## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 6, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 6.
TABLE 6______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 46 11-2 698 35 1.14 -35 +5Ex. 47 11-8 700 45 1.26 -30 +10Ex. 48 11-13 705 31 1.15 -10 +20Ex. 49 13-2 700 34 1.15 -40 +5Ex. 50 13-7 702 45 1.30 -30 +10Ex. 51 13-10 705 33 1.17 -15 +20Comp. Ex. 6 71-1 702 110 1.46 -165 +50______________________________________
Examples 52 to 57 and Comparative Example 7
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-5): ##STR47## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 7, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 7.
TABLE 7______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 52 11-2 693 80 1.30 -40 +10Ex. 53 11-8 701 70 1.59 -20 +10Ex. 54 11-13 706 53 1.32 -5 +25Ex. 55 13-2 693 82 1.30 -40 +15Ex. 56 13-7 701 72 1.60 -25 +15Ex. 57 13-10 704 55 1.30 -5 +20Comp. Ex. 7 71-1 699 138 1.77 -250 +40______________________________________
Examples 58 to 64 and Comparative Example 8
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-6): ##STR48## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the compounds in Table 8, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 8.
TABLE 8______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 58 11-2 700 50 1.35 -20 .+-.0Ex. 59 11-8 702 56 1.50 -25 .+-.0Ex. 60 11-13 700 50 1.43 -50 +10Ex. 61 11-6 705 50 1.20 -30 +20Ex. 62 13-2 701 50 1.35 -25 .+-.0Ex. 63 13-7 702 58 1.52 -25 .+-.0Ex. 64 13-10 702 54 1.42 -50 +15Comp. Ex. 8 11-1 698 140 2.17 -225 +65______________________________________
Examples 65 to 70 and Comparative Example 9
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 9 to 15 and Comparative Example 1 except for using 5 parts by weight of a bisazo pigment represented by the formula (10-7): ##STR49## as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 9, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 9.
TABLE 9______________________________________ Initial Characteristics After RepeatingCTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 65 11-2 705 52 1.30 -15 +5Ex. 66 11-8 703 60 1.35 -15 .+-.0Ex. 67 11-13 701 65 1.45 -15 .+-.0Ex. 68 13-2 705 53 1.29 -17 +5Ex. 69 13-7 703 62 1.37 -15 .+-.0Ex. 70 13-10 701 69 1.47 -20 .+-.0Comp. Ex. 9 71-1 695 138 1.98 -250 +50______________________________________
Examples 71 to 77 and Comparative Example 10
(Multi-layer type electrophotosensitive material for digital light source)
2.5 Parts by weight of X-type metal-free phthalocyanine represented by the above formula (8-1) as the electric charge generating material and 1 part by weight of polyvinyl butyral as the binding resin were mixed/dispersed with 15 parts by weight of tetrahydrofuran as the solvent using a ball mill to prepare a coating solution for electric charge generating layer. Then, this coating solution was applied on an aluminum tube as the conductive substrate by a dip coating method, followed by hot-air drying at 110.degree. C. for 30 minutes to form an electric charge generating layer of 0.5 .mu.m in film thickness.
Then, 1 part by weight of an electric charge transferring material and 1 part by weight of polycarbonate as the binding resin were mixed/dispersed with 10 parts by weight of tetrahydrofuran as the solvent using a ball mill to prepare a coating solution for electric charge transferring layer. Then, this coating solution was applied on the electric charge generating layer by a dip coating method, followed by hot-air drying at 110.degree. C. for 30 minutes to form an electric charge transferring layer of 20 .mu.m in film thickness, thereby affording a multi-layer type electrophotosensitive material for digital light source.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 10 according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the following initial electric characteristics test (III) and electric characteristics test (III) after repeated exposure, and their characteristics were evaluated.
Initial electric characteristics test (III)
By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of the electrophotosensitive materials of the respective Examples and Comparative Examples to charge the surface at -700.+-.20V, and a surface potential V.sub.0 (V) was measured. Then, monochromatic light having a wavelength of 780 nm (half-width: 20 nm) and a light intensity of 10 .mu.J/cm from white light of a halogen lamp as an exposure light source through a band-pass filter was irradiated on the surface of the electrophotosensitive material for 1.5 seconds. (irradiation time) and the time which is necessary for the above surface potential to be reduced to half was measured, thereby calculating a half-life exposure E.sub.1/2 (.mu.J/cm.sup.2). Further, a surface potential at the time at which 0.5 seconds has passed since the beginning of exposure was measured as a residual potential V.sub.r (V).
Electric characteristics test (III) after repeated exposure
An electrophotosensitive material of the respective Examples and Comparative Examples was fit with a laser beam printer (Model LP-2080, manufactured by Mita Industrial Co., Ltd.) and, after the image was formed 10,000 times, a surface potential V.sub.0 (V) and a residual potential V.sub.r (V) were measured using the above drum sensitivity tester according to the same manner as that described above. Then, a change in measured value from the initial value (i.e. .DELTA.V.sub.0 (V) and .DELTA.V.sub.r (V)) was determined.
The results are shown in Table 10.
TABLE 10______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 71 11-2 -700 -11 0.41 -40 +5Ex. 72 11-6 -700 -12 0.42 -45 +5Ex. 73 11-8 -701 -15 0.48 -20 +10Ex. 74 11-13 -702 -13 0.65 -15 +15Ex. 75 13-2 -701 -13 0.41 -40 +10Ex. 76 13-7 -700 -12 0.44 -40 +5Ex. 77 13-12 -700 -14 0.49 -25 +20Comp. Ex. 10 71-1 -695 -22 1.85 -55 +35______________________________________
Examples 78 to 83 and Comparative Example 11
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 11, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the following initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated.
Initial electric characteristics test (IV)
By using a drum sensitivity tester manufactured by GENTEC Co., a voltage was applied on the surface of the electrophotosensitive materials of the respective Examples and Comparative Examples to charge the surface at -700 V.+-.20V, and a surface potential V.sub.0 (V) was measured. Then, white light from a halogen lamp as an exposure light source (light intensity: 10 lux) was irradiated on the surface of the electrophotosensitive material for 1.5 seconds (irradiation time) and the time which is necessary for the above surface potential to be reduced to half was measured, thereby calculating a half-life exposure E.sub.1/2 (lux.multidot.second). Further, a surface potential at the time at which 0.5 seconds has passed since the beginning of exposure was measured as a residual potential V.sub.r (V).
Electric characteristics test (IV) after repeated exposure
An electrophotosensitive material of the respective Examples and Comparative Examples was fit with an electrostatic copying machine (Model DC2556 which is reconstructed for the negative charging type, manufactured by Mita Industrial Co., Ltd.) and, after the image was formed 10,000 times, a surface potential V.sub.0 (V) and a residual potential V.sub.r (V) were measured using the above drum sensitivity tester according to the same manner as that described above. Then, a change in measured value from the initial value (i.e. .DELTA.V.sub.0 (V) and .DELTA.V.sub.r (V)) was determined.
The results are shown in Table 11.
TABLE 11______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 78 11-2 -702 -130 1.93 -65 +20Ex. 79 11-8 -698 -134 1.92 -75 +10Ex. 80 11-13 -689 -135 1.96 -60 +5Ex. 81 13-2 -700 -125 1.90 -70 +15Ex. 82 13-7 -699 -135 1.90 -80 +10Ex. 83 13-12 -698 -135 1.96 -60 +5Comp. Ex. 11 71-1 -699 -157 2.53 -40 +65______________________________________
Examples 84 to 90 and Comparative Example 12
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 12, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 12.
TABLE 12______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 84 11-2 -702 -25 0.51 -55 +15Ex. 85 11-8 -699 -29 0.53 -70 +10Ex. 86 11-13 -697 -25 0.40 -20 .+-.0Ex. 87 11-6 -705 -27 0.36 -45 +5Ex. 88 13-2 -701 -26 0.55 -55 +20Ex. 89 13-7 -701 -30 0.55 -70 +15Ex. 90 13-12 -697 -25 0.40 -20 .+-.0Comp. Ex. 12 71-1 -704 -90 1.53 -140 +45______________________________________
Examples 91 to 100 and Comparative Example 13
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 13, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 13.
TABLE 13______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 91 11-2 -704 -26 0.56 -45 +15Ex. 92 11-8 -699 -24 0.55 -65 .+-.0Ex. 93 11-13 -698 -25 0.42 -50 +15Ex. 94 11-6 -762 -23 0.34 -20 .+-.0Ex. 95 11-14 -704 -22 0.43 -50 +10Ex. 96 11-18 -703 -29 0.46 -55 +15Ex. 97 11-20 -702 -29 0.44 -30 +5Ex. 98 13-2 -702 -27 0.57 -40 +15Ex. 99 13-7 -701 -30 0.55 -65 .+-.0Ex. 100 13-12 -698 -30 0.42 -50 +15Comp. Ex. 13 71-1 -697 -125 1.65 -175 +50______________________________________
Examples 101 to 107 and Comparative Example 14
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 14, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 14.
TABLE 14______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 101 11-2 -704 -28 0.52 -60 +20Ex. 102 11-8 -700 -24 0.56 -60 .+-.0Ex. 103 11-13 -697 -21 0.43 -50 +20Ex. 104 11-6 -704 -27 0.45 -50 +20Ex. 105 13-2 -703 -29 0.50 -55 +20Ex. 106 13-7 -700 -24 0.56 -60 .+-.0Ex. 107 13-12 -699 -21 0.43 -50 +20Comp. Ex. 14 71-1 -701 -104 1.74 -125 +40______________________________________
Examples 108 to 113 and Comparative Example 15
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 15, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 15.
TABLE 15______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 108 11-2 -704 -12 0.38 -40 +10Ex. 109 11-8 -701 -13 0.42 -60 -5Ex. 110 11-13 -699 -14 0.35 -25 +15Ex. 111 13-2 -703 -15 0.40 -50 +20Ex. 112 13-7 -702 -15 0.42 -60 -5Ex. 113 13-12 -699 -15 0.35 -25 +15Comp. Ex. 15 71-1 -701 -75 1.42 -110 +35______________________________________
Examples 114 to 119 and Comparative Example 16
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 16, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 16.
TABLE 16______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 114 11-2 -702 -31 0.86 -60 +20Ex. 115 11-8 -704 -32 0.86 -55 +10Ex. 116 11-13 -701 -35 0.56 -50 +10Ex. 117 13-2 -700 -30 0.89 -55 +10Ex. 118 13-7 -703 -30 0.81 -55 +10Ex. 119 13-12 -701 -35 0.56 -50 +10Comp. Ex. 16 71-1 -700 -135 1.95 -190 +60______________________________________
Examples 120 to 126 and Comparative Example 17
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 17, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 17.
TABLE 17______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 120 11-2 -699 -34 0.81 -55 +5Ex. 121 11-8 -700 -30 0.73 -20 +15Ex. 122 11-13 -702 -34 0.55 -55 +35Ex; 123 11-6 -701 -35 0.62 -50 +35Ex. 124 13-2 -700 -35 0.83 -55 +5Ex. 125 13-7 -700 -25 0.73 -20 +15Ex. 126 13-12 -700 -34 0.55 -55 +35Comp. Ex. 17 71-1 -699 -134 1.82 -200 +70______________________________________
Examples 127 to 132 and Comparative Example 18
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 71 to 77 and Comparative Example 10 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-7) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
The electric charge transferring materials used in the Examples and Comparative Examples are shown by the number of the above compounds in Table 18, according to the same manner as that described above.
The electrophotosensitive materials of the above Examples and Comparative Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 18.
TABLE 18______________________________________ Initial Characteristics After Repeating CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 127 11-2 -698 -33 0.83 -45 .+-.0Ex. 128 11-8 -702 -29 0.59 -25 +15Ex. 129 11-13 -703 -34 0.53 -55 +34Ex. 130 13-2 -699 -30 0.84 -40 .+-.0Ex. 131 13-7 -701 -29 0.59 -25 +15Ex. 132 13-12 -703 -35 0.53 -55 +34Comp. Ex. 18 71-1 -700 -138 1.81 -130 +75______________________________________
Examples 133 to 144
(Single-layer type electrophotosensitive material for digital light source)
According to the same manner as that described in Examples 9 to 15 except for using 5 parts by weight of X-type metal-free phthalocyanine represented by the above formula (8-1) as the electric charge generating material, 100 parts by weight of a naphthylenediamine derivative as the hole transferring material, 100 parts by weight of polycarbonate as the binding resin and 30 parts by weight (15 parts by weight, in case of Examples 135, 139 and 143) of a 2,4,7-trinitrofluorenonimine derivative as the electron transferring material, a single-layer type electrophotosensitive material for digital light source was produced.
The hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 19, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (I) and electric characteristics test (I) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 19.
In the following tables, "HTM" and "ETM" denote "hole transferring material" and "electron transferring material", respectively.
TABLE 19______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 133 11-8 2-5 702 24 1.28 -16 +3Ex. 134 11-8 2-6 701 23 1.29 -15 +2Ex. 135 11-8 2-16 698 25 1.30 -16 +4Ex. 136 11-8 2-16 705 19 1.25 -11 +5Ex. 137 11-11 2-5 699 24 1.28 -19 +3Ex. 138 11-11 2-6 706 25 1.27 -15 +1Ex. 139 11-11 2-16 695 25 1.29 -13 +2Ex. 140 11-11 2-16 699 20 1.25 -9 +5Ex. 141 13-2 2-5 703 21 1.27 -13 +4Ex. 142 13-2 2-6 706 23 1.23 -14 +3Ex. 143 13-2 2-16 710 23 1.24 -10 +2Ex. 144 13-2 2-16 697 19 1.28 -9 +3______________________________________
Examples 145 to 151
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 133 to 144 except for using 5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 15 parts by weight only in Example 146, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 20, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 20.
TABLE 20______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 145 11-8 2-5 697 83 1.33 -20 +9Ex. 146 11-8 2-5 701 85 1.35 -28 +16Ex. 147 11-8 2-6 708 79 1.32 -18 +13Ex. 148 11-11 2-5 702 77 1.30 -13 +11Ex. 149 11-11 2-16 701 81 1.34 -14 +10Ex. 150 13-2 2-5 699 80 1.33 -12 +8Ex. 151 13-2 2-6 704 78 1.32 -16 +5______________________________________
Examples 152 to 158
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 133 to 144 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine 5 derivative was 15 parts by weight only in Example 155, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 21, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 21.
TABLE 21______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 152 11-8 2-5 702 65 1.23 -15 +3Ex. 153 11-8 2-6 706 63 1.21 -18 +7Ex. 154 11-11 2-5 697 62 1.21 -10 +8Ex. 155 11-11 2-5 703 64 1.23 -18 +11Ex. 156 11-11 2-16 706 60 1.20 -12 +10Ex. 157 13-2 2-5 700 59 1.19 -12 +11Ex. 158 13-2 2-6 695 60 1.21 -19 +9______________________________________
Examples 159 to 165
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 133 to 144 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 15 parts by weight only in Example 161, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 22, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 22.
TABLE 22______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 159 11-8 2-5 702 50 1.14 -12 +7Ex. 160 11-8 2-6 705 49 1.13 -16 +8Ex. 161 11-11 2-5 699 52 1.21 -18 +9Ex. 162 11-11 2-5 699 48 1.13 -15 +5Ex. 163 11-11 2-16 694 45 1.12 -13 +5Ex. 164 13-2 2-5 689 43 1.13 -15 +3Ex. 165 13-2 2-6 697 50 1.15 -14 +6______________________________________
Examples 166 to 172
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 133 to 144 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 15 parts by weight only in Example 168, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 23, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 23.
TABLE 23______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 166 11-8 2-5 703 41 1.11 -19 +5Ex. 167 11-8 2-6 704 42 1.12 -12 +8Ex. 168 11-11 2-5 699 45 1.14 -14 +6Ex. 169 11-11 2-5 700 39 1.09 -13 +4Ex. 170 11-11 2-16 703 41 1.13 -15 +6Ex. 171 13-2 2-5 700 37 1.09 -14 +10Ex. 172 13-2 2-6 699 36 1.07 -12 +9______________________________________
Examples 173 to 179
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 133 to 144 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 15 parts by weight only in Example 175, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 24, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 24.
TABLE 24______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 173 11-8 2-5 703 23 1.01 -10 +5Ex. 174 11-8 2-6 705 21 1.00 -12 +7Ex. 175 11-11 2-5 701 28 1.09 -13 +4Ex. 176 11-11 2-5 704 23 1.01 -9 +6Ex. 177 11-11 2-16 702 19 1.00 -8 +3Ex. 178 13-2 2-5 700 18 0.98 -11 +2Ex. 179 13-2 2-6 703 17 0.97 -13 +4______________________________________
Examples 180 to 188
(Single-layer type electrophotosensitive material for digital light source)
According to the same manner as that described in Examples 133 to 144 except for using a diphenoquinone derivative as the electron transferring material, a single-layer type electrophotosensitive material for digital light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 25, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (I) and electric characteristics test (I) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 25.
TABLE 25______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 180 11-8 3-1 710 35 1.31 -15 +3Ex. 181 11-8 3-3 705 38 1.32 -14 +3Ex. 182 11-8 3-7 702 36 1.30 -18 +4Ex. 183 11-11 3-1 704 35 1.35 -23 +5Ex. 184 11-11 3-3 697 37 1.31 -19 +5Ex. 185 11-11 3-7 709 39 1.33 -17 +4Ex. 186 13-2 3-1 698 37 1.34 -15 +6Ex. 187 13-2 3-3 699 36 1.30 -18 +5Ex. 188 13-2 3-7 704 38 1.31 -13 +4______________________________________
Examples 189 to 195
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 180 to 188 except for using 5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 15 parts by weight only in Example 190, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 26, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 26.
TABLE 26______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 189 11-8 3-1 697 89 1.35 -25 +15Ex. 190 11-8 3-1 705 88 1.38 -28 +16Ex. 191 11-8 3-3 705 88 1.34 -21 +13Ex. 192 11-11 3-1 702 78 1.31 -23 +12Ex. 193 11-11 3-7 698 76 1.31 -24 +16Ex. 194 13-2 3-1 699 83 1.33 -28 +17Ex. 195 13-2 3-3 696 75 1.29 -27 +13______________________________________
Examples 196 to 202
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 180 to 188 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 15 parts by weight only in Example 197, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 27, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 27.
TABLE 27______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 196 11-8 3-1 705 70 1.25 -21 +12Ex. 197 11-8 3-1 706 72 1.26 -20 +10Ex. 198 11-8 3-3 697 69 1.23 -23 +11Ex. 199 11-11 3-1 703 65 1.21 -28 +10Ex. 200 11-11 3-7 701 68 1.22 -26 +15Ex. 201 13-2 3-1 697 63 1.21 -25 +13Ex. 202 13-2 3-3 704 65 1.22 -23 +14______________________________________
Examples 203 to 209
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 180 to 188 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 15 parts by weight only in Example 204, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 28, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 28.
TABLE 28______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 203 11-8 3-1 703 59 1.19 -32 +14Ex. 204 11-8 3-1 698 63 1.23 -35 +16Ex. 205 11-8 3-3 702 62 1.21 -31 +13Ex. 206 11-11 3-1 699 55 1.18 -29 +15Ex. 207 11-11 3-7 701 51 1.16 -30 +12Ex. 208 13-2 3-1 700 63 1.23 -26 +13Ex. 209 13-2 3-3 705 61 1.21 -23 +13______________________________________
Examples 210 to 216
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 180 to 188 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 15 parts by weight only in Example 211, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 29, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 29.
TABLE 29______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 210 11-8 3-1 706 55 1.18 -30 +15Ex. 211 11-8 3-1 701 59 1.20 -34 +14Ex. 212 11-8 3-3 708 53 1.17 -29 +13Ex. 213 11-11 3-1 706 58 1.19 -27 +12Ex. 214 11-11 3-7 701 52 1.17 -28 +11Ex. 215 13-2 3-1 699 50 1.14 -23 +13Ex. 216 13-2 3-3 696 51 1.16 -28 +16______________________________________
Examples 217 to 223
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 180 to 188 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 15 parts by weight only in Example 218, and it was 30 parts by weight in other Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 30, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 30.
TABLE 30______________________________________ Initial Characteristics After RepeatingHTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________Ex. 217 11-8 3-1 703 30 1.05 -25 +12Ex. 218 11-8 3-1 701 33 1.07 -26 +14Ex. 219 11-8 3-3 697 28 1.04 -28 +14Ex. 220 11-11 3-1 700 26 1.02 -27 +13Ex. 221 11-11 3-7 705 32 1.06 -28 +17Ex. 222 13-2 3-1 701 30 1.03 -29 +11Ex. 223 13-2 3-3 709 29 1.03 -21 +14______________________________________
Examples 224 to 233
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 145 to 151 except for using an ethylated nitrofluorenonimine derivative as the electron transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 31, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 31.
TABLE 31______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________224 11-2 4-1 699 86 1.44 -20 +10225 11-2 4-2 703 85 1.44 -15 +5226 11-2 4-3 704 90 1.53 -22 +13227 11-2 4-4 707 95 1.55 -22 +15228 11-11 4-1 695 88 1.49 -25 +13229 11-11 4-2 700 87 1.49 -20 +10230 11-11 4-3 700 93 1.54 -22 +15231 13-2 4-1 702 88 1.48 -21 +14232 13-2 4-2 701 88 1.48 -18 +11233 13-2 4-3 701 92 1.53 -17 +14______________________________________
Examples 234 to 243
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 224 to 233 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 32, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 32.
TABLE 32______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________234 11-2 4-1 704 66 1.30 -18 +14235 11-2 4-2 700 65 1.29 -13 +6236 11-2 4-3 700 70 1.35 -15 +12237 11-2 4-4 703 74 1.38 -20 +10238 11-11 4-1 710 67 1.34 -15 +11239 11-11 4-2 691 65 1.30 -10 +3240 11-11 4-3 697 73 1.37 -20 +15241 13-2 4-1 699 70 1.35 -16 +12242 13-2 4-2 702 66 1.30 -11 +9243 13-2 4-3 703 72 1.35 -19 +10______________________________________
Examples 244 to 253
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 224 to 233 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 33, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 33.
TABLE 33______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________244 11-2 4-1 695 50 1.18 -16 +9245 11-2 4-2 700 51 1.19 -10 +7246 11-2 4-3 703 55 1.22 -18 +9247 11-2 4-4 705 60 1.23 -20 +10248 11-11 4-1 701 48 1.15 -17 +10249 11-11 4-2 702 49 1.15 -15 +9250 11-11 4-3 699 56 1.23 -20 +9251 13-2 4-1 712 42 1.13 -15 +13252 13-2 4-2 705 45 1.13 -17 +11253 13-2 4-3 704 53 1.20 -19 +14______________________________________
Examples 254 to 263
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 224 to 233 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 34, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 34.
TABLE 34______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________254 11-2 4-1 706 44 1.14 -16 +12255 11-2 4-2 708 40 1.10 -13 +6256 11-2 4-3 701 50 1.19 -17 +10257 11-2 4-4 696 53 1.19 -21 +14258 11-11 4-1 698 45 1.14 -18 +15259 11-11 4-2 699 44 1.14 -15 +14260 11-11 4-3 700 49 1.19 -19 +11261 13-2 4-1 706 41 1.11 -20 +13262 13-2 4-2 695 43 1.12 -15 +10263 13-2 4-3 691 45 1.15 -20 +12______________________________________
Examples 264 to 273
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 224 to 233 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 35, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 35.
TABLE 35______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________264 11-2 4-1 710 37 1.09 -21 +13265 11-2 4-2 708 33 1.08 -15 +9266 11-2 4-3 691 40 1.10 -16 +11267 11-2 4-4 693 45 1.13 -25 +14268 11-11 4-1 709 40 1.10 -20 +10269 11-11 4-2 705 36 1.08 -18 +11270 11-11 4-3 700 42 1.10 -19 +13271 13-2 4-1 703 43 1.12 -17 +15272 13-2 4-2 702 35 1.08 -15 +8273 13-2 4-3 702 40 1.10 -23 +13______________________________________
Examples 274 to 280
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 145 to 151 except for using a tryptoanthrine derivative as the electron transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 36, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 36.
TABLE 36______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________274 11-2 5-3 710 99 1.30 -30 +18275 11-2 5-1 708 89 1.20 -24 +15276 11-2 5-4 700 92 1.18 -28 +10277 11-11 5-1 704 88 1.25 -25 +13278 11-11 5-4 702 85 1.27 -25 +13279 13-2 5-1 700 83 1.15 -23 +12280 13-2 5-4 705 83 1.15 -28 +15______________________________________
Examples 281 to 287
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 274 to 280 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 37, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 37.
TABLE 37______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________281 11-2 5-3 702 81 1.11 -30 +17282 11-2 5-1 695 75 1.03 -20 +15283 11-2 5-4 698 78 1.05 -23 +15284 11-11 5-1 702 74 1.04 -25 +15285 11-11 5-4 704 72 1.01 -24 +14286 13-2 5-1 703 70 0.99 -28 +13287 13-2 5-4 705 70 0.99 -28 +13______________________________________
Examples 288 to 294
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 274 to 280 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 38, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 38.
TABLE 38______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________288 11-2 5-3 706 70 1.03 -30 +18289 11-2 5-1 701 66 1.03 -25 +12290 11-2 5-4 699 62 1.01 -25 +12291 11-11 5-1 700 60 0.98 -30 +15292 11-11 5-4 704 60 0.98 -30 +15293 13-2 5-1 705 63 1.00 -27 +13294 13-2 5-4 701 63 1.00 -27 +12______________________________________
Examples 295 to 301
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 274 to 280 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 39, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 39.
TABLE 39______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________295 11-2 5-3 702 71 1.06 -35 +19296 11-2 5-1 704 65 1.03 -25 +15297 11-2 5-4 704 60 0.97 -35 +17298 11-11 5-1 705 64 1.03 -27 +13299 11-11 5-4 700 65 1.03 -24 +12300 13-2 5-1 702 66 1.05 -23 +15301 13-2 5-4 701 66 1.05 -25 +13______________________________________
Examples 302 to 308
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 274 to 280 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 40, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 40.
TABLE 40______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________302 11-2 5-3 700 68 1.04 -35 +20303 11-2 5-1 704 55 0.98 -25 +13304 11-2 5-4 697 61 1.00 -20 +15305 11-11 5-1 695 57 0.99 -25 +12306 11-11 5-4 700 59 1.00 -23 +13307 13-2 5-1 705 55 0.99 -23 +15308 13-2 5-4 705 57 0.99 -20 +10______________________________________
Examples 309 to 317
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 145 to 151 except for using a tryptoanthrinimine derivative as the electron transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 41, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 41.
TABLE 41______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________309 11-2 6-3 705 80 1.40 -21 +12310 11-2 6-6 704 90 1.54 -25 +15311 11-2 6-10 701 85 1.43 -23 +13312 11-11 6-3 701 83 1.42 -25 +14313 11-11 6-6 700 89 1.53 -25 +10314 11-11 6-10 695 86 1.45 -20 +10315 13-2 6-3 704 84 1.44 -20 +12316 13-2 6-6 703 83 1.43 -18 +12317 13-2 6-10 704 86 1.44 -23 +13______________________________________
Examples 318 to 326
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 309 to 317 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 42, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 42.
TABLE 42______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________318 11-2 6-3 706 60 1.25 -20 +10319 11-2 6-6 703 69 1.35 -15 +12320 11-2 6-10 700 64 1.30 -18 +9321 11-11 6-3 697 65 1.30 -18 +10322 11-11 6-6 701 72 1.37 -17 +10323 11-11 6-10 701 70 1.36 -15 +12324 13-2 6-3 695 66 1.29 -12 +11325 13-2 6-6 702 71 1.35 -16 +11326 13-2 6-10 700 69 1.30 -16 +13______________________________________
Examples 327 to 335
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 309 to 317 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 43, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 43.
TABLE 43______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________327 11-2 6-3 705 50 1.18 -10 +10328 11-2 6-6 700 55 1.25 -15 +9329 11-2 6-10 702 52 1.21 -14 +8330 11-11 6-3 703 52 1.20 -16 +12331 11-11 6-6 704 60 1.30 -15 +13332 11-11 6-10 700 56 1.25 -13 +14333 13-2 6-3 700 55 1.24 -13 +13334 13-2 6-6 695 57 1.25 -14 +10335 13-2 6-10 697 55 1.24 -13 +11______________________________________
Examples 336 to 344
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 309 to 317 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 44, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 44.
TABLE 44______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________336 11-2 6-3 702 39 1.10 -20 +13337 11-2 6-6 702 48 1.15 -14 +9338 11-2 6-10 704 45 1.14 -16 +10339 11-11 6-3 699 41 1.11 -17 +11340 11-11 6-6 700 50 1.18 -13 +10341 11-11 6-10 694 47 1.15 -15 +12342 13-2 6-3 705 44 1.13 -11 +11343 13-2 6-6 705 51 1.18 -16 +13344 13-2 6-10 689 47 1.16 -12 +13______________________________________
Examples 345 to 353
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 309 to 317 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 45, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 45.
TABLE 45______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________345 11-2 6-3 702 40 1.11 -15 +10346 11-2 6-6 700 49 1.19 -18 +12347 11-2 6-10 703 44 1.15 -17 +13348 11-11 6-3 703 42 1.11 -20 +14349 11-11 6-6 704 50 1.20 -16 +11350 11-11 6-10 705 50 1.20 -15 +11351 13-2 6-3 697 44 1.13 -13 +13352 13-2 6-6 698 52 1.20 -12 +13353 13-2 6-10 699 51 1.20 -15 +15______________________________________
Examples 354 to 359
(Single-layer type electrophotosensitive material for digital light source)
According to the same manner as that described in Examples 9 to 15 except for using 50 parts by weight of the naphthylenediamine in combination with 50 parts by weight of the phenylenediamine derivative as the electric charge transferring material, a single-layer type electrophotosensitive material for digital light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 46, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (I) and electric characteristics test (I) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 46.
TABLE 46______________________________________Example Initial Characteristics After RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________354 11-2 71-1 701 35 1.32 -15 +7355 11-2 71-2 708 29 1.27 -16 +8356 11-2 71-3 693 38 1.34 -13 +5357 11-11 71-1 712 36 1.32 -15 +5358 13-2 71-1 709 31 1.28 -16 +8359 11-2 72-1 709 34 1.31 -14 +6______________________________________
Examples 360 to 365
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 47, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 47.
TABLE 47______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________360 11-2 71-1 703 113 1.69 -20 +12361 11-2 71-2 714 110 1.68 -17 +15362 11-2 71-3 691 118 1.71 -19 +10363 11-11 71-1 698 119 1.71 -15 +10364 13-2 71-1 700 115 1.70 -18 +14365 11-2 72-1 697 112 1.70 -18 +13______________________________________
Examples 366 to 371
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 48, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 48.
TABLE 48______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________366 11-2 71-1 715 44 1.25 -20 +8367 11-2 71-2 709 48 1.28 -17 +7368 11-2 71-3 702 41 1.24 -20 +10369 11-11 71-1 716 39 1.24 -15 +5370 13-2 71-1 697 47 1.27 -19 +7371 11-2 72-1 718 42 1.25 -15 +8______________________________________
Examples 372 to 377
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 49, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 49.
TABLE 49______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________372 11-2 71-1 714 39 1.31 -18 +10373 11-2 71-2 691 35 1.28 -15 +8374 11-2 71-3 700 33 1.25 -20 +12375 11-11 71-1 698 33 1.23 -17 +11376 13-2 71-1 703 35 1.26 -13 +11377 11-2 72-1 700 34 1.26 -17 +11______________________________________
Examples 378 to 383
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 50, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 50.
TABLE 50______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________378 11-2 71-1 711 42 1.33 -21 +17379 11-2 71-2 693 37 1.30 -18 +18380 11-2 71-3 698 33 1.28 -15 +15381 11-11 71-1 709 39 1.31 -18 +20382 13-2 71-1 700 34 1.31 -15 +21383 11-2 72-1 705 35 1.29 -18 +16______________________________________
Examples 384 to 389
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 51, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 51.
TABLE 51______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________384 11-2 71-1 710 28 1.13 -22 +12385 11-2 71-2 699 24 1.10 -21 +14386 11-2 71-3 708 25 1.11 -17 +12387 11-11 71-1 703 27 1.13 -15 +11388 13-2 71-1 691 23 1.10 -15 +15389 11-2 72-1 699 25 1.10 -20 +12______________________________________
Examples 390 to 395
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 52, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 52.
TABLE 52______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________390 11-2 71-1 699 48 1.29 -19 +10391 11-2 71-2 712 45 1.25 -24 +13392 11-2 71-3 705 46 1.26 -18 +17393 11-11 71-1 707 43 1.24 -20 +9394 13-2 71-1 713 45 1.25 -15 +12395 11-2 72-1 712 44 1.25 -19 +8______________________________________
Examples 396 to 401
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 53, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 53.
TABLE 53______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________396 11-2 71-1 710 47 1.20 -18 .+-.0397 11-2 71-2 695 42 1.15 -15 +2398 11-2 71-3 700 41 1.17 -15 +10399 11-11 71-1 713 45 1.15 -19 +5400 13-2 71-1 698 42 1.15 -17 +3401 11-2 72-1 704 44 1.16 -16 .+-.0______________________________________
Examples 402 to 407
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 354 to 359 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-7) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 54, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 54.
TABLE 54______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________402 11-2 71-1 704 42 1.25 -16 +1403 11-2 71-2 706 42 1.28 -12 .+-.0404 11-2 71-3 708 48 1.28 -16 +2405 11-11 71-1 695 45 1.27 -15 .+-.0406 13-2 71-1 697 46 1.25 -12 +5407 11-2 72-1 711 45 1.26 -13 +2______________________________________
Examples 408 to 413
(Multi-layer type electrophotosensitive material for digital light source)
According to the same manner as that described in Examples 71 to 77 except for using 0.5 parts by weight of the naphthylenediamine derivative in combination with 0.5 parts by weight of the phenylenediamine derivative as the electric charge transferring material, a multi-layer type electrophotosensitive material for digital light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 55, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (III) and electric characteristics test (III) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 55.
TABLE 55______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________408 11-2 71-1 -715 -9 0.38 -16 +10409 11-2 71-2 -693 -8 0.36 -13 +7410 11-2 71-3 -700 -10 0.38 -15 +10411 11-11 71-1 -702 -8 0.35 -18 +9412 13-2 71-1 -705 -7 0.34 -17 +10413 11-2 72-1 -713 -10 0.37 -14 +9______________________________________
Examples 414 to 419
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 56, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 56.
TABLE 56______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________414 11-2 71-1 -713 -120 1.85 -60 +10415 11-2 71-2 -707 -118 1.84 -56 +12416 11-2 71-3 -705 -115 1.82 -50 +15417 11-11 71-1 -712 -117 1.84 -58 +8418 13-2 71-1 -699 -120 1.85 -50 +9419 11-2 72-1 -700 -118 1.85 -56 +12______________________________________
Examples 420 to 425
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 57, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 57.
TABLE 57______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________420 11-2 71-1 -698 -20 0.36 -30 +10421 11-2 71-2 -713 -18 0.34 -25 +5422 11-2 71-3 -700 -19 0.34 -27 +7423 11-11 71-1 -695 -20 0.35 -30 +10424 13-2 71-1 -710 -20 0.36 -28 +8425 11-2 72-1 -713 -17 0.34 -28 +9______________________________________
Examples 426 to 431
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 58, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 58.
TABLE 58______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________426 11-2 71-1 -697 -20 0.34 -25 +5427 11-2 71-2 -695 -15 0.31 -18 +10428 11-2 71-3 -708 -16 0.33 -19 +13429 11-11 71-1 -706 -15 0.32 -22 +15430 13-2 71-1 -704 -19 0.33 -21 +13431 11-2 72-1 -695 -17 0.32 -20 +14______________________________________
Examples 432 to 437
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 59, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 59.
TABLE 59______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________432 11-2 71-1 -700 -19 0.40 -45 +15433 11-2 71-2 -698 -15 0.41 -41 +20434 11-2 71-3 -691 -17 0.38 -46 +18435 11-11 71-1 -714 -19 0.38 -38 +18436 13-2 71-1 -703 -15 0.40 -40 +20437 11-2 72-1 -705 -16 0.40 -43 +20______________________________________
Examples 438 to 443
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 60, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 60.
TABLE 60______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________438 11-2 71-1 -697 -10 0.33 -48 +10439 11-2 71-2 -716 -7 0.31 -45 +20440 11-2 71-3 -702 -9 0.29 -43 +15441 11-11 71-1 -709 -11 0.30 -43 +13442 13-2 71-1 -715 -10 0.30 -40 +17443 11-2 72-1 -706 -9 0.32 -45 +15______________________________________
Examples 444 to 449
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 61, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 61.
TABLE 61______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________444 11-2 71-1 -703 -28 0.52 -41 +10445 11-2 71-2 -698 -25 0.50 -35 +9446 11-2 71-3 -700 -27 0.49 -38 +10447 11-11 71-1 -691 -25 0.50 -41 +8448 13-2 71-1 -714 -27 0.50 -39 +10449 11-2 72-1 -701 -26 0.49 -39 +8______________________________________
Examples 450 to 455
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 62, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 62.
TABLE 62______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________450 11-2 71-1 -709 -23 0.52 -25 .+-.0451 11-2 71-2 -698 -19 0.50 -20 +5452 11-2 71-3 -693 -20 0.48 -22 +2453 11-11 71-1 -711 -21 0.51 -23 +14454 13-2 71-1 -700 -21 0.49 -23 +3455 11-2 72-1 -703 -21 0.51 -24 +11______________________________________
Examples 456 to 461
(Multi-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 408 to 413 except for using 2.5 parts by weight of the bisazo pigment represented by the above formula (10-7) as the electric charge generating material, a multi-layer type electrophotosensitive material for analogue light source was produced.
In addition, the electric charge transferring materials used in the Examples are shown by the number of the above compounds in Table 63, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (IV) and electric characteristics test (IV) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 63.
TABLE 63______________________________________Example Initial Characteristics After RepeatingNo. CTM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________456 11-2 71-1 -691 -25 0.51 -20 +10457 11-2 71-2 -703 -22 0.48 -18 +5458 11-2 71-3 -708 -23 0.45 -15 +5459 11-11 71-1 -699 -25 0.47 -20 .+-.0460 13-2 71-1 -710 -24 0.47 -19 +6461 11-2 72-1 -698 -24 0.46 -19 +2______________________________________
Examples 462 to 469
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 145 to 151 except for using 50 parts by weight of the naphthylenediamine derivative in combination with 50 parts by weight of the phenylenediamine derivative as the hole transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 64, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 64.
TABLE 64______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________462 11-2 71-1 2-5 700 64 1.22 -3 -2463 11-2 71-2 2-5 699 66 1.25 -9 -5464 11-2 71-3 2-5 702 61 1.21 -6 +1465 11-2 71-1 2-6 701 63 1.20 -10 .+-.0466 11-11 71-1 2-5 700 63 1.26 -5 -1467 11-11 71-1 2-6 698 59 1.22 -5 +5468 13-2 71-1 2-5 705 65 1.24 -10 +8469 13-2 71-1 2-16 703 70 1.27 -10 +3______________________________________
Examples 470 to 477
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 462 to 469 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 65, according to the same manner as that described above
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 65.
TABLE 65______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________470 11-2 71-1 2-5 699 29 1.00 -5 +3471 11-2 71-2 2-5 700 24 1.03 -3 .+-.0472 11-2 71-3 2-5 704 26 1.05 .+-.0 -1473 11-2 71-1 2-6 705 25 1.05 +3 -3474 11-11 71-1 2-5 701 24 1.05 +5 -2475 11-11 71-1 2-6 699 28 1.01 -5 -5476 13-2 71-1 2-5 697 29 1.02 -4 -4477 13-2 71-1 2-16 700 29 1.03 -5 -5______________________________________
Examples 478 to 485
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 462 to 469 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 66, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 66.
TABLE 66______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________478 11-2 71-1 2-5 701 19 1.03 .+-.0 .+-.0479 11-2 71-2 2-5 700 21 1.05 -3 -4480 11-2 71-3 2-5 700 18 1.02 -5 -5481 11-2 71-1 2-6 697 23 1.06 -10 +3482 11-11 71-1 2-5 702 23 1.05 -8 -3483 11-11 71-1 2-6 704 25 1.07 -10 +5484 13-2 71-1 2-5 701 17 1.04 -5 +1485 13-2 71-1 2-16 700 20 1.04 -10 +3______________________________________
Examples 486 to 493
(Single-layer type electrophotosensitive material for analogue light source)
Examples 462 to 469 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 67, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 67.
TABLE 67______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________486 11-2 71-1 2-5 705 40 1.10 -10 +5487 11-2 71-2 2-5 698 38 1.10 -8 +5488 11-2 71-3 2-5 697 39 1.10 -10 +5489 11-2 71-1 2-6 698 32 1.11 -10 +8490 11-11 71-1 2-5 699 38 1.09 -5 +10491 11-11 71-1 2-6 701 35 1.10 -9 +6492 13-2 71-1 2-5 702 37 1.13 -10 +10493 13-2 71-1 2-16 699 37 1.14 -10 +10______________________________________
Examples 494 to 501
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 462 to 469 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the 2,4,7-trinitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 68, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 68.
TABLE 68______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________494 11-2 71-1 2-5 702 35 1.14 -10 +3495 11-2 71-2 2-5 700 42 1.16 -10 +5496 11-2 71-3 2-5 700 33 1.16 -8 +10497 11-2 71-1 2-6 701 44 1.16 -7 +5498 11-11 71-1 2-5 706 40 1.15 -5 +5499 11-11 71-1 2-6 705 45 1.17 -10 +6500 13-2 71-1 2-5 707 42 1.15 -9 +6501 13-2 71-1 2-16 698 44 1.16 -10 +6______________________________________
Examples 502 to 509
(Single-layer type electrophotosensitive material for digital light source)
According to the same manner as that described in Examples 180 to 188 except for using 50 parts by weight of the naphthylenediamine derivative in combination with 50 parts by weight of the phenylenediamine derivative as the hole transferring material, a single-layer type electrophotosensitive material for digital light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 69, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (I) and electric characteristics test (I) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 69.
TABLE 69______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________502 11-2 71-1 3-1 710 25 1.25 -10 +5503 11-2 71-2 3-1 708 20 1.20 -10 +7504 11-2 71-3 3-1 695 24 1.20 -8 +8505 11-11 71-1 3-1 713 20 1.18 -9 +6506 13-2 71-1 3-1 713 20 1.20 -10 +6507 11-2 71-1 3-3 708 23 1.21 -8 +5508 11-2 71-1 3-7 712 25 1.20 -10 +5509 11-2 72-1 3-1 705 21 1.20 -9 +8______________________________________
Examples 510 to 517
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the perylene pigment represented by the above formula (9-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 70, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 70.
TABLE 70______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________510 11-2 71-1 3-1 703 106 1.65 -7 +6511 11-2 71-2 3-1 695 99 1.60 -4 +8512 11-2 71-3 3-1 712 102 1.63 -1 +8513 11-11 71-1 3-1 698 101 1.62 -5 +5514 13-2 71-1 3-1 700 105 1.64 -9 +7515 11-2 71-1 3-3 710 105 1.63 -10 +9516 11-2 71-1 3-7 713 99 1.63 -5 +5517 11-2 72-1 3-1 697 101 1.63 -5 +8______________________________________
Examples 518 to 525
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 71, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 71.
TABLE 71______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________518 11-2 71-1 3-1 705 35 1.22 -10 .+-.0519 11-2 71-2 3-1 708 30 1.20 -9 +5520 11-2 71-3 3-1 695 33 1.21 -5 +2521 11-11 71-1 3-1 712 34 1.19 -9 +3522 13-2 71-1 3-1 702 34 1.20 -7 +5523 11-2 71-1 3-3 705 31 1.20 -8 +5524 11-2 71-1 3-7 707 30 1.19 -8 +4525 11-2 72-1 3-1 711 32 1.21 -8 +3______________________________________
Examples 526 to 533
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-2) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 72, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 72.
TABLE 72______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________526 11-2 71-1 3-1 710 30 1.20 -10 +8527 11-2 71-2 3-1 700 28 1.15 -7 +5528 11-2 71-3 3-1 695 25 1.15 -7 +8529 11-11 71-1 3-1 698 29 1.18 -8 +9530 13-2 71-1 3-1 702 30 1.17 -10 +10531 11-2 71-1 3-3 713 29 1.19 -9 +5532 11-2 71-1 3-7 705 25 1.18 -9 +5533 11-2 72-1 3-1 706 29 1.16 -8 +6______________________________________
Examples 534 to 541
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 73, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 73.
TABLE 73______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________534 11-2 71-1 3-1 695 28 1.25 -9 +8535 11-2 71-2 3-1 695 25 1.20 -9 +5536 11-2 71-3 3-1 700 25 1.21 -10 +5537 11-11 71-1 3-1 704 26 1.24 -8 +9538 13-2 71-1 3-1 705 30 1.18 -9 +10539 11-2 71-1 3-3 691 29 1.19 -10 +15540 11-2 71-1 3-7 715 27 1.20 -5 +10541 11-2 72-1 3-1 713 26 1.19 -10 +7______________________________________
Examples 542 to 549
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-4) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 74, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 74.
TABLE 74______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________542 11-2 71-1 3-1 699 18 1.08 -10 +10543 11-2 71-2 3-1 712 20 1.05 -11 +9544 11-2 71-3 3-1 702 19 1.05 -8 +8545 11-11 71-1 3-1 714 19 1.08 -9 +8546 13-2 71-1 3-1 708 17 1.07 -10 +10547 11-2 71-1 3-3 711 15 1.07 -7 +11548 11-2 71-1 3-7 698 20 1.08 -8 +10549 11-2 72-1 3-1 701 19 1.06 -12 +9______________________________________
Examples 550 to 557
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 75, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 75.
TABLE 75______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________550 11-2 71-1 3-1 702 39 1.22 -7 +2551 11-2 71-2 3-1 691 40 1.20 -8 +1552 11-2 71-3 3-1 695 35 1.18 -5 .+-.0553 11-11 71-1 3-1 701 38 1.20 -4 +5554 13-2 71-1 3-1 710 40 1.21 -8 +3555 11-2 71-1 3-3 711 37 1.18 -7 +3556 11-2 71-1 3-7 712 36 1.20 -3 +1557 11-2 72-1 3-1 714 36 1.19 -4 +2______________________________________
Examples 558 to 565
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 76, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 76.
TABLE 76______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________558 11-2 71-1 3-1 706 30 1.10 -10 .+-.0559 11-2 71-2 3-1 713 35 1.08 -9 +5560 11-2 71-3 3-1 704 30 1.10 -8 +3561 11-11 71-1 3-1 695 36 1.12 -8 +1562 13-2 71-1 3-1 698 37 1.10 -9 +4563 11-2 71-1 3-3 694 32 1.09 -5 +2564 11-2 71-1 3-7 708 34 1.07 -10 +2565 11-2 72-1 3-1 702 32 1.11 -9 +4______________________________________
Examples 566 to 573
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 502 to 509 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-7) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the diphenoquinone derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 77, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 77.
TABLE 77______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________566 11-2 71-1 3-1 714 32 1.20 -7 .+-.0567 11-2 71-2 3-1 698 30 1.18 -5 +5568 11-2 71-3 3-1 710 28 1.17 -7 +4569 11-11 71-1 3-1 700 35 1.15 -6 +2570 13-2 71-1 3-1 705 38 1.17 -8 +2571 11-2 71-1 3-3 708 34 1.18 -8 +2572 11-2 71-1 3-7 709 39 1.18 -9 +1573 11-2 72-1 3-1 694 38 1.17 -7 .+-.0______________________________________
Examples 574 to 583
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 224 to 233 except for using 50 parts by weight of the naphthylenediamine derivative in combination with 50 parts by weight of the phenylenediamine derivative as the hole transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 78, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 78.
TABLE 78______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________574 11-2 71-1 4-2 704 62 1.22 -13 -5575 11-2 71-2 4-2 701 60 1.20 -15 -6576 11-2 71-3 4-2 700 63 1.22 -14 -8577 11-2 71-1 4-1 696 65 1.23 -15 -6578 11-2 71-1 4-3 699 68 1.25 -11 -5579 11-2 71-1 4-4 700 68 1.25 -13 +8580 11-11 71-1 4-1 703 64 1.24 -15 -6581 11-11 71-1 4-2 706 61 1.21 -16 -7582 13-2 71-1 4-3 705 67 1.25 -17 -4583 13-2 72-1 4-4 701 68 1.25 -15 +5______________________________________
Examples 584 to 593
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 574 to 583 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 79, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 79.
TABLE 79______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________584 11-2 71-1 4-2 700 30 1.10 -5 .+-.0585 11-2 71-2 4-2 700 33 1.13 -4 -2586 11-2 71-3 4-2 698 32 1.11 -3 -3587 11-2 71-1 4-1 695 33 1.12 -6 -6588 11-2 71-1 4-3 705 40 1.16 -5 -5589 11-2 71-1 4-4 701 42 1.17 -5 +5590 11-11 71-1 4-1 706 35 1.15 -6 -5591 11-11 71-1 4-2 700 33 1.12 -3 -2592 13-2 71-1 4-3 704 38 1.15 -2 -3593 13-2 72-1 4-4 700 37 1.15 -5 +5______________________________________
Examples 594 to 603
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 574 to 583 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 80, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 80.
TABLE 80______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________594 11-2 71-1 4-2 705 28 1.08 .+-.0 .+-.0595 11-2 71-2 4-2 703 31 1.08 .+-.0 +2596 11-2 71-3 4-2 707 33 1.10 .+-.0 -3597 11-2 71-1 4-1 695 35 1.12 -5 -5598 11-2 71-1 4-3 693 37 1.12 -5 -5599 11-2 71-1 4-4 701 40 1.15 -5 +5600 11-11 71-1 4-1 700 32 1.08 -6 -5601 11-11 71-1 4-2 700 30 1.00 .+-.0 .+-.0602 13-2 71-1 4-3 704 36 1.12 -4 -3603 13-2 72-1 4-4 707 35 1.15 -7 +5______________________________________
Examples 604 to 613
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 574 to 583 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 81, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 81.
TABLE 81______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________604 11-2 71-1 4-2 695 40 1.15 .+-.0 +2605 11-2 71-2 4-2 700 43 1.17 -6 +4606 11-2 71-3 4-2 704 41 1.15 -5 +3607 11-2 71-1 4-1 701 43 1.17 -4 +2608 11-2 71-1 4-3 700 45 1.20 -7 +1609 11-2 71-1 4-4 693 46 1.20 -8 +6610 11-11 71-1 4-1 705 43 1.16 -5 +3611 11-11 71-1 4-2 708 44 1.17 -3 -2612 13-2 71-1 4-3 700 46 1.20 -10 +3613 13-2 72-1 4-4 704 46 1.20 -10 +8______________________________________
Examples 614 to 623
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 574 to 583 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the ethylated nitrofluorenonimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 82, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 82.
TABLE 82______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________614 11-2 71-1 4-2 706 44 1.13 -5 -5615 11-2 71-2 4-2 707 42 1.13 -4 -3616 11-2 71-3 4-2 699 45 1.16 -5 -4617 11-2 71-1 4-1 700 44 1.16 -6 -3618 11-2 71-1 4-3 695 48 1.18 -8 +4619 11-2 71-1 4-4 704 47 1.20 -10 +9620 11-11 71-1 4-1 700 45 1.14 -10 -5621 11-11 71-1 4-2 705 43 1.12 -5 -3622 13-2 71-1 4-3 703 48 1.13 -8 +3623 13-2 72-1 4-4 701 49 1.14 -12 +10______________________________________
Examples 624 to 631
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 274 to 280 except for using 50 parts by weight of the naphthylenediamine derivative in combination with 50 parts by weight of the phenylenediamine derivative as the hole transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 83, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 83.
TABLE 83______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________624 11-2 71-1 5-1 708 69 1.13 -9 +3625 11-2 71-2 5-1 705 62 1.10 -5 +5626 11-2 71-3 5-1 702 68 1.13 -10 +3627 11-2 71-1 5-4 695 65 1.12 -6 +1628 11-11 71-1 5-1 697 63 1.11 -6 +1629 11-11 71-1 5-4 701 63 1.11 -7 +4630 13-2 71-1 5-1 704 68 1.13 -10 +5631 13-2 71-1 5-4 704 70 1.15 -10 +5______________________________________
Examples 632 to 639
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 624 to 631 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 84, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 84.
TABLE 84______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________632 11-2 71-1 5-1 699 48 1.00 -12 +8633 11-2 71-2 5-1 703 42 0.98 -13 +6634 11-2 71-3 5-1 702 40 0.96 -15 +10635 11-2 71-1 5-4 709 48 0.99 -10 +5636 11-11 71-1 5-1 698 45 0.99 -10 +4637 11-11 71-1 5-4 701 46 0.99 -13 +7638 13-2 71-1 5-1 704 45 0.99 -11 +6639 13-2 71-1 5-4 706 47 0.99 -16 +10______________________________________
Examples 640 to 647
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 624 to 631 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 85, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 85.
TABLE 85______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________640 11-2 71-1 5-1 703 41 1.00 -16 +7641 11-2 71-2 5-1 702 40 1.00 -15 +9642 11-2 71-3 5-1 695 38 0.99 -10 +5643 11-2 71-1 5-4 700 42 1.00 -13 +6644 11-11 71-1 5-1 702 40 1.00 -11 +3645 11-11 71-1 5-4 702 45 1.02 -13 +6646 13-2 71-1 5-1 706 41 1.00 -14 +10647 13-2 71-1 5-4 700 43 1.00 -14 +8______________________________________
Examples 648 to 655
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 624 to 631 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 86, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 86.
TABLE 86______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________648 11-2 71-1 5-1 701 43 1.00 -12 +6649 11-2 71-2 5-1 698 45 1.02 -14 +7650 11-2 71-3 5-1 700 41 1.00 -16 +10651 11-2 71-1 5-4 705 43 1.00 -15 +9652 11-11 71-1 5-1 697 42 1.00 -15 +8653 11-11 71-1 5-4 699 42 1.00 -13 +6654 13-2 71-1 5-1 700 40 1.00 -11 +4655 13-2 71-1 5-4 703 45 1.03 -16 +7______________________________________
Examples 656 to 663
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 624 to 631 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 87, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 87.
TABLE 87______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________656 11-2 71-1 5-1 700 46 1.02 -15 +10657 11-2 71-2 5-1 699 43 1.00 -13 +8658 11-2 71-3 5-1 704 45 1.02 -18 +11659 11-2 71-1 5-4 703 43 1.00 -15 +9660 11-11 71-1 5-1 704 42 1.00 -16 +8661 11-11 71-1 5-4 706 43 1.00 -13 +6662 13-2 71-1 5-1 694 46 1.03 -15 +7663 13-2 71-1 5-4 700 45 1.03 -15 +7______________________________________
Examples 664 to 671
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 309 to 317 except for using 50 parts by weight of the naphthylenediamine derivative in combination with 50 parts by weight of the phenylenediamine derivative as the hole transferring material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 88, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 88.
TABLE 88______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________664 11-2 71-1 6-3 702 60 1.32 -16 +6665 11-2 71-2 6-3 700 63 1.33 -13 +5666 11-2 71-3 6-3 705 65 1.36 -11 +8667 11-2 71-1 6-10 701 69 1.40 -16 +8668 11-11 71-1 6-3 694 63 1.35 -15 +9669 11-11 71-1 6-6 707 75 1.45 -14 +7670 13-2 71-1 6-3 699 62 1.30 -10 +5671 13-2 71-1 6-10 701 70 1.35 -14 +7______________________________________
Examples 672 to 679
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 664 to 671 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-1) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 89, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 89.
TABLE 89______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________672 11-2 71-1 6-3 700 38 1.08 -10 +4673 11-2 71-2 6-3 694 35 1.08 -12 +7674 11-2 71-3 6-3 697 35 1.08 -10 +5675 11-2 71-1 6-10 699 45 1.15 -15 +9676 11-11 71-1 6-3 702 39 1.10 -13 +4677 11-11 71-1 6-6 706 50 1.20 -17 +10678 13-2 71-1 6-3 700 40 1.12 -10 +3679 13-2 71-1 6-10 700 47 1.19 -15 +6______________________________________
Examples 680 to 687
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 664 to 671 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-3) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 90, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 90.
TABLE 90______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________680 11-2 71-1 6-3 703 27 1.00 -3 .+-.0681 11-2 71-2 6-3 700 28 1.00 .+-.0 +4682 11-2 71-3 6-3 702 30 1.05 -5 +3683 11-2 71-1 6-10 698 36 1.07 -7 +2684 11-11 71-1 6-3 701 26 1.00 -4 +4685 11-11 71-1 6-6 706 40 1.10 -13 +6686 13-2 71-1 6-3 703 30 1.05 -5 +5687 13-2 71-1 6-10 700 35 1.06 -8 +5______________________________________
Examples 688 to 695
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 664 to 671 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-5) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 91, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 91.
TABLE 91______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________688 11-2 71-1 6-3 702 40 1.10 -8 +4689 11-2 71-2 6-3 701 43 1.11 -6 +3690 11-2 71-3 6-3 697 47 1.16 -10 +5691 11-2 71-1 6-10 695 47 1.16 -8 +5692 11-11 71-1 6-3 700 45 1.13 -8 +5693 11-11 71-1 6-6 700 50 1.21 -12 +10694 13-2 71-1 6-3 701 45 1.17 -6 +3695 13-2 71-1 6-10 706 46 1.16 -11 +9______________________________________
Examples 696 to 703
(Single-layer type electrophotosensitive material for analogue light source)
According to the same manner as that described in Examples 664 to 671 except for using 5 parts by weight of the bisazo pigment represented by the above formula (10-6) as the electric charge generating material, a single-layer type electrophotosensitive material for analogue light source was produced.
The amount of the tryptoanthrinimine derivative was 30 parts by weight in all Examples. In addition, the hole transferring materials and electron transferring materials used in the Examples are shown by the number of the above compounds in Table 92, according to the same manner as that described above.
The electrophotosensitive materials of the above respective Examples were subjected to the above initial electric characteristics test (II) and electric characteristics test (II) after repeated exposure, and their characteristics were evaluated. The results are shown in Table 92.
TABLE 92______________________________________ Initial AfterExample Characteristics RepeatingNo. HTM ETM V.sub.0 Vr E.sub.1/2 .DELTA.V.sub.0 .DELTA.Vr______________________________________696 11-2 71-1 6-3 701 38 1.10 -8 +5697 11-2 71-2 6-3 698 39 1.12 -7 +5698 11-2 71-3 6-3 694 40 1.10 -8 +2699 11-2 71-1 6-10 705 44 1.15 -12 +6700 11-11 71-1 6-3 705 42 1.13 -5 +2701 11-11 71-1 6-6 706 49 1.22 -18 +10702 13-2 71-1 6-3 704 41 1.10 -9 +3703 13-2 71-1 6-10 700 46 1.16 -15 +9______________________________________

Number	Date	Country
6-252399	Oct 1994	JPX
7-022572	Feb 1995	JPX
7-120688	Apr 1995	JPX

Number	Name	Date	Kind
3461165	Frye	Aug 1969
4666810	Umehara et al.	May 1987

Number	Date	Country
0650955	May 1995	EPX
62-018566	Jan 1987	JPX
03121889	May 1991	JPX
A04118286	Apr 1992	JPX
A05038877	Feb 1993	JPX
05080550	Apr 1993	JPX

Naphthylenediamine derivative and electrophotosensitive material using the same

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