BR102013016921A2 - PHOTO-SENSITIVE ELECTRO-PHOTOGRAPHIC COMPONENT, PROCESS CARTRIDGE AND ELECTRO-PHOTOGRAPH MECHANISM - Google Patents

Abstract

photosensitive electrophotographic component, process cartridge and electrophotographic mechanism. an electrophotographic photosensitive component has a laminate body, and a gap-carrying layer formed on the laminate body, wherein the laminate body is a laminate body having a conductive support, an electron transport layer and a charge generating layer. when an impedance is measured by forming a circular gold electrode having a thickness of 300 nm and a diameter of 10 mm on a surface of the charge-generating layer of the cathodic sublimation laminated body, and applying an alternating electric field. 100 mv and 0.1 Hz between the conductive support and the electrode of another, the laminated body of the electrophotographic photosensitive component satisfies the following expression (1): r_opt / r_dark <0.95 (1)

Description

“ELECTROPHOTOGRAPHIC PHOTOSSENSITIVE COMPONENT, PROCESS CARTRIDGE AND ELECTROPHOTOGRAPHIC MECHANISM”

BACKGROUND OF THE INVENTION

Field of the Invention

The present invention relates to an electrophotographic photosensitive component, and a process cartridge and an electrophotographic mechanism having an electrophotographic photosensitive component.

Description of the Related Art

As electrophotographic photosensitive components used for process cartridges and electrophotographic mechanisms, electrophotographic photosensitive components containing an organic photoconductive substance mainly prevail at present. The electrophotographic photosensitive component usually has a support and a photosensitive layer formed on the support. Then, a base layer is provided between the support and the photosensitive layer, in order to suppress load injection on the support side on the side of the photosensitive layer (load-generating layer) and to suppress the generation of image defects such as the veiling.

Load-bearing substances having a higher sensitivity have recently been used. However, such a problem arises in which a charge is likely to be retained in a photosensitive layer due to the fact that the amount of charge generated becomes large together with the higher sensitivity formation of the charge-generating substance, es double image it is likely to occur. Specifically, a phenomenon of a so-called positive double image, in which the density of only the parts irradiated with light in the previous rotation time becomes high, is likely to occur in a printed image.

A technology to reduce such a double image phenomenon is disclosed in which a base layer is produced to be a layer (hereinafter also referred to as an electron transport layer) having an electron transport capacity by incorporating a electron transport substance in the base layer. National Publication of International Patent Application No. 2009-505156 discloses a condensed polymer (electron transport substance) having an aromatic tetracarbonylbisimide backbone and a crosslinking site, and an electron transport layer containing a polymer with an agent crosslinking. Japanese Open Patent Application No. 2003-330209 discloses that a polymer of an electron transport substance having a non-hydrolyzable polymerizable functional group is incorporated into a base layer. Japanese Open Patent Application No. 2005-189764 discloses a technology for forming the electron mobility of a base layer to be 10 ' ⁷ cm ² / V sec or more in order to improve the ability to

2/77 electron transport.

The demand for the quality of electrophotographic images has recently been increasingly high, and the allowable range for the initial positive double image and the long term positive double image after repeated use has become extremely strict. As a result of exhaustive studies by the present inventors, it was observed that with regard to the reduction of the double positive image, the technologies disclosed in the National Publication of the International Patent Application No. 2009-505156 and in the Japanese Patent Applications Open to the Public We. 2003-330209 and 2005-189764 still have room for improvement.

SUMMARY OF THE INVENTION

It is an objective of the present invention to provide a reduced electrophotographic photosensitive component in the positive double image at the initial stage and after repeated long-term use, and a process cartridge and an electrophotographic mechanism having the electrophotographic photosensitive component.

The present invention relates to an electrophotographic photosensitive component including a laminated body and a gap transport layer formed in the laminate body, in which the laminated body has a conductive support, an electron transport layer formed on the transport layer of electrons, and a charge-generating layer formed over the electron transport layer; and the laminated body meets the following expressions (1):

R_opt / R_dark <0.95 (1), where, in the expression above (1), R_opt represents the impedance of the laminated body measured by the steps of: forming, on a surface of the charge generation layer, a gold-shaped electrode circular having a thickness of 300 nm and a diameter of 10 mm through cathodic sublimation, and apply, between the conductive support and the electrode of another in circular form, an alternating electric field having a voltage of 100 mV and a frequency of 0, 1 Hz while radiating the surface of the load generation layer with light having an intensity of 30 pJ / cm ² sec, and measuring the impedance, and R_dark represents the impedance of the laminated body measured by the steps of: forming, on a surface of the layer of charge generation, an electrode of another in circular shape having a thickness of 300 mm and a diameter of 10 mm by cathodic sublimation, and applying, between the conductive support and the electrode of another in circular shape, an alternating electric field having a voltage m of 100 mV and a frequency of 0.1 Hz without radiating the surface of the charge-generating layer with light, and measure the impedance.

The present invention also relates to a process cartridge that can be detachable and detachable to a main body of an electrophotographic mechanism, in which the process cartridge fully supports: the photosensitive electrophotographic component,

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- and at least one unit selected from the group consisting of a loading unit, a developing unit, a transfer unit and a cleaning unit. The present invention also relates to an electrophotographic mechanism having the 5 photosensitive electrophotographic component, and a charge unit, a light irradiation unit, a development unit and a transfer unit. The present invention can provide a reduced electrophotographic photosensitive component in the positive double image at the initial stage and after repeated long-term use, and a process cartridge and an electrophotographic mechanism having the component 10 photosensitive electrophotographic. Other aspects of the present invention will become apparent from the following description of the exemplary embodiments with reference to the accompanying drawings. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a diagram illustrating an example of a constitution of the outline of 15 a determination mechanism for carrying out a determination method in accordance with the present invention. FIG. 2 is a diagram that illustrates the typical examples of R_dark and R_opt when the V determination method according to the present invention is carried out. FIG. 3 is a diagram illustrating an outline of a mechanism 20 electrophotographic having a process cartridge that has an electrophotographic photosensitive component. FIG. 4 is a diagram for describing an image for the double image evaluation used in the double image evaluation. FIG. 5A is a diagram to describe a standard Keima image of a single 25 point (similar to the rider's movement). FIG. 5B is a diagram to describe a standard single point image used after repeated long-term use. FIG. 6 is a diagram illustrating an example of a layer formation of the electrophotographic photosensitive component. 30 DESCRIPTION OF METHODS Preferred embodiments of the present invention will now be described in detail according to the accompanying drawings. First, a determination method (hereinafter also referred to as the "determination method according to the present invention") to determine whether or not 35 an electrophotographic photosensitive component satisfies the relationship of the above expressions (1) of the present invention will be described. The conditions of temperature and humidity when the method of determination according to the present invention is carried out, may be under the environment of use of an electrophotographic mechanism having a photosensitive component

4/77.

electrophotographic. The condition can be under the normal temperature and normal humidity environment (23 ° C ± 3 ° C, 50% ± 2% RH). The measurement method involves the use of a laminated body having a support, an electron transport layer and a charge generation layer in that order.

At this point, a gap transport layer is extracted by peeling off an electrophotographic photosensitive component having a laminated body and the gap transport layer formed on the laminate body to thereby produce a laminated body (hereinafter also referred to as “component photosensitive electrophotographic for determination ”), which can be used as an object of determination. A method of scaling a gap transport layer includes a method in which an electrophotographic photosensitive component is immersed in a solvent that dissolves the gap transport layer and hardly dissolves an electron transport layer and a charge generation layer, and a method in which the gap transport layer is crushed.

As a solvent that dissolves a gap transport layer and hardly dissolves an electron transport layer and a charge generating layer, a solvent used in a coating liquid for the gap transport layer can be used. The solvent types will be described later. An electrophotographic photosensitive component is immersed in the solvent for a gap transport layer to be dissolved in the solvent, and thereafter dried to thereby obtain an electrophotographic photosensitive element for completion. Such a gap transport layer that may have been extracted by flaking can be confirmed, for example, by which no resin component of the gap transport layer can be observed by the ATR method (total reflection method) in the measurement method of FTIR.

A method of shredding a gap transport layer involves, for example, the use of a drum and tape shredding mechanism produced by Canon Inc. and the use of a polishing tape (C2000, produced by Fujifilm Corp.). At this point, the measurement can be carried out at the moment when the entire gap transport layer is removed while the thickness of the gap transport layer is successively measured so that it is not crushed to a load-generating layer due to excessive crushing of the gap. transport layer of gaps and the surface of an electrophotographic photosensitive component being observed. The case where the thickness of the load-generating layer of 0.10 pm or more is left after crushing has been carried out until the load-generating layer has been found to provide almost the same value by the determination method mentioned above as in the case where crushing is not carried out until the load generation layer. Therefore, even if not only a gap transport layer, but even a load-generating layer is

5/77 crushed, in the case where the thickness of the load generation layer is 0.10 pm or more, the above mentioned determination method can be used.

FIG. 1 illustrates an example of a draft constitution of a determination mechanism for carrying out the determination method in accordance with the present invention. In FIG. 1, the reference numeral 101 indicates a part of an electrophotographic photosensitive component for determination (laminated body) obtained by cutting the electrophotographic photosensitive component for determination in 2 cm (peripheral direction) x 4 cm (long axis direction). The reference numeral 102 indicates a gold electrode in circular shape having a diameter of 10 mm and a thickness of 300 mm formed on a surface of a layer of charge generation of the aforementioned laminated body. A method for cathodic sublimation of a gold electrode is not particularly limited, but a Quick Auto Coater (SC-707AT) produced by SANYU Electronic Co., Ltd., or the like can be used. Cathodic sublimation is performed until the thickness of a gold electrode becomes 300 mm while a 20 mA discharge current is maintained with a constitution in which a gold target disposed on a surface of the charge generation layer, for thereby manufacturing the gold electrode. Reference number 103 indicates an impedance measuring instrument, and it is shown that a lead wire 105 is connected to the gold electrode on the charge generation layer and the conductive support. The reference number 104 indicates a mechanism for oscillating the laser light (mechanism for carrying out the radiation of light), and the reference number 106 indicates the radiation light. As the impedance measuring instrument, for example, a measurement module being a combination of SI-1287-electromechanical interface, SI-1260-impedance gain phase analyzer and 1296-dielectric interface, produced by Toyo Corp., is used . The impedance (R_dark) under the condition without light irradiation in the present invention is measured by covering the magnet mechanism of FIG. 1 with a blackout film to protect the interior light, without irradiation of light by the mechanism 104 to oscillate the laser light. Then, an alternating electric field of 100 mV is applied between the conductive support of the laminated body and the gold electrode, and the impedance is measured by scanning the frequency from a high frequency of 1 MHz to a low frequency of 0, 1 Hz to acquire an impedance (R_dark) at 0.1 Hz. That is, the impedance indicates an impedance measured by applying an alternating electric field of 100 mV and 0.1 Hz between the conductive support of the laminated body and the gold electrode under the condition without irradiation of a surface of the charge generation layer with light.

Then, the impedance (R_opt) under the light irradiation condition is measured as in the above mentioned case without light irradiation, except to continuously oscillate the light irradiation 106 from the mechanism 104 to oscillate the laser light in the electrophotographic photosensitive component for determination 101. With respect to the

6/77 irradiation when the R_opt is measured, light of a wavelength suitable for the light-absorbing property of the load-generating layer is used, and irradiation with the light having an intensity sufficient to saturate the layer-generating layer. charge with carriers excited by the light generated from a charge-generating substance is carried out. Specifically, with light irradiation having a wavelength of 400 nm to 800 nm and an irradiation intensity of 30 pJ / cm ² sec or more, light-excited carriers can be sufficiently saturated. Examples of the present invention used such as an irradiation intensity where the impedance (R_opt) under irradiation of light is saturated at the lowest value. Specifically, irradiation with laser light having a wavelength of 680 nm, and an irradiation intensity of 30 pj / cm ² sec was performed. As for a light irradiation time, irradiation of light with the above irradiation intensity over a period of 1 second or longer can provide sufficient saturation of light-excited carriers, but the impedance measurement takes several minutes. The impedance is measured while the light irradiation is carried out at the intensity of irradiation above, with the result that carriers excited by light are sufficiently saturated. That is, impedance means an impedance measured by applying an alternating electric field of 100 mV and 0.1 Hz between the conductive support and the gold electrode under the condition of irradiation of the surface of the charge generation layer with light having an irradiation intensity of 30 pj / cm ² sec · Whether or not the electrophotographic photosensitive component satisfies the relationship of expression (1) above can be determined by calculating the ratio of the measured R_dark and R_opt.

FIG. 2 illustrates typical examples of R_dark and R_opt. In FIG. 2, the frequency dependence of the impedances (R_dark and R_opt) measured by the method above is illustrated. Particularly on the low frequency side, the change in impedance becomes large, depending on the presence and absence of light irradiation. That is, the R_opt / R_dark ratio at 0.1 Hz indicates 0.95 or less.

In the present invention, in order to reduce the positive double image at the initial stage and after repeated use, the R_opt / R_dark ratio is 0.95 or less. The present inventors assume the reason that satisfying the relationship of the expression above (1) can reduce the double positive image at the initial stage and after repeated use, as follows.

That is, in the case of an electrophotographic photosensitive component supplied with an electron transport layer (base layer), a charge generating layer and a gap transport layer on a support in this order, in parts where the irradiation light (image radiation light) falls, without the charges (gaps and electrons) generated in the charge generation layer, the gaps are injected into the gap transport layer, and the electrons are injected into the electron transport layer and transferred to

7/77 the support. However, if the electrons generated in the charge-generating layer by light excitation do not move completely in the electron transport layer before the next charge, the charge is retained in the charge-generating layer, further motivating the electron movement even during the next load. Slow moving electrons are likely to cause a local decrease in the carrying capacity of parts irradiated with light after the next charge. These phenomena are also caused by the repeated use of an electrophotographic photosensitive component, and the charge retained in the charge-generating layer is likely to increase gradually. The charge retained in the load-generating layer performs the cause of generating the double positive image in the initial phase and after repeated use.

So, if the laminated body satisfies the relation of the expression (1) above, the reception and release of electrons (electrons derived from light excitation and retained in the charge-generating layer) in slow motion at the interface between the electron transport layer and the load generation layer is conceivably promoted. That is, in the determination method according to the present invention, if the resistance between the conductive support and the gold electrode does not change depending on the presence and absence of light irradiation in the state in which the load-generating layer of the laminated body is saturated with the charge derived from light excitation, it is expressed that the electron injection from the charge generation layer into the electron transport layer is insufficient, and slow moving electrons are likely to be retained in the generation layer. charge. Then, it is conceivable that the trend corresponds to the case where R_opt / R_dark is 0.96 or more. Conversely, if the resistance between the conductive support and the gold electrode decreases by irradiation of light in the state in which the charge-generating layer is saturated with electrons (charge derived from light excitation) in slow motion, it is conceivable that the injection of electrons from the charge-generating layer to the electron transport layer is sufficiently accomplished, and the retention of slow-moving electrons in the charge-generating layer can be reduced.

The state of electron retention in slow motion can be clarified by paying attention to impedance at low frequencies. Although 0.1 Hz is considered to be a low frequency in the evaluation method according to the present invention, it is conceivable that any frequency can express the impedance of slow moving electrons, as long as the frequency is a lower frequency lower than 0.1 Hz. In the present invention, the slow moving electron impedance is observed using the 0.1 Hz impedance. 0.1 Hz is a period of about 10 sec, and a state is conceivably expressed in which the electrons that respond to the electric field over a period of 10 sec are retained in the charge-generating layer through repeated use, and the double positive image is likely to occur.

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It is conceivable that if the relationship of expression (1) has been satisfied, such a state of good injection capacity in which the slow-moving electron retention is reduced is presented, and in repeated use, the electron retention in the initial stage and after repeated use in the charging-light irradiation process is reduced to allow the reduction of the positive double image. As shown in the Comparative Examples described below, although the electrophotographic photosensitive components of the National Publication of International Patent Application No. 2009-505156 and others have a sufficient conductivity of electron transport layers, since slow moving electrons are susceptible of being retained in the charge generation layers, R_opt / R_dark becomes higher than 0.95, and the double positive image after repeated use is likely to occur in some cases.

It is also conceivable that a technology of Japanese Open Patent Application No. 2005-189764 in which the electron mobility of a base layer (electron transport layer) is determined to be 10 ' ⁷ cm ² / V sec or but it has an objective of improving the movement of electrons for faster movement, and does not solve the cause of the double positive image due to the retention of slow moving electrons. Japanese Open Patent Application No. 2010-145506 discloses that the charge mobility of a gap transport layer and an electron transport layer (base layer) is established to be in specific ranges, but does not resolve the cause of the generation of the double positive image as in the Japanese Open Patent Application No. 2005-189764. Additionally, in these patent literature, the measurement of electron mobility in an electron transport layer is performed using a constitution in which an electron transport layer is formed over a charge generation layer, whose constitution is inverse to the constitution of a layer used in an electrophotographic photosensitive component. However, such a measurement cannot be said to be able to sufficiently assess the movement of electrons in an electron transport layer of an electrophotographic photosensitive component.

For example, in the case where an electron transport layer is produced by incorporating an electron transport substance into a base layer, when the coating liquids from a charge generation layer and a gap transport layer like upper layers are applied to form the charge generation layer and the gap transport layer, the electron transport substance elutes in some cases. It is conceivable in this case that even if the electron mobility is measured by preparing the electron transport layer and the charge-generating layer as inverted layers as described above, since the electron transport substance elutes in a photosensitive component

9/77 electrophotographic, the electron movement of the electron transport layer of the electrophotographic photosensitive component cannot be sufficiently evaluated. Therefore, it is believed that the determination needs to be carried out using an electron transport layer from which a gap transport layer was extracted and a charge generation layer after the charge generating layer and the transport layer of gaps are formed in the electron transport layer.

The electrophotographic photosensitive component according to the present invention has a laminated body, and a gap transport layer formed on the laminate body, and the laminated body has a conductive support, an electron transport layer formed on the conductive support, and a charge generation layer formed over the electron transport layer. FIG. 6 is a diagram illustrating an example of a layer formation of the electrophotographic photosensitive component. In FIG. 6, reference number 21 indicates a conductive support; the reference number 22 indicates an electron transport layer; the reference number 23 indicates a load-generating layer; and the reference number 24 indicates a gap transport layer.

As a common electrophotographic photosensitive component, a cylindrical electrophotographic photosensitive component in which a photosensitive layer (a charge-generating layer, a gap transport layer) is formed on a cylindrical support is widely used, but otherwise in a way such as in a belt shape or a blade shape can be used.

Electron transport layer

The thickness of an electron transport layer can be 0.1 pm or more and

1.5 pm or less, and is most preferably 0.2 pm or more and 0.7 pm or less.

If the aforementioned laminated body satisfies the relationship of the following expression (2), a greater double positive image reduction effect is acquired. Since a lower value of R_opt / R_dark provides a greater effect of reducing the positive double image, the value is sufficient if the value is greater than 0.

^<R _ ° pt / R_dark <0.85 ·· expression (2)

The value most preferably satisfies the following expression (3).

0.60 <R_opt / R_dark <0.85 ... Expression (3)

In the expressions above (2) and (3), R_opt represents an impedance measured by the formation of a gold electrode in a circular shape having a thickness of 300 nm and a diameter of 10 mm on a surface of the charge-generating layer of the body laminated through cathodic sublimation, the application of an alternating electric field of 100 mV and 0.1 Hz between the conductive support and the gold electrode under the condition of irradiation of the surface of the charge generation layer with light having an irradiation intensity 30 pJ / cm ² sec, and impedance measurement. R_dark represents a

10/77 impedance measured by the formation of a gold electrode in a circular shape having a thickness of 300 nm and a diameter of 10 mm on a surface of the layer of charge generation of the laminated body through cathodic sublimation, by applying a field alternating electrical of 100 mV and 0.1 Hz, between the conductive support and the gold electrode under the condition without light irradiation from the surface of the load-generating layer, and the impedance measurement.

Then, the constitution of an electron transport layer will be described. An electron transport layer can contain an electron transport substance, or a polymer of an electron transport substance. The electron transport layer can further contain a polymer obtained by polymerizing a composition that includes an electron transport substance having polymerizable functional groups, a thermoplastic resin having polymerizable functional groups and a crosslinking agent.

Electron transport substance

Examples of electron transport substances include quinone compounds, imide compounds, benzimidazole compounds and cyclopentadienylidene compounds. An electron transport substance can be an electron transport substance having polymerizable functional groups. The polymerizable functional group includes a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group.

The following are specific examples of the electron transport substance. The electron transport substance includes compounds represented by one of the following formulas (A1) to (A9).

_R 101 _R 102 _r 209 _r 307

In formulas (A1) to (A9), R ¹⁰¹ to R ¹⁰⁶ , R ²⁰¹ to R ²¹⁰ , R ³⁰¹ to R ³⁰⁸ , R ⁴⁰¹ to R ⁴⁰⁸ , R ⁵⁰¹ to

R510 _d 601 _d 606 _d 701 „ _O 708 _D 801„ _D 810 „, -, 901 _ r-> 908 j.

, R to R, R to R, R aR and R to R each represent

11/77 independently a monovalent group represented by the following formula (A), a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkoxycarbonyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or substituted or unsubstituted heterocyclic group. One of the carbon atoms in the main chain of the alkyl group can be replaced by O, S, NH or NR ¹⁰⁰¹ (R ¹⁰⁰¹ is an alkyl group). The substituted alkyl group substituent includes an alkyl group, an aryl group, an alkoxycarbonyl group and a halogen atom. The substituted aryl group substituent and the substituted heterocyclic group substituent include a halogen atom, a nitro group, a cyano group, an alkyl group and an alkyl halide group. Z ²⁰¹ , Z ³⁰¹ , Z ⁴⁰¹ and Z ⁵⁰¹ each independently represent a carbon atom, a nitrogen atom or an oxygen atom. In the case where Z ²⁰¹ is an oxygen atom, R ²⁰⁹ and R ²¹⁰ are not present, and in the case where Z ²⁰¹ is a nitrogen atom, R ²¹⁰ is not present. In the case where Z ³⁰¹ is an oxygen atom, R ³⁰⁷ and R ³⁰⁸ are not present, and in the case where Z ³⁰¹ is a nitrogen atom, R ³⁰⁸ is not present. In the case where Z ⁴⁰¹ is an oxygen atom, R ⁴⁰⁷ and R ⁴⁰⁸ are not present, and in the case where Z ⁴⁰¹ is a nitrogen atom, R ⁴⁰⁸ is not present. In the case where Z ⁵⁰¹ is an oxygen atom, R ⁵⁰⁹ and R ⁵¹⁰ are not present, and in the case where Z ⁵⁰¹ is a nitrogen atom, R ⁵¹⁰ is not present.

m (A)

In formula (A), at least one of α, β and γ is a group having a substituent, and the substituent is at least one group selected from the group consisting of a hydroxyl group, a thiol group, an amino group , a carboxyl group and a methoxy group. I and m are each independently 0 or 1, and the sum of I and m is 0 or 2.

α represents an alkylene group having 1 to 6 atoms in the main chain, an alkylene group having 1 to 6 atoms in the main chain and being replaced with an alkyl group having 1 to 6 carbon atoms, an alkylene group having 1 to 6 atoms in the main chain and being replaced with a benzyl group, an alkylene group having 1 to 6 atoms in the main chain and being replaced with an alkoxycarbonyl group, or an alkylene group having 1 to 6 atoms in the main chain and being substituted with a phenyl group, and these groups can have at least one substituent selected from the group consisting of a hydroxy group, a thiol group, an amino group and a carboxyl group. One of the carbon atoms in the main chain of the alkylene group can be replaced by O, S, NH or NR ¹⁰⁰² (R ¹⁰⁰² is an alkyl group).

β represents a phenylene group, a phenylene group substituted with an alkyl group having 1 to 6 carbon atoms, a phenylene group substituted by the nitro group, a phenylene group substituted by the halogen group or a substituted phenylene group by the alkoxy group, and these groups can have at least one substituent

12/77 selected from the group consisting of a hydroxy group, a thiol group, an amino group and a carboxyl group.

γ represents a hydrogen atom, an alkyl group having 1 to 6 atoms in the main chain, or an alkyl group having 1 to 6 atoms in the main chain and being replaced with an alkyl group having 1 to 6 carbon atoms, and these groups can have at least one substituent selected from the group consisting of a hydroxy group, a thiol group, an amino group and a carboxyl group. One of the carbon atoms in the main chain of the alkyl group can be replaced by O, S, NH or NR ¹⁰⁰³ (R ¹⁰⁰³ is an alkyl group).

Among the electron transport substances represented by one of the formulas above from (A-1) to (A-9), electron transport substances are more preferable which have a polymerizable functional group and a monovalent group represented by the above formula (A) at least one of R ¹⁰¹ to R ¹⁰⁶ , at least one from R ²⁰¹ to R ²¹⁰ , at least one from R ³⁰¹ to R ³⁰⁸ , at least one from R ⁴⁰¹ to R ⁴⁰⁸ , at least one from r5 ° i θ r5w ρθ | θ minus one jg r6oi g ^ 606 ρθ | 0 minus one qe R ⁷⁰¹ to R ⁷⁰⁸ , at least one from RS ° 1 to R810 θ _{pe | Q minus one from R} 901 _{to R} 908

A polymer can be formed which is obtained by polymerizing a composition containing an electron transport substance having polymerizable functional groups, a thermoplastic resin having polymerizable functional groups and a crosslinking agent. One method for forming an electron transport layer involves forming a coating film of a coating liquid for the electron transport layer containing a composition that includes an electron transport substance having polymerizable functional groups, a resin thermoplastic having polymerizable functional groups and a crosslinking agent, and drying the coating film by heating to polymerize the composition to thereby form the electron transport layer. Thereafter, specific examples of electron transport substances having polymerizable functional groups will be described. The heating temperature when the coating film of a coating liquid for an electron transport layer is dried by heating can be from 100 to 200 ° C.

In the Tables, the symbol A is represented by the same structure as the symbol A, specific examples of the monovalent group are shown in the columns of A and A '.

In the following, specific examples of electron transport substances having polymerizable functional groups will be described. Specific examples of the compounds represented by the above formula (A1) are shown in Table 1-1, Table 1-2, Table

1-3 Table 1-4, Table 1-5 and Table 1-6. In the Tables, the case where γ for indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in

13/77 column of α or β.

Table 1-1

Compound example R ¹⁰¹ r’O2 _r 'O3 R ^'04 _r 1 ° 5 r’06 THE α 18 Ύ A1O1 H H H H h ₃ c__ THE h ₂ c-oh —CH —CHg - - A1 02 H H H H C2H5 í ⁷ THE h ₂ c-oh -cá Η ₂ ^ -ΟΗ ₃ - - A103 H H H H THE - H ₂ C-OH --- 0Η ₂ A104 H H H H CjHs THE - -ch ₂ -oh A1 05 H H H H C2H5 THE - --CH2-OH A106 H H H H ^ Ç ^ -n ° ₂ h ₃ c THE h ₂ c-oh-ca H; b-CH ₃ - - A1 07 H H H H THE h ₂ c-oh —CH ch ₃ - - A1 08 H H H H THE h ₂ c-oh -cá H ^ b —ch ₃ - - A1 09 H H H H h ₃ c__ THE --CgH-fQ — OH - - A110 H H H H —CgH 13 THE h ₂ c-oh —CH H ^ b — CH3 - - A111 H H H H c ₄ h ₉ —C-CH ^ 2 C2H5 THE - "O H ₂ C-OH - ”0Η ₂ A112 H H H H CaHs THE - - A113 H H H H C2H5 THE - R, - Al 14 H H H H CzHe THE - ^- O * ^-53 * - A115 H H H H Í ₅ í ⁷ THE - H2C-CH3 -cri booH - A116 H H H H C2H5 & THE  - —C-COOH h ₂ -

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Table 1-2

Example of xmposto R'0 ' R ¹⁰² r ^'03 _R 1 ° 4 R ¹⁰⁵ R ¹⁰⁶ THE The | 3 T A111 H H H H C2H5 í THE - - A118 H H H H C2H ₅ THE - 0- —C-COOH h ₂ A119 -Ό H H O C2H5 THE H ₂ C — OH —CH h ₂ ^ ~ ch ₃ - - A12O CN H H CN cjh; THE h ₂ c-oh-ca H ₂ b-CH ₃ - - A121 THE H H H h ₃ c h ₃ c - - -COOH A122 H NO _Z H no ₂ H ₃ C THE h ₂ c-oh -h h £ -ch ₃ - - A123 H H H H h ₃ c Φ CzHj THE h ₂ c-oh —CH η ₂ ^ -οη - - A124 H H H H THE THE h ₂ c-oh —CH Hjb-CHa - - Al 25 H H H H THE THE - B —CH ₂ -OH A126 H H H H THE THE - - A127 H H H H THE THE - B". - A128 H H H H THE THE - - Al 29 H H H H THE THE - h ₂ c-ch, -CÚ boOH - A130 H H H H THE THE - - A131 H H H H h ₃ c cXs THE h ₂ c-oh-c H ₂ b-OH - - A132 H H H H h ₃ c THE , OH h ₂ c-ch ₂ h ₂ c — n H ₂ C-ÓH ₂ H ₂ 'b-CH ₂ ' bH - - A133 H H H H "B C2 ^ THE h ₂ c — nh oh —CH ₂ H ₂ b-CH ch ₃ - -

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Table 1-3

Compound example R ¹⁰ ' R ¹⁰² _r 1 ° 3 _r 1 ° 4 _r 105 rí 06 THE The T A134 H H H H h ₃ c C2 »5 THE C83 —C — C82-O8 b8 ₃ - A135 H H H H THE THE P -CH H ₂ b-OH - - A136 H H H H THE THE -ίΓθ H ₂ b-OH - - A137 H H H H THE THE H ₂ C-C8 ₂ -θή CH-OH H ₂ C-CH ₂ - - A138 H H H H THE THE - 08 H ₂ C — ch ₂ —N H ₂ b — ch ₃ A139 H H H H THE h ₂ c-oh —CH H ₂ b — CH ₃ - - A140 H H H H THE H ₂ C — 08 -οή 8 ^ b-C8 ₃ - - A141 H H H H h ₂ c-ch ₂ -ch): h ₂ h ₂ c-ch ₂ THE H ₂ C — 08 -οή H ₂ b-CH ₃ - - A142 H H H H THE THE h ₂ c-oh -οή ^ bO-CH ₃ - - A143 CN H H CN CjHs THE ^H2 _z ^c_ O -CH H ₂ b-OH - - A144 H H H H —0284-0-0285 THE H ₂ C-OH -οή H ₂ b-CH ₃ - - A145 H H H H ^ jFcf ₃ THE —C ₂ 84-OC ₂ H4-OH - - A146 H H H H THE THE H2C-CH ₃ -οή boOH - - A147 H H H H -CH ₂ CH ₂ -Q THE 8 ₂ C — 08 -οή 8 ₂ b —C8 ₃ - - A148 H H H H 0 THE —C ₂ H 4 ^- O — C ₂ H 4 ^- 0 h - - A149 H H H H THE —C8 ₂ C8 ₂ - ~ O ~ ° ^h - A150 H H H H 0 ° ^ THE - COOH COOH - A151 H H H H THE THE - --- ch ₂ -oh

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Table 1-4

Compound example R ¹⁰¹ R ^'02 R ¹⁰³ _r 1 ° 4 R ¹⁰⁵ R ¹⁰⁸ THE THE' The β T The β T A152 H H H H THE THE' h ₂ c-oh -c / i h £ -ch ₃ - - fCH ₂ ^ -OH - - A153 H H H H THE THE' - —Ch ₂ -oh - - A154 H H H H THE THE' - -O —C-COOH h ₂ -C-COOH h ₂ - - A155 H H H H THE THE' - -θ- ° Ο ^Η 3 - -B --ch ₂ -oh - A156 H H H H THE THE' h ₂ c-oh -οή H ₂ b-CH ₃ - - —Ch ₂ -oh -

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Table 1-5

Compound example R ¹⁰¹ R ¹⁰² R ^1ce _R 1 ° 4 R ^1C6 Rl « THE α 13 Ύ A157 H H H H THE THE H ₂ C — OH -HC 'CH ₃ H ₂ C — CH ^x ch ₃ - - A158 H H H H THE THE H ₂ C — OH - <ch-ch ₂ / \ h ₃ c ch ₃ - - A159 H H H H THE THE K ₂ c — OH CH-CH3 H3C - - A160 H H H H —C ₆ H ₁₂ -OH THE H ₂ C — OH -HC 'CH ₃ H ₂ C — CH ch ₃ - - A161 H H H H h ₃ c C ₂ H ₅ THE H ₂ C — OH -HC _z ^ch 3 HjC — CH ch ₃ - - A162 H H H H THE THE h ₂ c — cooh -Hc ' _z ^CH 3 H ₂ C — CH ^x ch ₃ - - A163 H H H H CH, / ^—C \ Hj H? H ₂ H ₂ C — C -C -C -CH, THE - (yvs-CíHi-oH - - A164 H H H H THE THE H ₂ C — OH —HC 'H ₂ C — CH,' b — CHj - - A165 H H H H THE THE COOH / —CH h ₂ c — ch ₂ ^X c — 0 — CH, - - A166 H H H H —CjHí-O-CjHs THE h ₂ c — oh -HC ' _z CH ₃ h ₂ c — ch' ch ₃ - - A167 H H H H - C2H4-S- C2H5 THE h ₂ c — oh -H _C 'CH3 H ₂ C — CH ch ₃ - - A168 H H H H H —c ₂ h ₄ -nc ₄ h ₉ THE H ₂ C — OH -Hc ' _z ^CH 3 H ₂ C — CH \ CH ₃ - - A169 H H H H ch ₃ —CH H ₂ C-CH ₃ \ ^m 2 ^M 2 / H ₂ CC “C“ N \ H ₂ C — CH3 THE H ₂ C — OH —HC _z ^ch 3 H ₂ C — CH ^s ch ₃ - - A170 H H H H H ₂ C — O — C —CH3 / - ^CH HX “2 ^ c — o — c -ch ₃ o ^z THE H ₂ c — OH -HC _z ^CH 3 h ₂ c — CH ch ₃ - -

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Table 1-6

Compound example R ¹⁰¹ r ¹ ° 2 R ^10S R ¹⁰⁴ R ¹⁰⁵ R ¹⁰⁶ THE THE' α / 3 Ύ The β Ύ A171 Ή H H H THE THE' h ₂ c- oh - <HjC — CH ₃ - - HjC — OH -Hc 'CH ₃ HjC — CH ^x ch ₃ - - A172 H H H H THE THE' —C2H4-O-C2H4-OH - - H ₂ C — OH -HC ' _z ^gh 3 h ^ c — ch' ^, ch ₃ - - A173 H H H H THE THE' -C ₆ H ₁₂ -OH - - H ₂ c — OH -HC CHa H ₂ C — CH ^x ch ₃ - - A174 H H H H THE THE' H —C ₃ H _s -NC ₂ H ₄ -OH - - H ₂ C — OH —HC CH ₃ H ^ C — CH ^x ch ₃ - - A175 H H H H THE THE' - C2H4-O-C2H4-OH - - H ₂ C — OH --CH Jp — 0 — ch ₃ O - - A176 H H H H THE THE' - C ₂ H ₄ -OC ₂ H _r OH - - —CH h ₂ c— oh - - A177 H H H H THE THE' - C ₂ H ₄ -SC ₂ H ₄ -OH - - H ₂ C — OH -HC 'CH ₃ H ₂ C — CH ^x ch ₃ - - A178 H H H H THE THE' H ₂ c — OH X h ₂ c — ch ₂ ^x s — ch ₃ - - H ₂ C — OH -hc 'ch ₃ H $ C— CH ^x ch ₃ - - A179 H H H H THE THE' -O —CH J H ₂ C — OH - - h ₂ c — oh - HC 'CH ₃ H ₂ C — CH ^x ch ₃ - - A180 H H H H THE THE' H ₂ C — OH --CH \ C — O — CH ₃ - - h ₂ c — oh - HC _z ^ch 3 h ₂ c — CH ^x ch ₃ - - A181 H H H H THE THE' - c ₂ h ₄ -sc ₂ h ₄ -oh - - H ₂ C — OH - -

Specific examples of compounds represented by the above formula (A2) are shown in Table 2-1, Table 2-2 and Table 2-3. In the Tables, the case where γ for indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

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Table 2-1

Example of composition R ²⁰¹ R ²⁰² r? ° 3 R ²⁰⁴ _r ² ° 5 R ²⁰⁶ R ²⁰⁷ R ²⁰⁸ R ²⁰⁹ R ²¹⁰ ^ 201 THE α β Ύ A201 H H THE H H H H H - - 0 - -O- —Ch ₂ -oh A2O2 H H THE H H H H H - - 0 - --- ch ₂ -oh A204 H H THE H H H H H - - 0 - - A205 H H THE H H H H H - - 0 - -Q nh ₂ - A206 H H THE H H H H H - - 0 - ^ O ^ ^sh - A207 H H H H H H H H THE - N - h ₂ c-oh - • C ^Z H2 A2O8 H H H H H H H H THE - N - COOH - A2O9 H H H H H H H H THE - N - ~ O- - A21O H H H H H H H H THE - N h ₂ c-oh -οή h £ -ch ₃ - - A211 CH3 H H H H H H ch ₃ THE - N - -B H2C-OH —c ^z h ₂ A212 H Cl H H H H Cl H THE - N - h ₂ c-oh —ÓHj A213 H H H H O H H THE - N - -O H2C-OH —c ^z h ₂ A214 H H ò-c ₂ h ₅ H H Ò-c ₂ h ₅ H H THE - N - -B h ₂ c-oh —c ^z h ₂ A215 H H H no ₂ NO ₂ H H H THE - N - -B H2C-0H --- c ^z h ₂ A2I6 H H THE H H THE H H - - 0 - -O·· —Ch ₂ -oh A217 H H THE H H THE H H - - 0 - -

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Table 2-2

Compound example R ²⁰ ' R ²⁰² R ²⁰³ R ²⁰⁴ R ²⁰⁵ R ²⁰⁶ R ²⁰⁷ R ²⁰⁸ R ™ R ² ' ⁰ ^ 201 THE The Ύ A218 H H THE H H THE H H - - 0 - THE - A219 H H THE H H THE H H - - 0 - - A220 H H THE H H THE H H - - 0 h ₂ c-oh -οή h £ -ch ₃ - - A221 H H THE H H THE H H - - 0 h ₂ c-oh —ch ₂ - - A222 H H THE H H THE H H - - 0 - - COOH A223 H H THE H H THE H H - - 0 - - nh ₂ A224 H THE H H H H THE H - - O - O- —Ch ₂ -oh A225 H H THE H H THE H H CN CN ç - O- —Ch ₂ -oh A226 H H THE H H THE H H CN CN ç - - A227 H H THE H H THE H H CN CN ç - THE, - A228 H H THE H H THE H H CN CN ç - ^ CX ^sH - A229 H H THE H H THE H H CN O ç - —Ch ₂ * oh A230 H H THE H H THE H H bC ₂ H ₅ Ó-C ₂ H ₅ ç - O- —Ch ₂ -oh A231 H H H H H H H H THE THE ç - - COOH A232 H no ₂ H H H H NO _Z H THE - N - -O- h ₂ c-oh - 0 ^ 2 A233 H H H H THE H H - - 0 - —Ch ₂ * oh

Table 2-3

'Example of compound R ²⁰ ' R ²⁰² p203 R ²⁰⁴ R ²⁰⁵ R ²⁰⁸ R ²⁰⁷ R ²⁰⁸ R ²⁰⁹ R ²¹⁰ z ²⁰¹ THE THE' The β Ύ The β Ύ A234 H THE H H H H A ^- H - - 0 h ₂ c-oh-cy CH3 - - - —Ch ₂ -oh A235 H THE H H H H THE' H - - 0 - -B —CH ₂ -OH - (- ch ₂ ^ oh - - A236 H THE' H H H H THE' H - - 0 - —C-COOH h ₂ --- C-COOH h ₂ - -

Specific examples of compounds represented by the above formula (A3) are shown in Table 3-1, Table 3-2 and Table 3-3. In the Tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

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Table 3-1

Compound example R ³⁰ ' R ³⁰² R ³⁰³ R ³⁰⁴ R ³⁰⁵ R ³⁰⁶ R ³⁰⁷ R ³⁰⁸ ^ 301 THE The β T A301 H THE H H H H - - 0 - O- —Ch ₂ -oh A3O2 H THE H H H H - - 0 - —Ch ₂ -oh A3O3 H THE H H H H - - 0 - - A3O4 H THE H H H H - - 0 - - A3O5 H THE H H H H - - O - ^h G ^hsh - A3O6 H H H H H H THE - N - h ₂ c-oh —dH ₂ A307 H H H H H H THE - N - - A308 H H H H H H THE - N h ₂ c-oh -οή H ₂ b- ch ₃ - - A3O9 ch ₃ H H H H ch ₃ THE - N - H ₂ C-OH -0¼ A31O H H Gl Cl H H THE - N - h ₂ c-oh —0¼ A311 H O H H O H THE - N - -O h ₂ c-oh -0¼ A312 H -c ^? bC ₂ H ₅ H H -c ^? ò-c ₂ h ₅ H THE - N - H ₂ C-OH -0¼ A313 H H H H H H THE - N - -B H2C-0H —óh ₂ A314 H THE H H THE H - - 0 - ^ O ·· —Ch ₂ -oh A315 H THE H H THE H - - 0 - COOH -

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Table 3-2

Compound example R ³⁰ ' R ³⁰² _r 3 ° 3 R ³⁰⁴ R ³⁰⁵ R ³⁰⁶ R ³⁰⁷ R ³⁰⁸ ^ 301 THE The β T A316 H THE H H THE H - - 0 - - nh ₂ - A317 H THE H H THE H - - 0 - "O ^-5 " - A318 H THE H H THE H - - 0 H ₂ C-OH -οή H ₂ b-ch ₃ - - A319 H THE H H THE H - - 0 h ₂ c-oh —ch ₂ - - A320 H THE H H THE H - 0 - - COOH A321 H THE H H THE H - - 0 - - nh ₂ A322 H H THE THE H H - - 0 - O- —Ch ₂ -oh A323 H THE H H THE H CN CN ç - O- • --ch ₂ -oh A324 H THE H H THE H CN CN ç - - A325 H THE H H THE H CN CN ç - nh ₂ - A326 H THE H H THE H CN CN ç - - A327 H THE H H THE H CN -Ό ç - "O· —Ch ₂ -oh A328 H THE H H THE H -C ^? bC ₂ H ₅ - / bc ₂ H ₅ ç - "O· —Ch ₂ -oh A329 H H H H H H THE THE ç - - COOH A330 H H H H H H THE - N - h ₂ c — oh —óh ₂

Table 3-3

Compound example R ³⁰¹ R ³⁰² R ³⁰³ R ³⁰⁴ R ³⁰⁵ p3O6 _R 3 ° 7 R ³⁰⁸ ^ 301 THE THE' α β Ύ α β Ύ A331 H THE H H THE H H H 0 h ₂ c-oh -CH H; b-CH ₃ - - - -b> —Ch ₂ -oh A332 H THE' H H THE H H H O - -B —Ch ₂ -oh - (- ch ₂ ^ oh - - A333 H THE H H THE' H H H 0 - —C-COOH h ₂ —C-COOH h ₂ - -

Specific examples of compounds represented by the above formula (A4) are shown in Table 4-1 and Table 4-2. In the tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

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Table 4-1

• Example of compound R ⁴⁰¹ R ⁴⁰² O • sr IZ R ⁴⁰⁴ _r ⁴ ° 5 r ^40S R ⁴⁰⁷ r4 ° 8 ^ 401 THE The β T A401 H H THE H H H CN CN ç - O- —Ch ₂ -oh A4O2 H H THE H H H CN CN ç - --- ch ₂ -oh A403 H H THE H H H CN CN ç - - A404 H H THE H H H CN CN ç - - A405 H H THE H H H CN CN ç - -O ^-39 - A406 H H H H H H THE - N - h ₂ c-oh —c ^z h ₂ A4O7 H H H H H H THE - N - bOOH - A408 H H H H H H THE - N - ~ O ^sh - A409 H H H H H H THE - N H ₂ C — OH -οή H ₂ b — CH ₃ - - A41O ch ₃ H H H H ch ₃ THE - N - -B h ₂ c — oh —ch ₂ A411 H Cl H H Cl H THE - N - h ₂ c — oh —óh ₂ A412 H H O O H H THE - N - -B H ₂ C — OH -0 ⁴ ¾ A413 H H bc ₂ H ₅ bC ₂ H ₅ H H THE - N - H ₂ C — OH —ch ₂ A414 H H H H H H THE - N - -O h ₂ c-oh -ch ₂ A415 H H THE THE H H CN CN Ç - —Ch ₂ -oh

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Table 4-2

Compound example _r 4 ° ¹ R ⁴⁰² _r 403 R ⁴⁰⁴ _r ⁴ ° 5 R ⁴⁰⁶ R ⁴⁰⁷ R ⁴⁰⁸ ^ 401 THE α β T A416 H H THE THE H H CN CN ç - - A417 H H THE THE H H CN CN ç - -Q nh ₂ - A418 H H THE THE H H CN CN ç - - A419 H H THE THE H H CN CN ç h ₂ c-oh -cA H ₂ b- ch ₃ - - A420 H H THE THE H H CN CN ç H ₂ C — OH —ch ₂ - - A421 H H THE THE H H CN CN ç - - COOH A422 H H THE THE H H CN CN ç - - NI-12 A423 H THE H H THE H CN CN ç - 0- —Ch ₂ -oh A423 H H THE THE H H - - O - —-Ch ₂ -oh A424 H H THE THE H H - - 0 - - A425 H H THE THE H H - - O - nh ₂ - A426 H H THE THE H H - - 0 - -The “ ^sh - A427 H H THE THE H H CN ç - —CH ₂ -OH A428 H H THE THE H H oc ₂ h ₅ bc ₂ n ₅ ç - -O- --ch ₂ -oh A429 H H H H H H THE THE ç - - COOH A430 H H H THE H H CN CN ç - h ₂ c-oh —0η ₂ A431 H H —QtC ₄ H ₉ THE H H - N - H2C-OH —c'h ₂

Specific examples of compounds represented by the above formula (A5) are shown in Table 5-1 and Table 5-2. In the Tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

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Table 5-1

'Example compound R ⁵⁰¹ R ⁵⁰² R ⁵ ® R ⁵⁰⁴ R ⁵⁰⁵ R ⁵⁰⁶ R ⁵⁰⁷ R ⁵⁰⁸ R ™ R ⁵¹⁰ z ⁵⁰¹ THE α β Ύ A501 H THE H H H H H H CN CN ç - O- —Ch ₂ -oh A502 H THE H H H H H H CN CN ç - --- ch ₂ -oh A503 H THE H H H H H H CN CN ç - - A504 H THE H H H H H H CN CN ç - - A505 H THE H H H H H H CN CN ç - - A506 H no ₂ H H no ₂ H no ₂ H THE - N - h ₂ c-oh —c ^z h ₂ A507 H H H H H H H H THE - N - COOH - A508 H H H H H H H H THE - N - - A509 H H H H H H H H THE - N h ₂ c-oh —CH H ₂ b-CH ₃ - - A51O CH3 H H H H H H ch ₃ THE - N - h ₂ c-oh --- c ^z h ₂ A511 H H Cl H H Cl H H THE - N - -B h ₂ c-oh —c ^z h ₂ A512 H O H H H H H THE - N - -B h ₂ c-oh —c ^z h ₂ A513 H bc ₂ H ₅ H H H H bC ₂ H ₅ H THE - N - h ₂ c-oh —òh ₂ A514 H no ₂ H H no ₂ H no ₂ H THE - N - h ₂ c-oh —óh ₂ A515 H THE H H H H THE H CN CN Ç - O- --- ch ₂ -oh A516 H THE H H H H THE H CN CN Ç - -

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Table 5-2

* Field example. ^ To. R ⁵⁰¹ R ⁵⁰² R ⁵⁰³ R ⁵⁰⁴ R ⁵⁰⁵ R ⁵⁰⁶ R ⁵⁰⁷ R ⁵⁰⁸ R ⁵⁰⁹ R ⁵¹⁰ ^ 501 THE The 7 A517 H THE H H H H THE H CN CN ç - THE - A518 H THE H H H H THE H GN CN ç - The ^sH - A519 H THE H H H H THE H CN CN ç H ₂ C-OH -ca H ^ b — CHg - - A520 H THE H H H H THE H CN CN ç H ₂ C-OH —ch ₂ - - A521 H THE H H H H THE H CN CN ç - - COOH A522 H THE H H H H THE H CN CN ç - - NH2 A523 H H THE H H THE H H CN CN ç - —Ch ₂ -oh A524 H THE H H H H THE H - - O - --- ch ₂ -oh A525 H THE H H H H THE H - - 0 - - A526 H THE H H H H THE H - - 0 - - A527 H THE H H H H THE H - - 0 - ~ O ~ ^sH - A528 H THE H H H H THE H CN O ç - -0- —CH2-OH A529 H THE H H H H THE H bC ₂ H _s bc ₂ Hõ ç - --CH2-OH A530 H H H H H H H H THE THE ç - - COOH A531 H THE H H H H THE H CN CN ç - 0- —Ch ₂ -oh A532 H THE H H H H - - AT THE, - N - —Ch ₂ -oh

The specific examples of compounds represented by the above formula (A6) are shown in Table 6. In the Table, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the column of α or β.

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Table 6

i Compound example _r 6 ° ¹ R ⁶⁰² r603 R ⁶⁰⁴ r605 R ⁶⁰⁶ THE α β Ύ A601 THE H H H H H - O- --- ch ₂ -oh A602 THE H H H H H - --- ch ₂ -oh A603 THE H H H H H - - A604 THE H H H H H - nh ₂ - A605 THE H H H H H - ^ O ~ ^sh - A606 THE H H H H H h ₂ c-oh -h h £ -ch ₃ - - A607 THE H H H H H h ₂ c-oh —ch ₂ - - A608 THE H H H H H - - COOH A609 THE H H H H H - - nh ₂ A610 THE CN H H H H - - nh ₂ A611 CN CN THE H H H - - nh ₂ A612 THE H H H H H - - OH A613 H H THE H H H - - OH A614 ch ₃ H THE H H H - - OH A615 H H THE H H THE - - OH A616 THE THE H H H H - -O --ch ₂ -oh A617 THE THE H H H H h ₂ c-oh —ch ₂ - - A618 THE THE H H H H h ₂ c-oh -οή H ₂ b- ch ₃ - - A619 THE THE H H H H - - COOH

Specific examples of compounds represented by the above formula (A7) are shown in Table 7-1, Table 7-2 and Table 7-3. In the Tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

20Π7

Table 7-1

Compound example R ⁷⁰¹ R ⁷⁰² _R 703 _r ? O4 _R 705 _R 706 _R 707 _R 708 THE The β T A7O1 THE H H H H H H H - -O- --CH ₂ -OH A702 THE H H H H H H H - -d --- ch ₂ -oh A703 THE H H H H H H NO ₂ - —Ch ₂ -oh A704 THE H H H H H H H - - A705 THE H H H H H H H - nh ₂ - A706 THE H H H H H H H - - A707 THE H H H H H H H h ₂ c-oh -cá H ^ b — CK ₃ - - A708 THE H - H H H H H H - - COOH A709 THE H H H - / bc ₂ h ₅ H H H - - COOH A710 THE H H H THE H H H - -O- —Ch ₂ -oh A711 THE H H H THE H H H - --ch ₂ -oh A712 THE H H NO _Z THE H H NO 2 - --ch ₂ -oh A713 THE H F H THE H F H - --ch ₂ -oh A714 THE H H H THE H H H - boOH - A715 THE H H H THE H H H - -

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Table 7-2

Compound example R ⁷⁰¹ _r 702 _r 7O3 R ⁷⁰⁴ r ^{5 * 7} ° 5 R ⁷⁰⁸ R ⁷⁰⁷ R ⁷⁰⁸ THE The β Ύ A716 THE H H H THE H H H - O - A717 THE H H H THE H H H h ₂ c — oh -cá κ ₂ ί-ch ₃ - - A718 THE H H H THE H H H - - COOH A719 H THE H H H THE H H - - COOH A720 THE H H H THE F H H COOH A721 THE H H ch ₃ ch ₃ H H H - - COOH A722 THE H H c ₄ h ₉ c ₄ h ₉ H H H - - COOH A723 THE H H -O -CD H H H - - COOH A724 THE H H ch ₃ ch ₃ H H H - O- —Ch ₂ -oh A725 THE H H c ₄ h ₉ c ₄ h ₉ H H H - O- --ch ₂ -oh A726 THE H H O H H H - O- —Ch ₂ -oh A727 THE H H c ₄ h ₉ c ₄ h ₉ H H H - - A728 THE H H c ₄ h ₉ c ₄ h ₉ H H H - nh ₂ - A729 THE H H c ₄ h ₉ c ₄ h ₉ H H H - O -

Table 7-3

Compound example R ⁷⁰¹ R ⁷⁰² R ⁷⁰³ R ⁷⁰⁴ R ⁷⁰⁵ R ⁷⁰⁶ _r 707 R-- THE THE' α β Ύ The β Ύ A730 THE H H H THE' H H H h ₂ c-oh-ca Hjt-CHa - - - -B —Ch ₂ -oh A731 THE H H H THE' H H H - --ch ₂ -oh - (- ch ₂ ^ oh - - A733 THE H H H THE' H H H - --C-COOH h ₂ --- C-COOH h ₂ - -

Specific examples of compounds represented by the above formula (A8) are shown in Table 8-1, Table 8-2 and Table 8-3. In the Tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

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Table 8-1

Compound example R ⁸⁰¹ R ⁸⁰² _R 8 ° 3 _r8 ° 4 R ⁸⁰⁶ R ⁸⁰⁶ R ⁸⁰⁷ R ⁸⁰⁸ R ⁸⁰⁹ R ⁸¹⁰ THE The 0 T A801 H H H H H H H H h ₃ cd? THE h ₂ c-oh -h h £ -ch ₃ - - A802 H H H H H H H H CsHs p 0> η ₅ THE h ₂ c-oh —h H ₂ b- ch ₃ - - A803 H H H H H H H H CjHs THE - -B H ₂ C-OH —c ^ A804 H H H H H H H H C2H5 THE - -B —Ch ₂ -oh A805 H H H H H H H H CzHs P THE - -B —Ch ₂ -oh A8O6 H H H H H H H H h ₃ c ' THE h ₂ c-oh -c H ₂ t; -CH ₃ - - A8O7 H H H H H H H H THE h ₂ c-oh -h h £ -ch ₃ - - A808 H H H H H H H H ^{-h cn} THE h ₂ c-oh-ca H ₂ b-CH ₃ - - A809 H H H H H H H H h ₃ c C2H5 THE —Θδ ^ -ιο ^- - - A810 H H H H H H H H —C ₆ h ₁₃ THE h ₂ c-oh -h h £ -ch ₃ - - A811 H H H H H H H H θΛ —C-CH H2 C2H5 THE - b> h ₂ c ^_ oh —όκ ₂ A812 H H H H H H H H h ₃ c -0 C2H5 THE - - A813 H H H H H H H H CzHs í THE - nh ₂ - A814 H H H H H H H H ΟζΗ ₅ THE - "The ^H - A815 H H H H H H H H C2H5 THE - h ₂ c-ch ₃ -ca booH -

31/77

Table 8-2

compound example R ⁸⁰ ' _r 802 R ⁸⁰³ R ⁸⁰⁴ _r 805 _r 8 ° 6 R ⁸⁰⁷ R ⁸⁰⁸ R ⁸⁰⁹ R ⁸ ' ⁰ THE α β T A816 H H H H H H H H C2H5 R THE - —C-COOH H ₂ - A817 H H H H H H H H 0, ¾ í THE - - A818 H H H H H H H H ΗίΗ ₅ R THE - —C-COOH h ₂ A819 H CN H H H H CN H 0, ¾ THE h ₂ c-oh —CH ch ₃ - - A820 H "O H H H H H h ₃ c 02¾ THE h ₂ c-oh-ca H ₂ b-CH ₃ - - A821 H THE H H H H H H h ₃ c -0 C2H5 H ₃ C d ⁷ - - -COOH A822 H Cl Cl H H Cl Cl H h ₃ c C2H5 THE h ₂ c-oh -h h £ -ch ₃ - - A823 H H H H H H H H h ₃ c b 0, η ₅ THE h ₂ c-oh -cá H ^ b- ch ₃ - - A824 H H H H H H H H THE THE h ₂ c-oh -οή h £ -ch ₃ - - A825 H H H H H H H H THE THE - H ₂ C-OH —dH ₂ A826 H H H H H H H H THE THE - - A827 H H H H H H H H THE THE - -p nh ₂ - A828 H H H H H H H H THE THE - ~ O ^ ^sh - A829 H H H H H H H H THE THE - HpC — CH ₃ -c boOH - A830 H H H H H H H H THE THE - -R - A831 H H H H H O H 02¾ P C2H5 THE - H ₂ C-OH —C * H ₂

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Table 8-3

Compound example R ⁸⁰¹ R ⁸⁰² R ⁸⁰³ R ⁸⁰⁴ R ⁸⁰⁵ p806 _r 8 ° 7 p808 p809 R ⁸¹⁰ THE THE' The β T The β T A832 H H H H H H H H THE THE h ₂ c-oh -ch η ₂ ^ -οη ₃ - - - (- ch ₂ - ^ oh - - A833 H H H H H H H H THE THE' - --ch ₂ -oh - (- CHj - ^ - OH - - A834 H H H H H H H H THE THE' - —C-COOH h ₂ —C-COOH h ₂ - - A835 H H H H H H H H THE THE' - ^ The “° ^cH3 - —Ch ₂ -oh -

Specific examples of compounds represented by the above formula (A9) are shown in Table 9-1 and Table 9-2. In the Tables, the case where γ is indicates a hydrogen atom, and the hydrogen atom for ο γ is incorporated into the structure provided in the α or β column.

33/77

Table 9-1

Compound example R0O1 R0K rTO R0O4 r0O5 R ⁹⁰⁶ R ⁰⁰⁷ R0C® THE The β T A9O1 THE H H H H H H H —Ch ₂ -oh - - A9O2 THE H H H H H H H - (- ch ₂ - £ oh - - A903 THE H H H O H H H fCH ₂ -) - OH - - A9O4 THE H H H H H -f-CH ₂ -) jOH - - A9O5 THE no ₂ H H H no ₂ H H -f-CH ₂ -) rOH - - A9O6 THE H H H H THE H H - (- ch ₂ - £ oh - - A907 THE H H H THE H H H - (oh ₂ - ^ oh - - A908 THE H H H THE H H H - - A9O9 THE H H THE H H H H fCH ₂ - ^ OH - - A91O THE H H THE H H H H - - A911 H H H H H H H THE —Ch ₂ -oh - - A912 H H H H H H H THE - (- CH _2. ) JOH - - A913 H no ₂ H H H NO _Z H THE -f <H ₂ ^ O ^H - A914 H H H H H H H THE - - A915 H H H H H H H THE - H ₂ C-OH —c ^z h ₂ A916 H H H H H H H THE - - A917 H H H H H H H THE - nh ₂ - A918 H H H H H H H THE - ^ The ^C00H A919 H CN H H H H CN THE - ^ The “ ^ocH3 - A92O THE THE H H H H H H fCHj-JjOH - - A921 THE THE H no ₂ H H no ₂ H fCH ₂ ^ OH - - A922 H THE THE H H H H H - - OH A923 H H THE H H H H H - - A924 H H THE H H H H THE - H ₂ C-COOH • ch ₂

34/77

Table 9-2

Compound example R ⁹⁰¹ _r 9 ° 2 p903 _r 9 ° 4 p905 _r 90S _r 9 ° 7 p908 THE THE' α β Ύ The β T A925 THE H H H THE' H H H fCH ^ OH - - - - A926 THE H H THE' H H H H fCH ₂ - ^ OH - - - - A927 H THE' H H H H H THE fCH ₂ - ^ OH - - - ^ Ç ^ -GQOn -

A derivative (derived from an electron transport substance) having a (A1) structure can be synthesized by a well-known synthesis method described, for example, in US Patents No. 4,442,193, 4,992,349 and 5,468. 583 and Chemistry of Materials, Vol.19, No. 11, 2703-2705 (2007). The derivative can also be synthesized by a reaction of a naphthalenetetracarboxylic dianhydride and a monoamine derivative, which are commercially available from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan

Co., Ltd. and Johnson Matthey Japan Inc.

A compound represented by (A1) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A1) includes a method of directly incorporating the polymerizable functional groups into the derivative having a structure (A1), and a method of incorporating the structures having the polymerizable functional groups or groups functional elements capable of becoming precursors of polymerizable functional groups. Examples of the latter method include, based on a halide of a naphthylimide derivative, a method of incorporating an aryl group containing a functional group, for example, through the use of a cross-coupling reaction using a palladium catalyst and a base , a method of incorporating an alkyl group containing a functional group using a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group and a carboxyl group through the production of an epoxy or CO ₂ compound to act after litiation. There is a method of using a naphthalenotetracarboxylic dianhydride derivative or a monoamine derivative having polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups as a raw material for the synthesis of the naphthylimide derivative.

Derivatives having an (A2) structure are commercially available, for example, from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc. Derivatives can also be synthesized based on a derivative

35/77 of phenanthrene or a phenanthroline derivative using the synthetic methods described in Chem. Educator No.6, 227-234 (2001), Journal of Synthetic Organic Chemistry, Japan, vol.15, 29-32 (1957) and Journal of Synthetic Organic Chemistry, Japan, vol.15, 32-34 (1957). A dicyclomethylene group can also be incorporated by a reaction with malononitrile.

A compound represented by (A2) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a (A2) structure includes a method of directly incorporating the polymerizable functional groups, and a method of incorporating structures having the polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups in the derivative having a structure (A2). Examples of the latter method include, based on a phenatrenoquinone halide, a method of incorporating an aryl group containing a functional group using a cross-coupling reaction using a palladium catalyst and a base, a method of incorporating a alkyl group containing functional group through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group and a carboxyl group through the production of an epoxy or CO compound ₂ to act after litigation.

Derivatives having an (A3) structure are commercially available from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc. Derivatives can also be synthesized based on a phenanthrene derivative or a phenanthroline derivative using a synthetic method described in Bull. Chem. Soc., Jpn., Vol.65, 1006-1011 (1992). A dicyclomethylene group can also be incorporated by a reaction with malononitrile.

A compound represented by (A3) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having the structure of the above formula (A3) includes a method of directly incorporating the polymerizable functional groups into the derivative having the structure of formula (A3), and a method of incorporating structures having polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups in the derivative having the structure of formula (A3). Examples of the latter method include, based on a phenatroline quinone halide, a method of incorporating an aryl group containing a functional group using a cross-coupling reaction using a palladium catalyst and a base, a method of incorporating a alkyl group containing functional group through the use of

36/77 a cross-coupling reaction using a FeCI ₃ catalyst and a base and method of incorporating a hydroxyalkyl group and a carboxyl group by producing an epoxy or CO ₂ compound to act after lithiation.

Derivatives having an (A4) structure are commercially available, for example, from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc. Derivatives can also be synthesized based on a derived from acenaftenoquinone through the synthesis methods described in Tetrahedron Letters, 43 (16), 2991-2994 (2002) and Tetrahedron Letters, 44 (10), 2087-2091 (2003). A dicyclomethylene group can also be incorporated by a reaction with malononitrile.

A compound represented by the formula (A4) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A4) includes a method of directly incorporating the polymerizable functional groups into the derivative having a structure (A4), and a method of incorporating structures having the polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups in the derivative having a structure (A4). Examples of the latter method include, based on an acenaphenoquinone halide, a method of incorporating an aryl group containing a functional group, for example, using a cross-coupling reaction using a palladium catalyst and a base, a method incorporation of an alkyl group containing functional group through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group and a carboxyl group through the production of a compound epoxy or CO ₂ to act after litigation.

Derivatives having an (A5) structure are commercially available, for example, from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc. Derivatives can also be synthesized using a derivative of fluorenone and malononitrile by a method of synthesis described in US Patent No. 4,562,132. Derivatives can also be synthesized using a fluorenone derivative and an aniline derivative using the synthesis methods described in Japanese Open Patent Applications Nos. H5-279582 and H7-70038.

A compound represented by the formula (A5) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A5) includes a method of directly incorporating the polymerizable functional groups into the derivative having a structure (A5), and a method of incorporating the

37/77 structures having the polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups in the derivative having a structure (A5). Examples of the latter method include, based on a fluorenone halide, a method of incorporating an aryl group containing a functional group, for example, using a cross-coupling reaction using a palladium catalyst and a base, a method incorporation of an alkyl group containing functional group through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group and a carboxyl group through the production of a compound epoxy or CO ₂ to act after litigation.

Derivatives having an (A6) structure can be synthesized by synthesis methods described in, for example, Chemistry Letters, 37 (3), 360-361 (2008) and Japanese Open Patent Application No. H9-151157. The derivatives are commercially available from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc.

A compound represented by the formula (A6) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A6) includes a method of directly incorporating the polymerizable functional groups into a naphthoquinone derivative, and a method of incorporating structures having the polymerizable functional groups or capable functional groups to become precursors of polymerizable functional groups in a naphthoquinone derivative. Examples of the latter method include, based on a naphthoquinone halide, a method of incorporating an aryl group containing a functional group, for example, using a cross-coupling reaction using a palladium catalyst and a base, a method incorporation of an alkyl group containing functional group through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group and a carboxyl group through the production of a compound epoxy or CO ₂ to act after litigation.

Derivatives having a structure (A7) can be synthesized by synthesis methods described in Japanese Open Patent Application No. H1-206349 and Proceedings of PPCI / Japan Hard Copy '98, Proceedings, p.207 (1998). Derivatives can be synthesized, for example, using the commercially available phenol derivatives from Tokyo Chemical Industry Co., Ltd., or Sigma-Aldrich Japan Co., Ltd., as a raw material.

A compound represented by (A7) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a group

38/77 of methoxy), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structural (A7) includes a method of incorporating structures having polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups. Examples of the method include, based on a diphenquinone halide, a method of incorporating an aryl group containing a functional group, for example, using a cross-coupling reaction using a palladium catalyst and a base, a incorporation of an alkyl group containing functional group through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group, and a carboxyl group through the production of an epoxy compound or CO ₂ to act after litigation.

Derivatives having an (A8) structure can be synthesized by a well-known synthetic method described, for example, Journal of the American Chemical Society, Vol.129, No.49, 15259-78 (2007). Derivatives can also be synthesized by a reaction of perylenetetracarboxylic dianhydride and a commercially available monoamine derivative from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc.

A compound represented by the formula (A8) has polymerizable functional groups (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A8) includes a method of directly incorporating the polymerizable functional groups into the derivative having a structure (A8), and a method of incorporating the structures having the polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups in the derivative having a structure (A8). Examples of the latter method include, based on a halide of a peryleneimide derivative, a method of using a cross-coupling reaction using a palladium catalyst and a base and a method of using a cross-coupling reaction using a catalyst. FeCI ₃ and a base. There is a method of using a perylenetetracarboxylic dianhydride derivative or a monoamine derivative having polymerizable functional groups or functional groups capable of becoming precursors of polymerizable functional groups as a raw material for the synthesis of the peryleneimide derivative.

Derivatives having an (A9) structure are commercially available, for example, from Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd. and Johnson Matthey Japan Inc.

A compound represented by the formula (A9) has functional groups

39/77 polymerisable (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group), polymerizable with a crosslinking agent. A method for incorporating these polymerizable functional groups into a derivative having a structure (A9) includes a method of incorporating structures having polymerizable functional groups or functional groups capable of becoming precursors to polymerizable functional groups in a commercially anthraquinone derivative available. Examples of the method include, based on an anthraquinone halide, a method of incorporating an aryl group containing a functional group, for example, by using a cross-coupling reaction using a palladium catalyst and a base, a incorporation of an alkyl group containing functional group, through the use of a cross-coupling reaction using a FeCI ₃ catalyst and a base and a method of incorporating a hydroxyalkyl group, and a carboxyl group through the production of a compound epoxy or CO2 to act after litiation.

Crosslinking agent

Then, a crosslinking agent will be described. As a cross-linking agent, a compound can be used which polymerizes or cross-links with an electron-carrying substance having polymerizable functional groups and a thermoplastic resin having polymerizable functional groups. Specifically, the compounds described in “Crosslinking Agent Handbook”, edited by Shinzo Yamashita, Tosuke Kaneko, published by Taiseisha Ltd. (1981) (in Japanese), and others can be used.

The crosslinking agents used for an electron transport layer can be isocyanate compounds and amine compounds. The crosslinking agents are more preferably crosslinking agents (isocyanate compounds, amine compounds) having 3 to 6 groups of an isocyanate group, a blocked isocyanate group or a monovalent group represented by -CH ₂ -OR ¹ from point of view of providing a uniform layer of a polymer.

As the isocyanate compound, an isocyanate compound having a molecular weight in the range of 200 to 1300 can be used. An isocyanate compound having 3 to 6 isocyanate groups or blocked isocyanate groups can still be used. Examples of the isocyanate compound include isocyanurate modifications, biuret modifications, allophanate modifications and adduct modifications of trimethylolpropane or pentaerythritol of triisocyanatobenzene, triisocyanatomethylbenzene, triphenylmethane triisocyanate, lysine triisocyanate, and such as diisylene diisene, as well as diisisate hexamethylene, dicyclohexylmethane diisocyanate, naphthalene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, xylylene diisocyanate, 2,2,4-trimethylexamethylene diisocyanate, methyl-2,6-diisocyanate hexaneate. Above all, modified isocyanurate and modified adducts are more

40/77 preferable.

A blocked isocyanate group is a group having a -NHCOX ¹ structure (X ¹ is a blocking group). X ¹ can be any blocking group as long as X ¹ can be incorporated into an isocyanate group, but it is more preferably a group represented by one of the following formulas from (H1) to (H7).

In the following, specific examples of isocyanate compounds will be described.

OCN

NCO

The NCO _u „/) - CN-CeHi ₂ ^Η ζγ H NCO

C2H5 — C — O “C — N — CgHi2 h ₂ 6 o ^h

OCNC ₈ Hi2 o ^H Yico

NCO cn-c ' ₆ h ₁₂

C ₆ Hi ₂ -NH (R8)

OCn 'CNC ₆ Hi ₂

The ^H \ co (B5) oo

OCN £ r NCO

C ₆ H> ₂ -N 'ίμ-ο ₆ η ₁₂ -ν ^χ ' nc ₆ h- ₂ 0 *% '% O *%'%

(B7)

NCO

41/77 oh ₂ c-ch ₂ h ₂ c — ch ₂ b- N-CH CH-C-CH CH-NCO

^H H2C-dH2 ^H 2H2C-CH ₂ I

CH ₂ h ₂ c — ch ₂ h ₂ c-ch ₂

C ₂ H ₅ —COCN-CH CH-C-CH CH-NCO

CH, OH ₂ c-CH ₂ ^h 2H ₂ C-CH ₂

I oh ₂ c-ch ₂ h ₂ c-ch ₂

C — N-CH CH-C-CH CH-NCO θ ^{Ζ H} H2C-CH2 ^H 2H2C-CH ₂ (B10)

h ₂ ° ^C % H ' ^C h ₂ h ₂ ° CN. > C.

CH> ch ₂ ^Η ^> Αη ₂ ^H 2 CH

H ₂ C 'xh ₂

H ^ rA

Η'- '' -, 1 I l_i | | ^m 2 ^m 2

ΌΗΉ, Ο CH CH bDH; H ₂ C CH h ₂ > C '-C' Τ '' η ₂ η ₂ η ₂ ocn-c ₆ h, ₂ o

HN-c 'O \ -C ^Z ____ ocn — c / h ₁₂ ό-ΟβΗ, ^ εί c ₆ \ i ₁₂ -nco

Ο C ₆ H, ₂ -NCO

Ο% -ΝΗ, _π ,,.

W (Β13) (Bll)

OCN

H ₂ ? H ₂ h ₂ > 3 CH>2> C

H ₂ ' _C oh ₂ h ₂

NCO

NCO NCO

NCO

ο NCO

OCN-c ' ₆ H ₁₂ Η

-c ₂ h ₅ (Β20)> dcnc ₆ h ₁₂ ^Η \ co

NCO

The amine compound can be at least that selected from the group consisting of compounds represented by the following formula (C1), oligomers of compounds represented by the following formula (C1), compounds represented by the following formula (C2), oligomers of compounds represented by the following formula (C2), compounds represented by the following formula (C3), oligomers of compounds represented by

42/77 following formula (C3), compounds represented by the following formula (C4), oligomers of compounds represented by the following of formula (C4), compounds represented by the following general formula (C5), and oligomers of compounds represented by the following general formula ( C5).

each independently represents a hydrogen atom, a hydroxy group, an acyl group or a monovalent group represented by -CH ₂ -OR ¹ ; at least one from R ¹¹ to R ¹⁶ , at least one from R ²² to R ²⁵ , at least one from R ³¹ to R ³⁴ , at least one from R ⁴¹ to R ⁴⁴ , and at least one from R ⁵¹ to R ⁵⁴ are a monovalent group represented by -CH ₂ -OR ¹ , R ¹ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; the alkyl group can be a methyl group, an ethyl group, a propyl group (n-propyl group, iso-propyl group) or a butyl group (n-butyl group, iso-butyl group , tert-butyl group) from the point of view of the ability to be polymerizable; R ²¹ represents an aryl group, an aryl group substituted by an alkyl group, a cycloalkyl group or a cycloalkyl group substituted by the alkyl group.

In the following, specific examples of compounds represented by one of the formulas (C1) to (C5) will be described. The oligomers (multimers) of the compounds represented by one of the formulas (C1) to (C5) can be contained. The compounds (monomers) represented by one of the formulas (C1) to (C5) can be contained in 10% by weight or more of the total mass of the amine compounds from the point of view of providing a uniform layer of a polymer. The degree of polymerization of the aforementioned multimer can be 2 or more and 100 or less. The aforementioned multimer and monomer can be used as a mixture of two or more.

Examples of compounds represented by the above formula (C1) generally available commercially include Supermelami No. 90 (manufactured by NOF Corp.), Superbekamine (R), TD-139-60, L-105-60, L127-60, L110-60 , J-820-60 and L-821-60 (manufactured by DIC Corporation), Yuban 2020 (manufactured by Mitsui Chemicals Inc.), Sumitex Resin M-3 (manufactured by Sumitomo Chemical Co., Ltd.), and Nikalac MW -30, MW

43/77

390 and MX-750LM (Nihon Carbide Industries Co., Inc). Examples of compounds represented by the above formula (C2) generally available commercially include Superbekamine (R) L-148-55, 13-535, L-145-60 and TD-126 (manufactured by Dainippon Ink and Chemicals, Inc.), and Nikalac BL-60 and BX-4000 (Nihon Carbide Industries Co., Inc). Examples of compounds represented by the above formula (C3) generally available commercially include Nikalac MX-280 (Nihon Carbide Industries Co., Inc). Examples of compounds represented by the above formula (C4) generally available commercially include Nikalac MX-270 (Nihon Carbide Industries Co., Inc). Examples of compounds represented by the above formula (C5) generally available commercially include Nikalac MX-290 (Nihon Carbide Industries Co., Inc).

In the following, specific examples of compounds of the formula (C1) will be described.

HOH ₂ C, _n xCH ₂ OH

H ₃ COH ₂ C _XnX CH ₂ OCH3

h ₃ coh ₂ c _x ^ ch ₂ oh

N

h ₃ coh ₂ c ^ _n · n-Bu — OH2CÍ (C1-5)

(C1-6) ch ₂ och ₃ ch ₂ och ₃

CH2O — n-Bu

6H ₂ OCH ₃

ΑΑΙΊ1 iso-Bu — OH ₂ C _x ^ _x CH ₂ O — iso-Bu

N ιγ'λ ~ 7 \

I ji (C1-7) iso-Bu — 0Η ₂ 0 ~~ ν1Μ ^^ ν ^ Ο · Ι ₂ 0 — iso-Bu iso-Bu — OH ₂ d Óh ₂ O — iso-Bu iso- Bu-OH ₂ C ^ _n > |

N N ÍC ^ A Q \

Γ 1 (C1-9)

H ^ / ^^ _N ^ CH ₂ O-iso-Bu iso- Bu-oh ₂ 8 ê H ₂ O — iso-Bu iso-Bu-Oh ^ C ^ N ^ CHjO — n-Bu

NN ΙΓΆ R \ k à ^(C1_8) iso-Bu — Oh ^ C- ^ bisl ^^ NCH ₂ O — iso-Bu n-Bu — OH ₂ dk ₂ O —iso-Bu iso-Bu-OH ₂ C _Xn ^ CH ₂ OCH ₃ / ΓΊ ini

I JI (C1-10)

H ₃ COH ₂ C ^ _N ^z bj ' ^xX _N -CH ₂ O-iso-Bu iso-Bu — OH ₂ cy CH ₂ O — iso-Bu iso-Bu — OH ₂ C ^ _X CH ₂ OH

N N ή ή λ x k 1 (01-11)

H0H ₂ C ^ _N - ^z % | '^ _N ^ CH ₂ 0-iso-Bu iso-Bu — OH ₂ c (Óh ₂ O — iso-Bu n-Bu-OH ₂ C ^ _N> CH ₂ OH fS ¹ (C1-12)

H ₃ COH ₂ C ^ _N ^zX Sj ^ \ _N ^ CH ₂ On-Bu n-Bu-OH ₂ d éH ₂ OCH ₃

In the following, specific examples of compounds of formula (C2) will be described.

45/77 (C2-1) (C2-2) hoh ₂ c ^ _{n n} -ch ₂ oh h ₃ coh ₂ c ^ _n (!: H ₂ och3

(C2-5) 'N — CH ₂ O — n-Bu H ₃ COH ₂ C

H ₃ COH ₂ (^

I — CH2OCH3 n-Bu—

H3COH2C n-Bu — OH ₂ C- ^ | 'Tk n-Bu-OH ₂ w / (Íh ₂ O — n-Bu

N ^ N (C2-8) H ₃ COH ₂ C ~ - _n ^z % ^x \ -CH ₂ OCH ₃ h ₃ coh ₂ J Íh ₂ OCH ₃ çh ₃ (C2-11)

H ₃ COH ₂ C ^ _n ^/ Sm '^ ^x _n -ch ₂ och ₃ H ₃ COH ₂ C <Íh ₂ OCH3

(C2-3) _n —CH ₂ OCH ₃ : H ₂ OCH3 hoh ₂ c ^ _N 'hoh ₂ J ^ H ₂ 0 — n-Bu

N ^ N (C2-7) JL Λ ^{ 1 ^/ ^ N '% - CH2OH él-1 ₂ OH h ₃ coh ₂ c ^ _n h ₃ coh ₂ J

(C2-14)

N -— CH ₂ OCH3 <Í: h ₂ och3 h ₃ coh ₂ c ^ _n h ₃ coh ₂ J

(C2-17) n-Bu — OH ₂ Cn-Bu-OH ₂ C

H ₃ C n-Bu — 0Η ₂ 0n-Bu-OH ₂ C n-Bu— n-Bu — OH ₂ <^

(C2-9) (C2-12)

-CH ₂ O — n-Bu —n-Bu _n -CH ₂ O — n-Bu —n-Bu (C2-15) m — CH ₂ O — n-Bu ² n-Bu-OH ₂ C ^ _N / n-Bu-OH ₂ C

HOH ₂ C- _n hoh ₂ ^ hoh ₂ c ^ _n / hoh ₂ c

h ₂ oh (C2-16) (C2-13)

-ch ₂ oh (C2-10) _n -CH ₂ OH _n -ch ₂ och ₃ ^ η ₂ οοη ₃ n-Bu — OH ₂ C— _R / H ₃ COH ₂ C

N - CH ₂ O — n-Bu

C ^ H ₂ O — n-Bu

In the following, specific examples of compounds of formula (C3) will be described.

n-Bu — OH ₂ C J2 CH ₂ OCH ₃

I W (C3-3)

H3COC OH2O — n-Bu

O

H ₃ COH ₂ C _x à CH ₂ OH \ _J (C3-6) hoh ₂ c ch ₂ och ₃ oo ^HOH 2 ^c \ NJk ^ ^ch 2 ° ^hh ₃ coh ₂ c U ch ₂ och ₃ ¹ \ _k (C3- 1) \ / (C3-2)

HOH ₂ C CH ₂ OH H3COH2C CH2OCH3 oo n-Bu — OH ₂ C J2 _N , _C H ₂ On-Bu H ₃ COH ₂ C _{y χΗ}

W (C3-4) t / ^N (C3-5) n-Bu — OH ₂ C CH ₂ O — n-Bu H ₃ COH ₂ C CH ₂ OCH ₃

In the following, specific examples of compounds of formula (C4) will be described.

46/77

O

-Bu-OH ₂ C _Xn A _n A _H2OCH 3

M ^<C4 - ³⁾ '^ - ^ _n z- \ _n , CH ₂ OCH ₃ nI H (C4-2)

Η, ϋΟΗ, ϋ'χ ' _C H ₂ OCH, HjCOHjC- ^ Y ^ HjO-n-Bu

.. h ₃ coh _An A _{n> C} h ₂ oh (C4-5) M (C4-6)

Á A _____, Ki A ^H0H2 % Â _{N x} CH ₂ OH h ₃ coh ₂ c ^ JI _x ^^ _CH2OCH3

Η (° ⁴ - ¹ ) A JM J hoh ₂ c γ 'ch ₂ oh ¹

O 0 n-Bu — OH ₂ C « _C H ₂ On-Bu H ₃ COH ₂ CU _h

N N N N

Hm ^(C4_4) n-Bu-OH2C ' ^xN ' J ^/ ΊθΗ20 — n-Bu H ₃ COH ₂ C ^xN '^ ^z ' \ h ₂ OCH ₃ ΗΟΗ ₂ Ο ^ ”Ύ CH ₂ OCH ₃

In the following, specific examples of compounds of formula (C5) will be described.

Η ° Η ₂ % Α AH ₂ OH H ₃ COH ₂ CX _X h ₂ OCH ₃ n-Bu ^ H ₂ CX _C H ₂ OCH ₃ · ^N ----- IS1 N (C5-3)

H ₃ COC CH ₂ O — n-Bu

^HOH 2 ^C x _n A _m .CH ₂ OCH ₃ (C5-5) _H3COH2 q ^HOH 2 ^C ^ nn ^ CH2OH H3COH2C 0 xCH2OCH3 hoh2c ch2oh ( ^C5_1 ) H3COH ₂ is ch ₂ och ₃ ( ^C5 ' ² )

O ₀ n-Bu — OH ₂ C «r _H2 On-Bu H ₃ COH ₂ CX _H y Ϊ (C5-4) ^{3 2} > -V n-Bu OH ₂ C CH ₂ O — n-Bu H ₃ COH ₂ is CH ₂ OCH ₃

CH ₂ OH (C5-6)

Resin

Thermoplastic resin having polymerizable functional groups will be described. The thermoplastic resin having polymerizable functional groups can be a thermoplastic resin that has a structural unit represented by the following formula (D).

Y-W

In formula (D), R ⁶¹ represents a hydrogen atom or an alkyl group; Y ¹ represents an isolated bond, an alkylene group or a phenylene group; and W ¹ represents a hydroxy group, a thiol group, an amino group, a carboxyl group or a methoxy group.

A resin (hereinafter also referred to as a D resin) having a structural unit represented by the general formula (D) can be obtained through polymerization, for example, a commercially available monomer from Sigma-Aldrich Japan Co., Ltd. and Tokyo Chemical Industry Co., Ltd. and having a polymerizable functional group (a hydroxy group, a thiol group, an amino group, a carboxyl group and a methoxy group).

Resins are generally commercially available. Examples of commercially available resins include polyether polyol based resins such as AQD-457 and AQD-473 produced by Nippon Polyurethane Industry Co., Ltd., and Sunnix GP-400, GP700 and others more produced by Sanyo Chemical Industries, Ltd ., polyester polyol based resins such as Phthalkid W2343 produced by Hitachi Chemical Co., Ltd.,

47/77

Watersol S-118 and CD-520 and Beckolite M-6402-50 is M-6201-40IM produced by DIC Corporation, Haridip WH-1188 produced by Harima Chemicals Group, Inc. and ES3604, ES6538 and others produced by Japan UPICA Co ., Ltd., polyacrylic polyol based resins such as Burnock WE-300 and WE-304 produced by DIC Corporation, polyvinyl alcohol based resins such as Kuraray Poval PVA-203 produced by Kuraray Co., Ltd., polyvinyl acetal based such as BX-1, BM-1, KS-1 and KS-5 produced by Sekisui Chemical Co., Ltd., polyamide based resins such as Toresin FS-350 manufactured by Nagase ChemteX Corp, resins containing carboxyl groups such as Aqualic produced by Nippon Shokubai Co., Ltd. and Finelex SG2000 produced by Namariichi Co., Ltd., polyamine resins such as Rackamide produced by DIC Corporation, and polythiol resins such as QE-340M produced by Toray Industries, Inc. First of all, polyvinyl acetal resins, re polyol based polyols and more are more preferable from the point of view of the ability to be polymerized and the uniformity of an electron transport layer.

The weighted average molecular weight (Mw) of a D resin can be in the range of 5000 to 400000, and more preferably in the range of 5000 to 300000. Examples of a method for quantifying a polymerizable functional group in the resin include the titration of a group of carboxyl using potassium hydroxide, the titration of an amino group using sodium nitrite, the titration of a hydroxy group using acetic anhydride and potassium hydroxide, the titration of a thiol group using 5,5'-dithiobis (acid 2 -nitrobenzoic), and a calibration curve method using IR spectra of the samples in which the incorporation ratio of a polymerizable functional group is varied.

In Table 10 below, specific examples of resin D will be described.

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Table 10

structure molar number per 1 g of functional another place molecular weight R61 ¥ W D1 H isolated link OH 3.3 mmol bu strip 1 x 10 ⁵ D2 H isolated link OH 3.3 mmol butyral 4 * i0 ⁴ D3 H isolated link OH 3.3 mmol butyral 2 x 10 ⁴ 04 H isolated link OH 1.0 mmol polyolefin 1 x 10 ⁵ D5 H isolated link OH 3.0 mmol ester 8x10 ⁴ D6 H isolated link OH 2.5 mmol polyether 5 x 10 ⁴ D7 H isolated link OH 2.8 mmol cellulose 3 x10 ⁴ D8 H isolated link COOH 3.5 mmol polyolefin 6 x 10 ⁴ D9 H isolated link NH2 1.2 mmol polyamide 2 x 10 ⁵ D10 H isolated link SH 1.3 mmol polyolefin 9 x 10 ³ D11 H fehileno OH 2.8 mmol polyolefin 4X10 ³ D12 H isolated link OH 3.0 mmol butyral 7 x 10 ⁴ D13 H isolated link OH 2.9 mmol polyester 2 x 10 ⁴ D14 H isolated link OH 2.5 mmol polyester 6x10 ³ D15 H isolated link OH 2.7 mmol polyester 8 x 10 ⁴ D16 H isolated link COOH 1.4 mmol polyester 2X10 ⁵ D17 H isolated link COOH 2.2 mmol polyester 9 x 10 ³ D18 H isolated link COOH 2.8 mmol polyester 8x 10 ² D19 CH3 alkylene OH 1.5 mmol polyester 2x10 ⁴ D20 C2H5 alkylene OH 2.1 mmol polyester 1 x 10 ⁴ 021 G2H5 alkylene OH 3.0 mmol polyester 5x10 ⁴ 022 H isolated link OCH3 2.8 mmol polyester 7 X 10 ³ 023 H isolated link OH 3.3 mmol butyral 2.7 x 10 ⁵ D24 H isolated link OH 3.3 mmol butyral 4x10 ⁵ 025 H isolated link OH 2.5 mmol acetal 4 ^χ 10 ^δ

An electron transport substance having polymerizable functional groups can be 30% by weight or more and 70% by weight or less relative to the total mass of a composition including the electron transport substance having polymerizable functional groups, a crosslinking agent and a resin that has polymerizable functional groups.

Conductive support

As a conductive support (also referred to as a support), for example,

49/77 brackets made from a metal or aluminum alloy, nickel, copper, gold, iron or the like can be used. The support includes supports in which a thin film of aluminum metal, silver, gold or the like is formed on an insulating support of a polyester resin, a polycarbonate resin, a polyimide resin, a glass or the like, and supports in which a thin film of conductive material of indium oxide, tin oxide or the like is formed.

The surface of a support can be subjected to a treatment such as an electrochemical treatment such as anodic oxidation, a wet grinding treatment, an explosion treatment and a cutting treatment, in order to improve the electrical properties and suppress the edges of interference.

A conductive layer can be provided between a support and a base layer described later. The conductive layer is obtained by forming a coating film of a coating liquid by a conductive layer in which a conductive particle is dispersed in a resin, on the support, and drying of the coating film. Examples of the conductive particle include carbon black, acetylene black, metal powder such as aluminum, nickel, iron, nichrome, copper, zinc and silver, and metal oxide powder such as conductive tin oxide and ITO.

Examples of the resin include polyester resins, polycarbonate resins, polyvinyl butyral resins, acrylic resins, silicone resins, epoxy resins, melamine resins, urethane resins, phenolic resins and alkyd resins.

Examples of a solvent from a coating liquid to a conductive layer include ethereal solvents, alcoholic solvents, ketone solvents and aromatic hydrocarbon solvents. The thickness of a conductive layer can be 0.2 pm or more and 40 pm or less, more preferably 1 pm or more 35 pm or less, and even more preferably 5 pm or more and 30 pm or less.

Load generation layer

A charge generation layer is provided over a base layer (electron transport layer).

A charge-generating substance includes azo pigments, perylene pigments, anthraquinone derivatives, antoantrone derivatives, dibenzopyrenquinquinone derivatives, pyrantrone derivatives, isoviolantrone derivatives, indigo derivatives, thioindigo derivatives, phthalocyanine pigments such as phthalocyanines metallic and non-metallic phthalocyanines, and bisbenzimidazole derivatives. Above all, at least one of the azo pigments and phthalocyanine pigments can be used. Among the phthalocyanine pigments, oxytitanium phthalocyanine, chloro-phthalocyanine and hydroxy-phthalocyanine can be used.

Examples of a binder resin used for a charge generation layer

50/77 include polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylic ester, methacrylic ester, vinylidene fluoride and trifluoroethylene, polyvinyl alcohol resins, polyvinyl acetal resins, polycarbonate resins, resins polyester, polysulfone resins, polyphenylene oxide resins, polyurethane resins, cellulosic resins, phenol resins, melamine resins, silicon resins and epoxy resins. Above all, polyester resins, polycarbonate resins and polyvinyl acetal resins can be used, and polyvinyl acetal is more preferable.

In a charge-generating layer, the ratio (charge-generating substance / bonding resin) of a charge-generating substance and a bonding resin can be in the range of 10/1 to 1/10, and is most preferably in the range of 5 / 1 to 1 / 5. A solvent used by a coating liquid for a charge generation layer includes alcoholic solvents, sulfoxide-based solvents, ketone solvents, ether solvents, spherical solvents and aromatic hydrocarbon solvents. The thickness of a charge generation layer can be 0.05 pm or more and 5 pm or less.

Gap transport layer

A gap transport layer is provided over a load generation layer. Examples of a gap-carrying substance include polycyclic aromatic compounds, heterocyclic compounds, hydrazone compounds, styryl compounds, benzidine compounds and triaryl amine, triphenylamine compounds, and polymers having a group derived from these compounds in the main chain or side chain. Above all, triarylamine compounds, benzidine compounds and styryl compounds can be used.

Examples of a binder resin used for a gap transport layer include polyester resins, polycarbonate resins, polymethacryl ester resins, polyarylate resins, polysulfone resins and polystyrene resins. Above all, polycarbonate resins and polyarylate resins can be used. With regard to its molecular weight, the weighted average molecular weight (Mw), can be in the range of 10000 to 300000.

In a gap transport layer, the ratio (gap transport substance / binder resin) of a gap transport substance and a binder resin can be 10/5 to 5/10, and is most preferably 10/8 to 6 / 10. The thickness of a gap transport layer can be 3 pm or more and 40 pm or less. The thickness is more preferably 5 pm or more and 16 pm or less from the point of view of the thickness of the electron transport layer. A solvent used by a coating liquid for a gap transport layer includes alcoholic solvents, sulfoxide-based solvents, ketone solvents, ether solvents, steric solvents and aromatic hydrocarbon solvents.

51/77

Another layer such as a second base layer that does not contain a polymer according to the present invention can be provided between a support and the electron transport layer and between the electron transport layer and a charge generation layer.

A protective surface layer can be provided over a gap transport layer. The protective surface layer contains a conductive particle or a charge-carrying substance and a binder resin. The surface protective layer may also contain additives such as a lubricant. The binder resin itself of the protective layer can have conductivity and load transportability; in this case, the protective layer does not need to contain a conductive particle and a charge-carrying substance other than the binder resin. The binder resin of the protective layer can be a thermoplastic resin, and it can be a curable resin capable of being polymerized by heat, light, radiation (electron beams) or the like.

A method for the formation of each layer such as an electron transport layer, a charge-generating layer and a gap transport layer that constitute an electrophotographic photosensitive component, can be a method in which a coating liquid obtained by dissolving and / or dispersion of a material that constitutes each layer in a solvent is applied, and the coating film obtained is dried and / or cured. Examples of a method of applying the coating liquid include a dip coating method, a spray coating method, a curtain coating method and a spinning coating method. Above all, an immersion coating method can be used from the point of view of efficiency and productivity.

Process cartridge and electrophotographic mechanism

FIG. 3 illustrates a constitution of the outline of an electrophotographic mechanism having a process cartridge that has an electrophotographic photosensitive member.

In FIG. 3, reference number 1 indicates a cylindrical electrophotographic photosensitive component that is rotationally moved at a predetermined peripheral speed in the direction of the arrow about an axis 2 as a center. A surface (peripheral surface) of the rotatingly moved electrophotographic photosensitive component 1 is uniformly charged to a positive or negative potential predetermined by a charge unit 3 (primary charge unit: charge roller or the like). The surface is then subjected to irradiation light (image exposure light) 4 from a light irradiation unit (exposure unit, not shown) such as crack light or sweeping light radiation by laser beams. The electrostatic latent images corresponding to the objective images are successively formed on the surface of the electrophotographic photosensitive component 1 in such a way.

52/77

The electrostatic latent images formed on the surface of the electrophotographic photosensitive component 1 are developed with a toner contained in a developer of a development unit 5 to form the toner images. Then, the toner images formed and transported on the surface of the electrophotographic photosensitive component 1 are successively transferred to a transfer material (paper or the like) P by a transfer polarization of a transfer unit (transfer roller or the like) 6. The transfer material P is released from a transfer material feeding unit (not shown) and fed between the electrophotographic photosensitive component 1 and the transfer unit 6 (in a contact part) in sync with the rotation of the component photosensitive electrophotographic 1.

The transfer material P having the transferred toner images is separated from the surface of the electrophotographic photosensitive component 1, inserted in a fixation unit 8 to be subjected to the fixation of the image, and printed as a matter formed by image (print, copy) outside of the mechanism.

The surface of the electrophotographic photosensitive component 1 after the transfer of the toner image is subjected to the removal of the non-transferred developer (toner) by a cleaning unit (cleaning blade or the like) 7 to thereby be cleaned. Then, the surface is subjected to a charge neutralization treatment with the irradiation light (not shown) from a light irradiation unit (not shown), and therefore used repeatedly for image formation. As illustrated in FIG. 3, in the case where the load unit 3 is a contact load unit that uses a load roller or the like, irradiation of light is not necessarily required.

A plurality of some of the constituent elements among the constituent elements including the electrophotographic photosensitive component 1, the charge unit 3, the developing unit 5, the transfer unit 6 and the cleaning unit 7 described above, can be selected and adjusted in a container and integrally constituted as a process cartridge; and the process cartridge can be detachably constituted of an electrophotographic body of a copying machine, a laser printer or the like. In FIG. 3, the electrophotographic photosensitive component 1, the charge unit 3, the development unit 5 and the cleaning unit 7 are integrally supported and produced as a cartridge to thereby manufacture a process cartridge 9 that can be detachable and detachable from an electrophotographic mechanism body using an orientation unit 10 such as a body shield of the electrophotographic mechanism.

Examples

Next, the manufacture and evaluation of the photosensitive components

53/77 electrophotographic will be described. The "parts" in the Examples indicate "parts in bulk".

(Example 1)

An aluminum cylinder (JIS-A3003, an aluminum alloy) 260.5 mm long and 30 mm in diameter was produced to be a support (conductive support).

Then 50 parts of a titanium oxide particle coated with an oxygen-deficient tin oxide (powder resistivity: 120 ocm, tin oxide covering factor: 40%), 40 parts of a phenol resin (Plyophen J -325, produced by DIC Corporation, resin solids content: 60%), and 50 parts of methoxypropanol as a solvent (dispersion solvent) were placed in a sand mill using a 0.8 mm diameter glass globule , and subjected to a dispersion treatment for 3 hours to thereby prepare a dispersion liquid. After dispersion, 0.01 part of a SH28PA silicone oil (produced by Dow Corning Toray Co., Ltd.) and a silicone microparticle (Tospearl 120CA) as an organic resin particle were added to the dispersion liquid, and stirred to prepare a coating liquid for a conductive layer. The content of the silicon microparticle was a sum of its solids content and 5% by mass of the total mass of the titanium oxide particle and the phenol resin. The coating liquid for a conductive layer was dipped onto the support, and the obtained coating film was dried and heat polymerized for 30 min at 150 ° C to thereby form a conductive layer having a thickness of 16 pm.

The average particle diameter of the titanium oxide particle coated with an oxygen deficient tin oxide in the coating liquid for the conductive layer was measured by a centrifugal precipitation method using tetrahydrofuran as a dispersion medium, at a rotation frequency of 5000 rpm through the use of a particle size distribution analyzer (trade name: CAPA700) produced by HORIBA Ltd. As a result, the average particle diameter was 0.31 pm.

Then 4 parts of the electron transport substance (A101), 7.3 parts of the crosslinking agent (B1: blocking group (H1) = 5.1: 2.2 (mass ratio)), 0.9 parts of the resin (D1) and 0.05 part of dioctyltin laurate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone, to thereby prepare a coating liquid for a transport layer of electrons. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized, to thereby form an electron transport layer ( base layer) having a thickness of 0.53 µm.

The content of the electron transport substance in relation to the total mass of the

54/77 electron transport substance, crosslinking agent and resin was 33% by weight.

Then, 10 parts of a hydroxylgalium phthalocyanine crystal (charge-generating substance) having a crystal shape that has strong peaks at Bragg angles (2θ ± 0.2 °) of 7.5 °, 9.9 °, 12 , 5 °, 16.3 °, 18.6 °, 25.1 ° and 28.3 ° in CuKa characteristic X-ray diffractometry, 0.1 part of a compound represented by the following formula (17), 5 parts of a polyvinyl butyral resin (trade name: Eslec BX-1, produced by Sekisui Chemical Co., Ltd.) and 250 parts of cyclohexanone were placed in a sand mill using 0.8 mm diameter glass globules, and submitted to a dispersion treatment for 1.5 hours. Then 250 parts of ethyl acetate were added to prepare a coating liquid for a charge-generating layer.

The coating liquid for a charge generation layer was coated by immersion on the electron transport layer, and the coating film obtained was dried for 10 min at 100 ° C to form a charge generating layer having a thickness 0.15 pm. A laminated body having the conductive support, the conductive layer, the electron transport layer, and the charge-generating layer was formed in such a way.

Then, 4 parts of a triaryl amine compound represented by the following formula (9-1) and a benzidine compound represented by the following formula (9-2) and 10 parts of a polyarylate resin having a structural repeating unit represented by the following formula (10-1) and a structural repeating unit represented by the following formula (10-2) in a ratio of 5/5 and having a weighted average molecular weight (Mw) of 100,000 were dissolved in a mixed solvent of 40 parts of dimethoxymethane and 60 parts of chlorobenzene to prepare a coating liquid for a gap transport layer. The coating liquid for a gap transport layer was dipped onto the load-generating layer, and the obtained coating film was dried for 40 min at 120 ° C to thereby form a gap transport layer having a thickness of 15 pm.

55/77

In such a way, an electrophotographic photosensitive component having the laminated body and the gap transport layer to evaluate the double positive image was manufactured. In addition, as above, another electrophotographic photosensitive component was manufactured, and produced as an electrophotographic photosensitive component for determination.

(Determination test)

The photosensitive electrophotographic component for the determination described above was immersed for 5 min under the application of an ultrasonic wave in a mixed solvent of 40 parts of dimethoxymethane and 60 parts of chlorobenzene to extract the transport layer from gaps, and after that, the resultant was dried for 10 min at 100 ° C in order to manufacture a laminated body having the support, electron transport layer and charge generating layer, and the laminated body was produced as an electrophotographic photosensitive component for the determination. Its surface has been confirmed to have no component of the gap transport layer through the use of an FTIR-ATR method.

Then, a measuring part was cut in 2 cm (peripheral direction of the electrophotographic photosensitive component) x 4 cm (direction of its long axis) of the electrophotographic photosensitive component for determination, and a circular gold electrode having a thickness of 300 nm and a diameter of 10 nm was manufactured on the charge generation layer by the cathodic sublimation mentioned above.

Then, the photosensitive electrophotographic component for determination was left to stand for 24 hours in an environment with a temperature of 25 ° C and a humidity of 50% RH, and after that, a sample was manufactured which was constituted of the support, of the conductive layer , the electron transport layer, the charge generation layer and the gold electrode with the aforementioned determination method. First, the entire sample was covered with a blackout film; and impedance (R_dark) when an alternating electric field of 100 mV and 0.1 Hz was applied between the conductive support and the

56/77 gold electrode was measured by scanning the frequency from 1 MHz to 0.1 Hz and under the condition without light radiation from the surface of the charge generation layer. The impedance (R_opt) when an alternating electric field of 100 mV and 0.1 Hz was applied between the conductive support and the gold electrode was further measured under the condition that the surface of the charge generation layer was irradiated with light having an irradiation intensity of 30 pJ / cm ² sec, in the state in which the laser light having a wavelength of 680 nm was oscillated and the charge generation layer and the gold electrode side of the sample were irradiated with light so that the irradiation intensity became 30 pJ / cm ² sec. R_opt / R_dark was calculated from the acquired R_dark and R_opt. The measurement results are shown in Table 11.

(Double positive image evaluation)

The electrophotographic photosensitive component to evaluate the positive double image was mounted on a refurbished mechanism (primary load: DC contact roller load, process speed: 120 mm / sec, laser light irradiation), a power source whose unit pre-luminous radiation was cut by a laser beam printer (trade name: LBP-2510) produced by Canon Corp .; and evaluations of the printed image of initial stage (double image of initial stage) and double positive image in repeated use were performed. The details are as follows.

1. Dual image of initial stage

A process cartridge for a laser printer's cyan color has been refurbished, and a potential probe (model: 6000B-8, manufactured by Trek Japan KK) has been mounted on a developing position; and the manufactured electrophotographic photosensitive component was assembled, and the potential of the central part of the electrophotographic photosensitive component was measured under an ambient temperature of 23 ° C and a humidity of 50% RH using a surface electrometer (model: 344 , produced by Trek Japan KK). The charge voltage and the intensity of the irradiation light were adjusted so that the potential of the dark area (Vd) of the surface potential of the electrophotographic photosensitive component became -600 V and its potential of light area (VI) became -200 V.

Then, the photosensitive electrophotographic component was mounted on the process cartridge for a cyan color of the laser printer, and the process cartridge was mounted on a process cartridge station for cyan, and the images were printed. The images were continuously printed in the order of one sheet of a solid white image, 5 sheets of an image for the double image evaluation, one sheet of a solid black image and 5 sheets of an image for the double image evaluation.

The image for evaluating the double image, as illustrated in FIG. 4, had a

57/77 "blank image" print in its advance part where the square "solid images" were printed, and had a "halftone Keima pattern of a dot" illustrated in FIG. 5A, manufactured after the advance part. In FIG. 4, the “double image” parts were parts where the double images caused by “solid images” may have arisen.

The evaluation of the positive double image was performed by measuring the difference in density between the image density of a halftone image of a Keima pattern of a point described above and the image density of a part of the double image. 10 points of density differences were measured on a sheet with an image for evaluation of the double image by a spectrodensitometer (trade name: XRite 504/508, manufactured by X-Rite Inc.). This operation was performed for all 10 sheets of the image for the evaluation of the double image, and the average of 100 points in total was calculated. The results are shown in Table 11. It is observed that a higher density of part of the double image caused a stronger positive double image. It is proposed that a smaller difference in density Macbeth suppressed the double positive image to a greater extent. A difference in double image density (difference in Macbeth density) of 0.05 or more provided a level of this having a visually obvious difference, and a difference in double image density of less than 0.05 provided a level of this having no no visually obvious difference.

2. Long-term double image

An image print of 1000 continuous sheets was performed using halftone images of a dot pattern illustrated in FIG; 5B described above with the adjusted load voltage and the adjusted irradiation light intensity being set for those determined in the “1. The initial double-stage image ”described above. Within 2 minutes after printing the image of ^the sheet 1000, the image printing was carried out as illustrated in FIG. 4 as in the case of the initial double-stage image, and the positive double-image evaluation (image density evaluation using a spectrodensitometer) after the 1000-sheet image printing has been performed. The results are shown in Table 11.

(Examples 2 to 5)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 1, except changing the thickness of an electron transport layer from 0.53 pm to 0.38 pm (Examples 2), 0.25 pm (Examples 3), 0 , 20 pm (Examples 4) and 0.15 pm (Examples 5) as shown in Table 11. The results are shown in Table 11.

(Example 6)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows.

58/77

The results are shown in Table 11.

parts of the electron transport substance (A101), 5.5 parts of the isocyanate compound (B1: blocking group (H1) = 5.1: 2.2 (mass ratio)), 0.3 part of the resin ( D1) and 0.05 part of dioctyltin laurate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.61 pm.

(Examples 7 to 12)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 6, except for changing the thickness of the electron transport layer from 0.61 pm to those shown in Table 11. The results are shown in Table 11.

(Example 13)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 11.

parts of the electron transport substance (A-101), 2.3 parts of the amine compound (C1-3), 3.3 parts of the resin (D1) and 0.1 part of dodecylbenzenesulfonic acid as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.51 pm.

(Examples 14 to 17)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 13, except for changing the thickness of the electron transport layer from 0.51 pm to those shown in Table 11. The results are shown in Table 11.

(Example 18)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 11.

parts of the electron transport substance (A-101), 1.75 parts of the amine compound (C1-3), 2 parts of the resin (D1) and 0.1 part of dodecylbenzenesulfonic acid

59/77 as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.70 pm.

(Examples 19 to 24)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 18, except in changing the thickness of the electron transport layer from 0.70 pm to those shown in Table 11. The results are shown in Table 11.

(Examples 25 to 45)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 6, except for changing the electron transport substance from Example 6 of (A-101) to the electron transport substance shown in Table 11, and changing the thickness of the electron transport layer. electron transport to those shown in Table 11. The results are shown in Table 11.

(Examples 46 to 66)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 18, except for changing the electron transport substance from Example 18 of (A-101) to the electron transport substance shown in Table 11, and changing the thickness of the electron transport layer. electron transport to those shown in Table 11. The results are shown in Table 11.

(Examples 67 to 72)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 8, except in the alteration of the crosslinking agent (B1: blocking group (H1) =

5.1: 2.2 (mass ratio)) of Example 8 for the crosslinking agents shown in Table 11. The results are shown in Tables 11 and 12.

(Examples 73 and 74)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 21, except in changing the crosslinking agent (C1-3) of Example 21 for the crosslinking agents shown in Table 11. The results are shown in Table 12.

(Example 75)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

parts of the electron transport substance (A-101), 4 parts of the electron

60/77 amine (C1-9), 1.5 part of the resin (D1) and 0.2 part of dodecylbenzenesulfonic acid as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone for that how to prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.35 μητ (Examples 76 and 77)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 75, except in changing the crosslinking agent (C1-9) from Example 75 for the crosslinking agents shown in Table 12. The results are shown in Table 12.

(Examples 78 to 81)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 9, except in changing the resin (D1) from Example 9 to the resins shown in Table 12. The results are shown in Table 12.

(Example 82)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

parts of the electron transport substance (A-124), 2.1 parts of the amine compound (C1-3), 1.2 part of the resin (D1) and 0.1 part of dodecylbenzenesulfonic acid as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.45 gm.

(Examples 83 and 84)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 82, except for changing the electron transporting substance from Example 82 of (A-124) to the electron transporting substance shown in Table 12. The results are shown in Table 12 .

(Example 85)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows.

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The results are shown in Table 12.

parts of the electron transport substance (A-125), 2.1 parts of the amine compound (C1-3), 0.5 part of the resin (D1) and 0.1 part of dodecylbenzenesulfonic acid as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was dipped onto the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to form an electron transport layer having a thickness of 0, 49 gm.

(Example 86)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

6.5 parts of the electron transport substance (A-125), 2.1 parts of the amine compound 15 (C1-3), 0.4 part of the resin (D1) and 0.1 part of dodecylbenzenesulfonic acid as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, 20 and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a 0.49 μητ thickness (Example 87 to 89)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 25, except in changing the thickness of the electron transport layer from 0.49 gm to those shown in Table 12. The results are shown in Table 12.

(Example 90)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. 30 The results are shown in Table 12.

3.6 parts of the electron transport substance (A101), 7 parts of the isocyanate compound (B1: blocking group (H1) = 5.1: 2.2 (mass ratio)), 1.3 part of the resin (D1 ) and 0.05 part of dioctyltin laurate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated

62/77 for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness of 0.53 pm.

(Example 91)

An electrophotographic photosensitive component was manufactured and evaluated as in

Example 1, except changing the thickness of the load-generating layer from 0.53 pm to 0.15 pm. The results are shown in Table 12.

(Example 92)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of a charge-generating layer as follows. The 10 results are shown in Table 12.

oxytitanium phthalocyanine parts that exhibit strong peaks at Bragg angles (2Θ ± 0.2 °) of 9.0 °, 14.2 °, 23.9 ° and 27.1 ° in CuKa X-ray diffractometry were used , and 166 parts of a solution were prepared in which a polyvinyl butyral resin (trade name: Eslec BX-1, produced by Sekisui Chemical Co., Ltd.) was dissolved 15 in a mixed solvent of cyclohexanone: water = 97: 3 to produce a 5% mass solution. The solution and 150 parts of the mixed solvent of cyclohexanone: water = 97: 3 were dispersed together for 4 hours in a sand mill using 400 parts of a 1 πιιτιφ glass globule, and after that, 210 parts of the mixed solvent of cyclohexanone: water = 97: 3 and 260 parts of cyclohexanone were added 20 to thereby prepare a coating liquid for a charge generating layer.

The coating liquid for a charge-generating layer was coated by immersion on the electron transport layer, and the obtained coating film was dried for 10 min at 80 ° C to thereby form a charge-generating layer having a thickness of 0 , 20 pm.

(Example 93)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of the charge-generating layer as follows. The results are shown in Table 12.

parts of a bisazo pigment represented by the following structural formula 30 (11) and 10 parts of a polyvinyl butyral resin (trade name: Eslec BX-1, produced by Sekisui Chemical Co., Ltd.) were mixed and dispersed in 150 parts tetrahydrofuran to thereby prepare a coating liquid for a charge-generating layer. Then, the coating liquid was coated by immersion on the electron transport layer, and the obtained coating film was dried at 110 ° C 35 for 30 min to form a charge-generating layer having a thickness of 0.30 pm .

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(Example 94)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except in changing the benzidine compound represented by the above formula (9-2) of Example 1 to a styryl compound (gap transport substance) represented by the following formula (9 -3). The results are shown in Table 13.

h ₃ C h ₃ c (Examples 95 and 96)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 1, except in changing the thickness of the gap transport layer from 15 pm to 10 pm (Example 95) and 25 pm (Example 96). The results are shown in Table 13.

(Example 97)

An aluminum cylinder (JIS-A3003, an aluminum alloy) 260.5 mm long and 30 mm in diameter was produced to be a support (conductive support).

Then, 214 parts of a titanium oxide (TiO ₂ ) particle coated with an oxygen-deficient tin oxide (SnO ₂ ) as a metal oxide particle, 132 parts of a phenolic resin (trade name: Plyophen J-325 ) as a binder resin, and 98 parts of 1-methoxy-2-propanol as a solvent were placed in a sand mill using 450 parts of a 0.8 mm diameter glass globule and subjected to a dispersion under the conditions of a rotation frequency of 2000 rpm, a dispersion treatment time of 4.5 hours and a determined temperature of a cooling water of 18 ° C to obtain a dispersion liquid. The glass globule was removed from the dispersion liquid by a mesh (mesh opening: 150 pm). A particle of silicone resin (trade name: Tospearl 120, produced by Momentive Performance Materials Inc., average particle diameter: 2 pm) as a surface roughness material was added to the dispersion liquid after removing the glass globule so to become 10% by weight in relation to the total mass of the metal oxide particle and the binder resin in the dispersion liquid; and an oil

64/77 of silicone (trade name: SH28PA, produced by Dow Corning Toray Co., Ltd.) as a leveling agent was added to the dispersion liquid in order to become 0.01% by weight relative to the total mass of the particle of metal oxide and binder resin in the dispersion liquid; and the resulting mixture was stirred to thereby prepare a coating liquid for a conductive layer. The coating liquid for a conductive layer was dipped onto a support, and the coating film obtained was dried and heat cured for 30 min at 150 ° C to thereby form a conductive layer having a thickness of 30 pm.

Then 6.2 parts of the electron transport substance (A157), 8.0 parts of the crosslinking agent (B1: blocking group (H5) = 5.1: 2.9 (mass ratio)), 1, 1 part of the resin (D25) and 0.05 part of zinc (II) hexanoate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for a electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer (layer of electron transport). base) having a thickness of 0.53 pm. The content of the electron transport substance in relation to the total mass of the electron transport substance, the crosslinking agent and the resin was 34% by weight.

Then, a charge generating layer having a thickness of 0.15 pm was formed as in Example 1.

parts of the triaryl amine compound represented by the structural formula above (9-

1), 1 part of a benzidine compound (gap transport substance) represented by the following structural formula (18), 3 parts of an E polyester resin (weighted average molecular weight: 90000) having a structural repeating unit represented by following formula (24), and a structural repeating unit represented by the following formula (26) and a structural repeating unit represented by the following formula (25) in a 7: 3 ratio, and 7 parts of a polyester resin F ( weighted average molecular weight: 120000) having a structural repeating unit represented by the following formula (27) and a structural repeating unit represented by the following formula (28) in a 5: 5 ratio were dissolved in a mixed solvent of 30 parts of dimethoxymethane and 50 parts of orthoxylene to thereby prepare a coating liquid for a gap transport layer. Here, the content of the structural repeating unit represented by the following formula (24) in polyester resin E was 10% by weight, and the content of the structural repeating units represented by the following formulas (25) and (26) was 90 % in large scale.

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Γο ο

The coating liquid for a gap transport layer was dipped onto the load-generating layer, and dried for 1 hour at 120 ° C to thereby form a gap transport layer having a thickness of 16 pm. The gap transport layer formed was confirmed to have a domain structure in which a matrix containing the gap transport substance and polyester resin F contained polyester resin E.

The evaluation was carried out as in Example 1. The results are shown in Table 13.

(Example 98)

An electrophotographic photosensitive component was manufactured as in Example 1, except for the formation of a gap transport layer as follows. The results are shown in Table 13.

parts of the triaryl amine compound represented by the structural formula above (9-

1), 1 part of the benzidine compound represented by the structural formula above (18), 10 parts of a polycarbonate resin G (weighted average molecular weight: 70000) having a structural repeating unit represented by the following formula (29), and 0.3 part of a polycarbonate resin H (weighted average molecular weight: 40000) having a structural repeating unit represented by the following formula (29), a structural repeating unit represented by the following formula (30) and a structure of at least a terminal represented by the following formula (31) were dissolved in a mixed solvent of 30 parts of dimethoxymethane and 50 parts of orthoxyylene for that

66/77 how to prepare a coating liquid for a gap transport layer. Here, the total mass of the structures represented by the following formulas (30) and (31) in the polycarbonate resin H was 30% by mass. The coating liquid for a gap transport layer was dipped onto the charge generating layer, and dried for 1 hour at 120 ° C to thereby form a gap transport layer having a thickness of 16 pm.

(Example 99)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 98, except to change 10 parts of polycarbonate resin G (weighted average molecular weight: 70000) in the coating liquid to a gap transport layer of Example 98 for 10 parts of resin polyester F (weighted average molecular weight: 120000). The results are shown in Table 13.

(Example 100)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 97, except for the formation of a conductive layer as follows. The results are shown in Table 13.

207 parts of a titanium oxide (TiO ₂ ) particle coated with a tin oxide (SnO ₂ ) impregnated with phosphorus (P) as a metal oxide particle, 144 parts of a phenolic resin (trade name: Plyophen J- 325) as a binder resin, and 98 parts of 1-methoxy-2-propanol as a solvent were placed in a sand mill using 450 parts of a 0.8 mm diameter glass globule and subjected to a treatment dispersion under the conditions of a rotation frequency of 2000 rpm, a dispersion treatment time of 4.5 hours and a determined temperature of a cooling water of 18 ° C to obtain a dispersion liquid. The glass globule was removed from the dispersion liquid by a mesh (mesh opening: 150 pm).

A particle of silicone resin (trade name: Tospearl 120) as a surface roughness material was added to the dispersion liquid after removal of the glass globule so as to become 15% by mass relative to the total mass of the oxide particle. metal and binder resin in the dispersion liquid; and a silicone oil

67/77 (trade name: SH28PA) as a leveling agent was added to the dispersion liquid so as to become 0.01% by weight relative to the total mass of the metal oxide particle and the binder resin in the liquid. dispersal; and the resulting mixture was stirred to thereby prepare a coating liquid for a conductive layer. The coating liquid for a conductive layer was dipped onto a support, and the coating film obtained was dried and heat cured for 30 min at 150 ° C to thereby form a conductive layer having a thickness of 30 pm.

(Examples 101 to 119)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 97, except in changing the electron transport substance from Example 97 of (A157) to the electron transport substance shown in Table 13. The results are shown in Table 13.

(Comparative Example 1)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

2.4 parts of the electron transport substance (A101), 4.2 parts of the isocyanate compound (B1: blocking group (H1) = 5.1: 2.2 (mass ratio)), 5.4 parts of the resin (D1) and 0.05 part of dioctyltin laurate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer . The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.53 pm.

(Comparative Example 2)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

3.2 parts of the electron transport substance (A101), 5 parts of the isocyanate compound (B1: blocking group (H1) = 5.1: 2.2 (mass ratio)), 4.2 parts of the resin (D1) and 0.05 part of dioctyltin laurate as a catalyst were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form a layer of

68/77 electron transport having a thickness of 0.53 pm.

(Comparative Examples 3 and 4)

The electrophotographic photosensitive components were manufactured and evaluated as in Comparative Example 2, except in changing the thickness of the electron transport layer from 0.53 pm to 0.40 pm and 0.32 pm. The results are shown in Table 12.

(Comparative Examples 5 to 8)

The electrophotographic photosensitive components were manufactured and evaluated as in Example 1, except in changing the thickness of the electron transport layer from 0.53 pm to 0.78 pm, 1.03 pm, 1.25 pm and 1.48 pm. The results are shown in the Table

12.

(Comparative Example 9)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

parts of the electron transport substance (A225), 3 parts of hexamethylene diisocyanate and 4 parts of the resin (D1) were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a liquid of coating for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness from 1.00 pm.

(Comparative Example 10)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 12.

parts of the electron transport substance (A124), 2.5 parts of 2,4-toluene diisocyanate and 2.5 parts of a poly (p-hydroxystyrene) (trade name: Malkalinker, produced by Maruzen Petrochemical Co., Ltd .) were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form an electron transport layer having a thickness 0.40 μηη.

(Comparative Example 11)

An electrophotographic photosensitive component was manufactured and evaluated as in

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Example 1, except in the formation of an electron transport layer as follows. The results are shown in Table 12.

parts of the electron transport substance (A124), 2 parts of 2,4-toluene diisocyanate and 1 part of a poly (p-hydroxystyrene) were dissolved in a mixed solvent of 100 parts of dimethylacetoamide and 100 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 160 ° C to be polymerized to form a 10 electron transport layer having a thickness of 0.40 gm.

Table 11

Example Electron transport substance Crosslinking agent Resin transnorte substance ratio base layer thickness R_opt / R_dark dual image of initial stage double image after 1000 slides difference between double images 1 A101 B1: H1 D1 33% 0.53 0.85 0.03 0.03 0.00 2 A101 B1: H1 D1 33% 0.38 0.85 0.03 0.03 0.00 3 A101 B1: H1 D1 33% 0.25 0.85 0.03 0.03 0.00 4 A101 B1: H1 D1 33% 0.20 0.85 0.03 0.03 0.00 5 A101 B1: H1 D1 33% 0.15 0.95 0.04 0.05 0.01 6 A101 B1: H1 D1 41% 0.61 0.75 0.02 0.02 0.00 7 A101 B1: H1 D1 41% 0.52 0.75 0.02 0.02 0.00 8 A101 Β1.Ή1 D1 41% 0.40 0.85 0.03 0.03 0.00 9 A101 B1: H1 D1 41% 0.26 0.85 0.03 0.03 0.00 10 A101 B1: H1 D1 41% 0.70 0.85 0.03 0.03 0.00 11 A101 B1: H1 D1 41% 0.90 0.90 0.04 0.05 0.01 12 A101 B1: H1 D1 41% 1.10 0.95 0.04 0.05 0.01 13 A101 C1-3 D1 47% 0.51 0.75 0.02 0.02 0.00 14 A101 C1-3 D1 47% 0.45 0.75 0.01 0.01 0.00 15 A101 C1-3 D1 47% 0.34 0.75 0.02 0.02 0.00 16 A101 C1-3 D1 47% 0.70 0.85 0.02 0.02 0.00 17 A101 C1-3 D1 47% 0.91 0.93 0.03 0.04 0.01 18 A101 C1-3 D1 57% 0.70 0.85 0.03 0.03 0.00 19 A101 C1-3 D1 57% 0.58 0.75 0.02 0.02 0.00 20 A101 C1-3 D1 57% 0.50 0.75 0.02 0.02 0.00 21 A101 C1-3 D1 57% 0.35 0.85 0.03 0.03 0.00 22 A101 C1-3 D1 57% 0.92 0.90 0.03 0.04 0.01 23 A101 C1-3 D1 57% 1.11 0.93 0.03 0.04 0.01 24 A101 C1-3 D1 57% 1.32 0.95 0.04 0.05 0.01 25 A106 B1: H1 D1 41% 0.52 0.75 0.02 0.02 0.00 26 A125 B1: H1 D1 41% 0.52 0.75 0.02 0.02 0.00 27 A125 B1: H1 01 41% 0.20 0.75 0.02 0.02 0.00 28 A125 B1: H1 D1 41% 0.70 0.75 0.02 0.02 0.00 29 A136 B1: H1 D1 41% 0.51 0.75 0.02 0.02 0.00 30 A136 B1: H1 D1 41% 0.21 0.75 0.02 0.02 0.00 31 A136 B1: H1 D1 41% 0.69 0.75 0.02 0.02 0.00 32 A116 B1: H1 D1 41% 0.52 0.85 0.03 0.03 0.00 33 A119 B1: H1 D1 41% 0.52 0.85 0.03 0.03 0.00 34 A120 B1: H1 D1 41% 0.52 0.85 0.03 0.03 0.00

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Table 12

example substance ^ and transport, deelectrons crosslinking agent resin electron transport substance relationship base layer thickness Ropt / R_daik dual initial stage image image, double 'after 1000 slides difference between double images 55 A136 C1-3 D1 57% 0.90 075 0.02 0.02 0.00 56 A136 Hey-3 D1 57% 1.12 0.77 0.02 0.02 0.00 57 ÃÍ36 C1-3 01 57% 1.30 0.80 0.02 0.02 0.00 58 A201 C1-3 D1 57% 1.30 0.85 0.03 0.03 0.00 59 A306 C1-3 D1 57% 1.30 085 0.03 0.03 0.00 60 A306 C1-3 D1 57% 1.30 0.75 0.02 0.02 0/00 61 A404 C1-3 01 57% 1.30 0.75 0.02 0.02 0.00 62 A510 C1-3 D1 57% 1.30 0.75 0.02 0.02 0.00 63 AOOO C1-3 01 57 ^2nd / o 1.30 0.85 0.03 0.03 0.00 64 A709 C1-3 D1 57% 1.30 0.85 0.03 0.03 0.00 65 A807 C1-3 D1 57% 1.30 0.75 0.02 0.02 0.00 66 A902 C1-3 D1 57% 1.30 075 0.02 0.02 0.00 67 Aiõ'1 B1: H2 01 41% 0.40 0.85 0.03 0.03 0.00 68 A1oi B1: H3 01 41% 0.40 0.85 0.03 0.03 0.00 69 A101 B4: H1 D1 41% 0.40 0.85 0.03 0.03 0:00 70 A101 B5: H1 D1 41% 0.40 0.85 0.03 0.03 0.00 71 A101 B7: H1 D1 41% 0.40 0.85 0.03 0.03 0.00 72 A101 B12: H1 D1 41% 0.40 0.85 0.03 0.03 0.00 73 A1Ô1 C1-1 01 57% 0.35 0.75 0.02 0.02 0.00 74 A101 C1-7 D1 57% 0.35 0.75 0.02 0.02 0.00 75 A101 C1-9 01 41% 0.35 0.75 0.02 0.02 0.00 76 A101 C2-1 D1 41% 0.35 0.75 0.02 0.02 0.00 77 õà-5 D1 4T% 0.35 0.75 0.02 0.02 0.00 78 A1Õ1 Β1Ή1 D3 41% 0.26 0.85 0.03 0.03 0.00 79 A101 B1: H1 D5 41% 0.26 0.85 0.03 0.03 0.00 80 A101 B1: H1 D19 41% 0.26 0.85 0.03 0.03 0.00 81 A101 Β1Ή1 D20 41% 0.26 0.85 0.03 0.03 0.00 82 A124 C1-3 D1 65% 0.45 0.65 0.01 0.01 0.00 83 Αβΰ C1-3 01 65% 0.45 065 0.01 0.01 0.00 84 CTT D1 65% Õ75 0.65 0.01 0.01 0.00 85 A125 C1-3 D1 70% 0.49 0.65 0.01 0.01 0.00 86 A125 C1-3 D1 72% 0.49 0.75 0.02 0.02 0.00 87 A125 C1-3 01 70% 0.70 075 0.02 0.02 0.00 88 Ã125 hello 01 7% 0.95 0.75 0.02 0.02 0.00 89 Hey CiT 01 70% 1.24 0.80 0.03 0.03 0.00 90 A101 B1: H1 D1 30% 0.53 0.95 0.04 0.05 0.01 91 A101 B1: H1 D1 33% 0.15 0.85 0.03 0.03 0.00 92 Hey B1: AI 01 33% 0.53 0.95 0.04 0.05 0.01 93 ΕΠΤΠ 01 53% 0.53 0.85 0.03 0.03 0.00 comparative example 1 A101 B1: H1 D1 20% 0.53 0.99 0.1 0.13 0.03 comparative example 2 A101 B1: H1 D1 25% 053 0.98 0.07 0.10 0.03 example.com- bread 3 A101 B1-.HÍ D1 25% 0.40 0.98 0.07 0.10 0.03 example with * parative 4 ΑΊ01 B1: H1 D1 25% 0.32 0.97 0.07 0.09 0.02 comparative example 5 A101 B1: H1 D1 33% 0.78 0.98 0.06 0.09 003 example comjsaratíxõ. 6 A101 B1: H1 D1 33% 1.03 0.99 0.07 0.10 0.03 comparative example 7 A101 Β1Ή1 D1 33% 1.25 0.99 0.08 0.11 0.03 comparative example g A101 B1: H1 D1 33% 1.48 1 0.09 0.13 0.04 comparative example g A225 hexamethylene diisodanate DL 36% 1.00 0.99 0.07 0.10 0.03 comparative example Ί Q A124 diisocyanate of 2,4-toluene poly (p- '' hydroxystyrene) 50% 0.40 0.99 0.07 0.10 0.03 comparative example ji A124 diisocyanate 2.4-toluene poly (p * hydroxystyrene) 70% 0.40 0.98 0.06 0.09 0.03

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Table 13

Example electron transport substance crosslinking agent Resin electron transport substance ratio base layer thickness R_opt / R_dark dual initial stage image double image after 1000 slides difference between double images 94 A101 B1: H1 D1 33% 0.53 0.85 0.03 0.03 0.00 95 A106 B1: H6 D14 33% 0.53 0.85 0.03 0.03 0.00 96 A107 B1: H7 D15 33% 0.53 0.85 0.04 0.04 0.00 97 A157 B1: H5 D25 41% 0.47 0.80 0.03 0.03 0.00 98 A157 B1: H5 D25 41% 0.47 0.80 0.03 0.03 0.00 99 A157 B1: H5 D25 41% 0.47 0.80 0.03 0.03 0.00 100 A157 B1: H5 D25 41% 0.47 0.80 0.04 0.04 0.00 101 A124 B1: H5 D25 41% 0.47 0.80 0.04 0.04 0.00 102 A125 B1: H5 D25 41% 0.47 0.70 0.03 0.03 0.00 103 A152 B1: H5 D25 41% 0.47 0.85 0.04 0.04 0.00 104 A159 B1: H5 D25 41% 0.47 0.70 0.03 0.03 0.00 105 A164 B1: H5 D25 41% 0.47 0.65 0.03 0.03 0.00 106 A166 B1: H5 D25 41% 0.47 0.85 0.04 0.04 0.00 107 A167 B1: H5 D25 41% 0.47 0.80 0.04 0.04 0.00 108 A168 B1: H5 D25 41% 0.47 0.70 0.03 0.03 0.00 109 A172 B1: H5 D25 41% 0.47 0.75 0.03 0.03 0.00 110 A177 B1: H5 D25 41% 0.47 0.65 0.03 0.03 0.00 111 A178 B.H5 D25 41% 0.47 0.65 0.03 0.03 0.00 112 A207 B1: H5 D25 41% 0.47 0.85 0.04 0.04 0.00 113 A315 B1: H5 D25 41% 0.47 0.85 0.04 0.04 0.00 114 A402 B1: H5 D25 41% 0.47 0.70 0.03 0.03 0.00 115 A509 B1: H5 D25 41% 0.47 0.70 0.03 0.03 0.00 116 A602 B1: H5 D25 41% 0.47 0.80 0.04 0.04 0.00 117 A707 B1: H5 D25 41% 0.47 0.65 0.03 0.03 0.00 118 A819 B1: H5 D25 41% 0.47 0.65 0.03 0.03 0.00

(Comparative Example 12)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows.

The results are shown in Table 14.

parts of the electron transport substance (A922), 13.5 parts of an isocyanate compound (Sumidule 3173, produced by Sumitomo Bayer Urethane Co., Ltd.), 10 parts of a butyral resin (BM-1, produced by Sekisui Chemical Co., Ltd.) and 0.005 part of dioctyltin laurate as a catalyst were dissolved in a solvent of 120 parts of methyl ethyl ketone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 40 min at 170 ° C to be polymerized to form an electron transport layer having a 15 thickness of 1.00 pm.

(Comparative Example 13)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows.

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The results are shown in Table 14.

parts of the electron transport substance (A101) and 2.4 parts of a melamine resin (Yuban 20HS, produced by Mitsui Chemicals Inc.) were dissolved in a mixed solvent of 50 parts of tetrahydrofuran and 50 parts of methoxypropanol to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 60 min at 150 ° C to be polymerized to form an electron transport layer having a thickness from 1.00 pm.

(Comparative Example 14)

An electrophotographic photosensitive component was manufactured and evaluated as in Comparative Example 12, except in changing the thickness of the electron transport layer from 1.00 pm to 0.50 pm. The results are shown in Table 14.

(Comparative Example 15)

An electrophotographic photosensitive component was manufactured and evaluated as in

Comparative Example 12, except changing the melamine resin (Yuban 20HS, produced by Mitsui Chemicals Inc.) from the electron transport layer to the phenolic resin (Plyophen J-325, produced by DIC Corporation). The results are shown in Table 14.

(Comparative Example 16)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

parts of a mixture of a compound having a structure represented by the following formula (12-1) and a compound having a structure represented by the following formula (12-2) were dissolved in a mixed solvent of 30 parts of N-methyl-2pyrrolidone and 60 parts of cyclohexanone to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 30 min at 150 ° C to be polymerized to form an electron transport layer having a structure represented by the following formula (12-3) and having a thickness of 0.20 pm.

73Π7

(Comparative Examples 17 and 18)

The electrophotographic photosensitive components were manufactured and evaluated as in Comparative Example 16, except in changing the thickness of the electron transport layer from 0.20 μιτι to 0.30 pm and 0.60 pm. The results are shown in Table 14.

(Comparative Example 19)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

parts of an electron transport substance represented by the following formula (13) were dissolved in 60 parts of toluene to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the coating film obtained was irradiated with electron beams under the conditions of an accelerating voltage of 150 kV and an irradiation dose of 15 10 Mrad to be polymerized to form an electron transport layer having a thickness of 1.00 pm.

(Comparative Example 20)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. 20 The results are shown in Table 14.

parts of the electron transport substance represented by the above formula (13), 5 parts of trimethylolpropane triacrylate (Kayarad TMPTA, Nippon Kayaku Co., Ltd.) and 0.1 part of AIBN (2,2-azobisisobutyronitrile) were dissolved in 190 parts of tetrahydrofuran (THF) to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the

74/77 coating obtained was heated for 30 min at 150 ° C to be polymerized to form an electron transport layer having a thickness of 0.80 μητ (Comparative Example 21)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

parts of the electron transport substance represented by the above formula (13) and 5 parts of a compound represented by the following formula (14) were dissolved in 60 parts of toluene to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the coating film obtained was irradiated with electron beams under the conditions of an accelerating voltage of 150 kV and an irradiation dose of 10 Mrad to be polymerized to form an electron transport layer having a thickness of 1.00 μητ

O çh ₃ o-ch _{2 ch ch} h ₂ c = ch-co-ch ₂ -c — CH V ^z _(ΛΔΛ

CH ₃ O-CH ₂ > 3Η ₂ -oc-ch = ch ₂ o

(Comparative Example 22)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

An electron transport layer (a constitution of Example 1 of the National Publication of International Patent Application No. 2009-505156) was formed using a block copolymer represented by the following structure, blocked isocyanate and a vinyl chloride-vinyl acetate copolymer to form an electron transport layer having a thickness of 0.32 μΐυ.

(Comparative Example 23)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

75/77 parts of the electron transport substance (A101) and 5 parts of a polycarbonate resin (Z200, produced by Mitsubishi Gas Chemical Co., Inc.) were dissolved in a mixed solvent of 50 parts of dimethylacetoamide and 50 parts of chlorobenzene to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was coated by immersion on the conductive layer, and the obtained coating film was heated for 30 min at 120 ° C to be polymerized to form an electron transport layer having a thickness 1.00 μητ (Comparative Example 24)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

parts of an electron transport substance (pigment) represented by the following structural formula (16) were added to a liquid in which 5 parts of the resin (D1) were dissolved in 200 parts of methyl ethyl ketone, and were subjected to a treatment of dispersion for 3 hours using a sand mill to thereby prepare a coating liquid for an electron transport layer. The coating liquid for an electron transport layer was dipped onto the conductive layer, and the obtained coating film was heated for 10 min at 100 ° C to form an electron transport layer having a thickness of 1, 50 pm.

(Comparative Example 25)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

An electron transport layer was formed using a coating liquid for an electron transport layer in which a polymer of an electron transport substance described in example 1 of Japanese Patent No. 4594444 was dissolved in a solvent, to form an electron transport layer having a thickness of 2.00 μίτι.

(Comparative Example 26)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

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An electron transport layer was formed using a particle of a copolymer containing an electron transport substance described in Example 1 of Japanese Patent No. 4,594,444, to form an electron transport layer having a thickness of 1.00 pm.

(Comparative Example 27)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

An electron transport layer (a constitution of Example 1 of Japanese Open Patent Application No. 2006-030698) was formed using a zinc oxide pigment that was subjected to a surface treatment with a coating agent. silane coupling, alizarin (A922), a blocked isocyanate compound and a butyral resin, to form a 25 pm electron transport layer.

(Comparative Example 28)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

parts of a polyamide resin (6 N-methoxymethylated nylon resin (trade name: Toresin EF-30T, produced by Nagase ChemteX Corp., degree of polymerization: 420, methoxymethylation ratio: 36.8%)) were dissolved in 100 parts of methanol and 100 parts of 1-butanol to thereby prepare a coating liquid for a base layer. The coating liquid for a base layer was dipped onto the conductive layer, and the obtained coating film was dried at 100 ° C for 10 min to form a base layer.

(Comparative Example 29)

An electrophotographic photosensitive component was manufactured and evaluated as in Example 1, except for the formation of an electron transport layer as follows. The results are shown in Table 14.

An electron transport layer (base layer using an electron transport pigment, a polyvinyl butyral resin, and a curable electron transport substance having an alkoxysilyl group) described in example 25 of the Japanese Open Patent Application No. H11-119458 has been formed.

77/77 (Table 14)

electron transport layer thickness R_opt / R_dark dual initial stage image double image after 1000 slides difference between duolas images Comparative Example 1.00 0.99 0.10 0.13 0.03 Comparative Example 1.00 1.00 0.07 0.10 0.03 Comparative Example 0.50 1.00 0.06 0.10 0.04 Comparative Example 1.00 1.01 0.08 0.12 0.04 Comparative Example 0.20 0.99 0.07 0.10 0.03 Comparative Example 0.30 0.99 0.07 0.10 0.03 Comparative Example 0.60 1.00 0.08 0.11 0.03 Comparative Example 1.00 0.99 0.09 0.12 0.03 Comparative Example 0.80 0.99 0.09 0.13 0.04 Comparative Example 1.00 0.99 0.10 0.13 0.03 Comparative Example 0.32 0.99 0.07 0.10 0.03 Comparative Example 1.00 0.99 0.09 0.13 0.04 Comparative Example 1.50 1.00 0.10 0.13 0.03 Comparative Example 2.00 1.02 0.10 0.14 0.04 Comparative Example 1.00 1.10 0.11 0.14 0.03 Comparative Example 25.00 1.05 0.11 0.15 0.04 Comparative Example 0.80 1.10 0.05 0.12 0.07

Although the present invention has been described with reference to the exemplary embodiments, it should be understood that the invention is not limited by the exemplary embodiments disclosed. The scope of the following claims must be in accordance with the broadest interpretation to cover all such modifications and equivalent structures and functions.

Claims (11)

1. Photosensitive electrophotographic component characterized by comprising: a laminated body, and a gap transport layer formed on the laminated body, wherein the laminated body comprises: a conductive support, an electron transport layer formed on the support, and a charge generation layer formed on the electron transport layer, and in which the laminated body meets the following expression (1): R_opt / R_dark <0.95 (1) where, in expression (1), R_opt represents the impedance of the laminated body measured by the steps of: form, on a surface of the charge generation layer, a circular gold electrode having a thickness of 300 nm and a diameter of 10 mm by cathodic sublimation, and apply, between the conductive support and the circular gold electrode , an alternating electric field having a voltage of 100 mV and a frequency of 0.1 Hz while radiating the surface of the charge generation layer with light having an intensity of 30 pJ / cm ² -s, and measuring the impedance, and R_dark represents the impedance of the laminated body measured by the steps of: forming, on a surface of the charge generation layer, an electrode of another in circular shape having a thickness of 300 nm and a diameter of 10 mm by cathodic sublimation, and apply, between the conductive support and the electrode of another in a circular shape, an alternating electric field having a voltage of 100 mV and a frequency of 0.1 Hz without radiating the surface of the charge generation layer with light, and measuring the impedance. 2. Photosensitive electrophotographic component according to claim 1, characterized by the fact that the laminated body meets the following expression (2): 0 <R_opt / R_dark <0.85 (2) 3. Electrophotographic photosensitive component according to claim 1 or 2, characterized by the fact that the electron transport layer has a thickness of 0.2 pm or more and 0.7 pm or less. 4. Photosensitive electrophotographic component according to any one of claims 1 to 3, characterized by the fact that the electron transport layer is Petition 870160010098, of March 22, 2016, p. 5/7 2/2 a layer comprising a polymerized product of a composition comprising an electron transport substance having a polymerizable functional group, a thermoplastic resin having a polymerizable functional group, and a crosslinking agent. 5. Electrophotographic photosensitive component according to claim 4, characterized by the fact that the electron transport substance having a polymerizable functional group has a content of 30% by weight or more and 70% by weight or less in relation to mass total composition. 6. Photosensitive electrophotographic component according to claim 4 or 5, 10 characterized by the fact that the polymerizable functional group of the electron transport substance is a hydroxy group, a thiol group, an amino group, a carboxyl group or a methoxy group. 7. Photosensitive electrophotographic component according to claim 4 or 5, characterized by the fact that the cross-linking agent is a compound having 3 to 6 groups 15 of an isocyanate group, a compound having 3 to 6 groups of a blocked isocyanate group or a compound having 3 to 6 groups of a monovalent group represented by -CH ₂ -OR ¹ (R ¹ represents an alkyl group). 8. Electrophotographic photosensitive component according to any one of claims 1 to 7, characterized by the fact that the charge generation layer 20 comprises at least one charge generating substance selected from the group consisting of phthalocyanine pigments and azo pigments. 9. Photosensitive electrophotographic component according to any one of claims 1 to 8, characterized by the fact that the gap transport layer comprises at least one gap transport substance selected from the group 25 consisting of triarylamine compounds, benzidine compounds and styryl compounds. 10. Detachable process cartridge attached to a main body of an electrophotographic device, characterized by the fact that the process cartridge fully supports: the electrophotographic photosensitive component of the type defined in any one of the claims 1 to 9, and at least one unit selected from the group consisting of a charge unit, a developing unit, a transfer unit and a cleaning unit. 11. Electrophotographic apparatus characterized by the fact that it comprises an electrophotographic photosensitive component of the type defined in any of the 35 claims 1 to 9, and a charge unit, a light irradiation unit, a developing unit and a transfer unit.