CN108572518B - Electrophotographic photoreceptor - Google Patents
Electrophotographic photoreceptor Download PDFInfo
- Publication number
- CN108572518B CN108572518B CN201810158538.3A CN201810158538A CN108572518B CN 108572518 B CN108572518 B CN 108572518B CN 201810158538 A CN201810158538 A CN 201810158538A CN 108572518 B CN108572518 B CN 108572518B
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- Prior art keywords
- compound
- photosensitive layer
- group
- general formula
- electrophotographic photoreceptor
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- MXNUCYGENRZCBO-UHFFFAOYSA-M sodium;ethene;2-methylprop-2-enoate Chemical compound [Na+].C=C.CC(=C)C([O-])=O MXNUCYGENRZCBO-UHFFFAOYSA-M 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
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Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
- G03G5/0648—Heterocyclic compounds containing two or more hetero rings in the same ring system containing two relevant rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an electrophotographic photoreceptor. An electrophotographic photoreceptor includes a conductive substrate and a single photosensitive layer. The photosensitive layer contains at least a charge generator and a compound represented by the following general formula (1). In the general formula (1), R1Represents nitro, C1-C8 alkyl, C6-C14 aryl which may have C1-C8 alkyl, C7-C20 aralkyl, C3-C10 cycloalkyl or C1-C6 alkoxy. R2、R3、R4And R5Each independently represents a hydrogen atom, a nitro group, a C1-C8 alkyl group, a C6-C14 aryl group which may have a C1-C8 alkyl group, a C7-C20 aralkyl group, a C3-C10 cycloalkyl group or a C1-C6 alkoxy group. m represents an integer of 0 to 5 inclusive. When m represents an integer of 2 to 5, a plurality of R1May be the same or different.
Description
Technical Field
The present invention relates to an electrophotographic photoreceptor.
Background
Electrophotographic photoreceptors are used in electrophotographic image forming apparatuses. Examples of the electrophotographic photoreceptor include a laminated electrophotographic photoreceptor and a single-layer electrophotographic photoreceptor. The laminated electrophotographic photoreceptor comprises: a charge generation layer having a function of generating charges and a charge transport layer having a function of transporting charges are used as the photosensitive layer. The single-layer electrophotographic photoreceptor includes a single photosensitive layer as a photosensitive layer, and the single photosensitive layer has a charge generating function and a charge transporting function.
The photosensitive layer contained in the electrophotographic photoreceptor contains, for example, a naphthalenetetracarboxylic acid diimide derivative having a structure represented by the chemical formula (E-1) as an electron transporting substance.
[ CHEM 1 ]
Disclosure of Invention
However, the inventors of the present invention have studied and found that sensitivity characteristics are insufficient with respect to an electrophotographic photoreceptor containing a naphthalenetetracarboxylic acid diimide derivative having a structure represented by the chemical formula (E-1) in a photosensitive layer.
In view of the above-described problems, an object of the present invention is to provide an electrophotographic photoreceptor having excellent sensitivity characteristics.
The electrophotographic photoreceptor of the present invention includes a conductive substrate and a single photosensitive layer. The photosensitive layer contains at least a charge generating agent and a compound represented by the following general formula (1).
[ CHEM 2 ]
In the general formula (1), R1Represents nitro, C1-C8 alkyl, C6-C14 aryl which may have C1-C8 alkyl, C7-C20 aralkyl, C3-C10 cycloalkyl or C1-C6 alkoxy. R2、R3、R4And R5Each independently represents a hydrogen atom, a nitro group, a C1-C8 alkyl group, a C6-C14 aryl group which may have a C1-C8 alkyl group, a C7-C20 aralkyl group, a C3-C10 cycloalkyl group or a C1-C6 alkoxy group. m represents an integer of 0 to 5 inclusive. When m represents an integer of 2 to 5, a plurality of R1May be the same or different.
The electrophotographic photoreceptor of the present invention has excellent sensitivity characteristics.
Drawings
Fig. 1(a), 1(b) and 1(c) are cross-sectional views of an example of an electrophotographic photoreceptor according to an embodiment of the present invention.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments. The present invention can be implemented with appropriate modifications within the scope of the object of the present invention. Note that, although the description may be omitted as appropriate, the gist of the present invention is not limited thereto.
Hereinafter, the compound and its derivatives may be collectively referred to by adding "class" to the compound name. When a "class" is added after the compound name to indicate the polymer name, the repeating unit indicating the polymer is derived from the compound or a derivative thereof.
Hereinafter, unless otherwise specified, C1-C8 alkyl group, C1-C6 alkyl group, C1-C3 alkyl group, C1-C6 alkoxy group, C1-C3 alkoxy group, C6-C14 aryl group, C6-C10 aryl group, C3-C10 cycloalkyl group, C5-C7 cycloalkyl group and C7-C20 aralkyl group have the following meanings, respectively.
The C1-C8 alkyl groups, C1-C6 alkyl groups and C1-C3 alkyl groups are all straight-chain or branched-chain and unsubstituted. C1-C8 alkyl such as: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 2-ethylpropyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2, 2-dimethylpropyl, 1, 2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3-dimethylbutyl, 1, 2-trimethylpropyl, 1, 2-trimethylpropyl, 2-dimethylpropyl, 1, 2-dimethylpropyl, 1, 2-dimethylbutyl, 2-dimethylpropyl, 2-dimethylp, 1-ethylbutyl, 2-ethylbutyl, 3-ethylbutyl, heptyl, and octyl. Examples of C1-C6 alkyl are C1-C6 groups of the groups mentioned in the examples of C1-C8 alkyl. Examples of C1-C3 alkyl are C1-C3 groups of the groups mentioned in the examples of C1-C8 alkyl.
The C1-C6 alkoxy and C1-C3 alkoxy groups are both straight-chain or branched-chain and unsubstituted. C1-C6 alkoxy, for example: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy and hexyl. Examples of C1-C3 alkoxy are C1-C3 groups of the groups mentioned in the examples of C1-C6 alkoxy.
The C6-C14 aryl and the C6-C10 aryl are both unsubstituted. C6-C14 aryl, for example: phenyl, naphthyl, indacenyl, biphenylene, acenaphthylene, anthryl and phenanthryl. C6-C10 aryl radicals such as phenyl and naphthyl.
Both the C3-C10 cycloalkyl and the C5-C7 cycloalkyl are unsubstituted. C3-C10 cycloalkyl for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of C5-C7 cycloalkyl are the C5-C7 groups of the groups mentioned in the examples of C3-C10 cycloalkyl.
C7-C20 aralkyl is unsubstituted. C7-C20 aralkyl is, for example, C1-C6 alkyl having C6-C14 aryl.
< electrophotographic photoreceptor >
The present embodiment relates to an electrophotographic photoreceptor (hereinafter, may be referred to as a photoreceptor). Hereinafter, the structure of the photoreceptor 100 will be described with reference to fig. 1. Fig. 1 is a cross-sectional view of an example of a photoreceptor 100 according to the present embodiment.
As shown in fig. 1(a), the photoreceptor 100 includes, for example, a conductive substrate 101 and a photosensitive layer 102. The photosensitive layer 102 is a single layer (one layer). The photoreceptor 100 is a single-layer electrophotographic photoreceptor having a single photosensitive layer 102.
As shown in fig. 1(b), the photoreceptor 100 may include a conductive substrate 101, a photosensitive layer 102, and an intermediate layer 103 (undercoat layer). The intermediate layer 103 is provided between the conductive substrate 101 and the photosensitive layer 102. As shown in fig. 1(a), the photosensitive layer 102 may be directly provided on the conductive substrate 101. Alternatively, as shown in fig. 1(b), the photosensitive layer 102 may be provided on the conductive substrate 101 via the intermediate layer 103. The intermediate layer 103 may be one layer or several layers.
As shown in fig. 1(c), the photoreceptor 100 may include a conductive substrate 101, a photosensitive layer 102, and a protective layer 104. The passivation layer 104 is disposed on the photosensitive layer 102. The protection layer 104 may be one layer or several layers.
The thickness of the photosensitive layer 102 is not particularly limited as long as the photosensitive layer 102 can sufficiently function as the photosensitive layer 102. The thickness of the photosensitive layer 102 is preferably 5 μm to 100 μm, and more preferably 10 μm to 50 μm.
The structure of the photoreceptor 100 is described above with reference to fig. 1. The photoreceptor will be described in further detail below.
< photosensitive layer >
The photosensitive layer contains at least a charge generator and a compound represented by the general formula (1). The photosensitive layer may further contain a hole transporting agent. The photosensitive layer may further contain a binder resin. The photosensitive layer may contain additives as needed.
(Compound (1))
The photosensitive layer contains a compound represented by general formula (1) (hereinafter, sometimes referred to as compound (1)). The photosensitive layer contains, for example, the compound (1) as an electron transporting agent.
[ CHEM 3 ]
In the general formula (1), R1Represents nitro, C1-C8 alkyl, C6-C14 aryl which may have C1-C8 alkyl, C7-C20 aralkyl, C3-C10 cycloalkyl or C1-C6 alkoxy. R2、R3、R4And R5Each independently represents a hydrogen atom, a nitro group, a C1-C8 alkyl group, a C6-C14 aryl group which may have a C1-C8 alkyl group, a C7-C20 aralkyl group, a C3-C10 cycloalkyl group or a C1-C6 alkoxy group. m represents an integer of 0 to 5 inclusive. When m represents an integer of 2 to 5, a plurality of R1May be the same or different.
The photosensitive layer contains the compound (1), and thus the sensitivity characteristics of the photoreceptor can be improved. The reason is presumed as follows.
First, the compound (1) has a cyano group and a carbonyl group. Both cyano and carbonyl groups are electron accepting groups. However, the electron acceptance of the cyano group is lower than that of the carbonyl group (═ CO). When 2 electron-accepting groups (for example, 2 carbonyl groups) are present in the compound at asymmetric positions, the electron-accepting property of the compound becomes too high, and the compound may continue to hold electrons even after accepting electrons. However, the compound (1) has a carbonyl group and a cyano group having a lower electron-accepting property than the carbonyl group. Therefore, even when 2 electron-accepting groups (specifically, a carbonyl group and a cyano group) are present in an asymmetric position in the compound (1), the electron-accepting property of the compound (1) does not become excessively high. Thus, after one compound (1) accepts electrons, the electrons are well transported from the one compound (1) to the other compounds (1) in the vicinity. As a result, the sensitivity characteristics of the photoreceptor are improved.
Second, a cyclohexyl ring is present in the four-ring fused ring of the compound (1). The presence of a cyclohexyl ring improves the lipid solubility of compound (1). This improves the compatibility of the compound (1) with the binder resin. Thus, a uniform photosensitive layer can be formed, and the sensitivity characteristics of the photoreceptor can be improved. In addition, crystallization of the photosensitive layer of the photoreceptor can be suppressed.
Third, the four ring fused rings in compound (1) have an asymmetric structure. The compound (1) has a tetracyclic condensed ring having an asymmetric structure, and the solubility of the compound (1) in a photosensitive layer-forming solvent is improved. In addition, the compound (1) has four ring condensed rings with asymmetric structures, and the compatibility of the compound (1) relative to the binding resin is improved. The improvement of solubility and compatibility enables formation of a uniform photosensitive layer and improves the sensitivity characteristics of the photoreceptor. In addition, crystallization of the photosensitive layer of the photoreceptor can be suppressed.
Fourth, having R1The phenyl group of (2) is bonded to one carbon atom constituting a tetracyclic fused ring in the compound (1). Having R1The angle of attachment of the phenyl group of (a) to the tetracyclic fused ring is large. Having R1The presence of phenyl groups of (a) is such that the tetracyclic fused rings of one compound (1) do not overlap too closely with the tetracyclic fused rings of the other compound (1). This can appropriately maintain the interval between the compounds (1) and improve the solubility of the compound (1) in the photosensitive layer forming solvent. Thus, a uniform photosensitive layer can be formed, and the sensitivity characteristics of the photoreceptor can be improved. Further, crystallization of the photosensitive layer of the photoreceptor can be suppressed. The reason why the sensitivity characteristics of the photoreceptor are improved is described above. The compound (1) will be described below.
R in the general formula (1)1～R5The C1-C8 alkyl group represented is preferably a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably a methyl group.
R in the general formula (1)1～R5The C6-C14 aryl group represented is preferably a C6-C10 aryl group. R1～R5The C6-C14 aryl groups represented may have C1-C8 alkyl groups.
R in the general formula (1)1～R5The C7-C20 aralkyl group represented is preferably a C1-C6 alkyl group having a phenyl group or a C1-C6 alkyl group having a naphthyl group.
R in the general formula (1)1～R5The C3-C10 cycloalkyl radicals represented are preferably C5-C7 cycloalkyl radicals.
R in the general formula (1)1～R5The C1-C6 alkoxy group is preferablyIs selected from C1-C3 alkoxy.
M in the general formula (1) preferably represents 0 or 1.
In the general formula (1), R is preferably represented by formula (1) in order to improve the sensitivity characteristics of the photoreceptor1Represents nitro or C1-C8 alkyl, R2、R3、R4And R5Each independently represents a hydrogen atom or a C1-C8 alkyl group. In the general formula (1), more preferably, R1Represents nitro or C1-C8 alkyl, R2、R3、R4And R5Each independently represents a hydrogen atom or a C1-C8 alkyl group, and m represents 0 or 1.
In the general formula (1), R is preferably used for further improving the sensitivity characteristics of the photoreceptor1Represents a nitro group. Similarly, in the general formula (1), more preferably, R1Represents nitro, R2、R3、R4And R5Each independently represents a hydrogen atom or a C1-C8 alkyl group. Similarly, in the general formula (1), it is further preferable that R1Represents nitro, R2、R3、R4And R5Each independently represents a hydrogen atom or a C1-C8 alkyl group, and m represents 0 or 1. Preferred examples of such a compound (1) include compounds represented by the chemical formulae (1-3) and (1-5) (hereinafter, sometimes referred to as compounds (1-3) and (1-5), respectively).
[ CHEM 4 ]
In the general formula (1), R is preferably represented by formula (1) in order to further improve the sensitivity characteristics of the photoreceptor4And R5Each represents a C1-C8 alkyl group, and m represents 0. Similarly, in the general formula (1), more preferably, R1Represents nitro or C1-C8 alkyl, R2And R3Each independently represents a hydrogen atom or a C1-C8 alkyl group, R4And R5Each represents a C1-C8 alkyl group, and m represents 0. Preferred examples of such a compound (1) include compounds represented by the formula (1-1) (hereinafter, sometimes referred to as compound (1-1)).
[ CHEM 5 ]
Preferred examples of the compound (1) include, in addition to the compounds (1-1), (1-3) and (1-5), compounds represented by the chemical formulae (1-2) and (1-4) (hereinafter, sometimes referred to as the compounds (1-2) and (1-4), respectively).
[ CHEM 6 ]
The photosensitive layer may contain only the compound (1) as an electron transporting agent. The photosensitive layer may contain an electron-transporting agent other than the compound (1) (hereinafter, sometimes referred to as another electron-transporting agent) in addition to the compound (1). Examples of other electron transport agents are: quinone compounds, imide compounds, hydrazone compounds, thiopyran compounds, trinitrothioxanthone compounds, 3, 4, 5, 7-tetranitro-9-fluorenone compounds, dinitroanthracene compounds, dinitroacridine compounds, tetracyanoethylene, 2, 4, 8-trinitrothioxanthone, dinitrobenzene, dinitroacridine, succinic anhydride, maleic anhydride and dibromomaleic anhydride. Quinone compounds such as: a diphenoquinone compound, an azoquinone compound, an anthraquinone compound, a naphthoquinone compound, a nitroanthraquinone compound, and a dinitroanthraquinone compound.
One compound (1) may be used alone, or two or more compounds may be used in combination. The other electron-transporting agents may be used alone or in combination of two or more. The content of the compound (1) is preferably 80% by mass or more, more preferably 90% by mass or more, and particularly preferably 100% by mass, relative to the total mass of the electron transporting agent.
The content of the compound (1) is preferably 5 parts by mass or more and 100 parts by mass or less, and more preferably 20 parts by mass or more and 40 parts by mass or less, with respect to 100 parts by mass of the binder resin. When the content of the compound (1) is 5 parts by mass or more per 100 parts by mass of the binder resin, the sensitivity characteristics of the photoreceptor can be easily improved. When the content of the compound (1) is 100 parts by mass or less based on 100 parts by mass of the binder resin, the compound (1) is easily dissolved in a solvent for forming a photosensitive layer, and a uniform photosensitive layer can be easily formed.
Next, a method for producing the compound (1) will be described. The compound (1) can be produced, for example, by a reaction represented by the following reaction formula (R-1) (hereinafter, may be referred to as reaction (R-1)) or a method similar thereto. The method for producing the compound (1) may further comprise an appropriate step as required in addition to the reaction (R-1). Hereinafter, the compounds represented by the general formulae (A), (B) and (C) shown in the reaction (R-1) are respectively described as compounds (A), (B) and (C). R in the general formulae (A), (B) and (C)1、R2、R3、R4、R5And each m is independently R in the formula (1)1、R2、R3、R4、R5And m has the same meaning.
[ CHEM 7 ]
In the reaction (R-1), 1 molar equivalent of the compound (a), 1 molar equivalent of the compound (B), and 1 molar equivalent of the compound (C) are reacted to obtain 1 molar equivalent of the compound (1). Specifically, 1 molar equivalent of the compound (a) and 1 molar equivalent of the compound (B) are subjected to the first stirring in the solvent. Examples of the solvent include water, C1-C4 alcohol and a mixed solvent thereof. The solvent is preferably a mixed solvent of ethanol and water. The reaction temperature in the first stirring is preferably 50 ℃ to 100 ℃. The time of the first stirring is preferably 0.5 hours or more and 5 hours or less.
Next, compound (C) and a strong base are added to the solution subjected to the first stirring in an amount of 1 molar equivalent, and the second stirring is performed. Examples of strong bases are potassium tert-butoxide, sodium tert-butoxide and sodium methoxide. The reaction temperature during the second stirring is preferably 50 ℃ to 100 ℃. The time of the second stirring is preferably 1 hour to 5 hours.
Next, an acid is added to the solution subjected to the second stirring, and a third stirring is performed. Examples of acids are hydrochloric acid. The reaction temperature during the third stirring is preferably 50 ℃ to 100 ℃. The time of the third stirring is preferably 1 hour to 5 hours.
After the reaction (R-1) is carried out, the obtained compound (1) can be purified. The purification method is, for example, a known method (for example, filtration, silica gel column chromatography or crystallization).
(Charge generating agent)
The charge generating agent is not particularly limited as long as it is a charge generating agent for a photoreceptor. Charge generators such as phthalocyanine pigments, perylene pigments, disazo pigments, trisazo pigments, dithione pyrrolopyrrole (dithioketo-pyrrolole) pigments, metal-free naphthalocyanine pigments, metal naphthalocyanine pigments, squaric acid pigments, indigo pigments, azulene pigments, cyanine pigments, powders of inorganic photoconductive materials (e.g., selenium-tellurium, selenium-arsenic, cadmium sulfide or amorphous silicon), pyran pigments, anthanthrone pigments, triphenylmethane pigments, threne pigments, toluidine pigments, pyrazoline pigments and quinacridone pigments. The charge generating agent may be used alone or in combination of two or more.
Examples of the phthalocyanine pigments include metal-free phthalocyanine and metal phthalocyanine. The metal-free phthalocyanine is represented by, for example, the chemical formula (CGM 2). Metal phthalocyanines such as: oxytitanium phthalocyanine, hydroxygallium phthalocyanine and chlorogallium phthalocyanine. The oxytitanium phthalocyanine is represented by the chemical formula (CGM 1). The phthalocyanine pigment may be crystalline or amorphous. The crystal shape (for example, α -type, β -type, Y-type, V-type, or II-type) of the phthalocyanine pigment is not particularly limited, and phthalocyanine pigments having various crystal shapes can be used.
[ CHEM 8 ]
[ CHEM 9 ]
Examples of metal phthalocyanine-free crystals are: an X-type crystal of metal-free phthalocyanine (hereinafter, sometimes referred to as X-type metal-free phthalocyanine). The crystal of oxytitanium phthalocyanine includes, for example, α -type, β -type and Y-type crystals of oxytitanium phthalocyanine (hereinafter, sometimes referred to as α -type, β -type and Y-type oxytitanium phthalocyanine).
For example, in a digital optical image forming apparatus (for example, a laser printer or a facsimile machine using a light source such as a semiconductor laser), a photoreceptor having sensitivity in a wavelength region of 700nm or more is preferably used. The charge generating agent is preferably a phthalocyanine-based pigment, more preferably a metal-free phthalocyanine or oxytitanium phthalocyanine, still more preferably an X-type metal-free phthalocyanine or Y-type oxytitanium phthalocyanine, and particularly preferably a Y-type oxytitanium phthalocyanine, from the viewpoint of having a high quantum yield in a wavelength region of 700nm or more.
For example, Y-type oxytitanium phthalocyanine has a main peak at 27.2 ° of the bragg angle (2 θ ± 0.2 °) in the CuK α characteristic X-ray diffraction spectrum. The main peak in the CuK α characteristic X-ray diffraction spectrum means a peak having a first or second large intensity in a range where the bragg angle (2 θ ± 0.2 °) is 3 ° or more and 40 ° or less.
An example of a method for measuring CuK α characteristic X-ray diffraction spectrum will be described. A sample (oxytitanium phthalocyanine) was filled in a sample holder of an X-ray diffraction apparatus (for example, "RINT (Japanese registered trademark) 1100" manufactured by Rigaku Corporation), and X-ray wavelengths characterized by an X-ray tube Cu, a tube voltage of 40kV, a tube current of 30mA and CuK. alpha. were measured
Under the conditions of (1), an X-ray diffraction spectrum was measured. For example, the measurement range (2 θ) is 3 ° to 40 ° (start angle: 3 °; stop angle: 40 °), and the scanning speed is 10 °/min.
In the photoreceptor used in an image forming apparatus using a short-wavelength laser light source (for example, a laser light source having a wavelength of about 350nm to 550 nm), an anthraquinone-based pigment is preferably used as the charge generating agent.
The content of the charge generating agent is preferably 0.1 part by mass or more and 50 parts by mass or less, more preferably 0.5 part by mass or more and 30 parts by mass or less, and particularly preferably 0.5 part by mass or more and 4.5 parts by mass or less, with respect to 100 parts by mass of the binder resin contained in the photosensitive layer.
(hole transport agent)
Hole-transporting agents such as: triphenylamine derivatives, diamine derivatives (e.g., N ' -tetraphenylbenzidine derivatives, N ' -tetraphenylphenylenediamine derivatives, N ' -tetraphenylnaphthalenediamine derivatives, N ' -tetraphenylphenylenediamine (N, N ' -tetraphenylphenylenediamine) derivatives or bis (aminophenylvinyl) benzene derivatives), oxadiazole compounds (e.g., 2, 5-bis (4-methylaminophenyl) -1, 3, 4-oxadiazole), styrenic compounds (e.g., 9- (4-diethylaminostyryl) anthracene), carbazole compounds (e.g., polyvinylcarbazole), organic polysilane compounds, pyrazoline compounds (e.g., 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline), hydrazone compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds and triazole compounds. The hole-transporting agent may be used alone or in combination of two or more.
The photosensitive layer preferably contains a compound represented by general formula (10) (hereinafter, sometimes referred to as compound (10)). The photosensitive layer preferably contains the compound (10) as a hole transporting agent, for example.
[ CHEM 10 ]
In the general formula (10), R101、R102、R103、R104、R105And R106Independently of one another, represents a C1-C6 alkyl group, a C1-C6 alkoxy group or a C6-C14 aryl group. a. b, c and d are each independently an integer of 0 to 5. e and f are each independently an integer of 0 to 4.
a is an integer of 2 to 5 or lessR is101May be the same or different. b represents an integer of 2 to 5 inclusive, and R's are several102May be the same or different. c represents an integer of 2 to 5 inclusive, and R's are several103May be the same or different. d is an integer of 2 to 5 inclusive, and R is several104May be the same or different. e represents an integer of 2 to 4, and R' s105May be the same or different. f is an integer of 2 to 4, and R is a number of106May be the same or different.
In the general formula (10), R101、R102、R103、R104、R105And R106Each independently preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group. a. b, c and d are each independently preferably 0 or 1, more preferably 1. e and f are each independently preferably 0 or 1, more preferably 1.
Preferable examples of the compound (10) include a compound represented by the following chemical formula (10-1) (hereinafter, may be referred to as the compound (10-1)).
[ CHEM 11 ]
The photosensitive layer may contain only the compound (10) as a hole transporting agent. The content of the compound (10) is preferably 80% by mass or more, more preferably 90% by mass or more, and particularly preferably 100% by mass, relative to the mass of the hole-transporting agent.
The content of the hole transporting agent contained in the photosensitive layer is preferably 10 parts by mass or more and 200 parts by mass or less, and more preferably 10 parts by mass or more and 100 parts by mass or less, with respect to 100 parts by mass of the binder resin.
(Binder resin)
The binder resin is, for example: thermoplastic resins, thermosetting resins, and photocurable resins. Thermoplastic resins such as: polycarbonate resins, polyarylate resins, styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, acrylic polymers, styrene-acrylic acid copolymers, polyethylene resins, ethylene-vinyl acetate copolymers, chlorinated polyethylene resins, polyvinyl chloride resins, polypropylene resins, ionomer resins, vinyl chloride-vinyl acetate copolymers, alkyd resins, polyamide resins, polyurethane resins, polysulfone resins, diallyl phthalate resins, ketone resins, polyvinyl butyral resins, polyester resins, and polyether resins. Thermosetting resins such as: silicone resins, epoxy resins, phenol resins, urea resins, and melamine resins. The photocurable resin is, for example: acrylic acid adducts of epoxy compounds and acrylic acid adducts of urethane compounds. These binder resins may be used alone or in combination of two or more.
Among these resins, polycarbonate resins are preferred in view of obtaining a photosensitive layer having a relatively excellent balance among processability, mechanical properties, optical properties and abrasion resistance. Examples of the polycarbonate resin are: bisphenol ZC type polycarbonate resin, bisphenol C type polycarbonate resin, bisphenol a type polycarbonate resin, and bisphenol Z type polycarbonate resin. The bisphenol Z-type polycarbonate resin is a polycarbonate resin having a repeating unit represented by the following chemical formula (20). Hereinafter, a polycarbonate resin having a repeating unit represented by chemical formula (20) may be referred to as a polycarbonate resin (20).
[ CHEM 12 ]
(additives)
Additives such as: degradation inhibitors (e.g., antioxidants, radical scavengers, singlet quenchers, or ultraviolet absorbers), softening agents, surface modifiers, extenders, thickeners, dispersion stabilizers, waxes, acceptors, donors, surfactants, plasticizers, sensitizers, and leveling agents. Antioxidants such as: hindered phenols (e.g., di (t-butyl) p-cresol, hindered amines, p-phenylenediamine, arylalkanes, hydroquinones, spirochromans (spirochromans), spiroindanones (spiroindanones) or derivatives thereof, organic sulfur compounds and organic phosphorus compounds.
< conductive substrate >
The conductive substrate is not particularly limited as long as it can be used as a conductive substrate of a photoreceptor. The conductive substrate may be formed of a conductive material at least on the surface portion. The conductive substrate may be, for example, a conductive substrate formed of a conductive material. The conductive substrate may be a conductive substrate coated with a conductive material, for example. Conductive materials such as: aluminum, iron, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, and brass. These conductive materials may be used alone, or two or more of them may be used in combination (for example, as an alloy). Among these conductive materials, aluminum or an aluminum alloy is preferable in terms of good charge transfer from the photosensitive layer to the conductive substrate.
The shape of the conductive substrate is appropriately selected according to the structure of the image forming apparatus. The shape of the conductive substrate is, for example, a sheet shape or a drum shape. The thickness of the conductive substrate is appropriately selected according to the shape of the conductive substrate.
< intermediate layer >
The intermediate layer (undercoat layer) contains, for example, inorganic particles and a resin (resin for intermediate layer) for the intermediate layer. It can be considered that: since the intermediate layer is present, the current generated when the photoreceptor is exposed can be smoothly flowed while maintaining an insulating state to such an extent that the occurrence of electric leakage can be suppressed, thereby suppressing an increase in resistance.
Inorganic particles such as: particles of a metal (e.g., aluminum, iron, or copper), a metal oxide (e.g., titanium dioxide, aluminum oxide, zirconium oxide, tin oxide, or zinc oxide), and particles of a non-metal oxide (e.g., silicon dioxide). These inorganic particles may be used alone or in combination of two or more.
The resin for the intermediate layer is not particularly limited as long as it can be used as a resin for forming the intermediate layer. The intermediate layer may also contain additives. Examples of the additive contained in the intermediate layer are the same as those of the additive contained in the photosensitive layer.
< method for producing photoreceptor >
The photoreceptor is manufactured, for example, as follows. The photoreceptor is produced by applying a coating liquid for a photosensitive layer on a conductive substrate and drying the coating liquid. The coating liquid for photosensitive layers is produced by dissolving or dispersing a charge generating agent, an electron transporting agent, and components added as needed (for example, a hole transporting agent, a binder resin, and additives) in a solvent.
The solvent contained in the coating liquid for photosensitive layer is not particularly limited as long as it can dissolve or disperse each component contained in the coating liquid. Examples of solvents are: alcohols (e.g., methanol, ethanol, isopropanol, or butanol), aliphatic hydrocarbons (e.g., n-hexane, octane, or cyclohexane), aromatic hydrocarbons (e.g., benzene, toluene, or xylene), halogenated hydrocarbons (e.g., dichloromethane, dichloroethane, carbon tetrachloride, or chlorobenzene), ethers (e.g., dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, or propylene glycol monomethyl ether), ketones (e.g., acetone, methyl ethyl ketone, or cyclohexanone), esters (e.g., ethyl acetate or methyl acetate), dimethyl formaldehyde, dimethyl formamide, and dimethyl sulfoxide. These solvents may be used alone or in combination of two or more. In order to improve the workability in the production of the photoreceptor, it is preferable to use a halogen-free solvent (a solvent other than halogenated hydrocarbon) as the solvent.
The components are mixed and dispersed in a solvent to prepare a coating liquid. For the mixing or dispersing, for example, a bead mill, roll mill, ball mill, attritor, paint shaker or ultrasonic disperser can be used.
In order to improve the dispersibility of each component, for example, a surfactant may be contained in the coating liquid for photosensitive layer.
The method for applying the coating liquid for the photosensitive layer is not particularly limited as long as the coating liquid can be uniformly applied to the conductive substrate. The coating method includes, for example: a blade coating method, a dip coating method, a spray coating method, a spin coating method, and a bar coating method.
The method for drying the coating liquid for photosensitive layer is not particularly limited as long as the solvent in the coating liquid can be evaporated. For example, one method is heat treatment (hot air drying) using a high-temperature dryer or a reduced-pressure dryer. The heat treatment conditions are, for example, a temperature of 40 ℃ to 150 ℃ and a time of 3 minutes to 120 minutes.
The method for manufacturing the photoreceptor may further include one or both of the step of forming the intermediate layer and the step of forming the protective layer, as necessary. The step of forming the intermediate layer and the step of forming the protective layer can be realized by appropriately selecting a known method.
[ examples ] A method for producing a compound
The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the scope of the examples.
< Material for Forming photosensitive layer >
As materials for forming the photosensitive layer of the photoreceptor, the following charge generating agent, hole transporting agent, binder resin, and electron transporting agent were prepared.
(Charge generating agent)
Y-type oxytitanium phthalocyanine and X-type metal-free phthalocyanine are prepared as charge generators. The Y-type oxytitanium phthalocyanine has a Y-type crystal structure represented by the chemical formula (CGM1) described in the embodiments. The X-type metal-free phthalocyanine is an X-type crystal structure metal-free phthalocyanine represented by the chemical formula (CGM2) described in the embodiments.
(hole transport agent)
The compound (10-1) described in the embodiment was prepared as a hole transporting agent.
(Binder resin)
Bisphenol Z type polycarbonate resin was prepared as a binder resin. The bisphenol Z-type polycarbonate resin is a polycarbonate resin having a repeating unit represented by chemical formula (20) described in the embodiments. The viscosity average molecular weight of the bisphenol Z polycarbonate resin was 50000.
(Electron transport agent)
The compounds (1-1) to (1-5) described in the embodiment were prepared as an electron-transporting agent. The compounds (1-1) to (1-5) were synthesized by the following methods.
(Synthesis of Compound (1-1))
Compound (1-1) is synthesized according to the reaction represented by reaction formula (r-1) (hereinafter, referred to as reaction (r-1)). The compounds represented by the following chemical formulas (A-1), (A-2), (B-1), (B-2) and (C-1) to (C-4) are respectively described as compounds (A-1), (A-2), (B-1), (B-2) and (C-1) to (C-4). The yield of each compound was determined in terms of a molar ratio.
[ CHEM 13 ]
In the reaction (r-1), the compound (A-1), the compound (B-1) and the compound (C-1) are reacted to obtain the compound (1-1). Specifically, compound (A-1) (0.108g, 1mmol) and compound (B-1) (0.140g, 1mmol) were added to a mixture of ethanol (2mL) and water (2mL) to obtain a solution. The solution was stirred at 70 ℃ for 1 hour. To the stirred solution after 1 hour, compound (C-1) (0.154g, 1mmol) and potassium tert-butoxide (0.011g, 0.1mmol) were added, and the mixture was stirred at 70 ℃ for another 3 hours. Hydrochloric acid (concentration: 37%, 1mmol) was added to the stirred solution after 3 hours, and further stirred at 70 ℃ for 3 hours. Then, the solution was cooled until the temperature of the solution reached room temperature, and a solid was precipitated. The precipitated solid was filtered to obtain a residue. The residue was washed with a mixed solution of ethanol and water (volume ratio: ethanol/water: 1/1) to obtain compound (1-1). The yield of the compound (1-1) was 0.310 g. The yield of the compound (1-1) from the compound (A-1) was 85%.
(Synthesis of Compounds (1-2) to (1-5))
Compounds (1-2) to (1-5) were synthesized by the same method as that for the synthesis of compound (1-1), except for the following changes. While 0.108g (1mmol) of compound (A-1) was added in the synthesis of compound (1-1), compounds (1-2) to (1-5) were added in the amounts and kinds shown in the column of compound (A) in Table 1. While 0.140g (1mmol) of compound (B-1) was added in the synthesis of compound (1-1), compounds (1-2) to (1-5) were added in amounts and kinds shown in the column of compound (B) in Table 1. While 0.154g (1mmol) of compound (C-1) was added in the synthesis of compound (1-1), compounds (1-2) to (1-5) were added in amounts and kinds shown in the column of compound (C) in Table 1. As a result, a reaction product (one of the compounds (1-2) to (1-5)) of the kind shown in Table 1 was obtained in place of the compound (1-1). Table 1 shows the respective yields of the compounds (1-1) to (1-5). Further, Table 1 shows the yields of the compounds (1-1) to (1-5) from the compounds shown in the column of the compound (A), respectively.
[ TABLE 1 ]
[ CHEM 14 ]
Then, by1H-NMR (proton Nuclear magnetic resonance Spectroscopy) for measuring Compounds (1-1) to (1-5)1H-NMR spectrum. The magnetic field strength was set at 300 MHz. Deuterated DMSO (DMSO-d)6) Is used as a solvent. Tetramethylsilane (TMS) was used as an internal standard. Compound (1-1) As representative examples of the compounds (1-1) to (1-5), Compound (1-1)1The chemical shift values of the H-NMR spectrum are shown below. According to the measured1Chemical shift values in the H-NMR spectrum confirmed that the compound (1-1) was obtained. The compounds (1-2) to (1-5) were also measured1The chemical shift values in the H-NMR spectrum confirmed that the compounds (1-2) to (1-5) were obtained, respectively.
Compound (1-1):1H-NMR(300MHz，DMSO-d6)δ＝1.21(s，6H)、2.53(s，2H)、3.77(s，2H)、7.10-7.35(m，2H)、7.40-7.49(m，3H)、7.52(t，1H)、7.67(t，1H)、7.98(d，1H)、8.45(d，1H)。
a compound represented by the following chemical formula (E-1) (hereinafter referred to as compound (E-1)) was also prepared as an electron transporting agent used in the comparative examples.
[ CHEM 15 ]
< production of photoreceptor >
The photoreceptors (A-1) to (A-10) and (B-1) to (B-2) were produced using the materials for forming the photosensitive layer.
(production of photoreceptor (A-1))
Charging into a container: 2 parts by mass of X-type metal-free phthalocyanine as a charge generator, 50 parts by mass of a compound (10-1) as a hole transporting agent, 30 parts by mass of a compound (1-1) as an electron transporting agent, 100 parts by mass of a bisphenol Z-type polycarbonate resin as a binder resin, and 600 parts by mass of tetrahydrofuran as a solvent. The contents of the vessel were mixed for 12 hours using a ball mill to disperse the material in the solvent. Thus, a coating liquid for photosensitive layer was obtained. The coating liquid for photosensitive layer was applied to a conductive substrate (aluminum drum support, diameter 30mm, total length 238.5mm) by a blade coating method. The coating liquid for photosensitive layer applied was dried with hot air at 120 ℃ for 80 minutes. Thereby, a single photosensitive layer (film thickness 30 μm) was formed on the conductive substrate. Thus, photoreceptor (A-1) was obtained.
(production of photoreceptors (A-2) to (A-10) and (B-1) to (B-2))
Photoreceptors (A-2) to (A-10) and (B-1) to (B-2) were produced by the same method as for the photoreceptor (A-1) except for the following changes. In the production of the photoreceptor (A-1), X-type metal-free phthalocyanine was used as the charge generating agent, and the types of charge generating agents shown in Table 2 were used in the production of the photoreceptors (A-2) to (A-10) and (B-1) to (B-2), respectively. In the production of the photoreceptor (A-1), the compound (1-1) was used as the electron-transporting agent, and in the production of each of the photoreceptors (A-2) to (A-10) and (B-1) to (B-2), the electron-transporting agents of the types shown in Table 2 were used.
< evaluation of sensitivity characteristics >
Sensitivity characteristics were evaluated for each of the photoreceptors (A-1) to (A-10) and (B-1) to (B-2). The sensitivity characteristics were evaluated at 23 ℃ and 50% RH relative humidity. First, the surface of the photoreceptor was charged to +600V using a drum sensitivity tester (manufactured by GENTEC corporation). Then, monochromatic light (wavelength 780nm, half-width 20nm, light energy 1.5. mu.J/cm) was extracted from the white light of the halogen lamp using a band-pass filter2). The extracted monochromatic light is irradiated to the surface of the photoreceptor. The surface potential of the photoreceptor after 50 milliseconds from the end of the irradiation was measured. The measured surface potential was taken as the post-exposure potential (V)L(ii) a Unit: + V). Measured potential (V) after exposure of the photoreceptorL) As shown in table 2. And, post-exposure potential (V)L) The smaller positive value indicates that the photoreceptor is more excellent in sensitivity characteristics (particularly, photosensitivity characteristics).
< evaluation of Presence of crystallization >
The entire surface (photosensitive layer) area of each of the photoreceptors (A-1) to (A-10) and (B-1) to (B-2) was observed with the naked eye. Then, the presence or absence of crystallized portions in the photosensitive layer was confirmed. The results of the confirmation are shown in Table 2.
In Table 2, CGM, HTM, ETM, VL、X-H2Pc and Y-TiOPc represent a charge generating agent, a hole transporting agent, an electron transporting agent, a post-exposure potential, X-type metal-free phthalocyanine and Y-type oxytitanium phthalocyanine, respectively. In table 2, "none" indicates a portion in the photosensitive layer where no crystallization was observed, and "little crystallization" indicates a portion in the photosensitive layer where little crystallization was observed.
[ TABLE 2 ]
The photoreceptors (A-1) to (A-10) are provided with a conductive substrate and a single photosensitive layer. The photosensitive layer contains at least a charge generating agent and a compound (1). Specifically, the photosensitive layer contains one of the compounds (1-1) to (1-5) contained in the general formula (1). Therefore, as can be seen from Table 2, the photoreceptors (A-1) to (A-10) had a small positive post-exposure potential and exhibited excellent sensitivity characteristics. In the photoreceptors (a-1) to (a-10), no crystallization was observed in the photosensitive layer, and the crystallization of the photosensitive layer was suppressed.
On the other hand, the photosensitive layers of the photoreceptors (B-1) to (B-2) do not contain the compound (1). Specifically, although the photosensitive layers of the photoreceptors (B-1) to (B-2) contain the compound (E-1), the compound (E-1) is not a compound contained in the general formula (1). Therefore, as can be seen from Table 2, the photoreceptors (B-1) to (B-2) had a large positive post-exposure potential, and the photoreceptors had poor sensitivity characteristics. In the photoreceptors (B-1) to (B-2), some crystallization was observed in the photosensitive layer, and thus the crystallization of the photosensitive layer could not be suppressed.
As described above, the photoreceptor according to the present invention is excellent in sensitivity characteristics.
Claims (10)
1. An electrophotographic photoreceptor is provided with a photosensitive layer containing a photosensitive compound,
comprises a conductive substrate and a single photosensitive layer,
the photosensitive layer contains at least a charge generating agent and a compound represented by the following general formula (1),
[ CHEM 1 ]
In the general formula (1) described above,
R1represents nitro, C1-C8 alkyl, C6-C14 aryl which may have C1-C8 alkyl, C7-C20 aralkyl, C3-C10 cycloalkyl or C1-C6 alkoxy,
R2、R3、R4and R5Independently of one another, represents a hydrogen atom, a nitro group, a C1-C8 alkyl group, a C6-C14 aryl group which may have a C1-C8 alkyl group, a C7-C20 aralkyl group, a C3-C10 cycloalkyl group or a C1-C6 alkoxy group,
m represents an integer of 0 to 5 inclusive, and when m represents an integer of 2 to 5 inclusive, a plurality of R1May be the same or different.
2. The electrophotographic photoreceptor according to claim 1,
in the general formula (1), R1Represents nitro or C1-C8 alkyl, R2、R3、R4And R5Each independently represents a hydrogen atom or a C1-C8 alkyl group.
3. The electrophotographic photoreceptor according to claim 2,
m represents 0 or 1.
4. The electrophotographic photoreceptor according to claim 3,
in the general formula (1), R1Represents a nitro group.
5. The electrophotographic photoreceptor according to claim 4,
the compound represented by the general formula (1) is a compound represented by the following chemical formula (1-3) or (1-5),
[ CHEM 2 ]
6. The electrophotographic photoreceptor according to claim 3,
in the general formula (1), R4And R5Both represent C1-C8 alkyl, and m represents 0.
7. The electrophotographic photoreceptor according to claim 6,
the compound represented by the general formula (1) is a compound represented by the following chemical formula (1-1),
[ CHEM 3 ]
8. The electrophotographic photoreceptor according to claim 3,
the compound represented by the general formula (1) is a compound represented by the following chemical formula (1-2) or (1-4),
[ CHEM 4 ]
9. The electrophotographic photoreceptor according to claim 1 or 2,
the photosensitive layer further contains a compound represented by the following general formula (10),
[ CHEM 5 ]
In the general formula (10), R101、R102、R103、R104、R105And R106Independently of one another, represents a C1-C6 alkyl group, a C1-C6 alkoxy group or a C6-C14 aryl group,
a. b, c and d are each independently an integer of 0 to 5 inclusive,
e and f are each independently an integer of 0 to 4.
10. The electrophotographic photoreceptor according to claim 1 or 2,
the photosensitive layer further contains a polycarbonate resin having a repeating unit represented by the following chemical formula (20),
[ CHEM 6 ]
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| JP2017043655A JP2018146873A (en) | 2017-03-08 | 2017-03-08 | Electrophotographic photoreceptor |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1171566A (en) * | 1996-06-21 | 1998-01-28 | 富士电机株式会社 | Electrophotographic photosensitive body |
| JPH10239878A (en) * | 1997-02-27 | 1998-09-11 | Ricoh Co Ltd | Electrophotographic photoreceptor |
| US5968697A (en) * | 1997-02-27 | 1999-10-19 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor |
| CN101030050A (en) * | 2006-03-03 | 2007-09-05 | 夏普株式会社 | Electrophotoconductor and image forming apparatus |
| CN102807496A (en) * | 2011-05-31 | 2012-12-05 | 京瓷办公信息系统株式会社 | Triarylamine derivative, electrophotographic photoconductor and image-forming apparatus |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1171566A (en) * | 1996-06-21 | 1998-01-28 | 富士电机株式会社 | Electrophotographic photosensitive body |
| JPH10239878A (en) * | 1997-02-27 | 1998-09-11 | Ricoh Co Ltd | Electrophotographic photoreceptor |
| US5968697A (en) * | 1997-02-27 | 1999-10-19 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor |
| CN101030050A (en) * | 2006-03-03 | 2007-09-05 | 夏普株式会社 | Electrophotoconductor and image forming apparatus |
| CN102807496A (en) * | 2011-05-31 | 2012-12-05 | 京瓷办公信息系统株式会社 | Triarylamine derivative, electrophotographic photoconductor and image-forming apparatus |
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