CN107643658A - Electrophtography photosensor - Google Patents
Electrophtography photosensor Download PDFInfo
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- CN107643658A CN107643658A CN201710564485.0A CN201710564485A CN107643658A CN 107643658 A CN107643658 A CN 107643658A CN 201710564485 A CN201710564485 A CN 201710564485A CN 107643658 A CN107643658 A CN 107643658A
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Abstract
The present invention provides a kind of Electrophtography photosensor.Electrophtography photosensor possesses conductive base and photosensitive layer.Photosensitive layer contains electric charge producing agent, cavity conveying agent, benzoquinone methyl compound derivative and binding resin.Benzoquinone methyl compound derivative is represented by formula (1).R in formula (1)1、R2、R3With m respectively with the R in specification1、R2、R3It is identical with m implications.【Change 1】
Description
Technical field
The present invention relates to a kind of Electrophtography photosensor.
Background technology
Electrophtography photosensor is used in the image processing system of electrofax mode.Electrophtography photosensor possesses photosensitive
Layer.Electrophtography photosensor for example has laminated electronic electrophotographic photoconductor and mono-layer electronic photographic photoreceptor.Laminated electronic
Photosensitive layer in electrophotographic photoconductor is charge generation layer and charge transport layer, and there is charge generation layer electric charge to produce function, electric charge
Transfer layer has electric charge transfer function.Photosensitive layer in mono-layer electronic photographic photoreceptor is single-layer type photosensitive layer, single-layer type sense
There is photosphere electric charge to produce function and electric charge transfer function.
In Electrophtography photosensor described in patent document 1, chemical combination of the photosensitive layer for example containing chemical formula (E-2) expression
Thing.
【Change 1】
(patent document)
Patent document 1：Japanese Unexamined Patent Publication 2005-173292 publications
The content of the invention
But, the sensitivity characteristic of the Electrophtography photosensor described in patent document 1 is insufficient.
The present invention be in view of above-mentioned problem and make, its object is to provide a kind of sensitivity excellent electronics photograph
Phase photoreceptor.
The Electrophtography photosensor of the present invention possesses conductive base and photosensitive layer.The photosensitive layer contains：Electric charge produces
Agent, cavity conveying agent, benzoquinone methyl compound derivative and binding resin.The benzoquinone methyl compound derivative is by formula (1) table
Show.
【Change 2】
In the formula (1), R1Represent：Formula (2), C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyls
Base, nitro, C2-C7 alkoxy carbonyl groups or halogen atom.R1The C1-C6 alkyl represented can also have C6-C14 aryl.R1
The C6-C14 aryl represented can also have the first substituent.R2And R3It is each independent, represent：C1-C6 alkyl, C1-C6 alkane
Epoxide, C6-C14 aryl, C1-C7 acyl groups or halogen atom.R2And R3The C1-C6 alkyl represented can also have C6-
C14 aryl.R2And R3The C6-C14 aryl represented can also have the second substituent.M represents less than more than 05 integer.
In the case where m represents less than more than 25 integer, several R1Each other can be with identical or different.
【Change 3】
In the formula (2), R4And R5It is each independent, represent：C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-
C7 acyl groups or halogen atom.R4And R5The C1-C6 alkyl represented can also have C6-C14 aryl.R4And R5Represent
The C6-C14 aryl can also have the 3rd substituent.First substituent, second substituent and the described 3rd take
It is each independent for base, represent：There can be the C1-C6 alkyl of C6-C14 aryl；Or C1-C6 alkoxies, C6-C14 aryl,
C1-C7 acyl groups or halogen atom.First substituent, second substituent and the described 3rd substitute the described of basis representation
C1-C6 alkyl can also have C6-C14 aryl.
(invention effect)
The sensitivity excellent of the Electrophtography photosensor of the present invention.
Brief description of the drawings
Fig. 1 (a), Fig. 1 (b) and Fig. 1 (c) are to represent the Electrophtography photosensor involved by embodiment of the present invention respectively
The schematic cross sectional views of one example.
Fig. 2 (a), Fig. 2 (b) and Fig. 2 (c) are to represent the Electrophtography photosensor involved by embodiment of the present invention respectively
The schematic cross sectional views of other examples.
Fig. 3 is the chart for representing benzoquinone methyl compound derivative (1-1) infrared absorption spectroscopy.
Fig. 4 is the chart for representing benzoquinone methyl compound derivative (1-4) infrared absorption spectroscopy.
Embodiment
Hereinafter, embodiments of the present invention are described in detail.The present invention is not defined in following reality in any way
Apply mode.The present invention is implemented again after can suitably being changed in the range of its purpose.It additionally, there are and suitably eliminate repetition
Illustrate the situation of part, but therefore do not limit the main idea of invention.
Hereinafter, it is referred to as the compound and its derivative plus " class " after compound name sometimes.Further, in chemical combination
Name be referred to as after plus " class " come in the case of representing polymer name, represent the repeat unit of polymer be derived from the compound or
Its derivative of person.
Hereinafter, C1-C6 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C6 alkoxies, C1-C7 acyl groups, C2-C7 alcoxyl carbonyls
In the case of no special provision, respective implication is as follows for base, C2-C4 alkoxy carbonyl groups, C6-C14 aryl and halogen atom.
C1-C6 alkyl is straight-chain or branched, and is unsubstituted.C1-C6 alkyl for example has：Methyl, ethyl,
N-propyl, isopropyl, normal-butyl, sec-butyl, the tert-butyl group, amyl group, isopentyl, neopentyl or n-hexyl.
C1-C4 alkyl is straight-chain or branched, and is unsubstituted.C1-C4 alkyl for example has：Methyl, ethyl,
N-propyl, isopropyl, normal-butyl, sec-butyl or the tert-butyl group.
C1-C3 alkyl is straight-chain or branched, and is unsubstituted.C1-C3 alkyl for example has：Methyl, ethyl,
N-propyl or isopropyl.
C1-C6 alkoxies are straight-chain or branched, and are unsubstituted.C1-C6 Alkoxies if any：Methoxy
Base, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amoxy or hexyloxy.
C1-C7 acyl groups are straight-chain or branched, and are unsubstituted.C1-C7 acyl groups for example have：Formoxyl, first
Base carbonyl (acetyl group), ethylcarbonyl group, n-propyl carbonyl, Isopropylcarbonyl, n-butylcarbonyl, sec-butylcarbonyl group, tert-butyl group carbonyl
Base, pentylcarbonyl, i, neopentyl carbonyl or n-hexylcarbonyl.
C2-C7 alkoxy carbonyl groups are straight-chain or branched, and are unsubstituted.C2-C7 alkoxy carbonyl groups for example have：First
Oxygen carbonyl, carbethoxyl group, positive propylene carbonyl oxygen, butyloxycarbonyl, positive butoxy carbonyl, secondary butoxy carbonyl, tertbutyloxycarbonyl, amoxy
Carbonyl or hexyloxy carbonyl.
C2-C4 alkoxy carbonyl groups are straight-chain or branched, and are unsubstituted.C2-C4 alkoxy carbonyl groups for example have：First
Oxygen carbonyl, carbethoxyl group, positive propylene carbonyl oxygen or butyloxycarbonyl.
C6-C14 aryl is unsubstituted.C6-C14 aryl is, for example,：The unsubstituted aromatic monocyclic alkyl of C6-C14, C6-
The bicyclic alkyl of the unsubstituted aromatic condensations of C14 or the unsubstituted aromatic condensation tricyctic hydrocarbon bases of C6-C14.C6-C14 aryl is for example
Have：Phenyl, naphthyl, anthryl or phenanthryl.
Halogen atom for example has：Fluorine atom, chlorine atom, bromine atoms or iodine atom.
Embodiment of the present invention is related to a kind of Electrophtography photosensor (below, sometimes referred to as photoreceptor).It is of the invention real
Apply the sensitivity excellent of the photoreceptor involved by mode.Its reason is presumed as follows.Photoreceptor involved by present embodiment
The benzoquinone methyl compound derivative (below, sometimes referred to as benzoquinone methyl compound derivative (1)) represented containing formula (1).Benzene
In the structure of quinone methides derivative (1), at least one benzoquinone methyl part is bonded on phenyl ring by ester moiety.Cause
This, benzoquinone methyl compound derivative (1) has bigger pi-conjugated system.Therefore, in benzoquinone methyl compound derivative (1), carry
The acceptance and transporting of body (electronics) are often excellent.Further, benzoquinone methyl compound derivative (1) has R2And R3.That
, benzoquinone methyl part and ester moiety are bonded being bonded (singly-bound) and can rotating for (singly-bound) and ester moiety and phenyl ring.Cause
This, for benzoquinone methyl compound derivative (1), dissolubility in the solvent for forming photosensitive layer and in photosensitive layer
In dispersiveness be often excellent.So, it is believed that the sensitivity of the Electrophtography photosensor involved by present embodiment
Excellent.
Photoreceptor involved by present embodiment can be mono-layer electronic photographic photoreceptor (it is following, sometimes referred to as singly
Stratotype photoreceptor) or laminated electronic electrophotographic photoconductor (below, sometimes referred to as cascade type photoreceptor).
<1. single-layer type photoreceptor>
Hereinafter, reference picture 1 (a), Fig. 1 (b) and Fig. 1 (c), the structure in the case of being single-layer type photoreceptor to photoreceptor 1
Illustrate.Fig. 1 (a), Fig. 1 (b) and Fig. 1 (c) are an example for representing the photoreceptor 1 involved by present embodiment respectively
Schematic cross sectional views.
As shown in Fig. 1 (a), the photoreceptor 1 as single-layer type photoreceptor possesses conductive base 2 and photosensitive layer 3.Single-layer type
In photoreceptor, single-layer type photosensitive layer 3a is as photosensitive layer 3.Single-layer type photosensitive layer 3a is one layer of photosensitive layer 3.
As shown in Fig. 1 (b), the photoreceptor 1 as single-layer type photoreceptor can also possess：Conductive base 2, single-layer type sense
Photosphere 3a and intermediate layer (priming coat) 4.Intermediate layer 4 is arranged between conductive base 2 and single-layer type photosensitive layer 3a.Further, such as
Shown in Fig. 1 (c), protective layer 5 can also be set on single-layer type photosensitive layer 3a.
As long as single-layer type photosensitive layer 3a thickness can make single-layer type photosensitive layer fully demonstrate its function, do not do especially
Restriction.Single-layer type photosensitive layer 3a thickness is preferably less than more than 5 μm 100 μm, more preferably less than more than 10 μm 50 μm.On
State, reference picture 1 (a), Fig. 1 (b) and Fig. 1 (c), the structure of the photoreceptor 1 as single-layer type photoreceptor is illustrated.
<2. cascade type photoreceptor>
Hereinafter, reference picture 2 (a), Fig. 2 (b) and Fig. 2 (c), the structure of cascade type photoreceptor is illustrated.Fig. 2 (a), figure
2 (b) and Fig. 2 (c) are the schematic cross sectional views for the other examples for representing the photoreceptor involved by embodiment of the present invention respectively.
As shown in Fig. 2 (a), the photoreceptor 1 as cascade type photoreceptor possesses conductive base 2 and photosensitive layer 3.Photosensitive layer
3 possess charge generation layer 3b and charge transport layer 3c.In order to improve the wear resistance of cascade type photoreceptor, it is preferably：Such as Fig. 2
(a) shown in, charge generation layer 3b is set on conductive base 2, charge transport layer 3c is set on charge generation layer 3b.
As shown in Fig. 2 (b), as in the photoreceptor 1 of cascade type photoreceptor, electricity can also be set on conductive base 2
Lotus transfer layer 3c, charge generation layer 3b is set on charge transport layer 3c.
As shown in Fig. 2 (c), the photoreceptor 1 as cascade type photoreceptor can also possess：Conductive base 2, photosensitive layer 3
With intermediate layer (priming coat) 4.Intermediate layer 4 is arranged between conductive base 2 and photosensitive layer 3.Further, on photosensitive layer 3, also may be used
To set protective layer 5 (reference picture 1 (c)).
As long as charge generation layer 3b and charge transport layer 3c thickness can make each layer fully demonstrate its function, do not do
It is special to limit.Charge generation layer 3b thickness is preferably less than more than 0.01 μm 5 μm, more preferably more than 0.1 μm 3 μm with
Under.Charge transport layer 3c thickness is preferably less than more than 2 μm 100 μm, more preferably less than more than 5 μm 50 μm.
Charge generation layer 3b in photosensitive layer 3 contains electric charge producing agent.Charge generation layer 3b can also contain electric charge and produce
Layer binding resin (below, sometimes referred to as matrix resin).Charge generation layer 3b can also contain various additions as needed
Agent.It is above-mentioned, reference picture 2 (a), Fig. 2 (b) and Fig. 2 (c), the structure of the photoreceptor 1 as cascade type photoreceptor is said
It is bright.
Photosensitive layer contains：Electric charge producing agent, cavity conveying agent, benzoquinone methyl compound derivative and binding resin.Further, feel
Photosphere can also contain additive as needed.Hereinafter, the key element of cascade type photoreceptor and single-layer type photoreceptor is illustrated.
Further, the manufacture method of photoreceptor is illustrated.
<3. conductive base>
As long as conductive base can act as the conductive base of photoreceptor, it is not particularly limited.Electric conductivity base
As long as body at least surface element is formed by conductive material.The conductive base formed by conductive material can be enumerated, is come
An example as conductive base.The conductive base coated by conductive material can also be enumerated, is used as electric conductivity
Another example of matrix.Conductive material for example has：Aluminium, iron, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium or
Indium.These conductive materials may be used singly or in combination of two or more to use.Two or more combinations for example have：
Alloy (for more specifically, aluminium alloy, stainless steel or brass etc.).In these conductive materials, by electric charge from photosensitive layer to
From the point of view of the good aspect of the movement of conductive base, preferably aluminium or aluminium alloy.
The shape of conductive base suitably selects according to the structure of image processing system.The shape of conductive base is for example
Have：Sheet or drum type.Further, the thickness of conductive base suitably selects according to the shape of conductive base.
<4. benzoquinone methyl compound derivative>
In the case where photoreceptor is cascade type photoreceptor, charge transport layer contains the benzoquinones as electron acceptor compound
Methide derivatives thereof (1).In the case where photoreceptor is single-layer type photoreceptor, single-layer type photosensitive layer contains as electron transport
The benzoquinone methyl compound derivative (1) of agent.Because photosensitive layer contains benzoquinone methyl compound derivative (1), therefore present embodiment
The excellent electrical characteristic of involved photoreceptor.Benzoquinone methyl compound derivative (1) is represented by formula (1).
【Change 4】
In formula (1), R1Represent：Formula (2), C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyl groups,
Nitro, C2-C7 alkoxy carbonyl groups or halogen atom.R1The C1-C6 alkyl of expression can also have C6-C14 aryl.R1Represent
C6-C14 aryl can also have the first substituent.R2And R3It is each independent, represent：C1-C6 alkyl, C1-C6 alkoxies, C6-
C14 aryl, C1-C7 acyl groups or halogen atom.R2And R3The C1-C6 alkyl of expression can also have C6-C14 aryl.R2And R3
The C6-C14 aryl of expression can also have the second substituent.M represents less than more than 05 integer.Less than more than 25 are represented in m
Integer in the case of, several R1Each other can be with identical or different.
【Change 5】
In formula (2), R4And R5It is each independent, represent：C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyls
Base or halogen atom.R4And R5The C1-C6 alkyl of expression can also have C6-C14 aryl.R4And R5The C6-C14 virtues of expression
Base can also have the 3rd substituent.First substituent, the second substituent and the 3rd substituent are each independent, represent：C1-C6 alkane
Base, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyl groups or halogen atom.First substituent, the second substituent and the 3rd take
There can also be C6-C14 aryl for the C1-C6 alkyl of basis representation.
Hereinafter, 1,4-benzoquinone methide derivatives thereof (1) is described in detail.In formula (1), R1The halogen atom of expression is excellent
Elect chlorine atom as.R1The C2-C7 alkoxy carbonyl groups of expression are preferably C2-C4 alkoxy carbonyl groups, more preferably methoxycarbonyl group.
In formula (1), R1Formula (2), halogen atom, nitro or C2-C7 alkoxy carbonyl groups are preferably represented, more preferably
Represent chlorine atom, nitro or C2-C4 alkoxy carbonyl groups.
In formula (1), on the basis of binding site of the ester group on phenyl ring, R1Can be in ortho position (o positions), meta (m positions)
Or substituted in contraposition (p positions).Wherein, preferably ortho position or contraposition.M is preferably to represent 1 or 2.
In formula (1), R2And R3The C1-C6 alkyl of expression is preferably C1-C4 alkyl, more preferably methyl or the tert-butyl group.
In formula (2), R4And R5The C1-C6 alkyl of expression is preferably C1-C4 alkyl, more preferably methyl or the tert-butyl group.
In formula (1), it is preferably：R1Represent the formula (2), halogen atom, nitro or C2-C7 alkoxy carbonyl groups, R2With
R3C1-C4 alkyl is represented, the R in formula (2)4And R5Represent C1-C4 alkyl.
Benzoquinone methyl compound derivative (1) can have 1 or 2 benzoquinone methyl parts.Spread out in benzoquinone methyl compound
In the case that biological (1) has 1 benzoquinone methyl part, in formula (1), it is preferably：R1Represent halogen atom, nitro or
C2-C7 alkoxy carbonyl groups, R2And R3C1-C4 alkyl is represented, m represents 1 or 2.In the case where m represents 2,2 R1Preferably each other
It is different.
In the case where benzoquinone methyl compound derivative (1) has 2 benzoquinone methyl parts, in formula (1), it is preferably：
R1Represent formula (2), R2And R3C1-C4 alkyl is represented, m represents 1, the R in formula (2)4And R5Represent C1-C4 alkyl.
The specific example of benzoquinone methyl compound derivative (1) for example has：The benzoquinones first that chemical formula (1-1)~(1-5) is represented
Glycolylate derivative (following, to be recited as benzoquinone methyl compound derivative (1-1)~(1-5) respectively sometimes).
【Change 6】
【Change 7】
【Change 8】
【Change 9】
【Change 10】
From the viewpoint of the sensitivity characteristic for improving photoreceptor, in these benzoquinone methyl compound derivatives (1), it is preferably
Benzoquinone methyl compound derivative (1-1) and (1-4).
In the case where photoreceptor is cascade type photoreceptor, relative to the mass of binding resin 100 contained by charge transport layer
Part, benzoquinone methyl compound derivative (1) content is preferably more preferably 20 mass parts more than 10 mass parts below 200 mass parts
Below the mass parts of the above 100.
In the case where photoreceptor is single-layer type photoreceptor, relative to the matter of binding resin 100 contained by single-layer type photosensitive layer
Part is measured, the content of benzoquinone methyl compound derivative (1) is preferably more preferably 10 matter more than 10 mass parts below 200 mass parts
Measure more than part below 100 mass parts, particularly preferably more than 10 mass parts below 75 mass parts.
In charge transport layer, except benzoquinone methyl compound derivative (1), other electron acceptor compounds can also be contained.
In single-layer type photosensitive layer, except benzoquinone methyl compound derivative (1), other electron transporting agents can also be contained.Other electronics
Acceptor compound and electron transporting agent for example have：Quinones, diimide compounds, hydrazone compounds, malononitrile class
Compound, thiapyran class compound, trinitro- thioxanthene ketone class compound, 3,4,5,7- tetranitros -9-Fluorenone class compound, dinitro
Anthracene compound, dinitro acridine compound, tetracyanoethylene, 2,4,8- trinitro- thioxanthones, dinitro benzene, dinitro a word used for translation
Pyridine, succinic anhydride, maleic anhydride or dibromomaleic acid acid anhydride.Quinones for example has：Biphenyl quinones, azo quinones
Compound, anthraquinone analog compound, naphthoquinone compound, nitroanthracene quinones or dinitroanthraquinone class compound.These
It in electron transporting agent or electron acceptor compound, can be used alone, two or more use can also be combined.
(manufacture method of benzoquinone methyl compound derivative (1))
For example, the reaction (following, sometimes referred to as to react (R-1)) represented according to reaction equation (R-1) and reaction side
The reaction (following, sometimes referred to as to react (R-2)) or similar approach, manufacture benzoquinone methyl compound that formula (R-2) represents are spread out
Biological (1).The manufacture method of benzoquinone methyl compound derivative (1) is for example comprising reaction (R-1) and reaction (R-2).
React in (R-1), the R in formula (A) and formula (C)2And R3Respectively with the R in formula (1)2And R3Implication is identical.
R in formula (B) and formula (C)1With m respectively with the R in formula (1)1It is identical with m implications.
【Change 11】
React in (R-1), make 01 derivatives that the formula (A) of 1 equivalent represents (below, sometimes referred to as 01 derivatives
(A)) and 1 equivalent the carboxylic acid derivates (following, sometimes referred to as carboxylic acid derivates (B)) that represent of formula (B) in dehydrating condensation
(below, sometimes agent obtains the ester derivant of formula (C) expression of 1 equivalent with being reacted in the presence of catalyst in solvent
It is recited as ester derivant (C)).React in (R-1), relative to 1 mole of 01 derivatives (A), preferably add more than 1 mole 5
Dehydrating condensation agent below mole.Relative to 1 mole of the amount of the material of 01 derivatives (A), less than more than 1 mole 5 moles are added
Dehydrating condensation agent when, easily improve benzoquinone methyl compound derivative (1) yield, benzoquinone methyl compound derivative (1) carries
It is pure to become easy.Relative to 1 mole of the amount of the material of 01 derivatives (A), the catalysis of less than more than 0.1 mole 0.5 mole of addition
During agent, the yield of benzoquinone methyl compound derivative (1) is easily improved, the purification of benzoquinone methyl compound derivative (1) becomes easy.
The reaction time for reacting (R-1) is preferably less than 15 hours more than 3 hours.The reaction temperature for reacting (R-1) is preferably more than 0 DEG C
Less than 50 DEG C.Solvent for example has：Chloroform or dichloromethane.Dehydrating condensation agent for example has：Dicyclohexylcarbodiimide or
Person's carbonyl dimidazoles.Catalyst for example has：Dimethylamino naphthyridine or triethylamine.
React in (R-2), the R in formula (C)1、R2、R3With m respectively with the R in formula (1)1、R2、R3It is identical with m implications.
【Change 12】
React in (R-2), the ester derivant (C) of 1 equivalent is reacted in the presence of oxidant in solvent, obtain
The benzoquinone methyl compound derivative (1) of 1 equivalent.React in (R-2), relative to 1 mole of ester derivant (C), preferably add 1
Less than 10 moles of oxidant more than mole.Relative to 1 mole of the amount of the material of ester derivant (C), addition rubs for more than 1 mole 10
During oxidant below you, the yield of benzoquinone methyl compound derivative (1) is easily improved, benzoquinone methyl compound derivative (1)
Purification becomes easy.The reaction time for reacting (R-2) is preferably less than 15 hours more than 3 hours.React the reaction temperature of (R-1)
Preferably less than more than 0 DEG C 50 DEG C.Solvent for example has：Chloroform or dichloromethane.Oxidant for example has：Potassium permanganate,
Hydrogen peroxide, metachloroperbenzoic acid or Peracetic acid.
In the manufacture of benzoquinone methyl compound derivative (1), other processes can also be contained as needed (for example, purification
Process).Such process for example has purification process.Method of purification for example have well-known method (for more specifically, mistake
Filter, chromatography or crystallization etc.).
<5. cavity conveying agent>
For example, nitrogenous cyclic compound or fused polycyclic compound can be used as cavity conveying agent to use.It is nitrogenous
Cyclic compound and fused polycyclic compound for example have：Diamine derivative (for more specifically, N, N, N ', N '-tetraphenyl benzene
Diamine derivative, N, N, N ', N '-tetraphenyl benzidine derivative, N, N, N ', N '-tetraphenyl naphthylenediamine derivative or N, N,
N ', N '-tetraphenyl phenanthrylene diamines (N, N, N ', N '-tetraphenyl phenanthrylene diamine) derivative
Deng), furodiazole compound (for more specifically, 2,5- bis- (4- methylaminos phenyl) -1,3,4- oxadiazoles etc.), styrene
Compound (for more specifically, 9- (4- lignocaines styryl) anthracene etc.), carbazole compound (for more specifically, poly- second
Alkenyl carbazole etc.), organopolysilane compound, (for more specifically, 1- phenyl -3- is (to dimethylamino for pyrazoline compounds
Base phenyl) pyrazoline etc.), hydrazone compounds, Benzazole compounds, dislike azole compounds, isoxazole class compound, thiazoles
Compound, thiadiazole compound, glyoxaline compound, pyrazole compound or triazole class compounds.These cavity conveying agent
In, it can be used alone, two or more use can also be combined.In these cavity conveying agent, preferably formula (3) table
The compound (benzidine derivative) shown.
【Change 13】
In formula (3), R21、R22、R23、R24、R25And R26It is each independent, represent C1-C6 alkyl or C1-C6 alkoxies.
R, s, v and w are each independent, represent less than more than 05 integer.T and u is each independent, represents less than more than 04 integer.
In formula (3), R21、R22、R23、R24、R25And R26It is each independent, preferably represent C1-C6 alkyl, more preferably table
Show C1-C3 alkyl, more preferably represent methyl.R, s, v, w, t and u are preferably to represent 1.
The compound that formula (3) represents is preferably that the compound represented by chemical formula (H-1) is (below, sometimes referred to as empty
Cave agent delivery (H-1)).
【Change 14】
In the case where photoreceptor is cascade type photoreceptor, relative to the mass of binding resin 100 contained by charge transport layer
Part, the content of cavity conveying agent is preferably 100 matter more preferably more than 20 mass parts more than 10 mass parts below 200 mass parts
Measure below part.
In the case where photoreceptor is single-layer type photoreceptor, relative to the matter of binding resin 100 contained by single-layer type photosensitive layer
Part is measured, the content of cavity conveying agent is preferably more than 10 mass parts below 200 mass parts, more preferably more than 10 mass parts 100
Below mass parts, particularly preferably more than 10 mass parts below 90 mass parts.
<6. electric charge producing agent>
As long as the electric charge producing agent of electric charge producing agent photoreceptor, is not particularly limited.Electric charge producing agent example
If any：Phthalocyanine pigment, class pigment, disazo pigment, trisazo pigment, dithione pyrrolopyrrole (dithioketo-
Pyrrolopyrrole) pigment, without metal naphthalene phthalocyanine pigment, metal naphthalene phthalocyanine pigment, square acid color, indigo pigments, azulene
Pigment, cyanine pigment, the powder of inorganic light-guide material (for more specifically, selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide or non-crystalline silicon etc.)
End, pyrylium pigments, anthanthrene quinones pigment, triphenylmethane pigment, intellectual circle's class pigment, toluene amines pigment, pyrazolines face
Material or quinacridone-type pigments.Electric charge producing agent can be used alone, and can also combine two or more use.
Phthalocyanine pigment for example has：(following, sometimes referred to as electric charge produces the metal-free phthalocyanine that chemical formula (C-1) represents
Agent (C-1)) or metal phthalocyanine.Metal phthalocyanine for example has：The titanyl phthalocyanine that chemical formula (C-2) represents is (below, sometimes referred to as
Electric charge producing agent (C-2)), hydroxy gallium phthalocyanine or gallium chlorine phthalocyaninate.Phthalocyanine pigment can be crystallization or it is noncrystalline.
The crystal shape (for example, α types, β types, Y types, V-type or II types) of phthalocyanine pigment is not particularly limited, can be used various
The phthalocyanine pigment of crystal shape.
【Change 15】
【Change 16】
The crystallization of metal-free phthalocyanine for example has：(following, sometimes referred to as X-type is without metal phthalein for the X-type crystal of metal-free phthalocyanine
Cyanines).The crystallization of titanyl phthalocyanine for example has：The α types of titanyl phthalocyanine, β types or Y types crystal (following, sometimes referred to as α types, β types
Or Y-shaped oxygen titanium phthalocyanines).The crystallization of hydroxy gallium phthalocyanine for example has：The V-type crystal of hydroxy gallium phthalocyanine.The crystallization example of gallium chlorine phthalocyaninate
If any：The II type crystal of gallium chlorine phthalocyaninate.
For example, in the image processing system of digit optical formula, it is preferable to use have in more than 700nm wavelength region
The photoreceptor of sensitivity.Such image processing system for example has：Possess the laser printer or fax of semiconductor laser
Machine.Due to having a high quantum production rate in more than 700nm wavelength region, therefore preferably phthalocyanine pigment is as electric charge producing agent,
More preferably metal-free phthalocyanine or titanyl phthalocyanine are as electric charge producing agent.Contain benzoquinone methyl compound derivative (1) in photosensitive layer
In the case of, in order to further improve the electrical characteristic of photoreceptor, more preferably X-type metal-free phthalocyanine or Y-shaped oxygen titanium phthalocyanines is made
For electric charge producing agent.
Y-shaped oxygen titanium phthalocyanines are in CuK α characteristic X-ray difraction spectrums, for example, at 27.2 ° of Bragg angle (2 θ ± 0.2 °)
With main peak.Main peak in CuK α characteristic X-ray difraction spectrums refers to that in Bragg angle (2 θ ± 0.2 °) be less than more than 3 ° 40 °
Scope in have the first big or second largest intensity peak.
(measuring method of CuK α characteristic X-ray difraction spectrums)
One example of the measuring method of CuK α characteristic X-ray difraction spectrums is illustrated.By sample (titanyl phthalocyanine)
It is filled into the sample of X-ray diffraction device (for example, Rigaku Corporation manufacture " RINT (Japan registration trade mark) 1100 ")
In product support, X-ray diffraction spectra is measured.Measuring condition be X-ray tube Cu, tube voltage 40kV, tube current 30mA and
The wavelength of CuK α characteristic X-raysMeasurement range (2 θ) is less than more than 3 ° 40 ° (3 ° of initial angle, 40 ° of angular stops), is swept
It is 10 °/point to retouch speed.
In photoreceptor used in image processing system using short-wavelength laser light sources, preferably using anthanthrene quinones face
Material is used as electric charge producing agent.The wavelength of short wavelength laser is, for example, more than 350nm below 550nm.
In the case where photoreceptor is cascade type photoreceptor, relative to the matter of matrix resin 100 contained in charge generation layer
Part is measured, the content of electric charge producing agent is preferably more than 5 mass parts below 1000 mass parts, more preferably more than 30 mass parts 500
Below mass parts.
In the case where photoreceptor is single-layer type photoreceptor, relative to the binding resin 100 contained in single-layer type photosensitive layer
Mass parts, the content of electric charge producing agent is preferably more than 0.1 mass parts below 50 mass parts, more preferably more than 0.5 mass parts
Below 30 mass parts, particularly preferably more than 0.5 mass parts below 6.0 mass parts.
<7. binding resin>
Binding resin for example has：Thermoplastic resin, thermosetting resin or light-cured resin.Thermoplastic resin for example has：
Polycarbonate resin, polyarylate resin, styrene-butadiene resins, SAN, Styrene maleic acid
Resin, acrylic resin, styrene-acrylic resin, polyvinyl resin, ethylene-vinyl acetate resin, chlorinated polyethylene
Olefine resin, Corvic, acrylic resin, ionomer resin, vinyl chloride-vinyl acetate resin, alkyd resin, polyamides
Polyimide resin, polyurethane resin, polysulfone resin, diallyl phthalate resin, ketone resin, polyvinyl butyral resin
Resin, polyester resin or polyether resin.Thermosetting resin for example has：Silicone resin, epoxy resin, phenolic resin, ureaformaldehyde tree
Fat or melmac.Light-cured resin for example has：Epoxy-acrylic resinoid (for more specifically, epoxide
Acrylic acid derivative addition product etc.) or polyurethane-acrylate resinoid (for more specifically, the third of urethanes
Gadoleic acid derivative addition product etc.).These binding resins can be used alone, and can also combine two or more use.
In these resins, from obtaining the harmonious excellent list of processability, mechanical strength, optical property and wear resistance
From the perspective of stratotype photosensitive layer and charge transport layer, preferably polycarbonate resin.Polycarbonate resin for example has：Under having
State bisphenol z-polycarbonate resin (following, the sometimes referred to as makrolon of the repeat unit of chemical formula (Resin-1) expression
Resin (Resin-1)).
【Change 17】
The viscosity average molecular weigh of binding resin is preferably 40, more than 000, more preferably 40, and more than 000 52, less than 500.It is viscous
In the case that the viscosity average molecular weigh of knot resin is 40, more than 000, the wear resistance of photoreceptor is easily improved.Binding resin it is viscous
In the case that molecular weight is 52, less than 500, when forming photosensitive layer, binding resin is readily soluble in solvent, and charge transport layer is used
The viscosity of coating fluid or single-layer type photosensitive layer coating fluid will not be too high.As a result, easily form charge transport layer or individual layer
Type photosensitive layer.
<8. matrix resin>
In the case where photoreceptor is cascade type photoreceptor, charge generation layer can also contain matrix resin.Matrix resin
As long as the matrix resin in photoreceptor can be applied, it is not particularly limited.Matrix resin for example has：Thermoplastic resin
Fat, thermosetting resin or light-cured resin.Thermoplastic resin for example has：Styrene-butadiene resins, styrene-acrylonitrile
Resin, Styrene maleic acid resin, styrene-acrylic resin, acrylic resin, polyvinyl resin, ethene-
Vinyl acetate resin, chlorinated polyethylene resin, Corvic, acrylic resin, ionomer, vinyl chloride-vinyl acetate
Ester resin, alkyd resin, polyamide, polyurethane resin, polycarbonate resin, polyarylate resin, polysulfone resin,
Diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin or polyester resin.Thermosetting
Resin for example has：Silicone resin, epoxy resin, phenolic resin, Lauxite, melmac or other bridging property thermosettings
Property resin.Light-cured resin for example has：(for more specifically, the acrylic acid of epoxide derives epoxy-acrylic resinoid
Thing addition product etc.) or polyurethane-acrylate resinoid (for more specifically, the acrylic acid derivative of urethanes adds
Into thing etc.).Matrix resin can be used alone, and can also combine two or more use.
The matrix resin contained in charge generation layer is preferably the binding resin for being different from containing in charge transport layer.Reason
It is in order that charge generation layer is not dissolved in the solvent of charge transport layer coating fluid.Wherein, in the system of cascade type photoreceptor
In making, it can be common that charge generation layer is formed on conductive base and charge transport layer is formed on charge generation layer, and
It is the coating charge transport layer coating fluid on charge generation layer when forming charge transport layer.
<9. additive>
, can also be according to need in the photosensitive layer (charge generation layer, charge transport layer or single-layer type photosensitive layer) of photoreceptor
Contain various additives.Additive for example has：Degradation inhibitor (for more specifically, antioxidant, radical scavenger,
Quencher or ultra-violet absorber etc.), softening agent, surface modifier, extender, thickener, dispersion stabilizer, wax, donor,
Surfactant, plasticizer, sensitizer or levelling agent.Antioxidant for example has：Hindered phenol (for more specifically, two tertiary fourths
Base paracresol etc.), hindered amine, p-phenylenediamine, aromatic yl paraffin, hydroquinones, spiral shell benzodihydropyran (spirochroman), spiral shell
Indone (spiroindanone) or their derivative；Organosulfur compound or organic phosphorus compound.
<10. intermediate layer>
Intermediate layer (priming coat) is for example containing inorganic particle and resin (intermediate layer resin).It is considered that：Pass through centre
The presence of layer, electric leakage can be suppressed by, which being able to maintain that, occurs the state of insulation of this degree, while makes electric caused by exposure photoreceptor
Stream flowing is smooth, suppresses the increase of resistance.
Inorganic particle for example has：Particle, the metal oxide of metal (for more specifically, aluminium, iron or copper etc.) (have more
For body ground, titanium dioxide, aluminum oxide, zirconium oxide, tin oxide either zinc oxide etc.) particle or nonmetal oxide (more
Specifically, silica etc.) particle.These inorganic particles can be used alone, and can also combine two or more
To use.
As long as intermediate layer resin can be used for being formed the resin in intermediate layer, there is no particular limitation.Intermediate layer
Various additives can also be contained.Additive is identical with the additive of photosensitive layer.
<11. the manufacture method of photoreceptor>
In the case where photoreceptor is cascade type photoreceptor, for example, the manufacture of cascade type photoreceptor is as follows.First, to electricity
Lotus produces layer and prepared with coating fluid and charge transport layer with coating fluid.By charge generation layer coating solution in electric conductivity
On matrix, coated film is formed.Dry coated film, so as to form charge generation layer.Next, by charge transport layer coating fluid
It is coated on charge generation layer, forms coated film.Dry coated film, so as to form charge transport layer.Thus, cascade type is manufactured
Photoreceptor.
Charge generation layer with coating fluid for example containing：Electric charge producing agent, matrix resin, solvent and additive.For example, pass through
Make electric charge producing agent, matrix resin and additive dissolving or disperse in a solvent, to prepare charge generation layer coating fluid.Electricity
Lotus transfer layer with coating fluid for example containing：Cavity conveying agent, the benzoquinone methyl compound derivative as electron acceptor compound
(1), binding resin and additive.For example, spread out by the benzoquinone methyl compound for making cavity conveying agent, being used as electron acceptor compound
Biological (1), binding resin and additive dissolving disperse in a solvent, to prepare charge transport layer coating fluid.
Next, in the case where photoreceptor is single-layer type photoreceptor, for example, by single-layer type photosensitive layer coating solution
On conductive base, coated film is formed, then by drying coated film, so as to manufacture single-layer type photoreceptor.Single-layer type is photosensitive
Layer with coating fluid for example containing：Electric charge producing agent, cavity conveying agent, the benzoquinone methyl compound derivative as electron transporting agent
(1), binding resin and additive.For example, make electric charge producing agent, cavity conveying agent, the benzoquinone methyl as electron transporting agent
Thing derivative (1), binding resin and additive dissolving disperse in a solvent, to prepare single-layer type photosensitive layer coating fluid.
Charge generation layer coating fluid, charge transport layer coating fluid or single-layer type photosensitive layer (below, have with coating fluid
When these coating fluids are all recited as coating fluid) as long as in the solvent that contains can by each composition dissolving contained by coating fluid or
It is scattered, it is not particularly limited.Solvent for example has：Alcohol (for more specifically, methanol, ethanol, isopropanol or butanol
Deng), aliphatic hydrocarbon (for more specifically, n-hexane, octane or hexamethylene etc.), aromatic hydrocarbon (for more specifically, benzene, first
Benzene or dimethylbenzene etc.), halogenated hydrocarbon (for more specifically, dichloromethane, dichloroethanes, carbon tetrachloride or chlorobenzene etc.), ether
(for more specifically, dimethyl ether, diethyl ether, tetrahydrofuran, glycol dimethyl ether, diethylene glycol dimethyl ether or propane diols list first
Ether etc.), ketone (for more specifically, acetone, methyl ethyl ketone or cyclohexanone etc.), ester (for more specifically, ethyl acetate
Either methyl acetate etc.), dimethylformaldehyde, dimethylformamide or dimethyl sulfoxide (DMSO).These solvents can be used alone one
Kind, two or more use can also be combined.In order to improve operability during manufacture photoreceptor, preferably using non-halogenated solvent
(solvent beyond halogenated hydrocarbon) is used as solvent.
By mixing and being distributed in solvent each composition, coating fluid is prepared.For the operation for mixing or disperseing, such as
Ball mill, roller mill, ball mill, grater, paint shaker or ultrasonic dispersing machine can be used.
For example, in order to improve the dispersiveness of each composition, coating fluid can also contain surfactant.
For the method being coated using coating fluid, as long as coating fluid can be uniformly coated on to electric conductivity base
Method on body, is not particularly limited.Coating method for example has：Dip coating, spraying process, spin-coating method or stick coating method.
As long as the method for drying coated liquid can remove at least one of of the solvent in coating fluid, spy is not
Other restriction.For example, the method that (heated-air drying) is heat-treated using high-temperature drier or pressure Reduction Dryer can be enumerated,
It is used as minimizing technology.For example, heat treatment condition be preferably less than more than 40 DEG C 150 DEG C temperature and 120 minutes more than 3 minutes
The following time.
In addition, as needed, the manufacture method of photoreceptor can also further comprise forming the process in intermediate layer and formation
One or both of process of protective layer.Form the process in intermediate layer and formed in the process of protective layer, suitably select many institutes
Known method.
It is above-mentioned, the photoreceptor involved by present embodiment is illustrated.According to the photoreceptor of present embodiment, electrically
Characteristic performance is excellent.
【Embodiment】
Hereinafter, more specific description is carried out to the present invention using embodiment.But the present invention is not defined in any way
The scope of embodiment.
<1. the material of photoreceptor>
Prepare following cavity conveying agent, electric charge producing agent and electron transporting agent, as the list for forming single-layer type photoreceptor
The material of stratotype photosensitive layer.
<1-1. electron transporting agent>
Respectively with following method, benzoquinone methyl compound derivative (1-1)~(1-5) as electron transporting agent is manufactured.
<The manufacture of 1-1-1. benzoquinone methyl compound derivatives (1-1)>
According to reaction (r-1) and reaction (r-2), manufacture benzoquinone methyl compound derivative (1-1).
【Change 18】
React in (r-1), the 01 derivatives (below, sometimes referred to as 01 derivatives (A-1)) for representing chemical formula (A-1)
The carboxylic acid derivates (below, sometimes referred to as carboxylic acid derivates (B-1)) represented with chemical formula (B-1) are reacted, and are changed
The ester derivant (below, sometimes referred to as ester derivant (C-1)) that formula (C-1) represents.Specifically, in reaction vessel,
It is put into 01 derivatives (A-1) 2.36g (10mmol), carboxylic acid derivates (B-1) 2.02g (10mmol), the diformazan as catalyst
Aminopyridine 0.18g (1.5mmol), chloroform, prepare chloroform soln.Again using as the dicyclohexyl of dehydrating condensation agent
Carbodiimide 3.2g (15mmol) is added drop-wise in reaction vessel, and the inclusion stirring 8 to reaction vessel under room temperature (25 DEG C) is small
When.Then, the inclusion of reaction vessel is filtered, obtains filtrate.The solvent of gained filtrate is evaporated, obtains residue.
Using chloroform as solvent, as silica gel column chromatography, the residue to obtained by purifies.As a result, obtain ester derivative
Thing (C-1).React in (r-1), based on 01 derivatives (A-1), the yield of ester derivant (C-1) is 2.7g, ester derivant (C-1)
Yield be 64mol%.
【Change 19】
React in (r-2), ester derivant (C-1) 2.1g (5mmol) and chloroform are put into reaction vessel, prepare three
Chloromethanes solution.Further, the potassium permanganate 3.9g (25mmol) as oxidant is put into reaction vessel, in room temperature (25
DEG C) under the inclusion of reaction vessel is stirred 8 hours.Then, the inclusion of reaction vessel is filtered, obtains filtrate.Steam
Hair falls the solvent of gained filtrate, obtains residue.Using chloroform as solvent, as silica gel column chromatography to obtained by it is residual
Thing is stayed to be purified.As a result, obtain benzoquinone methyl compound derivative (1-1).React in (r-2), based on ester derivant (C-
1), the yield of benzoquinone methyl compound derivative (1-1) is 1.25g, and the yield of benzoquinone methyl compound derivative (1-1) is
60mol%.
<1-1-2. benzoquinone methyl compound derivatives (1-2)~(1-5) manufacture>
In addition to some below change, by the manufacture identical method with benzoquinone methyl compound derivative (1-1), divide
Zhi Zao not benzoquinone methyl compound derivative (1-2)~(1-5).
In table 1,01 derivatives (A), carboxylic acid derivates (B) and ester derivant (C) in reaction (r-1) are represented.Wherein, alcohol
Derivative (A) and carboxylic acid derivates (B) are to react the reactant (Reactant) in (r-1).The alcohol used in (r-1) will be reacted
Derivative (A-1) and carboxylic acid derivates (B-1) are changed to 01 derivatives (A) and carboxylic acid derivates (B) described in table 1 respectively.
As a result, obtain replacing ester derivant (C-2)~(C-5) of ester derivant (C-1).In table 1, the production of ester derivant (C) is represented
Amount and yield.
In table 1, A-1 and A-2 in the row " species " of 01 derivatives (A) represent 01 derivatives (A-1) and (A-2) respectively.
B-1, B-2, B-3, B-4 and B-5 in the row " species " of carboxylic acid derivates (B) represent respectively 01 derivatives (B-1), (B-2),
(B-3), (B-4) and (B-5).C-1, C-2, C-3, C-4 and C-5 in the row " species " of ester derivant (C) represent that ester spreads out respectively
Biological (C-1), (C-2), (C-3), (C-4) and (C-5).
【Table 1】
01 derivatives (A-2) are represented by following chemical formula (A-2).Carboxylic acid derivates (B-2)~(B-5) is respectively by followingization
Formula (B-2)~(B-5) is represented.Ester derivant (C-2)~(C-5) is represented by following chemical formula (C-2)~(C-5) respectively.
【Change 20】
【Change 21】
【Change 22】
【Change 23】
【Change 24】
【Change 25】
【Change 26】
【Change 27】
【Change 28】
In table 2, ester derivant (C) and benzoquinone methyl compound derivative (1) in reaction (r-2) are represented.Wherein, ester derives
Thing (C) is to react the reactant (Reactant) in (r-2).The ester derivant (C-1) used in reaction (r-2) is changed to table
Ester derivant (C) described in 2.As a result, obtain deriving instead of the benzoquinone methyl compound of benzoquinone methyl compound derivative (1-1)
Thing (1-2)~(1-5).In table 2, the yield and yield of benzoquinone methyl compound derivative (1) are represented.
In table 2, C-1, C-2, C-3, C-4 and C-5 in the row " species " of ester derivant (C) represent ester derivant respectively
(C-1), (C-2), (C-3), (C-4) and (C-5).1-1,1-2,1- in the row " species " of benzoquinone methyl compound derivative (1)
3rd, 1-4 and 1-5 represents benzoquinone methyl compound derivative (1-1), (1-2), (1-3), (1-4) and (1-5) respectively.
【Table 2】
Next, using fourier-transform infrared spectrophotometer, (PerkinElmer companies manufacture " SPECTRUM
ONE "), benzoquinone methyl compound derivative (1-1)~(1-5) of manufacture infrared absorption spectroscopy is measured.Pass through KBr (bromines
Change potassium) pressed disc method, carry out the preparation of sample.According to the infrared absorption spectroscopy of measurement, confirm to have obtained benzoquinone methyl compound respectively
Derivative (1-1)~(1-5).Wherein, with benzoquinone methyl compound derivative (1-1) and (1-4) for typical example.
Fig. 3~Fig. 4 represents benzoquinone methyl compound derivative (1-1) and the infrared absorption spectroscopy of (1-4) respectively.Fig. 3~Fig. 4
In, the longitudinal axis represents transmissivity (%), and transverse axis represents wave number (unit：cm-1).The unit % of Fig. 3~Fig. 4 longitudinal axis (transmissivity) is
Arbitrary unit.Hereinafter, the wave number (vMAX) of the absorption peak of infrared absorption spectroscopy is represented.
Benzoquinone methyl compound derivative (1-1)：IR cm-1：2967,1720,1655,1317,1244,1154,921,879.
Benzoquinone methyl compound derivative (1-4)：IR cm-1：2963,1725,1657,1280,1109,755.
<1-1-4. the preparation of compound (E-1), compound (E-2) and compound (E-3)>
Prepare the compound that chemical formula (E-1), chemical formula (E-2) and chemical formula (E-3) represent (below, sometimes respectively to remember
Carry as compound (E-1), (E-2) and (E-3)), as electron transporting agent.
【Change 29】
【Change 30】
【Change 31】
<1-2. cavity conveying agent>
Prepare it is stated that the cavity conveying agent (H-1) crossed.
<1-3. electric charge producing agent>
Prepare it is stated that electric charge producing agent (C-1)~(C-2) crossed.Electric charge producing agent (C-1) is that chemical formula (C-1) represents
Metal-free phthalocyanine (X-type metal-free phthalocyanine).Further, the crystalline texture of electric charge producing agent (C-1) is X-type.
Electric charge producing agent (C-2) is the titanyl phthalocyanine (Y-shaped oxygen titanium phthalocyanines) that chemical formula (C-2) represents.Further, electric charge produces
The crystalline texture of agent (C-2) is Y types.In the X-ray diffraction spectra of Y-shaped oxygen titanium phthalocyanines, have confirmed that Bragg angle (2 θ ±
0.2 °)=27.2 ° there is main peak.
<1-4. binding resin>
Prepare polycarbonate resin (Resin-1) (the Teijin Ltd's manufacture illustrated in first embodiment
" PANLITE (Japan registration trade mark) TS-2050 "；Viscosity average molecular weigh 50,000), as binding resin.
<2. the manufacture of single-layer type photoreceptor>
Using for forming the material of photosensitive layer, single-layer type photoreceptor (A-1)~(A-10) and single-layer type photoreceptor are manufactured
(B-1)~(B-6).
<The manufacture of 2-1. single-layer types photoreceptor (A-1)>
Using the mass parts of electric charge producing agent (C-1) 5, the mass parts of cavity conveying agent (H-1) 80, the benzoquinones as electron transporting agent
The mass parts of methide derivatives thereof (1-1) 40, the mass parts of polycarbonate resin (Resin-1) 100 as binding resin, conduct
The mass parts of tetrahydrofuran 800 of solvent are added in container.Using ball mill, by these material (electric charge producing agent (C-1), skies
Cave agent delivery (H-1), benzoquinone methyl compound derivative (1-1) and polycarbonate resin (Resin-1)) with solvent to mix 50 small
When, material is distributed in solvent.Thus, single-layer type photosensitive layer coating fluid is obtained.In the aluminum drum as conductive base
On shape supporter (diameter 30mm, total length 238.5mm), upper single-layer type photosensitive layer coating fluid is coated with using dip coating, is formed and applied
Cloth film.Make coated film in 100 DEG C of heated-air dryings 30 minutes.Thus, single-layer type photosensitive layer (thickness 30 is formed on conductive base
μm).As a result, obtain single-layer type photoreceptor (A-1).
<2-2. single-layer types photoreceptor (A-2)~(A-10) and single-layer type photoreceptor (B-1)~(B-6) manufacture>
In addition to some below change, by the manufacture identical method with single-layer type photoreceptor (A-1), manufacture respectively
Single-layer type photoreceptor (A-2)~(A-10) and single-layer type photoreceptor (B-1)~(B-6).By single-layer type photoreceptor (A-1) manufacture
The middle electric charge producing agent (C-1) used is changed to the electric charge producing agent of species shown in table 3.By single-layer type photoreceptor (A-1)
Used in manufacture, benzoquinone methyl compound derivative (1-1) as electron transporting agent is changed to the electronics of species shown in table 3
Agent delivery.In addition, in table 3, photoreceptor (A-1)~(A-10) and photoreceptor (B-1)~(B-6) structure are illustrated.In table 3,
CGM, HTM and ETM represent electric charge producing agent, cavity conveying agent and electron transporting agent respectively.In table 3, the x-H in row " CGM "2Pc
Represent X-type metal-free phthalocyanine (electric charge producing agent (C-1)) and Y-shaped oxygen titanium phthalocyanines (electric charge producing agent (C- respectively with Y-TiOPc
2)).The H-1 arranged in " HTM " represents cavity conveying agent (H-1).1-1~1-5 and E-1~E-3 in row " ETM " represent benzene respectively
Quinone methides derivative (1-1)~(1-5) and compound (E-1)~(E-3).
<3. the performance evaluation of photoreceptor>
<The sensitivity evaluating characteristics of 3-1. single-layer type photoreceptors>
Single-layer type photoreceptor (A-1)~(A-10) and single-layer type photoreceptor (B-1)~(B-6) of manufacture are felt respectively
Photometric property is evaluated.Sensitivity evaluating characteristics are carried out in the environment of 23 DEG C of temperature and humidity 60%RH.First, using drum
Sensitivity test machine (manufacture of GENTEC Co., Ltd.), makes the surface of single-layer type photoreceptor powered into positive polarity.By charged condition
It is set as the rotating speed 31rpm of single-layer type photoreceptor and flows into the μ of electric current+8 A of single-layer type photoreceptor.By the individual layer after steel bands electricity
The surface potential of type photoreceptor is set as+700V.Then, using bandpass filter, taken out from the white light of Halogen lamp LED monochromatic
Light (wavelength 780nm, half width 20nm, the μ J/cm of light energy 1.52).Table by the monochromatic light exposure of taking-up to single-layer type photoreceptor
On face.The surface potential of single-layer type photoreceptor when passing through 0.5 second again after terminating to irradiation measures.The surface that will be measured
Current potential is designated as sensitivity current potential (VL, unit V).Sensitivity current potential (the V for the single-layer type photoreceptor measuredL) be shown in Table 3 below.
In addition, sensitivity current potential (VL) absolute value it is smaller, represent single-layer type photoreceptor electrical characteristic it is more excellent.
【Table 3】
As shown in table 3, in photoreceptor (A-1)~(A-10), photosensitive layer contain benzoquinone methyl compound derivative (1-1)~
One kind in (1-5) is as electron transporting agent.These benzoquinone methyl compound derivative (1-1)~(1-5) are that formula (1) represents
Compound.Further, in photoreceptor (A-1)~(A-10), sensitivity current potential VLIt is more than+107V below+116V.
As shown in table 3, in photoreceptor (B-1)~(B-6), photosensitive layer contains compound (E-1), (E-2) or (E-3)
As electron transporting agent.Compound (E-1), (E-2) and (E-3) is not the compound that formula (1) represents.Further, photoreceptor (B-
1) in~(B-6), sensitivity current potential VLIt is more than+119V below+130V.
Photoreceptor (A-1)~(A-10) containing benzoquinone methyl compound derivative (1-1)~(1-5) is with containing compound
(E-1)~(E-3) photoreceptor (B-1)~(B-6) is compared, it is clear that sensitivity excellent.
In view of all of the above, it is evident that when containing the benzoquinone methyl compound derivative that formula (1) represents in the photosensitive layer of photoreceptor,
The sensitivity excellent of photoreceptor.
Claims (10)
1. a kind of Electrophtography photosensor, possesses conductive base and photosensitive layer, it is characterised in that
The photosensitive layer contains electric charge producing agent, cavity conveying agent, benzoquinone methyl compound derivative and binding resin,
The benzoquinone methyl compound derivative by formula (1) represent,
【Change 1】
In the formula (1),
R1Represent：Formula (2), C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyl groups, nitro, C2-C7 alcoxyl carbonyls
Base or halogen atom,
R1The C1-C6 alkyl represented can also have C6-C14 aryl,
R1The C6-C14 aryl represented can also have the first substituent,
R2And R3It is each independent, represent：Can also have C1-C6 alkyl, C1-C6 alkoxies, the C6-C14 virtue of C6-C14 aryl
Base, C1-C7 acyl groups or halogen atom,
R2And R3The C1-C6 alkyl represented can also have C6-C14 aryl,
R2And R3The C6-C14 aryl represented can also have the second substituent,
M represents less than more than 05 integer,
In the case where m represents less than more than 25 integer, several R1Each other can with identical or different,
【Change 2】
In the formula (2),
R4And R5It is each independent, C1-C6 alkyl, C1-C6 alkoxies, C6-C14 aryl, C1-C7 acyl groups or halogen atom are represented,
R4And R5The C1-C6 alkyl represented can also have C6-C14 aryl,
R4And R5The C6-C14 aryl represented can also have the 3rd substituent,
First substituent, second substituent and the 3rd substituent are each independent, represent C1-C6 alkyl, C1-C6
Alkoxy, C6-C14 aryl, C1-C7 acyl groups or halogen atom,
The C1-C6 alkyl of first substituent, second substituent and the 3rd substitution basis representation can also have
There is C6-C14 aryl.
2. Electrophtography photosensor according to claim 1, it is characterised in that
In the formula (1),
R1The formula (2), halogen atom, nitro or C2-C7 alkoxy carbonyl groups are represented,
R2And R3C1-C4 alkyl is represented,
In the formula (2),
R4And R5Represent C1-C4 alkyl.
3. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
In the formula (1),
R1Halogen atom, nitro or C2-C7 alkoxy carbonyl groups are represented,
R2And R3C1-C4 alkyl is represented,
M represents 1 or 2,
In the case where m represents 2,2 R1It is different from each other.
4. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
In the formula (1),
R1The formula (2) is represented,
R2And R3C1-C4 alkyl is represented,
M represents 1,
In the formula (2),
R4And R5Represent C1-C4 alkyl.
5. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
The benzoquinone methyl compound derivative by chemical formula (1-1), chemical formula (1-2), chemical formula (1-3), chemical formula (1-4) or
Person's chemical formula (1-5) expression,
【Change 1】
6. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
The cavity conveying agent contains the compound of formula (3) expression,
【Change 3】
In the formula (3),
R21、R22、R23、R24、R25And R26It is each independent, C1-C6 alkyl or C1-C6 alkoxies are represented,
R, s, v and w are each independent, represent less than more than 05 integer,
T and u is each independent, represents less than more than 04 integer.
7. Electrophtography photosensor according to claim 6, it is characterised in that
In the formula (3),
R21、R22、R23、R24、R25And R26It is each independent, C1-C6 alkyl is represented,
R, s, v, w, t and u represent 1.
8. Electrophtography photosensor according to claim 6, it is characterised in that
The cavity conveying agent by chemical formula (H-1) represent,
【Change 1】
9. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
The electric charge producing agent contains X-type metal-free phthalocyanine or Y-shaped oxygen titanium phthalocyanines.
10. the Electrophtography photosensor according to claims 1 or 2, it is characterised in that
The photosensitive layer is single-layer type photosensitive layer.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2016142357A JP2018013574A (en) | 2016-07-20 | 2016-07-20 | Electrophotographic photoreceptor |
| JP2016-142357 | 2016-07-20 |
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| CN107643658A true CN107643658A (en) | 2018-01-30 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114539518A (en) * | 2022-02-22 | 2022-05-27 | 苏州理硕科技有限公司 | Polymer, photoresist layer and photoetching process |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP6504126B2 (en) * | 2016-07-20 | 2019-04-24 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor |
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|---|---|---|---|---|
| CN1523453A (en) * | 2002-11-18 | 2004-08-25 | 三星电子株式会社 | Polymer having stilbenquinone structure and electrophotographic photoreceptor containing the same |
| CN101371201A (en) * | 2006-01-18 | 2009-02-18 | 富士电机电子技术株式会社 | Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus |
| CN103415498A (en) * | 2010-12-06 | 2013-11-27 | 赛泽恩有限公司 | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| CN104345584A (en) * | 2013-07-31 | 2015-02-11 | 京瓷办公信息系统株式会社 | Electrophotographic photosensitive member and image forming apparatus |
-
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- 2016-07-20 JP JP2016142357A patent/JP2018013574A/en active Pending
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1523453A (en) * | 2002-11-18 | 2004-08-25 | 三星电子株式会社 | Polymer having stilbenquinone structure and electrophotographic photoreceptor containing the same |
| CN101371201A (en) * | 2006-01-18 | 2009-02-18 | 富士电机电子技术株式会社 | Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus |
| CN103415498A (en) * | 2010-12-06 | 2013-11-27 | 赛泽恩有限公司 | Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers |
| CN104345584A (en) * | 2013-07-31 | 2015-02-11 | 京瓷办公信息系统株式会社 | Electrophotographic photosensitive member and image forming apparatus |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114539518A (en) * | 2022-02-22 | 2022-05-27 | 苏州理硕科技有限公司 | Polymer, photoresist layer and photoetching process |
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| CN107643658B (en) | 2020-09-01 |
| JP2018013574A (en) | 2018-01-25 |
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