KR100644631B1 - Organophotoreceptor containing silicon based additive and electrophotographic imaging apparatus employing the organophotoreceptor - Google Patents

Abstract

The present invention relates to an organophotoreceptor, and an electrophotographic image forming apparatus employing the same. More particularly, the present invention relates to an organic photoconductor having a silicon-based additive added to improve solvent resistance of a monolayer photosensitive member and an electrophotographic image forming apparatus employing the same. .

Description

Organophotoreceptor containing silicon based additive and electrophotographic imaging apparatus employing the organophotoreceptor}

1 is a schematic diagram of an image forming apparatus, an electrophotographic drum, and an electrophotographic cartridge according to an embodiment of the present invention.

2 shows the UV-visible spectrum of the compound of formula 2 according to the present invention.

3 shows the UV-visible spectrum of the compound of formula 3 according to the present invention.

Figure 4 shows the UV-visible spectrum of the immersion liquid collected after the monolayer type OPC drum was prepared and left for a long time in a Norpar 12 solvent.

Figure 5 shows the absorbance results at the maximum absorption wavelength of the immersion liquid obtained by immersing 1 week / 2 weeks after the monolayer type OPC drum was prepared by varying the amount of the compound of formula 2 according to the present invention.

Figure 6 shows the absorbance results at the maximum absorption wavelength of the immersion liquid obtained by dipping 1 week / 2 weeks after the monolayer type OPC drum was prepared by varying the amount of the compound of formula 3 according to the present invention.

7 shows deposition results when the compounds of Formulas 2 and 3 are used as additives.

<Description of Major Symbols in Drawing>

21: electrophotographic cartridge 28: electrophotographic drum

30: electrophotographic image forming apparatus

The present invention relates to an organophotoreceptor, and an electrophotographic image forming apparatus employing the same. More particularly, the present invention relates to an organic photoconductor having a silicon-based additive added to improve solvent resistance of a monolayer photosensitive member and an electrophotographic image forming apparatus employing the same. .

In electrophotographic methods such as laser printers and copiers, an organophotoreceptor in the form of a plate, disk, sheet, belt, drum, etc. having a photosensitive layer on a conductive support is first charged uniformly and electrostatically on the surface of the photosensitive layer. And an image is formed by exposing the charged surface to a light pattern. Exposure selectively dissipates the charge in the irradiated region where light impinges on the surface, thereby forming a pattern of charged and non-charged regions, a so-called latent image. Next, a liquid or dry toner is provided to an adjacent portion of the latent image, and toner droplets or particles are attached to an adjacent portion of either of the charged or uncharged regions to form a toner image on the surface of the photosensitive layer. Form. The resulting toner image can be transferred to a suitable final or intermediate receiving surface such as paper, or the photosensitive layer can function as the final receptor for the image.

Organic photoconductor (OPC) drums are largely divided into two types. The first type is a laminate type charge generation layer including a binder resin and a charge generating material (CGM), and a charge including the binder resin and a charge transport material (mainly a hole transporting material (HTM)). It has a bilayer structure of a transport layer, and is generally used for manufacture of the (-) type organophotoreceptor. The second type is a single-layered structure in which a binder resin, a charge generating material, a hole transporting material, and an electron transporting material (ETM) are all included in one layer. Used for

The advantage of the (+) type single layer organophotoreceptor is that less harmful ozone is generated and the manufacturing cost is low since it is a single photosensitive layer. Among the materials constituting the (+) type single layer organophotoreceptor, the most important material is an electron transport material. The reason is that since the electron transporting capacity of the electron transporting material currently used is generally 100 times smaller than the hole transporting capacity of the hole transporting material, the performance of the single layer organophotoreceptor depends on the electron transporting capacity of the electron transporting material.

The electron transport ability of the electron transport material is greatly influenced by the solubility of the electron transport material molecules in the organic solvent and compatibility with the polymer binder resin. In particular, a liquid tomographic photosensitive member having a high resistance to a solvent that is a carrier of a liquid toner is desired.

Accordingly, an object of the present invention is to provide an organic photoconductor having a high resistance to a paraffin solvent, which is a carrier of a liquid toner, as a first object of the present invention.

A second object of the present invention is to provide an electrophotographic image forming apparatus, an electrophotographic cartridge, an electrophotographic drum and the like employing the organophotoreceptor.

One embodiment of the present invention to achieve the first object,

An organophotoreceptor comprising a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer is

It provides an organophotoreceptor comprising the compound of formula (I):

Food,

R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and each independently hydrogen, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon group having 1 to 20 carbon atoms An alkoxy group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;

m represents a number from 1 to 100,000;

n represents a number from 0 to 100,000.

According to an embodiment of the present invention, in the compound of Formula 1, R ₁ and R ₂ may be the same or different, each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, R ₃ is 6 carbon atoms To 15 substituted or unsubstituted aryl group, R ₄ represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, m represents a number of 1 to 100,000, n represents a number of 0 to 100,000.

According to an embodiment of the present invention, in the compound of Formula 1, R ₁ and R ₂ represent a methyl group, m represents a number from 1 to 100,000, n represents a number from zero.

According to an embodiment of the present invention, in the compound of Formula 1, R ₁ , R ₂ and R ₄ each represent a methyl group, R ₃ represents a phenyl group, m represents a number of 1 to 100,000, n is 1 to 100,000 Indicates the number of.

Another embodiment of the present invention to achieve the second object,

An electrophotographic image forming apparatus comprising an organophotoreceptor,

The organophotoreceptor is an organophotoreceptor including a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer comprises the compound of formula (1).

Another embodiment of the present invention to achieve the second object,

An organic photoconductor comprising a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer comprises a compound of Formula 1; And

And a charging device for charging the organophotoreceptor, a developing device for developing an electrostatic latent image formed on the organophotoreceptor, and a cleaning device for cleaning the surface of the organophotoreceptor.

An electrophotographic cartridge is provided which can be attached to and detachable from an image forming apparatus.

Another embodiment of the present invention to achieve the second object,

A drum that can be attached to the image forming apparatus and detachable from the image forming apparatus; And an organophotoreceptor disposed on the drum,

The organophotoreceptor is an organophotoreceptor including a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer comprises an electrophotographic drum, characterized in that the compound of formula (1).

Another embodiment of the present invention to achieve the second object,

A photoconductor unit comprising a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer comprises a compound of Formula 1;

A charging device for charging the photoreceptor unit;

An imaging light irradiation apparatus for irradiating said charged photosensitive member unit with imagewise light to form an electrostatic latent image on said photosensitive member unit;

A developing unit for developing the electrostatic latent image with toner to form a toner image on the photosensitive unit; And

An image forming apparatus comprising a transfer apparatus for transferring the toner image onto a container.

Hereinafter, an organophotoreceptor according to the present invention and an electrophotographic image forming apparatus employing the same will be described in detail.

The compound according to the present invention represented by the following Chemical Formula 1 may be added to the photosensitive layer in a small amount to be successfully used in the preparation of a wet monolayer organophotoreceptor having a high resistance to a solvent, particularly a paraffin solvent, which is a carrier of a liquid toner.

<Formula 1>

Food,

R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and each independently hydrogen, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon group having 1 to 20 carbon atoms An alkoxy group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;

m represents a number from 1 to 100,000;

n represents a number from 0 to 100,000.

In Chemical Formula 1, a halogen group represents fluorine, chlorine, bromine, iodine and the like.

In Formula 1, the alkyl group is a straight or branched alkyl group having 1 to 20 carbon atoms, preferably a straight or branched alkyl group having 1 to 10 carbon atoms. Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, 1,2-dimethyl-propyl, 2-ethyl-hexyl, and the like. Can be mentioned. The alkyl group may be substituted with a halogen atom such as fluorine, chlorine, bromine or iodine.

The alkoxy group in the general formula (1) is a straight or branched alkoxy group having 1 to 20 carbon atoms, preferably a straight or branched alkoxy group having 1 to 10 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy group, propoxy group and the like. The alkoxy group may be substituted with a halogen atom such as fluorine, chlorine, bromine or iodine.

In the general formula (1), the aralkyl group is a straight or branched aralkyl group having 7 to 30 carbon atoms, preferably a straight or branched aralkyl group having 7 to 15 carbon atoms. Specific examples of the aralkyl group include benzyl group, methylbenzyl group, phenylethyl group, naphthylmethyl group, naphthylethyl group and the like. The aralkyl group may be substituted with a halogen atom such as fluorine, chlorine, bromine or iodine, an alkyl group, an alkoxy group, a nitro group, a hydroxy group, a sulfonic acid group, or the like.

In Formula 1, an aryl group refers to an aromatic ring having 6 to 30 carbon atoms. Examples thereof include phenyl, tolyl, xylyl, biphenyl, o-terphenyl, naphthyl, anthracenyl, phenanthrenyl and the like. The aryl group may be substituted with an alkyl group, an alkoxy group, a nitro group, a hydroxy group, a sulfonic acid group or a halogen atom.

Preferably, in the compound of Formula 1, R ₁ and R ₂ may be the same or different, each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, R ₃ is a substituted or substituted with 6 to 15 carbon atoms or An unsubstituted aryl group, R ₄ represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, m represents a number from 1 to 100,000, and n represents a number from 0 to 100,000.

According to one embodiment of the present invention, the compound of Formula 1 may be added in an amount of about 0.01 to 0.5% by weight based on the total component content of the photosensitive layer.

More preferred examples of the compound of Formula 1 include a compound of Formula 2 or a compound of Formula 3 below:

Wherein m represents a number from 1 to 100,000.

Wherein m and n represent numbers from 1 to 100,000.

The compound may be purchased from Shin-Etsu Co., Ltd., Dow Corning Co., Ltd. as a commercially available material. More specifically, Shin-Etsu Co., Ltd. product names KF96, KF965, KF968 etc. are mentioned, for example, Dow Corning's model name DC510, etc. are mentioned.

Hereinafter, an electrophotographic image forming apparatus employing an organophotoreceptor according to the present invention including the compound of Chemical Formula 1, an electrophotographic drum, an electrophotographic cartridge, and the like will be described. First, the electrophotographic image forming apparatus will be described first.

1 is a schematic diagram of an image forming apparatus 30, an electrophotographic drum 28, and an electrophotographic cartridge 21 according to an embodiment of the present invention. The electrophotographic cartridge 21 typically includes an organophotoreceptor 29, at least one charging device 25 for charging the organophotoreceptor 29, a developing device 24 for developing an electrostatic latent image formed on the organophotoreceptor 29, And a cleaning device 26 for cleaning the surface of the organophotoreceptor 29. The electrophotographic cartridge 21 may be attached to the image forming apparatus 30 and may be detached from the image forming apparatus 30.

The organophotoreceptor drums 28, 29 of the image forming apparatus 30 may generally be attached to the electrophotographic apparatus 30 and detachable from the electrophotographic apparatus 30, on which the organophotoreceptor 29 may be attached. Disposed drum 28.

In general, the image forming apparatus 30 includes a photosensitive unit (for example, organic photosensitive drums 28 and 29), a charging device 25 for charging the photosensitive unit, and an electrostatic latent image on the photosensitive unit. An imaging light irradiation apparatus 22 for irradiating the charged photosensitive unit with imagewise light, and a developing unit for developing an electrostatic latent image with toner to form a toner image on the photosensitive unit (24), and a transfer device 27 for transferring the toner image onto a container such as paper P, wherein the photoconductor unit includes an organophotoreceptor 29 to be described in detail below. The charging device 25 may receive a voltage as a charging unit, and may also contact and charge the organophotoreceptor. The image forming apparatus 30 may also include a preexposure unit 23 for erasing residual charge on the surface of the organophotoreceptor in preparation for the next cycle.

The photoconductor including the compound of Formula 1 according to the present invention may be integrated into an electrophotographic image forming apparatus such as a laser printer, a copier, a fax machine.

Hereinafter, an organophotoreceptor according to the present invention including the compound of Formula 1 employed in the electrophotographic image forming apparatus and the like described in FIG. 1 will be described in detail.

The organophotoreceptor according to the present invention has a structure including a photosensitive layer formed on a conductive support. Examples of the conductive support include drums and belts made of metals, conductive polymers, and the like. Examples of the metal include aluminum and stainless steel. As said conductive polymer, what disperse | distributed electroconductive substances, such as conductive carbon, tin oxide, indium oxide, to polyester resin, polycarbonate resin, polyamide resin, polyimide resin, and these copolymers is mentioned.

The photosensitive layer may be a stacked type in which a charge generating layer and a charge transport layer are separately formed, or may be a single layer type having both functions of charge generation and charge transport in one layer.

The compound of formula 1 according to the present invention is added to the photosensitive layer in a small amount to form an organophotoreceptor having a strong resistance to the paraffin solvent that is the carrier of the liquid toner. It is believed that the compound of Formula 1 serves to make the coating state of the organic photosensitive layer uniform as a silicon compound. This uniform coating state can increase the solvent resistance to the organic solvent. When added, the stacked photosensitive layer is included in the charge transport layer or the charge generating layer, and in the case of the single layer photosensitive layer, it is included in one layer together with the charge generating material.

Addition amount of the compound of Formula 1 is added in an amount of 0.01 to 0.5% by weight based on the total content of the photosensitive layer. If the amount is more than 0.5% by weight, compound 1 is mixed with a paraffinic solvent, which is a wet carrier, so that solvent resistance is poor. If the amount is less than 0.01% by weight, the coating state of the photosensitive layer is deteriorated and solvent resistance is poor. There is a problem of falling, which is undesirable.

As a charge generating material used for a photosensitive layer, a phthalocyanine pigment, an azo pigment, a quinone pigment, a perylene pigment, an indigo pigment, a bisbenzoimidazole pigment, a quinacridone pigment, an azulenium dye, Organic materials such as squarylium dyes, pyrylium dyes, triarylmethane dyes, and cyanine dyes, amorphous silicon, amorphous selenium, trigonal selenium, tellurium, selenium-tel And inorganic materials such as rulium alloy, cadmium sulfide, antimony sulfide, and zinc sulfide. The charge generating materials used in the photosensitive layer are not limited thereto, and they may be used alone, but two or more kinds of charge generating materials may be mixed and used.

In the case of the laminated photoconductor, the charge generating material is dispersed in a solvent together with a binder resin to form a charge generating layer by forming a film by immersion coating, ring coating, roll coating, spray coating or the like. The thickness of the charge generating layer is usually preferably set within the range of about 0.1 탆 to about 1 탆. If the thickness is less than 0.1 μm, there is a problem that the sensitivity is insufficient, if more than 1 μm there is a problem that the charging ability and sensitivity is lowered.

A charge transport layer is formed on the charge generating layer of the stacked photosensitive layer, but a charge generating layer may be provided on the charge transport layer by reversing the layer structure. In order to form the charge transport layer, a method of applying a solution in which the charge transport material and the binder resin are dissolved in a solvent may be used. As a coating method, immersion coating, ring coating, roll coating, spray coating, etc. are mentioned similarly to the case of the photosensitive layer. The thickness of the charge transport layer is usually set within the range of about 5 μm to about 50 μm. If the thickness is less than 5 μm, there is a problem of poor chargeability. If the thickness is more than 50 μm, there is a problem such as a decrease in response speed and deterioration of image quality.

In the case of a single-layer photosensitive member, the photosensitive layer is obtained by dispersing and applying the charge generating material in a solvent together with a binder resin, a charge transporting material and the like. It is preferable that the thickness of the photosensitive layer is usually in the range of about 5 μm to about 50 μm. In this case, although the naphthalene tetracarboxylic acid diimide derivative of General formula (1) of this invention is used as a charge transport material, it is also preferable to use another charge transport material together. As the charge transporting material, there are a hole transporting material and an electron transporting material, but in the case of a single-layer photosensitive member, it is preferable to use the hole transporting material in combination.

As the charge transport material usable in the electrophotographic photosensitive member of the present invention, any of a hole transport material and an electron transport material can be used.

As a hole transporting material which can be used for the photosensitive layer, for example, pyrene-based, carbazole-based, hydrazone-based, oxazole-based, oxadiazole-based, pyrazoline-based, arylamine-based, arylmethane-based, benzidine-based, thiazole-based, styryl-based, etc. And nitrogen-containing cyclic compounds and condensed polycyclic compounds.

Examples of the electron transporting substance include benzoquinone series, cyanoethylene series, cyanoquinomimethane series, fluorenone series, xanthone series, phenanthraquinone series, phthalic anhydride series, thiopyran series, naphthalene series, diphenoquinone series, Electron-absorbing low molecular weight compounds, such as a stilbenquinone series, are mentioned.

The charge transport material used for the electrophotographic photoconductor according to the present invention is not limited to the above-mentioned one, and can be used alone or in combination of two or more kinds.

As a solvent for forming the coating liquid for photosensitive layer formation, organic solvents, such as alcohol, ketone, amide, ether, ester, sulfone, aromatic, aliphatic halogenated hydrocarbon, are mentioned, for example. Although the dip coating method is preferable as a photosensitive layer coating method, ring coating, roll coating, spray coating, etc. can also be used.

As binder resin for forming the coating liquid for photosensitive layer formation, for example, polycarbonate, polyester, methacryl resin, acrylic resin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinylacetate, silicone resin, silicone- Alkyd Resin, Styrene-Alkyd Resin, Poly-N-Vinyl Carbazole, Phenoxy Resin, Epoxy Resin, Polyvinyl Butyral, Polyvinyl Acetal, Polyvinyl Formal, Polysulfone, Polyvinyl Alcohol, Ethyl Cellulose, Phenolic Resin , Polyamide, carboxymethyl cellulose, polyurethane, and the like, but are not limited to these. These high molecular polymers may be used alone or in combination of two or more kinds thereof.

The content of the charge transport material in the photosensitive layer is preferably in the range of 10 to 60% by weight based on the total weight of the photosensitive layer. If it is less than 10% by weight, the charge transporting capacity is insufficient, so the sensitivity is insufficient and the residual potential tends to be large, and if it is more than 60% by weight, the content of the resin in the photosensitive layer decreases and the mechanical strength tends to decrease. This is undesirable.

In the present invention, a conductive layer may be further formed between the support and the photosensitive layer. The conductive layer is obtained by dispersing a conductive powder such as carbon black, graphite, metal powder, or metal oxide powder in a solvent, and then applying the resulting dispersion onto a support and drying. The thickness of the conductive layer is preferably in the range of about 5 to about 50 μm.

In addition, an intermediate layer may be provided between the support and the photosensitive layer or between the conductive layer and the photosensitive layer for the purpose of improving adhesion or preventing charge injection from the support. Examples of such intermediate layers include anodized layers of aluminum; Resin dispersion layers of metal oxide powders such as titanium oxide and tin oxide; Although resin layers, such as polyvinyl alcohol, casein, ethyl cellulose, gelatin, a phenol resin, and a polyamide, are mentioned, It is not limited to these. The thickness of the intermediate layer is preferably in the range of about 0.05 to about 5 μm.

In addition to the binder resin, additives such as plasticizers, leveling agents, dispersion stabilizers, antioxidants and light stabilizers may be used.

As antioxidant, antioxidant, such as a phenol type, a sulfur type, phosphorus type, an amine compound, is mentioned, for example. As a light stabilizer, a benzotriazole type compound, a benzophenone type compound, a hindered amine type compound, etc. are mentioned, for example.

In addition, the organophotoreceptor of the present invention may further include a surface protective layer as necessary.

Hereinafter, examples of the present invention will be described, but for the purpose of illustration, the scope of the present invention is not limited thereto.

Example 1 (additive amount of the formula 2: 0.005 wt%)

615 parts by weight of an electron transporting material of Formula 4, 90 parts by weight of a charge generating material (X type metal free phthalocyanine) of Formula 5, 480 parts by weight of a hole transporting material of Formula 6, 15 parts by weight of an electron accepting material of Formula 7 , 1800 parts by weight of the binder resin of Formula 8, additive of Formula 2 (available from Shin-Etsu Co., Ltd., viscosity 100 CST, product name: KF96) 0.15 parts by weight, 8680 parts by weight of methylene chloride, 1,1,2-trichloro 3720 parts by weight of ethane are sand milled for 2 hours and then dispersed by ultrasonic wave. The solution thus obtained was coated on anodized aluminum drum, and dried at 110 degrees for 1 hour to prepare an OPC drum.

<Formula 2>

Wherein m represents a number from 1 to 100,000.

Example 2 (Additive Additive: 0.01 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 2 was 0.3 parts by weight.

Example 3 (Additive Additive: 0.02 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 2 was 0.6 parts by weight.

Example 4 (Additive Additive: 0.03 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 2 was 0.9 parts by weight.

Example 5 (Additive Additive: 0.05 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive of Formula 2 was 1.5 parts by weight.

Example 6 (Additive amount: 0.1 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 2 was 3 parts by weight.

Example 7 (Additive Addition: 0.2 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive of Formula 2 was 6 parts by weight.

Example 8 (additive amount: 0.5 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 2 was 15.1 parts by weight.

Example 9 (addition amount of additives: 1 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the addition amount of the additive of Formula 2 was 30.3 parts by weight.

Example 10 (Additive Addition: 2 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive of Formula 2 was 61.2 parts by weight.

Example 11 (addition amount of additives: 0.005 wt%)

615 parts by weight of the electron transport material of Formula 4, 90 parts by weight of the charge generating material (X type metal free phthalocyanine) of Formula 5, 480 parts by weight of the hole transport material of Formula 6, 15 parts by weight of the electron accepting material of Formula 7 , 1800 parts by weight of the binder resin of Formula 8, the additive of Formula 3 (available from Dow Corning Corporation, viscosity 100CST, product name: DC510) 0.15 parts by weight, methylene chloride 8680 parts, 1,1,2-trichloroethane 3720 parts by weight of sand mill for 2 hours and then dispersed by ultrasonic wave. The solution thus obtained was coated on anodized aluminum drum, and dried at 110 degrees for 1 hour to prepare an OPC drum.

<Formula 3>

Wherein m and n represent numbers from 1 to 100,000.

Example 12 (Additive Addition: 0.01 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the addition amount of the additive of Formula 3 was 0.3 parts by weight.

Example 13 (Additive Additive: 0.02 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 3 was 0.6 parts by weight.

Example 14 (Additive Additive: 0.03 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 3 was 0.9 parts by weight.

Example 15 (Additive Additive: 0.05 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive of Formula 3 was 1.5 parts by weight.

Example 16 (Additive Additive: 0.1 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 3 was 3 parts by weight.

Example 17 (Additive Additive: 0.2 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 3 was 6 parts by weight.

Example 18 (Additive Additive: 0.5 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive represented by Chemical Formula 3 was 15.1 parts by weight.

Example 19 (Additive Addition: 1 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the addition amount of the additive of Formula 3 was 30.3 parts by weight.

Example 20 (Additive Addition: 2 wt%)

An OPC drum was manufactured in the same manner as in Example 1, except that the amount of the additive of Formula 3 was 61.2 parts by weight.

Comparative Example 1 (without additive)

615 parts by weight of the electron transport material of Formula 4, 90 parts by weight of the charge generating material (X type metal free phthalocyanine) of Formula 5, 480 parts by weight of the hole transport material of Formula 6, 15 parts by weight of the electron accepting material of Formula 7 , 1800 parts by weight of the binder resin of Formula 8, 8680 parts by weight of methylene chloride, 3720 parts by weight of 1,1,2-trichloroethane are sand milled for 2 hours and then dispersed by ultrasonic wave. The solution thus obtained was coated on anodized aluminum drum, and dried at 110 degrees for 1 hour to prepare an OPC drum.

The content of the additives used in Examples 1 to 20 and Comparative Example 1 and the thickness of the photosensitive layer are shown in Table 1 below.

division Additive amount d (um) Example 1 0.005% by weight of compound of formula 2 12.0 Example 2 0.01 wt% of a compound of Formula 2 12.5 Example 3 0.02% by weight of compound of formula 2 14.5 Example 4 0.03% by weight of compound of formula 2 16.7 Example 5 0.05% by weight of compound of formula 2 17.4 Example 6 0.1 wt% of a compound of Formula 2 16.5 Example 7 0.2 wt% of a compound of Formula 2 15.0 Example 8 0.5% by weight of compound of formula 2 12.5 Example 9 1% by weight of compound of formula 2 13.0 Example 10 2% by weight of compound of formula 2 11.0 Example 11 0.005% by weight of compound of formula 3 13.0 Example 12 0.01% by weight of compound of Formula 3 15.0 Example 13 0.02% by weight of compound of formula 3 15.0 Example 14 0.03% by weight of compound of formula 3 17.0 Example 15 0.05 wt% of the compound of formula 3 16.5 Example 16 0.1 wt% of a compound of Formula 3 14.5 Example 17 0.2 wt% of a compound of Formula 3 13.0 Example 18 0.5% by weight of compound of formula 3 12.0 Example 19 1% by weight of compound of formula 3 11.0 Example 20 2% by weight of compound of formula 3 12.0 Comparative Example 1 No additives -

Solvent resistance evaluation test

The monolayer OPC drums obtained in Examples 1 to 20 and Comparative Example 1 were immersed for 1 week to 2 weeks in 300 ml Norpar12 solvent, and then the immersion liquid (Norpar12) was collected and an electron transport material and a hole using a UV-Vis spectrometer. The solvent resistance was evaluated by measuring how much the transport material dissolved.

2 and 3 are UV-visible spectral results of the compounds of Formulas 2 and 3, respectively, and FIG. 4 shows a immersion liquid (Norpar12) after immersion in Norpar12 solvent for 1 week to 2 weeks after the production of a monolayer OPC drum. It collects and shows the result of having measured the UV-visible-light spectrum.

It can be seen that the peaks of the compounds of the formulas (2) and (3) overlap when the monolayer type OPC drum is deposited. Therefore, it can be seen that the compounds of Formulas 2 and 3 melt together in Norpar12.

5 shows the results of absorbance at the maximum absorption wavelength after the monolayer type OPC drum was prepared by varying the amount of the compound of Formula 2 added as an additive (Examples 1 to 10) for 1 week / 2 weeks.

As a result of adding 0.02 to 0.2% by weight of the compound of Formula 2 as an additive, it can be seen that the solvent resistance is inferior to Comparative Example 1 (leftmost in FIG. 4) without any additives. The reason is that the additive itself mixes well with Norpar12, the carrier of the liquid toner, so it can be seen that it is counterproductive when added too much.

Figure 6 shows the results of absorbance at the maximum absorption wavelength after the production of a monolayer type OPC drum with different amounts of addition when the compound of formula 3 is added as an additive (Examples 11 to 20).

As a result of adding 0.01 to 0.2% by weight of the compound of Formula 3 as an additive, it can be seen that the solvent resistance is superior to that of Comparative Example 1 (leftmost in FIG. 6) without any additives.

However, even when the compound of Formula 3 is used as an additive, when the content of the additive is too large (0.5 wt% or more), it can be seen that solvent resistance is inferior to Comparative Example 1 in which no additive is added.

7 is a comparison of the results of two weeks deposition of the compounds of formulas (2) and (3) shows that the compound of formula 3 shows relatively better solvent resistance than the compound of formula (2).

As described above, when the compound of Chemical Formula 1 according to the present invention is used as an additive in an organic photosensitive layer, resistance to paraffinic solvents used as wet carriers becomes stronger, and thus may be more usefully used. If the solvent resistance of the photoreceptor is poor, the performance of the organic photoreceptor is improved due to the excellent solvent resistance because the performance of the photoreceptor is degraded as the hole transporting material and the electron transporting material in the photosensitive layer melt out as time passes.

While several embodiments of the present invention have been disclosed and described, those skilled in the art will understand that changes may be made to such embodiments without departing from the spirit and spirit of the invention. Therefore, the scope of the present invention is defined by the following claims and their equivalents.

Claims (5)

An organophotoreceptor comprising a conductive support and a photosensitive layer formed on the conductive support, wherein the photosensitive layer comprises a compound of Formula 1 in a ratio of 0.01 to 0.5% by weight relative to the total content of the photosensitive layer. Organic photoreceptors for printers: <Formula 1>

Food, R ₁ , R ₂ , R ₃ and R ₄ may be the same or different, and each independently hydrogen, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, an aralkyl group having 7 to 30 carbon atoms And an aryl group having 6 to 30 carbon atoms; m represents a number from 1 to 100,000; n represents a number from 0 to 100,000. The organic photoconductor according to claim 1, wherein the compound of Formula 1 is a compound of Formula 2: <Formula 2>

Wherein m represents a number from 1 to 100,000. The organophotoreceptor of claim 1 wherein the compound of Formula 1 is a compound of Formula 3: <Formula 3>

Wherein m and n represent numbers from 1 to 100,000. An electrophotographic image forming apparatus comprising the organophotoreceptor according to any one of claims 1 to 3. An organophotoreceptor according to any one of claims 1 to 3; And And a charging device for charging the organophotoreceptor, a developing device for developing an electrostatic latent image formed on the organophotoreceptor, and a cleaning device for cleaning the surface of the organophotoreceptor. An electrophotographic cartridge, which can be attached to and detachable from an image forming apparatus.

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