JP3100437B2 - Phenanthrene derivative and photoreceptor using the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phenanthrene derivative suitable as a charge transporting material in a photoreceptor used for an electrostatic copying machine, a laser beam printer or the like, and a photoreceptor using the same.

[0002]

2. Description of the Related Art In recent years, as a photoconductor in an image forming apparatus such as a copying machine, an organic photoconductor excellent in workability and economy and having a high degree of freedom in functional design has been widely used. When a copy image is formed using a photoreceptor, the Carlson process is widely used. The Carlson process includes a charging process for uniformly charging a photoconductor by corona discharge, an exposure process for exposing a charged image to a document image to form an electrostatic latent image corresponding to the document image, Developing with a developer containing toner, a developing step of forming a toner image, a transfer step of transferring the toner image to paper or the like, a fixing step of fixing the transferred toner image, and after the transfer step,
A cleaning step of removing toner remaining on the photoconductor. In the Carlson process, in order to form a high-quality image, it is required that the photosensitive member has excellent charging characteristics and photosensitive characteristics, and that the residual potential after exposure is low.

[0003] Conventionally, inorganic photoconductors such as selenium and cadmium sulfide have been known as photoreceptor materials, but they have the disadvantage of being toxic and of high production cost. Therefore, so-called organic photoreceptors using various organic substances instead of these inorganic substances have been proposed. Such an organic photoreceptor has a photosensitive layer composed of a charge generating material that generates charges by exposure and a charge transporting material having a function of transporting the generated charges.

In order to satisfy various conditions desired for such an organic photoreceptor, it is necessary to appropriately select these charge generating materials and charge transporting materials. Various organic compounds such as carbazole compounds, oxadiazole compounds, pyrazoline compounds, hydrazone compounds, stilbene compounds, and phenylenediamine compounds have been proposed as charge transport materials.

[0005]

However, all of the above-mentioned conventional charge transport materials have insufficient charge transport ability, poor light stability, or a binder resin constituting the photosensitive layer. The charge transport material has poor sensitivity and durability.Therefore, there is a problem that the photoreceptor using this charge transport material has insufficient sensitivity and durability. Was.

An object of the present invention is to provide a compound which is excellent in charge transporting ability and light stability and is suitable as a charge transporting material, and a photoreceptor which uses the compound and has high sensitivity and excellent durability. .

[0007]

In order to solve the above-mentioned problems, a phenanthrene derivative of the present invention has a general formula (I):

[0008]

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[In the formula, R ¹ , R ² , R ³ and R ⁴ are the same or different and represent an alkyl group, an aryl group or a heterocyclic group, and R ⁵ and R ⁶ are the same or different and represent a hydrogen atom or a halogen atom. , An alkyl group or an aryl group. n is 1
Shows an integer of ~ 4. ]. Further, a photoreceptor of the present invention for achieving the above object is characterized in that a photosensitive layer containing a phenanthrene derivative represented by the above general formula (I) is provided on a conductive substrate.

The phenanthrene derivative represented by the above general formula (I) has a high charge transporting ability and excellent light stability because the structure of phenanthrene known as a quencher is introduced into the molecule. . Therefore, the photosensitive layer containing the phenanthrene derivative as a charge transport material has high sensitivity and excellent durability.

As described above, the reason why the phenanthrene derivative represented by the general formula (I) has high sensitivity and photostability is that the phenanthrene moiety, the double bond of the group bonded to the phenanthrene moiety and the nitrogen Π formed by
Because the electron conjugated system has a larger spread than that of the conventional charge transport material, the planarization of the molecular structure of the compound is further promoted, and the intermolecular interaction due to the overlapping between the molecules is strengthened. Presumed.

Examples of the alkyl group include lower alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl and hexyl. Can be Examples of the aryl group include a phenyl group, an o-terphenyl group,
Examples include a naphthyl group, an anthryl group and a phenanthryl group.

The heterocyclic group includes, for example, thienyl group, pyrrolyl group, pyrrolidinyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, 2H-imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, pyranyl group , A pyridyl group, a piperidyl group, a piperidino group, a 3-morpholinyl group, a morpholino group, and a thiazolyl group. Also,
It may be a heterocyclic group condensed with an aromatic ring.

Specific examples of the phenanthrene derivative represented by the general formula (I) include the following.

[0015]

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[0016]

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[0017]

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[0018]

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The phenanthrene derivative of the present invention can be synthesized by various methods, for example, by the method shown in the following reaction formula.

[0020]

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[0021]

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Wherein R ^{1 to} R ⁶ and n are the same as described above. That is, as shown in the above reaction formula, the formula (a)
A sodium amide represented by the formula (b) is reacted with a 9-bromo-10-formylphenanthrene derivative represented by the formula in the presence of a solvent to obtain an aldehyde compound represented by the formula (c). Next, the compound (c) is reacted with a hydrazine-based compound represented by the formula (d) in the presence of a basic substance and a solvent to give a phenanthrene derivative of the present invention represented by the formula (I). Is obtained.

The sodium amide represented by the formula (b) has the formula
The hydrazine compound represented by the formula (d), which is used in an equimolar amount to the 9-bromo-10-formylphenanthrene derivative represented by the formula (d), is an aldehyde compound represented by the formula (c): Used in equimolar amounts to Examples of the basic substance include alcoholates such as sodium methylate, sodium ethylate, and potassium tert-butylate;
Sodium acetate, sodium hydroxide, potassium hydroxide,
Examples thereof include sodium amide and sodium hydride, and the amount of use is 0.5 equivalent to the aldehyde compound represented by the formula (c).

The former 9-bromo-10- represented by (a)
As the solvent used in the reaction of the formylphenanthrene derivative with the sodium amide represented by the formula (b),
Benzene, N, N'-dimethylformamide, dimethylsulfoxide and the like can be mentioned. Solvents used in the reaction between the latter aldehyde compound represented by the formula (c) and the sodium amide represented by the formula (d) include methanol, ethanol, isopropyl alcohol, methyl cellosolve, and ethyl cellosolve. Alcohols, glycols such as ethylene glycol and propylene glycol,
Ethers such as dioxane and tetrahydrofuran, N,
N'-dimethylformamide, dimethyl sulfoxide and the like can be mentioned, among which N, N'-dimethylformamide is preferably used.

The amount of the solvent used is not particularly limited in any case, and it suffices that it is 1 to 20 times the total amount of the compounds used in the reaction. The reaction temperature of the former reaction is 50 to
Preferably it is in the range of 80 ° C. On the other hand, the latter reaction proceeds sufficiently at room temperature without heating, but may be heated to shorten the reaction time. The reaction temperature is between 10 and
It is preferably in the range of 110 ° C, and 20 to 70 ° C
Is more preferably within the range.

The degree of progress of the reaction can be known by analyzing the reaction solution by thin layer chromatography, high performance liquid chromatography or the like. After completion of the reaction, the desired product can be taken out by a usual method such as filtration or solvent extraction, and if necessary, can be purified by a method such as recrystallization or column chromatography.

The 9-bromo-10 represented by the formula (a)
-Formylphenanthrene derivatives are, for example, 9,10
-Dibromophenanthrene derivative in the presence of a solvent,
Reaction with 0.5-fold molar amount of methyl iodide gave a 9-bromo-10-methylphenanthrene derivative.
By reacting the bromo-10-methylphenanthrene derivative with potassium dichromate in the presence of a solvent,
It can be easily manufactured. Benzene, toluene, xylene and the like are suitably used as the solvent used in these reactions, and the reaction temperature is preferably in the range of 50 to 80 ° C.

The photoreceptor of the present invention is provided with a photosensitive layer containing one or more of the phenanthrene derivatives represented by the general formula (I) as a charge transport material. The photosensitive layer includes a so-called single layer type and a laminated type, and the present invention can be applied to any of these. To obtain a single-layer photoreceptor, a photosensitive layer containing a compound represented by the general formula (I) as a charge transporting material, a charge generating material, a binder resin, and the like is coated by a means such as coating. May be formed on the conductive substrate.

Further, in order to obtain a laminated photoreceptor, a charge generation layer containing a charge generation material is formed on a conductive substrate by means such as vapor deposition or coating.
What is necessary is just to form a charge transport layer containing the compound represented by the general formula (I) and a binder resin. Also, contrary to the above,
A charge transport layer may be formed on a conductive substrate, and then a charge generation layer may be formed. Further, in the above-mentioned laminated photosensitive layer, the charge generation layer may contain a charge transport material.

Examples of the charge generating material include selenium, selenium-tellurium, selenium-arsenic, amorphous silicon, pyrylium salts, azo compounds, disazo compounds, phthalocyanine compounds, anthanthrone compounds, and perylene compounds which have been conventionally used. Examples include compounds, indigo compounds, triphenylmethane compounds, sulene compounds, toluidine compounds, pyrazoline compounds, perylene compounds, quinacridone compounds, and pyrrolopyrrole compounds. These charge generation materials can be used alone or in combination of two or more so as to have an absorption wavelength region in a desired region.

The phenanthrene derivative represented by the general formula (I), which is a charge transporting material, can be used alone or in combination with other conventionally known charge transporting materials. As a conventionally known charge transporting material, various electron withdrawing compounds and electron donating compounds can be used. Examples of the electron-withdrawing compound include diphenoquinone derivatives such as 2,6-dimethyl-2 ', 6'-ditert-dibutyldiphenoquinone, malononitrile, thiopyran-based compounds, tetracyanoethylene, and 2,4,8-triene. Examples thereof include nitrothioxanthone, 3,4,5,7-tetranitro-9-fluorenone, dinitrobenzene, dinitroanthracene, dinitroacridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride, and dibromomaleic anhydride.

As the electron donating compound, 2,5
Oxadiazole compounds such as -di (4-methylaminophenyl) and 1,3,4-oxadiazole; 9- (4
Styryl compounds such as -diethylaminostyryl) anthracene, carbazole compounds such as polyvinylcarbazole, pyrazoline compounds such as 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, hydrazone compounds, triphenylamine compounds, indole compounds Examples include compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, nitrogen-containing cyclic compounds such as triazole compounds, and condensed polycyclic compounds.

These charge transport materials are used alone or in combination of two or more. Note that when a charge transporting material having a film forming property such as polyvinyl carbazole is used,
The binder resin is not always necessary. As the binder resin,
Various resins can be used. For example, styrene polymers, styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, acrylic copolymers, styrene-acrylic acid copolymers, polyethylene, ethylene-vinyl acetate copolymer , Chlorinated polyethylene, polyvinyl chloride, polypropylene,
Thermoplastic resins such as vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, silicone resin, epoxy Resins, phenolic resins, urea resins, melamine resins, other crosslinkable thermosetting resins, and photocurable resins such as epoxy acrylate and urethane-acrylate. These binder resins can be used alone or in combination of two or more.

In each of the single-layer type and laminated type organic photosensitive layers,
A sensitizer, a fluorene compound, an antioxidant, a deterioration inhibitor such as an ultraviolet absorber, and an additive such as a plasticizer can be contained. In order to improve the sensitivity of the charge generation layer, a known sensitizer such as terphenyl, halonaphthoquinones, and acenaphthylene may be used in combination with the charge generation material.

In the laminate type photoreceptor, the charge generating material and the binder resin constituting the charge generating layer can be used in various ratios, but the ratio is based on 100 parts (parts by weight, hereinafter the same) of the binder resin. 5 to 500 parts of the charge generating material,
It is preferred to use 300 parts. The charge generation layer may have an appropriate thickness, but may have a thickness of 0.01 to 5
It is preferably formed to a thickness of about μm, especially about 0.1 to 3 μm.

The phenanthrene derivative (charge transporting material) represented by the above general formula (I) and the binder resin constituting the charge transporting layer can be used in various forms within a range that does not inhibit charge transport and a range that does not crystallize. Can be used in proportion,
In order that the charge generated in the charge generation layer by light irradiation can be easily transported, with respect to 100 parts of the binder resin, the general formula (I)
It is preferable to use the phenanthrene derivative represented by the formula in an amount of 10 to 500 parts, especially 25 to 200 parts. Also,
The thickness of the laminated photosensitive layer is 0.01 to 5 μm for the charge generation layer.
m, particularly preferably about 0.1 to 3 μm, and the charge transport layer is 2 to 100 μm, particularly 5 to 50 μm.
m.

In the case of a single-layer type photoreceptor, the binder resin 10
0.1 to 50 parts, especially 0.1 to 50 parts, of the charge generating material is used.
5 to 30 parts, and the phenanthrene derivative (charge transporting material) represented by the general formula (I) is 40 to 200 parts, particularly 50 to 50 parts.
Suitably 100 parts. The thickness of the single-layer type photosensitive layer is preferably 5 to 100 μm, particularly preferably about 10 to 50 μm.

In the case of a single-layer type photoreceptor, between a conductive substrate and a photosensitive layer, in the case of a laminated type photoreceptor, between a conductive substrate and a charge generating layer, A barrier layer may be formed between the photoconductor and the charge transport layer or between the charge generation layer and the charge transport layer as long as the properties of the photoconductor are not impaired. It may be formed.

Various conductive materials can be used as the conductive substrate on which the above layers are formed.
For example, simple metals such as aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, brass and the like, plastic materials on which the above metals are deposited or laminated, iodide Glass coated with aluminum, tin oxide, indium oxide or the like is exemplified.

The conductive substrate may be in the form of a sheet, a drum, or the like, as long as the substrate itself has conductivity or the surface of the substrate has conductivity. In addition, the conductive substrate preferably has sufficient mechanical strength when used. When each of the above layers is formed by a coating method, the above-described charge generation material, charge transport material,
A binder resin and the like, together with an appropriate solvent, are dispersed and mixed using a known method, for example, a roll mill, a ball mill, an attritor, a paint shaker, an ultrasonic disperser, or the like to prepare a coating solution. It may be applied and dried.

As the solvent for preparing the coating solution, various organic solvents can be used, for example, alcohols such as methanol, ethanol, isopropanol and butanol;
n-hexane, octane, aliphatic hydrocarbons such as cyclohexane, benzene, toluene, aromatic hydrocarbons such as xylene, dichloromethane, dichloroethane, carbon tetrachloride, halogenated hydrocarbons such as chlorobenzene, dimethyl ether, diethyl ether, tetrahydrofuran, Ethers such as ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone and cyclohexanone; esters such as ethyl acetate and methyl acetate; dimethyl formaldehyde, dimethyl formamide, dimethyl sulfoxide and the like. These solvents can be used alone or in combination of two or more.

Further, a surfactant, a leveling agent and the like may be used in order to improve the dispersibility and dyeing property of the charge transporting material and the charge generating material. Note that, as described above, the charge generation layer may be formed by depositing the charge generation material.

[0043]

The present invention will be described below in detail with reference to examples and comparative examples. Example 1 <Synthesis of phenanthrene derivative represented by the above formula (1)>
2.85 g of 9-bromo-10-formylphenanthrene in which R ⁵ and R ⁶ in the formula (a) are both hydrogen atoms, and sodium in which R ¹ and R ² in the formula (b) are both phenyl groups. 1.91 g of the amide was mixed with potassium dichromate 2.0
3 g together with 100 g of benzene, refluxed at 60 ° C. for 5 hours, and an aldehyde compound wherein R ¹ and R ² in the above formula (c) are both phenyl groups and R ⁵ and R ⁶ are both hydrogen atoms. 2.73 g (73% yield) were obtained.

Then, the aldehyde compound 1.87 was obtained.
g of the hydrazine-based compound in which both R ³ and R ⁴ in the above formula (d) are phenyl groups, and 0.9 g of sodium acetate.
Dissolved in 100 ml of benzene together with 41 g;
For 5 hours to obtain 2.21 g (yield 82%) of the phenanthrene derivative represented by the above formula (1). The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₃₉ H ₂₉ N ₃ (= 539.69) Calculated value (%): C 86.80 H: 5.42 N: 7.79 Actual value (%): C: 86.79 H: 5.34 N: 7.77 Example 2 <Synthesis of Phenanthrene Derivative Represented by Formula (2)>
Instead of the sodium amide used in Example 1, the above formula
In the same manner as in Example 1 except that 1.29 g of sodium amide in which R ^{1 in} (b) was a phenyl group and R ² was a methyl group, R ¹ in the above formula (c) was phenyl. Group,
2.46 g (yield 79%) of an aldehyde compound in which R ² was a methyl group and R ⁵ and R ⁶ were both hydrogen atoms was obtained.

Then, the aldehyde compound 1.56
g together with 0.44 g of a hydrazine compound in which both R ³ and R ⁴ in the formula (d) are ethyl groups.
In the same manner as described above, 1.59 g (83% yield) of the phenanthrene derivative represented by the above formula (2) was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₂₆ H ₂₇ N ₃ (= 381.53) Calculated value (%): C: 81.85 H: 7.13 N: 11.01 Actual value (%): C: 81. 83 H: 7.08 N: 11.07 Example 3 <Synthesis of phenanthrene derivative represented by the above formula (3)>
Instead of the sodium amide used in Example 1, the above formula
(b) R ¹ in, except that R ² is using sodium amide 0.95g are both ethyl groups, in the same manner as in Example 1, R ^1, R ² in the formula (c) is Both are ethyl groups,
2.11 g (76% yield) of an aldehyde compound in which both R ⁵ and R ⁶ were hydrogen atoms was obtained.

Then, the aldehyde compound 1.39 was obtained.
g is reacted with 0.92 g of a hydrazine-based compound wherein R ³ and R ⁴ in the formula (d) are both phenyl groups in the same manner as in Example 1 to obtain a compound represented by the formula (3). 1.58 g (yield 71%) of the phenanthrene derivative was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₃₁ H ₂₉ N ₃ (= 443.6) Calculated value (%): C: 83.94 H: 6.59 N: 9.47 Actual value (%): C: 83. 97 H: 6.55 N: 9.47 Example 4 <Synthesis of phenanthrene derivative represented by the above formula (4)>
Instead of the sodium amide used in Example 1, the above formula
In the same manner as in Example 1 except that 2.41 g of sodium amide wherein R ^{1 in} (b) was a phenyl group and R ² was a β-naphthyl group was used, R ¹ in the above formula (c) was used. Is a phenyl group, R ² is a β-naphthyl group, and R ⁵ and R ⁶ are both hydrogen atoms 3.47 g (yield 82%)
I got

The aldehyde compound 2.12
g with hydrazine compound 1.17 g in which R ³ in the formula (d) is a phenyl group and R ⁴ is a β-naphthyl group in the same manner as in Example 1 to obtain a compound of the formula (4)
2.40 g of phenanthrene derivative represented by
%). The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₄₇ H ₃₃ N ₃ (= 639.81) Calculated value (%): C: 88.23 H: 5.20 N: 6.57 Actual value (%): C: 88. 23 H: 5.19 N: 6.54 Example 5 <Synthesis of phenanthrene derivative represented by the above formula (5)>
Instead of 9-bromo-10-formylphenanthrene used in Example 1, R ⁵ in the formula (a) is a phenyl group, R ⁶
Is a hydrogen atom, n = 1, and 3.61 g of 3-phenyl-9-bromo-10-formylphenanthrene in which the substitution position of R ⁵ is the 3-position of phenanthrene was used. Thus, 3.46 g (77% yield) of an aldehyde compound in which R ¹ and R ² in the above formula (c) were both phenyl groups, R ⁵ was a phenyl group, and R ⁶ was a hydrogen atom was obtained.

Then, the aldehyde compound 2.25 was obtained.
g is reacted with 0.92 g of a hydrazine-based compound wherein R ³ and R ⁴ in the formula (d) are both phenyl groups in the same manner as in Example 1 to obtain a compound represented by the formula (5). 2.43 g (79% yield) of the phenanthrene derivative was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₄₅ H ₃₃ N ₃ (= 615.78) Calculated value (%): C 87.77 H: 5.40 N: 6.82 Actual value (%): C: 87.76 H: 5.46 N: 6.90 Example 6 <Synthesis of Phenanthrene Derivative Represented by Formula (6)>
Instead of 9-bromo-10-formylphenanthrene used in Example 1, R ⁵ and R ⁶ in the formula (a) are both methyl groups, n = 1, and the substitution position of R ⁵ and R ⁶ is phenanthrene. 3,6-dimethyl-9-bromo-1 at the 3- and 6-positions
In the same manner as in Example 1 except that 2.33 g of 0-formylphenanthrene was used, both R ¹ and R ² in the above formula (c) were phenyl groups, and both R ⁵ and R ⁶ were methyl groups. 3.33 g of an aldehyde compound (81% yield)
I got

Then, the aldehyde compound 2.05
g is reacted with 0.92 g of a hydrazine-based compound in which R ³ and R ⁴ in the formula (d) are both phenyl groups in the same manner as in Example 1 to obtain a compound represented by the formula (6). 2.10 g (74% yield) of the phenanthrene derivative was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₄₁ H ₃₃ N ₃ (= 567.74) Calculated value (%): C 86.74 H: 5.86 N: 7.40 Actual value (%): C: 86.71 H: 5.92 N: 7.39 Example 7 <Synthesis of phenanthrene derivative represented by the above formula (7)>
In the same manner as in Example 1, 2.80 g (yield: 75%) of the aldehyde compound in which R ¹ and R ² in the formula (c) are both phenyl groups and R ⁵ and R ⁶ are both hydrogen atoms. Was.

Then, the aldehyde compound 1.87 was obtained.
g was reacted with 0.87 g of a hydrazine compound in which R ³ in the formula (d) is a phenyl group and R ⁴ was a pyrrole group in the same manner as in Example 1 to obtain a compound represented by the formula (7). 2.01 g (yield 76%) of the resulting phenanthrene derivative was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₃₇ H ₂₈ N ₄ (= 528.66) Calculated value (%): C 84.06 H: 5.34 N: 10.60 Actual value (%): C: 84.09 H: 5.37 N: 10.61 Example 8 <Synthesis of phenanthrene derivative represented by the above formula (8)>
Instead of 9-bromo-10-formylphenanthrene used in Example 1, both R ⁵ and R ⁶ in the formula (a) are chlorine atoms, n = 1, and the substitution position of R ⁵ and R ⁶ is phenanthrene. 3,6-dichloro-9-bromo-1 at positions 3 and 6
In the same manner as in Example 1 except that 3.54 g of 0-formylphenanthrene was used, both R ¹ and R ² in the formula (c) were phenyl groups, and both R ⁵ and R ⁶ were chlorine atoms. 2.88 g of a certain aldehyde compound (65% yield)
I got

Then, the aldehyde compound 2.21 was obtained.
g is reacted with 0.92 g of a hydrazine-based compound wherein R ³ and R ⁴ in the formula (d) are both phenyl groups in the same manner as in Example 1 to obtain a compound represented by the formula (8). 1.99 g (74% yield) of the phenanthrene derivative was obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₃₉ H ₂₇ N ₃ Cl ₂ (= 537.67) Calculated value (%): C 87.12 H: 5.06 N: 7.82 Actual value (%): C: 87 0.03 H: 5.13 N: 7.80 Examples 9 to 16 and Comparative Example 1 (single-layer type photoreceptor) 8 parts of a perylene pigment represented by the following formula (A) as a charge generating material, Phenanthrene derivative 1 obtained in 1 to 6
50 parts and 100 parts of polycarbonate as a binder resin were dispersed in an appropriate amount of methyl chloride to prepare a dispersion, and the obtained dispersion was applied to the surface of an aluminum tube by a dipping method. , Dried at 100 ° C for 1 hour, 20μ
m of the photosensitive layer was obtained.

[0060]

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In Comparative Example 1, DEH represented by the following formula (B) was used.
Except that 100 parts was used as the charge transport material, a single-layer type photoreceptor was produced in the same manner as in Examples 9 to 16 above.

[0062]

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With respect to the photoreceptors of the above Examples and Comparative Examples,
The following tests were performed to evaluate the characteristics. Measurement of Initial Surface Potential Each photoconductor was loaded into an electrostatic copying tester (model number EPA-8100 manufactured by Kawaguchi Electric Co., Ltd.), and the surface thereof was charged positively to obtain an initial surface potential V1 sp. Was measured.

Measurement of Half Reduction Exposure Amount and Residual Potential The photosensitive member charged in the above measurement of the initial surface potential was
Using a halogen lamp as an exposure light source of the electrostatic copying test apparatus, exposure was performed under the conditions of an exposure intensity of 10 lux, and the time required for the surface potential to be reduced to 1/2 was determined.
2 (lux · sec) was calculated.

The surface potential was measured 0.5 seconds after the start of the exposure, and the measured value was taken as the residual potential V1r.p. (V). Measurement of light stability The above photoreceptor was exposed to a white fluorescent lamp at an exposure intensity of 5000.
After exposure for 10 minutes under lux conditions,
Initial surface potential V2s.p. (V), residual potential V2r.p. (V)
Was measured. The difference ΔVs.p. (V) from the initial surface potential V1s.p. and the difference ΔV from the residual potential V1r.p.
rp (V) was determined.

Table 1 shows the test results.

[0067]

[Table 1]

From these test results, the photoreceptors of each of the examples have almost no difference in initial surface potential V1 sp. From the conventional photoreceptor of the comparative example. 2 was small and the residual potential V1r.p. was low, indicating that the sensitivity was significantly improved. Also,
The photoreceptors of each of the above examples have almost no difference in ΔVs.p. from the photoreceptors of the comparative example, but all have excellent durability since ΔVr.p. is smaller than that of the comparative example. It turned out to be.

[0069]

As described above, since the phenanthrene derivative of the present invention has a high charge transporting ability and is excellent in photostability, a high sensitivity can be obtained by using this phenanthrene derivative as a charge transporting material. And a photosensitive member having excellent durability can be obtained.

Claims (2)

(57) [Claims] 1. A compound of the general formula (I): ^{Wherein, R 1, R 2, R} 3, R 4 are the same or different alkyl group, an aryl group or a heterocyclic group, R ^5,
R ⁶ is the same or different and represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group. n shows the integer of 1-4. ] The phenanthrene derivative represented by these. 2. A photoreceptor comprising: a photosensitive layer containing a phenanthrene derivative represented by the general formula (I) provided on a conductive substrate.