JP3173829B2 - 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 generation material that generates a charge upon exposure and a charge transport material having a function of transporting the generated charge.

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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Wherein R ¹ , R ² , R ³ and R ⁴ are the same or different and are each an alkyl group, an aryl group, or a thienyl group;
Pyrrolyl group, oxazolyl group, isoxazolyl group,
Azolyl group, isothiazolyl group, imidazolyl group, 2H
-Imidazolyl, pyrazolyl, triazolyl,
One of the trazolyl, pyranyl, and pyridyl groups
Shows the heterocyclic group Zureka, R ^5, R ⁶ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group. n shows the integer of 1-4. ]. The 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.

As the heterocyclic group, thienyl group, pyrrolyl
Group, oxazolyl group, isoxazolyl group, thiazolyl
Group, isothiazolyl group, imidazolyl group, 2H-imida
Zolyl, pyrazolyl, triazolyl, tetrazolyl
And any one of a pyryl group, a pyranyl group, and a pyridyl group .

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. R ⁷ represents a lower alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group, and a methyl group and an ethyl group are particularly preferably used. That is, as shown in the above reaction formula, the 9,10-diformylphenanthrene derivative represented by the formula (a) is added to the formula (b)
Is reacted in the presence of a basic substance and a solvent to obtain an aldehyde compound represented by the formula (c). Then, the compound (c) is represented by the formula
By reacting the methylphosphonate represented by (d) in the presence of a basic substance and a solvent,
The phenanthrene derivative of the present invention represented by the formula (I) is obtained.

The methylphosphonate represented by the formula (b) is used in a 0.5-fold molar amount with respect to the 9,10-diformylphenanthrene derivative represented by the formula (a),
The methylphosphonic acid ester represented by (d) is used in an equimolar amount to the aldehyde compound represented by the formula (c). Examples of the basic substance include alcoholates such as sodium methylate, sodium ethylate and potassium t-butylate, as well as sodium acetate, sodium hydroxide,
Potassium hydroxide, sodium amide, sodium hydride and the like can be used.
In each case, for the 0-diformylphenanthrene derivative or the aldehyde compound represented by the formula (c),
0.5 equivalent.

As the solvent, methanol, ethanol,
Alcohols such as isopropyl alcohol, methyl cellosolve and ethyl cellosolve; glycols such as ethylene glycol and propylene glycol; ethers such as dioxane and tetrahydrofuran; N, N'-dimethylformamide, dimethyl sulfoxide and the like. N'-dimethylformamide is preferably used. The amount of the solvent used is not particularly limited in any case, and it suffices that the amount used is 1 to 20 times the total amount of the compounds used in the reaction.

The reaction proceeds sufficiently at room temperature without heating, but the reaction time may be shortened by heating. The reaction temperature is preferably in the range of 10 to 110C, more preferably in the range of 20 to 70C.
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. Among the phenanthrene derivatives represented by the general formula (I), R ¹ , R ² and R ³ ,
When R ⁴ is a combination of the same groups,
A methylphosphonate represented by the formula (b) is converted to a compound represented by the formula (a)
Can be synthesized by a one-step reaction using an equimolar amount with respect to the 9,10-diformylphenanthrene derivative represented by the following formula. At this time, the basic substance is used in an amount of 1.0 equivalent to the 9,10-diformylphenanthrene derivative represented by the formula (a).

The photoreceptor of the present invention comprises a photosensitive layer containing one or more of the phenanthrene derivatives represented by the above 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 generating layer containing a charge generating 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 above 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 transporting materials are used alone or as a mixture 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 resin 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 laminated photoreceptor, the charge generation material and the binder resin constituting the charge generation layer can be used in various ratios. 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 formula (I) and the binder resin constituting the charge-transporting layer can be used in various forms within a range that does not hinder 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, particularly 25 to 200 parts. Also,
The thickness of the laminated photosensitive layer is 0.01 to 5 μm for the charge generation layer.
m, preferably about 0.1 to 3 μm, and the charge transport layer is 2 to 100 μm, particularly 5 to 50 μm.
m is preferable.

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 a 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.

[0042]

The present invention will be described below in detail with reference to examples and comparative examples. Example 1 <Synthesis of Phenanthrene Derivative Represented by Formula (1)> In the formula (a), R ⁵ and R ⁶ are both hydrogen atoms.
2.34 g of 0-diformylphenanthrene and the above formula
(b) 5.52 g of a methylphosphonic acid ester in which R ¹ and R ² are both a phenyl group and R ⁷ is a methyl group are dissolved in 100 ml of benzene together with 1.64 g of sodium acetate, and the mixture is dissolved at 70 ° C. for 5 hours. By refluxing, the phenanthrene derivative 3.8 represented by the above formula (1) is obtained by a one-step reaction.
4 g (yield 72%) were obtained.

Analysis results of the obtained phenanthrene derivative
Is shown below. Elemental analysis result C₄₂H₃₀(= 534.71) Calculated value (%): C 94.34 H: 5.66 Actual value (%): C: 94.30 H: 5.74Example 2 <Synthesis of Phenanthrene Derivative Represented by Formula (2)> R in Formula (a)^Five, R⁶Are both hydrogen atoms
2.34 g of 0-diformylphenanthrene and the above formula
(b) R in¹Is a phenyl group, R^TwoIs a methyl group, R ⁷But
2.14 g of methylphosphonic acid ester, which is a tyl group,
Together with 0.82 g of sodium acetate and benzene 10
0 ml, refluxed at 60 ° C. for 3 hours,
R in¹Is a phenyl group, R^TwoIs a methyl group, R^Five, R⁶But
2.48 g of aldehyde compounds both of which are hydrogen atoms (yield
77%).

Then, the aldehyde compound 1.61 was obtained.
g, R ³ and R ⁴ in the above formula (d) are both ethyl groups, R ⁷
Is a methylphosphonic ester 0.90
g, 0.41 g of sodium acetate, and benzene 10
0 ml, refluxed at 70 ° C. for 5 hours,
1.56 g (yield 83)
%).

Analysis results of the obtained phenanthrene derivative
Is shown below. Elemental analysis result C₂₉H₂₈(= 376.55) Calculated value (%): C: 92.50 H: 7.50 Actual value (%): C: 92.53 H: 7.51Example 3 <Synthesis of Phenanthrene Derivative Represented by Formula (3)> Instead of the methylphosphonate used in Example 2,
Thus, R in the above formula (b)¹, R^TwoAre both ethyl groups, R⁷But
1.80 g of methylphosphonic acid ester, which is a methyl group,
Except for using, the same formula as in Example 2 was used.
(c) R in¹, R ^TwoAre both ethyl groups, R^Five, R⁶Together
2.25 g of an aldehyde compound which is a hydrogen atom (yield 7
8%).

Then, the aldehyde compound 1.44
g, R ³ and R ⁴ in the formula (d) are both a phenyl group, R
Methylphosphonic acid ester in which ⁷ is a methyl group 1.38
g, and reacted in the same manner as in Example 2 to obtain 1.91 g of the phenanthrene derivative represented by the formula (3).
(87% yield). The analysis results of the obtained phenanthrene derivative are shown below.

[0047] Elemental analysis C ₃₄ H ₃₀ (= 438.62) Calculated (%): C: 93.11 H : 6.89 Found (%): C: 93.14 H : 6.93 embodiments Example 4 <Synthesis of Phenanthrene Derivative Represented by Formula (4)> Instead of the methylphosphonate used in Example 1, R ¹ in the formula (b) is a phenyl group, and R ² is a β-naphthyl group. , except that R ⁷ is used methylphosphonate ester 6.52g a methyl group, in the same manner as in example 1, the reaction of one step, phenanthrene derivatives 5.08g represented by the formula (4) (81% yield).

The analysis results of the obtained phenanthrene derivative are shown below. Elemental analysis C ₅₀ H ₃₄ (= 634.83) Calculated (%): C: 94.60 H : 5.40 Found (%): C: 94.63 H : 5.33 Example 5 < Synthesis of Phenanthrene Derivative Represented by Formula (5)> Instead of 9,10-diformylphenanthrene used in Example 1, R ⁵ in the formula (a) is a phenyl group, R ⁶ is a hydrogen atom, n = 1 and the substitution position of R ⁵ is 3 of phenanthrene
Phenanthrene derivative represented by the above formula (5) by a one-step reaction in the same manner as in Example 1 except that 3.10 g of 3-phenyl-9,10-diformylphenanthrene was used. 4.34 g (yield 71%) was obtained.

The analysis results of the obtained phenanthrene derivative are shown below. Elemental analysis C ₄₈ H ₃₄ (= 610.81) Calculated (%): C: 94.39 H : 5.61 Found (%): C: 94.47 H : 5.65 Example 6 < Synthesis of Phenanthrene Derivative Represented by Formula (6)> Instead of 9,10-diformylphenanthrene used in Example 1, R ⁵ and R ⁶ in the formula (a) are both methyl groups, n
= 1 and 2.62 g of 3,6-dimethyl-9,10-diformylphenanthrene, in which the substitution positions of R ⁵ and R ⁶ are the 3- and 6-positions of phenanthrene, were used. Similarly, by a one-step reaction, the above formula (6)
4.39 g of a phenanthrene derivative represented by the following formula (yield: 78)
%).

The analysis results of the obtained phenanthrene derivative are shown below. Elemental analysis C ₄₄ H ₃₄ (= 562.76) Calculated (%): C: 93.91 H : 6.09 Found (%): C: 93.90 H : 6.14 Example 7 < Synthesis of Phenanthrene Derivative Represented by Formula (7)> Instead of the methylphosphonate used in Example 2, R ¹ and R ² in the formula (b) are both a phenyl group, R ⁷
Is a methyl group, 2.76 g of a methylphosphonic ester
In the same manner as in Example 2 except that aldehyde compound was used, 3.00 g of an aldehyde compound in which R ¹ and R ² in the formula (c) were both phenyl groups and R ⁵ and R ⁶ were both hydrogen atoms. (78% yield).

The aldehyde compound 1.92
g was reacted with 1.39 g of a methylphosphonate in which R ³ in the formula (d) was a phenyl group, R ⁴ was a pyrrole group, and R ⁷ was a methyl group, in the same manner as in Example 2 above. Phenanthrene derivative represented by the formula (7)
92 g (69% yield) were obtained. The analysis results of the obtained phenanthrene derivative are shown below.

Elemental analysis result: C ₄₁ H ₂₉ N ₁ (= 535.69) Calculated value (%): C: 91.93 H: 5.46
N: 2.61 Actual value (%): C: 91.97 H: 5.43
N: 2.68 Example 8 <Synthesis of Phenanthrene Derivative Represented by Formula (8)> Instead of 9,10-diformylphenanthrene used in Example 1, R ⁵ and R in the formula (a) were used. ⁶ are both chlorine atoms, n
= 1 and 5.52 g of 3,6-dichloro-9,10-diformylphenanthrene in which the substitution positions of R ⁵ and R ⁶ are the 3- and 6-positions of phenanthrene were used. Similarly, by a one-step reaction, the above formula (8)
4.11 g (yield 68)
%).

The analysis results of the obtained phenanthrene derivative are shown below. Elemental analysis _{C 42 H 34 Cl 2 (=} 603.60) Calculated (%): C: 94.70 H : 5.30 Found (%): C: 94.73 H : 5.26 Example 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, and 80 parts of a phenanthrene derivative obtained in Examples 1 to 8 A dispersion was prepared by dispersing 100 parts of polycarbonate as a resin for adhesion in an appropriate amount of methyl chloride, and the resulting dispersion was applied to the surface of an aluminum tube by a dipping method. Dry for 20 hours
m of the photosensitive layer was formed to obtain a positively charged single-layer photosensitive member.

[0054]

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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.

[0056]

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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 photoreceptor was loaded into an electrostatic copying tester (Gentec Cynthia 30M, manufactured by Gentec), and the surface thereof was charged positively to obtain an initial surface potential V1s.p. V) 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 above test results.

[0061]

[Table 1]

From these test results, the photoreceptors of each of the examples have almost no difference in the initial surface potential V1s.p. 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.

[0063]

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 , and R ⁴ are the same or different and each is an alkyl group, an aryl group, a thienyl group, a pyrrolyl group,
Oxazolyl group, isoxazolyl group, thiazolyl group,
Isothiazolyl group, imidazolyl group, 2H-imidazolyl group
, Pyrazolyl, triazolyl, tetrazolyl
And R ⁵ and R ⁶ are the same or different and represent 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 conductive substrate and a photosensitive layer containing a phenanthrene derivative represented by the above general formula (I).